basf productcatalog inorganic-specialties
TRANSCRIPT
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Life Science Intermediatesfor Organic Synthesis
Product Overview
Partner with us from lab to launch
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Table of Contents
Suzuki Coupling Reagents ..............................................................................................................................................1
Borane Complexes .........................................................................................................................................................1
Amine Boranes ................................................................................................................................................................1
Chiral Reagents............................................................................................................................................................... 2
Calselect® Reducing Agents ...........................................................................................................................................2
Alkylboranes....................................................................................................................................................................3
Boroxins and Borates ..................................................................................................................................................... 3
Alkali Metal Alcoholates ..................................................................................................................................................4
Alkali Metal Amides .........................................................................................................................................................5
Other Alkali Metal Compounds .......................................................................................................................................5
Hydroxyacetophenones and Phenyl Acetate ..................................................................................................................5
Hydroxylamine Derivatives ..............................................................................................................................................6
High Purity Iron Salts ...................................................................................................................................................... 6
Index ...............................................................................................................................................................................7
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Suzuki Coupling ReagentsBoronic acids and esters have become very important building blocks in organic synthesis through the Suzuki-Miyaura cross-coupling
protocols. The Suzuki-Miyaura reaction1 is a powerful synthetic tool for the formation of carbon-carbon bonds, dramatically shortening
multistep synthetic routes since this process easily couples large molecular fragments containing functional groups. Trialkylborane and
aryldialkylborane reagents can also participate in these valuable coupling reactions.
1Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
Name Abbreviation/Trade Name Structure CAS#
FormulaFW (g/mol) Form
Density(g/ml)
Bis(pinacolato)diboron PIN2B2 73183-34-3 C12H24B2O4253.94
Powder
Catecholborane CATB 274-07-7 C6H
5BO
2
119.92
50 wt% in toluene 0.911
Pinacolborane PINB 25015-63-8 C6H
13BO
2
128.00
Neat w/ 1% TEA 0.875
Borane ComplexesBorane complexes are versatile compounds commonly used as regio-, chemo- and stereoselective reducing agents for a variety
of functional groups such as aldehydes, ketones, carboxylic acids, amides and olefins. The high yields and simple isolation of the
reduced products combined with the high selectivities achieved with borane reagents have made these compounds the favorite
reducing agents for a number of applications.
Name Abbreviation/Trade Name Structure CAS#
FormulaFW (g/mol) Form
Density(g/ml)
Borane tetrahydrofuran complex BTHF 14044-65-6 C4H
11BO
85.94
1M in THF 0.878
Dimethylsulfide borane complex DMSB 13292-87-0 C2H
9BS
75.97
10M in DMS
2M in THF
0.794
0.865
Amine BoranesComplexation of borane with a strong Lewis base, such as an unhindered amine, produces air and moisture stable amine borane
complexes. The stability, solubility, and ease of handling make them attractive borane sources in many reactions where aqueous,alcoholic or acidic solvents are desirable. 5-Ethyl-2-methylpyridine borane is a new complex which is easily handled and has up to
three hydrides available for reductive amination and reduction.
Name Abbreviation/Trade Name Structure CAS#
FormulaFW (g/mol) Form
Density(g/ml)
2-Picoline borane PICB 3999-38-0 C7H
10BN
103.95
30 wt% THF 0.909
5-Ethyl-2-methylpyridine borane PEMB 1006873-58-0 C8H
14BN
135.01
Neat liquid 0.913
Dimethylamine borane DMAB 74-94-2 C2H
10BN
58.92
Neat Solid 0.73 g/cc
N,N-Diethylaniline borane DEANB 13289-97-9 C10
H18
BN
163.07
Neat liquid 0.921
Pyridine borane PYB 110-51-0 C5H
8BN
92.93
Neat liquid 0.921
t-Butylamine borane TBAB 7337-45-3 C4H
14BN
86.97
Powder 0.46 g/cc(bulk)
Triethylamine borane TEAB 1722-26-5 C6H
18BN
115.03
Neat liquid 0.782
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Chiral ReagentsBoth methyl oxazaborolidine (MeCBS) and diisopinocampheylchloroborane (DPC) are excellent choices for the enantioselective
reduction of prochiral ketones. While DPC is a stoichiometric reducing agent, MeCBS (Corey catalyst) is a catalyst that is typically
used in conjunction with a borane source such as borane tetrahydrofuran (BTHF), dimethylsulfide borane (DMSB) or N,N-diethylaniline
borane (DEANB). Both products have proven their advantages over alternative technologies in commercial applications and are
available in both enantiomeric forms from BASF.
Name Abbreviation/Trade Name Structure CAS#
FormulaFW (g/mol) Form
Density(g/ml)
(-)-Diisopinocampheylchloroborane (-)-DPC 85116-37-6 C20
H34
BCl
320.80
60-65 wt% heptanes 0.855
(+)-Diisopinocampheylchloroborane (+)-DPC 112246-73-8 C20
H34
BCl
320.80
60-65 wt% heptanes
60-65 wt% hexanes
0.855
0.890
(R)-Methyl oxazaborolidine (R)-MeCBS 112022-83-0 C18
H20
BNO
277.17
1M in toluene 0.927
(S)-Methyl oxazaborolidine (S)-MeCBS 112022-81-8 C18
H20
BNO
277.17
1M in toluene 0.927
Calselect® Reducing Agents Alkali metal trialkylborohydrides have been used in numerous stereoselective and regioselective reductions. The strength and reactivity
of these reducing agents varies with the steric bulk of the alkyl groups and the alkali metal ion. Calselect® STAB is a selective reducing
agent that has proven to be extremely useful in reductive aminations.
Name Abbreviation/Trade Name Structure CAS#
FormulaFW (g/mol) Form
Density(g/ml)
Lithium triethylborohydride CALSELECT® LT 22560-16-3 C6H
16BLi
105.95
1M in THF 0.890
Lithium tri-sec- butylborohydride CALSELECT® L i 38721-52-7 C12
H28
BLi
190.11
1M in THF 0.898
Sodium triacetoxyborohydride CALSELECT® STAB 56553-60-7 C6H
10BNaO
6
211.96
Powder
Granular
0.765 g/cc
(bulk)
Sodium tri-sec- butylborohydride CALSELECT® Na 67276-04-4 C12
H28
BNa
206.15
1M in THF 0.898
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Alkylboranes Alkylboranes are versatile products used in different industrial applications such as Pharmaceuticals, Polymers and others. In organic
synthesis triethylborane (TEB) and methoxydiethylborane (MDEB) have proven especially effective as diastereoselective reagents
to produce syn-diols from β-hydroxyketones. Dibutylboron triflate (DBBT) is used to form boron enolates in diastereoselective aldol
condensations following the Evans’ and similar protocols. BASF’s ready-to-use solution of DBBT is now available from lab scale to ton
quantities as solutions in toluene.
Name Abbreviation/Trade Name Structure CAS#
FormulaFW (g/mol) Form
Density(g/ml)
9-Borabicyclo[3.3.1]nonane 9BBN 280-64-8 C8H
15B
122.02
0.5M in THF 0.882
Dibutylboron triflate DBBT 60669-69-4 C9H
18BF
3O
3S
274.15
1M in toluene 0.903
Methoxydiethylborane MDEB 7397-46-8 C5H
13BO
99.97
Neat liquid
50 wt% in THF
0.749
0.807
Triethylborane TEB 97-94-9 C6H
15B
98.00
Neat liquid
14 wt% in THF
0.696
0.848
Triethylborane-1,3-diaminopropane complex TEB-DAP 148861-07-8 C9H
25BN
2
172.12
Neat liquid 0.859
Tri-n-butylborane TNBB 122-56-5 C12
H27
B
182.16
Neat liquid 0.748
Tri-n-butylborane-3-methoxypropylamine complex TnBB-MOPA 345269-15-0 C15
H37
BN2
271.25
Neat liquid 0.826
Boroxins and Borates
Name Abbreviation/Trade Name Structure CAS#
FormulaFW (g/mol) Form
Density(g/ml)
Trimethoxyboroxin TMBX 102-24-9 C3H
9B
3O
6
173.53
Neat liquid 1.216
Trimethylboroxin MBX 823-96-1 C3H
9B
3O
3
125.53
50 wt% in THF 0.894
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Alkali Metal Alcoholates Alcoholates are moderately strong base reagents that are used in many drug and chemical synthesis applications, such as alkylation,
arylation, acylation, solvolysis of esters, condensation, elimination, isomerization, rearrangements, transfer, hydrogenation, Wittig
reactions, and redox reactions. The reactivity can be fine tuned to the desired reaction by correct choice of alcoholate and counterion.
The wide range of properties and solubilities available from BASF Corporation allows for process optimization and high yields.
Potassium Alcoholates
Name/Synonym Abbreviation/Trade Name Structure CAS #
FormulaFW (g/mol) Forms
Density(g/ml)
Potassium 3,7-Dimethyl-3-octylatePotassium 3,7-Dimethyl-3-octanoxide
KDMO/Heptane 50% 263148-42-1 C10H21KO196.37
50% w/w inn-heptane 0.804
Potassium Ethylate
Potassium Ethoxide
KE 24%
(DN with toluene)
917-58-8 C2H
5KO
84.14
24% w/w in ethanol 0.895
Potassium Methylate
Potassium Methoxide
KM
KM 32% KOMe865-33-8 CH
3KO
70.14
Powder
32% w/w inmethanol
0.978
Potassium tert.- Amylate
Potassium tert.-Pentoxide
KTA
KTA/Cyclohexane 15%
KTA/Toluene 25%
KTA/THF 45%
41233-93-6 C5H
11KO
126.20
Powder
15% w/w incyclohexane
25% w/w in toluene
45% w/w in THF
0.57 g/cc(Bulk)
0.801
0.904
0.951 @21˚C
Potassium tert.- Butylate
Potassium tert-Butoxide
KTB
KTB/TBA 15%
KTB/THF 20%
KTB/TBA 13.7%with THF
865-47-4 C4H
9KO
112.21
Powder
15% w/w in tert.-butanol
20% w/w in THF
13.7% w/w in TBAwith THF
0.813
0.818
0.906
0.838 @25˚C
Sodium Alcoholates
Name/Synonym Abbreviation/Trade Name Structure CAS #
FormulaFW (g/mol) Forms
Density(g/ml)
Sodium EthylateSodium Ethoxide
SESE 21%
141-52-6 C2H5NaO68.05
Powder21% w/w in ethanol 0.880
Sodium Mentholate NaM/Hexanes 50% 19321-38-1 C10
H19
NaO
178.25
50% w/w in hexanes 0.815
Sodium Methylate
Sodium Methoxide
SM
SMS 25%
SMS 30%
NaOMe
124-41-4 CH3NaO
54.03
Powder
25% w/w inmethanol
30% w/w inmethanol
0.944
0.969
Sodium n- Butylate
Sodium n-Butoxide
SNB/NBA 19% 2372-45-4 C4H
9NaO
96.1
19% w/w inn-butanol
0.853
Sodium tert.- Amylate
Sodium tert.-Pentoxide
STA
STA/Hexanes 38%
STA/THF 35%
STA/Toluene 25%
14593-46-5 C5H
11NaO
110.13
Powder
38% w/w in hexanes
35% w/w in THF
25% w/w in toluene
0.752
0.926
0.885
Sodium tert.- Butylate
Sodium tert.-Butoxide
STB 865-48-5 C4H
9NaO
96.02
Powder 0.698 g/cc(Bulk)
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Alkali Metal AmidesPotassium hexamethyldisilazane (KHMDS), sodium hexamethyldisilazane (NaHMDS), and lithium hexamethyldisilazane (LiHMDS)
are strong non-nucleophilic base reagents useful in a wide variety of chemical reactions and transformations. Applications include
aklylation, acylation, ring formation, isomerization, rearrangements, aldol condensations, Wittig and Horner-Emmons reactions and
polymerization. Their high selectivity and specificity can lead to simpler, less expensive purification routes to the desired product.
Name/Synonym Abbreviation/Trade Name Structure CAS #
FormulaFW (g/mol) Forms
Density(g/ml)
Potassium Hexamethyldisilazane
Potassium bi(trimethylsily)amide
KHMDS/THF 20%
KHMDS/Toluene
15%
40949-94-8 C6H
18KNSi
2
199.5
20% w/w in THF
15% w/w in toluene
0.898
0.879
Lithium Hexamethyldisilazane
Lithium bi(trimethylsily)amide
LiHMDS/THF 24% 4039-32-1 C6H
18LiNSi
2
167.33
24% w/w in THF 0.867
Sodium Hexamethyldisilazane
Sodium bis(trimethylsilyl)amide
NaHMDS/THF 40%
NaHMDS/Toluene13%
1070-89-9 C6H
18NNaSi
2
183.38
40% w/w in THF
13% w/w in toluene
0.889
0.868 @21.0 ˚C
Other Alkali Metal Compounds
Sodium-Potassium Alloy (NaK), essentially a liquid form of Potassium metal, is mainly used for reductions and as a raw material formaking potassium derivatives. Potassium superoxide (KO
2 ) has its main applications as a chemical oxygen source.
Name/Synonym Abbreviation/Trade Name Structure CAS #
FormulaFW (g/mol) Forms
Density(g/ml)
Potassium Superoxide KO2 CAT
KO2 UNCAT
KO2 UNCAT fluff
KO2
12030-88-5 KO2
Catalyzed granules
Uncatalyzed granules
Uncatalyzed fluff
Sodium Potassium Alloy NaK NaK 11135-81-2 NaK Liquid 0.855
Hydroxyacetophenones and Phenyl Acetate4-Hydroxyacetophenone (4-HAP) is a versatile building block for a variety of uses including semiconductors, specialty polymers,
pharmaceuticals, agricultural chemicals, flavors and fragrances, cosmetic and other fine chemical applications.
Name/Synonym Abbreviation/Trade Name Structure CAS No.
FormulaFW (g/mol) Forms
Density(g/ml)
2-Hydroxyacetophenone 2-HAP
Ortho-Hydroxyacetophenone
118-93-4 C8H
8O
2
136.15
Liquid 1.157
Bulk
4-Hydroxyacetophenone 4-HAP
1-(4-Hydroxyphenyl)ethanone
p-Hydroxyacetophenone
p-Hydroxyphenyl methylketone
99-93-4 C8H
8O
2
136.15
Powder 1.157
Bulk
Phenyl Acetate PhOAc 122-79-2 C7H
14O
2
130.2
Liquid 0.875-
0.877
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Hydroxylamine DerivativesBASF offers a growing range of Hydroxylamine derivatives used to introduce N-O-functionality into a molecule. Recent examples
of our ongoing portfolio expansion include: Hydroxylamine-O-sulfonic acid, a versatile aminating agent; O-Benzylhydroxylamine
hydrochloride, used to introduce an N-O functionality that is protected from other reactions and easily de-protected under mild
conditions; and N,O-Dimethylhydroxylamine hydrochloride that makes production-scale “Weinreb-Chemistry” feasible.
Name/Synonym Abbreviation/Trade Name Structure CAS No.
FormulaFW (g/mol) Forms
Density(g/ml)
Hydroxylamine-O-sulfonic Acid HOSA 2950-43-8 H3NO
4S
113.09
Solid 2.2 g/cc
O-Benzylhydroxylamine Hydrochloride
O-Benzyhydroxylammonium Chloride
OBHA•HCl 2687-43-6 C7H
10ClNO
159.62
Solid .370 g/cc
O-Methylhydroxylamine Hydrochloride
O-Methylhydroxylammonium Chloride
O-MHA•HCl 593-56-6 CH6ClNO
83.52
30% Solution 1.15 g/ml
N,O-Dimethylhydroxylamine Hydrochloride
N,O-Dimethylhydroxylammonium Chloride
NODMHA•HCl 6638-79-5 C2H
8ClNO
97.54
Solid
N-Hydroxyphtalimide NHPI 524-38-9 C8H
5NO
3
163.13
Solid
2, 3-Butanedione monoxime BDMO 57-71-6 C4H
7NO
2
101.11
Solid
High Purity Iron SaltsBASF reliably helps to fulfill the legal restrictions like the EMEA directive (European Medicine Agency) and recommendations from US
Pharmacopoeia (USP) by offering high purity solutions with trace metal impurities in single digit ppm level. BASF’s high purity iron
salts are based on BASF’s experienced and well-established iron technology. Full backward integration ensures a reliable supply of
raw materials. BASF offers a high variety of different anions and also other high purity metals on request.
Name/Synonym Abbreviation/Trade Name Structure CAS No.
FormulaFW (g/mol) Forms
Density(g/ml)
Ferric Chloride Solution
High Purity
Iron(III) ChlorideSolution
7705-08-0 FeCl3
162.20
12% Solution (Fe3+ ) 1.36 g/ml
Ferric Sulfate Solution
High Purity
Iron(III) SulfateSolution
10028-20-5 Fe2(SO
4 )
3
399.88
12% Solution (Fe3+ ) 1.50 g/ml
Ferrous Sulfate Solution
High Purity
Iron(II) SulfateSolution
7720-78-7 FeSO4
151.91
9% Solution
BASF offers a large variety of different anions (aqueous and organicsolutions) and other high purity metal salts on request.
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Symbols2, 3-Butanedione monoxime .....................................................................................6
2-Hydroxyacetophenone ...........................................................................................5
2-Picoline borane .....................................................................................................1
4-Hydroxyacetophenone ...........................................................................................5
5-Ethyl-2-methylpyridine borane ..............................................................................1
9-Borabicyclo[3.3.1]nonane ......................................................................................3
(-)-Diisopinocampheylchloroborane ..........................................................................2(+)-Diisopinocampheylchloroborane .........................................................................2
(R)-Methyl oxazaborolidine ........................................................................................2
(S)-Methyl oxazaborolidine ........................................................................................2
BBis(pinacolato)diboron ..............................................................................................1
Borane tetrahydrofuran complex ...............................................................................1
Butylamine borane ....................................................................................................1
CCatecholborane......................................................................................................... 1
DDibutylboron triflate ..................................................................................................3
Dimethylamine borane ..............................................................................................1Dimethylsulfide borane .............................................................................................1
FFerric Chloride Solution .............................................................................................6
Ferric Sulfate Solution ...............................................................................................6
Ferrous Sulfate Solution ............................................................................................6
HHydroxylamine-O-sulfonic Acid .................................................................................6
LLithium Hexamethyldisilazane ...................................................................................5
Lithium triethylborohydride .......................................................................................2
Lithium tri-sec-butylborohydride ...............................................................................2
MMethoxydiethylborane ...............................................................................................3
NN-Hydroxyphtalimide ................................................................................................6
N,N-Diethylaniline borane .........................................................................................1
N, O,-Dimethylhydroxylamine Hydrochloride .............................................................6
OO-Benzylhydroxylamine Hydrochloride ......................................................................6
O-Methylhydroxylamine Hydrochloride ......................................................................6
PPhenyl Acetate ..........................................................................................................5
Pinacolborane ...........................................................................................................1
Potassium 3,7-Dimethyl-3-octylate ...........................................................................4
Potassium Ethylate ...................................................................................................4
Potassium Hexamethyldisilazane ..............................................................................5
Potassium Methylate.................................................................................................4
Potassium superoxide ...............................................................................................5Potassium tert.-Amylate............................................................................................4
Potassium tert.-Butylate ...........................................................................................4
Pyridine borane .........................................................................................................1
SSodium Ethylate ........................................................................................................4
Sodium Hexamethyldisilazane ...................................................................................5
Sodium Mentholate ...................................................................................................4
Sodium Methylate .....................................................................................................4
Sodium n-Butylate ....................................................................................................4
Sodium Potassium Alloy ............................................................................................5
Sodium tert.-Amylate ................................................................................................4
Sodium tert.-Butylate ................................................................................................4
Sodium triacetoxyborohydride ...................................................................................2Sodium tri-sec-butylborohydride ...............................................................................2
TTriethylamine borane ................................................................................................1
Triethylborane ...........................................................................................................3
Triethylborane-1,3-diaminopropane complex ............................................................3
Trimethoxyboroxin ....................................................................................................3
Trimethylboroxin .......................................................................................................3
Tri-n-butylborane ......................................................................................................3
Tri-n-butylborane-3-methoxypropylamine complex ....................................... ............3
Index
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While the descriptions, designs, data and information contained herein are presented in good faith and believed to be accurate, it is provided for your guidance only. Because many factors may affectprocessing or application/use, we recommend that you make tests to determine the suitability of a product for your particular purpose prior to use. NO WARRANTIES OF ANY KIND, EITHER EXPRESS ORIMPLIED, INCLUDING WARRANTIES OF MERCHANTABILITY OR FITNESS FOR A PARTICULAR PURPOSE, ARE MADE REGARDING PRODUCTS DESCRIBED OR DESIGNS, DATA OR INFORMATIONSET FORTH, OR THAT THE PRODUCTS, DESIGNS, DATA OR INFORMATION MAY BE USED WITHOUT INFRINGING THE INTELLECTUAL PROPERTY RIGHTS OF OTHERS. IN NO CASE SHALL THEDESCRIPTIONS, INFORMATION, DATA OR DESIGNS PROVIDED BE CONSIDERED A PART OF OUR TERMS AND CONDITIONS OF SALE.
Rev. 02/2013
BASF Corporation
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USA
Phone: +1-866-4BORANE or
+1-866-426-7263
Fax: +1-800-377-6797
Email: [email protected]
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Phone: +49 621 60-43942
Fax: +49 621 60-6643942
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Phone: +(852) 2731 3704
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