Life Science Intermediates for Organic Synthesis - BASF

Life Science Intermediates for Organic SynthesisProduct Overview

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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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1

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.

NameAbbreviation/ Trade Name Structure CAS#

Formula FW (g/mol) Form

Density (g/ml)

Bis(pinacolato)diboron PIN2B2 73183-34-3 C12

H24

B2O

4

253.94Powder

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.



Density (g/ml)

Borane tetrahydrofuran complex BTHF 14044-65-6 C4H

11BO

85.941M in THF 0.878

Dimethylsulfide borane complex DMSB 13292-87-0 C2H

9BS

75.9710M in DMS2M in THF

0.7940.865

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.



Density (g/ml)

2-Picoline borane PICB 3999-38-0 C7H

10BN

103.9530 wt% THF 0.909

5-Ethyl-2-methylpyridine borane PEMB 1006873-58-0 C8H

14BN

135.01Neat liquid 0.913

Dimethylamine borane DMAB 74-94-2 C2H

10BN

58.92Neat Solid 0.73 g/cc

N,N-Diethylaniline borane DEANB 13289-97-9 C10

H18

BN163.07

Neat liquid 0.921

Pyridine borane PYB 110-51-0 C5H

8BN


t-Butylamine borane TBAB 7337-45-3 C4H

14BN

86.97Powder 0.46 g/cc

(bulk)

Triethylamine borane TEAB 1722-26-5 C6H

18BN


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.



Density (g/ml)

(-)-Diisopinocampheylchloroborane (-)-DPC 85116-37-6 C20

H34

BCl320.80

60-65 wt% heptanes 0.855

(+)-Diisopinocampheylchloroborane (+)-DPC 112246-73-8 C20

H34

BCl320.80

60-65 wt% heptanes60-65 wt% hexanes

0.8550.890

(R)-Methyl oxazaborolidine (R)-MeCBS 112022-83-0 C18

H20

BNO277.17

1M in toluene 0.927

(S)-Methyl oxazaborolidine (S)-MeCBS 112022-81-8 C18

H20

BNO277.17

1M in toluene 0.927

Calselect® Reducing AgentsAlkali 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.



Density (g/ml)

Lithium triethylborohydride CALSELECT® LT 22560-16-3 C6H

16BLi

105.951M in THF 0.890

Lithium tri-sec-butylborohydride CALSELECT® Li 38721-52-7 C12

H28

BLi190.11

1M in THF 0.898

Sodium triacetoxyborohydride CALSELECT® STAB 56553-60-7 C6H

10BNaO

6

211.96PowderGranular

0.765 g/cc (bulk)

Sodium tri-sec-butylborohydride CALSELECT® Na 67276-04-4 C12

H28

BNa206.15

1M in THF 0.898

2

AlkylboranesAlkylboranes 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.



Density (g/ml)

9-Borabicyclo[3.3.1]nonane 9BBN 280-64-8 C8H

15B

122.020.5M in THF 0.882

Dibutylboron triflate DBBT 60669-69-4 C9H

18BF

3O

3S

274.151M in toluene 0.903

Methoxydiethylborane MDEB 7397-46-8 C5H

13BO

99.97Neat liquid50 wt% in THF

0.7490.807

Triethylborane TEB 97-94-9 C6H

15B

98.00Neat liquid14 wt% in THF

0.6960.848

Triethylborane-1,3-diaminopropane complex TEB-DAP 148861-07-8 C9H

25BN

2


Tri-n-butylborane TNBB 122-56-5 C12

H27

B182.16

Neat liquid 0.748

Tri-n-butylborane-3-methoxypropylamine complex TnBB-MOPA 345269-15-0 C15

H37

BN2


Boroxins and Borates



Density (g/ml)

Trimethoxyboroxin TMBX 102-24-9 C3H

9B

3O

6


Trimethylboroxin MBX 823-96-1 C3H

9B

3O

3

125.5350 wt% in THF 0.894

3

Alkali Metal AlcoholatesAlcoholates 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/SynonymAbbreviation/ Trade Name Structure CAS #

Formula FW (g/mol) Forms

Density (g/ml)

Potassium 3,7-Dimethyl-3-octylatePotassium 3,7-Dimethyl-3-octanoxide

KDMO/Heptane 50% 263148-42-1 C10

H21

KO196.37

50% w/w in n-heptane

0.804

Potassium EthylatePotassium Ethoxide

KE 24%(DN with toluene)

917-58-8 C2H

5KO

84.1424% w/w in ethanol 0.895

Potassium MethylatePotassium Methoxide

KMKM 32% KOMe

865-33-8 CH3KO

70.14Powder32% w/w in methanol

0.978

Potassium tert.-AmylatePotassium tert.-Pentoxide

KTAKTA/Cyclohexane 15%

KTA/Toluene 25%

KTA/THF 45%

41233-93-6 C5H

11KO

126.20Powder

15% w/w in cyclohexane25% w/w in toluene

45% w/w in THF

0.57 g/cc (Bulk)

0.801

0.904

0.951 @ 21˚C

Potassium tert.-ButylatePotassium tert-Butoxide

KTBKTB/TBA 15%

KTB/THF 20%

KTB/TBA 13.7% with THF

865-47-4 C4H

9KO

112.21Powder

15% w/w in tert.-butanol20% w/w in THF

13.7% w/w in TBA with THF

0.813

0.818

0.906

0.838 @ 25˚C

Sodium Alcoholates



Density (g/ml)

Sodium EthylateSodium Ethoxide

SESE 21%

141-52-6 C2H

5NaO

68.05Powder21% w/w in ethanol 0.880

Sodium Mentholate NaM/Hexanes 50% 19321-38-1 C10

H19

NaO178.25

50% w/w in hexanes 0.815

Sodium MethylateSodium Methoxide

SMSMS 25%

SMS 30%NaOMe

124-41-4 CH3NaO

54.03Powder25% w/w in methanol30% w/w in methanol

0.944

0.969

Sodium n-ButylateSodium n-Butoxide

SNB/NBA 19% 2372-45-4 C4H

9NaO

96.119% w/w in n-butanol

0.853

Sodium tert.-AmylateSodium tert.-Pentoxide

STASTA/Hexanes 38%

STA/THF 35%STA/Toluene 25%

14593-46-5 C5H

11NaO

110.13Powder38% w/w in hexanes

35% w/w in THF25% w/w in toluene

0.752

0.9260.885

Sodium tert.-ButylateSodium tert.-Butoxide

STB 865-48-5 C4H

9NaO

96.02Powder 0.698 g/cc

(Bulk)

4

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.



Density (g/ml)

Potassium HexamethyldisilazanePotassium bi(trimethylsily)amide

KHMDS/THF 20%KHMDS/Toluene 15%

40949-94-8 C6H

18KNSi

2

199.520% w/w in THF15% w/w in toluene

0.8980.879

Lithium HexamethyldisilazaneLithium bi(trimethylsily)amide

LiHMDS/THF 24% 4039-32-1 C6H

18LiNSi

2

167.3324% w/w in THF 0.867

Sodium HexamethyldisilazaneSodium bis(trimethylsilyl)amide

NaHMDS/THF 40%NaHMDS/Toluene 13%

1070-89-9 C6H

18NNaSi

2

183.3840% w/w in THF13% w/w in toluene

0.8890.868 @ 21.0 ˚C

Other Alkali Metal CompoundsSodium-Potassium Alloy (NaK), essentially a liquid form of Potassium metal, is mainly used for reductions and as a raw material for making potassium derivatives. Potassium superoxide (KO2) has its main applications as a chemical oxygen source.



Density (g/ml)

Potassium Superoxide KO2 CAT

KO2 UNCAT

KO2 UNCAT fluff

KO2

12030-88-5 KO2

Catalyzed granulesUncatalyzed granulesUncatalyzed 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/SynonymAbbreviation/ Trade Name Structure CAS No.


Density (g/ml)

2-Hydroxyacetophenone 2-HAPOrtho-Hydroxyacetophenone

118-93-4 C8H

8O

2

136.15Liquid 1.157

Bulk

4-Hydroxyacetophenone 4-HAP1-(4-Hydroxyphenyl)ethanonep-Hydroxyacetophenonep-Hydroxyphenyl methyl ketone

99-93-4 C8H

8O

2

136.15Powder 1.157

Bulk

Phenyl Acetate PhOAc 122-79-2 C7H

14O

2

130.2Liquid 0.875-

0.877

5

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.



Density (g/ml)

Hydroxylamine-O-sulfonic Acid HOSA 2950-43-8 H3NO

4S

113.09Solid 2.2 g/cc

O-Benzylhydroxylamine HydrochlorideO-Benzyhydroxylammonium Chloride

OBHA•HCl 2687-43-6 C7H

10ClNO

159.62Solid .370 g/cc

O-Methylhydroxylamine HydrochlorideO-Methylhydroxylammonium Chloride

O-MHA•HCl 593-56-6 CH6ClNO

83.5230% Solution 1.15 g/ml

N,O-Dimethylhydroxylamine HydrochlorideN,O-Dimethylhydroxylammonium Chloride

NODMHA•HCl 6638-79-5 C2H

8ClNO

97.54Solid

N-Hydroxyphtalimide NHPI 524-38-9 C8H

5NO

3

163.13Solid

2, 3-Butanedione monoxime BDMO 57-71-6 C4H

7NO

2

101.11Solid

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.



Density (g/ml)

Ferric Chloride Solution High Purity

Iron(III) Chloride Solution

7705-08-0 FeCl3

162.2012% Solution (Fe3+) 1.36 g/ml

Ferric Sulfate SolutionHigh Purity

Iron(III) Sulfate Solution

10028-20-5 Fe2(SO

4)3

399.8812% Solution (Fe3+) 1.50 g/ml

Ferrous Sulfate SolutionHigh Purity

Iron(II) Sulfate Solution

7720-78-7 FeSO4

151.919% Solution

BASF offers a large variety of different anions (aqueous and organic solutions) and other high purity metal salts on request.

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Symbols2, 3-Butanedione monoxime .....................................................................................62-Hydroxyacetophenone ...........................................................................................52-Picoline borane .....................................................................................................14-Hydroxyacetophenone ...........................................................................................55-Ethyl-2-methylpyridine borane ..............................................................................19-Borabicyclo[3.3.1]nonane ......................................................................................3(-)-Diisopinocampheylchloroborane ..........................................................................2(+)-Diisopinocampheylchloroborane .........................................................................2(R)-Methyl oxazaborolidine ........................................................................................2(S)-Methyl oxazaborolidine ........................................................................................2

BBis(pinacolato)diboron ..............................................................................................1Borane tetrahydrofuran complex ...............................................................................1Butylamine borane ....................................................................................................1

CCatecholborane.........................................................................................................1

DDibutylboron triflate ..................................................................................................3Dimethylamine borane ..............................................................................................1Dimethylsulfide borane .............................................................................................1

FFerric Chloride Solution .............................................................................................6Ferric Sulfate Solution ...............................................................................................6Ferrous Sulfate Solution ............................................................................................6

HHydroxylamine-O-sulfonic Acid .................................................................................6

LLithium Hexamethyldisilazane ...................................................................................5Lithium triethylborohydride .......................................................................................2Lithium tri-sec-butylborohydride ...............................................................................2

MMethoxydiethylborane ...............................................................................................3

NN-Hydroxyphtalimide ................................................................................................6N,N-Diethylaniline borane .........................................................................................1N, O,-Dimethylhydroxylamine Hydrochloride .............................................................6

OO-Benzylhydroxylamine Hydrochloride ......................................................................6O-Methylhydroxylamine Hydrochloride ......................................................................6

PPhenyl Acetate ..........................................................................................................5Pinacolborane ...........................................................................................................1Potassium 3,7-Dimethyl-3-octylate ...........................................................................4Potassium Ethylate ...................................................................................................4Potassium Hexamethyldisilazane ..............................................................................5Potassium Methylate.................................................................................................4Potassium superoxide ...............................................................................................5Potassium tert.-Amylate............................................................................................4Potassium tert.-Butylate ...........................................................................................4Pyridine borane .........................................................................................................1

SSodium Ethylate ........................................................................................................4Sodium Hexamethyldisilazane ...................................................................................5Sodium Mentholate ...................................................................................................4Sodium Methylate .....................................................................................................4Sodium n-Butylate ....................................................................................................4Sodium Potassium Alloy ............................................................................................5Sodium tert.-Amylate ................................................................................................4Sodium tert.-Butylate ................................................................................................4Sodium triacetoxyborohydride ...................................................................................2Sodium tri-sec-butylborohydride ...............................................................................2

TTriethylamine borane ................................................................................................1Triethylborane ...........................................................................................................3Triethylborane-1,3-diaminopropane complex ............................................................3Trimethoxyboroxin ....................................................................................................3Trimethylboroxin .......................................................................................................3Tri-n-butylborane ......................................................................................................3Tri-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 affect processing 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 OR IMPLIED, INCLUDING WARRANTIES OF MERCHANTABILITY OR FITNESS FOR A PARTICULAR PURPOSE, ARE MADE REGARDING PRODUCTS DESCRIBED OR DESIGNS, DATA OR INFORMATION SET FORTH, OR THAT THE PRODUCTS, DESIGNS, DATA OR INFORMATION MAY BE USED WITHOUT INFRINGING THE INTELLECTUAL PROPERTY RIGHTS OF OTHERS. IN NO CASE SHALL THE DESCRIPTIONS, INFORMATION, DATA OR DESIGNS PROVIDED BE CONSIDERED A PART OF OUR TERMS AND CONDITIONS OF SALE.

Rev. 02/2013

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Life Science Intermediates for Organic Synthesis - BASF