10009-70-8

Basic information

• Product Name: (R)-(+)-2-BROMOPROPIONIC ACID
• Synonyms: PROPANOIC ACID, 2-BROMO-, (2R)-;(R)-(+)-2-BROMOPROPIONIC ACID;(R)-(+)-2-Bromopropionic acid, >85% ee, 99%;2-R-(+) bromopropionic acid;(R)-(+)-2-Bromopropionic acid, GC 98%;(R)-(+)-2-BROMOPROPIONIC ACID 98+%;(R)-(+)-2-Bromopropionic acid, 99%, ee:>85%;(R)-2-Bromopropanoic acid
• CAS NO: 10009-70-8
• Molecular Formula: C₃H₅BrO₂
• Molecular Weight: 152.97
• Product Categories: Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Carboxylic Acids;Chiral Building Blocks;Organic Building Blocks
• Mol File: 10009-70-8.mol

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 203 °C
• Flash Point: 100 °C
• Appearance: /
• Density: 1.692 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.12mmHg at 25°C
• Refractive Index: n20/D 1.475
• Storage Temp.: 2-8°C
• PKA: 3.00±0.10(Predicted)
• BRN: 1720262
• CAS DataBase Reference: (R)-(+)-2-BROMOPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2-BROMOPROPIONIC ACID(10009-70-8)
• EPA Substance Registry System: (R)-(+)-2-BROMOPROPIONIC ACID(10009-70-8)

Safety Data

• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• F: 10
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 10009-70-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light brown liquid

Purification Methods

Dissolve it in Et2O, dry (CaCl2), evaporate and distil it through a short column. Distillation through a Podbielniak column (p 11) (see S-(-)-2-chloropropionic acid below) led to decomposition. Store it in the dark under N2, preferably in sealed ampoules. Even at -10o it slowly decomposes. [Fuet et al. J Am Chem Soc 76 6054 1954, Beilstein 2 IV 761.]

InChI:InChI=1/C3H5BrO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)/t2-/m1/s1

Synthetic route

D-Alanine (338-69-2) → R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With hydrogen bromide; potassium bromide; sodium nitrite at 0 - 5℃; for 1h;	95%
With hydrogen bromide; potassium bromide; sodium nitrite In water at -15 - 20℃; Inert atmosphere;	82%
With sulfuric acid; potassium bromide; sodium nitrite at 0 - 20℃; for 2h;	41%

(S)-2-(methylsulfonyloxy)propionic acid (66423-08-3) → R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
Stage #1: (S)-2-(methylsulfonyloxy)propionic acid With lithium bromide In toluene at 60℃; for 1h; Stage #2: In water; toluene at 20℃; for 0.5h;	45%

L-alanin (56-41-7) → R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With nitrosyl bromide
Stage #1: L-alanin With sulfuric acid; potassium bromide In water; toluene Stage #2: With sodium nitrite In water; toluene at -10℃; for 18h;	n/a
Stage #1: L-alanin With sulfuric acid; potassium bromide In water Stage #2: With sodium nitrite In water at -10℃; for 18h; Stage #3: In water; toluene	n/a

(2R)-methyl 2-bromopropionate (20047-41-0) → R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With potassium hydroxide

2-Bromopropionic acid (598-72-1) → R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With Cinchonin

2-Bromopropionic acid (598-72-1) + Cinchonin (118-10-5) → (S)-2-bromopropanoic acid (32644-15-8) + R-(+)-2-bromopropionic acid (10009-70-8)

1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl α-bromopropionate (167823-32-7) → (S)-2-bromopropanoic acid (32644-15-8) + R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran for 0.5h; Yields of byproduct given. Title compound not separated from byproducts;

2-Bromo-propionic acid (S)-4,4-dimethyl-2-oxo-1-phenyl-pyrrolidin-3-yl ester → (S)-2-bromopropanoic acid (32644-15-8) + R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With lithium hydroxide In tetrahydrofuran a) -20 deg C, 2 h, b) -15 deg C, 4 h; Title compound not separated from byproducts;

L-Lactic acid (79-33-4) + phosphorus pentabromide (7789-69-7) → R-(+)-2-bromopropionic acid (10009-70-8)

(2R)-methyl 2-bromopropionate (20047-41-0) + aqueous KOH → R-(+)-2-bromopropionic acid (10009-70-8)

dl-α-bromo-propionic acid → R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With Cinchonin

DL-<2-bromo-propionyl>-glycylglycine → R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With Quinine saure Hydrolyse des erhaltenen D(+)-<2-Brom-propionyl>-glycylglycins;

ester of/the/ d-lactic acid → R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With phosphorus pentabromide; benzene Es entstehen die Ester;
With chloroform; phosphorus pentabromide Es entstehen die Ester;

Cinchonin (118-10-5) + inactive α-bromo-propionic acid → R-(+)-2-bromopropionic acid (10009-70-8)

bromo-methyl-ketene (29264-45-7) → (S)-2-bromopropanoic acid (32644-15-8) + R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
Stage #1: bromo-methyl-ketene With n-butyllithium; diethylzinc; (S)-3-hydroxytetyrahydrofurane In hexane; toluene at -78 - 0℃; for 13h; Stage #2: With hydrogenchloride In tetrahydrofuran at 20℃; for 48h; Title compound not separated from byproducts;

C9H21BrO2Si2 → (S)-2-bromopropanoic acid (32644-15-8) + R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; 2.6-dimethylphenol; C32H12BF24(1-)*C44H30N2O2P(1+) In toluene at -40℃; for 24h; Inert atmosphere; Overall yield = 87 %; enantioselective reaction;

2-Bromopropionic acid (598-72-1) → (S)-2-bromopropanoic acid (32644-15-8) + R-(+)-2-bromopropionic acid (10009-70-8)

Conditions	Yield
With Ν,Ν-dimethyldehydroabietylamine In chloroform-d1 at 27℃; Resolution of racemate;

R-(+)-2-bromopropionic acid (10009-70-8) + 4-aminobenzamide (2835-68-9) → 4-{[(2R)-2-bromopropanoyl]amino}benzamide

Conditions	Yield
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 20℃; for 0.5h; Inert atmosphere;	100%
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 20℃; for 0.5h; Inert atmosphere;	100%

styrene (292638-84-7) + R-(+)-2-bromopropionic acid (10009-70-8) → 2-iodo-1-phenylethyl (2R)-2-bromopropanoate

Conditions	Yield
With N-iodo-succinimide In dichloromethane at 20 - 22℃; for 0.25h; regioselective reaction;	99%

R-(+)-2-bromopropionic acid (10009-70-8) → (R)-2-bromo-propan-1-ol (16088-61-2)

Conditions	Yield
With borane-THF In tetrahydrofuran at 0℃; for 3h;	98%

R-(+)-2-bromopropionic acid (10009-70-8) + (2S,3S,6R,7S)-(-)-ethyl-3-amino-2-azido-9-(tert-butyldiphenylsiloxy)-6,7-O-isopropylidenenonanoate (1089173-91-0) → (2S,3S,6R,7S,2'R)-(-)-ethyl-2-azido-3-(2'-bromopropanamido)-9-(tert-butyldiphenylsilyloxy)-6,7-O-isopropylidenenonanoate (1089174-21-9)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	95%

R-(+)-2-bromopropionic acid (10009-70-8) + (2S,3S,6S,7S)-(-)-ethyl-3-amino-2-azido-9-(tert-butyldiphenylsiloxy)-6,7-O-isopropylidenenonanoate (1089174-29-7) → (2S,3S,6S,7S,2'R)-(-)-ethyl-2-azido-3-(2'-bromopropanamido)-9-(tert-butyldiphenylsilyloxy)-6,7-O-isopropylidenenonanoate (1089174-30-0)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;	95%

4-n-Propylphenol (645-56-7) + R-(+)-2-bromopropionic acid (10009-70-8) → (R)-2-(4-propyl-phenoxy)-propanoic acid

Conditions	Yield
Stage #1: 4-n-Propylphenol; R-(+)-2-bromopropionic acid With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 5h; Stage #2: With sodium hydroxide In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; water; mineral oil pH=1;	94%

diazomethane (186581-53-3, 908094-01-9) + R-(+)-2-bromopropionic acid (10009-70-8) → (2R)-methyl 2-bromopropionate (20047-41-0)

Conditions	Yield
In diethyl ether	93%

R-(+)-2-bromopropionic acid (10009-70-8) + 2-methylpropan-2-thiol (75-66-1) → (2S)-2-(tert-butylthio)propanoic acid

Conditions	Yield
In ethanol	92%

R-(+)-2-bromopropionic acid (10009-70-8) + (2''R,3''S)-(+)-tert-butyl-{N'-[3''-amino-2''-(o-nitrobenzenesulfonamido)heptanoyl]-L-alanyl}-L-valinate → (2''R,3''S,2'''R)-(-)-tert-butyl-{N'-[3''-(2'''-bromopropanamido)-2''-(o-nitrobenzenesulfonamido)heptanoyl]-L-alanyl}-L-valinate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 1h; Inert atmosphere;	91%

R-(+)-2-bromopropionic acid (10009-70-8) + (2S,3S)-N-[(1S)-2-(tert-Butyldiphenylsilyloxy)-1-methylethyl]-3-azido-4-phenyl-2-(triethylsilyloxy)butylamine (191217-13-7) → (R)-N-((2S,3S)-3-Azido-4-phenyl-2-triethylsilanyloxy-butyl)-2-bromo-N-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-propionamide (191217-14-8)

Conditions	Yield
With diisopropyl-carbodiimide In dichloromethane at 0℃; for 3h;	90%
With dacarbazine In dichloromethane at 0℃; for 4h; Acylation;

5-bromo-1H-indole (10075-50-0) + R-(+)-2-bromopropionic acid (10009-70-8) → (2S)-2-(5-bromo-1H-indol-1-yl)propanoic acid

Conditions	Yield
Stage #1: 5-bromo-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at -10℃; for 0.75h; Stage #2: R-(+)-2-bromopropionic acid In N,N-dimethyl-formamide; mineral oil at -10 - 20℃; for 3h;	89%

p-cresol (106-44-5) + R-(+)-2-bromopropionic acid (10009-70-8) → (R)-2-(4-methylphenoxy)propanoic acid (14013-55-9)

Conditions	Yield
Stage #1: p-cresol; R-(+)-2-bromopropionic acid With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 5h; Stage #2: With sodium hydroxide In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; water; mineral oil pH=1;	85%

R-(+)-2-bromopropionic acid (10009-70-8) + benzyl alcohol (100-51-6) → (R)-2-bromopropionic acid benzyl ester

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 18h; Reflux;	82%
In neat (no solvent) at 20℃; for 84h; Inert atmosphere;	47%
toluene-4-sulfonic acid

R-(+)-2-bromopropionic acid (10009-70-8) + 4-aminoadamantan-1-ol (75375-89-2) → Z-(R)-2-bromo-N-(5-hydroxyadamantan-2-yl)-propionamide + E-(R)-2-bromo-N-(5-hydroxyadamantan-2-yl)-propionamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	A n/a B 81%

R-(+)-2-bromopropionic acid (10009-70-8) → (R)-2-bromopropionyl chloride (7148-74-5, 22592-73-0, 71425-59-7, 52152-04-2)

Conditions	Yield
With thionyl chloride for 6h; Heating;	80%
With thionyl chloride
With thionyl chloride In diethyl ether at 0℃; for 1h;

R-(+)-2-bromopropionic acid (10009-70-8) + 2-chloro-4-methyl-benzenamine (615-65-6) → (R)-2-bromo-N-(2-chloro-4-methylphenyl)propanamide (1429642-80-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20 - 24℃; for 4.5h; Cooling with ice;	80%

R-(+)-2-bromopropionic acid (10009-70-8) + (2E,4S,2'S)-4-[(2'-amino-3',3'-dimethylbutyryl)methylamino]-2,5-dimethylhex-2-enoic acid ethyl ester (187345-38-6) → C20H35BrN2O4

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 2h;	76%

R-(+)-2-bromopropionic acid (10009-70-8) + (2R,3S)-2-vinyltetrahydro-2H-pyran-3-ol (101208-75-7) → C10H16O4 (1243724-79-9)

Conditions	Yield
With sodium hydride In 1,4-dioxane	69%

R-(+)-2-bromopropionic acid (10009-70-8) + bis(2-methoxyphenyl)methanamine → N-(bis(2-methoxyphenyl)methyl)-2-bromopropanamide

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 20h; Inert atmosphere;	66%

R-(+)-2-bromopropionic acid (10009-70-8) + (R)-1-(4-methoxyphenyl)ethylamine (6298-96-0, 22038-86-4, 35600-82-9, 41851-59-6) → (R,R)-2-bromo-N--1-(4-methoxyphenylethyl)propanamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;	66%

R-(+)-2-bromopropionic acid (10009-70-8) + t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2) → (2S)-2-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]propanoic acid (952486-63-4)

Conditions	Yield
Stage #1: t-butyl 4-hydroxy piperidine-1-carboxylate With sodium hydride In 1,4-dioxane at 0℃; for 0.5h; Inert atmosphere; Stage #2: R-(+)-2-bromopropionic acid In 1,4-dioxane at 25℃; for 40h; Inert atmosphere;	65%
With sodium hydride In 1,4-dioxane for 22.5h;

7-hydroxy-4-methyl-chromen-2-one (90-33-5, 79566-13-5) + R-(+)-2-bromopropionic acid (10009-70-8) → (S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanoic acid (885126-83-0)

Conditions	Yield
With potassium carbonate In acetone at 56℃; for 13h;	65%

(1S)-1-(4-chlorophenylmethyl)-2-hydroxyethylamine (201864-00-8) + R-(+)-2-bromopropionic acid (10009-70-8) → (R)-2-bromo-N-((S)-1-(4-chlorophenyl)-3-hydroxypropan-2-yl)propanamide

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1.5h;	64%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3h;	64%

homoalylic alcohol (627-27-0) + R-(+)-2-bromopropionic acid (10009-70-8) → C7H12O3 (1243724-72-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 20h; Reflux;	53%

R-(+)-2-bromopropionic acid (10009-70-8) + S-(5'-adenosyl)-L-homocysteine (979-92-0) → (S)-carboxy-S-adenosyl-ethionine

Conditions	Yield
With ammonium bicarbonate at 37℃; for 18h;	50%

R-(+)-2-bromopropionic acid (10009-70-8) → R,S-2,2'-(hydroxyimino)dipropionic acid (195453-23-7)

Conditions	Yield
With sodium hydroxide; hydroxylamine hydrochloride In water at 30 - 35℃; for 40h; pH=7.2;	49%

R-(+)-2-bromopropionic acid (10009-70-8) + (R)-1,1,1-trichloropent-4-en-2-ol (1421739-59-4) → (R)-1,1,1-trichloropent-4-en-2-yl (R’)-2-bromopropanoate (1421739-53-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 1h; Steglich Esterification; Inert atmosphere;	44%

R-(+)-2-bromopropionic acid (10009-70-8) + aminopropane diethyl acetal (41365-75-7) + p-toluenesulfonyl chloride (98-59-9) + N-(9-fluorenylmethoxycarbonyl)-2-aminoethanol (105496-31-9) → C19H31N2O6PolS

Conditions	Yield
Stage #1: N-(9-fluorenylmethoxycarbonyl)-2-aminoethanol With boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 0.5h; Wang resin; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.25h; Wang resin; Stage #3: R-(+)-2-bromopropionic acid; aminopropane diethyl acetal; p-toluenesulfonyl chloride diastereoselective reaction; Further stages;	44%

Upstream product

• 56-41-7 L-alanin 
• 338-69-2 D-Alanine 
• 20047-41-0 (2R)-methyl 2-bromopropionate 
• 598-72-1 2-Bromopropionic acid 
• 118-10-5 Cinchonin 
• 79-33-4 L-Lactic acid 
• 7789-69-7 phosphorus pentabromide 
• 29264-45-7 bromo-methyl-ketene 
• 66423-08-3 (S)-2-(methylsulfonyloxy)propionic acid 
• 167823-32-7 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl α-bromopropionate 

Downstream Products

• 92283-80-2 (2S,2'S)-2,2'-Iminobis(propionsaeure) 
• 31654-38-3 N-(2-bromo-propionyl)-alanine 
• 63358-47-4 (S),(S)-octopine 
• 79-33-4 L-Lactic acid 
• 10326-41-7 D-Lactic acid 
• 7148-74-5 (R)-2-bromopropionyl chloride 
• 3913-67-5 N-methylalanine 
• 54837-16-0 (S)-N-benzyloxy-alanine 
• 124251-97-4 (S)-2-(2-Benzyloxy-ethoxy)-propionic acid 
• 141047-82-7 2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-propionic acid 
• 191217-14-8 (R)-N-((2S,3S)-3-Azido-4-phenyl-2-triethylsilanyloxy-butyl)-2-bromo-N-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-propionamide 
• 687-47-8 (S)-Ethyl lactate 
• 7699-00-5 (R)-Ethyl lactate 
• 1129-46-0 (R)-(+)-2-phenoxypropionic acid 

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Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Bronsted acid catalysis

Highly enantioselective protonation of α-halo and alkoxy carboxylic acid-derived ketene disilyl acetals is achieved by using P-spiro chiral diaminodioxaphosphonium barfate as a Bronsted acid catalyst, where the enantiofacial discrimination by the catalyst mainly stems from the recognition of the electronic difference between two substituents on the ketene disilyl acetal.

PROCESS FOR PRODUCING OPTICALLY ACTIVE 2-SUBSTITUTED CARBOXYLIC ACID

The present invention relates to a process for efficiently producing an optically active 2-bromocarboxylic acid and an optically active 2-sulfonyloxycarboxylic acid, which are important in the production of medicinal compounds and so forth. An optically active 2-sulfonyloxycarboxylic acid ester is subjected to deprotection under acid conditions to obtain an optically active 2-sulfonyloxycarboxylic acid. A metal bromide is caused to act on the acid to brominate it with configuration inversion at position 2 to thereby produce an optically active 2-bromocarboxylic acid. The resultant optically active 2-bromocarboxylic acid is isolated/purified by subjecting it to a step in which the acid is crystallized and separated as a salt with a base. Thus, an optically active 2-bromocarboxylic acid having a high chemical purity and high optical purity can be produced.