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
• Article Data: 21

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

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

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 
• 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 
• 1089174-30-0 (2S,3S,6S,7S,2'R)-(-)-ethyl-2-azido-3-(2'-bromopropanamido)-9-(tert-butyldiphenylsilyloxy)-6,7-O-isopropylidenenonanoate 
• 40781-39-3 (S)-(-)-2-bromo-N-phenylpropanamide 
• 1426696-41-4 (2R)-2-(3-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}azetidin-1-yl)-N-methylpropanamide trifluoroacetate 
• 885126-83-0 (S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanoic acid 

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