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10009-70-8

Basic Information
CAS No.: 10009-70-8
Name: Propanoic acid,2-bromo-, (2R)-
Molecular Structure:
Molecular Structure of 10009-70-8 (Propanoic acid,2-bromo-, (2R)-)
Formula: C3H5 Br O2
Molecular Weight: 152.97
Synonyms: Propanoicacid, 2-bromo-, (R)-; Propionic acid, 2-bromo-, D- (8CI); (+)-2-Bromopropanoicacid; (+)-2-Bromopropionic acid; (+)-a-Bromopropanoic acid; (2R)-2-Bromopropanoic acid;(2R)-2-Bromopropanoic acid; (2R)-2-Bromopropionic acid;(R)-(+)-2-Bromopropionic acid; (R)-2-Bromopropanoic acid; (R)-2-Bromopropanoicacid; (R)-2-Bromopropionic acid; (R)-a-Bromopropionic acid; D-2-Bromopropionic acid
EINECS:
Density: 1.692 g/mL at 20 °C(lit.)
Melting Point: 25°C
Boiling Point: 203 °C
Flash Point: 100 °C
Solubility:
Appearance:
Hazard Symbols:
Risk Codes: 22-34
Safety:
Hazard Codes C
Risk Statements 22-34
Safety Statements 26-36/37/39-45
RIDADR UN 3265 8/PG 3
WGK Germany 3
10
HazardClass 8
PackingGroup III
Transport Information:
PSA: 37.30000
LogP: 0.85440
Synthetic route
338-69-2

D-Alanine

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
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%
66423-08-3

(S)-2-(methylsulfonyloxy)propionic acid

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
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%
56-41-7

L-alanin

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
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
20047-41-0

(2R)-methyl 2-bromopropionate

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
With potassium hydroxide
598-72-1

2-Bromopropionic acid

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
With Cinchonin
598-72-1

2-Bromopropionic acid

118-10-5

Cinchonin

A

32644-15-8

(S)-2-bromopropanoic acid

B

10009-70-8

R-(+)-2-bromopropionic acid

167823-32-7

1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-O-yl α-bromopropionate

A

32644-15-8

(S)-2-bromopropanoic acid

B

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
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

A

32644-15-8

(S)-2-bromopropanoic acid

B

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran a) -20 deg C, 2 h, b) -15 deg C, 4 h; Title compound not separated from byproducts;
79-33-4

L-Lactic acid

7789-69-7

phosphorus pentabromide

10009-70-8

R-(+)-2-bromopropionic acid

20047-41-0

(2R)-methyl 2-bromopropionate

aqueous KOH

aqueous KOH

10009-70-8

R-(+)-2-bromopropionic acid

dl-α-bromo-propionic acid

dl-α-bromo-propionic acid

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
With Cinchonin
DL-<2-bromo-propionyl>-glycylglycine

DL-<2-bromo-propionyl>-glycylglycine

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
With Quinine saure Hydrolyse des erhaltenen D(+)-<2-Brom-propionyl>-glycylglycins;
ester of/the/ d-lactic acid

ester of/the/ d-lactic acid

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
With phosphorus pentabromide; benzene Es entstehen die Ester;
With chloroform; phosphorus pentabromide Es entstehen die Ester;
118-10-5

Cinchonin

inactive α-bromo-propionic acid

inactive α-bromo-propionic acid

10009-70-8

R-(+)-2-bromopropionic acid

29264-45-7

bromo-methyl-ketene

A

32644-15-8

(S)-2-bromopropanoic acid

B

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
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

A

32644-15-8

(S)-2-bromopropanoic acid

B

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
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;
598-72-1

2-Bromopropionic acid

A

32644-15-8

(S)-2-bromopropanoic acid

B

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
With Ν,Ν-dimethyldehydroabietylamine In chloroform-d1 at 27℃; Resolution of racemate;
10009-70-8

R-(+)-2-bromopropionic acid

2835-68-9

4-aminobenzamide

4-{[(2R)-2-bromopropanoyl]amino}benzamide

Conditions
ConditionsYield
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%
10009-70-8

R-(+)-2-bromopropionic acid

2-iodo-1-phenylethyl (2R)-2-bromopropanoate

Conditions
ConditionsYield
With N-iodo-succinimide In dichloromethane at 20 - 22℃; for 0.25h; regioselective reaction;99%
10009-70-8

R-(+)-2-bromopropionic acid

16088-61-2

(R)-2-bromo-propan-1-ol

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at 0℃; for 3h;98%
10009-70-8

R-(+)-2-bromopropionic acid

1089173-91-0

(2S,3S,6R,7S)-(-)-ethyl-3-amino-2-azido-9-(tert-butyldiphenylsiloxy)-6,7-O-isopropylidenenonanoate

1089174-21-9

(2S,3S,6R,7S,2'R)-(-)-ethyl-2-azido-3-(2'-bromopropanamido)-9-(tert-butyldiphenylsilyloxy)-6,7-O-isopropylidenenonanoate

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;95%
10009-70-8

R-(+)-2-bromopropionic acid

1089174-29-7

(2S,3S,6S,7S)-(-)-ethyl-3-amino-2-azido-9-(tert-butyldiphenylsiloxy)-6,7-O-isopropylidenenonanoate

1089174-30-0

(2S,3S,6S,7S,2'R)-(-)-ethyl-2-azido-3-(2'-bromopropanamido)-9-(tert-butyldiphenylsilyloxy)-6,7-O-isopropylidenenonanoate

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;95%
645-56-7

4-n-Propylphenol

10009-70-8

R-(+)-2-bromopropionic acid

(R)-2-(4-propyl-phenoxy)-propanoic acid

Conditions
ConditionsYield
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%
10009-70-8

R-(+)-2-bromopropionic acid

20047-41-0

(2R)-methyl 2-bromopropionate

Conditions
ConditionsYield
In diethyl ether93%
10009-70-8

R-(+)-2-bromopropionic acid

75-66-1

2-methylpropan-2-thiol

(2S)-2-(tert-butylthio)propanoic acid

Conditions
ConditionsYield
In ethanol92%
10009-70-8

R-(+)-2-bromopropionic acid

(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
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 1h; Inert atmosphere;91%
10009-70-8

R-(+)-2-bromopropionic acid

191217-13-7

(2S,3S)-N-[(1S)-2-(tert-Butyldiphenylsilyloxy)-1-methylethyl]-3-azido-4-phenyl-2-(triethylsilyloxy)butylamine

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

Conditions
ConditionsYield
With diisopropyl-carbodiimide In dichloromethane at 0℃; for 3h;90%
With dacarbazine In dichloromethane at 0℃; for 4h; Acylation;
10075-50-0

5-bromo-1H-indole

10009-70-8

R-(+)-2-bromopropionic acid

(2S)-2-(5-bromo-1H-indol-1-yl)propanoic acid

Conditions
ConditionsYield
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%
106-44-5

p-cresol

10009-70-8

R-(+)-2-bromopropionic acid

14013-55-9

(R)-2-(4-methylphenoxy)propanoic acid

Conditions
ConditionsYield
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%
10009-70-8

R-(+)-2-bromopropionic acid

100-51-6

benzyl alcohol

(R)-2-bromopropionic acid benzyl ester

Conditions
ConditionsYield
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
10009-70-8

R-(+)-2-bromopropionic acid

75375-89-2

4-aminoadamantan-1-ol

A

Z-(R)-2-bromo-N-(5-hydroxyadamantan-2-yl)-propionamide

B

E-(R)-2-bromo-N-(5-hydroxyadamantan-2-yl)-propionamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;A n/a
B 81%
10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
With thionyl chloride for 6h; Heating;80%
With thionyl chloride
With thionyl chloride In diethyl ether at 0℃; for 1h;
10009-70-8

R-(+)-2-bromopropionic acid

615-65-6

2-chloro-4-methyl-benzenamine

1429642-80-7

(R)-2-bromo-N-(2-chloro-4-methylphenyl)propanamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20 - 24℃; for 4.5h; Cooling with ice;80%
10009-70-8

R-(+)-2-bromopropionic acid

187345-38-6

(2E,4S,2'S)-4-[(2'-amino-3',3'-dimethylbutyryl)methylamino]-2,5-dimethylhex-2-enoic acid ethyl ester

C20H35BrN2O4

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 2h;76%
10009-70-8

R-(+)-2-bromopropionic acid

101208-75-7

(2R,3S)-2-vinyltetrahydro-2H-pyran-3-ol

1243724-79-9

C10H16O4

Conditions
ConditionsYield
With sodium hydride In 1,4-dioxane69%
10009-70-8

R-(+)-2-bromopropionic acid

bis(2-methoxyphenyl)methanamine

N-(bis(2-methoxyphenyl)methyl)-2-bromopropanamide

Conditions
ConditionsYield
With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 20h; Inert atmosphere;66%
10009-70-8

R-(+)-2-bromopropionic acid

6298-96-0, 22038-86-4, 35600-82-9, 41851-59-6

(R)-1-(4-methoxyphenyl)ethylamine

(R,R)-2-bromo-N--1-(4-methoxyphenylethyl)propanamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;66%
10009-70-8

R-(+)-2-bromopropionic acid

109384-19-2

t-butyl 4-hydroxy piperidine-1-carboxylate

952486-63-4

(2S)-2-[(1-tert-butoxycarbonyl-4-piperidyl)oxy]propanoic acid

Conditions
ConditionsYield
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;
90-33-5, 79566-13-5

7-hydroxy-4-methyl-chromen-2-one

10009-70-8

R-(+)-2-bromopropionic acid

885126-83-0

(S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanoic acid

Conditions
ConditionsYield
With potassium carbonate In acetone at 56℃; for 13h;65%
201864-00-8

(1S)-1-(4-chlorophenylmethyl)-2-hydroxyethylamine

10009-70-8

R-(+)-2-bromopropionic acid

(R)-2-bromo-N-((S)-1-(4-chlorophenyl)-3-hydroxypropan-2-yl)propanamide

Conditions
ConditionsYield
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%
627-27-0

homoalylic alcohol

10009-70-8

R-(+)-2-bromopropionic acid

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 20h; Reflux;53%
10009-70-8

R-(+)-2-bromopropionic acid

979-92-0

S-(5'-adenosyl)-L-homocysteine

(S)-carboxy-S-adenosyl-ethionine

Conditions
ConditionsYield
With ammonium bicarbonate at 37℃; for 18h;50%
10009-70-8

R-(+)-2-bromopropionic acid

195453-23-7

R,S-2,2'-(hydroxyimino)dipropionic acid

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride In water at 30 - 35℃; for 40h; pH=7.2;49%
10009-70-8

R-(+)-2-bromopropionic acid

1421739-59-4

(R)-1,1,1-trichloropent-4-en-2-ol

1421739-53-8

(R)-1,1,1-trichloropent-4-en-2-yl (R’)-2-bromopropanoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 1h; Steglich Esterification; Inert atmosphere;44%
10009-70-8

R-(+)-2-bromopropionic acid

41365-75-7

aminopropane diethyl acetal

98-59-9

p-toluenesulfonyl chloride

105496-31-9

N-(9-fluorenylmethoxycarbonyl)-2-aminoethanol

C19H31N2O6PolS

Conditions
ConditionsYield
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%
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Chemistry

IUPAC Name: (2R)-2-Bromopropanoic acid
Synonyms of (R)-(+)-2-Bromopropionic Acid (CAS NO.10009-70-8): Propanoic acid, 2-bromo-, (2R)- ; (R)-2-Bromopropanoic acid
CAS NO: 10009-70-8
Molecular Formula: C3H5BrO2
Molecular Weight: 152.9746
Molecular Structure:
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.496
Molar Refractivity: 25.2 cm3
Molar Volume: 86.2 cm3
Surface Tension: 44.5 dyne/cm
Density: 1.773 g/cm3
Flash Point: 76.3 °C
Enthalpy of Vaporization: 48.37 kJ/mol
Boiling Point: 202.6 °C at 760 mmHg
Vapour Pressure: 0.12 mmHg at 25°C
Appearance: clear colorless to light brown liquid
SMILES: Br[C@@H](C(=O)O)C
InChI: InChI=1/C3H5BrO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)/t2-/m1/s1
InChIKey: MONMFXREYOKQTI-UWTATZPHBC
Std. InChI: InChI=1S/C3H5BrO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)/t2-/m1/s1
Std. InChIKey: MONMFXREYOKQTI-UWTATZPHSA-N

Safety Profile

Hazard Codes: CorrosiveC
Risk Statements: 22-34
R22: (R)-(+)-2-Bromopropionic Acid (CAS NO.10009-70-8) is harmful if swallowed.
R34: Causes burns.
Safety Statements: 26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3265 8/PG 3
WGK Germany: 3
F:10
HazardClass: 8
PackingGroup: III

Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Do NOT use alcohol foams. Use water spray, dry chemical, carbon dioxide, or appropriate foam. 
Handling: Do not get on skin and clothing. Do not breathe dust, vapor, mist, or gas. Use only in a chemical fume hood.
Storage: Store (R)-(+)-2-Bromopropionic Acid (CAS NO.10009-70-8) in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4°C/39°F.)