(2R)-3-Bromo-2-hydroxy-2-methylpropanoic acid supplier

Name
(2R)-3-Bromo-2-hydroxy-2-methylpropanoic acid
EINECS
CAS No. 261904-39-6
Article Data37
CAS DataBase
Density 1.831 g/cm³
Solubility
Melting Point 113.0 to 117.0 °C
Formula C₄H₇BrO₃
Boiling Point 294.474 °C at 760 mmHg
Molecular Weight 183.002
Flash Point 131.893 °C
Transport Information
Appearance
Safety 26
Risk Codes 36/38
Molecular Structure
Hazard Symbols Xi
Synonyms (+)-(2R)-3-Bromo-2-hydroxy-2-methylpropanoicacid;(2R)-3-Bromo-2-hydroxy-2-methylpropanoic acid;(2R)-3-Bromo-2-hydroxy-2-methylpropionicacid;
PSA 57.53000
LogP 0.21690

Synthetic route

: 106138-80-1
(3R,8AR)-3-Bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

Conditions

Conditions	Yield
With hydrogen bromide for 5h; Reflux;	91.3%
With hydrogen bromide In water for 1h; Heating / reflux;	86%
With water; hydrogen bromide for 1h; Heating / reflux;	86%

: (3R,8αR)-3-(bromomethyl)-3-methyl-tetrahydro-3H-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

Conditions

Conditions	Yield
With water; hydrogen bromide for 1h; Heating / reflux;	85%
With hydrogen bromide at 105℃; for 1.5h;	84%
With hydrogen bromide In water at 105℃; Temperature; Large scale;

: 3-bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

A: (2R)-3-chloro-2-hydroxy-2-methylpropanoic acid

B: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

Conditions

Conditions	Yield
With hydrogenchloride Hydrolysis; Heating; Title compound not separated from byproducts.;

: 1250440-74-4
C9H15BrO3

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In water for 4h; Reflux; Inert atmosphere;
With hydrogenchloride; water for 4h; Reflux;

: 106089-24-1
(2R)-1-methacryloylpyrrolidin-2-carboxylic acid

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

Conditions

Conditions	Yield
Stage #1: (2R)-1-methacryloylpyrrolidin-2-carboxylic acid With N-Bromosuccinimide In N,N-dimethyl-formamide Stage #2: With hydrogenchloride In water at 100℃;

: 2993-22-8
3-pentafluorosulfuraniline

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: (R)-3-bromo-2-hydroxy-2-methyl-N-(3-(pentafluorosulfanyl)phenyl)propanamide

Conditions

Conditions	Yield
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In N,N-dimethyl acetamide at -10 - -5℃; for 3h; Inert atmosphere; Stage #2: 3-pentafluorosulfuraniline In N,N-dimethyl acetamide at 20℃; for 16h; Inert atmosphere;	96%

: 55338-73-3
5-amino-2-cyanopyridine

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: (2R)-3-bromo-N-(6-cyanopyridin-3-yl)-2-hydroxy-2-methylpropanamide

Conditions

Conditions	Yield
With thionyl chloride; trimethylamine	92%
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In tetrahydrofuran at 0 - 12℃; for 2.166h; Stage #2: With triethylamine In tetrahydrofuran at -5 - 12℃; for 0.333333h; Stage #3: 5-amino-2-cyanopyridine In tetrahydrofuran at 50℃; for 2h;	85%

: 573762-62-6
5-amino-3-(trifluoromethyl)-2-pyridinecarbonitrile

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: (R)-3-bromo-N-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-2-hydroxy-2-methylpropanamide

Conditions

Conditions	Yield
With thionyl chloride; trimethylamine	90%
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In tetrahydrofuran at 0 - 12℃; for 2.166h; Stage #2: With triethylamine In tetrahydrofuran at -5 - 12℃; for 0.333333h; Stage #3: 5-amino-3-(trifluoromethyl)pyridine-2-carbonitrile In tetrahydrofuran at 50℃; for 2h;	85%
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In tetrahydrofuran at 4℃; for 3h; Inert atmosphere; Stage #2: With triethylamine In tetrahydrofuran at 4℃; for 0.333333h; Inert atmosphere; Stage #3: 5-amino-3-(trifluoromethyl)pyridine-2-carbonitrile In tetrahydrofuran at 20℃;	70.2%

: 115-17-3
bromal

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 1003838-02-5
C7H8Br4O3

Conditions

Conditions	Yield
With sulfuric acid at 0 - 20℃;	89%

: 20925-27-3
4-amino-2-chlorobenzonitrile

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 1002330-78-0
(2R)-3-bromo-N-(3-chloro-4-cyanophenyl)-2-hydroxy-2-methylpropanamide

Conditions

Conditions	Yield
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In tetrahydrofuran at 0 - 12℃; for 2.166h; Stage #2: With triethylamine In tetrahydrofuran at -5 - 12℃; for 0.333333h; Stage #3: 4-amino-2-chlorobenzonitrile In tetrahydrofuran at 50℃; for 2h;	88.6%
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In tetrahydrofuran at 4℃; for 3h; Inert atmosphere; Stage #2: 4-amino-2-chlorobenzonitrile With triethylamine In tetrahydrofuran at 20℃;	73%
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In tetrahydrofuran at 4℃; for 3h; Inert atmosphere; Stage #2: In tetrahydrofuran for 0.333333h; Inert atmosphere; Stage #3: 4-amino-2-chlorobenzonitrile In tetrahydrofuran at 20℃; Inert atmosphere;	73%
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In tetrahydrofuran at 4℃; for 3h; Inert atmosphere; Stage #2: 4-amino-2-chlorobenzonitrile With triethylamine In tetrahydrofuran at 20℃;	49.4%
With thionyl chloride In tetrahydrofuran at 0℃;

: 2993-24-0
4-(pentafluorosulfanyl)aniline

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: (R)-3-bromo-2-hydroxy-2-methyl-N-(4-(pentafluorosulfanyl)phenyl)propanamide

Conditions

Conditions	Yield
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In N,N-dimethyl acetamide at -10 - -5℃; for 3h; Inert atmosphere; Stage #2: 4-(pentafluorosulfanyl)aniline In N,N-dimethyl acetamide at 20℃; for 16h; Inert atmosphere;	88%

: 654-70-6
4-amino-2-trifluoromethylbenzonitrile

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 206193-17-1
(2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide

Conditions

Conditions	Yield
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In N,N-dimethyl acetamide at -10℃; for 3h; Inert atmosphere; Stage #2: 4-amino-2-trifluoromethylbenzonitrile In N,N-dimethyl acetamide at -10 - 20℃; for 16h; Inert atmosphere;	84%
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In ISOPROPYLAMIDE at -10℃; Inert atmosphere; Stage #2: 4-amino-2-trifluoromethylbenzonitrile In ISOPROPYLAMIDE at 20℃;	84%
With thionyl chloride In N,N-dimethyl acetamide at -15 - 40℃; for 3.5h;	80.4%

: 64-17-5
ethanol

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: (R)-3-bromo-2-hydroxy-2-methyl-propionic acid ethyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 7h; Reflux;	83%

: 393-11-3
4-nitro-3-(trifluoromethyl)benzeneamine

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 206193-18-2
N-[4-nitro-3-(trifluoromethyl)phenyl]-(2R)-3-bromo-2-hydroxy-2-methylpropanamide

Conditions

Conditions	Yield
With thionyl chloride In N,N-dimethyl acetamide at 20℃;	80%
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In dimethyl amine at -10 - -5℃; for 2h; Stage #2: 4-nitro-3-(trifluoromethyl)benzeneamine In dimethyl amine at 20℃;	80%
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In 2,4-dichlorophenoxyacetic acid dimethylamine at -10℃; for 2h; Stage #2: 4-nitro-3-(trifluoromethyl)benzeneamine In 2,4-dichlorophenoxyacetic acid dimethylamine at 20℃;	80%
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In tetrahydrofuran at 10℃; for 2.83333h; Inert atmosphere; Large scale; Stage #2: 4-nitro-3-(trifluoromethyl)benzeneamine With triethylamine In tetrahydrofuran at 10 - 50℃; for 18.75h; Large scale;	70.3%
With thionyl chloride In N,N-dimethyl acetamide at -15 - 40℃; for 8.5h;	57.2%

: 852569-35-8
4-amino-5-iodo-2-(trifluoromethyl)benzonitrile

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: (R)-3-bromo-N-(4-cyano-2-iodo-5-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide

Conditions

Conditions	Yield
With thionyl chloride; triethylamine	64.6%

: 852469-69-3
4-amino-2-(pentafluorosulfanyl)benzonitrile

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: (R)-3-bromo-N-(4-cyano-3-(pentafluorosulfanyl)phenyl)-2-hydroxy-2-methylpropanamide

Conditions

Conditions	Yield
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In N,N-dimethyl acetamide at -10 - -5℃; for 3h; Inert atmosphere; Stage #2: 4-amino-2-(pentafluorosulfanyl)benzonitrile In N,N-dimethyl acetamide at 20℃; for 16h; Inert atmosphere;	49%

: 14432-12-3
4-Amino-2-chloropyridine

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: (R)-3-bromo-N-(2-chloropyridin-4-yl)-2-hydroxy-2-methylpropanamide

Conditions

Conditions	Yield
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In tetrahydrofuran at 4℃; for 3h; Inert atmosphere; Stage #2: With triethylamine In tetrahydrofuran at 4℃; for 0.333333h; Stage #3: 4-Amino-2-chloropyridine In tetrahydrofuran at 4 - 20℃;	43%

: 367-12-4
2-fluorophenol

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 1578263-99-6
C10H11FO4

Conditions

Conditions	Yield
With potassium carbonate In butanone for 16h; Reflux;	15%

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 1010396-30-1
(R)-3-bromo-2-hydroxy-2-methylpropanoyl chloride

Conditions

Conditions	Yield
With thionyl chloride In tetrahydrofuran at 0℃;
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at -10 - -5℃; for 3h;
With thionyl chloride In tetrahydrofuran at 0℃;

bromoacid: bromoacid

: 393-11-3
4-nitro-3-(trifluoromethyl)benzeneamine

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 206193-18-2
N-[4-nitro-3-(trifluoromethyl)phenyl]-(2R)-3-bromo-2-hydroxy-2-methylpropanamide

Conditions

Conditions	Yield
With thionyl chloride In 2,4-dichlorophenoxyacetic acid dimethylamine	18.0 g (80%)
With thionyl chloride In 2,4-dichlorophenoxyacetic acid dimethylamine	18.0 g (80%)
With thionyl chloride In 2,4-dichlorophenoxyacetic acid dimethylamine	18.0 g (80%)

...Expand

: 124-40-3
dimethyl amine

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 936910-33-7
C6H13NO3

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 2h;

: 611-05-2
4-nitro-3-methylaniline

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 821764-69-6
(2R)-3-bromo-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

Conditions

Conditions	Yield
Stage #1: (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid With thionyl chloride In ISOPROPYLAMIDE at -10 - -5℃; for 2h; Heating / reflux; Stage #2: 4-nitro-3-methylaniline In ISOPROPYLAMIDE at 20℃; for 3h;

CH2Cl2/EtOAc: CH2Cl2/EtOAc

: 654-70-6
4-amino-2-trifluoromethylbenzonitrile

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

A: 206193-17-1
(2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide

B: 106138-80-1
(3R,8AR)-3-Bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

Conditions

Conditions	Yield
With thionyl chloride; triethylamine In tetrahydrofuran; water	A n/a B 55.8 g (73.9%)

...Expand

CH2Cl2/EtOAc: CH2Cl2/EtOAc

: 654-70-6
4-amino-2-trifluoromethylbenzonitrile

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 206193-17-1
(2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide

Conditions

Conditions	Yield
With thionyl chloride; triethylamine In tetrahydrofuran; water	55.8 g (73.9%)

...Expand

: 371-41-5
4-Fluorophenol

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: C10H11FO4

Conditions

Conditions	Yield
With potassium carbonate In butanone for 16h; Reflux;

: 371-42-6
4-Fluorothiophenol

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: 335595-52-3
(R)-3-(4-fluorophenylmercapto)-2-hydroxy-2-methylpropionic acid

Conditions

Conditions	Yield
With sodium hydroxide In isopropyl alcohol

: 101421-72-1
6-amino-quinazoline

: 261904-39-6
(2R)-3-bromo-2-hydroxy-2-methylpropanoic acid

: (R)-3-bromo-2-hydroxy-2-methyl-N-(quinazolin-6-yl) propanamide

Conditions

Conditions	Yield
With thionyl chloride; trimethylamine	0.71 g

(2R)-3-Bromo-2-hydroxy-2-methylpropanoic acid Specification

The (2R)-3-Bromo-2-hydroxy-2-methylpropanoic acid with its cas register number is 261904-39-6. It also can be called as Propanoic acid,3-bromo-2-hydroxy-2-methyl-, (2R)- and the Systematic name about this chemical is (2R)-3-bromo-2-hydroxy-2-methylpropanoic acid.

Physical properties about (2R)-3-Bromo-2-hydroxy-2-methylpropanoic acid are: (1)ACD/LogP: 0.43; (2)ACD/LogD (pH 5.5): -2; (3)ACD/LogD (pH 7.4): -3; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 57.53Å²; (12)Index of Refraction: 1.541; (13)Molar Refractivity: 31.377 cm³; (14)Molar Volume: 99.924 cm³; (15)Polarizability: 12.439x10^-24cm³; (16)Surface Tension: 59.096 dyne/cm; (17)Enthalpy of Vaporization: 61.967 kJ/mol.

You can still convert the following datas into molecular structure:
(1)SMILES: BrC[C@](O)(C(=O)O)C
(2)InChI: InChI=1/C4H7BrO3/c1-4(8,2-5)3(6)7/h8H,2H2,1H3,(H,6,7)/t4-/m0/s1
(3)InChIKey: HBJAYXGUOOININ-BYPYZUCNBM
(4)Std. InChI: InChI=1S/C4H7BrO3/c1-4(8,2-5)3(6)7/h8H,2H2,1H3,(H,6,7)/t4-/m0/s1
(5)Std. InChIKey: HBJAYXGUOOININ-BYPYZUCNSA-N

Product Name

(2R)-3-Bromo-2-hydroxy-2-methylpropanoic acid

Synthetic route

(2R)-3-Bromo-2-hydroxy-2-methylpropanoic acid Specification

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