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325090

Sigma-Aldrich

Methyl (R)-(+)-3-bromo-2-methylpropionate

97%

Synonym(s):

(+)-Methyl (R)-β-bromoisobutyrate

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About This Item

Linear Formula:
BrCH2CH(CH3)CO2CH3
CAS Number:
110556-33-7
Molecular Weight:
181.03
Beilstein:
1720833
MDL number:
MFCD00010639
UNSPSC Code:
12352101
PubChem Substance ID:
24859486
NACRES:
NA.22
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Assay

97%

form

liquid

optical activity

[α]20/D +16°, neat

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.455 (lit.)

bp

85 °C/37 mmHg (lit.)

density

1.422 g/mL at 25 °C (lit.)

functional group

bromo
ester

SMILES string

COC(=O)[C@@H](C)CBr

InChI

1S/C5H9BrO2/c1-4(3-6)5(7)8-2/h4H,3H2,1-2H3/t4-/m0/s1

InChI key

FKWNAVCXZSQYTA-BYPYZUCNSA-N

Application

Methyl (R)-(+)-3-bromo-2-methylpropionate can be used as a reactant to prepare:
  • (S)-3-(6-Methoxy-pyridin-3-yl)-2-methylpropionic acid methylester by reacting with 5-bromo-2-methoxy pyridine via nucleophilic displacement reaction.[1]
  • Decahydroisoquinoline derivative (NVP-ACQ090) as a potent antagonist of somatostatin sst3 receptor.[1]

It can also be used as a reference compound in the enantioselective alkylation reaction of hydrophobic vitamin B12 derivatives.[2]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

163.4 °F - closed cup

Flash Point(C)

73 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS0508
MKCS0509
MKCB6197
MKCB0118V
MKBQ5433V

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The development of a practical synthesis of the potent and selective somatostatin sst3 receptor antagonist [4-(3, 4-difluoro-phenyl)-piperazine-1-yl]-
Banziger M, et al.
Tetrahedron Asymmetry, 14(22), 3469-3477 (2003)
A 1H NMR and molecular modelling investigation of diastereotopic methylene hydrogen atoms.
Tormena CF, et al.
Magnetic Resonance in Chemistry, 40(4), 279-283 (2002)
Hydrophobic vitamin B12. Part 12. Preparation, characterization and enantioselective alkylation of strapped hydrophobic-vitamin B12
Murakami Y, et al.
J. Chem. Soc. Perkin Trans. II, 14(6), 1175-1183 (1995)
Hydrophobic vitamin B12. Part 12. Preparation, characterization and enantioselective alkylation of strapped hydrophobic-vitamin B12.
Murakami Y, et al.
J. Chem. Soc. Perkin Trans. II, 6, 1175-1183 (1995)

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