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16491

Sigma-Aldrich

Methyl bromopyruvate

technical

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About This Item

Linear Formula:
BrCH2COCOOCH3
CAS Number:
7425-63-0
Molecular Weight:
180.98
Beilstein:
1754888
MDL number:
MFCD01862963
UNSPSC Code:
12352100
PubChem Substance ID:
57647569
NACRES:
NA.22

grade

technical

Quality Level

100

Assay

≥95.0% (T)

form

liquid

density

1.70 g/mL at 20 °C (lit.)

functional group

bromo
ester
ketone

storage temp.

2-8°C

SMILES string

COC(=O)C(=O)CBr

InChI

1S/C4H5BrO3/c1-8-4(7)3(6)2-5/h2H2,1H3

InChI key

MQONVZMIFQQQHA-UHFFFAOYSA-N

General description

Methyl bromopyruvate is an inhibitor of carbonic anhydrase.

Application

Methyl bromopyruvate was used in the synthesis of 2-(4-amino-4-carboxybutyl)thiazole-4-carboxylic acid and methyl-1-(bromomethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate.

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)

257.0 °F - closed cup

Flash Point(C)

125 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7782
BCBQ2142V
BCBN8220V
BCBM0067V
BCBM7730V

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Anne Katrine Kehler et al.
Investigative ophthalmology & visual science, 48(10), 4688-4693 (2007-09-28)
Inhibition of carbonic anhydrase in the eye is an important treatment modality for reducing the intraocular pressure in glaucoma. However, evidence suggests that carbonic anhydrase inhibition also exerts a relaxing effect on the vessels in the optic nerve, and it
Further degradation products of cephalosporin C. Isolation and synthesis of 2-(4-amino-4-carboxybutyl)thiazole-4-carboxylic acid.
J D JEFFERY et al.
The Biochemical journal, 75, 216-223 (1960-05-01)
Pinhong Chen et al.
The Journal of organic chemistry, 74(19), 7533-7535 (2009-09-26)
With chemoselective Dieckmann condensation as the key step, the protective-group-free total synthesis of (+/-)-subincanadine F was accomplished in 7 steps from the commercially available tryptamine in 33% overall yield.

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