16503

Methyl 2-bromo-2-butenoate

(cis+trans), ≥95.0% (GC)

• Synonym(s): Methyl 2-bromocrotonate
• Linear Formula: CH₃CH=CBrCOOCH₃
• CAS Number: 17642-18-1
• Molecular Weight: 179.01
• Beilstein/REAXYS Number: 1700999
• EC Number: 241-627-1
• MDL number: MFCD00042891
• UNSPSC Code: 12352100
• PubChem Substance ID: 57647571
• NACRES: NA.22

Properties

• assay: ≥95.0% (GC)
• refractive index: n20/D 1.486
• bp: 178-182 °C (lit.)
• density: 1.505 g/mL at 20 °C (lit.)
• functional group: bromo; ester
• storage temp.: 2-8°C
• SMILES string: COC(=O)C(Br)=CC
• InChI: 1S/C5H7BrO2/c1-3-4(6)5(7)8-2/h3H,1-2H3
• InChI key: DMKWWKUPZZAUQL-UHFFFAOYSA-N

Description

General description

Methyl 2-bromo-2-butenoate(Methyl (Z)-2-bromocrotonate) yields (S)-2-bromobutanoic acid by baker′s yeast fermentation. It undergoes biotransformation catalyzed by old yellow enzyme to yield methyl (S)-2-bromobutanoate, a key intermediate for the synthesis of chiral drugs. It is a biannelating reagent which participates in double Michael-additions.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: 145.4 °F - closed cup
• flash_point_c: 63 °C - closed cup
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter