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| | Methyl 2-bromo-2-butenoate Basic information |
| Product Name: | Methyl 2-bromo-2-butenoate | | Synonyms: | METHYL 2-BROMOCROTONATE;METHYL A-BROMOCROTONATE;methyl 2-bromo-2-butenoate (cis+trans);2-Bromo-2-butenoic acid methyl ester;Einecs 241-627-1;(Z)-Methyl 2-broMobut-2-enoate;Methyl 2-bromo-2-butenoate (cis+trans), >=95.0% (GC);2-Butenoic acid, 2-bromo-, methyl ester | | CAS: | 17642-18-1 | | MF: | C5H7BrO2 | | MW: | 179.01 | | EINECS: | 241-627-1 | | Product Categories: | | | Mol File: | 17642-18-1.mol |  |
| | Methyl 2-bromo-2-butenoate Chemical Properties |
| Boiling point | 178-182 °C (lit.) | | density | 1.505 g/mL at 20 °C (lit.) | | refractive index | n20/D 1.486 | | Fp | 63 °C | | storage temp. | 2-8°C | | BRN | 1700999 | | InChI | 1S/C5H7BrO2/c1-3-4(6)5(7)8-2/h3H,1-2H3 | | InChIKey | DMKWWKUPZZAUQL-UHFFFAOYSA-N | | SMILES | COC(=O)C(Br)=CC |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | F | 8 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | Methyl 2-bromo-2-butenoate Usage And Synthesis |
| Uses | 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.
| | 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.
| | Synthesis | Ethyl or methyl crotonate is treated with Br2/CCl4 or Br2/AcOH followed by dehydrobromination with quinoline or DBU to afford Methyl 2-bromo-2-butenoate.
| | Precautions | Handle under nitrogen in a fume hood; these reagents are moisture-sensitive. Store refrigerated and in brown bottles to avoid polymerization. Caution: lachrymator and irritant; may be harmful.
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| | Methyl 2-bromo-2-butenoate Preparation Products And Raw materials |
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