| Identification | Back Directory | [Name]
CIS-1-BROMO-1-PROPENE | [CAS]
590-13-6 | [Synonyms]
(Z)-1-Bromopropene
cis-1-Bromopropene
(Z)-Propenyl bromide
(Z)-1-broMoprop-1-ene
Propene,1-bromo-,(Z)-
CIS-1-BROMO-1-PROPENE
(Z)-1-bromo-1-propene
cis-1-bromo-prop-1-ene
(Z)-1-Propenyl bromide
1-propene,1-bromo-,(Z)-
1-Propene,1-bromo-,(1Z)-
cis-1-BroMo-1-propene 97%
(Z)-1-Methyl-2-bromoethene
cis-1-Bromo-1-propene, 98%, stab. with copper | [Molecular Formula]
C3H5Br | [MDL Number]
MFCD00082571 | [MOL File]
590-13-6.mol | [Molecular Weight]
120.98 |
| Chemical Properties | Back Directory | [Melting point ]
-113°C | [Boiling point ]
58 °C(lit.)
| [density ]
1.423 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4545(lit.)
| [Fp ]
<−30 °F
| [solubility ]
soluble in Chloroform | [form ]
Oil | [color ]
Colourless | [Sensitive ]
Light Sensitive | [Stability:]
Light Sensitive, Volatile | [CAS DataBase Reference]
590-13-6 |
| Hazard Information | Back Directory | [Uses]
cis-1-Bromo-1-propene is generally used as a reactant in organic synthesis. | [Application]
Used as a precursor for (E)- or (Z)-1-propenyllithium and 1-propenylmagnesium bromide, and a reagent for electrophilic propenylation.
| [General Description]
cis-1-Bromo-1-propene is an aliphatic olefin. Oxidation of cis-1-bromo-1-propene by toluene dioxygenase has been reported. | [Synthesis]
(Z)- and (E)-1-propenyl bromides can be obtained through spinning band distillation of the commercially available mixture of isomers (Z/E = 70/30). However, the (E)-isomer can only be obtained with difficulty due to thermal isomerization to the (Z)-isomer. Pure (Z)-1-propenyl bromide can be prepared by bromination of (E)-crotonic acid followed by bromodecarboxylation of the resulting erythro-2,3-dibromobutanoic acid in the presence of Triethylamine or Diisopropylethylamine at 40 °C (eq 1). (E)-1-Propenyl bromide can be obtained in 98% purity by treatment of the commercially available mixture of isomers (Z/E = 70/30) with Sodium Hydroxide in n-BuOH at reflux until no (Z)-1-propenyl bromide is detected by GLC.
 | [storage]
Stored in a refrigerator to inhibit thermal and acid-catalyzed isomerization. Avoid breathing
vapor and contact with skin and eyes. Use in a fume hood. |
|
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Sigma-Aldrich
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