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590-13-6

590-13-6 Structure

590-13-6 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Hazard Codes ]

F,Xi
[Risk Statements ]

11-36/37/38
[Safety Statements ]

16-26-36/37/39
[RIDADR ]

UN 1993 3/PG 2
[WGK Germany ]

3
[HazardClass ]

3
[PackingGroup ]

II
Hazard InformationBack 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.
CIS-1-BROMO-1-PROPENE
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

CIS-1-BROMO-1-PROPENE(590-13-6)1HNMR
CIS-1-BROMO-1-PROPENE(590-13-6)13CNMR
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