CIS-1-BROMO-1-PROPENE Chemical Properties

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.)

Flash point:

<−30 °F

solubility 

soluble in Chloroform

form 

Oil

color 

Colourless

Sensitive 

Light Sensitive

Stability:

Light Sensitive, Volatile

CAS DataBase Reference

590-13-6

Safety Information

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

MSDS

• Language:English Provider:SigmaAldrich

CIS-1-BROMO-1-PROPENE Usage And Synthesis

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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