1,3-Dibromopropane
Trimethylene bromide
Colorless, pungent - smelling fluid
Liquid
1.98 g · cm -3 ( 20 ° C)
-34 ° C
167 ° C.
2.7 hPa ( 20 ° C)
- Poorly in water ( 1.6 g · l-1 at 20 ° C)
- Soluble in ethanol, diethyl ether, chloroform and other organic solvents.
1.5197 (20 ° C, 656.3 nm)
Attention
315 mg · kg -1 ( LD50, rat, oral)
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1.3 Dibromopropane is a bromine-containing derivative of propane.
Production
1.3 Dibromopropane can by a radical addition (for example, photochemically induced ) reaction between allyl bromide and hydrogen bromide are produced.
The reaction can not be carried out as electrophilic addition, since otherwise the Markovnikov product 1,2-Dibromopropane would be obtained as the main product.
Properties
1.3 Dibromopropane is a colorless, pungent liquid that has a melting point of -34 ° C and a boiling point of 167 ° C.
Use
Since bromides are good leaving groups, 1,3- Dibromopropane can be used in substitution reactions. With suitable nucleophiles, it may be used for the synthesis of cyclobutane derivatives. For example, the CH-acidic cyclopentadiene are deprotonated by base exposure and gradual substitution reactions in a spiro compound of cyclopentadiene can be obtained.
Biological Significance
1.3 Dibromopropane is a skin irritant, harmful if swallowed and toxic to aquatic organisms. It is associated with the water hazard class 2.