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.