2,3-dibromo propanol
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| Chemical formula | C3H6Br2O |
|---|---|
| Molar Mass(g/mol) | 217.88714 |
| Density(g/cc) | 2.120 |
| Boiling Point(°C) | 291 |
| NFPA 704 |  0
0
|
Uses
Justification Questioned
Primary
- Precursor for WHO LEM Dimercaprol
Natural occurrence
Hazards
Character
Production
Synthesis
Bromine is usually possible to add to unsaturated alcohols in dilute solution at 0-25° without replacement of the hydroxyl group. 2,3-dibromo-1-propanol is obtained by treating allyl alcohol in ten times its volume of carbon tetrachloride with a solution of the calculated amount of bromine in double its volume of carbon tetrachloride. Carbon tetrachloride is evaporated and ,3-dibromo-1-propanol is purified by distillation collecting the fraction boiling at 95-97° C/10 mmHg, n20/D 1.559, d=2.12 g/ml at 25 °C.[1]
- CH2-CH-CH2OH + Br2{CCl4BrCH2-BrCH-CH2OH}→
222 g is tetramethylammonium bromide-bromine adduct are dropped into 1 mole or 58 g of allyl alcohol during 40 min with ice cooling and stirring at 40° C. Tetramethylammonium bromide is precipitated, which is filtered off and washed with ether, being recovered almost quantitatively. The filtrate and the ether used for washing are united. Distillation at 95-97° C/10 mmHg affords 2,3-dibromo-1-propanol in 85 % yield. [2]