Bromoacetone
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| General | ||||||||||||||||
| Surname | Bromoacetone | |||||||||||||||
| other names |
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| Molecular formula | C 3 H 5 BrO | |||||||||||||||
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| properties | ||||||||||||||||
| Molar mass | 136.97 g · mol -1 | |||||||||||||||
| Physical state |
liquid |
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| density |
1.63 g cm −3 |
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| Melting point |
−54 ° C |
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| boiling point |
136.5 ° C |
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| Vapor pressure |
12 h Pa (20 ° C) |
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| solubility |
very heavy in water |
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| Refractive index |
1.4697 (15 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C | ||||||||||||||||
Bromacetone is a colorless, pungent smelling liquid that was previously used as an eye irritant in tear gases . In this function it was initially replaced temporarily by ω-chloroacetophenone (CN), today this is largely replaced by 2-chlorobenzylidene-malononitrile (CS).
history
Bromine and chloroacetone were among the first weapons used in the war. During the First World War they were used by the German Army under the name Weißkreuz . Even today, some of them are used by the police as tear gas.
Manufacturing
The production of bromoacetone is very simple: bromine and acetone react at room temperature with self-heating to form bromoacetone and hydrogen bromide . The boiling acetone acts as a propellant for the tear gas.
properties
Bromacetone primarily attacks the eyes , but also the upper mucous membranes ( nose and throat ). Symptoms appear immediately and quickly go away after exposure.
α-Halocarbonyl compounds have a corrosive effect on metals (iron, brass).
See also
Individual evidence
- ↑ a b c d e Entry on bromoacetone in the GESTIS substance database of the IFA , accessed on February 28, 2017(JavaScript required) .
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-56.
- ↑ Entry on bromoacetone at TCI Europe, accessed on February 16, 2020.
- ↑ 1-bromopropan-2-one at Fluorochem. Retrieved March 14, 2020 .
- ↑ Wolfgang Legrum: Fragrances, between stink and fragrance , Vieweg + Teubner Verlag (2011) pp. 74–75, ISBN 978-3-8348-1245-2 .