Ethyl bromoacetate
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Preferred IUPAC name Ethyl bromoacetate | |
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ECHA InfoCard | 100.002.992 |
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UN number | 1603 |
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InChI
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Properties | |
Chemical formula | BrCH2CO2CH2CH3 |
Molar mass | 167.002 g·mol−1 |
Appearance | Colorless to yellow liquid[1] |
Odor | Fruity, pungent[2] |
Density | 1.51 g/cm3 |
Melting point | −38 °C (−36 °F; 235 K)[1] |
Boiling point | 158 °C (316 °F; 431 K)[1] |
Solubility in water | Insoluble |
Magnetic susceptibility (χ) | −82.8·10−6 cm3/mol |
Hazards | |
GHS labelling: | |
Danger | |
H300, H310, H330 | |
P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, P501 | |
NFPA 704 (fire diamond) | 4 0 3 |
Flash point | 47 °C (117 °F; 320 K)[1] |
Related compounds | |
Related esters | |
Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references |
Ethyl bromoacetate is the chemical compound with the formula BrCH2CO2CH2CH3. It is the ethyl ester of bromoacetic acid and is prepared in two steps from acetic acid.[3] It is a lachrymator and has a fruity, pungent odor.[2] It is also a highly toxic alkylating agent and may be fatal if inhaled.
Applications
Ethyl bromoacetate is listed by the World Health Organization as a riot control agent, and was first employed for that purpose by French police in 1912.[4] The French army used rifle grenades 'grenades lacrymogènes'[5] filled with this gas against the Germans beginning in August 1914, but the weapons were largely ineffective, even though ethyl bromoacetate is twice as toxic as chlorine.[6][a] In the early months of the war the British also used the weaponized use of tear gas agents and more toxic gasses including sulfur dioxide.[7] The German army then used these attacks to justify their subsequent employment of it as odorant or warning agent in odorless, toxic gases and chemical weapons in 1915 under the German code Weisskreuz (White Cross).[8]
In organic synthesis, it is a versatile alkylating agent. Its major application involves the Reformatsky reaction, wherein it reacts with zinc to form a zinc enolate. The resulting BrZnCH2CO2CH2CH3 condenses with carbonyl compounds to give a β-hydroxy-esters.
It is also the starting point for the preparation of several other reagents. For example, the related Wittig reagent (prepared by reaction with triphenylphosphine) is commonly used to prepare alpha,beta-unsaturated esters from carbonyl compounds such as benzaldehyde:[9]
References
- ^ a b c d Chemicalland properties database (dead link 13 September 2018)
- ^ a b Criswell, DW; McClure, FL; Schaefer, R; Brower, KR (1980). "War gases as olfactory probes". Science. 210 (4468): 425–6. Bibcode:1980Sci...210..425C. doi:10.1126/science.6968976. PMID 6968976.
- ^ Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses; Collected Volumes, vol. 3, p. 381.
- ^ Public health response to biological and chemical weapons, Chapter 3, Biological and Chemical agents, WHO Guidance]
- ^ "Plaidoyer pour la guerre des gaz". 15 April 2005.
- ^ "Plaidoyer pour la guerre des gaz". 15 April 2005.
- ^ "Poison Gas and World War One".
- ^ Heller, Charles E. (September 1984). "Chemical Warfare in World War I: The American Experience, 1917-1918". Combat Studies Institute. Archived from the original on 2007-07-04. Retrieved 2007-08-02.
- ^ A student lab procedure for the Wittig sequence shown, only using the related methyl ester.
Footnotes
- ^ The small quantities of gas delivered, roughly 19 cm3 per cartridge, were not even detected by the Germans. The stocks were rapidly consumed.[Why bromoacetate failed in WW1]
External links
- Environmental Health & Safety dept, Northeastern University
- v
- t
- e
- Agents used in chemical warfare
- incapacitation
- riot control
- Cyanogen
- Cyanogen bromide
- Cyanogen chloride (CK)
- Hydrogen cyanide (AC)
- Arsine
- Cacodyl cyanide
- Cacodyl oxide
- Hydrogen sulfide
- Phosphine
- Carbon monoxide
- Phosphorus trifluoride
- Methyl cyanoformate
- Iron pentacarbonyl
- Nickel tetracarbonyl
- 2,3,7,8-Tetrachlorodibenzodioxin
- Glycolonitrile
- Lactonitrile
- Acetone cyanohydrin
- Stibine
- Chloral cyanohydrin
Arsenicals | |
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Sulfur mustards |
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Nitrogen mustards | |
Nettle agents |
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Other |
- Anatoxin-a
- Saxitoxin (TZ)
- Bungarotoxin
- Botulinum toxin (BTX)
- Tetanospasmin (TeNT)
- Ryanodine
- Ciguatoxin (CTX)
- Guanitoxin (GTX)
- Chlorophenylsilatrane
- Palytoxin (PTX)
- Maitotoxin (MTX)
- Tetrodotoxin
- Aconitine
- Brevetoxin (PbTX)
- Strychnine
- Antillatoxin (ATX)
- Tetraethyllead
- Dimethylmercury
- HN1 hydrochloride
- HN2 hydrochloride
- HN3 hydrochloride
- A-8564
- Picrotoxin
- Sulfuryl fluoride
- Tremorine
- Oxotremorine
- Batrachotoxin
- Tetramethylenedisulfotetramine (TETS)
- Bicyclic phosphates
- Cloflubicyne
- Trimethylolpropane phosphite
- Domoic acid
choking agents
- Chlorine
- Bromine
- Phosgene (CG)
- Fluorine
- Perfluoroisobutene
- Chloropicrin (PS)
- Dimethyl(trifluoromethylthio)arsine
- Diphosgene (DP)
- Disulfur decafluoride (Z)
- Acrolein
- Ethyl bromoacetate
- Perchloromethyl mercaptan
- Phenylcarbylamine chloride
- Tetranitromethane
- Tetrachlorodinitroethane
- Chlorine trifluoride
- Perchloryl fluoride
- Cadmium oxide
- Cadmium chloride
- Mercuric chloride
- Selenium dioxide
- Selenoyl fluoride
- Trifluoronitrosomethane
- Trichloronitrosomethane
- Nitric oxide
- Nitrogen dioxide
- Dinitrogen tetroxide
- Sulfur dioxide
- Phosphorus trichloride
- Methyl isocyanate
- Ethenone
- Methyl vinyl ketone
- Trifluoroacetyl chloride
- Salcomine
- Fluomine
- Uranium hexafluoride
- Diborane
- Green Cross
agents
- BZ (CS-4030)
- Apomorphine
- Butyrophenone
- EA-4941 (CS-4640)
- Etorphine
- EA-2092
- CS-4297
- Etoxadrol
- Dimethylheptylpyran (DMHP)
- EA-2148
- EA-3167
- EA-3443
- Pethidine
- EA-3580
- Ibogaine
- EA-3834
- Kolokol-1
- LSD-25
- PAVA spray
- Psilocybin
- Sleeping gas
- Carfentanil
- JB-318
- JB-336
- CS-27349
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,668
- Benperidol
- Desflurane
- Enflurane
- Bufotenin
- Isoflurane
- Halothane
- Sevoflurane
- Pentazocine
- Procarbazine
- Fluphenazine
- Chlorpromazine
agents
- Xylyl bromide
- Pepper spray (OC)
- Mace (spray)
- CN
- CS
- CR
- CNS
- Benzyl chloride
- Benzyl bromide
- Benzyl iodide
- Bromobenzyl cyanide
- Thiophosgene
- Chloroacetone
- Bromoacetone
- Bromomethyl ethyl ketone
- Acrolein
- Phenacyl bromide
- Chloroacetophenone oxime
- Ethyl bromoacetate
- Ethyl iodoacetate
- Iodoacetone
- Allyl isothiocyanate
- Hexamethylene diisocyanate
- Crotonaldehyde
- Abrin
- Aconitine
- Cyclopiazonic acid
- Histrionicotoxins
- Aflatoxins
- Anatoxin-a
- Batrachotoxin
- Botulinum toxin
- Brevetoxin
- Ciguatoxin
- Domoic acid
- Enterotoxin type B
- Grayanotoxin
- Guanitoxin
- Maitotoxin
- Modeccin
- Palytoxin
- Ricin
- Saxitoxin
- Shiga toxin
- T-2 mycotoxin
- Tetanospasmin
- Tetrodotoxin
- Volkensin
- Veratridine
- Methyl fluoroacetate
- Napalm (variants and mixtures)
- Fluoroethyl fluoroacetate
- Depleted uranium
- post-combustion uranium oxides
- Plutonium and its compounds
- Polonium
- White phosphorus
Organic Chemistry