Ethyl iodoacetate

Structural formula
General
Surname	Ethyl iodoacetate
other names	Ethyl iodoacetate; SK;
Molecular formula	C 4 H 7 IO 2
Brief description	colorless liquid
External identifiers / databases
EC number	210-796-3
ECHA InfoCard	100.009.816
PubChem	12183
Wikidata	Q1821085
properties
Molar mass	214.00 g mol −1
Physical state	liquid
density	1.808 g cm −3 (25 ° C)
boiling point	179-180 ° C
Refractive index	1.503
safety instructions
H and P phrases	H: 300-314
	P: 264-280-301 + 310-305 + 351 + 338-310
Toxicological data	50 mg kg −1 ( LD 50 , rat , oral )
	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

Ethyl iodoacetate is a chemical compound belonging to the group of derivatives of ethyl acetate .

Extraction and presentation

Ethyl iodoacetate can be obtained by esterifying iodoacetic acid with ethanol or by reacting potassium iodide with ethyl chloroacetate or ethyl bromoacetate .

properties

Ethyl iodoacetate is a colorless liquid that is dark brown as an industrial product. It reacts with simple thiol groups and thus inhibits almost all enzymes .

use

Ethyl iodoacetate is occasionally used as a starting material for organic syntheses. It was used as an irritant during World War I , first by Great Britain at the Battle of Loos in September 1915.

Individual evidence

^ ^A ^b ^c ^d ^e Eric Croddy, Chemical and Biological Warfare A Comprehensive Survey for the Concerned Citizen . Springer Science & Business Media, 2011, ISBN 978-1-4613-0025-0 , p. 120 ( limited preview in Google Book search).
↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet Ethyl iodoacetate, 98% from Sigma-Aldrich , accessed on February 16, 2016 ( PDF ).
↑ prepchem.com: Synthesis of ETHYL IODOACETATE , accessed February 17, 2016.
↑ Jiri Patocka, Kamil Kuca, Military Medical Science Letters Irritant Compounds: Military Respiratory Irritants. Part I, Lacrimators , 2015, 128-139.
↑ Pier Giorgio Cozzi, Alessandro Mignogna, Paola Vicennati: Dimethylzinc-Mediated, Oxidatively Promoted Reformatsky Reaction of Ethyl Iodoacetate with Aldehydes and Ketones. In: Advanced Synthesis & Catalysis. 350, 2008, p. 975, doi : 10.1002 / adsc.200700572 .

[Eric_Croddy-1] A ^b ^c ^d ^e Eric Croddy, Chemical and Biological Warfare A Comprehensive Survey for the Concerned Citizen . Springer Science & Business Media, 2011, ISBN 978-1-4613-0025-0 , p. 120 ( limited preview in Google Book search).

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet Ethyl iodoacetate, 98% from Sigma-Aldrich , accessed on February 16, 2016 ( PDF ).

[prepchem.com-3] repchem.com: Synthesis of ETHYL IODOACETATE , accessed February 17, 2016.

[Jiri_Patocka,_Kamil_Kuca-4] Jiri Patocka, Kamil Kuca, Military Medical Science Letters Irritant Compounds: Military Respiratory Irritants. Part I, Lacrimators , 2015, 128-139.

[DOI10.1002/adsc.200700572-5] Pier Giorgio Cozzi, Alessandro Mignogna, Paola Vicennati: Dimethylzinc-Mediated, Oxidatively Promoted Reformatsky Reaction of Ethyl Iodoacetate with Aldehydes and Ketones. In: Advanced Synthesis & Catalysis. 350, 2008, p. 975, doi : 10.1002 / adsc.200700572 .