Ethyl bromoacetate

Ethyl bromoacetate
Names
	Preferred IUPAC name Ethyl bromoacetate
	Other names Antol; Bromoacetic acid, ethyl ester; Ethoxycarbonylmethyl bromide; Ethyl 2-bromoacetate;
Identifiers
CAS Number	105-36-2 ;
3D model ( JSmol)	Interactive image;
ChEMBL	ChEMBL1085948 ;
ChemSpider	7462 ;
ECHA InfoCard	100.002.992
EC Number	203-290-9;
PubChem CID	7748;
RTECS number	AF6000000;
UNII	D20KFB313W ;
UN number	1603
CompTox Dashboard (EPA)	DTXSID4020587 ;
	InChI InChI=1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 Key: PQJJJMRNHATNKG-UHFFFAOYSA-N ; InChI=1/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 Key: PQJJJMRNHATNKG-UHFFFAOYAE;
	SMILES BrCC(=O)OCC;
Properties
Chemical formula	BrCH2CO2CH2CH3
Molar mass	167.002 g·mol−1
Appearance	Colorless to yellow liquid
Odor	Fruity, pungent
Density	1.51 g/cm3
Melting point	−38 °C (−36 °F; 235 K)
Boiling point	158 °C (316 °F; 431 K)
Solubility in water	Insoluble
Magnetic susceptibility (χ)	−82.8·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H330
Precautionary statements	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)
Related compounds
Related esters	Methyl bromoacetate; Ethyl 3-bromopropionate; Ethyl chloroacetate; Ethyl iodoacetate; Ethyl bromodifluoroacetate; Ethyl acetoacetate;
Related compounds	Bromoacetic acid; Pepper spray; Chloropicrin;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ethyl bromoacetate is the

alkylating agent

and may be fatal if inhaled.

Applications

Ethyl bromoacetate is listed by the

odorant or warning agent in odorless, toxic gases and chemical weapons in 1915 under the German code Weisskreuz (White Cross).^[8]

In

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

unsaturated esters from carbonyl compounds such as benzaldehyde:^[9]

Ethyl bromoacetate as the starting point for a Wittig reaction sequence

References

^ ^a ^b ^c ^d Chemicalland properties database (dead link 13 September 2018)
^
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

Organic Chemistry

[chemicalland21-1] Chemicalland properties database (dead link 13 September 2018)

[Criswell-2] 
PMID 6968976
.

[3] Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses; Collected Volumes, vol. 3, p. 381.

[4] Public health response to biological and chemical weapons, Chapter 3, Biological and Chemical agents, WHO Guidance]

[5] "Plaidoyer pour la guerre des gaz". 15 April 2005.

[6] "Plaidoyer pour la guerre des gaz". 15 April 2005.

[8] "Poison Gas and World War One".

[heller84-9] 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.

[10] A student lab procedure for the Wittig sequence shown, only using the related methyl ester.

[7] 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]

[1]

[2]

[8]

[9]