Ethyl bromoacetate

Ethyl bromoacetate
Skeletal formula of ethyl bromoacetate
Ball-and-stick model of ethyl bromoacetate
Names
Preferred IUPAC name
Ethyl bromoacetate
Other names
  • Antol
  • Bromoacetic acid, ethyl ester
  • Ethoxycarbonylmethyl bromide
  • Ethyl 2-bromoacetate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.992 Edit this at Wikidata
EC Number
  • 203-290-9
RTECS number
  • AF6000000
UNII
UN number 1603
  • InChI=1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 checkY
    Key: PQJJJMRNHATNKG-UHFFFAOYSA-N checkY
  • InChI=1/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3
    Key: PQJJJMRNHATNKG-UHFFFAOYAE
  • BrCC(=O)OCC
Properties
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]
Insoluble
−82.8·10−6 cm3/mol
Hazards
GHS labelling:
GHS06: Toxic
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)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
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 checkY☒N ?)

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.

  1. ^ a b c d Chemicalland properties database (dead link 13 September 2018)
  2. ^ 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.
  3. ^ Natelson, S.; Gottfried, S. (1955). "Ethyl Bromoacetate". Organic Syntheses; Collected Volumes, vol. 3, p. 381.