*** Welcome to piglix ***

2-Chloroethanol

2-Chloroethanol
Skeletal formula of 2-chloroethanol
Ball and stick model of 2-chloroethanol
Spacefill model of 2-chloroethanol
Names
Preferred IUPAC name
2-Chloroethan-1-ol
Other names
  • 2-Chloroethanol
  • Chloroethanol
  • 2-Chloro-1-ethanol
  • β-Chloroethanol
  • δ-Chloroethanol
  • 2-Chloroethyl alcohol
  • Ethylchlorhydrin
  • Ethylene chlorohydrin
  • Glycol chlorohydrin
  • Glycol monochlorohydrin
  • 2-Hydroxyethyl chloride
  • β-Hydroxyethyl chloride
  • 2-Monochloroethanol
Identifiers
3D model (Jmol)
3DMet B01042
878139
ChEBI
ChemSpider
ECHA InfoCard 100.003.146
EC Number 203-459-7
25389
KEGG
MeSH Ethylene+Chlorohydrin
PubChem CID
RTECS number KK0875000
UNII
UN number 1135
Properties
C2H5ClO
Molar mass 80.51 g·mol−1
Appearance Colourless liquid
Odor faint, ether-like
Density 1.201 g mL−1
Melting point −62.60 °C; −80.68 °F; 210.55 K
Boiling point 127 to 131 °C; 260 to 268 °F; 400 to 404 K
miscible
log P −0.107
Vapor pressure 700 Pa (at 20 °C)
1.441
Thermochemistry
−1.1914 MJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H226, H300, H310, H330
P260, P280, P284, P301+310, P302+350
Very Toxic T+
R-phrases R26/27/28
S-phrases (S1/2), S45
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 55 °C (131 °F; 328 K)
425 °C (797 °F; 698 K)
Explosive limits 5–16%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 67 mg kg−1(dermal, rabbit)
72 mg/kg (rat, oral)
81 mg/kg (mouse, oral)
71 mg/kg (rat, oral)
110 mg/kg (guinea pig, oral)
7.5 ppm (rat, 1 hr)
32 ppm (rat, 4 hr)
260 ppm (guinea pig)
33 ppm (rat, 4 hr)
87 ppm (rat)
115 ppm (mouse)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 5 ppm (16 mg/m3) [skin]
REL (Recommended)
 C 1 ppm (3 mg/m3) [skin]
IDLH (Immediate danger)
 7 ppm
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

2-Chloroethanol is an chemical compound with the formula HOCH2CH2Cl and the simplest chlorohydrin. This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional groups.

2-Chloroethanol is produced by treating ethylene with hypochlorous acid:

2-Chloroethanol was once produced on a large scale as a precursor to ethylene oxide:

This application has been supplanted by the greener direct oxidation of ethylene. Otherwise chloroethanol is used in a number of specialized applications. Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol. It is a building block in the production of pharmaceuticals, biocides and plasticizers. It is also used for manufacture of thiodiglycol. It is a solvent for cellulose acetate and ethyl cellulose, textile printing dyes, in dewaxing, refining of rosin, extraction of pine lignin, and the cleaning of machines.

An example is the reaction with theophylline to form Etofylline. Another example is the reaction with chlorphentermine to give Etolorex.


...
Wikipedia

...