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2-Chloroethanol

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2-Chloroethanol Basic information

Product Name:
2-Chloroethanol
Synonyms:
  • monochlorhydrineduglycol[french]
  • NCI-C50135
  • Z-Chloroethanol
  • αthylenchlorhydrin
  • 2-CHLOROETHANOL
  • 2-CHLORETHANOL
  • 1-Chloro-2-hydroxyethane
  • 2-Chloorethanol
CAS:
107-07-3
MF:
C2H5ClO
MW:
80.51
EINECS:
203-459-7
Product Categories:
  • Alkohols
  • API Intermediate
  • Isotope Labelled Compounds, Miscellaneous Reagents
Mol File:
107-07-3.mol
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2-Chloroethanol Chemical Properties

Melting point:
-63 °C
Boiling point:
129 °C(lit.)
Density 
1.201 g/mL at 25 °C(lit.)
vapor density 
2.78 (vs air)
vapor pressure 
5 mm Hg ( 20 °C)
refractive index 
n20/D 1.441(lit.)
Flash point:
140 °F
storage temp. 
2-8°C
solubility 
Soluble in alcohol (Weast, 1986)
form 
Liquid
color 
Yellow
Odor
Faint, ethereal.
Water Solubility 
MISCIBLE
Sensitive 
Moisture Sensitive
Merck 
14,3793
BRN 
878139
Exposure limits
Ceiling limit 3 mg/m3 (1 ppm) skin (ACGIH); TLV-TWA air 16 mg/m3 (5 ppm) skin (OSHA); IDLH 10 ppm (NIOSH).
Stability:
Stable. Incompatible with oxidizing agents.
CAS DataBase Reference
107-07-3(CAS DataBase Reference)
NIST Chemistry Reference
Ethanol, 2-chloro-(107-07-3)
EPA Substance Registry System
Ethanol, 2-chloro-(107-07-3)
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Safety Information

Hazard Codes 
T+,T,F
Risk Statements 
26/27/28-39/23/24/25-23/24/25-11-10
Safety Statements 
28-45-7/9-28A-36/37-16-7
RIDADR 
UN 1135 6.1/PG 1
WGK Germany 
3
RTECS 
KK0875000
21
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
I
HS Code 
29333999
Hazardous Substances Data
107-07-3(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 0.095 g/kg (Smyth)

MSDS

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2-Chloroethanol Usage And Synthesis

Description

Ethylene chlorohydrine is a clear, colourless liquid with mild, ethereal odour. It reacts with alkali metals. Ethylene chlorohydrine has applications as a laboratory reagent and as a pharmaceutical intermediate. Ethylene chlorohydrine is a building block in the production of pharmaceuticals, biocides, and plasticisers, used for manufacture of thiodiglycol, an important solvent for cellulose acetate and ethyl cellulose, textile-printing dyes, extraction of pine lignin, in dewaxing, refining of rosin, and the cleaning of machines. Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.

Chemical Properties

Ethylene chlorohydrin is a colorless liquid with a faint, ethereal odor.

Chemical Properties

colourless liquid

Physical properties

Colorless liquid with a faint, ether-like odor. Odor threshold concentration is 400 ppb (quoted, Keith and Walters, 1992).

Uses

Ethylene chlorohydrin is used in the manufacture of insecticides, as a solvent for cellu lose esters, in treating sweet potatoes beforeplanting (Merck 1989), and in making ethylene glycol and ethylene oxide. Exposurerisks to this compound may arise when itis formed from ethylene oxide during thesterilization of grain and spices, drugs, andsurgical supplies. The compound was used inthe past in hastening grape vine sprouting.

Uses

2-Chloroethanol, is used in the preparation of TTFTT (tetrathiafulvalene-2,3,6,7-tetrathiolate) and important building block in TTF syntheis. In addition, it is used in the synthesis of vinyltriazoles. This is the labeled analog.

Uses

Solvent; manufacture of insecticides; treating sweet potatoes before planting.

Definition

ChEBI: A chloroethanol carrying a chloro substituent at position 2.

General Description

2-Chloroethanol is a colorless liquid with an ether-like odor. 2-Chloroethanol is soluble in water and is also a combustible liquid. It reacts with alkali metals.Ethylene chlorohydrine has applications as a laboratory reagent and as a pharmaceutical intermediate. Ethylene chlorohydrine is a building block in the production of pharmaceuticals, biocides, and plasticisers, used for manufacture of thiodiglycol, an important solvent for cellulose acetate and ethyl cellulose, textile-printing dyes, extraction of pine lignin, in dewaxing, refining of rosin, and the cleaning of machines. Several dyes are prepared by the alkylation of aniline derivatives with chloroethanol.

Air & Water Reactions

Highly flammable. 2-Chloroethanol is soluble in water.

Reactivity Profile

Mixing 2-Chloroethanol in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, ethylene diamine, and sodium hydroxide, [NFPA 1991]. Ethylenediamine reacts violently with 2-Chloroethanol. (Lewis, R.J., Sr. 1992. Sax's Dangerous Properties of Industrial Materials, 8th Edition. New York: Van Nostrand Reinhold. pp. 1554.).

Hazard

Deadly via ingestion, inhalation, and skin absorption; strong irritant, penetrates ordinary rubber gloves and protective clothing. Moderate fire hazard. Questionable carcinogen.

Health Hazard

Ethylene chlorohydrin is a severe acute poi son. The target organs are CNS, cardiovascu lar system, kidney, liver, and gastrointestinalsystem. The symptoms of acute toxicity arerespiratory distress, paralysis, brain damage,nausea, and vomiting. In addition, ethylenechlorohydrin can cause glutathione depletionin liver and formation of polyuria in kidney.
Ingestion of 20–25 mL can be fatal tohumans. Death may occur in 48 hours dueto metabolic acidosis and respiratory failure.Ethanol therapy apparently produced no ben efit in treatment (Deng et al. 2001). It maybe more toxic by skin contact than by oralintake. Inhalation of its vapors can producenausea, vomiting, headache, chest pain, andstupor (ACGIH 1986). At high concentra tions, death may occur. Exposure to 300 ppmfor 2 hours can be fatal to humans.
LD50 value, oral (mice): 81 mg/kgLD50 value, intraperitoneal (mice): 97 mg/kg
Ethylene chlorohydrin is an irritant to theskin, eyes, nose, and mucous membranes.It is a confirmed mutagen by the Ames testin Salmonella typhimurium. It inhibits thegrowth of DNA-deficient bacteria. Exposureto this compound increased the chromosomeaberration in the bone marrow of rats. Theodor threshold is 0.4 ppm.
A 2-year dermal study showed no evidenceof carcinogenicity of ethylene chlorohydrin onrodents (NTP 2004). The compound, however,caused malformed fetus and maternal mortality in experimental animals.

Health Hazard

Very toxic; probable oral lethal dose in humans is 50-500 mg/kg or between 1 teaspoon and 1 ounce for a 70 kg (150 lb.) person. Poisoning causes liver and kidney degeneration and irritates mucous membranes; it may be cumulative. Several fatal cases with brain edema and lung edema have been reported from industrial exposure by inhalation and skin contact. It is more toxic by skin contact than orally.

Fire Hazard

2-Chloroethanol decomposition products will react with water or steam to produce toxic and corrosive fumes of phosgene and hydrogen chloride. Vapors are heavier than air and may flash back to a source of ignition.

Chemical Reactivity

Reactivity with Water: No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

: A poison by ingestion, inhalation, skin contact, intraperitoneal, intravenous, and subcutaneous routes. Moderately toxic to humans by inhalation. It can affect the nervous system, liver, spleen, and lungs. An experimental teratogen. Mutation data reported. A severe eye and mild skin irritant. Flammable liquid when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam, CO2, dry chemical. Violent reaction with chlorosulfonic acid, ethylene hamine, sodmm hydroxide. Reacts with water or steam to produce toxic and corrosive fumes. Potentially violent reaction with oxidizing materials. When heated to decomposition it emits highly toxic fumes of Cland phosgene. See also CHLORINATED HYDROCARBONS, ALIPHATIC.

Potential Exposure

Ethylene chlorohydrin is used as a solvent and emulsifier; in the synthesis of ethylene glycol, ethylene oxide, amines, carbitols, indigo, malonic acid, novocaine, and in other reactions where the hydroxyethyl group is introduced into organic compounds; for the separation of butadiene from hydrocarbon mixtures; in dewaxing and removing cycloalkanes from mineral oil; in the refining of rosin; in the manufacture of certain pesticides and in the extraction of pine lignin. In the lacquer industry, it is used as a solvent for cellulose acetate, cellulose esters, resins and waxes; and in the dyeing and cleaning industry, it is used to remove tar spots; as a cleaning agent for machines; and as a solvent in fabric dyeing. It has also found use in agriculture in speeding up sprouting of potatoes and in treating seeds to inhibit biological activity. Making chemical warfare agents

Environmental Fate

Biological. Heukelekian and Rand (1955) reported a 10-d BOD value of 0.50 g/g which is 50.0% of the ThOD value of 1.00 g/g.
Chemical/Physical. Reacts with aqueous sodium bicarbonate solutions at 105 °C producing ethylene glycol (Patnaik, 1992).

Shipping

UN1135 Ethylene chlorohydrin, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquid, Inhalation Hazard Zone B

Purification Methods

Dry it with, then distil it from, CaSO4 in the presence of a little Na2CO3 to remove traces of acid. [Beilstein 1 IV 1372.]

Incompatibilities

May form explosive mixture with air. Strong oxidizers may cause fire and explosions. Incompatible with strong caustics (formation of ethylene gas), strong acids; alkaline metals; aliphatic amines; isocyanates. Violent reaction with ethylene diamine, chlorosulfonic acid. Attacks some plastics, rubber and coatings. Reacts with water or steam producing toxic and corrosive fumes

Waste Disposal

Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced.

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