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106-89-8 Structure

106-89-8 Structure



AKOS BBS-00004288
(Chloromethyl)ethylene oxide

[Molecular Formula]

[MDL Number]

[Molecular Weight]

[MOL File]

Chemical PropertiesBack Directory

colourless liquid

Epichlorohydrin is a colorless liquid with a slightly irritating, chloroform-like odor.
[Melting point ]

-57 °C
[mp ]

-57 °C
[alpha ]

[Boiling point ]

115-117 °C(lit.)
[bp ]

115-117 °C(lit.)
[density ]

1.183 g/mL at 25 °C(lit.)
[vapor density ]

3.2 (vs air)
[vapor pressure ]

13.8 mm Hg ( 21.1 °C)
[refractive index ]

n20/D 1.438(lit.)
[Fp ]

93 °F
[storage temp. ]

Refrigerator (+4°C) + Flammables area
[solubility ]

[form ]

[color ]

APHA: ≤20
[Specific Gravity]

1.183 (20/4℃)

Pungent, garlic; sweet, pungent; like chloroform.

Stability Unstable. Flammable-note wide explosion limits and low flash point. Vapours may flow along surfaces to source of ignition. Contact with strong oxidisers may lead to fire. Incompatible with strong acids, strong bases, strong oxidizing agents, metal salts, amines, aluminium, chlorine and a variety of chlorine compounds, most com
[explosive limit]

[Water Solubility ]

6 g/100 mL (10 ºC)
[FreezingPoint ]

[Merck ]

[BRN ]

[Henry's Law Constant]

3.42(x 10-5 atm?m3/mol) at 25 °C (static headspace-GC, Welke et al., 1998)
[Exposure limits]

TLV-TWA(skin) 8 mg/m3 (2 ppm) (ACGIH); STEL (15 min) 19 mg/m3 (5 ppm) (NIOSH).
[Contact allergens]

Epoxy resin of the Bisphenol A type is synthesized from epichlorhydrin and bisphenol A. It leads to bisphenol A diglycidyl ether, which is the monomer ofbisphenol-A-based epoxy resins. Sensitization to epichlorhydrin occurs mainly in workers of the epoxy resin industry. Sensitization in individuals not working at epoxy resin plants is rare. It has, however, been described to occur following exposure to a soil fumigant, due to solvent cement, and in a worker in a pharmaceutical plant, in a division of drug synthesis. Epichlorhydrin was used for the production of drugs propranolol and oxprenolol.
[CAS DataBase Reference]

106-89-8(CAS DataBase Reference)

2A (Vol. 11, Sup 7, 71) 1999
[NIST Chemistry Reference]

Oxirane, (chloromethyl)-(106-89-8)
[EPA Substance Registry System]

106-89-8(EPA Substance)
Hazard InformationBack Directory
[Chemical Properties]

colourless liquid

ChEBI: An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.

Solvent for natural and synthetic resins, gums, cellulose esters and ethers, paints, varnishes, nail enamels and lacquers, cement for Celluloid. As stabilizer.
[General Description]

A clear colorless liquid with an irritating chloroform-like odor. Density 9.8 lb/gal. Flash point 87°F. Polymerizable. If polymerization takes place inside a closed container, the container is subject to violent rupture. Irritates the skin and respiratory system. Toxic by ingestion. A confirmed carcinogen. Vapors heavier than air. Used to make plastics and as a solvent.
[Reactivity Profile]

1-CHLORO-2,3-EPOXYPROPANE(106-89-8) may polymerize exothermically if heated or contaminated. Reacts explosively with aniline. Ignites on contact with potassium tert-butoxide. Reacts with trichloroethylene to give the explosive dichloroacetylene. Violent reaction with sulfuric acid or isopropylamine. Exothermic polymerization on contact with strong acids or bases, zinc, aluminum, aluminum chloride, iron, ferric chloride [Sax, 9th ed., 1996, p. 1469].
[Air & Water Reactions]

Highly flammable. Water soluble.

Toxic by inhalation, ingestion, and skin absorption; strong irritant, a carcinogen. Flammable, moderate fire risk. TLV: 0.5 ppm; animal carcinogen.
[Health Hazard]

This compound is caustic as both a liquid and gas. Irritation of the eyes and skin, and skin sensitization has been observed. Exposure to epichlorohydrin has caused inflammation of the lungs, asthmatic bronchitis, and liver and kidney damage. In acute poisonings, death may be caused by respiratory paralysis.
[Potential Exposure]

Epichlorohydrin, an organochlorine, is used in the manufacture of many glycerol and glycidol derivatives and epoxy resins; as a stabilizer in chlorine-containing materials; as an intermediate in the preparation of cellulose esters and ethers, paints, varnishes, nail enamels, and lacquers; as a cement for celluloid. It is used as an intermediate in the manufacture of various drugs. Increased cancer risk.
[Fire Hazard]

When heated to decomposition, this compound evolves highly toxic fumes of phosgene and carbon monoxide. Reactive and incompatible with strong oxidizers, strong acids, caustics, zinc, aluminum, chlorides of iron and aluminumand compounds with an active hydrogen atom, including water. Unstable, avoid heat, contaminants, strong acids and bases, certain curing agents such as ethylenediamine. Hazardous polymerization may occur.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy

UN2023 Epichlorhydrin, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable liquid.

May form explosive mixture with air. Slowly decomposes on contact with water. Heat or strong acids; alkalies, metallic halides, or contaminants can cause explosive polymerization. Violent reaction with strong oxidizers, aliphatic amines; alkanolamines, amines (especially aniline), alkaline earths; chemically active metals (chlorides of aluminum, iron zinc); powdered metals (aluminum, zinc); alcohols, phenols, organic acids; causing fire and explosion hazard. Will pit steel in the presence of water. Thermal decomposition forms highly toxic phosgene gas. May accumulate static electrical charges, and may cause ignition of its vapors.
[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. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≧100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal
[Physical properties]

Clear, colorless, mobile liquid with a strong, irritating, chloroform-like odor. Odor threshold concentration is 0.93 ppm (quoted, Amoore and Hautala, 1983).
[Production Methods]

Epichlorohydrin can be prepared from 1,3-dichloropropanol-2, 2,3- dichloropropanol-1, or allyl chloride. Commercially it is prepared as an intermediate in glycerol synthesis via alkaline hydrolysis of glycerol dichlorohydrin. Both come from allyl chloride. Epichlorohydrin reacts with monohydric alcohols to give ethers by opening the oxide ring. It will react with ethers, aldehydes, ketones, organic acids and amines to give a wide variety of useful syntheses.
[Synthesis Reference(s)]

Organic Syntheses, Coll. Vol. 2, p. 256, 1943
The Journal of Organic Chemistry, 48, p. 3831, 1983 DOI: 10.1021/jo00169a052
[Chemical Reactivity]

Reactivity with Water Mild reaction; not likely to be hazardous; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Can polymerize in presence of strong acids and bases, particularly when hot; Inhibitor of Polymerization: None used.

Epichlorohydrin is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Epichlorohydrin is stored in a well-ventilated,cool place isolated from combustible andoxidizable materials, all acids and bases,and anhydrous metal halides. Protect fromphysical damage. It is shipped in metaldrums.
[Purification Methods]

Distil epichlorohydrin under atmospheric pressure, heat it on a steam bath with one-quarter its weight of CaO, then decant and fractionally distil it. [Beilstein 17 V 20.]
[Toxicity evaluation]

Epichlorohydrin is an alkylating agent that is mutagenic. It may induce DNA interstrand cross-links, chromosomal aberrations, and breaks. It is also an irritant, sensitizer, and corrosive.
Safety DataBack Directory
[Hazard Codes ]

[Risk Statements ]

R45:May cause cancer.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R34:Causes burns.
R43:May cause sensitization by skin contact.
[Safety Statements ]

S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .

UN 2023 6.1/PG 2
[WGK Germany ]


[Autoignition Temperature]

779 °F

[HazardClass ]

[PackingGroup ]

[HS Code ]

[Safety Profile]

Confirmed carcinogen with experimental carcinogenic data. Poison by ingestion, skin contact, intravenous, and intraperitoneal routes. Moderately toxic by inhalation. An experimental teratogen. Other experimental reproductive effects. Human systemic effects by inhalation: respiratory, nose, and eyes. Human mutation data reported. A skin and eye irritant. A sensitizer. Flammable liquid when exposed to heat or flame. Explosive reaction with andine. Reaction with trichloroethylene forms the explosive dichloroacetylene. Ignition on contact with potassium tertbutoxide. Violent reaction with sulfuric acid or isopropylamine. Exothermic polymerization on contact with strong acids, caustic alkalies, aluminum, aluminum chloride, iron(II1) chloride, or zinc. When heated to decomposition it emits toxic fumes of Cl
[Hazardous Substances Data]

106-89-8(Hazardous Substances Data)

LD50 orally in rats: 0.09 g/kg (Smyth, Carpenter)
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Sodium hydroxide-->Acetic acid-->Sodium carbonate-->Chlorine-->Calcium carbonate-->Oxygen-->Allyl chloride-->PROPYLENE-->hypochlorous acid-->2-Amino-3-chlorobenzoic acid-->D-D Extender-->2,3-DICHLORO-1-PROPANOL
【Preparation Products】

softening agent EST-->3-AMINO-1-PHENOXY-2-PROPANOL HYDROCHLORIDE-->softening agent SCI-A-->noncyanide zinc plating additive-TDAE-->wet strength agent used for paper PAE-->2,3-DIHYDRO-1,4-BENZODIOXIN-2-METHANOL 4-METHYLBENZENESULFONATE-->Ethylene glycol diglycidyl ether-->DL-Carnitine hydrochloride-->1,3,5-Triglycidyl isocyanurate-->zinc plating additive DPE-1-->1-CHLORO-3-FLUOROISOPROPANOL-->CARAZOLOL HCL-->mnocyanide zine plating bright agent-->2-HYDROXYMETHYL-1,4-BENZODIOXANE-->[[p-(2-methoxyethyl)phenoxy]methyl]oxirane-->noncyanide zinc plating additive XD-1-->GLYCIDYL ISOPROPYL ETHER-->ironicion stabilzer-->2-GLYCIDYLOXYBENZONITRILE-->1,4-bis[(3-chloro-2-hydroxypropyl)amino]anthraquinone-->Noncyanide zinc plating additive DE-->Cross-linking agent DE-->BE-strong efficient nickel plating brightener-->Guaiacol glycidyl ether-->2-[(1-Naphthyloxy)methyl]oxirane-->Glycidyl phenyl ether-->N-(4-(OXIRANYLMETHOXY)-1,2-EPOXYPROPANE-->the chelating resin of crosslinking chitosan condense with salilylaldehyde-->Metoprolol-->1,3-diiodopropan-2-ol-->Poly(epichlorohydrin-co-propylene oxide-co-starch)-->noncyanide zinc plating bright additive-->4-(oxiranylmethoxy)-1H-indole-->3-Chloro-2-hydroxypropyltrimethyl ammonium chloride-->noncyanide zie plating additive XD-2-->1-(2-Hydroxy-3-sulfopropyl)-pyridinium betane-->L-Carnitine hydrochloride-->Acetyl-L-carnitine hydrochloride-->L-Carnitine fumarate
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Questions And AnswerBack Directory

Epichlorohydrin is a kind of organochlorine compound as well as epoxide. It can be used as an industrial solvent. It is a highly reactive compound, and can be used for the production of glycerol, plastics, epoxy glues and resins, and elastomers. It can also be used for the production of glycidyl nitrate and alkali chloride, used as the solvent of cellulose, resins, and paint as well as being used as an insect fumigant. In biochemistry, it can be used as a crosslinking agent for the production of Sephdex size-exclusion chromatography resins. However, it is a potential carcinogen, and can cause various kinds of side effects on respiratory tract and kidneys. It can be manufactured through the reaction between allyl chloride with hypochlorous acid as well as alcohols.
[Chemical Properties]

Epichlorohydrin (molecular weight = 92.53 g/mol) is a colorless liquid with a sweet or garlic-like pungent odor. It is soluble in water (6.6 × 104 mg/l at 25 °C) and miscible with most organic solvents.

Epichlorohydrin is mainly used in the production of epoxy resins. It was also used as a solvent for paints, varnishes, lacquers, cellulose esters and ethers, and gums. Epichlorohydrin was historically used as an insecticide fumigant.
[Environmental Fate]

Epichlorohydrin may be found in the environment as a result of release in waste streams of resin, paint and lacquer, cellulose ester/ether, and gum production. The high vapor pressure of epichlorohydrin maintains it as a gas in the atmosphere, where it is degraded by photochemically produced hydroxyl radicals (half-life=36 days). Epichlorohydrin is highly mobile in soil, evaporates quickly from dry soil, and is extensively hydrolyzed in moist soil and water. It is not expected to be adsorbed to sediments and suspended particles and is not expected to bioaccumulate in aquatic organisms(NLM, 2013).
Spectrum DetailBack Directory
[Spectrum Detail]

Epichlorohydrin(106-89-8) 13C NMR
Epichlorohydrin(106-89-8) MS
Epichlorohydrin(106-89-8) IR2
Epichlorohydrin(106-89-8) 1H NMR
Epichlorohydrin(106-89-8) Raman
Epichlorohydrin(106-89-8) IR1
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Epichlorohydrin, 99%(106-89-8)
[Alfa Aesar]

(+/-)-Epichlorohydrin, 99%(106-89-8)
[Sigma Aldrich]


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