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Epichlorohydrin information


(±)-Epichlorohydrin[1]
Epichlorohydrin skeletal structure
(R)-Epichlorohydrin
(S)-Epichlorohydrin
Names
Preferred IUPAC name
2-(Chloromethyl)oxirane
Other names
(Chloromethyl)oxirane
Epichlorohydrin
1-Chloro-2,3-epoxypropane
γ-Chloropropylene oxide
Glycidyl chloride
ECH
Identifiers
CAS Number
  • 106-89-8 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
79785
ChEBI
  • CHEBI:37144 checkY
ChEMBL
  • ChEMBL1421613
ChemSpider
  • 13837112 checkY
ECHA InfoCard 100.003.128 Edit this at Wikidata
EC Number
  • 203-439-8
Gmelin Reference
164180
KEGG
  • C14449 checkY
PubChem CID
  • 7835
RTECS number
  • TX4900000
UNII
  • 08OOR508C0 checkY
UN number 2023
CompTox Dashboard (EPA)
  • DTXSID1020566 Edit this at Wikidata
InChI
  • InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2 checkY
    Key: BRLQWZUYTZBJKN-UHFFFAOYSA-N checkY
  • InChI=1/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2
    Key: BRLQWZUYTZBJKN-UHFFFAOYAY
SMILES
  • ClCC1CO1
Properties
Chemical formula
C3H5ClO
Molar mass 92.52 g/mol
Appearance colorless liquid
Odor garlic or chloroform-like
Density 1.1812 g/cm3
Melting point −25.6 °C (−14.1 °F; 247.6 K)
Boiling point 117.9 °C (244.2 °F; 391.0 K)
Solubility in water
7% (20°C)[2]
Vapor pressure 13 mmHg (20°C)[2]
Hazards
GHS labelling:
Pictograms
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Signal word
Danger
Hazard statements
H226, H301, H311, H314, H317, H331, H350
Precautionary statements
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P280, P281, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P321, P322, P330, P333+P313, P361, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
3
2
Flash point 32 °C (90 °F; 305 K)
Explosive limits 3.8–21%[2]
Lethal dose or concentration (LD, LC):
LC50 (median concentration)
3617 ppm (rat, 1 hr)
2165 ppm (rat, 1 hr)
250 ppm (rat, 8 hr)
244 ppm (rat, 8 hr)
360 ppm (rat, 6 hr)[3]
LCLo (lowest published)
250 ppm (rat, 4 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 5 ppm (19 mg/m3) [skin][2]
REL (Recommended)
Carcinogen[2]
IDLH (Immediate danger)
Ca [75 ppm][2]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents.[4] It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive electrophilic compound and is used in the production of glycerol, plastics, epoxy glues and resins, epoxy diluents and elastomers.

  1. ^ Merck Index, 12th Edition, 3648.
  2. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0254". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b "Epichlorohydrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ "EPA consumer factsheet". Epa.gov. Retrieved 2011-12-02.

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Epichlorohydrin

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Epoxy

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with acidic hydroxy groups and epichlorohydrin. First a hydroxy group reacts in a coupling reaction with epichlorohydrin, followed by dehydrohalogenation...

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Glycerol

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to dichlorohydrin, which reacts with a strong base to give epichlorohydrin. Epichlorohydrin can be hydrolyzed to glycerol. Chlorine-free processes from...

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from an acid-catalyzed reaction between 2-methyl-5-nitroimidazole and epichlorohydrin. Antimicrobial spectrum is similar to that of metronidazole and is...

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to some sources— and epichlorohydrin. The structure drawing (top right) shows the DETA moieties in blue and the epichlorohydrin moieties in red. Handelsman...

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corresponding Grignard reagent; this is reacted directly with (S)-epichlorohydrin regioselectively at less-substituted site of the epoxide. A Mitsunobu...

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Trimethylolpropane

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photoinduceable polymerisation initiator. It is may also be reacted with epichlorohydrin to produce the triglycidyl ether. Pentaerythritol Neopentyl glycol...

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Halohydrin

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the production of chlorohydrin precursors to two important epoxides, epichlorohydrin and propylene oxide[citation needed]. At one time, 2-chloroethanol...

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Elastomer

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rubber, a terpolymer of ethylene, propylene and a diene-component) Epichlorohydrin rubber (ECO) Acrylic rubber (ACM, ABR) Silicone rubber (SI, Q, VMQ)...

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Chlorine

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vinylidene chloride, trichloroethylene, perchloroethylene, allyl chloride, epichlorohydrin, chlorobenzene, dichlorobenzenes, and trichlorobenzenes. The major...

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Sephadex

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used for ion-exchange chromatography. Sephadex is crosslinked with epichlorohydrin. Sephadex is used to separate molecules by molecular weight. Sephadex...

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Castor oil

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lubricant. Castor oil may be epoxidized by reacting the OH groups with epichlorohydrin to make the triglycidyl ether of castor oil which is useful in epoxy...

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Propylene

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isopropyl alcohol (propan-2-ol), acrylonitrile, propylene oxide, and epichlorohydrin. The industrial production of acrylic acid involves the catalytic partial...

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Drinking water quality standards

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50 μg/L Copper 2.0 mg/L Cyanide 50 μg/L 1,2-dichloroethane 3.0 μg/L Epichlorohydrin 0.10 μg/L Fluoride 1.5 mg/L Lead 10 μg/L Mercury 1.0 μg/L Nickel 20...

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Ficoll

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from 2 to 7 nm. It is prepared by reaction of the polysaccharide with epichlorohydrin. Ficoll is a registered trademark owned by GE Healthcare companies...

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Trichloroethylene

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formulations. Epichlorohydrin, butylene oxide, N-methylpyrrole and ethyl acetate are common stabilisers for TCE, with epichlorohydrin being the most...

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Vegetable oil

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oil is a precursor to Nylon 11. Castor oil may also be reacted with epichlorohydrin to make a glycidyl ether which is used as a diluent and flexibilizer...

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Isosorbide

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component as well as a chain extender. By reacting isosorbide with epichlorohydrin, isosorbide bis-glycidyl ether (a bis-epoxide) is formed, which could...

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IARC group 2A

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chloride Dimethylformamide 1,2-Dimethylhydrazine Dimethyl sulfate Epichlorohydrin Ethylene dibromide Ethyl carbamate (urethane) N-Ethyl-N-nitrosourea...

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Cyclopropanol

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1016/S0040-4039(00)96204-X. Magrane, J. K.; Cottle, D. L. (1942). "The Reaction of Epichlorohydrin with the Grignard Reagent". J. Am. Chem. Soc. 64 (3): 484–487. doi:10...

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Dow Chemical Company

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Dow manufactures epoxy resin intermediates including bisphenol A and epichlorohydrin. Saran resins and films are based on polyvinylidene chloride (PVDC)...

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Cyanuric acid

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isocyanurate) is formed by reacting cyanuric acid with 3 equivalents of epichlorohydrin. It works by cross-linking DNA. Testing for cyanuric acid concentration...

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Bisphenol A

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workers at I.G. Farbenindustrie reported the coupling of BPA and epichlorohydrin. Over the following decade, coatings and resins derived from similar...

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