Epichlorohydrin

An ether, C3H5ClO, 92.525 g/mol. Boiling point 117.9 °C, melting point -25.6 °C, as published.

verified recordOrganic — ether9 measured properties

Identifiers

Molecular formula: C₃H₅ClO
Molecular weight: 92.525 g/mol
Exact mass: 92.002892 g/mol
SMILES: ClCC1CO1
InChI: InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2
InChIKey: BRLQWZUYTZBJKN-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point: 241.7 °F at 760 mmHg (EPA, 1998)measured · U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.; 117.9 °Cmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 616; 116 °Cmeasured · reference compound database; 242 °Fmeasured · reference compound database; 117.9 °C @760 [mm Hg]measured · reference compound database; 242 °Fmeasured · reference compound database
Melting Point: -54.4 to -14.1 °F (EPA, 1998)measured · U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.; -25.6 °Cmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 616; -57.2 °Cmeasured · reference compound database; -48 °Cmeasured · reference compound database; -54 °Fmeasured · reference compound database; -25.6 °Cmeasured · reference compound database; -54 °Fmeasured · reference compound database
Flash Point: 93 °F (EPA, 1998)measured · U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.; 88 °Fmeasured · reference compound database; 88 °F (31 °C) (Closed cup)measured · Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 325-46; 31 °C c.c.measured · reference compound database; 93 °Fmeasured · reference compound database; 93 °Fmeasured · reference compound database
Solubility: 50 to 100 mg/mL at 72 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; Miscible with most organic solventsmeasured · Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 505; Miscible with alcohol, ether, chloroform, trichloroethylene, carbon tetrachloride; immiscible with petroleum hydrocarbons.measured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 616; In water, 6.59X10+4 mg/L at 25 °Cmeasured · Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility. Fifth ed, Tucson, AZ: Univ AZ, College of Pharmacy (1992); 65.9 mg/mL at 25 °Cmeasured · reference compound database; Solubility in water, g/100ml at 20 °C: 6measured · reference compound database; 7%measured · reference compound database
Density: 1.18 to 1.801 at 68 °F (EPA, 1998)measured · U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.; 1.1750 at 25 °C/4 °Cmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 616; Relative density (water = 1): 1.2measured · reference compound database; 1.18measured · reference compound database; 1.175 @25 °Cmeasured · reference compound database; 1.18measured · reference compound database
Vapor Pressure: 10 mmHg at 61.88 °F (EPA, 1998)measured · U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.; 16.4 [mmHg]measured · reference compound database; 16.4 mm Hg at 25 °Cmeasured · Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.; Vapor pressure, kPa at 20 °C: 1.6measured · reference compound database; 13 mmHgmeasured · reference compound database; 16.4 [mm Hg] @25 °Cmeasured · reference compound database; 13 mmHgmeasured · reference compound database
LogP: log Kow = 0.45measured · Deneer JW et al; Aquat Toxicol 13: 195-204 (1988); 0.45measured · reference compound database; 0.26measured · reference compound database; 0.45measured · reference compound database
Viscosity: 0.0103 poise at 25 °Cmeasured · Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 449
Refractive Index: Index of refraction: 1.44195 at 11.6 °C/D; 1.43969 at 16 °C/D; 1.43585 at 25 °C/Dmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 616

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

logP: 0.624calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 12.53 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 0calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 1calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 1calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 20.46 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 1calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.3414calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon3 atoms · 38.9% by mass
Cl Chlorine1 atom · 38.3% by mass
O Oxygen1 atom · 17.3% by mass
H Hydrogen5 atoms · 5.4% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 5
Total atoms, hydrogen included: 10
Rings: 1
Aromatic rings: 0
Stereocentres: 1
Formal charge: 0

Functional groups

Ether
An oxygen bridging two carbons.
Halide (C–X)
A halogen atom attached to carbon.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Epichlorohydrin yet.

Other names for it

No systematic name is recorded.

The sources also call it 2-(Chloromethyl)oxirane, Epichlorhydrin, 1-Chloro-2,3-epoxypropane, Glycidyl chloride, Epichlorhydrine, Chloromethyloxirane, Oxirane, (chloromethyl)-, Chloropropylene oxide, 2,3-Epoxypropyl chloride, Epichloorhydrine, (CHLOROMETHYL)OXIRANE, 1,2-Epoxy-3-chloropropane.

Structurally related

Nothing structurally close to Epichlorohydrin has a page here yet.

Seen alongside it in reaction records

Molecules that appear in the same recorded reactions as Epichlorohydrin. This says nothing about structure: most of them are the bases, solvents, ligands and catalysts the chemistry needed, and they are here because somebody put them in the same flask.

(4-Methoxyphenyl)-(4-hydroxyphenyl)-naphth-1-yl-methane

used as a reactant

C₂₄H₂₀O₂, 340.422 g/mol.

(4-Methoxyphenyl)-(4-(2,3-epoxy-propyloxy)phenyl)-5,6,7,8-tetrahydronaphth-1-yl-methane

formed as a product

C₂₇H₂₈O₃, 400.518 g/mol.

1,2-Dichloroethane

used as a reactant

C₂H₄Cl₂, 98.96 g/mol.

Where these values came from

chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.