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Epichlorohydrin

Athanor · official

C3H5ClO · 92.52 g/mol

IUPAC name: 2-(chloromethyl)oxirane

Also called chloromethyloxirane, epoxy resin monomer

Open in Athanor
The structure of Epichlorohydrin
Drawn from its SMILES with RDKit332 ̵W̵
FlammableCorrosiveAcute toxicityHealth hazardDangerFlammable liquid and vapor · Toxic if swallowed · Toxic in contact with skin · Causes severe skin burns and eye damage · May cause an allergic skin reaction · Toxic if inhaled · May cause cancer

Names and identifiers

IUPAC name
2-(chloromethyl)oxirane
Synonyms
chloromethyloxirane, epoxy resin monomer, 2-(Chloromethyl)oxirane
+ 37 more

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, 3-Chloro-1,2-epoxypropane, Glycerol epichlorhydrin, Glycerol epichlorohydrin, 3-Chloropropylene oxide, alpha-Epichlorohydrin, (Chloromethyl)ethylene oxide, 3-Chloro-1,2-propylene oxide, Epicloridrina, Epichlorohydryna, Epichlorophydrin, SKEKhG, epi-Chlorohydrin, 3-Chloropropene-1,2-oxide, Oxirane, 2-(chloromethyl), gamma-Chloropropylene oxide, 1-Cloro-2,3-epossipropano, 1-Chlor-2,3-epoxy-propan, (RS)-3-chloro-1,2-epoxypropane, 1-Chloor-2,3-epoxy-propaan, Rcra waste number U041, DL-a-Epichlorohydrin, DTXSID1020566, NCI-C07001, NSC-6747, 08OOR508C0, (DL)-alpha-Epichlorohydrin

Molecular formula
C3H5ClO
Empirical formula
C3H5ClO
Molecular weight
92.52 g/mol
Exact mass
92.00289
CAS number
106-89-8
PubChem CID
7835
Canonical SMILES
C1C(O1)CCl
Isomeric SMILES
C1C(O1)CCl
InChI
InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2
InChIKey
BRLQWZUYTZBJKN-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

TemperaturePressureDensity
Appearance
Colorless liquid[6]
6 values

From Hazardous Substances Data Bank (HSDB), the most authoritative source here.

ValueAs writtenSource
–1-chloro-2,3-epoxypropane appears as 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.[1] CAMEO Chemicals
–Liquid; Gas Vapor; Liquid[2] EPA Chemical Data Reporting (CDR)
–COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.[3] ILO-WHO International Chemical Safety Cards (ICSCs)
–Colorless liquid with a slightly irritating, chloroform-like odor.[4] Occupational Safety and Health Administration (OSHA)
–Colorless liquid with a slightly irritating, chloroform-like odor.[5] The National Institute for Occupational Safety and Health (NIOSH)
–shownColorless liquid[6] Hazardous Substances Data Bank (HSDB)cites NIOSH. NIOSH Pocket Guide to Chemical Hazards & Other Databases CD-ROM. Department of Health & Human Services, Centers for Disease Prevention & Control. National Institute for Occupational Safety & Health. DHHS (NIOSH) Publication No. 2005-151 (2005)
Odor
Pungent, garlic-like odor[6]
2 values

From Hazardous Substances Data Bank (HSDB), the most authoritative source here.

ValueAs writtenSource
–Odor is sweet, pungent or chloroform-like ... generally perceived as a slightly irritating chloroformlike odor[6] Hazardous Substances Data Bank (HSDB)cites Waechter JM Jr, Veenstra GE; Patty's Toxicology. (2007). NY, NY: John Wiley & Sons, Inc. Epoxy Compounds - Aromatic diglycidyl ethers, polyglycidyl ethers, glycidyl ethers, and miscellaneous epoxy compounds. On-line posting date: Apr 16, 2001.
–shownPungent, garlic-like odor[6] Hazardous Substances Data Bank (HSDB)cites US EPA; Consumer Factsheet on: Epichlorohydrin. Washington, DC: US EPA, Off Ground Water and Drinking Water. Available from, as of May 22, 2009. https://www.epa.gov/safewater/dwh/c-voc/epichlor.html
Melting point
-48.0 to -25.6 °C (-54.4 to -14.1 °F, EPA 1998)[1]
5 values

4 of 5 sources agree on it (most common value).

ValueAs writtenSource
−48.0 to −25.6 °Cshown-54.4 to -14.1 °F (EPA, 1998)[1] CAMEO Chemicalscites 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.
−48 °C-48 °C[3] ILO-WHO International Chemical Safety Cards (ICSCs)
−48 °C-54 °F[4] Occupational Safety and Health Administration (OSHA)
−25.6 °C-25.6 °C[7] PAC Chemical Database, U.S. Department of Energy
−48 °C-54 °F[5] The National Institute for Occupational Safety and Health (NIOSH)
Boiling point
116.5 °C (241.7 °F) at 760 mmHg (EPA, 1998)[1]
5 values

5 of 5 sources agree on it (most common value).

ValueAs writtenSource
116.5 °Cshown241.7 °F at 760 mmHg (EPA, 1998)[1] CAMEO Chemicalscites 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.
116 °C116 °C[3] ILO-WHO International Chemical Safety Cards (ICSCs)
117 °C242 °F[4] Occupational Safety and Health Administration (OSHA)
117.9 °C117.9 °C @760 [mm Hg][7] PAC Chemical Database, U.S. Department of Energy
117 °C242 °F[5] The National Institute for Occupational Safety and Health (NIOSH)
Density
1.175 @25 °C[7]
5 values

5 of 5 sources agree on it (most common value).

ValueAs writtenSource
–1.18 to 1.801 at 68 °F (EPA, 1998)[1] CAMEO Chemicalscites 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.
–Relative density (water = 1): 1.2[3] ILO-WHO International Chemical Safety Cards (ICSCs)
–1.18[4] Occupational Safety and Health Administration (OSHA)
–shown1.175 @25 °C[7] PAC Chemical Database, U.S. Department of Energy
–1.18[5] The National Institute for Occupational Safety and Health (NIOSH)
Solubility in water
Solubility in water, g/100ml at 20 °C: 6[3]
5 values

From ILO-WHO International Chemical Safety Cards (ICSCs), the most authoritative source here.

ValueAs writtenSource
–50 to 100 mg/mL at 72 °F (NTP, 1992)[1] CAMEO Chemicalscites 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 solvents[6] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 505
–In water, 6.59X10+4 mg/L at 25 °C[6] Hazardous Substances Data Bank (HSDB)cites Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of Aqueous Solubility. Fifth ed, Tucson, AZ: Univ AZ, College of Pharmacy (1992)
–shownSolubility in water, g/100ml at 20 °C: 6[3] ILO-WHO International Chemical Safety Cards (ICSCs)
–7%[5] The National Institute for Occupational Safety and Health (NIOSH)
log P
0.26[3]
2 values

Sources disagree; from ILO-WHO International Chemical Safety Cards (ICSCs), the most authoritative.

ValueAs writtenSource
–log Kow = 0.45[6] Hazardous Substances Data Bank (HSDB)cites Deneer JW et al; Aquat Toxicol 13: 195-204 (1988)
–shown0.26[3] ILO-WHO International Chemical Safety Cards (ICSCs)
Vapor pressure
16.4 mmHg at 25 °C[6]
4 values

2 of 4 sources agree on it (most common value).

ValueAs writtenSource
10 mmHg10 mmHg at 61.88 °F (EPA, 1998)[1] CAMEO Chemicalscites 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 mmHgshown16.4 mm Hg at 25 °C[6] Hazardous Substances Data Bank (HSDB)cites Daubert, T.E., R.P. Danner. Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis, 1989.
12 mmHgVapor pressure, kPa at 20 °C: 1.6[3] ILO-WHO International Chemical Safety Cards (ICSCs)
16.4 mmHg16.4 [mm Hg] @25 °C[7] PAC Chemical Database, U.S. Department of Energy

2 more values were reported but failed the checks (unreadable or out of range), so they are not shown.

Flash point
34 °C (93 °F, EPA 1998)[1]
5 values

3 of 5 sources agree on it (most common value).

ValueAs writtenSource
34 °Cshown93 °F (EPA, 1998)[1] CAMEO Chemicalscites 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.
31 °C88 °F (31 °C) (Closed cup)[6] Hazardous Substances Data Bank (HSDB)cites Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 325-46
31 °C31 °C c.c.[3] ILO-WHO International Chemical Safety Cards (ICSCs)
34 °C93 °F[4] Occupational Safety and Health Administration (OSHA)
34 °C93 °F[5] The National Institute for Occupational Safety and Health (NIOSH)
Autoignition temperature
411 °C (772 °F)[6]
3 values

2 of 3 sources agree on it (most common value).

ValueAs writtenSource
411 °C772 °F (USCG, 1999)[1] CAMEO Chemicalscites U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
411 °Cshown772 °F (411 °C)[6] Hazardous Substances Data Bank (HSDB)cites Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 325-46
385 °C385 °C[3] ILO-WHO International Chemical Safety Cards (ICSCs)
Viscosity
Reported, but no value passed the checks.
The value and why
  • 0.0103 poise at 25 °C (could not be read; source [6])

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms
5
Rings
1
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
1
H-bond donors
0
H-bond acceptors
1
Rotatable bonds
1
TPSA (Ų)
12.5
Formal charge
0
XLogP3
0.5 PubChem
Complexity
37 PubChem
Stereocenters
0 defined, 1 undefinedCIP: C3: undefined
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C38.94%
  • H5.45%
  • Cl38.32%
  • O17.29%

Isotope pattern

100%92.0033.3%93.00632%94.0001.1%95.003

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
0.62 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-0.74 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.45 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 92.53
  • log P ≤ 5 (Crippen): 0.62
  • H-bond donors ≤ 5: 0
  • H-bond acceptors ≤ 10: 1

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Danger

Harmonized EU classification (CLP Annex VI). Source [8].

  • Flammable
  • Corrosive
  • Acute toxicity
  • Health hazard
332 ̵W̵
NFPA 704[6]
  • H226Flammable liquid and vapor
  • H301Toxic if swallowed
  • H311Toxic in contact with skin
  • H314Causes severe skin burns and eye damage
  • H317May cause an allergic skin reaction
  • H331Toxic if inhaled
  • H350May cause cancer

Precautionary statements: P203, P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P272, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P318, P321, P330, P333+P317, P361+P364, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, P501

View all classifications (3)
  • [8] Regulation (EC) No 1272/2008 of the European Parliament and of the Council · DangerH226, H301, H311, H314, H317, H331, H350
  • [9] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1920) of reports.
  • [9] European Chemicals Agency (ECHA) · 1,920 reports · DangerH301+H311+H331, H301+H331, H318, H330, H331, H350, H361, H361f, H412

Exposure limits

  • PEL-TWA (8-Hour Time Weighted Average): 5 ppm (19 mg/m³)[4]
  • PEL: TWA 5 ppm (19 mg/m3) [skin] See Appendix G[5]
  • REL: Ca See Appendix A[5]
  • TLV: 0.5 ppm as TWA; (skin); A3 (confirmed animal carcinogen with unknown relevance to humans).[3]
  • IDLH: 75 ppm ; A potential occupational carcinogen. (NIOSH, 2024)[1]
  • IDLH: NIOSH has recommended that epichlorohydrin be treated as a potential occupational carcinogen.[6]

First aid

  • Warning: Effects may be delayed for several hours. Caution is advised. Signs and Symptoms of Acute Epichlorohydrin Exposure: Acute exposure to epichlorohydrin may result in nausea, vomiting, and abdominal pain. Liver and kidney effects may be observed. The respiratory tract may become irritated, dyspnea (shortness of breath) may occur, and in acute cases, respiratory paralysis has been observed. Central nervous system and respiratory depression have been noted.[1]
  • General First Aid: · Call 911 or emergency medical service. · Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination. · Move victim to fresh air if it can be done safely. · Administer oxygen if breathing is difficult. · If victim is not breathing: -- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance. -- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped…[10]
  • (General first aid procedures) Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Skin: Soap wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with soap and water.[5]
  • Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer immediately for medical attention.[3]

Storage

  • Fireproof. Separated from strong oxidants, acids, bases, aluminium, zinc, amines and food and feedstuffs. Well closed.[3]
  • Separate from acids, alkalies, salts, water, and oxidizers. Store in a cool, dry, well-ventilated location. Inside storage should be in a standard flammable liquids storage warehouse, room, or cabinet.[6]
  • (store at) ambient temperature[6]
  • Precautions FOR "carcinogens": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... Expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... Should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... Should be contiguous to storage area. (chemical Carcinogens)[6]

Incompatibilities

  • Strong oxidizers, strong acids, certain salts, caustics, zinc, aluminum, water [Note: May polymerize in presence of strong acids and bases particularly when hot.].[6]
  • Epichlorohydrin can violently react with compounds carrying an active hydrogen atom, including water.[6]
  • Epichlorohydrin liberates heat in the presence of ... Alkalis, and certain salts ...[6]
  • WITH SLOW mixing (OF epichlorohydrin & isopropylamine) & adequate cooling, smooth condensation TO 1-chloro-3-isopropylamino-2-propanol occurs. WITH rapid mixing & POOR cooling, variable induction period ... SLOW warming precedes rapid, violent exotherm (TO 350 °C IN 6 SEC). Other primary & secondary amines behave similarly.[6]

Safety data sheets on the supplier’s page: INTERBIOSCREEN, Thermo Fisher Scientific, Chem-Impex.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]CAMEO Chemicals · Public domain (NOAA) · via PubChem · retrieved 2026-10-14
  2. [2]EPA Chemical Data Reporting (CDR) · Public domain (US EPA) · via PubChem · retrieved 2026-10-14
  3. [3]ILO-WHO International Chemical Safety Cards (ICSCs) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  4. [4]Occupational Safety and Health Administration (OSHA) · Public domain (US DOL) · via PubChem · retrieved 2026-10-14
  5. [5]The National Institute for Occupational Safety and Health (NIOSH) · Public domain (US CDC) · via PubChem · retrieved 2026-10-14
  6. [6]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
  7. [7]PAC Chemical Database, U.S. Department of Energy · Public domain (US DOE) · via PubChem · retrieved 2026-10-14
  8. [8]Regulation (EC) No 1272/2008 of the European Parliament and of the Council · EU reuse policy, CC BY 4.0 · via PubChem · retrieved 2026-10-14
  9. [9]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  10. [10]Emergency Response Guidebook (ERG) · Public domain (US DOT) · via PubChem · retrieved 2026-10-14
  11. [11]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  12. [12]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  13. [13]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  14. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  15. ·Literature on PubChem

Data last updated 2026-10-14.