Epichlorohydrin
Athanor · official
C3H5ClO · 92.52 g/mol
IUPAC name: 2-(chloromethyl)oxirane
Also called chloromethyloxirane, epoxy resin monomer
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
- Appearance
- Colorless liquid[6]
6 values
From Hazardous Substances Data Bank (HSDB), the most authoritative source here.
Value As written Source – 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) –shown Colorless 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.
Value As written Source – 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. –shown Pungent, 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).
Value As written Source −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).
Value As written Source 116.5 °Cshown 241.7 °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 °C 116 °C [3] ILO-WHO International Chemical Safety Cards (ICSCs) 117 °C 242 °F [4] Occupational Safety and Health Administration (OSHA) 117.9 °C 117.9 °C @760 [mm Hg] [7] PAC Chemical Database, U.S. Department of Energy 117 °C 242 °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).
Value As written Source – 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) –shown 1.175 @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.
Value As written Source – 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) –shown Solubility 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.
Value As written Source – log Kow = 0.45 [6] Hazardous Substances Data Bank (HSDB)cites Deneer JW et al; Aquat Toxicol 13: 195-204 (1988) –shown 0.26 [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).
Value As written Source 10 mmHg 10 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 mmHgshown 16.4 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 mmHg Vapor pressure, kPa at 20 °C: 1.6 [3] ILO-WHO International Chemical Safety Cards (ICSCs) 16.4 mmHg 16.4 [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).
Value As written Source 34 °Cshown 93 °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 °C 88 °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 °C 31 °C c.c. [3] ILO-WHO International Chemical Safety Cards (ICSCs) 34 °C 93 °F [4] Occupational Safety and Health Administration (OSHA) 34 °C 93 °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).
Value As written Source 411 °C 772 °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 °Cshown 772 °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 °C 385 °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
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
- 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
- NMRHazardous Substances Data Bank (HSDB)
- 1H NMRHuman Metabolome Database (HMDB) (JEOL · 90 MHz · CDCl3) · SpectraBase (BRUKER AC-300)
- 13C NMRHuman Metabolome Database (HMDB) (NEVA · 15.09 MHz · CDCl3) · SpectraBase
- 17O NMRSpectraBase
- GC-MSNIST Mass Spectrometry Data Center · NIST Mass Spectrometry Data Center · NIST Mass Spectrometry Data Center · NIST Mass Spectrometry Data Center · SpectraBase (CH5)
- Other MSHazardous Substances Data Bank (HSDB)
- IRHazardous Substances Data Bank (HSDB)
- FTIRSpectraBase (BETWEEN SALTS)
- ATR-IRSpectraBase (ATR-Neat)
- Near IRSpectraBase (BRUKER IFS 88 · NIR Spectrometer= INSTRUMENT PARAMETERS=INST=BRUKER,RSN=19518,REO=2,CNM=HEI,ZFF=2)
- Vapor Phase IRSpectraBase (Bruker IFS 85 · Gas-GC)
- RamanHazardous Substances Data Bank (HSDB) · SpectraBase
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]CAMEO Chemicals · Public domain (NOAA) · via PubChem · retrieved 2026-10-14
- [2]EPA Chemical Data Reporting (CDR) · Public domain (US EPA) · via PubChem · retrieved 2026-10-14
- [3]ILO-WHO International Chemical Safety Cards (ICSCs) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- [4]Occupational Safety and Health Administration (OSHA) · Public domain (US DOL) · via PubChem · retrieved 2026-10-14
- [5]The National Institute for Occupational Safety and Health (NIOSH) · Public domain (US CDC) · via PubChem · retrieved 2026-10-14
- [6]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
- [7]PAC Chemical Database, U.S. Department of Energy · Public domain (US DOE) · via PubChem · retrieved 2026-10-14
- [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]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [10]Emergency Response Guidebook (ERG) · Public domain (US DOT) · via PubChem · retrieved 2026-10-14
- [11]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [12]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [13]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.
