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Aziridine

Athanor · official

C2H5N · 43.07 g/mol

Also called ethylenimine, azacyclopropane

Open in Athanor
The structure of Aziridine
Drawn from its SMILES with RDKit343
FlammableCorrosiveAcute toxicityHealth hazardDangerHighly Flammable liquid and vapor · Fatal if swallowed · Fatal in contact with skin · Causes severe skin burns and eye damage · Fatal if inhaled · May cause genetic defects · May cause cancer · Toxic to aquatic life with long lasting effects

Names and identifiers

IUPAC name
aziridine
Synonyms
ethylenimine, azacyclopropane, ETHYLENEIMINE
+ 36 more

Ethylenimine, Azacyclopropane, Dimethyleneimine, Dihydroazirene, Azirane, Aziran, Aethylenimin, Dihydroazirine, Ethyleenimine, Aziridin, Etilenimina, Dihydro-1H-azirine, 1H-Azirine, dihydro-, Dimethylenimine, RCRA waste number P054, ENT-50324, TL 337, DTXSID8020599, 54P5FEX9FH, CHEBI:30969, RefChem:596749, DTXCID00599, 205-793-9, Ethylene imine, Dow PEI-6, Dow PEI-600e, Dow PEI-18, PEI-600, Ethylene imine polymer, Polyethylenimine, linear, Poly(ethyleneimine) solution, Ethylene imine polymer(PEI), Aziridin [German], EI, PEI, Polyethylenimine, linear(PEI)

Molecular formula
C2H5N
Empirical formula
C2H5N
Molecular weight
43.07 g/mol
Exact mass
43.04220
CAS number
151-56-4
PubChem CID
9033
Canonical SMILES
C1CN1
Isomeric SMILES
C1CN1
InChI
InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2
InChIKey
NOWKCMXCCJGMRR-UHFFFAOYSA-N
Molfile

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

Physical properties

TemperaturePressureDensity
Appearance
Oily, water-white liquid[5]
6 values

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

ValueAs writtenSource
–Ethyleneimine, stabilized appears as a clear colorless liquid with an ammonia-like odor. Flash point 12 °F. Less dense than water. Flammable over a wide range of vapor-air concentrations. Vapors irritate the skin, eyes, nose, and throat. May be toxic by prolonged inhalation, skin absorption, or ingestion. Carcinogenic. Vapors heavier than air. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently.[1] CAMEO Chemicals
–COLOURLESS LIQUID WITH PUNGENT ODOUR.[2] ILO-WHO International Chemical Safety Cards (ICSCs)
–Colorless liquid with an ammonia-like odor.[3] Occupational Safety and Health Administration (OSHA)
–Colorless liquid with an ammonia-like odor. [Note: Usually contains inhibitors to prevent polymerization.][4] The National Institute for Occupational Safety and Health (NIOSH)
–shownOily, water-white liquid[5] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 10th ed. Volumes 1-3 New York, NY: John Wiley & Sons Inc., 1999., p. V2: 1678
–Colorless liquid ... [Note: Usually contains inhibitors to prevent polymerization].[5] 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. 2004-103 (2003).
Odor
Amine odor[5]
2 values

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

ValueAs writtenSource
–Pungent, ammonia-like odor[5] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 10th ed. Volumes 1-3 New York, NY: John Wiley & Sons Inc., 1999., p. V2: 1678
–shownAmine odor[5] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 468
Melting point
Freezing point: -71.5 °C[5]
6 values

4 of 6 sources agree on it (most common value).

ValueAs writtenSource
−72 °C-98 °F Freezing Point (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.
−71.5 °CshownFreezing point: -71.5 °C[5] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 10th ed. Volumes 1-3 New York, NY: John Wiley & Sons Inc., 1999., p. V2: 1678
−74 °C-74 °C[2] ILO-WHO International Chemical Safety Cards (ICSCs)
−72 °C-97 °F[3] Occupational Safety and Health Administration (OSHA)
−77.9 °C-77.9 °C[6] PAC Chemical Database, U.S. Department of Energy
−72 °C-97 °F[4] The National Institute for Occupational Safety and Health (NIOSH)
Boiling point
55 to 56 °C (131 to 133 °F) at 760 mmHg (EPA, 1998)[1]
6 values

6 of 6 sources agree on it (most common value).

ValueAs writtenSource
55 to 56 °Cshown131 to 133 °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.
55 to 56 °C55-56 °C at 760 mm Hg[5] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 10th ed. Volumes 1-3 New York, NY: John Wiley & Sons Inc., 1999., p. V2: 1678
56 to 57 °C56-57 °C[2] ILO-WHO International Chemical Safety Cards (ICSCs)
56 °C133 °F[3] Occupational Safety and Health Administration (OSHA)
56 °C56 °C @760 [mm Hg][6] PAC Chemical Database, U.S. Department of Energy
56 °C133 °F[4] The National Institute for Occupational Safety and Health (NIOSH)
Density
0.8321 at 20 °C (68 °F) (EPA, 1998) - Less dense than water[1]
5 values

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

ValueAs writtenSource
–shown0.8321 at 68 °F (EPA, 1998) - Less dense than water[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): 0.8[2] ILO-WHO International Chemical Safety Cards (ICSCs)
–0.83[3] Occupational Safety and Health Administration (OSHA)
–0.832 @25 °C[6] PAC Chemical Database, U.S. Department of Energy
–0.83[4] The National Institute for Occupational Safety and Health (NIOSH)
Solubility in water
Solubility in water: miscible[2]
5 values

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

ValueAs writtenSource
–Miscible (NIOSH, 2024)[1] CAMEO Chemicals
–Soluble in ethanol; slightly soluble in ether; very soluble in chloroform; miscible in organic solvents[5] Hazardous Substances Data Bank (HSDB)cites Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V1: 335
–In water, 1X10+6 mg/L (miscible)[5] Hazardous Substances Data Bank (HSDB)cites Riddick, J.A., W.B. Bunger, Sakano T.K. Techniques of Chemistry 4th ed., Volume II. Organic Solvents. New York, NY: John Wiley and Sons., 1985., p. 622
–shownSolubility in water: miscible[2] ILO-WHO International Chemical Safety Cards (ICSCs)
–Miscible[4] The National Institute for Occupational Safety and Health (NIOSH)
log P
-0.36[2]
pKa
pKa= 8.04 (conjugate acid)[5]
Vapor pressure
160 mmHg at 20 °C (68 °F, EPA 1998)[1]
4 values

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

ValueAs writtenSource
160 mmHgshown160 mmHg 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.
213 mmHg213 mm Hg at 25 °C[5] Hazardous Substances Data Bank (HSDB)cites Chao J et al; J Phys Chem Ref Data 12: 1033-63 (1983)
160 mmHgVapor pressure, kPa at 20 °C: 21.3[2] ILO-WHO International Chemical Safety Cards (ICSCs)
75 mmHg75 [mm Hg] @4.0999999999999996 °C[6] 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
-11 °C c.c.[2]
5 values

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

ValueAs writtenSource
−11 °C12 °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.
−11 °C12 °F (-11 °C) (Closed cup)[5] Hazardous Substances Data Bank (HSDB)cites Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 325-62
−11 °Cshown-11 °C c.c.[2] ILO-WHO International Chemical Safety Cards (ICSCs)
−11 °C12 °F[3] Occupational Safety and Health Administration (OSHA)
−11 °C12 °F[4] The National Institute for Occupational Safety and Health (NIOSH)
Autoignition temperature
320 °C (608 °F)[5]
3 values

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

ValueAs writtenSource
320 °C608 °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.
320 °Cshown608 °F (320 °C)[5] Hazardous Substances Data Bank (HSDB)cites Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 325-62
322 °C322 °C[2] ILO-WHO International Chemical Safety Cards (ICSCs)
Refractive index
Index of refraction = 1.412 at 25 C/D[5]

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
3
Rings
1
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
1
H-bond donors
1
H-bond acceptors
1
Rotatable bonds
0
TPSA (Ų)
21.9
Formal charge
0
XLogP3
-0.4 PubChem
Complexity
10 PubChem
Stereocenters
None
Double-bond geometry
None specified
Point group
Cs of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C55.78%
  • H11.70%
  • N32.52%

Isotope pattern

100%43.0422.6%44.045

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
-0.41 Crippen (Wildman and Crippen 1999)
log S (water solubility)
0.15 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
1.87 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 43.07
  • log P ≤ 5 (Crippen): -0.41
  • H-bond donors ≤ 5: 1
  • 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 [7].

  • Flammable
  • Corrosive
  • Acute toxicity
  • Health hazard
  • Environmental hazard
343
NFPA 704[5]
  • H225Highly Flammable liquid and vapor
  • H300Fatal if swallowed
  • H310Fatal in contact with skin
  • H314Causes severe skin burns and eye damage
  • H330Fatal if inhaled
  • H340May cause genetic defects
  • H350May cause cancer
  • H411Toxic to aquatic life with long lasting effects

Precautionary statements: P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P318, P320, P321, P330, P361+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501

View all classifications (2)
  • [7] Regulation (EC) No 1272/2008 of the European Parliament and of the Council · DangerH225, H300, H310, H314, H330, H340, H350, H411
  • [8] European Chemicals Agency (ECHA) · 927 reports · DangerH225, H300+H310+H330, H300, H310, H314, H318, H330, H340, H350, H411

Exposure limits

  • PEL-TWA (8-Hour Time Weighted Average): Ca[3]
  • PEL: [1910.1012] See Appendix B[4]
  • REL: Ca See Appendix A[4]
  • TLV: 0.05 ppm as TWA; 0.1 ppm as STEL; (skin); A3 (confirmed animal carcinogen with unknown relevance to humans).[2]
  • TLV-TWA (Time Weighted Average): 0.05 ppm [2008][3]
  • TLV-STEL (Short Term Exposure Limit): 0.1 ppm [2008][3]

First aid

  • Warning: Ethyleneimine exposure may result in delayed pulmonary edema within 24 to 48 hours. Also, acute effects such as nausea, eye irritation, etc., are often delayed for 30 minutes to 3 hours. Caution is advised. Signs and Symptoms of Ethyleneimine Exposure: Acute exposure to ethyleneimine may result in irritation and burning of the eyes, nose, throat, respiratory tract, and mucous membranes. Dermal sensitization may occur. Corneal damage, bone marrow depression, delayed coughing, and laryngeal and pulmonary edema may also occur. Gastrointestinal effects may include nausea and vomiting.[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…[9]
  • (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.[4]
  • Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.[2]

Storage

  • Fireproof. Separated from acids, oxidants and food and feedstuffs. Dry. Store only if stabilized.[2]
  • Store in a cool, dry, well-ventilated location. Store away from heat, oxidizing materials, & sunlight. Separate from oxidizing materials & peroxides.[5]
  • (aziridine) normally stored over solid caustic alkali, to minimize polymerization catalysed by presence of carbon dioxide.[5]

Incompatibilities

  • (aziridine) gives the explosive 1-chloroazidine on treatment with (chlorinating agents) eg sodium hypochlorite solution.[5]
  • Explosive silver derivatives may be formed in contact with silver or its alloys, including silver solder, which is therefore unsuitable in handling equipment.[5]
  • Polymerizes explosively in presence of acids [Note: Explosive silver derivatives may be formed with silver alloys (e.g., silver solder)].[5]
  • Mixing acetic acid and ethyleneimine in a closed container caused the temperature and pressure to increase. (It was observed when equimolar quantities of 2 chemicals were mixed in a closed container. In some cases the changes were solely vapor pressure effects due to heat of solution.)[5]

Safety data sheets on the supplier’s page: Mcule, Molport, Thermo Fisher Scientific.

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]ILO-WHO International Chemical Safety Cards (ICSCs) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  3. [3]Occupational Safety and Health Administration (OSHA) · Public domain (US DOL) · via PubChem · retrieved 2026-10-14
  4. [4]The National Institute for Occupational Safety and Health (NIOSH) · Public domain (US CDC) · via PubChem · retrieved 2026-10-14
  5. [5]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
  6. [6]PAC Chemical Database, U.S. Department of Energy · Public domain (US DOE) · via PubChem · retrieved 2026-10-14
  7. [7]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
  8. [8]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  9. [9]Emergency Response Guidebook (ERG) · Public domain (US DOT) · via PubChem · retrieved 2026-10-14
  10. [10]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
  11. [11]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  12. [12]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  13. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  14. ·Literature on PubChem

Data last updated 2026-10-14.