Propyleneimine

Propyleneimine (or propylene imine) is the organic compound with the formula CH₃CH(NH)CH₂. It is a secondary amine and the smallest chiral aziridine (ring containing C₂N). It is a flammable colorless liquid. Its derivatives, copolymers and oligomers, are of commercial interest.^[4]

Propyleneimine

Names
IUPAC name 2-Methylaziridine
Other names 1,2-Propylenimine
Identifiers
CAS Number	75-55-8 Y
3D model (JSmol)	Interactive image
ChemSpider	6137
ECHA InfoCard	100.000.799
EC Number	613-033-00-6
KEGG	C19496
PubChem CID	6377
RTECS number	CM8050000
UNII	ULC972Q7TZ Y
UN number	1921 (inhibited)
CompTox Dashboard (EPA)	DTXSID8024286
InChI InChI=1S/C3H7N/c1-3-2-4-3/h3-4H,2H2,1H3 Key: OZDGMOYKSFPLSE-UHFFFAOYSA-N InChI=1/C3H7N/c1-3-2-4-3/h3-4H,2H2,1H3 Key: OZDGMOYKSFPLSE-UHFFFAOYAW
SMILES N1C(C)C1
Properties
Chemical formula	C3H7N
Molar mass	57.096 g·mol−1
Appearance	Colorless, oily liquid[1]
Odor	ammonia-like[1]
Density	0.9 g/mL[2]
Melting point	−63 °C (−81 °F; 210 K)[2]
Boiling point	67 °C (153 °F; 340 K)[2]
Solubility in water	Miscible[2]
Vapor pressure	112 mmHg (20°C)[1]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H300, H310, H318, H330, H350, H411
Precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Flash point	−4 °C (25 °F; 269 K)[2]
Lethal dose or concentration (LD, LC):
LCLo (lowest published)	500 ppm (rat, 4 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 2 ppm (5 mg/m3) [skin][1]
REL (Recommended)	Ca TWA 2 ppm (5 mg/m3) [skin][1]
IDLH (Immediate danger)	Ca [100 ppm][1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Uses

This chemical is used in the paper, textile, rubber and pharmaceutical industries. Propyleneimine is also used in making paint.

The top global producers of this specialty chemical include DuPont, Mitsubishi Chemical Holdings Corporation, Sigma-Aldrich, Dixie Chemical Company, J and K Scientific, Apollo Scientific, Mitsui Chemicals.^[5]

The compound is also of interest for the synthesis of dendrimers, a process that exploits the tendency of aziridines to undergo ring-opening reactions.^{[6] [2]}

Health Effects

NIOSH considers propyleneimine a potential occupational carcinogen.

According to a report prepared for the United Church of Christ, propyleneimine emissions from the Dixie Chemical Company facility in Bayport, Pasadena, Texas, are one of the top ten toxicity-weighted air pollutions in the United States.^[7]