Azacyclotridecan-2-one

Synonym(s):Aza-2-cyclotridecanone;Cyclododecanone isooxime;Laurolactam

CAS NO.：947-04-6
Empirical Formula: C12H23NO
Molecular Weight: 197.32
MDL number: MFCD00005104
EINECS: 213-424-8
SAFETY DATA SHEET (SDS)
Update Date: 2026-07-02 22:15:05

What is Azacyclotridecan-2-one?

Chemical properties

Dry PowderSolid; very faintly beige crystalline lumps. Virtually insol in water.

Preparation

One route to dodecyllactam is from butadiene as follows:

947-04-6 synthesis

Butadiene is trimerized with a Ziegler-Natta catalyst to give 1,5,9-cyclododecatriene which is then hydrogenated to cyclododecane. Dodecyllactam is then obtained by a series of reactions similar to those used to prepare caprolactam from cyclohexane.

Definition

ChEBI: Laurolactam is an azamacrocycle and a keratan 6'-sulfate.

Health Hazard

The acute oral LD50 was 2,330 mg/kg bw (rat) with central nervous system stimulation (trembling, convulsive twitches, ataxia) as the main clinical sign appearing at about 1,580 mg/kg bw. The dermal LD50 was greater than 2,000 mg/kg bw (rat). Decreased food consumption and stagnation of body weight development were noted. Validacute inhalation studies are not available. Azacyclotridecan-2-one was not irritating to the rabbit skin or eye (OECD TG 404, 405). It was not sensitizing in aguinea pig maximization test (OECD TG 406; 1981).

Purification Methods

Azacyclotridecan-2-one crystallises from CHCl3 and is stored over P2O5 in a vacuum desiccator. [Beilstein 26/1 V 566.]

Properties of Azacyclotridecan-2-one

Melting point:	150-153 °C(lit.)
Boiling point:	334.44°C (rough estimate)
Density	0.9415 (rough estimate)
vapor pressure	0.001Pa at 20℃
refractive index	1.4400 (estimate)
Flash point:	195 °C
pka	16.91±0.20(Predicted)
form	powder to crystal
color	White to Almost white
Water Solubility	223mg/L at 20℃
BRN	122031
EPA Substance Registry System	Azacyclotridecan-2-one (947-04-6)

Safety information for Azacyclotridecan-2-one

Signal word	Warning
Pictogram(s)	Health Hazard GHS08
GHS Hazard Statements	H371:Specific target organ toxicity, single exposure H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P260:Do not breathe dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P273:Avoid release to the environment. P405:Store locked up. P501:Dispose of contents/container to..…