Azacyclotridecan-2-one

Azacyclotridecan-2-one Basic information
Product Name:Azacyclotridecan-2-one
Synonyms:12-amino-dodecanoicacilactam;1-Aza-2-cyclotridecanone;2-Oxo-dodecamethylenimine;Aza-cyclotridecan-2-on;Azacyclotridecan-2-one;Cyclododecalactam;Dodecalactam;Dodecanoic acid, 12-amino-, lactam
CAS:947-04-6
MF:C12H23NO
MW:197.32
EINECS:213-424-8
Product Categories:Organics;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Lactams;Organic Building Blocks
Mol File:947-04-6.mol
Azacyclotridecan-2-one Structure
Azacyclotridecan-2-one Chemical Properties
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)
Fp 195 °C
form powder to crystal
pka16.91±0.20(Predicted)
color White to Almost white
Water Solubility 223mg/L at 20℃
BRN 122031
LogP2.71 at 20℃
EPA Substance Registry SystemAzacyclotridecan-2-one (947-04-6)
Safety Information
RIDADR 3257
WGK Germany 1
RTECS CL6940000
HS Code 2928.00.5000
HazardClass IRRITANT
Hazardous Substances Data947-04-6(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
Azacyclotridecan-2-one Usage And Synthesis
Chemical PropertiesDry PowderSolid; very faintly beige crystalline lumps. Virtually insol in water.
PreparationOne 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.

DefinitionChEBI: Laurolactam is an azamacrocycle and a keratan 6'-sulfate.
Health HazardThe 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 MethodsAzacyclotridecan-2-one crystallises from CHCl3 and is stored over P2O5 in a vacuum desiccator. [Beilstein 26/1 V 566.]
Azacyclotridecan-2-one Preparation Products And Raw materials
Raw materialsDodecanoic acid, 12-amino-, methyl ester
Preparation Products12-AMINODODECANOIC ACID
N-Propylpropionamide Pentanamide 1-AMINONONANE Ivarimods N-METHYLOCTYLAMINE N-METHYL N-NONYLAMINE N-Ethyl-1-heptanamine N-HEPTYLMETHYLAMINE N-TERT-BUTYLACETAMIDE N-UNDECYLAMINE N-METHYL-N-DECYLAMINE N-AMYL-N-BUTYLAMINE NONANAMIDE N-OCTANAMIDE Diamylamine Dibutylamine Dodecanamide N-BUTYLACETAMIDE

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