| Identification | Back Directory | [Name]
N-nitrosodibenzylamine | [CAS]
5336-53-8 | [Synonyms]
Dibenzylnitrosamine
Nitrosodibenzylamine
N,N-DIBENZYLNITROSAMINE
N-Nitroso-N-benzylbenzenemethanamine
Benzenemethanamine, N-nitroso-N-(phenylmethyl)-
N-nitrosodibenzylamine Solution in Methanol, 100μg/mL | [Molecular Formula]
C14H14N2O | [MDL Number]
MFCD00019921 | [MOL File]
5336-53-8.mol | [Molecular Weight]
226.27 |
| Chemical Properties | Back Directory | [Melting point ]
56-58°C | [Boiling point ]
367.89°C (rough estimate) | [density ]
1.0852 (rough estimate) | [refractive index ]
1.6419 (estimate) | [storage temp. ]
-20°C Freezer, Under Inert Atmosphere | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Low-Melting Solid to Solid | [pka]
-5.91±0.70(Predicted) | [color ]
Pale Yellow to Yellow | [InChI]
InChI=1S/C14H14N2O/c17-15-16(11-13-7-3-1-4-8-13)12-14-9-5-2-6-10-14/h1-10H,11-12H2 | [InChIKey]
RZJLAUZAMYYGMS-UHFFFAOYSA-N | [SMILES]
C1(CN(N=O)CC2=CC=CC=C2)=CC=CC=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Low Melting Solid | [Uses]
N-Nitrosodibenzylamine (NDBzA) is mutagenic to Salmonella typhimurium and induces DNA strand breaks in isolated rat hepatocytes. | [Production Methods]
Human exposure to NDBzA was not suspected,
but then there were reports of the compound in
hams wrapped in rubber netting. Concentrations
of NDBzA from 10 to 100 ppb were common, and some were
as high as 512 ppb. Like other nitrosamines in rubber,
NDBzA arose by nitrosation of dialkylamino compounds (in
this case dibenzyl-) during manufacture. | [Synthesis Reference(s)]
Tetrahedron Letters, 25, p. 2619, 1984 DOI: 10.1016/S0040-4039(01)81245-4 | [Safety Profile]
Moderately toxic by ingestion.Mutation data reported. When heated to decomposition itemits toxic vapors of NOx | [Carcinogenicity]
There is a single report of a test of nitrosodibenzylamine for
carcinogenicity in rats using high doses and that is
completely negative; in contrast, nitrosobenzylphenylamine
is a weak, but definite, esophageal carcinogen in
rats. NDBzA is not mutagenic to bacteria in the
presence or absence of rat liver microsomes.
Although there is no information about metabolism and
activation of NDBzA, the alpha-acetoxy derivative (which
presumably is the ester of the alpha-hydroxy derivative that
would be formed in vivo) is both carcinogenic to rats and
mutagenic to bacteria. |
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