5336-53-8

Basic information

• Product Name: N-nitrosodibenzylamine
• Synonyms: N,N-DIBENZYLNITROSAMINE;Dibenzylnitrosamine;Nitrosodibenzylamine;N-Nitroso-N-benzylbenzenemethanamine
• CAS NO: 5336-53-8
• Molecular Formula: C₁₄H₁₄N₂O
• Molecular Weight: 226.30
• Product Categories: Aromatics;Mutagenesis Research Chemicals;Nitric Oxide Reagents
• Mol File: 5336-53-8.mol
• Article Data: 41

Chemical Properties

• Melting Point: 56-58°C
• Boiling Point: 367.89°C (rough estimate)
• Flash Point: 208.4°C
• Appearance: /
• Density: 1.0852 (rough estimate)
• Vapor Pressure: 6.64E-07mmHg at 25°C
• Refractive Index: 1.6419 (estimate)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• PKA: -5.91±0.70(Predicted)
• CAS DataBase Reference: N-nitrosodibenzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-nitrosodibenzylamine(5336-53-8)
• EPA Substance Registry System: N-nitrosodibenzylamine(5336-53-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 5336-53-8(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C14H14N2O/c17-15-16(11-13-7-3-1-4-8-13)12-14-9-5-2-6-10-14/h1-10H,11-12H2

Upstream product

• 64-17-5 ethanol 
• 20735-22-2 dibenzyl-amine; nitrite 
• 17761-41-0 N-chloro-N-(phenylmethyl)-benzenemethanamine 
• 35517-91-0 N,N-Dibenzylthiocarbamoylchlorid 
• 620-40-6 tribenzylamine 
• 64-19-7 acetic acid 
• 102-05-6 N-methyldibenzylamine 
• 509-14-8 tetranitromethane 
• 22014-90-0 N-Butyldibenzylamine 
• 858428-24-7 N,N-dibenzylbutan-2-amine 
• 6852-46-6 tribenzylamine-N-oxide 
• 46120-25-6 N-sec-butyl-N-benzylamine 
• 103-49-1 dibenzylamine 
• 25370-09-6 dibenzylcarbamyl chloride 

Downstream Products

• 3488-55-9 N-hydroxy-N'-(phenylmethyl)-benzenecarboximidamide 
• 39886-68-5 C₂₄H₂₅N₃O₄ 
• 100-52-7 benzaldehyde 
• 103-49-1 dibenzylamine 
• 20002-23-7 N-nitroso<α,α,α'α'-2H4>dibenzylamine 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 21136-32-3 1,1-dibenzyl-2-benzylidenehydrazine 
• 5802-60-8 N,N-dibenzylhydrazine 

Relevant articles and documents

KINETIC STUDY ON THE NITROSATION OF DIBENZYLAMINE IN A MODEL SYSTEM

A kinetic study of the formation of N-nitrosodibenzylamine (NDBzA), from the nitrosation of dibenzylamine (DBzA) by sodium nitrite, was performed in a model system under conditions (temperature, pH) that are similar to those encountered in the industrial production of hams processed in elastic rubber nettings. The nitrosation reaction was carried out in a KH2PO4 buffer (0.5 M) at pH 5.8 and at a temperature of 69 deg C. Since DBzA is insoluble in an aqueous buffer system, a non-ionic surfactant, Tween 20, was used as a solubilizing agent. The nitrosation reaction exhibited first-order kinetics with respect to DBzA and second-order kinetics with respect to nitrite. The calculated rate constant was 4.7 +/- 0.5 M-2/min. The pH profile of NDBzA formation eas also determined. The optimal pH of NDBzA formation, 3.12, was close to the pKa of nitrous acid (HNO2, pKa = 3.1).

Oxone-sodium nitrite mediated N-nitrosamines formation under mild conditions from secondary amines

Herein, we report an efficient synthesis of N-nitrosamines from cyclic, aliphatic, benzylic, and aromatic secondary amines via a novel straightforward, efficient, and mild chemical process using sodium nitrite and Oxone in methanol as a solvent at 0–5 °C. The demonstrated methodology accounts well for the parameters like cost-effective, short reaction time, clean and safe handling along with good to excellent yields.

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide

A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.