3365-81-9

Basic information

• Product Name: N-Methyl-4-biphenylamine
• Synonyms: N-Methyl-4-biphenylamine;N-Methyl-[1,1'-biphenyl]-4-aMine
• CAS NO: 3365-81-9
• Molecular Formula: C₁₃H₁₃N
• Molecular Weight: 183.25
• Mol File: 3365-81-9.mol

Chemical Properties

• Boiling Point: 324°Cat760mmHg
• Flash Point: 159.1°C
• Appearance: /
• Density: 1.052g/cm³
• Vapor Pressure: 0.000253mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: N-Methyl-4-biphenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-4-biphenylamine(3365-81-9)
• EPA Substance Registry System: N-Methyl-4-biphenylamine(3365-81-9)

Safety Data

• Hazardous Substances Data: 3365-81-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H13N/c1-14-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-10,14H,1H3

Upstream product

• 618-40-6 1-Methyl-1-phenylhydrazine 
• 71-43-2 benzene 
• 7664-93-9 sulfuric acid 
• 871882-23-4 1,3-bis-biphenyl-4-yl-3-methyl-triazene 
• 151-10-0 1,3-Dimethoxybenzene 
• 87-85-4 Hexamethylbenzene 
• 621-23-8 1,2,3-trimethoxybenzene 

Downstream Products

• 65021-03-6 Biphenyl-4-yl-methyl-[3-(10-phenyl-anthracen-9-yl)-propyl]-amine 
• 144432-80-4 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1152961-33-5 N-(cyclohexylmethyl)-[1,1′-biphenyl]-4-amine 
• 1233940-38-9 5-(phenyl)-1-methylindoline-2,3-dione 
• 2523-37-7 9-methylfluorene 

Relevant articles and documents

Reactions of N-methyl-N-(4-biphenylyl)nitrenium ion with electron-rich arenes: Laser flash photolysis and product studies

An arylnitrenium ion, N-methyl-N-(4-biphenylyl)nitrenium ion, was generated through photolysis of 1-(N-methyl-N-4-biphenylyl)amino-2,4,6-trimethylpyridinium tetrafluoroborate, and its reactions with various donor-substituted arenes (e.g., 1,3,5-trimethoxybenzene, mesitylene, 1,4-dimethoxybenzene, hexamethylbenzene, etc.) were examined using product analysis and laser flash photolysis. In general, trapping of the short-lived nitrenium ion by the arenes leads to three types of products: (1) the parent amine, N-methyl-N-4-biphenylylamine; (2) an ortho-adduct, where the ring position ortho to the nitrenium ion center is bonded to the arene ring; and (3) an N-adduct, where the nitrenium ion nitrogen is bonded to the trap. Laser flash photolysis studies show that the rates of these trapping reactions vary from 104 to 109 M-1 s-1, depending on the structure of the arene trap. These trapping rate constants do not correlate with the one-electron oxidation potential of the arene, nor with the expected stability of a σ-complex derived from direct electrophilic aromatic substitution. It is argued that the observed rate constants correspond to initial formation of a π-complex between the arylnitrenium ion and the arene trap. This complex then forms the observed products.

Fast reactions of arylnitrenium ions with amino acids and proteins: A laser flash photolysis study

Laser flash photolysis was used to examine the reaction of N-methyl-N-(4-biphenylyl)nitrenium ion with various amino acids and proteins in aqueous media. This nitrenium ion was found to react rapidly (> 10 8 M-1 s-1) with tryptophan, tyrosine, methionine and cysteine, more slowly (107-108M -1s-1) with lysine, histidine, and arginine. Rapid reaction was also seen with several representative proteins including bovine serum albumin, lysozyme, and chymotrypsin. These results suggest that reaction with proteins is likely to be a significant pathway in the reactions of nitrenium ions generated in vivo. Copyright

A TRIFLUOROMETHANESULFONIC ACID-CATALYZED REACTION OF ARYLHYDRAZINES WITH BENZENE

Arylhydrazines reacted with benzene in the presence of trifluoromethanesulfonic acid (TFSA) to give aminobiphenyls.This is a general method for the synthesis of aminobiphenyls.