4172-91-2

Basic information

• Product Name: N-Methyl-N-phenylcarbodiimide
• Synonyms: Ph-N=C=N-CH3;N-Methyl-N'-phenylcarbodiimide;N-((methylimino)methylene)aniline;N'-methyl-N-phenylmethanediimine;methyl(phenyl)carbodiimide
• CAS NO: 4172-91-2
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132.165
• Mol File: 4172-91-2.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 209°Cat760mmHg
• Flash Point: 71.7°C
• Density: 0.93g/cm³
• CAS DataBase Reference: N-Methyl-N-phenylcarbodiimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-N-phenylcarbodiimide(4172-91-2)
• EPA Substance Registry System: N-Methyl-N-phenylcarbodiimide(4172-91-2)

Safety Data

• Hazardous Substances Data: 4172-91-2(Hazardous Substances Data)

Upstream product

• 54246-62-7 1,4-Dihydro-4-methyl-1-phenyl-5H-tetrazol-5-on 
• 62-53-3 aniline 
• 5378-52-9 phenyl-1H-tetrazole 
• 77-78-1 dimethyl sulfate 
• 1455-91-0 1-phenyl-4-methyl-1,4-dihydro-5H-tetrazol-5-thione 
• 20743-49-1 2-methyl-5-phenyl-2H-tetrazole 
• 14213-16-2 5-methyl-1-phenyl-1H-tetrazole 
• 2724-69-8 1-methyl-3-phenylthiourea 
• 593-75-9 methyl isocyanate 
• 15424-14-3 N-phenylbenzohydrazonoyl chloride 
• 123149-88-2 1-Methyl-2,4-diphenyl-1,2,3-triazolium-chlorid 
• 34551-29-6 4-methyl-5-phenylimino-Δ²-1,2,3,4-thiatriazoline 
• 1007-36-9 1-methyl-3-phenylurea 
• 20743-50-4 1-methyl-5-phenyltetrazole 

Downstream Products

• 1380583-37-8 C₁₁H₁₂N₂O 
• 73027-62-0 N-methyl-1-phenyl-1H-tetrazol-5-amine 
• 112777-81-8 1,3-Dimethyl-4-phenylimino-[1,3]diazetidin-2-one 
• 106929-75-3 3-methyl-2,4-bis(phenylimino)-1,3-thiazetidine 
• 112777-82-9 1-Methyl-3-phenyl-4-[(Z)-phenylimino]-[1,3]diazetidin-2-one 
• 112777-83-0 1-Methyl-3-(4-nitro-phenyl)-4-[(Z)-phenylimino]-[1,3]diazetidin-2-one 
• 1007-36-9 1-methyl-3-phenylurea 
• 78077-91-5 2-Isopropyl-4-methyl-3,5-diphenylimino-1,2,4-oxadiazolidin 
• 82561-32-8 O,S-dimethyl O-(trimethylsilyl) phosphorodithioate 
• 59541-67-2 N-cyano-N'-methyl-N''-phenyl-guanidine 
• 69909-87-1 N-(2,4-dimethyl-3-phenylimino-[1,2,4]thiadiazolidin-5-ylidene)-N'-phenyl-benzamidine 
• 1360895-69-7 (4-(4-methoxyphenyl)-1,6-dimethyl-1,3,5-triazin-2-ylidene)phenylamine 
• 1360895-56-2 (4-butylamino-1,6-dimethyl-1,3,5-triazin-2(1H)-ylidene)phenylamine 

Relevant articles and documents

Selective formation of formamidines, carbodiimides and formimidates from isocyanide complexes of Mn(i) mediated by Ag2O

The isocyanide ligands in complexes fac-[Mn(CNR)(bipy)(CO)3]+ are selectively transformed into formamidines, carbodiimides and formimidates upon nucleophilic addition of NH2Me or alkoxides and subsequent treatment with Ag

Nitrile imines and nitrile ylides: Rearrangements of benzonitrile N-methylimine and benzonitrile dimethylmethylide to azabutadienes, carbodiimides, and ketenimines. chemical activation in thermolysis of azirenes, tetrazoles, oxazolones, isoxazolones, and oxadiazolones

Flash vacuum thermolysis (FVT) of 1-methyl-5-phenyltetrazole (5b), 2-methyl-5-phenyltetrazole (1b), and 3-methyl-5-phenyl-1,3,4-oxadiazol-2(3H)-one (3b) affords the nitrile imine (2b), which rearranges in part to N-methyl-N′-phenylcarbodiimide (7b). Another part of 2b undergoes a 1,4-H shift to the diazabutadiene (13). 13 undergoes two chemically activated decompositions, to benzonitrile and CH2=NH and to styrene and N 2. FVT of 2,2-dimethyl-4-phenyl-oxazol-5(2H)-one (16) at 400 C yields 3-methyl-1-phenyl-2-azabutadiene (18) in high yield. In contrast, FVT of 3,3-dimethyl-2-phenyl-1-azirene (21) at 600 C or 4,4-dimethyl-3-phenyl- isoxazolone (20) at 600 C affords only a low yield of azabutadiene (18) due to chemically activated decomposition of 18 to styrene and acetonitrile. There are two reaction paths from azirene (21): one (path a) leading to nitrile ylide (17) and the major products styrene and acetonitrile and the other (path b) leading to the vinylnitrene (22) and ketenimine (23). The nitrile ylide PhC -=N+=C(CH3)2 (17) is implicated as the immediate precursor of azabutadiene (18). FVT of either 3-phenylisoxazol- 5(4H)one (25) or 2-phenylazirene (26) at 600 C affords N-phenylketenimine (28). The nitrile ylide PhC-=N+=CH2 (30) is postulated as a reversibly formed intermediate. N-Phenylketenimine (28) undergoes chemically activated free radical rearrangement to benzyl cyanide. The mechanistic interpretations are supported by calculations of the energies of key intermediates and transition states.

A versatile thiouronium-based solid-phase synthesis of 1,3,5-triazines

A thiouronium-based solidphase synthesis of a 1,3,5-triazine scaffold has been developed. The key feature of the synthesis is the use of a readily accessible solid-supported thiouronium salt as a primary precursor for the stepwise assembly of the 1,3,5-tri-azine substrate. The sulfur linker employed in the synthesis is stable under both acidic and basic conditions and is versatile enough to provide access to monocyclic, bicyclic, and spirocyclic compounds with the 1,3,5-triazine scaffold. By using this synthetic strategy, a representative set of 79 compounds containing the 1,3,5-triazine scaffold were prepared.