7175-47-5

Basic information

• Product Name: 4-TOLYLISOCYANIDE
• Synonyms: 4-TOLYLISOCYANIDE;Benzene, 1-isocyano-4-methyl- (9CI);1-Isocyano-4-methylbenzene;p-Methylphenyl isocyanide;p-Tolyl isocyanide
• CAS NO: 7175-47-5
• Molecular Formula: C₈H₇N
• Molecular Weight: 117.14788
• Product Categories: ISONITRITE
• Mol File: 7175-47-5.mol
• Article Data: 28

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-TOLYLISOCYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TOLYLISOCYANIDE(7175-47-5)
• EPA Substance Registry System: 4-TOLYLISOCYANIDE(7175-47-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 7175-47-5(Hazardous Substances Data)

Usage

Preparation

To a flask containing 5.4 gm (0.05 mole) of p-toluidine in 100 ml of dry 1,2-dimethoxyethane is added 28 gm (0.15 mole) of sodium trichloroacetate. The reaction is slightly exothermic. The reaction mixture is refluxed for ? hr, whereupon carbon dioxide is copiously evolved. The reaction mixture is filtered, the solid (10 gm) is washed with ether, and the combined reddish black filtrate concentrated. The residue is extracted with ether, washed with water, dried, and concentrated to afford a red-black oil, which, upon distillation, gives 2.5 gm (43%), b.p. 38°C (1 mm Hg), m.p. 19-20°C of a yellow liquid, IR, 4.69 μ (—NC).

InChI:InChI=1/C8H7N/c1-7-3-5-8(9-2)6-4-7/h3-6H,1H3

Upstream product

• 589-93-5 2,5-dimethylpyridine 
• 67-66-3 chloroform 
• 15296-47-6 N-p-tolyl-formimidic acid ethyl ester 
• 7647-01-0 hydrogenchloride 
• 16519-45-2 N,N'-di-p-tolylselenourea 
• 86119-84-8 phosphoric acid 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 81-88-9 rhodamine B 
• 113779-60-5 bis(4-methylphenylisocyanide)(tetra(2,3-pyrido)porphyrazinato)iron(II) 
• 113779-64-9 bis(4-methylphenylisocyanide)(phthalocyaninato)iron(II) 
• 622-52-6 p-methylphenylthiourea 
• 3717-15-5 p-methylbenzaldehyde oxime 
• 106-49-0 p-toluidine 

Downstream Products

• 27429-31-8 N-(4-methylphenyl)-N'-(2-pyridyl)thiourea 
• 42793-96-4 dihydroxy-malonic acid di-p-toluidide 
• 16519-45-2 N,N'-di-p-tolylselenourea 
• 106-49-0 p-toluidine 
• 89-62-3 4-methyl-2-nitroaniline 
• 85830-78-0 1,4-Bis(4-methylphenylimino)-3,6-diphenyl-1H,4H-furo<3,4-c>furan 
• 90827-52-4 2-(4-Methylphenyl)-1-(4-methylphenylamino)-2H-benzoisoindol-4,9-dion 
• 56106-02-6 1-(4-methylphenyl)-3-(4-methoxyphenyl)urea 
• 134455-17-7 1-Methyleneamino-cyclohexanecarboxylic acid p-tolylamide 
• 134420-39-6 3-p-Tolyl-1,3-diaza-spiro[4.5]dec-1-en-4-one 
• 134420-33-0 2-Thioxo-4-[(Z)-p-tolylimino]-1,3-diaza-spiro[4.5]decane-1-carbothioic acid S-(4-chloro-phenyl) ester 
• 134420-34-1 2-Thioxo-4-[(Z)-p-tolylimino]-1,3-diaza-spiro[4.5]decane-1-carbothioic acid S-(2-nitro-phenyl) ester 
• 129801-46-3 7-Methyl-1-({5-oxo-1-p-tolyl-4-[1-p-tolyl-meth-(E)-ylidene]-4,5-dihydro-1H-imidazol-2-yl}-p-tolyl-amino)-isoquinoline-3-carboxylic acid ethyl ester 
• 129801-47-4 5-Methoxy-1-({4-[1-(2-methoxy-phenyl)-meth-(E)-ylidene]-5-oxo-1-p-tolyl-4,5-dihydro-1H-imidazol-2-yl}-p-tolyl-amino)-isoquinoline-3-carboxylic acid ethyl ester 

Relevant articles and documents

Silver-Catalyzed Selective Multicomponent Coupling Reactions of Arynes with Nitriles and Isonitriles

Pathway selective aryne-based novel multicomponent coupling reactions with isonitriles and nitriles are described. Crucial to these reactions is the formation of a silver-aryne complex, which shows differential reactivity toward isonitriles and nitriles to form two different forms of ortho-nitrilium organosilver arene species. Interception of the nitrilium of an aryne-isonitrile adduct with another isonitrile leads to the formation of benzocyclobutene-1,2-diimines, whereas the nitrilium of an aryne-nitrile adduct renders selective formation of 3H-indol-3-imines or 3-iminoindolin-2-ol depending on the structure of the nitrile employed.

Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines

Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)2 or Pd(PPh3)4 to afford imines and/or α-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas α-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/α-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or α-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.

Selective Gold-Catalysed Synthesis of Cyanamides and 1-Substituted 1H-Tetrazol-5-Amines from Isocyanides

The newly discovered gold-catalysed reaction of isocyanides with hydrazoic acid generated in situ from trimethylsilyl azide and methanol (or, alternatively, from NaN3/AcOH) produces either cyanamides or 1-substituted 1H-tetrazol-5-amines, depending on the amount of available HN3. The reaction proceeds selectively and in generally high yields of either product, thus providing a particularly convenient access to a wide range of substituted 1H-tetrazol-5-amines that are rather difficult to access otherwise.