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 
• 3085-54-9 N-(4-methylphenyl)formamide 
• 64-17-5 ethanol 
• 106-49-0 p-toluidine 
• 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 
• 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 

Downstream Products

• 27429-31-8 N-(4-methylphenyl)-N'-(2-pyridyl)thiourea 
• 57585-32-7 N-p-tolyl-formimidic acid methyl ester 
• 16596-03-5 N,N'-di-p-tolylformamidine 
• 15296-47-6 N-p-tolyl-formimidic acid ethyl ester 
• 16001-28-8 N-4-methylphenyl isocyanodichloride 
• 16519-45-2 N,N'-di-p-tolylselenourea 
• 36613-26-0 carbamic acid, (4-methylphenyl)-, 1-methylethyl ester 
• 38308-69-9 p-Tolyl-(4,4,4-trifluoro-3-methoxy-2-trifluoromethyl-but-1-enylidene)-amine 
• 76669-11-9 1,1''-Dimethyl-5'(4-tolylimino)dispiro-2(1H),2''(1''H),4,4''-tetron 
• 56409-89-3 1,4-Diphenyl-3-[(E)-p-tolylimino]-azetidine-2,2-dicarboxylic acid dimethyl ester 
• 79482-91-0 2-(4-Methylphenyl)-1-(4-methylphenylamino)-2H-benzopyrrol-4,7-dion 
• 79482-92-1 2,6-Bis(4-methylphenyl)-1,7-bis(4-methylphenylamino)benzo<1,2-c:4,5-c'>dipyrrol-4,8(2H,6H)-dion 
• 79482-93-2 2,6-Bis(4-methylphenyl)-1,5-bis(4-methylphenylamino)benzo<1,2-c:4,5-c'>dipyrrol-4,8(2H,6H)-dion 
• 2272-45-9 benzal-p-toluidine 

Relevant articles and documents

Isocyanide 2.0

The isocyanide functionality due to its dichotomy between carbenoid and triple bond characters, with a nucleophilic and electrophilic terminal carbon, exhibits unusual reactivity in organic chemistry exemplified for example in the Ugi reaction. Unfortunately, the over proportional use of only a few isocyanides hampers novel discoveries about the fascinating reactivity of this functional group. The synthesis of a broad range of isocyanides with multiple functional groups is lengthy, inefficient, and exposes the chemist to hazardous fumes. Here we present an innovative isocyanide synthesis overcoming these problems by avoiding the aqueous workup which we exemplify by parallel synthesis from a 0.2 mmol scale performed in 96-well microtiter plates up to a 0.5 mol multigram scale. The advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example, the hitherto believed to be unstable 2-isocyanopyrimidine, 2-acylphenylisocyanides and even o-isocyanobenzaldehyde could be accessed on a preparative scale and their chemistry was explored. Our new isocyanide synthesis will enable easy access to uncharted isocyanide space and will result in many discoveries about the unusual reactivity of this functional group. This journal is

Visible-light-induced radical cascade cyclization of oxime esters and aryl isonitriles: Synthesis of cyclopenta[: B] quinoxalines

A visible-light-induced radical cascade cyclization of aryl isonitriles and cyclobutanone oxime esters for the synthesis of cyclopenta[b]quinoxalines has been accomplished for the first time. The key to the success of this process was the integration of the in situ-formed nitrile radical followed by the cascade radical isonitrile/nitrile insertion-cyclization. The easy introduction of substituents for both substrates and the high functional group tolerance of the reaction make it an efficient strategy to give various quinoxaline derivatives in moderate to good yields.

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.