529-19-1

Basic information

• Product Name: o-Tolunitrile
• Synonyms: O-CYANO TOLUENE;LABOTEST-BB LT01273178;2-CYANOTOLUENE;2-TOLUNITRILE;2-METHYLBENZENECARBONITRILE;2-METHYLBENZONITRILE;2-Methylbenzonitrile/o-Tolunitrile;o-toluenenitrile
• CAS NO: 529-19-1
• Molecular Formula: C₈H₇N
• Molecular Weight: 117.15
• EINECS: 208-451-7
• Product Categories: Aromatic Nitriles
• Mol File: 529-19-1.mol
• Article Data: 257

Chemical Properties

• Melting Point: -13 °C
• Boiling Point: 205 °C(lit.)
• Flash Point: 184 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.989 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.243mmHg at 25°C
• Refractive Index: n20/D 1.5279(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Explosive Limit: 1.1-6.7%(V)
• Water Solubility: <0.1 g/100 mL at 17℃
• Merck: 14,9537
• BRN: 1857417
• CAS DataBase Reference: o-Tolunitrile(CAS DataBase Reference)
• NIST Chemistry Reference: o-Tolunitrile(529-19-1)
• EPA Substance Registry System: o-Tolunitrile(529-19-1)

Safety Data

• Hazard Codes: Xi
• Statements: 38-52/53-36/37/38
• Safety Statements: 61-37-36-26-24/25
• RIDADR: 3276
• WGK Germany: 2
• RTECS: XV0600000
• TSCA: Yes
• Hazardous Substances Data: 529-19-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

o-Tolyl Cyanide, is a versatile intermediate, used in the synthesis of various pharmaceutical and biologically active compounds. It can be used in the preparation of highly efficient triarylene conjugated dyes for sensitized solar cells

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 2948, 1995 DOI: 10.1021/jo00114a060

General Description

Light blue clear liquid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Nitriles, such as o-Tolunitrile, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Fire Hazard

o-Tolunitrile is combustible.

Purification Methods

Fractionally distil the nitrile, wash it with conc HCl or 50% H2SO4 at 60o until the smell of isonitrile has gone (this also removes any amines), then wash it with saturated NaHCO3 and dilute NaCl solutions, then dry it with K2CO3 and redistil it. [Beilstein 9 IV 1703.]

InChI:InChI=1/C8H7N/c1-7-4-2-3-5-8(7)6-9/h2-5H,1H3

Upstream product

• 74-90-8 hydrogen cyanide 
• 2028-34-4 o-toluene-diazonium chloride 
• 95-47-6 o-xylene 
• 94-69-9 2'-methylformanilide 
• 10468-64-1 o-tolyl isocyanide 
• 22627-00-5 2-methyl-benzophenone-imine 
• 64380-54-7 2-(2-methylphenyl)-1,3-dioxolane 
• 460-19-5 ethanedinitrile 
• 108-88-3 toluene 
• 420-04-2 CYANAMID 
• 143814-18-0 (4-cyanatophenyl)phenylmethanone 
• 89-93-0 ortho-methylbenzylamine 
• 118-90-1 ortho-methylbenzoic acid 
• 148651-34-7 iodo(2-cyanophenyl)zinc 

Downstream Products

• 10517-64-3 1-(2-Cyanophenyl)-1-phenyl-1-ethanone 
• 16216-13-0 2-phenyl-1-o-tolylethanone 
• 103987-46-8 2-methyl-N-thiazol-2-yl-benzamidine 
• 57027-68-6 2-hydroxyethyl 2-methylbenzoate 
• 61387-12-0 2-o-tolyl-6,7-dihydro-5H-cyclopenta[e][1,3]oxazin-4-one 
• 115751-68-3 N-(5-tetrazolyl)-o-toluamidine hydrochloride 
• 132635-70-2 N-(5-Chloro-pyrimidin-2-yl)-2-methyl-benzamidine 
• 96520-01-3 2-[1-tert-Butylamino-1-o-tolyl-meth-(Z)-ylidene]-cyclohexanone 
• 134666-17-4 N-(5-Chloro-thiazolo[5,4-b]pyridin-2-yl)-2-methyl-benzamidine 
• 84900-99-2 5,7-Diphenyl-2-o-tolyl-[1,3,4]thiadiazolo[3,2-a]pyridin-4-ylium; chloride 
• 60695-59-2 2-cyclohexylmethyl-1-{2-[3-(2-methylbenzoyl)phenyl]propyl}piperidine 
• 103560-17-4 1,1,1,3,3,3-Hexamethyl-2-(2-methyl-benzyl)-disilazane 
• 13001-39-3 2-[2-[4-[2-(4-cyanophenyl)vinyl]phenyl]vinyl]benzonitrile 
• 172422-08-1 α-cyanophenyl-2 phenyl-1 ethanol 

Relevant articles and documents

Cyanide-Free Cyanation of sp2 and sp-Carbon Atoms by an Oxazole-Based Masked CN Source Using Flow Microreactors

This work reports a cyanide-free continuous-flow process for cyanation of sp2 and sp carbons to synthesize aryl, vinyl and acetylenic nitriles from (5-methyl-2-phenyloxazol-4-yl) boronic acid [OxBA] reagent as a sole source of carbon-bound mask

METHOD FOR PRODUCING AROMATIC NITRILE COMPOUND AND CATALYST FOR SYNTHESIS OF AROMATIC NITRILE COMPOUND

PROBLEM TO BE SOLVED: To efficiently produce an aromatic nitrile compound by oxidizing a methyl group directly bonded to an aromatic ring into a cyano group by ammoxidation. SOLUTION: The present invention relates to a method for producing an aromatic nitrile compound wherein a zeolite carrying at least one selected from the group consisting of an alkali metal and an alkaline earth metal is used to, in the presence of ammonia, oxidize an aromatic compound having a methyl group bound to a carbon atom of an aromatic ring with oxygen. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2021,JPOandINPIT

Method for catalyzing oxidation of amines to generate nitrile by using nonmetal mesoporous nitrogen-doped carbon material

The invention discloses a method for preparing nitrile by catalyzing amine oxidation with a non-metal mesoporous nitrogen-doped carbon material catalyst, which is applied to the field of synthesis, the material is prepared by using a nitrogen-containing organic ligand as a precursor and silica sol as a template agent, calcining in the atmosphere of inert gases such as N2 or Ar and then removing the template agent; oxygen or air is used as an oxygen source, the reaction is performed at 80-130 DEG C under the action of ammonia water in the presence of a solvent, the effect is good, and the product still keeps higher activity after being recycled for more than 8 times, and has a wide industrial application prospect. The invention provides a heterogeneous non-metal catalytic system for catalyzing amine oxidation to prepare nitrile for the first time, and compared with a reported metal catalyst, the heterogeneous non-metal catalytic system does not bring metal pollution to a product to influence the effect of cyano drugs.