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

• 932-31-0 ortho-tolylmagnesium bromide 
• 506-77-4 cyanogen chloride 
• 615-37-2 ortho-methylphenyl iodide 
• 7677-24-9 trimethylsilyl cyanide 
• 151-50-8 potassium cyanide 
• 85515-91-9 (2-methylphenyl)phenylmethanone oxime 
• 1122-85-6 phenyl cyanate 
• 108-88-3 toluene 
• 91-15-6 phthalonitrile 
• 118-90-1 ortho-methylbenzoic acid 
• 614-69-7 2-tolyl isothiocyanate 
• 110-05-4 di-tert-butyl peroxide 
• 100-47-0 benzonitrile 
• 137-97-3 N,N'-di(o-tolyl)thiourea 

Downstream Products

• 10517-64-3 1-(2-Cyanophenyl)-1-phenyl-1-ethanone 
• 875856-17-0 1-(o-tolyl)pentan-1-imine 
• 54494-15-4 5-(2-methylphenyl)-3-phenyl-1,2,4-oxadiazole 
• 5585-14-8 3,4-diphenyl-furazan 2-oxide 
• 109866-09-3 4-isopropylidene-2,2-dimethyl-5-o-tolyl-3,4-dihydro-2H-pyrrole 
• 71682-90-1 β-amino-2-methyl-cinnamonitrile 
• 16216-13-0 2-phenyl-1-o-tolylethanone 
• 20334-84-3 (1-o-Toluoylamino-cyclohexyl)-essigsaeure 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 527-85-5 o-Methylbenzamid 
• 172422-08-1 α-cyanophenyl-2 phenyl-1 ethanol 
• 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 

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

Pd/CoFe2O4/chitosan: A highly effective and easily recoverable hybrid nanocatalyst for synthesis of benzonitriles and reduction of 2-nitroaniline

In this study, a novel catalyst system with high activity and easy recoverability was successfully prepared through the deposition of Pd nanoparticles (NPs) onto designed sustainable hybrid beads containing magnetic cobalt ferrite and chitosan (Pd/CoFe2O4/chitosan). The catalytic potential of Pd/CoFe2O4/chitosan hybrid nanocatalyst was then assessed in i) preparation of benzonitriles via aryl halides cyanation and ii) reduction of 2-nitroaniline (2-NA). Various aryl iodides and bromides were successfully cyanated by Pd/CoFe2O4/chitosan hybrid nanocatalyst with excellent reaction yields within 3 h. In addition to the production of benzonitriles, the hybrid nanocatalyst showed excellent activity by reducing 2-NA in 65 s. It was proved that the Pd/CoFe2O4/chitosan hybrid nanocatalyst outperformed many catalysts used in the cyanation of aryl halides and catalytic reduction of 2-NA previously reported in the literature. Moreover, it was found that the designed Pd/CoFe2O4/chitosan hybrid nanocatalyst was easily and effectively separated from the reaction mixture using an external magnet and reused several times in catalytic reactions without considerable loss of catalytic activity.

Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters

The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.