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 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 94-69-9 2'-methylformanilide 
• 4943-59-3 N-o-tolyl-formimidic acid ethyl ester 
• 92114-96-0 mercury fulminate 
• 108-88-3 toluene 
• 95-53-4 o-toluidine 
• 614-69-7 2-tolyl isothiocyanate 
• 60-29-7 diethyl ether 
• 460-19-5 ethanedinitrile 
• 6921-34-2 benzylmagnesium chloride 
• 38362-89-9 1-methyl-2-(2-nitroethyl)benzene 

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 
• 87-24-1 ethyl 2-methylbenzoate 
• 91817-68-4 N-[(2-methylphenyl)methyl]acetamide 
• 153657-11-5 2-diacetoxymethyl-benzonitrile 
• 68723-25-1 (2-methylphenyl)-1-naphthylmethanone 
• 71682-90-1 β-amino-2-methyl-cinnamonitrile 
• 16216-13-0 2-phenyl-1-o-tolylethanone 
• 103987-46-8 2-methyl-N-thiazol-2-yl-benzamidine 
• 108897-24-1 4,4,6-trimethyl-2-o-tolyl-5,6-dihydro-4H-[1,3]oxazine 
• 20334-84-3 (1-o-Toluoylamino-cyclohexyl)-essigsaeure 
• 69143-35-7 Aethyl-2-imino-1-methyl-2-(o-tolyl)aethylsulfon 

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@CeO2-catalyzed cyanation of aryl iodides with K4Fe(CN)6·3H2O under visible light irradiation

Cyanation of aryl iodides is still challenging work for chemical researchers because of harsh reaction conditions and toxic cyanide sources. Herein, we have developed a new protocol based on the combination of the catalyst Pd@CeO2, nontoxic cyanide source K4[Fe (CN)6]·3H2O, and driving force visible light irradiation. The reaction is operated at relatively moderate temperature (55°C) and exhibits good catalytic efficiency of product aryl nitriles (yields of 89.4%). Moreover, the catalyst Pd@CeO2 possesses good reusability with a slight loss of photocatalytic activity after five consecutive runs. The reaction system based on the above combination shows a wide range of functional group tolerance under the same conditions. Reaction conditions such as temperature, time, the component of catalyst, and solutions are optimized by studying cyanation of 1-iodo-4-nitrobenzene as model reaction. According to these results, the possible mechanism of Pd@CeO2-catalyzed cyanation of aryl iodides under visible light irradiation is proposed based on the influence of visible light on the catalyst and reactant compounds. In all, we provided an environmental and economic method for preparation of aryl nitriles from cyanation of aryl iodides based on the goal of green chemistry for sustainable development.

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.