34662-31-2

Basic information

• Product Name: 5-Chloro-2-nitrobenzonitrile
• Synonyms: 2-Nitro-5-chlorobenzonitrile;3-Chloro-6-nitrobenzonitrile;5-CHLORO-2-NITROBENZONITRILE;LABOTEST-BB LT00159768;5-CHLORO-2-NITROBENZONITRILE 97%;Benzonitrile, 5-chloro-2-nitro-;5-Chloro-2-nitrobenzonitrile,97%
• CAS NO: 34662-31-2
• Molecular Formula: C₇H₃ClN₂O₂
• Molecular Weight: 182.56
• EINECS: 252-132-5
• Product Categories: Aromatic Nitriles;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;Building Blocks;C6 to C7;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 34662-31-2.mol

Chemical Properties

• Melting Point: 89-91 °C(lit.)
• Boiling Point: 120°C/20mmHg(lit.)
• Flash Point: 143.1°C
• Appearance: /
• Density: 1.6133 (rough estimate)
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.5557 (estimate)
• CAS DataBase Reference: 5-Chloro-2-nitrobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-nitrobenzonitrile(34662-31-2)
• EPA Substance Registry System: 5-Chloro-2-nitrobenzonitrile(34662-31-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 34662-31-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloro-2-nitrobenzonitrile is used as an intermediate in the synthesis of various pharmaceutical compounds. Its chemical structure allows it to be a key component in the preparation of a series of 2,4-diamino-6-[(aralkyl and alicyclic)thio-, sulfinyl-, and sulfonyl]quinazolines through condensation reactions. These synthesized compounds have potential applications in the development of new drugs and therapeutic agents.
Used in Chemical Research:
Due to its unique chemical properties, 5-Chloro-2-nitrobenzonitrile can be utilized in chemical research for the development of novel compounds and materials. Its reactivity and structural features make it a valuable starting material for various chemical reactions and synthesis processes, contributing to the advancement of chemical science and technology.

InChI:InChI=1/C7H3ClN2O2/c8-6-1-2-7(10(11)12)5(3-6)4-9/h1-3H

Upstream product

• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 109-77-3 malononitrile 
• 611-06-3 2,4-dichloronitrobenzene 
• 40763-96-0 2-nitro-5-chlorobenzamide 
• 93033-30-8 5-chloro-2-nitrobenzaldehyde oxime 

Downstream Products

• 38710-88-2 5-(Naphthalen-1-yloxy)-2-nitro-benzonitrile 
• 13514-94-8 2-nitro-5-piperidyl-benzenecarbonitrile 
• 96336-91-3 5-dimethylamino-2-nitrobenzonitrile 
• 630410-64-9 5-([2-(dimethylamino)ethyl]methylamino}-2-nitrobenzenecarbonitrile 
• 51123-37-6 3-cyano-4'-methoxy-4-nitrodiphenylsulphide 
• 74409-75-9 5-(1H-Benzoimidazol-2-ylsulfanyl)-2-nitro-benzonitrile 
• 17511-27-2 5-<(Benzyl)methylamino>-2-nitrobenzonitril 
• 5922-60-1 2-amino-5-chlorobenzonitrile 
• 74761-53-8 4-<(3-cyano-4-nitrophenyl)thio>benzoic acid 
• 74396-23-9 2-nitro-5-<(4-phenyl-2-thiazolyl)thio>benzonitrile 
• 38710-83-7 2-nitro-5-phenoxybenzonitrile 
• 38713-58-5 5-(4-Chloro-naphthalen-1-yloxy)-2-nitro-benzonitrile 
• 38710-82-6 2-nitro-5-(4-chlorophenoxy)benzonitrile 
• 38710-84-8 5-(3,5-Bis-trifluoromethyl-phenoxy)-2-nitro-benzonitrile 

Relevant articles and documents

Conversions of aryl carboxylic acids into aryl nitriles using multiple types of Cu-mediated decarboxylative cyanation under aerobic conditions

Here, we used malononitrile or AMBN as a cyanating agent to develop efficient and practical protocols for Cu-mediated decarboxylative cyanations, under aerobic conditions, of aryl carboxylic acids bearing nitro and methoxyl substituents at the ortho position as well as of heteroaromatic carboxylic acids. These protocols involved economical methods to synthesize value-added aryl nitriles from simple and inexpensive raw materials. Further diversification of the 2-nitrobenzonitrile product was performed to highlight the practicality of the protocols. This journal is

Ag/Cu-mediated decarboxylative cyanation of aryl carboxylic acids with K4Fe(CN)6 under aerobic conditions

A method for facile synthesis of aryl nitriles has been well established via Ag/Cu-mediated decarboxylative cyanation of benzoic acids with K4Fe(CN)6 under aerobic conditions. The approach of using readily accessible aryl carboxylic acids and green K4Fe(CN)6 as starting material provides a feasible alternative to previous cyanation protocols. Control experiments revealed the key role of Cu for the process and excluded the possibility of a radical mechanism for the transformation.

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.

NMR Studies and electrophilic properties of triphenylphosphine-trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes into nitriles

NMR Studies on the reaction of triphenylphosphine with various amounts of triflic anhydride at 0 °C is described. The reagent structure resulting from mixing 1.3 equiv of Ph3P with Tf2O (1.0 mmol) has been established as an equilibrium mixture consisting mainly of triphenyl(trifluoromethylsulfonyloxy)phosphonium trifluoromethanesulfinate and the corresponding bis(triphenyl)oxodiphosphonium trifluoromethanesulfinate dimer. The electrophilic properties of the system have been exploited in the development of a mild method for converting aldoximes into nitriles. The dehydration occurs at 0 °C under very mild conditions by initial activation of the oxime oxygen, followed by treatment with a base and subsequent elimination of triphenylphosphine oxide. The substrate scope and functional group tolerance of this useful method are explored.

3H-azepines and related systems. Part 5. Photo-induced ring expansions of o-azidobenzonitriles to 3-cyano- and 7-cyano-3H-azepin-2(1H)-ones

Unlike other aryl azides bearing electron-withdrawing ortho-substituents, o-azidobenzonitriles on photolysis in aqueous-tetrahydrofuran yield mixtures of the expected 3-cyano- and the unexpected 7-cyano-3H-azepin-2(1H)-ones. In one instance ring contraction to a 2-azabicyclo[3.2.0]hept-6-ene-3-one is noted. X-ray crystallographic data for 7-cyano- and 4-chloro-7-cyano-3H-azepin-2-one, and for the azabicycloheptenone, are presented.

Studies on the synthesis of 5-benzyl-1,3,4-benzotriazepines from 2-isothiocyanatodesoxybenzoine

The reaction of 2-isothiocyanatodesoxybenzoine prepared from 2-aminodesoxybenzoine and thiophosgene in good yield and 2-aminoethanol or methylhydrazine supplied a 4-hydroxy-1,2,3,4-tetrahydroquinazoline and an open chained thiosemicarbazide derivative, respectively. When heating, both compounds react under loss of water. The latter forms the 5-benzyl-3-methyl-2-thioxo-2,3-dihydro-1H-1,3,4-benzotriazepine which can be alkylated at the sulphur atom and transformed into the 2-oxo analog.

Process for producing aromatic nitrile

A process for producing aromatic nitrile, comprising reacting aromatic halide substituted by a nitro group in the ortho position relative to the halogen atom with 0.1 to 0.99 mol of cuprous cyanide and 0.1 to 2.0 mol of alkali cyanide, both being per mol of said aromatic halide, in a polar solvent, the amount of said aprotic solvent being 0.1 to 30 parts by weight per 100 parts by weight of said aromatic halide.