5-Chloro-2-nitrobenzonitrile

Base Information

• Chemical Name: 5-Chloro-2-nitrobenzonitrile
• CAS No.: 34662-31-2
• Molecular Formula: C7H3 Cl N2 O2
• Molecular Weight: 182.566
• Hs Code.: 2926909090
• European Community (EC) Number: 252-132-5
• NSC Number: 310024
• DSSTox Substance ID: DTXSID80188219
• Nikkaji Number: J126.373K
• Wikidata: Q72455742
• Mol file: 34662-31-2.mol

Synonyms:5-Chloro-2-nitrobenzonitrile;34662-31-2;Benzonitrile, 5-chloro-2-nitro-;3-Chloro-6-nitrobenzonitrile;EINECS 252-132-5;2-Nitro-5-chlorobenzonitrile;NSC310024;5-chloro-2nitrobenzonitrile;5-chloro-2-nitro-benzonitrile;SCHEMBL1028184;DTXSID80188219;1H-BENZIMIDAZOLE, 6-CHLORO-;5-Chloro-2-nitrobenzonitrile, 97%;MFCD00007286;AKOS015889511;NSC 310024;NSC-310024;AS-49761;BP-21211;C2817;CS-0101024;FT-0639208;N10373;J-019693

Chemical Property of 5-Chloro-2-nitrobenzonitrile

Chemical Property:

• Appearance/Colour: Yellow solid.
• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 89-94 ºC
• Refractive Index: 1.5557 (estimate)
• Boiling Point: 313°Cat760mmHg
• Flash Point: 143.1°C
• PSA: 69.61000
• Density: 1.47g/cm³
• LogP: 2.64308
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 181.9883050
• Heavy Atom Count: 12
• Complexity: 229

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Chloro-2-nitrobenzonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Cl)C#N)[N+](=O)[O-]
• Uses: 5-Chloro-2-nitrobenzonitrile has been used in the preparation of a series of 2,4-diamino-6-[(aralkyl and alicyclic)thio-, sulfinyl-, and sulfonyl]quinazolines by condensation reaction.

Technology Process of 5-Chloro-2-nitrobenzonitrile

There total 7 articles about 5-Chloro-2-nitrobenzonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

5-chloro-2-nitrobenzaldehyde oxime (93033-30-8) → 3-chloro-6-nitrobenzonitrile (34662-31-2)

Guidance literature:

With trifluoromethylsulfonic anhydride; triethylamine; triphenylphosphine; In dichloromethane; at 0 ℃; for 0.166667h;

DOI:10.1016/j.tetlet.2010.01.119

Reference yield: 68.0%

5-chloro-2-nitrobenzoic acid (2516-95-2) + potassium ferrocyanide → 3-chloro-6-nitrobenzonitrile (34662-31-2)

Guidance literature:

With copper(l) iodide; oxygen; In dimethyl sulfoxide; at 160 ℃; for 10h; under 760.051 Torr; Schlenk technique; Sealed tube;

DOI:10.1021/acs.joc.5b02873

Reference yield: 42.0%

5-chloro-2-nitrobenzoic acid (2516-95-2) + malononitrile (109-77-3) → 3-chloro-6-nitrobenzonitrile (34662-31-2)

Guidance literature:

With potassium phosphate; copper(l) iodide; oxygen; In N,N-dimethyl-formamide; at 160 ℃; for 20h; Schlenk technique; Green chemistry;

DOI:10.1039/d0ob01945c

upstream raw materials:

5-chloro-2-nitrobenzaldehyde oxime

2-nitro-5-chlorobenzamide

5-chloro-2-nitrobenzoic acid

2,4-dichloronitrobenzene

Downstream raw materials:

5-(6-Bromo-naphthalen-2-yloxy)-2-nitro-benzonitrile

5-(Naphthalen-1-yloxy)-2-nitro-benzonitrile

2-nitro-5-<(4-phenyl-2-thiazolyl)thio>benzonitrile

2-nitro-5-(2-pyrimidinylthio)benzonitrile

Refernces

• 1、 Fu, Zhengjiang,Jiang, Ligao,Li, Zhaojie,Jiang, Yongqing,Cai, Hu. "Ag/Cu-mediated decarboxylative cyanation of aryl carboxylic acids with K4Fe(CN)6 under aerobic conditions". supporting information. p. 917 - 924. Retrieved 2019/03/17.
• 2、 Moussa, Ziad,Ahmed, Saleh A.,ElDouhaibi, Ahmad S.,Al-Raqa, Shaya Y.. "NMR Studies and electrophilic properties of triphenylphosphine-trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes into nitriles". experimental part. p. 1826 - 1831. Retrieved 2010/09/07.