2,5-Dichlorobenzonitrile

Base Information

• Chemical Name: 2,5-Dichlorobenzonitrile
• CAS No.: 21663-61-6
• Molecular Formula: C7H3Cl2N
• Molecular Weight: 172.014
• Hs Code.: 29269090
• European Community (EC) Number: 244-518-7
• NSC Number: 166361
• DSSTox Substance ID: DTXSID70176049
• Nikkaji Number: J195.892E
• Wikidata: Q72465518
• Mol file: 21663-61-6.mol

Synonyms:2,5-Dichlorobenzonitrile;21663-61-6;Benzonitrile, 2,5-dichloro-;MFCD00019741;2,5-dichloro-benzonitrile;2,5-Dichlorobenzonitrile 98%;NSC166361;2,5-dichlorobenzonitrite;SCHEMBL104941;2,5-Dichlorobenzonitrile, 97%;DTXSID70176049;AMY36994;EINECS 244-518-7;BBL011046;CK2138;STK802217;AKOS005254736;CS-W017633;NSC 166361;NSC-166361;PS-4330;AC-23451;SY017110;AI3-33405;D4018;FT-0610307;A18454;EN300-172873;W-107533

Chemical Property of 2,5-Dichlorobenzonitrile

Chemical Property:

• Appearance/Colour: off-white crystal
• Vapor Pressure: 0.0254mmHg at 25°C
• Melting Point: 128-132 °C(lit.)
• Refractive Index: 1.583
• Boiling Point: 247.6 °C at 760 mmHg
• Flash Point: 103.9 °C
• PSA: 23.79000
• Density: 1.4 g/cm³
• LogP: 2.86508
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 170.9642545
• Heavy Atom Count: 10
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dichlorobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,T,Xn
• Hazard Codes: Xi,T,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Cl)C#N)Cl

Technology Process of 2,5-Dichlorobenzonitrile

There total 7 articles about 2,5-Dichlorobenzonitrile 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: 95.2%

1,4-Dichloro-2-chloromethyl-benzene (2745-49-5) → 2,5-dichlorobenzonitrile (21663-61-6)

Guidance literature:

With V₁Cr₂B_0.9Mn_0.2Li_0.2O_7.35; ammonia; at 364.84 ℃; for 8h;

Reference yield: 72.0%

2-bromo-1,4-dichlorobenzene (1435-50-3) → 2,5-dichlorobenzonitrile (21663-61-6)

Guidance literature:

2-bromo-1,4-dichlorobenzene; With magnesium; In tetrahydrofuran; at 20 ℃; for 2h;

With N,N-dimethyl-formamide; In tetrahydrofuran; at 0 ℃; for 2h;

With ammonia; iodine; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2012.12.022

Reference yield: 70.0%

1-5-η5-1,4-dichloro-exo-6-cyanocyclohexadienyl-η5-cyclopentadienyliron + 2,3-dicyano-5,6-dichloro-p-benzoquinone (84-58-2) → 2,5-dichlorobenzonitrile (21663-61-6)

Guidance literature:

In acetonitrile; stirring of a soln. of the compd. with DDQ in CH3CN (room temp., 30 min); filtration (sintered glass filter), evapn. to dryness, redissolving of the residue in CH2Cl2, chromy. (alumina column, CH2Cl2), removal of solvent;

DOI:10.1016/0022-328X(89)85345-8

upstream raw materials:

2,5 dichloroaniline

2,3-dicyano-5,6-dichloro-p-benzoquinone

2,5-dichlorotoluene

2-bromo-1,4-dichlorobenzene

Downstream raw materials:

2,5-dichloroacetophenone

[5-chloro-2-(1H-1,2,4-triazol-1-yl)phenyl]methanol

1-[2-(bromomethyl)-4-chlorophenyl]-1H-1,2,4-triazole

[5-chloro-2-(1H-1,2,4-triazol-1-yl)phenyl]acetonitrile

Refernces

• 1、 -. "Preparation of 2, 5 - dichlorobenzonitrile method and special catalyst and its preparation method". Paragraph 0030-0041. . Retrieved 2019/07/04.
• 2、 Ishii, Genki,Harigae, Ryo,Moriyama, Katsuhiko,Togo, Hideo. "Practical one-pot conversion of aryl bromides and β-bromostyrenes into aromatic nitriles and cinnamonitriles". . p. 1462 - 1469. Retrieved 2013/02/25.