3,5-Dichlorobenzonitrile

Base Information

• Chemical Name: 3,5-Dichlorobenzonitrile
• CAS No.: 6575-00-4
• Molecular Formula: C7H3Cl2N
• Molecular Weight: 172.014
• Hs Code.: 29269090
• European Community (EC) Number: 229-495-3
• NSC Number: 109596
• UNII: EY25KS4R7X
• DSSTox Substance ID: DTXSID00215950
• Nikkaji Number: J149.835E
• Wikidata: Q72465521
• ChEMBL ID: CHEMBL51500
• Mol file: 6575-00-4.mol

Synonyms:3,5-dichlorobenzonitrile

Chemical Property of 3,5-Dichlorobenzonitrile

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.097mmHg at 25°C
• Melting Point: 64-67 oC
• Refractive Index: 1.584
• Boiling Point: 223.279 °C at 760 mmHg
• Flash Point: 85.849 °C
• PSA: 23.79000
• Density: 1.404 g/cm³
• LogP: 2.86508
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Methanol (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 170.9642545
• Heavy Atom Count: 10
• Complexity: 150

Purity/Quality:

98% ^*data from raw suppliers

3,5-Dichlorobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36/37/39-22-36-36/37-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=C(C=C1Cl)Cl)C#N
• Uses: 3,5-Dichlorobenzonitrile was used as internal standard during the programmed temperature vaporization-GC-MS determination of dichlobenil and 2,6-dichlorobenzamide in onions.

Technology Process of 3,5-Dichlorobenzonitrile

There total 6 articles about 3,5-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: 94.0%

methanesulfonic acid 3,5-dichloro-phenyl ester + dicyanozinc (557-21-1) → 3,5-dichlorobenzonitrile (6575-00-4)

Guidance literature:

With palladium diacetate; PS-triphenylphosphine; In tetrahydrofuran; at 140 - 155 ℃; for 0.0416667h; microwave irradiation;

DOI:10.1080/00397910601039044

Reference yield: 72.0%

1-bromo-3,5-dichlorobenzene (19752-55-7) → 3,5-dichlorobenzonitrile (6575-00-4)

Guidance literature:

1-bromo-3,5-dichlorobenzene; With isopropylmagnesium chloride; lithium chloride; In tetrahydrofuran; at -15 ℃; for 0.25h;

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: 71.7%

3,5-dichlorobenzyl alcohol (60211-57-6) → 3,5-dichlorobenzonitrile (6575-00-4) + 3,5-dichlorobenzamide (5980-23-4)

Guidance literature:

With ammonia; oxygen; In tert-Amyl alcohol; water; at 100 ℃; for 3h; under 3750.38 Torr; Overall yield = > 99 percent; Autoclave; High pressure;

DOI:10.1021/acscatal.0c00485

upstream raw materials:

3,5-Dichloroaniline

dicyanozinc

zinc(II) cyanide

(3,5-dichlorophenyl)boronic acid

Downstream raw materials:

3-(p-chlorophenyl)-5-<2-<(tert-butyldimethylsilyl)amino>-2-(3,5-dichlorophenyl)vinyl>isothiazole

3,5-dichlorobenzamide

3,5-dichlorothiobenzamide

5-(3,5-Dichloro-phenyl)-2H-tetrazole

Refernces

• 1、 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.
• 2、 Srivastava, Rajiv R.,Zych, Andrew J.,Jenkins, David M.,Wang, Hong-Jun,Chen, Zhen-Jia,Fairfax, David J.. "Application of polymer-supported triphenylphosphine and microwave irradiation to the palladium-catalyzed cyanation of aryl triflates". . p. 431 - 438. Retrieved 2007/10/03.