2-Chloro-6-methylbenzonitrile

Base Information

• Chemical Name: 2-Chloro-6-methylbenzonitrile
• CAS No.: 6575-09-3
• Molecular Formula: C8H6ClN
• Molecular Weight: 151.595
• Hs Code.: 29269095
• European Community (EC) Number: 229-499-5
• NSC Number: 80657
• UNII: 41M65JIW54
• DSSTox Substance ID: DTXSID3022241
• Nikkaji Number: J126.367F
• Wikidata: Q27258450
• Mol file: 6575-09-3.mol

Synonyms:2-CHLORO-6-METHYLBENZONITRILE;6575-09-3;Benzonitrile, 2-chloro-6-methyl-;2-Cyano-3-chlorotoluene;3-Chloro-2-toluonitrile;o-Tolunitrile, 6-chloro-;EINECS 229-499-5;41M65JIW54;MFCD00001782;NSC-80657;AI3-34983;6-Chloro-o-tolunitrile;NSC80657;2-cyano3-chlorotoluene;2-chloro-6-methylbezonitrile;SCHEMBL103444;UNII-41M65JIW54;2-chloro-6-methyl-benzonitrile;DTXSID3022241;BBL103511;CL9116;GEO-00710;NSC 80657;STL557321;2-Chloro-6-methylbenzonitrile, 97%;AKOS005258121;AM808195;LS-184955;FT-0608749;A851939;Q27258450

Chemical Property of 2-Chloro-6-methylbenzonitrile

Chemical Property:

• Appearance/Colour: light cream to light brown fine crystalline powder
• Vapor Pressure: 0.0367mmHg at 25°C
• Melting Point: 79-81 °C
• Refractive Index: 1.553
• Boiling Point: 241.1 °C at 760 mmHg
• Flash Point: 110.1 °C
• PSA: 23.79000
• Density: 1.19 g/cm³
• LogP: 2.52008
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 151.0188769
• Heavy Atom Count: 10
• Complexity: 158

Purity/Quality:

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

2-Chloro-6-methylbenzonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21
• Safety Statements: 23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)Cl)C#N
• Uses: FT-IR spectrum of 2-chloro-6-methylbenzonitrile has been studied in the region 400-4000cm-1 by KBr pellet technique.

Technology Process of 2-Chloro-6-methylbenzonitrile

There total 7 articles about 2-Chloro-6-methylbenzonitrile 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: 95.5%

1-chloro-2-iodo-3-methylbenzene (5100-98-1) + copper(l) cyanide → 2-chloro-6-methyl-benzonitrile (6575-09-3)

Guidance literature:

In N,N-dimethyl-formamide; at 20 - 100 ℃; for 16h; Inert atmosphere; Large scale;

Reference yield: 71.0%

2-Methylbenzonitrile (529-19-1) → 2-chloro-6-methyl-benzonitrile (6575-09-3)

Guidance literature:

With N-chloro-succinimide; palladium diacetate; toluene-4-sulfonic acid; In 1,2-dichloro-ethane; at 70 ℃; for 12h; Sealed tube;

DOI:10.1021/jo302765g

Reference yield:

2-chloro-6-methylaniline (87-63-8) → 2-chloro-6-methyl-benzonitrile (6575-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride; sodium nitrite / water / 0.33 h / -5 - 15 °C / Large scale

1.2: 1 h / 0 - 10 °C / Large scale

2.1: N,N-dimethyl-formamide / 16 h / 20 - 100 °C / Inert atmosphere; Large scale

With hydrogenchloride; sodium nitrite; In water; N,N-dimethyl-formamide; 1.1: |Sandmeyer Reaction / 1.2: |Sandmeyer Reaction;

upstream raw materials:

2-amino-6-methylbenzonitrile

potassium cyanide

2-chloro-6-methylaniline

2-cyano-3-nitrotoluene

Downstream raw materials:

2-Methyl-6-(2,2,2-trifluoro-ethoxy)-benzonitrile

2-chloro-6-(bromomethyl)benzonitrile

2-Methyl-6-butyloxy-benzonitril

6-chloro-2-methyl-3-nitrobenzonitrile

Refernces

• 1、 Du, Bingnan,Jiang, Xiaoqing,Sun, Peipei. "Palladium-catalyzed highly selective ortho-halogenation (I, Br, Cl) of arylnitriles via sp2 C-H bond activation using cyano as directing group". . p. 2786 - 2791. Retrieved 2013/04/24.