4-Chloro-3-methylbenzonitrile

Base Information

• Chemical Name: 4-Chloro-3-methylbenzonitrile
• CAS No.: 4387-31-9
• Molecular Formula: C8H6ClN
• Molecular Weight: 151.595
• Hs Code.: 2926909090
• European Community (EC) Number: 610-155-1
• DSSTox Substance ID: DTXSID80397586
• Wikidata: Q72453725
• Mol file: 4387-31-9.mol

Synonyms:4-Chloro-3-methylbenzonitrile;4387-31-9;3-methyl-4-chlorobenzonitrile;4-chloro-3-methyl-benzonitrile;MFCD03452793;BENZONITRILE, 4-CHLORO-3-METHYL-;SCHEMBL410305;DTXSID80397586;SQISNVXBYZWWBC-UHFFFAOYSA-N;AKOS006279492;AC-1062;CS-W003088;DS-1023;FS-2530;SY016833;A7016;AM20050171;FT-0651218;J-515021

Chemical Property of 4-Chloro-3-methylbenzonitrile

Chemical Property:

• Vapor Pressure: 0.0321mmHg at 25°C
• Refractive Index: 1.553
• Boiling Point: 243.5 °C at 760 mmHg
• Flash Point: 99.9 °C
• PSA: 23.79000
• Density: 1.19 g/cm³
• LogP: 2.52008
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.2
• 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:

97% ^*data from raw suppliers

4-Chloro-3-methylbenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)C#N)Cl

Technology Process of 4-Chloro-3-methylbenzonitrile

There total 4 articles about 4-Chloro-3-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: 82.0%

1-chloro-4-iodo-2-methylbenzene (116632-41-8) + potassium ferrocyanide → 4-chloro-3-methylbenzonitrile (4387-31-9)

Guidance literature:

With CuO-supported Pd⁽⁰⁾ nanoparticles; In N,N-dimethyl-formamide; at 120 ℃; for 12h;

DOI:10.1016/j.tetlet.2009.01.027

Reference yield:

zinc(II) cyanide (557-21-1) + 2-methylchlorobenzene (95-49-8) → 3-chloro-4-methylbenzonitrile (21423-81-4) + 4-chloro-3-methylbenzonitrile (4387-31-9)

Guidance literature:

With 3-(trifluoromethyl)quinoline; palladium diacetate; silver fluoride; N-acetylglycine; at 80 ℃; for 18h; Overall yield = 53 %;

DOI:10.1021/acscatal.8b04639

Reference yield:

2-chloro-5-bromotoluene (54932-72-8) → 4-chloro-3-methylbenzonitrile (4387-31-9)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium / 1.) THF, hexane, -10 deg C, 3 h, 2.) THF, hexane, -70 deg C to -40 deg C, 2 h

2: pyridine; hydroxylamine hydrochloride / 1.) RT, 15 min, 2.) toluene, reflux, 4 h

With pyridine; n-butyllithium; hydroxylamine hydrochloride;

DOI:10.1021/jm9700225

upstream raw materials:

2-chloro-5-bromotoluene

1-chloro-4-iodo-2-methylbenzene

zinc(II) cyanide

2-methylchlorobenzene

Downstream raw materials:

2-(4-Chloro-3-methyl-phenyl)-1-(4-methanesulfonyl-phenyl)-4-trifluoromethyl-4,5-dihydro-1H-imidazol-4-ol

3-(bromomethyl)-4-chlorobenzonitrile

4-(1-Butyl-piperidin-4-yloxy)-3-methyl-benzonitrile

C₈H₉ClN₂O