3-Bromo-5-methylbenzonitrile

Base Information

• Chemical Name: 3-Bromo-5-methylbenzonitrile
• CAS No.: 124289-21-0
• Molecular Formula: C8H6 Br N
• Molecular Weight: 196.046
• Hs Code.: 2926909090
• European Community (EC) Number: 674-791-1
• DSSTox Substance ID: DTXSID20561724
• Nikkaji Number: J275.783D
• Wikidata: Q72446773
• Mol file: 124289-21-0.mol

Synonyms:3-Bromo-5-methylbenzonitrile;124289-21-0;Benzonitrile, 3-bromo-5-methyl-;3-bromo-5-cyanotoluene;MFCD08061970;3-Methyl-5-bromobenzonitrile;SCHEMBL254589;3-Bromo-5-methyl-benzonitrile;DTXSID20561724;JRGGBJGKQMUYOK-UHFFFAOYSA-N;CL9117;AKOS006283982;CS-W003460;GS-4390;AC-26117;SY021362;A21030;EN300-112948;J-512037

Chemical Property of 3-Bromo-5-methylbenzonitrile

Chemical Property:

• Vapor Pressure: 0.016mmHg at 25°C
• Melting Point: 57-58.5℃
• Refractive Index: 1.591
• Boiling Point: 256.144oC at 760 mmHg
• Flash Point: 108.712oC
• PSA: 23.79000
• Density: 1.517g/cm3
• LogP: 2.62918
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 194.96836
• Heavy Atom Count: 10
• Complexity: 158

Purity/Quality:

97% ^*data from raw suppliers

3-Bromo-5-methylbenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)Br)C#N
• Uses: 3-Bromo-5-methylbenzonitrile is used in the synthesis of arenes with high steric regiocontrol.

Technology Process of 3-Bromo-5-methylbenzonitrile

There total 17 articles about 3-Bromo-5-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: 75.0%

5-bromo-1,3-xylene (556-96-7) → 3-bromo-5-methylbenzonitrile (124289-21-0)

Guidance literature:

With tert.-butylnitrite; N-hydroxyphthalimide; palladium diacetate; In acetonitrile; at 70 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201305731

Reference yield: 74.0%

3,5-dibromotoluene (1611-92-3) + copper(l) cyanide → 3-bromo-5-methylbenzonitrile (124289-21-0)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; at 190 ℃; for 10h; Microwave irradiation;

Reference yield: 59.0%

zinc(II) cyanide (557-21-1) + 2-(3-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (942069-53-6) → 3-bromo-5-methylbenzonitrile (124289-21-0)

Guidance literature:

With copper(II) nitrate trihydrate; cesium fluoride; In methanol; water; at 100 ℃; for 6h;

DOI:10.1126/science.1248042

upstream raw materials:

3-bromo-5-methyl-benzoic acid

2-Amino-5-methylbenzoic acid

2-amino-3-bromo-5-methylbenzoic acid

3,5-dibromotoluene

Downstream raw materials:

α-Bromo-3-bromo-5-cyanotoluene

3-bromo-N-(2,6-diisopropylphenyl)-5-methylbenziimidamide

2-(3-bromo-5-methyl)-1-(2,6-diisopropylphenyl)-1H-imidazole

2,2'-(oxybis(3-methyl-5,1-phenylene))bis(1-(2,6-diisopropylphenyl)-1H-imidazole)