3-Methyl-5-nitrobenzonitrile

Base Information

• Chemical Name: 3-Methyl-5-nitrobenzonitrile
• CAS No.: 124289-22-1
• Molecular Formula: C8H6N2O2
• Molecular Weight: 162.148
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID80561725
• Nikkaji Number: J275.784B
• Wikidata: Q72493487
• Mol file: 124289-22-1.mol

Synonyms:3-METHYL-5-NITROBENZONITRILE;124289-22-1;Benzonitrile, 3-methyl-5-nitro-;MFCD17170423;3-Cyano-5-nitrotoluene;SCHEMBL1344128;DTXSID80561725;AKOS015919702;CS-W003891;DS-1683;SY016059;A24150;EN300-245614;3-cyano-5-nitrotoluene;3-cyano-5-methylnitrobenzene;Z1255502451

Chemical Property of 3-Methyl-5-nitrobenzonitrile

Chemical Property:

• Melting Point: 104-105℃
• Boiling Point: 292.1±28.0℃ (760 Torr)
• Flash Point: 130.5±24.0℃
• PSA: 69.61000
• Density: 1.26±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 2.29808
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 225

Purity/Quality:

98%min ^*data from raw suppliers

3-Methyl-5-nitrobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)[N+](=O)[O-])C#N

Technology Process of 3-Methyl-5-nitrobenzonitrile

There total 6 articles about 3-Methyl-5-nitrobenzonitrile 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: 59.0%

1-bromo-3-methyl-5-nitrobenzene (52488-28-5) + copper(I) cyanide (544-92-3) → 5-methyl-3-nitrobenzonitrile (124289-22-1)

Guidance literature:

In N,N-dimethyl-formamide; for 6h; Heating;

DOI:10.7164/antibiotics.47.1456

Reference yield:

3-Methylbenzonitrile (620-22-4) → 3-methyl-4-nitrobenzonitrile (96784-54-2) + 2-nitro-5-methylbenzonitrile (64113-86-6) + 5-methyl-3-nitrobenzonitrile (124289-22-1)

Guidance literature:

With Nitrogen dioxide; ozone; In acetonitrile; at -10 ℃; for 3h; Further Variations:; Reagents; Temperatures; Product distribution;

DOI:10.1039/b301847d

Reference yield:

2-bromo-4-methyl-6-nitroaniline (827-24-7) → 5-methyl-3-nitrobenzonitrile (124289-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) conc. H₂SO₄, NaNO₂, 2.) 50percent H₃PO₂, Cu₂O / 1.) H₂O, -2 deg C - -3 deg C, 2 h, 2.) H₂O, -5 deg C, 90 min; 0 deg C, 10 min

2: 59 percent / dimethylformamide / 6 h / Heating

With copper(I) oxide; sulfuric acid; hypophosphorous acid; sodium nitrite; In N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.47.1456

upstream raw materials:

1-bromo-3-methyl-5-nitrobenzene

copper(I) cyanide

3-Methylbenzonitrile

2-bromo-4-methyl-6-nitroaniline

Downstream raw materials:

5-Methyl-3-nitrobenzoic acid

3-(benzhydrylidenylamino)-5-methylbenzonitrile

3-(benzhydrylidenylamino)-5-bromomethylbenzonitrile

{1-[3-(benzhydrylidenylamino)-5-cyanobenzyl]-2-oxopyrrolidin-3-yl}carbamic acid tert-butylester

Refernces

• 1、 Peng, Xinhua,Fukui, Naoyuki,Mizuta, Masayuki,Suzuki, Hitomi. "Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios". . p. 2326 - 2335. Retrieved 2007/10/03.
• 2、 Fisher,Dershem,Prewitt. "Meta-substituent effects on benzyl free-radical stability". . p. 1040 - 1043. Retrieved 2007/10/02.