3-Bromo-5-nitrotoluene

Base Information

• Chemical Name: 3-Bromo-5-nitrotoluene
• CAS No.: 52488-28-5
• Molecular Formula: C7H6BrNO2
• Molecular Weight: 216.034
• Hs Code.: 2904909090
• European Community (EC) Number: 257-955-3
• DSSTox Substance ID: DTXSID00200482
• Nikkaji Number: J295.675F
• Wikidata: Q72448800
• Mol file: 52488-28-5.mol

Synonyms:3-Bromo-5-nitrotoluene;52488-28-5;1-bromo-3-methyl-5-nitrobenzene;Benzene, 1-bromo-3-methyl-5-nitro-;MFCD06659815;EINECS 257-955-3;(-)-ephedrin;SCHEMBL810499;3-BROMO-5-NITROTLOLUENE;DTXSID00200482;AMY40730;BCP26878;CL8829;AKOS015969438;AB26378;AC-23465;AS-18924;SY013063;CS-0153266;FT-0640072;A15617;EN300-100538

Chemical Property of 3-Bromo-5-nitrotoluene

Chemical Property:

• Vapor Pressure: 0.012mmHg at 25°C
• Melting Point: 68-72 °C
• Refractive Index: 1.592
• Boiling Point: 269.5 °C at 760 mmHg
• Flash Point: 120 °C
• PSA: 45.82000
• Density: 1.615 g/cm³
• LogP: 3.18890
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 214.95819
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-Bromo-5-nitrotoluene

There total 17 articles about 3-Bromo-5-nitrotoluene 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: 99.0%

(3-bromo-5-methylphenyl)boronic acid (849062-36-8) → 1-bromo-3-methyl-5-nitrobenzene (52488-28-5)

Guidance literature:

With nitric acid; In 1,2-dichloro-ethane; at 70 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.1c00886

Reference yield: 66.0%

2-bromo-4-methyl-6-nitroaniline (827-24-7) → 1-bromo-3-methyl-5-nitrobenzene (52488-28-5)

Guidance literature:

With sulfuric acid; sodium nitrite; In ethanol; at 73 - 78 ℃;

DOI:10.1016/j.bmc.2011.08.043

Reference yield: 59.0%

4-methyl-2-nitrobenzoic acid (27329-27-7) → 1-bromo-3-methyl-5-nitrobenzene (52488-28-5)

Guidance literature:

With copper(I) oxide; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bismuth (III) nitrate pentahydrate; oxygen; sodium bromide; In dimethyl sulfoxide; at 170 ℃; for 10h; regioselective reaction; Schlenk technique; Green chemistry;

DOI:10.1021/acs.orglett.9b00460

upstream raw materials:

1-bromo-2-iodo-5-methyl-3-nitrobenzene

2-bromo-4-methyl-6-nitroaniline

2-bromo-6-methyl-4-nitroaniline

4-bromo-2-methyl-6-nitroaniline

Downstream raw materials:

(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-(6-{[4-(3-methyl-5-nitrophenyl)-3-butyn-1-yl]oxy}hexyl)-1,3-oxazolidin-2-one

5-Methyl-3-nitrobenzoic acid

Refernces

• 1、 Baucom, Kyle D.,Brown, Derek B.,Caille, Seb,Murray, James I.,Quasdorf, Kyle,Silva Elipe, Maria V.. "Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid". supporting information. . Retrieved 2021/06/30.
• 2、 Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel. "meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation". . p. 8018 - 8023. Retrieved 2019/05/29.