2-Nitrotoluene

Base Information

• Chemical Name: 2-Nitrotoluene
• CAS No.: 88-72-2
• Deprecated CAS: 57158-05-1
• Molecular Formula: C7H7NO2
• Molecular Weight: 137.138
• Hs Code.: 29042000
• European Community (EC) Number: 201-853-3,215-311-9
• ICSC Number: 0931
• NSC Number: 9577
• UN Number: 1664
• UNII: 6Q9N88YIAY
• DSSTox Substance ID: DTXSID4025791
• Nikkaji Number: J3.906C
• Wikipedia: 2-Nitrotoluene
• Wikidata: Q2533785
• Metabolomics Workbench ID: 54817
• ChEMBL ID: CHEMBL47047
• Mol file: 88-72-2.mol

Synonyms:1-methyl-2-nitrobenzene;2-nitrotoluene;o-nitrotoluene;ortho-nitrotoluene

Chemical Property of 2-Nitrotoluene

Chemical Property:

• Appearance/Colour: light yellow to darker yellow-green liquid
• Vapor Pressure: 0.155mmHg at 25°C
• Melting Point: -9 °C
• Refractive Index: n20/D 1.546(lit.)
• Boiling Point: 221.999 °C at 760 mmHg
• Flash Point: 106.111 °C
• PSA: 45.82000
• Density: 1.163 g/cm³
• LogP: 2.42640
• Storage Temp.: 2-8°C
• Solubility.: 0.65g/l (experimental)
• Water Solubility.: 0.44 g/L (20 ºC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 137.047678466
• Heavy Atom Count: 10
• Complexity: 130
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

2-Nitrotoluene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,F
• Hazard Codes: T,N,F
• Statements: 45-46-22-51/53-62-36/37/38-23/24/25-11-36-20/21/22
• Safety Statements: 53-45-61-27-16-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic,Aromatic
• Canonical SMILES: CC1=CC=CC=C1[N+](=O)[O-]
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the liver, blood and testes. This substance is probably carcinogenic to humans. May cause heritable genetic damage to human germ cells. Animal tests show that this substance possibly causes toxic effects upon human reproduction.
• Production method: Nitrify toluene with mixed acid to generate mixed nitrotoluene, which mainly consists of o-nitrotoluene (about two-thirds) and p-nitrotoluene (about one-third). The mixed nitrotoluene can be separated to get the pure product. Add toluene to the reactor and cool to below 25℃. Then add the mixed acid (ie, 25-30% of nitric acid, 55-58% of sulfuric acid and 20-21% of water) and control the temperature not exceeding 50℃. Stir for 1-2h, and then stand for 6h. Separate the generated nitrotoluene, and wash them with water and alkali liquor to remove unreacted toluene and aliphatic compound. The crude nitrotoluene products consist of 55-60% of o-nitrotoluene, 2-5% of m-nitrotoluene and 35-40% of p-nitrotoluene, with a yield of 90-95%. The various isomers can be separated by crude distillation and crystallization according to the difference of the boiling point and melting point. Namely, first distill the crude nitrotoluene under vacuum to separate out the majority of o-nitrotoluene. And then the residual fraction containing more p-nitrotoluene is separated by vacuum distillation, and cooled for crystallization and separated to obtain the finished products. The tarry substance with high boiling point remains in the still. M-nitrotoluene remains in the mother liquor separated out the p-nitrotoluene, and can be obtained by rectification after repeated accumulation. The purity of ortho and para nitrotoluene can respectively reach 98% and 99%. The domestic process is the two-pot series process, and the reaction temperature of the main pot is 40-45℃ and the second pot is 50-55℃. The preparation of mixed acid is roughly similar, including 26-28% of nitric acid, 56-57% of sulfuric acid and 16-18% of water. The raw material consumption quota: toluene (98%) 800kg/t, nitric acid (98%) 470kg/t, sulfuric acid (92.5%) 450kg/t, caustic soda (42%) 100kg /t
• Description: o-Nitrotoluene is a yellow-coloured liquid. It is used for the synthesis of a variety of industrial products. These include to synthesise agricultural and rubber chemicals, azo and sulphur dyes, and dyes for cotton, wool, silk, leather, and paper. O-nitrotoluene decomposes on contact with strong oxidants, reducing agents, acids, or bases producing toxic fumes, nitrogen oxides, and carbon monoxide.
• Physical properties: Clear, colorless to pale yellowish combustible liquid with a faint, aromatic odor. May darken on exposure to air.
• Uses: 2-Nitrotoluene is a nitroaromatic compound. It is used in the synthesis of intermediates for azo dyes, sulfur dyes, rubber chemicals, and agriculture chemicals; typical intermediates are o-toluidine, o-nitrobenzaldehyde, 2-nitro-4-chlorotoluene, 2-nitro-6-chlorotoluene, 2-amino-4-chlorotoluene (Fast Scarlet TR Base), and 2-amino-6-chlorotoluene (Fast Red KB Base). 2-Nitrotoluene is used as an intermediate for the o-toludine synthesis, which finds application in the dyestuff industry. It is employed as a reagent in detecting and photometric determining oxidizing agent. It is also used in the determination of prussic acid content in the air. It acts as a precursor to prepare 2-amino-4-chlorotoluene, 2-amino-6-chlorotoluene, nitrotoluenesulfonic acids and toluene nitrosulfonic chlorides. It acts as a nitrogen supplement in the culture medium of pseudomonas sp. strain ClS1. It acts as a carbon and energy supplement in the culture medium of Pseudomonas sp. strain JS42.

Technology Process of 2-Nitrotoluene

There total 166 articles about 2-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: 100.0%

2-(2-nitrophenyl)acetic acid (3740-52-1) → 1-methyl-2-nitrobenzene (88-72-2)

Guidance literature:

copper(I) oxide; In acetonitrile; at 50 ℃;

DOI:10.1016/0040-4020(84)85005-X

Reference yield: 24.5%

toluene (108-88-3,15644-74-3,16713-13-6) → 1-methyl-3-nitrobenzene (99-08-1) + 1-methyl-4-nitrobenzene (99-99-0) + 1-methyl-2-nitrobenzene (88-72-2) + benzaldehyde (100-52-7)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; trifluoroacetic acid; for 72h; Yield given; Ambient temperature;

Reference yield:

toluene (108-88-3,15644-74-3,16713-13-6) → 1-methyl-4-nitrosobenzene (623-11-0) + 1-methyl-4-nitrobenzene (99-99-0) + 1-methyl-2-nitrobenzene (88-72-2) + 2-nitrosotoluene (611-23-4)

Guidance literature:

With nitric oxide; In trifluoroacetic acid; at 38 ℃; Rate constant; Kinetics; Mechanism;

upstream raw materials:

piperidine

2-(2-nitrophenyl)acetic acid

tetrachloromethane

benzaldehyde

Downstream raw materials:

N-(2-methylphenyl)pyridine-2-thiocarboxamide

2-nitrophenylmethyl bromide

2,2'-dimethylazobenzene

N,2-dimethylaniline

Refernces

• 1、 Prins,Kogelbauer,Haouas,Bernasconi. "An NMR study of the nitration of toluene over zeolites by HNO3-Ac2O". . p. 5067 - 5075. Retrieved 2001.
• 2、 Chen, Pengfei,Du, Mingxing,Lei, He,Wang, Yan,Zhang, Guoliang,Zhang, Fengbao,Fan, Xiaobin. "SO42 -/ZrO2-titania nanotubes as efficient solid superacid catalysts for selective mononitration of toluene". . p. 47 - 50. Retrieved 2012.
• 3、 Cornelis, Andre,Delaude, Lionel,Gerstmans, Andre,Laszlo, Pierre. "A PROCEDURE FOR QUANTITATIVE REGIOSELECTIVE NITRATION OF AROMATIC HYDROCARBONS IN THE LABORATORY". . p. 5657 - 5660. Retrieved 1988.
• 4、 Cornelis, Andre,Delaude, Lionel,Gerstmans, Andre,Laszlo, Pierre. "A PROCEDURE FOR QUANTITATIVE REGIOSELECTIVE NITRATION OF AROMATIC HYDROCARBONS IN THE LABORATORY". . p. 5909 - 5912. Retrieved 1988.
• 5、 Cornelis, Andre,Gerstmans, Andre,Laszlo, Pierre. "REGIOSELECTIVE LIQUID-PHASE TOLUENE NITRATION WITH MODIFIED CLAYS AS CATALYSTS". . p. 1839 - 1842. Retrieved 1988.
• 6、 Zhang,Peng,Zhao. "Metal ion-exchanged bentonites as useful solid catalysts for regioselective nitration of toluene". . p. 3511 - 3512. Retrieved 2013.
• 7、 Armatas, Gerasimos S.,Daikopoulou, Vassiliki,Koutsouroubi, Eirini D.,Lykakis, Ioannis N.,Skliri, Euaggelia. "Selective Mild Oxidation of Anilines into Nitroarenes by Catalytic Activation of Mesoporous Frameworks Linked with Gold-Loaded Mn3O4 Nanoparticles". . . Retrieved 2021/11/01.
• 8、 Ge, Jingjie,Yin, Peiqun,Chen, Ye,Cheng, Hongfei,Liu, Jiawei,Chen, Bo,Tan, Chaoliang,Yin, Peng-Fei,Zheng, Hong-Xing,Li, Qiang-Qiang,Chen, Shuangming,Xu, Wenjie,Wang, Xiaoqian,Wu, Geng,Sun, Rongbo,Shan, Xiang-Huan,Hong, Xun,Zhang, Hua. "Ultrathin Amorphous/Crystalline Heterophase Rh and Rh Alloy Nanosheets as Tandem Catalysts for Direct Indole Synthesis". . . Retrieved 2021/01/29.