Nitrobenzene

Base Information

• Chemical Name: Nitrobenzene
• CAS No.: 98-95-3
• Molecular Formula: C6H5NO2
• Molecular Weight: 124.119
• Hs Code.: 29042010
• European Community (EC) Number: 202-716-0
• ICSC Number: 0065
• NSC Number: 9573
• UN Number: 1662
• UNII: E57JCN6SSY
• DSSTox Substance ID: DTXSID3020964
• Nikkaji Number: J1.430.487H,J3.989F
• Wikipedia: Nitrobenzene
• Wikidata: Q407290
• NCI Thesaurus Code: C44410
• Metabolomics Workbench ID: 49655
• ChEMBL ID: CHEMBL15750
• Mol file: 98-95-3.mol

Synonyms:nitrobenzene

Chemical Property of Nitrobenzene

Chemical Property:

• Appearance/Colour: yellow liquid
• Vapor Pressure: 0.15 mm Hg ( 20 °C)
• Melting Point: 5-6 ºC(lit.)
• Refractive Index: n20/D 1.551(lit.)
• Boiling Point: 210.799 ºC at 760 mmHg
• PKA: 3.98(at 0℃)
• Flash Point: 81.413 ºC
• PSA: 45.82000
• Density: 1.216 g/cm³
• LogP: 2.11800
• Storage Temp.: 2-8°C
• Solubility.: 1.90g/l
• Water Solubility.: slightly soluble
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 123.032028402
• Heavy Atom Count: 9
• Complexity: 102
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Nitrobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,F
• Hazard Codes: T,N,F,Xn
• Statements: 23/24/25-40-48/23/24-51/53-62-39/23/24/25-11-36/37/38-60-52/53-48/23/24/25-36-20/21/22
• Safety Statements: 28-36/37-45-61-28A-16-7-27-53-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: C1=CC=C(C=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; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Exposure could cause lowering of consciousness. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the blood, spleen and liver. This substance is possibly carcinogenic to humans. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• Description: Nitrobenzene (chemical formula: C6H4NO2) is a yellowish, oily, aromatic nitro-compound. The most important application of nitrobenzene (consuming 95%) is for the manufacturing of aniline, which is an important industrial precursor. Besides aniline, it can also be used to generate related derivatives such as azobenzene, nitrosobenzene and phenylhydroxylamine. Moreover, it can be used for the production of lubricating oils, dyes, drugs, pesticides, and synthetic rubber. Another special application of it is masking unpleasant odors emitting from shoe, floor polisher, and leather as well as paint solvents. In addition, it can sometime used as a solvent, especially for electrophilic reagents in the laboratory. The nitrobenzene is mainly manufactured through the nitration of benzene with the mixture of concentrated sulfuric acid, water and nitric acid. However, the reaction process is quite dangerous due to the exothermicity of the reaction. Nitrobenzene is a greenish-yellow crystal or yellow oily liquid, and is slightly soluble in water. The primary hazard of nitrobenzene is toxicity; however, it is also combustible. The boiling point is about 410°F, the flash point is 190°F, and the ignition temperature is 900°F. The specific gravity is 1.2, which is heavier than water, and the material will sink to the bottom. The vapor density is 4.3, which is heavier than air. Nitrobenzene is toxic by ingestion, inhalation, and skin absorption, with a TLV of 1 ppm in air. The four-digit UN identification number is 1652. The NFPA 704 designation is health 3, flammability 2, and reactivity 1. Nitrobenzene is a nitro hydrocarbon derivative, but it is not very explosive. The primary uses are as a solvent, an ingredient of metal polishes and shoe polishes, and in the manufacture of aniline.
• Uses: Nitrobenzene is a synthetic, volatile compound produced primarily for use to manufacture aniline. It is also used as a solvent in refining petroleum and lubricating oils, and in production of dyes, synthetic rubber, pesticides, and drugs including acetaminophen and metoclopramide. Small amounts of nitrobenzene are used as a flavoring agent for soaps and as a solvent for shoe dyes (HSDB, 2009; IARC, 1996). Dinitrobenzene isomers (1, 2-, 1, 3-, and 1, 4-) are used in organic synthesis of dyes, pesticides, and industrial solvents. 1,3-Dinitrobenzene and 1,3,5-trinitrobenzene are chemicals found in the production of explosives. Nitrobenzene and all isomers (1,2-, 1,3-, and 1,4-) of dinitrobenzene can be absorbed by all routes of exposures and may cause irritation in the respiratory tract and skin. 1,3- Dinitrobenzene and 1,3,5-trinitrobenzene are of severe explosive hazard. Most nitrobenzene (97%) is used in the manufacture of aniline (IARC 1996, HSDB 2009). Miscellaneous uses include the manufacture of benzidine, quinoline, azobenzene, pyroxylin compounds, isocyanates, pesticides, rubber chemicals, pharmaceuticals, and dyes such as nigrosines and magenta. Nitrobenzene is found in soaps and shoe and metal polishes and is used as a solvent for cellulose ester, in modifying esterification of cellulose acetate, and in refining lubricating oils (HSDB 2009). Nitrobenzene also is used as a solvent in petroleum refining and the synthesis of other organic compounds, such as acetaminophen (ATSDR 1990). The primary use of nitrobenzene is in the captive production of aniline, with about 97.5% of nitrobenzene production consumed in this process. The major use of aniline is in the manufacture of polyurethanes. Nitrobenzene is also used as a solvent in petroleum refining, in the manufacture of cellulose ethers and acetate, and in Friedel-Crafts reactions to hold the catalyst in solution. It is also used in the synthesis of other organic compounds including acetaminophen, which is an over-the-counter analgesic commonly known as Tylenol?.Nitrobenzene is used as a flavoring agent, a perfume for soaps and as a solvent for shoe dyes. Nitrobenzene is an organic compound used a standard for detection and analyses as well as its removal from the environment. The compound’s cytotoxic effects have been studied in a hepatocarcinoma cell line. For the manufacture of aniline; in soaps, shoe polishes; for refining lubricating oils; manufacture of pyroxylin Compounds.
• Physical properties: Clear, light yellow to brown, oily liquid with an almond-like or shoe polish odor. May darken on exposure to air. An experimentally determined odor threshold concentration of 4.7 ppbv was reported by Leonardos et al. (1969). A detection odor threshold concentration of 9.6 mg/m3 (1.9 ppmv) was determined by Katz and Talbert (1930).

Technology Process of Nitrobenzene

There total 863 articles about Nitrobenzene 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: 98.0%

(4-nitrophenyl)(phenyl)iodonium tetrafluoroborate → p-nitrobenzene iodide (636-98-6) + para-dinitrobenzene (100-25-4) + iodobenzene (591-50-4) + nitrobenzene (98-95-3,26969-40-4)

Guidance literature:

With sodium nitrite; In chloroform; water; at 56 ℃; for 1h;

DOI:10.1007/BF00954097

Reference yield: 90.0%

p-methoxyphenyl(phenyl)iodonium tetrafluoroborate (733-53-9) → iodobenzene (591-50-4) + para-methoxynitrobenzene (100-17-4) + para-iodoanisole (696-62-8) + nitrobenzene (98-95-3,26969-40-4)

Guidance literature:

With sodium nitrite; In chloroform; water; at 56 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1007/BF00954097

Reference yield: 80.0%

N,N-Dimethyl-4-nitroaniline (100-23-2) → N-methyl-N-nitrosoaniline (614-00-6) + nitrobenzene (98-95-3,26969-40-4) + N-methyl(p-nitroaniline) (100-15-2) + N-methyl-N-nitroso-4-nitroaniline (943-41-9)

Guidance literature:

With n-Butyl nitrite; ammonium chloride; water; for 2h; Heating;

DOI:10.1139/v97-054

upstream raw materials:

methanol

meta-dinitrobenzene

N-nitropiperidine

diethyl ether

Downstream raw materials:

1,4-bis-(2-hydroxyethylamino)anthraquinone

2-(2,4-dinitro-styryl)-anthraquinone

2,4,6-trinitrochlorobenzene

Azobenzene

Refernces

• 1、 Sutcliffe, Leslie H.. "Kinetic Electron Spin Resonance Investigation of the Monohydronitro Free Radical of 2,3,5,6-Tetrachloronitrobenzene". . p. 1467 - 1470. Retrieved 1985.
• 2、 -. "Self-powered continuous nitration method and device". Paragraph 0069-0072. . Retrieved 2021/07/17.
• 3、 Goljani, Hamed,Nematollahi, Davood,Sepehrmansourie, Hassan,Tavakkoli, Zahra,Zolfigol, Mohammad Ali. "New insight into the electrochemical reduction of different aryldiazonium salts in aqueous solutions". . p. 25811 - 25815. Retrieved 2021/08/09.