Nitrobenzene
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| Nitrobenzene | |
|---|---|
| Image:Nitrobenzene-2D-skeletal.png | |
| Image:Nitrobenzene-3D-vdW.png | |
| Other names | Nitrobenzol Oil of mirbane |
| Identifiers | |
| CAS number | |
| RTECS number | QJ0525000 |
| SMILES | C1=CC=C(C=C1)[N+](=O)[O-] |
| Properties | |
| Molecular formula | C6H5NO2 |
| Molar mass | 123.06 g/mol |
| Appearance | colorless liquid |
| Density | 1.199 g/cm3 |
| Melting point |
5.85 °C |
| Boiling point |
210.9 °C |
| Solubility in water | 0.19 g/100 ml at 20 °C |
| Hazards | |
| EU classification | Toxic (T) Carc. Cat. 3 Repr. Cat. 3 Dangerous for the environment (N) |
| R-phrases | R23/24/25, R40, R48/23/24, R51/53, R62 |
| S-phrases | (S1/2), S28, S36/37, S45, S61 |
| Flash point | 88 °C |
| Autoignition temperature | 525 °C |
| Related Compounds | |
| Related compounds | Aniline Benzenediazonium Nitrosobenzene |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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Overview
Nitrobenzene, also known as nitrobenzol or oil of mirbane, is a poisonous organic compound with an almond odor and chemical formula C6H5NO2. It may be found as either bright yellow crystals or an oily water-insoluble liquid.
It is used as a solvent and as a mild oxidizing agent. It is most frequently used specifically in the manufacture of aniline, but also used in the manufacture of insulating compounds and polishes.
Uses
While nitrobenzene is primarily used in the production of aniline and aniline derivatives, such as methylene diphenyl diisocyanate (MDI), it also finds use in the manufacture of rubber chemicals, pesticides, dyes, and pharmaceuticals. Nitrobenzene is also used in shoe and floor polishes, leather dressings, paint solvents, and other materials to mask unpleasant odors. Substitution reactions with nitrobenzene are used to form m-derivatives (Mannsville 1991; Sittig 1991)[citation needed]. Redistilled, as oil of mirbane, nitrobenzene has been used as an inexpensive perfume for soaps. A significant merchant market for nitrobenzene is its use in the production of the analgesic paracetamol (also known as acetaminophen) (Mannsville 1991). Nitrobenzene is also used in Kerr cells, as it has an unusually large Kerr constant.
Production
There were four producers of nitrobenzene in the United States in 1991: First Chemicals Corporation, Mobay, DuPont Chemicals, and Rubicon Inc. In 1991, the estimated total production capacity of nitrobenzene in the U.S. was 617000 tonnes (Mannsville 1991)[citation needed].
The classic method for forming nitrobenzene is to react benzene with a mixture of concentrated sulfuric acid and nitric acid. This mixture of acids forms an electrophile which reacts with the benzene in an electrophilic aromatic substitution reaction. This reaction is often known as a nitration reaction.
The nitric acid is protonated by the sulphuric acid to form H2NO3+ which then loses water to form NO2+. The concentrated sulphuric acid has a high affinity for the water, this helps the reaction go.
References
External links
- International Chemical Safety Card 0065
- NIOSH Pocket Guide to Chemical Hazards
- IARC Monograph: "Nitrobenzene"
- US EPA factsheet
cs:Nitrobenzen de:Nitrobenzolit:Nitrobenzene lv:Nitrobenzolssk:Nitrobenzén fi:Nitrobentseeni
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
