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Nitrobenzene

Base Information Edit
  • 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
Nitrobenzene

Synonyms:nitrobenzene

Suppliers and Price of Nitrobenzene
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Nitrobenzene
  • 10g
  • $ 185.00
  • TCI Chemical
  • Nitrobenzene
  • 500G
  • $ 27.00
  • Sigma-Aldrich
  • Nitrobenzene for synthesis
  • 100 mL
  • $ 20.16
  • Sigma-Aldrich
  • Nitrobenzene PESTANAL?, analytical standard
  • 1 mL
  • $ 18.30
  • Sigma-Aldrich
  • Nitrobenzene PESTANAL , analytical standard
  • 1ml-f
  • $ 17.70
  • Sigma-Aldrich
  • Nitrobenzene for synthesis
  • 1 L
  • $ 61.51
  • Sigma-Aldrich
  • Nitrobenzene PESTANAL?, analytical standard
  • 5 mL
  • $ 57.40
  • Sigma-Aldrich
  • Nitrobenzene PESTANAL , analytical standard
  • 5ml-f
  • $ 55.60
  • Sigma-Aldrich
  • Nitrobenzene ACS reagent, ≥99.0%
  • 25ml
  • $ 44.20
  • Sigma-Aldrich
  • Nitrobenzene solution certified reference material, 5000?μg/mL in methanol
  • 1 mL
  • $ 38.60
Total 16 raw suppliers
Chemical Property of Nitrobenzene Edit
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): ToxicT,DangerousN,Flammable
  • 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:
Guidance literature:
With sodium nitrite; In chloroform; water; at 56 ℃; for 3h; Title compound not separated from byproducts;
DOI:10.1007/BF00954097
Refernces Edit

Redox-Neutral Access to Sultams from 2-Nitrochalcones and Sulfur with Complete Atom Economy

10.1021/acs.orglett.7b01766

The research focuses on the development of a novel, catalyst-free, redox-neutral, and atom-economical method for synthesizing sultams from 2-nitrochalcones and elemental sulfur. The experiments involve heating 2-nitrochalcones with sulfur in the presence of a base such as 3-picoline or N-methylmorpholine, leading to the formation of sultams with complete atom economy. The reaction conditions were optimized through a series of tests, varying the base, temperature, and amount of sulfur. The scope of the reaction was explored with various chalcones bearing different substituents on the benzoyl and nitrobenzene rings. The connectivity of the synthesized sultams was confirmed by X-ray diffraction studies and NMR spectroscopy. The study also investigated the reaction mechanism and found that the choice of basic additive was crucial for the success of the reaction. The research demonstrates a versatile and environmentally friendly approach to synthesizing sultams, which are important scaffolds in medicinal chemistry.

Competition between Radical and Nonradical Reactions of Halonitrobenzenes in Alkaline Alcoholic Solutions

10.1021/jo00298a044

The research investigates the reactivity of monohalonitrobenzenes in alkaline 2-propanol solutions of potassium 2-propoxide, focusing on the competition between radical and nonradical reaction pathways. The study aims to identify distinct reaction paths, including hydro dehalogenation to nitrobenzene, alkoxy dehalogenation via the SNAr mechanism, and nitro reduction to azoxy and anilino derivatives via nitroso intermediates. The research concludes that, with the exception of 2- and 4-fluoronitrobenzene, radical processes are generally faster than the SNAr reaction. The study also reveals that the presence of oxygen and cation complexing agents, such as 18-crown-6, significantly influence the reaction pathways and product distributions. Key chemicals used in the process include various halonitrobenzenes (X = F, Cl, Br, I), potassium 2-propoxide, 2-propanol, and 18-crown-6 ether.

Synthesis of 5-propynyloxycycloalkanepyrimidines and their selectivity and reactivity in intramolecular Diels-Alder reactions

10.1016/S0040-4020(01)88723-8

The research focuses on the synthesis of 5-propynyloxycycloalkane pyrimidines (IIIA, IIIB, IIIC, and IIID) and their selective and reactive behavior in intramolecular Diels-Alder reactions with inverse electron demand, followed by a retro Diels-Alder reaction. The compounds IIIA and IIIB favor the extrusion of X-CH2CN, yielding 3-(3-cyanopropyl)-1,3-dihydro-6-phenyl-R1-R2-furo[3,4-c]pyridines (29-36), while compounds 17 and 21 also yield 4-phenyl-6,7,8,8a-tetrahydro-furo[4,3,2-d]quinoline (38) by expelling HCN or MeCN, respectively. For compounds IIIC and IIID, HCN expulsion is favored over X-CH2CN, leading to the formation of 2H-1,6,7,8,9,9a-hexahydro-4-phenyl-9a-R1-5-aa-l-oxo-benz[~~azulenes (39, 40). The reactivity of these compounds towards cycloaddition is significantly influenced by the nature of the substituent R2 when R1 = H, but less so when R1 = Me. The ratio of products V and VI mainly depends on the nature of -X-. The synthesis of these pyrimidines involves starting from their keto precursors (I) and using various reagents such as NaBH4, Grignard reagents, and propargyl bromide in the presence of sodium hydride. The intramolecular Diels-Alder reactions are performed by heating the compounds III in nitrobenzene at 140°C, and the products are analyzed using 1H-NMR spectroscopy.

Direct Aromatic Periodination

10.1021/jo00191a003

The study explores a direct method for the periodination of aromatic compounds using periodic acid (HIO?) and iodine in concentrated sulfuric acid. This method allows for the exhaustive iodination of unactivated aromatic substrates such as benzene, nitrobenzene, benzoic acid, chlorobenzene, phthalic anhydride, and toluene, converting them into their respective periodo derivatives. The study also reports the conversion of benzonitrile to pentaiodobenzamide. The direct periodination method is compared favorably to the existing mercuration/iododemercuration sequence in terms of reaction time and purity of products. The study highlights the versatility of the method, demonstrating that partially iodinated products can be obtained under less vigorous conditions. Additionally, the study discusses the limitations of the method, noting that certain activated aromatics and easily oxidized substrates do not fare well under these conditions. The research provides detailed experimental procedures and characterizations of the synthesized compounds, contributing to the field of organic chemistry by offering a more efficient route for the preparation of polyiodinated and periodinated aromatic compounds.

Route design and development of a MET kinase inhibitor: A copper-catalyzed preparation of an N 1 - Methylindazole

10.1021/op400317z

The study presents an improved route for the synthesis of a MET kinase inhibitor, LY2801653, which is a small molecule with potential therapeutic applications in various types of cancers. The new synthesis process is more efficient, yielding a 22% overall yield over eight steps, compared to the initial 12-step process with a 5.4% yield. Key steps in the process include a Cu-catalyzed cyclization to form an N1-methylindazole ring, selective nitro reduction, a late-stage Suzuki cross-coupling, and a base-promoted Boc deprotection. The chemicals used in the study serve various purposes: 3-hydroxybenzaldehyde as the starting material, copper catalyst for cyclization, nitrobenzene for the formation of aryl ether, and Boc-protected pyrazole as a key intermediate. The study also addresses safety concerns and optimizes the synthesis for multikilogram operations, focusing on minimizing the use of hazardous chemicals and improving the overall efficiency of the process.

Displacement of an Aromatic Nitro Group using Phenoxides

10.1039/c39870001373

The study investigates a new method for preparing diphenyl ethers by displacing an aromatic nitro group with phenoxides. It involves using substituted nitrobenzenes (2a-d) and various phenoxides, including sodium phenoxide and 2,6-disubstituted phenoxides, in dry dimethyl sulphoxide at 90°C for 16 hours. The nitrobenzenes act as the substrates, while the phenoxides serve as nucleophiles to displace the nitro group, forming diphenyl ethers. The study highlights that this method is particularly effective for synthesizing hindered diphenyl ethers from weakly nucleophilic phenoxides. The results show that the yield of diphenyl ethers is affected by the reaction temperature and the specific phenoxide used. Additionally, the study provides insights into the reaction mechanism, suggesting a radical nature rather than an anionic nucleophilic displacement mechanism in certain cases.

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