1-Chloro-4-nitrobenzene

Base Information

• Chemical Name: 1-Chloro-4-nitrobenzene
• CAS No.: 100-00-5
• Molecular Formula: C6H4ClNO2
• Molecular Weight: 157.556
• Hs Code.: 29049085
• European Community (EC) Number: 202-809-6
• ICSC Number: 0846
• NSC Number: 9792
• UN Number: 1578
• UNII: CVL66U249D
• DSSTox Substance ID: DTXSID5020281
• Nikkaji Number: J3.586F
• Wikipedia: 4-Nitrochlorobenzene
• Wikidata: Q4637187
• ChEMBL ID: CHEMBL56970
• Mol file: 100-00-5.mol

Synonyms:1-chloro-4-nitrobenzene;4-chloronitrobenzene;p-chloronitrobenzene;p-nitrochlorobenzene;PNCB

Chemical Property of 1-Chloro-4-nitrobenzene

Chemical Property:

• Appearance/Colour: light yellow crystals
• Vapor Pressure: 0.09 mm Hg ( 25 °C)
• Melting Point: 81-84 °C
• Refractive Index: 1.58
• Boiling Point: 242 °C at 760 mmHg
• Flash Point: 94.5 °C
• PSA: 45.82000
• Density: 1.391 g/cm³
• LogP: 2.77140
• Solubility.: Soluble in acetone and alcohol (Weast, 1986)
• Water Solubility.: Insoluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 156.9930561
• Heavy Atom Count: 10
• Complexity: 126
• Transport DOT Label: Poison

Purity/Quality:

4-Chloronitrobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 23/24/25-40-48/20/21/22-51/53-68
• Safety Statements: 28-36/37-45-61-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])Cl
• Recent EU Clinical Trials: EMERA006- A pilot, exploratory, randomised, placebo-controlled, double blinded, cross-over, Phase 2a study to explore efficacy and safety of NBMI treatment in patients with Progressive Supranuclear Palsy (PSP) or Multiple System Atrophy (MSA).
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: The substance may cause effects on the blood. This may result in the formation of methaemoglobin.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Physical properties: p-Nitrochlorobenzene is a yellow crystalline solid with a sweet odor.
• Uses: 4-Nitrochlorobenzene is an important intermediate in the manufacture of azo dyes and sulfide dyes, the drugs finasteride and paracetamol, the pesticide herbicide, etc. It is also the raw material of rubber antioxidant 4010. p-Nitrochlorobenzene is largely used to produce p-nitrophenol with smaller production of p-nitroaniline. Manufacture of dyes, rubber, and agricultural chemicals

Technology Process of 1-Chloro-4-nitrobenzene

There total 179 articles about 1-Chloro-4-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: 86.0%

chlorobenzene (108-90-7) → 4-chlorobenzonitrile (100-00-5) + 2-Chloronitrobenzene (88-73-3)

Guidance literature:

With nickel ammonium sulfate; nitric acid; In chloroform; water; at 20 ℃; for 3h;

DOI:10.1081/SCC-100103545

Reference yield: 71.3%

1-chloro-4-isopropylbenzene (2621-46-7) → 4-chloro-3-nitroisopropylbenzene (76611-15-9) + 1-chloro-4-isopropyl-3-nitrobenzene (76611-16-0) + 4-chlorobenzonitrile (100-00-5)

Guidance literature:

With nitric acid; In sulfuric acid; at 25 ℃;

DOI:10.1039/P29800001606

Reference yield: 33.0%

p-nitrobenzenediazonium (14368-49-1) → 4-chlorobenzonitrile (100-00-5)

Guidance literature:

With tin(II); chloride; copper(II) nitrate; In water; Ambient temperature;

DOI:10.1016/S0040-4039(00)74537-0

upstream raw materials:

styrene

N-nitrosamide of N-(4-nitrophenyl)acetamide

4-nitro-phenol

ethanol

Downstream raw materials:

1-(4-nitro-phenyl)-pyrrolidine

1-(4-nitrophenyl)piperidine

1-morpholino-4-nitrobenzene

4,4'-bis(chloro)azoxybenzene

Refernces

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• 2、 Yi, Wen-Bin,Cai, Chun. "Polymer-supported ytterbium perfluorooctanesulfonate [Yb(OPf)3]: A recyclable catalyst for organic reactions". . p. 524 - 528. Retrieved 2008.
• 3、 Picard, Martin,Gross, Juergen,Luebbert, Ellen,Toelzer, Sabine,Krauss, Susanne,Van Pee, Karl-Heinz,Berkessel, Albrecht. "Metal-Free Bacterial Haloperoxidases as Unusual Hydrolases: Activation of H2O2 by the Formation of Peracetic Acid". . p. 1196 - 1199. Retrieved 1997.
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• 5、 Cornella, Josep,Sanchez, Carolina,Banawa, David,Larrosa, Igor. "Silver-catalysed protodecarboxylation of ortho-substituted benzoic acids". . p. 7176 - 7178. Retrieved 2009.
• 6、 Lee, Young Min,Moon, Mi Eun,Vajpayee, Vaishali,Filimonov, Victor D.,Chi, Ki-Whan. "Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts". . p. 7418 - 7422. Retrieved 2010.
• 7、 Olah,G.A.,Tolgyesi,W.S.. "-". . p. 2053 - 2055. Retrieved 1961.
• 8、 Hodgson,Birtwell,Walker. "-". . p. 770,775. Retrieved 1941.
• 9、 McCormack. "-". . p. 1333. Retrieved 1937.
• 10、 Kolker,Waters. "-". . p. 1136,1138,1141. Retrieved 1964.