89-60-1

Basic information

• Product Name: 4-Chloro-3-nitrotoluene
• Synonyms: 4-CHLORO-3-NITROTOLUENE;3-NITRO-4-CHLORO TOLUENE;2-CHLORO-5-METHYLNITROBENZENE;1-CHLORO-4-METHYL-2-NITROBENZENE;M-NITRO-P-CHLOROTOLUENE;1-chloro-4-methyl-2-nitro-benzen;4,3-Chloronitrotoluene;Toluene, 4-chloro-3-nitro-
• CAS NO: 89-60-1
• Molecular Formula: C₇H₆ClNO₂
• Molecular Weight: 171.58
• EINECS: 201-922-8
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 89-60-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 7 °C(lit.)
• Boiling Point: 260 °C745 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear yellow liquid
• Density: 1.297 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0156mmHg at 25°C
• Refractive Index: n20/D 1.558(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 511055
• CAS DataBase Reference: 4-Chloro-3-nitrotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-nitrotoluene(89-60-1)
• EPA Substance Registry System: 4-Chloro-3-nitrotoluene(89-60-1)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36/37/38-20/21/22-52/53-51/53-36/38-33
• Safety Statements: 36/37/39-26-61-57-36/37-23-9
• RIDADR: UN 2433 6.1/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 89-60-1(Hazardous Substances Data)

Usage

Description

4-Chloro-3-nitrotoluene is a clear yellow liquid that is an organic compound with the molecular formula C7H6ClNO2. It is characterized by the presence of a chlorine atom at the 4-position and a nitro group at the 3-position on a toluene ring. 4-Chloro-3-nitrotoluene has been studied using vibrational spectral analysis, including Raman and IR spectroscopy, to understand its chemical properties.

Uses

Used in Pharmaceutical Synthesis:
4-Chloro-3-nitrotoluene is used as a key intermediate in the synthesis of quinazoline-2,4(1H,3H)-dione derivatives, which are selective inhibitors of PARP-2. These inhibitors have potential applications in the development of treatments for various diseases, including cancer.
Used in Organic Chemistry:
4-Chloro-3-nitrotoluene has been utilized in the synthesis of 4-(2-hydroxyethylamino)-3-nitrotoluene, which is an important compound in organic chemistry. This synthesis demonstrates the versatility of 4-chloro-3-nitrotoluene as a building block for the creation of various organic molecules with different applications.

InChI:InChI=1/C7H6ClNO2/c1-5-2-3-6(8)7(4-5)9(10)11/h2-4H,1H3

Upstream product

• 89-62-3 4-methyl-2-nitroaniline 
• 106-43-4 para-chlorotoluene 
• 75508-74-6 5-chloro-2-methyl-2-nitrocyclohexa-3,5-dienyl acetate 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 99-08-1 1-methyl-3-nitrobenzene 
• 7782-50-5 chlorine 
• 27329-27-7 4-methyl-2-nitrobenzoic acid 
• 108-88-3 toluene 

Downstream Products

• 13174-88-4 N-(4-methyl-2-nitrophenyl)pyridin-2-amine 
• 101936-32-7 9-(4-methyl-2-nitro-phenyl)-carbazole 
• 31438-18-3 (2-nitro-4-methylphenyl)-4-methylphenylamine 
• 871879-52-6 2-(4-methyl-2-nitro-anilino)-benzaldehyde 
• 20901-98-8 3-nitro-toluene-4-sulfonic acid amide 
• 31183-82-1 Bis-<2-amino-4-methyl-phenyl>-trisulfid 
• 65039-20-5 N-(2-Chloro-5-methylphenyl)-hydroxylamine 
• 3360-45-0 4-chloro-3-nitro-benzylbromide 
• 76274-01-6 2,2'-Dichlor-5,5'-dimethyl-azoxybenzol 
• 52262-63-2 4,N,N-trimethyl-2-nitroaniline 
• 40925-61-9 6-Methylbenzothiazolon 
• 74834-82-5 4-Methoxy-2-(4-methyl-2-nitro-phenylsulfanyl)-6-nitro-phenylamine 
• 26830-95-5 4-methyl-2-nitrobenzonitrile 
• 74834-85-8 4-Ethoxy-2-(4-methyl-2-nitro-phenylsulfanyl)-6-nitro-phenylamine 

Relevant articles and documents

Dehydroxyalkylative halogenation of C(aryl)-C bonds of aryl alcohols

We herein report Cu mediated side-directed dehydroxyalkylative halogenation of aryl alcohols. C(aryl)-C bonds of aryl alcohols were effectively cleaved, affording the corresponding aryl chlorides, bromides and iodides in excellent yields. Aryl alcohols could serve as both aromatic electrophilic and radical synthetic equivalents during the reaction.

Efficient transposition of the sandmeyer reaction from batch to continuous process

The transposition of Sandmeyer chlorination from a batch to a safe continuous-flow process was investigated. Our initial approach was to develop a cascade method using flow chemistry which involved the generation of a diazonium salt and its quenching with copper chloride. To achieve this safe continuous process diazotation, a chemometric approach (Simplex method) was used and extrapolated to establish a fully continuous-flow method. The reaction scope was also examined via the synthesis of several (het)aryl chlorides. Validation and scale-up of the process were also performed. A higher productivity was obtained with increased safety.

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.