102151-33-7

Basic information

• Product Name: 3-CHLORO-4-METHOXYBENZONITRILE
• Synonyms: 3-CHLORO-4-METHOXYBENZONITRILE;3-Chloro-4-methoxybenzonitrile, 97+%;3-CHLORO-4-METHOXYBENZONITRILE v;3-Chloro-4-Methoxybenzonitrile;3-Chloro-4-methoxybenzonitrile 97%;3-Chloro-4-methoxy-carbonitrile
• CAS NO: 102151-33-7
• Molecular Formula: C₈H₆ClNO
• Molecular Weight: 167.59
• EINECS: -0
• Product Categories: Nitrile;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds;Nitriles;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 102151-33-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 107-111 °C(lit.)
• Boiling Point: 265.7 °C at 760 mmHg
• Flash Point: 114.5 °C
• Appearance: /
• Density: 1.25 g/cm³
• Vapor Pressure: 0.00903mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 5926726
• CAS DataBase Reference: 3-CHLORO-4-METHOXYBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-METHOXYBENZONITRILE(102151-33-7)
• EPA Substance Registry System: 3-CHLORO-4-METHOXYBENZONITRILE(102151-33-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 102151-33-7(Hazardous Substances Data)

Usage

General Description

3-Chloro-4-methoxybenzonitrile is a chemical compound with the molecular formula C8H6ClNO and a molecular weight of 169.59 g/mol. It is a nitrile compound with a chlorine atom and a methoxy group attached to a benzene ring. This chemical may be used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is also used as a building block in organic synthesis, particularly in the production of specialty chemicals. 3-Chloro-4-methoxybenzonitrile is typically handled and stored in a controlled environment due to its potential toxicity and reactivity.

InChI:InChI=1/C8H6ClNO/c1-11-8-3-2-6(5-10)4-7(8)9/h2-4H,1H3

Upstream product

• 89978-93-8 3-chloro-4-methoxy-benzoic acid amide 
• 2315-81-3 2-chloro-4-cyanophenol 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 117482-84-5 3-chloro-4-fluorobenzonitrile 
• 4920-79-0 2-chloro-4-nitroanisole 
• 143-33-9 sodium cyanide 
• 37908-96-6 3-chloro-4-methoxy benzoic acid 
• 37908-98-8 methyl 3-chloro-p-anisate 
• 36590-49-5 3-chloro-4-methoxybenzoyl chloride 
• 7677-24-9 trimethylsilyl cyanide 
• 766-51-8 2-Chloroanisole 
• 86164-70-7 2-methyl-2-phenylmalononitrile 
• 50638-47-6 4-bromo-2-chloro-1-methoxybenzene 

Downstream Products

• 4394-54-1 1-(3'-chloro-4'-methoxyphenyl)-1-propanone 
• 102976-53-4 2-Bromo-1-(3-chloro-4-methoxy-phenyl)-propan-1-one 
• 189297-37-8 3-chloro-4-methoxy-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide 
• 168010-83-1 3-(2-chloro-6-fluorophenyl)-5-(3-chloro-4-methoxyphenyl)-1-methyl-1H-1,2,4-triazole 
• 41965-95-1 (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride 
• 2315-81-3 2-chloro-4-cyanophenol 
• 1409950-49-7 3-(3-chloro-4-methoxyphenyl)-6-methoxyisoquinolin-1-ol 
• 1409950-48-6 1-chloro-3-(3-chloro-4-methoxyphenyl)-6-methoxyisoquinoline 
• 1333152-96-7 C₉H₈ClN₃O 
• 1333151-61-3 (Z)-isopropyl 3-(3-(3-chloro-4-methoxyphenyl)-1H-1,2,4-triazol-1-yl)acrylate 
• 102151-35-9 3-chloro-4-methoxybenzimidine 
• 177661-55-1 1-[4-(methylsulfonyl)phenyl]-2-(4-methoxy-3-chlorophenyl)-4-trifluoromethyl-4-hydroxy-4,5-dihydro-1H-imidazole 
• 177661-25-5 1-[4-(methylsulfonyl)phenyl]-2-(4-methoxy-3-chlorophenyl)-4-trifluoromethyl-1H-imidazole 

Relevant articles and documents

The application of NCTS (N-cyano-N-phenyl-p-toluenesulfonamide) in palladium-catalyzed cyanation of arenediazonium tetrafluoroborates and aryl halides

Using NCTS (N-cyano-N-phenyl-p-toluenesulfonamide) as an electrophilic cyanation reagent, palladium-catalyzed cyanation of arenediazonium tetrafluoroborates and aryl halides was achieved under mild conditions. The method allowed the effective synthesis of various aryl nitriles in suitable yields via a coupling reaction.

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.

Room temperature C(sp2)-H oxidative chlorination: Via photoredox catalysis

Photoredox catalysis has been developed to achieve oxidative C-H chlorination of aromatic compounds using NaCl as the chlorine source and Na2S2O8 as the oxidant. The reactions occur at room temperature and exhibit exclusive selectivity for C(sp2)-H bonds over C(sp3)-H bonds. The method has been used for the chlorination of a diverse set of substrates, including the expedited synthesis of key intermediates to bioactive compounds and a drug.