13726-14-2

Basic information

• Product Name: 4-Chloro-3-methoxyaniline
• Synonyms: 2-CHLORO-5-AMINOANISOLE;4-CHLORO-3-METHOXYANILINE;4-CHLORO-M-ANISIDINE;5-Amino-2-chloroanisole;3-Methoxy-4-chloroaniline;4-Chloro-m-anisidine 5-Amino-2-chloroanisole 2-Chloro-5-aminoanisole;5-Amino-2-chloroanisole, 4-Chloro-m-anisidine;5-AMino-2-chloroanisole[4-Chloro-3-Methoxyaniline]
• CAS NO: 13726-14-2
• Molecular Formula: C₇H₈ClNO
• Molecular Weight: 157.6
• Product Categories: Amines;blocks;Anilines, Aromatic Amines and Nitro Compounds;Anilines, Amides & Amines;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds
• Mol File: 13726-14-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 77-79
• Boiling Point: 274.058 °C at 760 mmHg
• Flash Point: 119.546 °C
• Appearance: /
• Density: 1.234 g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.54±0.10(Predicted)
• CAS DataBase Reference: 4-Chloro-3-methoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-methoxyaniline(13726-14-2)
• EPA Substance Registry System: 4-Chloro-3-methoxyaniline(13726-14-2)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-36/37
• RIDADR: UN2233
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 13726-14-2(Hazardous Substances Data)

Usage

Uses

4-Chloro-3-methoxyaniline is a useful reagent for the preparation of Raf kinase inhibitors.

InChI:InChI=1/C7H8ClNO/c1-10-7-4-5(9)2-3-6(7)8/h2-4H,9H2,1H3

Upstream product

• 1009-36-5 2-chloro-5-nitroanisole 
• 1984-58-3 2,5-dichloroanisole 
• 7664-41-7 ammonia 
• 553-82-2 1,3-dichloro-4-methoxybenzene 
• 97-52-9 2-methoxy-4-nitrophenylamine 
• 49735-71-9 2-methoxy-4-nitrobenzene diazonium 1,5-naphthalene disulfonate 
• 7439-89-6 iron 
• 1236162-19-8 C₇H₇ClINO 
• 16817-43-9 5-Bromo-2-chloroanisole 

Downstream Products

• 102236-59-9 4-chloro-3-methoxy-N,N-dimethyl-aniline 
• 120222-86-8 4-chloro-3-methoxy-phenyl isothiocyanate 
• 18113-07-0 4-Chloro-3-methoxyphenol 
• 43096-00-0 N-[4-(4-Chloro-3-methoxy-phenylamino)-9,10-dioxo-9,10-dihydro-anthracen-1-yl]-benzamide 
• 86726-32-1 2-Chloro-3-(4-chloro-3-methoxy-phenyl)-propionic acid methyl ester 
• 13726-16-4 4-chloro-3-methoxybenzaldehyde 
• 16817-43-9 5-Bromo-2-chloroanisole 
• 103209-95-6 4-(5-chloro-6-methoxy-benzotriazol-2-yl)-stilbene-2-sulfonic acid dibutylamide 
• 334710-28-0 (4-chloro-3-methoxy-phenyl)-carbamic acid tert-butyl ester 
• 28170-67-4 N-(4-chloro-3-methoxyphenyl)-N,N'-dimethylurea 
• 161949-50-4 1-chloro-4-iodo-2-methoxybenzene 
• 65105-52-4 methyl (2E,3Z,5E)-6-(4-chloro-3-methoxyphenyl)-2-methoxymethylidene-3-methylhexa-3,5-dienoate 
• 334710-35-9 1-(6-amino-3-chloro-2-methoxy-phenyl)-2,2,2-trifluoro-ethanone 
• 334710-31-5 [4-Chloro-3-methoxy-2-(2,2,2-trifluoro-acetyl)-phenyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

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AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.