95-03-4

Basic information

• Product Name: 5-Chloro-2-methoxyaniline
• Synonyms: 2-Amino-4-chioroanisole;5-chloro-2-methoxy-benzenamin;5-Chloro-2-methoxybenzenamine;P-CHLORO-O-AMINOANISOLE;2-AMINO-4-CHLOROANISOLE;2-METHOXY-5-CHLOROANILINE;AKOS BBS-00003626;5-Chloro-2-anisidine
• CAS NO: 95-03-4
• Molecular Formula: C₇H₈ClNO
• Molecular Weight: 157.6
• EINECS: 202-385-2
• Product Categories: Intermediates of Dyes and Pigments;Anilines, Aromatic Amines and Nitro Compounds;API Intermediate
• Mol File: 95-03-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 81-83 °C(lit.)
• Boiling Point: 135 °C (5.85078 mmHg)
• Flash Point: 136 °C
• Appearance: Off-white to tan crystalline powder or flakes
• Density: 1.1760 (rough estimate)
• Vapor Pressure: 0.013mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 3.48±0.10(Predicted)
• Stability: Light Sensitive
• BRN: 879161
• CAS DataBase Reference: 5-Chloro-2-methoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-methoxyaniline(95-03-4)
• EPA Substance Registry System: 5-Chloro-2-methoxyaniline(95-03-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37
• RIDADR: UN 2233 6.1/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 95-03-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to tan crystalline powder or flakes

Uses

5-Chloro-2-methoxybenzenamine is used in preparation of appetite-modulating molecules.

Preparation

4-Chloro-1-methoxy-2-nitrobenzene reduction.

Purification Methods

Purify the aniline by steam distillation and recrystallisation from H2O or 40% aqueous EtOH. The N-acetate forms needles from hot H2O with m 104o, the N-benzoyl derivative forms needles from aqueous EtOH with m 77-78o, and the picrate has m 194o(dec). [Raiford & Colbert J Am Chem Soc 48 2657 1926, Beilstein 13 IV 879.]

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

Upstream product

• 89-21-4 4-chloro-2-nitroanisole 
• 137-52-0 N-[2-methoxy-5-chlorophenyl]-3-hydroxy-2-naphthalene carboxamide 
• 60468-21-5 2-methoxy-4,5-dichloroaniline 
• 106-48-9 4-chloro-phenol 
• 89-61-2 2,5-dichloronitrobenzene 
• 623-12-1 4-chloromethoxybenzene 
• 553-82-2 1,3-dichloro-4-methoxybenzene 
• 7664-41-7 ammonia 
• 71-43-2 benzene 
• 64-17-5 ethanol 
• 108-95-2 phenol 
• 137345-97-2 2-azido-4-chloro-1-methoxybenzene 
• 90-04-0 2-methoxy-phenylamine 

Downstream Products

• 22521-37-5 N-acetyl-5-chloro-4-nitro-2-anisidine 
• 52793-11-0 acetoacetic acid-(5-chloro-2-methoxy-anilide) 
• 35588-41-1 2-chloro-N-(5-chloro-2-methoxyphenyl)acetamide 
• 104665-77-2 N'-<5-Chlor-2-methoxy-phenyl>-N,N-dimethyl-1,3-diamino-propan 
• 54300-74-2 2,3,4-trichloro-6-methoxyaniline 
• 860586-90-9 2,4-dibromo-3-chloro-6-methoxyaniline 
• 386718-09-8 (5-Chloro-2-methoxy-phenyl)-[1-(4-trifluoromethyl-phenyl)-meth-(E)-ylidene]-amine 
• 202822-34-2 N-(5-chloro-2-methoxyphenyl)-3,5-bis(trifluoromethyl)benzamide 
• 948670-77-7 N-(5-chloro-2-methoxy-phenyl)-2-trifluoromethyl-benzamide 
• 63980-69-8 (2-methoxy-5-chlorophenyl)-2-thiourea 
• 384374-77-0 C₁₉H₁₅ClN₂O₄ 
• 1015136-99-8 C₁₄H₁₂ClN₃O 
• 1133824-18-6 C₁₈H₁₅ClN₂O₃ 
• 1189582-52-2 tert-butyl 1-{2-[(5-chloro-2-methoxyphenyl)amino]-2-oxoethyl}-3-(trifluoromethyl)-1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate 

Relevant articles and documents

Utilization of a Hydrogen Source from Renewable Lignocellulosic Biomass for Hydrogenation of Nitroarenes

Exploring of hydrogen source from renewable biomass, such as glucose in alkaline solution, for hydrogenation reactions had been studied since 1860s. According to proposed pathway, only small part of hydrogen source in glucose was utilized. Herein, the utilization of a hydrogen source from renewable lignocellulosic biomass, one of the most abundant renewable sources in nature, for a hydrogenation reaction is described. The hydrogenation is demonstrated by reduction of nitroarenes to arylamines in up to 95 % yields. Mechanism studies suggest that the hydrogenation occurs via a hydrogen transformation pathway.

Highly selective transfer hydrogenation of functionalised nitroarenes using cobalt-based nanocatalysts

Anilines are important feedstock for the synthesis of a variety of chemicals such as dyes, pigments, pharmaceuticals and agrochemicals. The chemoselective catalytic reduction of nitro compounds represents the most important and prevalent process for the manufacture of functionalized anilines. Consequently, the development of selective catalysts for the reduction of nitro compounds in the presence of other reducible groups is a major challenge and is crucial. In this regard, herein we show that the cobalt oxide (Co3O4-NGr@C) based nano-materials, prepared by the pyrolysis of cobalt-phenanthroline complexes on carbon constitute highly selective catalysts for the transfer hydrogenation of nitroarenes to anilines using formic acid as a hydrogen source. Applying these catalysts, a series of structurally diverse and functionalized nitroarenes have been reduced to anilines with unprecedented chemo-selectivity tolerating halides, olefins, aldehyde, ketone, ester, amide and nitrile functionalities.

A new class of heterogeneous platinum catalysts for the chemoselective hydrogenation of nitroarenes

A new series of nanostructured platinum catalysts able to catalyze the selective reduction of nitroarenes has been developed. The materials, made of organosilica physically doped with nanostructured platinum(0), are stable and efficient. Reactions in general proceed with high yield and often go to completion, while the catalysts can be reused in further reaction runs. This establishes a new class of relevant solid catalysts for synthetic organic chemistry named SiliaCat Platinum-Hydrogel.