7149-79-3

Basic information

• Product Name: 3-CHLORO-4-METHYLACETANILIDE
• Synonyms: 3’-chloro-p-acetotoluidid;3’-chloro-p-acetotoluidide;n-(3-chloro-4-methylphenyl)-acetamid;N1-(3-CHLORO-4-METHYLPHENYL)ACETAMIDE;3-CHLORO-4-METHYLACETANILIDE;N-(3-chloro-4-methylphenyl)acetamide;3-Chloro-4-methylacetanilide, 95+%;3-CHLOROPARAACETOTOLUIDIDE
• CAS NO: 7149-79-3
• Molecular Formula: C₉H₁₀ClNO
• Molecular Weight: 183.63
• EINECS: 230-483-5
• Mol File: 7149-79-3.mol
• Article Data: 22

Chemical Properties

• Melting Point: 105-107°C
• Boiling Point: 80°C (rough estimate)
• Flash Point: 155.4°C
• Appearance: /
• Density: 1.218
• Vapor Pressure: 0.000138mmHg at 25°C
• Refractive Index: 1.5330 (estimate)
• PKA: 14.46±0.70(Predicted)
• CAS DataBase Reference: 3-CHLORO-4-METHYLACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-METHYLACETANILIDE(7149-79-3)
• EPA Substance Registry System: 3-CHLORO-4-METHYLACETANILIDE(7149-79-3)

Safety Data

• Statements: 25
• Safety Statements: 20-36-45-60
• RIDADR: 2811
• RTECS: AN3325000
• TSCA: Yes
• PackingGroup: III
• Hazardous Substances Data: 7149-79-3(Hazardous Substances Data)

Usage

General Description

3-Chloro-4-methylacetanilide is an organic compound with molecular formula C9H10ClNO. This chemical belongs to the family of acetanilides, which are amides derived from acetic acid and anilines. Characterized by a faint, acrid odor, 3-Chloro-4-methylacetanilide is most commonly used in the industry of chemistry research as a reagent, reference standard, or building block in the synthesis of more complex compounds. It is recommended to handle this compound with proper protective gear due to potential health risks. Its physical properties include a solid form at room temperature, and it is generally white to light yellow in color. Being hazardous in nature, it should be carefully stored and disposed of in compliance with local regulations and environmental safety standards. It is not widely studied, missing from much regulatory database and thus not much is known about its toxicity or environmental impact.

InChI:InChI=1/C9H10ClNO/c1-6-3-4-8(5-9(6)10)11-7(2)12/h3-5H,1-2H3,(H,11,12)

Upstream product

• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 95-74-9 3-chloro-p-toluidine 
• 71-55-6 1,1,1-trichloroethane 
• 103-89-9 4-Methylacetanilide 
• 98-09-9 benzenesulfonyl chloride 
• 75-05-8 acetonitrile 
• 1338235-62-3 C₉H₇Cl 
• 99-99-0 1-methyl-4-nitrobenzene 
• 95-49-8 2-methylchlorobenzene 
• 121-86-8 2-chloro-4-nitrotoluene 
• 10387-40-3 potassium thioacetate 
• 7647-01-0 hydrogenchloride 
• 75-36-5 acetyl chloride 

Downstream Products

• 861611-40-7 acetic acid-(5-chloro-2-chloroacetyl-4-methyl-anilide) 
• 7149-78-2 5-chloro-4-methyl-2-nitroacetanilide 
• 439096-91-0 acetic acid-(3-chloro-4-methyl-2,6-dinitro-anilide) 
• 89640-05-1 3-chloro-4-methyl-2,6-dinitro-aniline 
• 179474-81-8 prucalopride 
• 5460-34-4 7-methyl-8-chloro-10-(1'-D-ribityl)isoalloxazine 
• 1207984-88-0 tert-butyl benzyl(2-(8-(cyclopentyloxy)-7-methyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethyl)carbamate 
• 1207984-86-8 tert-butyl benzyl(2-(8-chloro-7-methyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethyl)carbamate 
• 1207984-80-2 10-(2-(benzylamino)ethyl)-8-chloro-7-methylbenzo[g]pteridine-2,4(3H,10H)-dione 
• 1207985-37-2 tert-butyl 7-[(5-cyclopropyl-4-methyl-2-nitrophenyl)amino]heptanoate 
• 1207985-38-3 tert-butyl 7-[(2-amino-5-cyclopropyl-4-methylphenyl)amino]heptanoate 
• 1207984-52-8 ethyl 7-[(5-cyclopropyl-4-methyl-2-nitrophenyl)amino]heptanoate 
• 1207983-92-3 tert-butyl 7-[(5-chloro-4-methyl-2-nitrophenyl)amino]heptanoate 
• 1207984-53-9 ethyl 7-[(2-amino-5-cyclopropyl-4-methylphenyl)amino]heptanoate 

Relevant articles and documents

Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.

Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation

Under superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation of arenes is complementary to existing methods and can be applied, through protection by protonation, to the late-stage site-selective functionalization of natural alkaloids and active pharmaceutical ingredients.

Method for preparing prucalopride

The invention provides a method for preparing prucalopride. The method comprises the following steps: taking 3-chloro-4-methylaniline as an initial raw material, performing amino protection, nucleophilic substitution, hydroxy protection, aromatic hydrocarbon chlorination, free radical bromination, hydrolysis, molecular Friedel-Crafts alkylation reaction ring closure, amino deprotection and oxidative amidation, thereby obtaining the prucalopride. According to the scheme, a dangerous process is not adopted, any highly toxic reagent is not used, the method is safe, green and environmental-friendly, the amount of by-products produced in the reaction is small, and the yield is improved.