127292-04-0

Basic information

• Product Name: 4-chloro-N-(3,5-dimethylphenyl)benzamide
• Synonyms: 4-chloro-N-(3,5-dimethylphenyl)benzamide
• CAS NO: 127292-04-0
• Molecular Formula: C₁₅H₁₄ClNO
• Molecular Weight: 259.73076
• Mol File: 127292-04-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-chloro-N-(3,5-dimethylphenyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-N-(3,5-dimethylphenyl)benzamide(127292-04-0)
• EPA Substance Registry System: 4-chloro-N-(3,5-dimethylphenyl)benzamide(127292-04-0)

Safety Data

• Hazardous Substances Data: 127292-04-0(Hazardous Substances Data)

Upstream product

• 203321-89-5 (3,5-dimethylphenyl)carbamic acid 1,1-dimethylethyl ester 
• 54132-75-1 3,5-dimethylphenyl isocyanate 
• 7519-91-7 tris(4-chlorophenyl)boroxine 
• 1679-18-1 4-Chlorophenylboronic acid 
• 373384-13-5 2-(4-chlorophenyl)-1,3,2-dioxaborinane 
• 122-01-0 4-chloro-benzoyl chloride 
• 108-69-0 3,5-dimethylaminoaniline 

Relevant articles and documents

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.

Copper(i)-catalyzed amidation reaction of organoboronic esters and isocyanates

A simple and efficient methodology for the preparation of amides from easily available organoboronic esters and isocyanates has been accomplished using a ligand-free copper(i) catalyst. The reaction system demonstrated a broad substrate scope and provided convenient access to a wide variety of secondary amides.

Anticonvulsant activity of some 4-methoxy- and 4-chlorobenzanilides

A series of mono-, di-, and trimethylated derivatives of 4-chloro- and 4-methoxybenzanilide was synthesized and evaluated for anticonvulsant activity. This series was prepared in the course of studies designed to examine the relationship between anticonvulsant effects and benzamide structure. The compounds were tested in mice against seizures induced by maximal electroshock (MES) and pentylenetetrazole (scMet), as well as with the rotorod assay for neurologic deficit. In mice dosed intraperitoneally, 4-methoxy-2, 6-dimethylbenzanilide (4) showed a median anticonvulsant potency (ED50) of 18.58 mg/kg in the MES test and a median toxicity (TD50) of 133.72 mg/kg in the rotorod toxicity assay, yielding a protective index (PI = TD50/ED50) of 7.2. In mice dosed orally with 4, the anti-MES ED50 was 27.40 mg/kg and the TD50 dose was determined to be 342.58 mg/kg, resulting in a protective index of 12.5.