42469-26-1

Basic information

• Product Name: N-(2-hydroxyethyl)-4-methylbenzamide
• Synonyms: N-(2-hydroxyethyl)-4-methylbenzamide;IDI1_016251;Maybridge3_004864;ZINC03138367
• CAS NO: 42469-26-1
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.21572
• Mol File: 42469-26-1.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(2-hydroxyethyl)-4-methylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-hydroxyethyl)-4-methylbenzamide(42469-26-1)
• EPA Substance Registry System: N-(2-hydroxyethyl)-4-methylbenzamide(42469-26-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 42469-26-1(Hazardous Substances Data)

Upstream product

• 141-43-5 ethanolamine 
• 99-94-5 p-Toluic acid 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 874-60-2 4-methyl-benzoyl chloride 
• 619-55-6 para-methylbenzamide 
• 1644630-66-9 C₁₄H₁₀ClNO₄ 

Downstream Products

• 10200-70-1 2-(4-methylphenyl)-4,5-dihydro-1,3-oxazole 
• 161194-79-2 N-(2-chloroethyl)-4-methylbenzamide 
• 27115-50-0 N-(4-methylbenzoyl)glycine 

Relevant articles and documents

Metal-Free O-Selective Direct Acylation of Amino Alcohols Through Pseudo-Intramolecular Process

Efficient α-aryl-β-keto ester acylation of amine accompanied by the elimination of ethyl phenylacetate was achieved owing to the pseudo-intramolecular process. The eliminated ethyl phenylacetate could be recycled by conversion into an α-aryl-β-keto ester upon treatment with an acyl chloride in the presence of lithium bis(trimethylsilyl)amide, by which the atom economy considerably increased. Acylation using an α-aryl-β-keto ester is highly sensitive to the bulkiness of the nucleophile, which facilitated the regioselective-acylation of the less hindered amino group in diamine without protecting the other. The transacylation of α-aryl-β-keto ester with N-alkylamino alcohol resulted in chemoselective O-acylation without protecting the amino group because the hydroxy group was attracted to the reaction site of the keto ester by forming an ammonium salt. Transacylation was demonstrated to be a practically useful tool for organic synthesis because this protocol can be conducted under mild conditions with simple manipulations in the absence of any additives such as metal catalyst and base.

Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines

The first general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3. Trimethylsilyl polyphosphate in solvent-free conditions allowed for the synthesis of hitherto-unreported 4,5,6,7-tetrahydro-1,3-oxazepines. The method involves good to excellent yields and short reaction times.The reaction mechanism and the role of PPA esters were investigated in a chiral substrate.

Hydrogen bond organocatalysis of benzotriazole in transamidation of carboxamides with amines

A new method of transamidation of carboxamides with amines catalyzed by benzotriazole has been developed.