5663-71-8

Basic information

• Product Name: 2-(aminocarbonyl)phenyl acetate
• Synonyms: 2-(aminocarbonyl)phenyl acetate;2-Acetoxybenzamide;Benzamide, 2-(acetyloxy)- (9ci);Brn 2692708;Einecs 227-120-8;Influina;o-Acetyl salicylamide;Salicylamide, acetate (ester) (8ci)
• CAS NO: 5663-71-8
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.17266
• EINECS: 227-120-8
• Mol File: 5663-71-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 138 °C
• Boiling Point: 323.4°Cat760mmHg
• Flash Point: 171.8°C
• Appearance: /
• Density: 1.229g/cm³
• Vapor Pressure: 0.000262mmHg at 25°C
• Refractive Index: 1.551
• PKA: 15.48±0.50(Predicted)
• CAS DataBase Reference: 2-(aminocarbonyl)phenyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(aminocarbonyl)phenyl acetate(5663-71-8)
• EPA Substance Registry System: 2-(aminocarbonyl)phenyl acetate(5663-71-8)

Safety Data

• Hazardous Substances Data: 5663-71-8(Hazardous Substances Data)

Usage

Type of compound

Acetate ester A class of organic compounds characterized by the presence of an ester functional group formed by the bonding of an acetic acid molecule with an alcohol.

Aminocarbonyl group

NH2-COA functional group consisting of an amine (NH2) and a carbonyl (CO) group, which is attached to the phenyl ring in 2-(aminocarbonyl)phenyl acetate.

Phenyl ring

C6H5 A benzene ring with one hydrogen atom replaced by the aminocarbonyl group, resulting in a phenyl ring structure.

Usage in synthesis

Pharmaceutical, agrochemical, and organic compounds 2-(aminocarbonyl)phenyl acetate is commonly used as a starting material or intermediate in the synthesis of various chemical products, including pharmaceuticals and agrochemicals.

Building block

Organic chemistry reactions The compound serves as a versatile building block in organic chemistry, allowing for the construction of more complex molecules through various chemical reactions.

Versatility

Chemical industry applications 2-(aminocarbonyl)phenyl acetate has a wide range of applications in the chemical industry, making it a valuable and useful compound for various purposes.

InChI:InChI=1/C9H9NO3/c1-6(11)13-8-5-3-2-4-7(8)9(10)12/h2-5H,1H3,(H2,10,12)

Upstream product

• 110-86-1 pyridine 
• 75-36-5 acetyl chloride 
• 65-45-2 salicylamide 
• 108-24-7 acetic anhydride 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 60-29-7 diethyl ether 
• 7664-41-7 ammonia 
• 36335-42-9 (2-acetoxy-benzoyl)-carbonic acid ethyl ester 
• 50-78-2 aspirin 
• 119-36-8 methyl salicylate 

Downstream Products

• 132305-18-1 acetyl-(2-benzoyloxy-benzoyl)-amine 
• 487-48-9 salacetamide 
• 65-45-2 salicylamide 
• 56429-73-3 2-hydroxy-N-pentanoylbenzamide 
• 1093612-66-8 5-acetylsalicyloyl-1,3,5-dithiazinane 
• 118134-04-6 dimethyl 3-(o-acetoxyphenyl)isothiazole-4,5-dicarboxylate 
• 118134-17-1 ethyl 3-(o-acetoxyphenyl)isothiazole-5-carboxylate 
• 77718-64-0 3N-acetamido-4-hydroxybenzenesulfonyl chloride 
• 51051-49-1 N,O-diacetylsalicylamide 
• 64-19-7 acetic acid 
• 52059-60-6 5-(o-acetoxyphenyl)-1,3,4-oxathiazol-2-one 
• 76159-05-2 2-acetoxy-benzoic acid-(2,2,2-trichloro-1-hydroxy-ethylamide) 
• 116704-43-9 anhydroacetylsalicylamide 
• 40187-51-7 5-acetylsalicylamide 

Relevant articles and documents

Asymmetric Hydrogenation of Cationic Intermediates for the Synthesis of Chiral N,O-Acetals

For over half a century, transition-metal-catalyzed homogeneous hydrogenation has been mainly focused on neutral and readily prepared unsaturated substrates. Although the addition of molecular hydrogen to C=C, C=N, and C=O bonds represents a well-studied paradigm, the asymmetric hydrogenation of cationic species remains an underdeveloped area. In this study, we were seeking a breakthrough in asymmetric hydrogenation, with cationic intermediates as targets, and thereby anticipating applying this powerful tool to the construction of challenging chiral molecules. Under acidic conditions, both N- or O-acetylsalicylamides underwent cyclization to generate cationic intermediates, which were subsequently reduced by an iridium or rhodium hydride complex. The resulting N,O-acetals were synthesized with remarkably high enantioselectivity. This catalytic strategy exhibited high efficiency (turnover number of up to 4400) and high chemoselectivity. Mechanistic studies supported the hypothesis that a cationic intermediate was formed in situ and hydrogenated afterwards. A catalytic cycle has been proposed with hydride transfer from the iridium complex to the cationic sp2 carbon atom being the rate-determining step. A steric map of the catalyst has been created to illustrate the chiral environment, and a quantitative structure–selectivity relationship analysis showed how enantiomeric induction was achieved in this chemical transformation.

Convenient preparation of primary amides via activation of carboxylic acids with ethyl chloroformate and triethylamine under mild conditions

Primary amides were easily prepared in 22-99% yields from the corresponding carboxylic acids 1 or 5 with NH4Cl via activation with ClCO 2Et and Et3N. The enantiomers of the corresponding primary amides of Cbz-, Boc-, or Fmoc-α-amino acids can be separated by using a chiral column.

Synthesis and Reaction of 2-Substituted 4H-1,3-Benzoxazin-4-ones

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