15561-46-3

Basic information

• Product Name: 4-ACETOXYMETHYLBENZOIC ACID
• Synonyms: AC-HMBA LINKER;4-ACETOXYMETHYLBENZOIC ACID;4-[(Acetyloxy)methyl]benzoic acid
• CAS NO: 15561-46-3
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• Mol File: 15561-46-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 123-124 °C
• Boiling Point: 327.4 °C at 760 mmHg
• Flash Point: 129.6 °C
• Appearance: /
• Density: 1.254 g/cm³
• Storage Temp.: Store at RT.
• PKA: 4.14±0.10(Predicted)
• CAS DataBase Reference: 4-ACETOXYMETHYLBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETOXYMETHYLBENZOIC ACID(15561-46-3)
• EPA Substance Registry System: 4-ACETOXYMETHYLBENZOIC ACID(15561-46-3)

Safety Data

• Hazardous Substances Data: 15561-46-3(Hazardous Substances Data)

Usage

General Description

4-ACETOXYMETHYLBENZOIC ACID, also known as AMBA, is a chemical compound with the molecular formula C10H10O4. It is a derivative of benzoic acid with a methoxy group and an acetyl group attached to the benzene ring. AMBA is often used as a precursor in organic synthesis, particularly in the production of pharmaceuticals and other fine chemicals. It is also commonly used in the synthesis of liquid crystals and other advanced materials. AMBA is known to have anti-inflammatory and analgesic properties and has been studied for its potential pharmacological applications. Additionally, it is utilized as an intermediate in the synthesis of other chemicals, making it a versatile and important compound in the field of organic chemistry.

Upstream product

• 99-94-5 p-Toluic acid 
• 76-05-1 trifluoroacetic acid 
• 2466-76-4 N-Acetylimidazole 
• 3006-96-0 3-hydroxymethyl-benzoic acid 
• 6232-88-8 4-bromomethylbenzoic Acid 
• 127-09-3 sodium acetate 
• 75-05-8 acetonitrile 
• 108-24-7 acetic anhydride 
• 874-60-2 4-methyl-benzoyl chloride 
• 2216-45-7 p-methylbenzyl alcohol acetate 
• 106-42-3 para-xylene 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 876-08-4 p-(chloromethyl)benzoyl chloride 

Downstream Products

• 1017599-23-3 4-{[(2-fluoroethoxy)amino]carbonyl}benzyl acetate 
• 1254103-23-5 (4-{[2-(3-nitro-4-phenylphenyl)ethyl]carbamoyl}phenyl)methyl acetate 
• 78616-33-8 4-acetoxymethyl-benzoyl chloride 
• 3006-96-0 3-hydroxymethyl-benzoic acid 

Relevant articles and documents

Practical Chemoselective Acylation: Organocatalytic Chemodivergent Esterification and Amidation of Amino Alcohols with N-Carbonylimidazoles

Chemoselective transformations are a cornerstone of efficient organic synthesis; however, achieving this goal for even simple transformations, such as acylation reactions, is often a challenge. We report that N-carbonylimidazoles enable catalytic chemodivergent aniline or alcohol acylation in the presence of pyridinium ions or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), respectively. Both acylation reactions display high and broad chemoselectivity for the target group. Unprecedented levels of chemoselectivity were observed in the DBU-catalyzed esterification: A single esterification product was obtained from a molecule containing primary aniline, alcohol, phenol, secondary amide, and N?H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation of the acylimidazole electrophile.

Preparation method of Tofogliflozin monohydrate

The invention relates to a preparation method of Tofogliflozin monohydrate. In the route, p-Hydroxybenzoic acid used as a starting material is subjected to acylation, iodination, Friedel-Crafts and reduction reaction to obtain an iodinated diphenylmethane framework; by means of the characteristic that an iodinated substance is reactive, the splicing the diphenylmethane framework and a saccharide ring is realized under mild conditions through the effect of isopropyl magnesium chloride lithium chloride; and the eleven-step total yield is 22%. The route is high in yield, favorable in selectivity, low in production cost and mild in reaction conditions, does not use flammable, explosive or high-toxicity reagent, obtains products and intermediate compounds which are easy to purify, and is suitable for industrial production.

A lewis acid-promoted pinner reaction

Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward synthesis of acrylates and benzoates starting with acrylonitrile and benzonitrile, respectively, is similarly possible. Phenols are not acylated under these reaction conditions. The method has been used for the first total synthesis of the natural product monaspilosin. In the reaction of benzyl alcohols variable amounts of amides are formed in a Ritter-type side reaction.