4-(Acetoxymethyl)benzoic acid

Base Information

• Chemical Name: 4-(Acetoxymethyl)benzoic acid
• CAS No.: 15561-46-3
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID60427390
• Nikkaji Number: J26.902F
• Wikidata: Q82240049
• Mol file: 15561-46-3.mol

Synonyms:4-(Acetoxymethyl)benzoic acid;15561-46-3;4-ACETOXYMETHYLBENZOIC ACID;Ac-HMBA-Linker;4-(acetyloxymethyl)benzoic Acid;4-[(acetyloxy)methyl]benzoic acid;MFCD01090957;Benzoic acid,4-[(acetyloxy)methyl]-;Benzoic acid, 4-[(acetyloxy)methyl]-;4-(Acetoxymethyl)benzoicacid;4-Acetoxymethyl benzoic acid;4-acetyloxymethylbenzoic acid;SCHEMBL100476;4-ACETOXYMETHYLBENZOICACID;4-(acetyloxy-methyl)benzoic acid;DTXSID60427390;DLMONAQGOXNQGP-UHFFFAOYSA-N;4-[(acetyloxyl)methyl]benzoic acid;AC4525;AKOS001107167;NCGC00337848-01;BS-21550;SY017144;CS-0148557;FT-0692325;AB01330150-02;EN300-1191580;A883637;J-009211;Z54580268;VZQ

Chemical Property of 4-(Acetoxymethyl)benzoic acid

Chemical Property:

• Melting Point: 123-124 °C
• Boiling Point: 327.4 °C at 760 mmHg
• PKA: 4.14±0.10(Predicted)
• Flash Point: 129.6 °C
• PSA: 63.60000
• Density: 1.254 g/cm³
• LogP: 1.44790
• Storage Temp.: Store at RT.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 216

Purity/Quality:

99% ^*data from raw suppliers

4-Acetoxymethylbenzoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1=CC=C(C=C1)C(=O)O

Technology Process of 4-(Acetoxymethyl)benzoic acid

There total 17 articles about 4-(Acetoxymethyl)benzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

N-Acetylimidazole (2466-76-4) + 3-hydroxymethyl-benzoic acid (3006-96-0) → p-acetoxymethyl benzoic acid (15561-46-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 1h; chemoselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.202107438

Reference yield: 95.0%

acetic acid (64-19-7,77671-22-8) + p-Toluic acid (99-94-5) → terephthalic acid (100-21-0) + 3-hydroxymethyl-benzoic acid (3006-96-0) + p-acetoxymethyl benzoic acid (15561-46-3) + 4-Carboxybenzaldehyde (619-66-9)

Guidance literature:

With N-hydroxyphthalimide; air; cobalt(II) acetate; manganese(II) acetate; at 150 ℃; for 3h; under 22800 Torr;

DOI:10.1002/1615-4169(20010226)343:2<220::aid-adsc220>3.0.co;2-n

Reference yield: 95.0%

4-bromomethylbenzoic Acid (6232-88-8) + acetic acid (64-19-7,77671-22-8) → p-acetoxymethyl benzoic acid (15561-46-3)

Guidance literature:

With potassium acetate; for 8h; Heating;

upstream raw materials:

p-(chloromethyl)benzoyl chloride

sodium acetate

3-hydroxymethyl-benzoic acid

acetyl chloride

Downstream raw materials:

4-{[(2-fluoroethoxy)amino]carbonyl}benzyl acetate

(4-{[2-(3-nitro-4-phenylphenyl)ethyl]carbamoyl}phenyl)methyl acetate

4-acetoxymethyl-benzoyl chloride

3-hydroxymethyl-benzoic acid

Refernces

• 1、 Eaton, John K.,Kramm, Anneke,Ruberto, Richard A.,Schreiber, Stuart L.,Viswanathan, Vasanthi S.. "Diacylfuroxans Are Masked Nitrile Oxides That Inhibit GPX4 Covalently". supporting information. . Retrieved 2020/01/02.
• 2、 Yang, Xiu-Dong,Pan, Zhao-Xi,Li, Da-Jun,Wang, Guan,Liu, Min,Wu, Rong-Gui,Wu, Yan-Hua,Gao, Yong-Chen. "A Scalable Synthesis of Tofogliflozin Hydrate". . p. 1821 - 1827. Retrieved 2016/10/31.