2-Acetoxybenzoyl chloride

Base Information

• Chemical Name: 2-Acetoxybenzoyl chloride
• CAS No.: 5538-51-2
• Molecular Formula: C9H7ClO3
• Molecular Weight: 198.606
• Hs Code.: 29163900
• European Community (EC) Number: 226-899-1
• NSC Number: 97216
• UNII: 67R3L2L9J7
• DSSTox Substance ID: DTXSID10203924
• Nikkaji Number: J210.584E
• Wikidata: Q72434292
• Mol file: 5538-51-2.mol

Synonyms:2-Acetoxybenzoyl chloride;5538-51-2;o-Acetylsalicyloyl chloride;2-(Chlorocarbonyl)phenyl acetate;Acetylsalicyloyl chloride;(2-carbonochloridoylphenyl) acetate;Benzoyl chloride, 2-(acetyloxy)-;Acetylsalicoyl chloride;67R3L2L9J7;EINECS 226-899-1;NSC 97216;NSC-97216;o-Acetylsalicyloylchloride;Aspirin chloride;O-Acetylsalicylryl chloride;ASCC;acetylsalicylic chloride;o-acetoxybenzoylchloride;acetylsalicylsaurechlorid;2-acetoxybenzoylchloride;o-Acetoxybenzoyl chloride;o-Acetylsalicoyl chloride;acetyl salicyloyl chloride;Acetyl-salicyloyl chloride;2-acetoxy benzoyl chloride;acetylsalicylic acid chloride;acetyl salicylic acid chloride;2-(Acetyloxy)benzoyl chloride;SCHEMBL133699;UNII-67R3L2L9J7;2-acetoxybenzoic acid chloride;acetyl salicyclic acid chloride;ACETYLSALICYCLOYL CHLORIDE;DTXSID10203924;2-(chlorocarbonyl)-phenyl acetate;O-Acetylsalicyloyl chloride, 95%;2-(Chlorocarbonyl)phenyl acetate #;AMY15535;NSC97216;MFCD00000663;AKOS000276274;BS-44104;A8139;FT-0635765;D88484;W-105567

Chemical Property of 2-Acetoxybenzoyl chloride

Chemical Property:

• Appearance/Colour: yellow to light orange chunks
• Vapor Pressure: 6.01E-05mmHg at 25°C
• Melting Point: 45-49 °C(lit.)
• Refractive Index: n20/D 1.536(lit.)
• Boiling Point: 345.8 °C at 760 mmHg
• Flash Point: 126.6 °C
• PSA: 43.37000
• Density: 1.294 g/cm³
• LogP: 1.99090
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Water Solubility.: Soluble in toluene. Reacts with water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 198.0083718
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

99.9% ^*data from raw suppliers

O-Acetylsalicyloyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C,Xi
• Statements: 22-34-37-29
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CC=CC=C1C(=O)Cl
• Uses: O-Acetylsalicyloyl chloride was used in the synthesis of enantiomerically pure bidentate heteroorganic ligands built on simple achiral skeletons and containing an aziridine moiety. It was used in the general synthesis of acetoxybenzamides. It was used in the chemical synthesis of 2,2,6,6-tetramethyl-1-piperidinyloxy(TEMPO)-aspirin conjugate via condensation reaction with 4-hydroxy-TEMPO. It was used as reagent in acylation of cyclobutenediones.

Technology Process of 2-Acetoxybenzoyl chloride

There total 7 articles about 2-Acetoxybenzoyl chloride 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:

oxalyl dichloride (79-37-8) + aspirin (50-78-2,98201-60-6) → O-acetylsalicyloyl chloride (5538-51-2)

Guidance literature:

With N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1080/10426507.2011.562398

Reference yield:

salicylic acid (69-72-7,25496-36-0,8052-31-1) → O-acetylsalicyloyl chloride (5538-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 0.5 h / 25 °C

2: oxalyl dichloride / dichloromethane / 3 h / 20 °C

With pyridine; oxalyl dichloride; In dichloromethane;

DOI:10.1016/j.bmc.2012.04.033

Reference yield:

2-Methoxybenzoic acid (579-75-9) → O-acetylsalicyloyl chloride (5538-51-2)

Guidance literature:

With thionyl chloride; In benzene; for 1h; Heating;

DOI:10.1016/0040-4020(89)80142-5

upstream raw materials:

2-Methoxybenzoic acid

phosphorus pentachloride

aspirin

sodium O-acetylsalicylate

Downstream raw materials:

N-(2-hydroxyethyl)salicylamide

2-(phenylcarbamoyl)phenyl acetate

ortho-urahydroxy benzoic acid

4-(2-acetoxy-benzoylamino)-benzoic acid ethyl ester

Refernces

• 1、 Eissa, Ibrahim H.,Mohammad, Haroon,Qassem, Omar A.,Younis, Waleed,Abdelghany, Tamer M.,Elshafeey, Ahmed,Abd Rabo Moustafa, Mahmoud M.,Seleem, Mohamed N.,Mayhoub, Abdelrahman S.. "Diphenylurea derivatives for combating methicillin- and vancomycin-resistant Staphylococcus aureus". . p. 73 - 85. Retrieved 2017/03/02.
• 2、 Ngaini, Zainab,Mohd Arif, Maya Asyikin,Hussain, Hasnain,Mei, Er Su,Tang, Donna,Kamaluddin, Dyg Halimatulzahrah Abang. "Synthesis and antibacterial activity of acetoxybenzoyl thioureas with aryl and amino acid side Chains". experimental part. p. 1 - 7. Retrieved 2012/03/27.