3,4-Diacetoxybenzoic acid

Base Information

• Chemical Name: 3,4-Diacetoxybenzoic acid
• CAS No.: 58534-64-8
• Molecular Formula: C11H10 O6
• Molecular Weight: 238.197
• Hs Code.: 2918990090
• European Community (EC) Number: 261-312-2
• DSSTox Substance ID: DTXSID00207254
• Nikkaji Number: J296.968H
• Wikidata: Q83081146
• ChEMBL ID: CHEMBL1609115
• Mol file: 58534-64-8.mol

Synonyms:tachistin

Chemical Property of 3,4-Diacetoxybenzoic acid

Chemical Property:

• Vapor Pressure: 3.02E-07mmHg at 25°C
• Boiling Point: 403.8°Cat760mmHg
• Flash Point: 158.4°C
• PSA: 77.76000
• Density: 1.344g/cm³
• LogP: 0.79600
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO, Ethyl Acetate, Methanol
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 238.04773803
• Heavy Atom Count: 17
• Complexity: 324

Purity/Quality:

98.5% ^*data from raw suppliers

ProtocatechuicAcidDiacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=C(C=C(C=C1)C(=O)O)OC(=O)C
• Uses: Protocatechuic Acid Diacetate is an intermediate in the synthesis of Roflumilast (R639700), an selective phosphodiesterase 4(PDE4) inhibitor.

Technology Process of 3,4-Diacetoxybenzoic acid

There total 19 articles about 3,4-Diacetoxybenzoic 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: 95.0%

3,4-Dihydroxybenzoic acid (99-50-3) + acetic anhydride (108-24-7) → 3,4-Diacetoxy-benzoesaeure (58534-64-8)

Guidance literature:

With pyridine; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2012.03.100

Reference yield: 56.0%

acetic anhydride (108-24-7) + 3',4',7-trihydroxyflavylium chloride (18393-49-2) → 2,4-bis(acetyloxy)benzoic acid (51-01-4) + 3,4-Diacetoxy-benzoesaeure (58534-64-8)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; 1) 5 h, room temp., pyridine; 2) acetic ester, water, 20 min : decomposition reaction;

Reference yield: 56.0%

acetic anhydride (108-24-7) + 3',4'-dihydroxy-7-dimethoxyflavylium chloride (89475-36-5) → 3,4-Diacetoxy-benzoesaeure (58534-64-8) + 2-acetoxy-4-methoxybenzoic acid (17336-11-7)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; 1) 5 h, room temp., pyridine; 2) acetic ester, water, 20 min : decomposition reaction;

upstream raw materials:

3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one

3,4-Dihydroxybenzoic acid

acetic anhydride

2-Methoxymethoxy-4-((E)-propenyl)-phenol

Downstream raw materials:

Veratric acid

3,4-diacetoxy-benzoic acid 3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)-(4-hydroxy-phenyl)-methyl]-2-oxo-2H-chromen-4-yl ester

4-(3,4-diacetoxybenzoyloxy)benzaldehyde

ferutinianin

Refernces

• 1、 Lü, Zirui,Li, Xiaona,Li, Kebin,Wang, Cong,Du, Tingting,Huang, Wei,Ji, Ming,Li, Changhong,Xu, Fengrong,Xu, Ping,Niu, Yan. "Structure-Activity Study of Nitazoxanide Derivatives as Novel STAT3 Pathway Inhibitors". supporting information. p. 696 - 703. Retrieved 2021/05/04.
• 2、 -. "COMPOUND HAVING EFFECT OF INHIBITING PLATELET AGGREGATION AND SALT THEREOF, AND COMPOSITION FOR PREVENTING OR TREATING THROMBOTIC DISEASES, CONTAINING SAME". Paragraph 0034. . Retrieved 2018/07/29.