3,4-Dihydroxyacetophenone

Base Information

• Chemical Name: 3,4-Dihydroxyacetophenone
• CAS No.: 1197-09-7
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Hs Code.: 2914501900
• European Community (EC) Number: 670-471-0
• UNII: 07OQ35LVBK
• DSSTox Substance ID: DTXSID30152546
• Nikkaji Number: J7.452G
• Wikidata: Q222992
• Metabolomics Workbench ID: 43967
• ChEMBL ID: CHEMBL243161
• Mol file: 1197-09-7.mol

Synonyms:Acetophenone,3',4'-dihydroxy- (7CI,8CI);1-(3,4-Dihydroxyphenyl)ethan-1-one;1-(3,4-Dihydroxyphenyl)ethanone;3',4'-Dihydroxyacetophenone;4-Acetopyrocatechol;4-Acetyl-1,2-benzenediol;4-Acetylcatechol;4-Acetylpyrocatechol;Acetopyrocatechol;

Chemical Property of 3,4-Dihydroxyacetophenone

Chemical Property:

• Appearance/Colour: light yellow to dark yellow liquid
• Vapor Pressure: 4.5E-06mmHg at 25°C
• Melting Point: 117 °C
• Refractive Index: 1.595
• Boiling Point: 372.407 °C at 760 mmHg
• PKA: 8.00±0.18(Predicted)
• Flash Point: 193.205 °C
• PSA: 57.53000
• Density: 1.291 g/cm³
• LogP: 1.30040
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Soluble), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

3'',4''-Dihydroxyacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC(=C(C=C1)O)O
• Uses: 3'',4''-Dihydroxyacetophenone is an active constituent of Chinese medicine and also has antimelanogenic actiivity.

Technology Process of 3,4-Dihydroxyacetophenone

There total 40 articles about 3,4-Dihydroxyacetophenone 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: 93.0%

1-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)ethan-1-one (22776-09-6) → 1-(3,4-dihydroxyphenyl)ethan-1-one (1197-09-7)

Guidance literature:

With aluminum (III) chloride; In benzene; for 3.5h; Reflux;

DOI:10.1055/s-0032-1318332

Reference yield: 90.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + acetic acid (64-19-7,77671-22-8) → 1-(3,4-dihydroxyphenyl)ethan-1-one (1197-09-7)

Guidance literature:

acetic acid; With trifluoromethylsulfonic anhydride; In nitromethane; at 20 - 60 ℃;

benzene-1,2-diol; In nitromethane; at 60 ℃; for 0.0833333h; regiospecific reaction;

DOI:10.5012/bkcs.2011.32.5.1784

Reference yield: 82.0%

3-bromo-4-hydroxyacetophenone (1836-06-2) → 1-(3,4-dihydroxyphenyl)ethan-1-one (1197-09-7)

Guidance literature:

With copper(ll) sulfate pentahydrate; sodium hydroxide; In water; for 18h; Reflux;

DOI:10.1002/jlcr.1767

upstream raw materials:

1-(benzo[d][1,3]dioxol-6-yl)ethanone

2-methoxyphenyl acetate

dimethyl phthalate

2-chloro-3',4'-dihydroxyacetophenone

Downstream raw materials:

1-(3-cyclohexyloxy-4-hydroxy-phenyl)-ethanone

1-(3,4-diethoxyphenyl)ethanone

3,4-diacetoxyacetophenone

1-(3,4-bis(benzyloxy)phenyl)ethan-1-one

Refernces

• 1、 Lange. "-". . p. 2037. Retrieved 1962.
• 2、 Kopolow et al.. "". . p. 133,135. Retrieved 1973.
• 3、 Cheng, Lu,Wang, Huihui,Cai, Hengrui,Zhang, Jie,Gong, Xu,Han, Wei. "Iron-catalyzed arene C-H hydroxylation". . p. 77 - 81. Retrieved 2021/10/05.
• 4、 López-López, Ernesto Emmanuel,López-Jiménez, Sergio J.,Barroso-Flores, Joaquín,Rodríguez-Cárdenas, Esdrey,Tapia-Tapia, Melina,López-Téllez, Gustavo,Miranda, Luis D.,Frontana-Uribe, Bernardo A.. "Electrochemical reactivity of S-phenacyl-O-ethyl-xanthates in hydroalcoholic (MeOH/H2O 4:1) and anhydrous acetonitrile media". . . Retrieved 2021/04/12.