4-Allylbenzene-1,2-diol

Base Information

• Chemical Name: 4-Allylbenzene-1,2-diol
• CAS No.: 1126-61-0
• Molecular Formula: C9H10O2
• Molecular Weight: 150.177
• Hs Code.: 2907299090
• European Community (EC) Number: 683-143-7
• UNII: FG58C4J9BR
• DSSTox Substance ID: DTXSID20150112
• Nikkaji Number: J126.217C
• Wikipedia: Hydroxychavicol
• Wikidata: Q72437390
• Metabolomics Workbench ID: 122296
• ChEMBL ID: CHEMBL111134
• Mol file: 1126-61-0.mol

Synonyms:2-hydroxychavicol;hydroxychavicol

Chemical Property of 4-Allylbenzene-1,2-diol

Chemical Property:

• Vapor Pressure: 0.00128mmHg at 25°C
• Melting Point: 42.0 to 46.0 °C
• Refractive Index: 1.586
• Boiling Point: 289.2 °C at 760 mmHg
• PKA: 9.83±0.10(Predicted)
• Flash Point: 141.7 °C
• PSA: 40.46000
• Density: 1.148 g/cm³
• LogP: 1.82630
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 134

Purity/Quality:

98% MIN ^*data from raw suppliers

4-Allylpyrocatechol >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCC1=CC(=C(C=C1)O)O
• Uses: 4-Allylpyrocatechol (other name: hydroxychavicol), isolated from Piper betle leaves, has been reported as an antimicrobial, antioxidant, and anti-inflammatory agent. In 2009, it was reported as a more potent xanthine oxidase (XO) inhibitor than allopurinol, which is clinically used for the treatment of hyperuricemia.4-Allylpyrocatechol is an antioxidant found in Piper Betel leaf extract. It is widely used as mouth freshener. It is a phenolic compound, considered to be effective against indomethacin-gastropathy.

Technology Process of 4-Allylbenzene-1,2-diol

There total 20 articles about 4-Allylbenzene-1,2-diol 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: 100.0%

C21H18O2Si → 4-allylpyrocatechol (1126-61-0)

Guidance literature:

With water;

DOI:10.1039/c9ra04719k

Reference yield: 99.0%

4-allylguaiacol (97-53-0) → 4-allylpyrocatechol (1126-61-0)

Guidance literature:

With pyridine; aluminium(III) iodide; In acetonitrile; at 80 ℃; for 18h; Reagent/catalyst; Solvent;

DOI:10.1055/s-0035-1588889

Reference yield: 99.0%

1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) → 4-allylpyrocatechol (1126-61-0)

Guidance literature:

With aluminium(III) iodide; diisopropyl-carbodiimide; In acetonitrile; at 80 ℃; for 18h;

DOI:10.1055/s-0036-1588755

upstream raw materials:

methyl magnesium iodide

1,2-dimethoxy-4-(2-propenyl)benzene

2-allyloxyphenol

4-allylguaiacol

Downstream raw materials:

4-propylbenzene-1,2-diol

caffeic acid

dimethyl 2,2'-[(4-allyl-1,2-phenylene)-bis(oxy)]diacetate

4-allyl-1,2-bis-carboxymethoxy-benzene

Refernces

• 1、 Donovan, Brian R.,Cobb, Jared S.,Hoff, Ethan F. T.,Patton, Derek L.. "Thiol-ene adhesives from clove oil derivatives". . p. 61927 - 61935. Retrieved 2014.
• 2、 Alhaffar, Mouheddin T.,Akhtar, Mohammad N.,Ali, Shaikh A.. "Utilization of catecholic functionality in natural safrole and eugenol to synthesize mussel-inspired polymers". . p. 21265 - 21277. Retrieved 2019.
• 3、 Sang, Dayong,Yao, Ming,Tian, Juan,Chen, Xiaoman,Li, Li,Zhan, Hongju,You, Linhong. "Pyridine Improves Aluminum Triiodide Induced Selective Cleavage of Alkyl o -Hydroxyphenyl Ethers: A Practical and Efficient Procedure for the Preparation of Hydroxychavicol by Demethylation of Eugenol". . p. 138 - 142. Retrieved 2017.
• 4、 Kim, Sung-Jin,Vassao, Daniel G.,Moinuddin, Syed G.A.,Bedgar, Diana L.,Davin, Laurence B.,Lewis, Norman G.. "Allyl/propenyl phenol synthases from the creosote bush and engineering production of specialty/commodity chemicals, eugenol/isoeugenol, in Escherichia coli". . p. 37 - 46. Retrieved 2014.
• 5、 -. "PROCESS FOR THE PREPARATION AND IDENTIFICATION OF DEUTERATED EUGENOL". Page/Page column 14-15. . Retrieved 2021/01/22.
• 6、 -. "Selective ether bond breaking method of aryl alkyl ether". Paragraph 0024-0028; 0035-0040. . Retrieved 2020/09/16.