Methyl 3,4-dihydroxyphenylacetate

Base Information

• Chemical Name: Methyl 3,4-dihydroxyphenylacetate
• CAS No.: 25379-88-8
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 2918290000
• European Community (EC) Number: 680-000-0
• DSSTox Substance ID: DTXSID70451666
• Nikkaji Number: J1.187.301D
• Wikidata: Q72490182
• ChEMBL ID: CHEMBL3120494
• Mol file: 25379-88-8.mol

Synonyms:25379-88-8;Methyl 2-(3,4-dihydroxyphenyl)acetate;Methyl 3,4-dihydroxyphenylacetate;3,4-Dihydroxyphenylacetic Acid Methyl Ester;CHEMBL3120494;Benzeneacetic acid, 3,4-dihydroxy-, methyl ester;Homoprotocatechuic Acid Methyl Ester;methyl (3,4-dihydroxyphenyl)acetate;methyl homoprotocatechuate;SCHEMBL3668882;DTXSID70451666;UGFILLIGHGZLHE-UHFFFAOYSA-N;BDBM50062147;Catechol-4-acetic Acid Methyl Ester;MFCD00583539;AKOS015900183;Methyl2-(3,4-dihydroxyphenyl)acetate;CS-W017123;Pyrocatechol-4-acetic Acid Methyl Ester;AS-44408;PD169377;ERGOLINE-8-CARBOXYLICACIDMETHYLESTER;D2734;FT-0638516;(3,4-dihydroxyphenyl)-acetic acid methyl ester;EN300-732967;A817833;J-015971

Chemical Property of Methyl 3,4-dihydroxyphenylacetate

Chemical Property:

• Vapor Pressure: 6.34E-05mmHg at 25°C
• Melting Point: 36ºC
• Refractive Index: 1.575
• Boiling Point: 335 °C at 760 mmHg
• PKA: 9.48±0.12(Predicted)
• Flash Point: 136.2 °C
• PSA: 66.76000
• Density: 1.309 g/cm³
• LogP: 0.81330
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,4-Dihydroxyphenylacetic Acid Methyl Ester ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC1=CC(=C(C=C1)O)O
• Uses: 3,4-Dihydroxyphenylacetic Acid Methyl Ester is a biogenic amine metabolite. 3,4-Dihydroxyphenylacetic Acid Methyl Ester is used in the preparation of antioxidants and bacteriostatic agents. It is used in the synthesis of noncompetitive AMPA receptor antagonists as benzodiazepines, as well as optically active quinolones with dopaminergic properties. 3,4-Dihydroxyphenylacetic Acid Methyl Ester is a biogenic amine metabolite. 3,4-Dihydroxyphenylacetic Acid Methyl Ester is used in the preparation of antioxidants and bacteriostatic agents. It is used in the synthesis of noncompetitive AMPA receptor antagonists as benzodiazepines, as well as optically active quinolones with dopaminergic properties.

Technology Process of Methyl 3,4-dihydroxyphenylacetate

There total 10 articles about Methyl 3,4-dihydroxyphenylacetate 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%

methanol (67-56-1) + 3,4-dihydroxyphenylacetate (102-32-9) → 2-(3,4-dihydroxyphenyl)acetic acid methyl ester (25379-88-8)

Guidance literature:

With sulfuric acid; for 2h; Reflux; Darkness; Inert atmosphere;

DOI:10.1039/c1jm12863a

Reference yield: 98.0%

Methyl 4-hydroxyphenylacetate (14199-15-6) → 2-(3,4-dihydroxyphenyl)acetic acid methyl ester (25379-88-8)

Guidance literature:

With Agaricus bisporus; oxygen; In aq. phosphate buffer; dichloromethane; at 25 ℃; for 24h; pH=7;

DOI:10.1016/j.bmc.2013.10.026

Reference yield: 87.6%

methanol (67-56-1) + 3,4-dihydroxymandelic acid (775-01-9) → 2-(3,4-dihydroxyphenyl)acetic acid methyl ester (25379-88-8)

Guidance literature:

With hydrogenchloride; hydrogen; 5% ruthenium on carbon; In water; at 55 ℃; for 26h; under 18751.9 Torr; Product distribution / selectivity;

upstream raw materials:

methanol

3,4-dihydroxyphenylacetate

sulfuric acid

methyl 2-(3,4-dihydroxyphenyl)-2-hydroxyacetate

Downstream raw materials:

methyl [3,4-bis(tert-butyldimethylsilyloxy)phenyl]acetate

benzo[1,3]dioxol-5-yl-acetic acid methyl ester

3,4-bis(tetrahydropyran-2-yloxy)phenylacetic acid methyl ester

2-(2,2-dimethylbenzo[1,3]dioxol-5-yl)acetic acid methyl ester

Refernces

• 1、 Hu, Zhifei,Silipo, Alba,Li, Wei,Molinaro, Antonio,Yu, Biao. "Synthesis of Forsythenethoside A, a Neuroprotective Macrocyclic Phenylethanoid Glycoside, and NMR Analysis of Conformers". . p. 13733 - 13743. Retrieved 2019.
• 2、 Fu, Hua,Li, Hongyun,Li, Youshan,Lou, Zhenbang,Yang, Haijun,Zhao, Yufen. "Bioorthogonal Ligation and Cleavage by Reactions of Chloroquinoxalines with ortho-Dithiophenols". supporting information. p. 3671 - 3677. Retrieved 2020/02/04.
• 3、 Horii, Toshihiro,Itagaki, Sawako,Kawano, Tomikazu,Miyoshi, Akihito,Murakami, Nobutoshi,Tamura, Satoru. "Structure–Activity Relationship of Anti-malarial Allylpyrocatechol Isolated from Piper betle". . p. 784 - 790. Retrieved 2020/09/18.