Methyl 3,4-dihydroxybenzoate

Base Information

• Chemical Name: Methyl 3,4-dihydroxybenzoate
• CAS No.: 2150-43-8
• Molecular Formula: C8H8O4
• Molecular Weight: 168.149
• Hs Code.: 29182900
• European Community (EC) Number: 677-539-9
• NSC Number: 146458
• UNII: G72J90268X
• DSSTox Substance ID: DTXSID20301804
• Nikkaji Number: J45.023E
• Wikidata: Q10354668
• Pharos Ligand ID: N1BZDN1YCYKP
• Metabolomics Workbench ID: 74818
• ChEMBL ID: CHEMBL486027
• Mol file: 2150-43-8.mol

Synonyms:MDHB compound;methyl 3,4-dihydroxybenzoate

Chemical Property of Methyl 3,4-dihydroxybenzoate

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 2.02E-05mmHg at 25°C
• Melting Point: 134-135°C
• Refractive Index: 1.587
• Boiling Point: 351.5 °C at 760 mmHg
• PKA: 8.19±0.18(Predicted)
• Flash Point: 148.5 °C
• PSA: 66.76000
• Density: 1.354 g/cm³
• LogP: 0.88440
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 26-36-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=C(C=C1)O)O
• Uses: The methyl ester of 3,4-Dihydroxybenzoic Acid (D451680) with antioxidant properties.

Technology Process of Methyl 3,4-dihydroxybenzoate

There total 35 articles about Methyl 3,4-dihydroxybenzoate 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-Dihydroxybenzoic acid (99-50-3) → 3,4-dihydroxybenzoic acid methyl ester (2150-43-8)

Guidance literature:

With thionyl chloride; Heating;

DOI:10.1080/00304940409356628

Reference yield: 98.0%

3-hydroxy-4-methoxybenzoate (6702-50-7) → 3,4-dihydroxybenzoic acid methyl ester (2150-43-8)

Guidance literature:

With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal; In acetonitrile; at 80 ℃; for 18h; Reagent/catalyst;

DOI:10.1021/acs.joc.0c00290

Reference yield: 94.0%

methyl 4-(cyclohex-2-en-1-yloxy)-3-hydroxybenzoate (484018-34-0) → 3,4-dihydroxybenzoic acid methyl ester (2150-43-8)

Guidance literature:

With hydrogenchloride; In diethyl ether; at 20 ℃; for 0.0166667h;

DOI:10.1016/S0040-4039(02)01466-1

upstream raw materials:

methanol

3,4-Dihydroxybenzoic acid

methyl 3,4-methylenedioxybenzoate

4-hydroxy-3-methoxybenzoic acid methyl ester

Downstream raw materials:

methyl 4-(benzyloxy)-3-hydroxybenzoate

3,4-bis-benzyloxybenzoic acid methyl ester

2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Isovanillic acid

Refernces

• 1、 Orjala, Jimmy,Erdelmeier, C. A. J.,Wright, Anthony D.,Rali, Topul,Sticher, Otto. "TWO CHROMENES AND A PRENYLATED BENZOIC ACID DERIVATIVE FROM PIPER ADUNCUM". . p. 813 - 818. Retrieved 1993.
• 2、 Battaini, Giuseppe,De Carolis, Marco,Monzani, Enrico,Tuczek, Felix,Casella, Luigi. "The phenol ortho-oxygenation by mononuclear copper(I) complexes requires a dinuclear μ-η2:η2-peroxodicopper(II) complex rather than mononuclear CuO2 species". . p. 726 - 727. Retrieved 2003.
• 3、 Santagostini, Laura,Gullotti, Michele,Monzani, Enrico,Casella, Luigi,Dillinger, Renee,Tuczek, Felix. "Reversible dioxygen binding and phenol oxygenation in a tyrosinase model system". . p. 519 - 522. Retrieved 2000.
• 4、 Casella, Luigi,Gullotti, Michele,Radaelli, Roberto,Gennaro, Patrizia Di. "A Tyrosinase Model System. Phenol ortho-Hydroxylation by a Binuclear Three-coordinate Copper(I) Complex and Dioxygen". . p. 1611 - 1612. Retrieved 1991.
• 5、 Kim, Tae Hoon,Lee, Jaemin,Kim, Hyun-Joo,Jo, Cheorun. "Plasma-Induced Degradation of Quercetin Associated with the Enhancement of Biological Activities". . p. 6929 - 6935. Retrieved 2017.
• 6、 Straniero, Valentina,Sebastián-Pérez, Victor,Hrast, Martina,Zanotto, Carlo,Casiraghi, Andrea,Suigo, Lorenzo,Zdovc, Irena,Radaelli, Antonia,De Giuli Morghen, Carlo,Valoti, Ermanno. "Benzodioxane-Benzamides as Antibacterial Agents: Computational and SAR Studies to Evaluate the Influence of the 7-Substitution in FtsZ Interaction". . p. 195 - 209. Retrieved 2020.
• 7、 Piguel, Sandrine,Ulibarri, Gerardo,Grierson, David S.. "Studies toward the construction of the allyltrisulfide component in esperamicin-A1 from 5-ketoshikimic acid derivatives: Part 1". . p. 291 - 294. Retrieved 1999.
• 8、 -. "Synthesis and application of acrylic resin based on protocatechuic acid". Paragraph 0049-0050. . Retrieved 2021/06/26.
• 9、 -. "BENZOXAZINONE COMPOUNDS AS KLK5/7 DUAL INHIBITORS". Paragraph 0143-0144; 0157-0159; 0176; 0192-0194. . Retrieved 2021/04/10.