Methyl 3-formyl-4-hydroxybenzoate

Base Information

• Chemical Name: Methyl 3-formyl-4-hydroxybenzoate
• CAS No.: 24589-99-9
• Molecular Formula: C9H8O4
• Molecular Weight: 180.16
• Hs Code.: 29189900
• European Community (EC) Number: 625-799-9
• DSSTox Substance ID: DTXSID90179335
• Nikkaji Number: J414.072I
• Wikidata: Q72490918
• Mol file: 24589-99-9.mol

Synonyms:Methyl 3-formyl-4-hydroxybenzoate;24589-99-9;3-Formyl-4-hydroxy-benzoic acid methyl ester;Benzoic acid, 3-formyl-4-hydroxy-, methyl ester;5-Carbomethoxysalicylaldehyde;4-Hydroxyisophthalaldehyde acid methyl ester;Methyl 4-hydroxyisophthalaldehydate;BRN 1426212;5-(METHOXYCARBONYL)SALICYLALDEHYDE;MFCD01661473;4-10-00-03622 (Beilstein Handbook Reference);3-Formyl-4-hydroxybenzoic acid methyl ester;Benzoic acid,3-formyl-4-hydroxy-, methyl ester;SCHEMBL310771;methyl 3-formyl4-hydroxybenzoate;DTXSID90179335;Methyl 4-hydroxy-3-formylbenzoate;EX-A3119;methyl 3-formyl-4-hydroxy-benzoate;CL8555;STL185214;AKOS015890844;2-hydroxy-5-methoxycarbonylbenzaldehyde;PS-5864;3-Formyl-4-hydroxybenzoesaure-methylester;AC-24318;LS-37486;Methyl 3-formyl-4-hydroxybenzoate, 97%;SY064893;AM20030445;CS-0000056;FT-0660134;EN300-65384;3-Formyl-4-hydroxybenzoesäure-methylester;A877866;Isophthalaldehydic acid, 4-hydroxy-, methyl ester;Q-102836;Z1020694370;Isophthalaldehydic acid, 4-hydroxy-, methyl ester (6CI,8CI)

Chemical Property of Methyl 3-formyl-4-hydroxybenzoate

Chemical Property:

• Vapor Pressure: 0.000677mmHg at 25°C
• Melting Point: 80-84 °C
• Refractive Index: 1.594
• Boiling Point: 299.287 °C at 760 mmHg
• PKA: 6.56±0.18(Predicted)
• Flash Point: 120.527 °C
• PSA: 63.60000
• Density: 1.311 g/cm³
• LogP: 0.99130
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 180.04225873
• Heavy Atom Count: 13
• Complexity: 202

Purity/Quality:

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

Methyl 3-formyl-4-hydroxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC(=C(C=C1)O)C=O
• Uses: Methyl 3-Formyl-4-hydroxybenzoate is a useful synthetic intermediate in the synthesis of 1,2-Benzisoxazole-5-carboxylic Acid (B197900). Also a useful synthetic intermediate in the synthesis of Roflumilast (R639700); a selective phosphodiesterase 4 (PDE4) inhibitor and antiasthmatic in the treatment of chronic obstructive pulmonary disease.

Technology Process of Methyl 3-formyl-4-hydroxybenzoate

There total 14 articles about Methyl 3-formyl-4-hydroxybenzoate 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: 99.0%

3-formyl-4-hydroxybenzoic acid (584-87-2) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 3-formyl-4-hydroxybenzoate (24589-99-9)

Guidance literature:

With methanol; In hexane; toluene; at 0 - 20 ℃; for 1h;

Reference yield: 97.0%

methanol (67-56-1) + 3-formyl-4-hydroxybenzoic acid (584-87-2) → methyl 3-formyl-4-hydroxybenzoate (24589-99-9)

Guidance literature:

With sulfuric acid; for 12h; Reflux;

DOI:10.1039/c2gc35622h

Reference yield: 88.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + methyl 4-hydroxylbenzoate (99-76-3,156291-94-0) → methyl 3-formyl-4-hydroxybenzoate (24589-99-9)

Guidance literature:

formaldehyd; With triethylamine; magnesium chloride; In tetrahydrofuran; for 0.166667h; Inert atmosphere;

methyl 4-hydroxylbenzoate; In tetrahydrofuran; at 75 ℃; regioselective reaction; Inert atmosphere;

DOI:10.15227/orgsyn.082.0064

upstream raw materials:

methanol

3-formyl-4-hydroxybenzoic acid

hexamethylenetetramine

methyl 4-hydroxylbenzoate

Downstream raw materials:

3-{[(E)-4-Chloro-phenylimino]-methyl}-4-hydroxy-benzoic acid methyl ester

3-{[(E)-4-Fluoro-phenylimino]-methyl}-4-hydroxy-benzoic acid methyl ester

methyl 3-bromo-5-formyl-4-hydroxybenzoate

methyl 4-(tert-butyldimethylsilyloxy)-3-formyl-benzoate

Refernces

• 1、 Tanaka, Kenta,Hoshino, Yujiro,Honda, Kiyoshi. "A novel synthesis of polysubstituted chromenes from various salicylaldehydes and alkynes under mild conditions". . p. 2448 - 2450. Retrieved 2016.
• 2、 Hartmann, Markus,Huber, Jessica,Kramer, Jan S.,Heering, Jan,Pietsch, Larissa,Stark, Holger,Odadzic, Dalibor,Bischoff, Iris,Fürst, Robert,Schr?der, Martin,Akutsu, Masato,Chaikuad, Apirat,D?tsch, Volker,Knapp, Stefan,Biondi, Ricardo M.,Rogov, Vladimir V.,Proschak, Ewgenij. "Demonstrating Ligandability of the LC3A and LC3B Adapter Interface". . p. 3720 - 3746. Retrieved 2021/05/04.
• 3、 -. "Boron-containing small molecule compound, and preparation method and application thereof". Paragraph 0071-0073. . Retrieved 2020/07/13.