5,5'-Methylenedisalicylic acid

Base Information

• Chemical Name: 5,5'-Methylenedisalicylic acid
• CAS No.: 122-25-8
• Molecular Formula: C15H12O6
• Molecular Weight: 288.257
• Hs Code.: 29182900
• European Community (EC) Number: 204-530-5
• NSC Number: 622445,14778
• UNII: 2KF4FVV76N
• DSSTox Substance ID: DTXSID4074481
• Nikkaji Number: J5.352J
• Wikidata: Q27254869
• ChEMBL ID: CHEMBL115145
• Mol file: 122-25-8.mol

Synonyms:3,3'-methylenebis(6-hydroxybenzoic acid);5,5'-methylenedisalicylic acid;5,5'-methylenedisalicylic acid, zinc (1:1) salt;methylenedisalicylic acid

Chemical Property of 5,5'-Methylenedisalicylic acid

Chemical Property:

• Appearance/Colour: cream powder
• Melting Point: 235-242 °C
• Refractive Index: 1.4413 (estimate)
• Boiling Point: 569.6 °C at 760 mmHg
• PKA: 2.94±0.10(Predicted)
• Flash Point: 312.3 °C
• PSA: 115.06000
• Density: 1.511 g/cm³
• LogP: 2.08500
• Water Solubility.: insoluble
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 288.06338810
• Heavy Atom Count: 21
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

5,5''-Methylenebis(2-hydroxybenzoicAcid)(~90%) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CC2=CC(=C(C=C2)O)C(=O)O)C(=O)O)O

Technology Process of 5,5'-Methylenedisalicylic acid

There total 10 articles about 5,5'-Methylenedisalicylic acid 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: 92.0%

3,3'-dichloro-5,5'-dicarboxy-4,4'-dihydroxydiphenylmethane (128626-47-1) → 5,5'-methylenedisalicylic acid (122-25-8)

Guidance literature:

With 760 torr; hydrogen; palladium on activated charcoal; In ethanol; triethylamine; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81957-8

Reference yield: 87.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → 5,5'-methylenedisalicylic acid (122-25-8)

Guidance literature:

With sulfuric acid; for 10h; Reflux;

DOI:10.1248/cpb.56.1732

Reference yield: 66.0%

methyl 2-methoxy-5-{[4-methoxy-3-(methoxycarbonyl)phenyl]methyl}benzoate (207743-19-9) → 5,5'-methylenedisalicylic acid (122-25-8)

Guidance literature:

methyl 2-methoxy-5-{[4-methoxy-3-(methoxycarbonyl)phenyl]methyl}benzoate; With boron tribromide; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

With lithium hydroxide; In tetrahydrofuran; water; at 60 ℃; for 16h;

DOI:10.1016/j.bmcl.2019.01.022

upstream raw materials:

formaldehyd

salicylic acid

3,3'-dichloro-5,5'-dicarboxy-4,4'-dihydroxydiphenylmethane

hydrogenchloride

Downstream raw materials:

bis-(4-hydroxyphenyl)methane

2-hydroxy-5-(4-hydroxy-benzyl)-benzoic acid

4,4'-methylenebis[2-(hydroxymethyl)phenol]

3-(3-carboxy-4-hydroxy-benzyliden)-6-oxo-cyclohexa-1,4-dienecarboxylic acid

Refernces

• 1、 Smith,Sager,Siewers. "-". . p. 1334,1337. Retrieved 1949.
• 2、 Leroy, Maxime,Mélin, Léa,LaPlante, Steven R.,Medina-Franco, José L.,Gagnon, Alexandre. "Synthesis of NSC 106084 and NSC 14778 and evaluation of their DNMT inhibitory activity". supporting information. p. 826 - 831. Retrieved 2019/01/30.
• 3、 -. "Renewable bisphenols and resins from salicylic acid". Page/Page column 10. . Retrieved 2017/01/02.