4,4'-Methylenebis(2,6-dimethylphenol)

Base Information

• Chemical Name: 4,4'-Methylenebis(2,6-dimethylphenol)
• CAS No.: 5384-21-4
• Molecular Formula: C17H20O2
• Molecular Weight: 256.345
• Hs Code.: 2907299090
• European Community (EC) Number: 226-378-9
• NSC Number: 128403
• UNII: JH6FV2EG7J
• DSSTox Substance ID: DTXSID4063820
• Nikkaji Number: J103.329H
• Wikipedia: Tetramethyl_bisphenol_F
• Wikidata: Q65643373
• ChEMBL ID: CHEMBL593206
• Mol file: 5384-21-4.mol

Synonyms:4,4'-Methylenebis(2,6-dimethylphenol);5384-21-4;4,4'-Methylenedi-2,6-xylenol;4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol;Bis(4-hydroxy-3,5-dimethylphenyl)methane;Bis(3,5-dimethyl-4-hydroxyphenyl)methane;Phenol, 4,4'-methylenebis[2,6-dimethyl-;4,6-xylenol;2,6-Xylenol, 4,4'-methylenedi-;JH6FV2EG7J;4,4'-Dihydroxy-3,3',5,5'-tetramethyldiphenylmethane;Phenol, 4,4'-methylenebis(2,6-dimethyl-;EINECS 226-378-9;NSC-128403;EC 226-378-9;3,3',5,5'-Tetramethyl-4,4'-dihydroxydiphenylmethane;Desoxon M;NSC128403;TMBPF;4,6-xylenol];4,6-dimethylphenol);UNII-JH6FV2EG7J;SCHEMBL68876;CHEMBL593206;DTXSID4063820;AZZWZMUXHALBCQ-UHFFFAOYSA-;BP_11;4,4'-Methylenebis[2,6-xylenol];MFCD00055640;AKOS015839108;4,3',5,5'-tetramethyldiphenylmethane;NSC 128403;Phenol,4'-methylenebis[2,6-dimethyl-;4,4\'-Methylenebis(2,6-dimethylphenol);AS-63207;CS-0207078;M1099;C(c1cc(C)c(O)c(C)c1)c2cc(C)c(O)c(C)c2;EN300-248171;F15423;2,2',6,6'-Tetramethyl-4,4'-methylenediphenol;3,5,5'-Tetramethyl-4,4'-dihydroxydiphenylmethane;4-[(4-hydroxyphenyl)methyl]-2,6-dimethyl-phenol;A829793;AB-131/40897252;3,3,5,5-Tetramethyl-4,4-dihydroxy-diphenylmethane;W-110030;4-(4-hydroxy-3,5-dimethylbenzyl)-2,6-dimethylphenol;Q65643373

Chemical Property of 4,4'-Methylenebis(2,6-dimethylphenol)

Chemical Property:

• Appearance/Colour: Crystalline powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 176 °C
• Boiling Point: 414.7 °C at 760 mmHg
• PKA: 10.21±0.10(Predicted)
• Flash Point: 193.6 °C
• PSA: 40.46000
• Density: 1.11 g/cm³
• LogP: 3.92220
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: 3.95g/L in organic solvents at 20 ℃
• Water Solubility.: 100mg/L at 25℃
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 256.146329876
• Heavy Atom Count: 19
• Complexity: 239

Purity/Quality:

98% ^*data from raw suppliers

4,4''-Methylenebis(2,6-dimethylphenol) ^*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: CC1=CC(=CC(=C1O)C)CC2=CC(=C(C(=C2)C)O)C

Technology Process of 4,4'-Methylenebis(2,6-dimethylphenol)

There total 38 articles about 4,4'-Methylenebis(2,6-dimethylphenol) 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: 94.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2.6-dimethylphenol (576-26-1,25134-01-4) → bis(4-hydroxy-3,5-dimethylphenyl)methane (5384-21-4)

Guidance literature:

With silica supported perchloric acid; In neat (no solvent); for 4.25h; Reagent/catalyst; Solvent; Catalytic behavior; Heating; Green chemistry;

DOI:10.1080/00304948.2020.1762459

Reference yield: 86.0%

4,4'-(oxybis(methylene))bis(2,6-dimethylphenol) (71655-87-3) → bis(4-hydroxy-3,5-dimethylphenyl)methane (5384-21-4)

Guidance literature:

With proton exchanged montmorillonite; In dichloromethane; at 25 ℃; for 0.25h;

DOI:10.1016/j.tetlet.2020.152584

Reference yield: 55.0%

Mesitol (527-60-6) → bis(4-hydroxy-3,5-dimethylphenyl)methane (5384-21-4)

Guidance literature:

With ammonium acetate; potassium hexacyanoferrate(III); In methanol; water; at 45 ℃; for 240h;

DOI:10.1021/jo00183a024

upstream raw materials:

formaldehyd

2.6-dimethylphenol

ethanol

3,5-dimethyl-4-hydroxybenzyl bromide

Downstream raw materials:

dibromo-3,4 dimethylphenol-2,6

4,4'-Dimethoxy-3,3',5,5'-tetramethyldiphenylmethane

2,6-dimethyl-4-[(E)-(2,4-dinitrophenyl)diazenyl]phenol

4,4’-methylenebis(2,6-dimethylphenol) diglycidyl ether

Refernces

• 1、 Deota, Pradeep T.,Parmar, Hemant S.,Valodkar, Vaibhav B.,Upadhyay, Piyush R.,Sahoo. "Oxidative acetylation of tetramethyl bisphenol-F". . p. 673 - 678. Retrieved 2006.
• 2、 Singh, Sanjay,Mahato, Rina,Sharma, Pragya,Yadav, Naveen,Vodnala, Nagaraju,Kumar Hazra, Chinmoy. "Development of Transition-Metal-Free Lewis Acid-Initiated Double Arylation of Aldehyde: A Facile Approach Towards the Total Synthesis of Anti-Breast-Cancer Agent". supporting information. . Retrieved 2022/02/19.
• 3、 Chen, Dongyin,Chen, Xuan,Dong, Zezhong,Jiang, Nan,Li, Fei,Yun, Yangfang,Zhou, Yu. "Unusual transformation of 4-hydroxy/methoxybenzylic alcohols via C[sbnd]C ipso-substitution reaction using proton-exchanged montmorillonite as media". supporting information. . Retrieved 2020/11/12.