Bis(diphenylmethyl) ether

Base Information

• Chemical Name: Bis(diphenylmethyl) ether
• CAS No.: 574-42-5
• Molecular Formula: C26H22O
• Molecular Weight: 350.46
• Hs Code.: 2909300000
• European Community (EC) Number: 642-198-7
• NSC Number: 2438
• UNII: 13T730HO9L
• DSSTox Substance ID: DTXSID80205990
• Nikkaji Number: J95.751H
• Wikidata: Q27251543
• Mol file: 574-42-5.mol

Synonyms:Bis(diphenylmethyl) ether;574-42-5;Dibenzhydryl ether;Benzhydrol ether;Benzhydryl ether;Diphenylmethyl ether;Bis(benzhydryl) ether;Benzohydrol ether;Dibenzohydryl ether;(Oxybis(methanetriyl))tetrabenzene;Ether, bis(diphenylmethyl);Benzene, 1,1',1'',1'''-(oxydimethylidyne)tetrakis-;[benzhydryloxy(phenyl)methyl]benzene;1,1,1',1'-Tetraphenyldimethyl ether;NSC 2438;UNII-13T730HO9L;13T730HO9L;NSC-2438;1,1',1'',1'''-(Oxydimethylidyne)Tetrakis Benzene;AI3-15103;[Oxybis(methanetriyl)]tetrabenzene (Bis(diphenylmethyl) Ether);[(Benzhydryloxy)(phenyl)methyl]benzene;((BENZHYDRYLOXY)(PHENYL)METHYL)BENZENE;BENZHYDRYL OXIDE;(Bis(diphenylmethyl)ether);SCHEMBL127629;DIMENHYDRINATE IMPURITY K;DTXSID80205990;NSC2438;1,1',1'-Tetraphenyldimethyl ether;MFCD00030056;(1,1,3,3-Tetraphenyl)methyl ether;AKOS024428867;AT11044;[(Benzhydryloxy)(phenyl)methyl]benzene #;1,1,1,1-(Oxydimethylidyne)TetrakisBenzene;BENZOHYDROL DIPHENYLMETHYL ETHER [MI];FT-0723053;DIMENHYDRINATE IMPURITY K [EP IMPURITY];Benzene,1',1'',1'''-(oxydimethylidyne)tetrakis-;Q27251543

Chemical Property of Bis(diphenylmethyl) ether

Chemical Property:

• Melting Point: 181-183℃ (methanol )
• Boiling Point: 464.5 °C at 760 mmHg
• Flash Point: 260.9 °C
• PSA: 9.23000
• Density: 1.105 g/cm³
• LogP: 6.58220
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 350.167065321
• Heavy Atom Count: 27
• Complexity: 320

Purity/Quality:

99% ^*data from raw suppliers

(Bis(diphenylmethyl)ether) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)OC(C3=CC=CC=C3)C4=CC=CC=C4
• General Description: 1,1',1'',1'''-(Oxydimethylidyne)Tetrakis Benzene, also known as bis(diphenylmethyl) ether or benzhydryl ether, is a protective group for alcohols in organic synthesis. It can be efficiently prepared using Nafion-H as a solid acid catalyst, with acetonitrile as the optimal solvent and primary alcohols showing higher reactivity. The method yields high product purity with minimal byproducts like dibenzhydryl ether and demonstrates excellent catalyst recyclability over multiple cycles. Structural confirmation is achieved through techniques such as column chromatography, GC, and 1H NMR.

Technology Process of Bis(diphenylmethyl) ether

There total 219 articles about Bis(diphenylmethyl) ether 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: 97.0%

1,1-Diphenylmethanol (91-01-0) → benzhydryl ether (574-42-5) + toluene-4-sulfonamide (70-55-3)

Guidance literature:

With N-sulfinyl-p-toluenesulfonamide; In diethyl ether; at 25 ℃; for 20h;

DOI:10.1016/S0040-4020(01)92026-5

Reference yield: 95.0%

1,1-Diphenylmethanol (91-01-0) + diphenylmethyl diphenyl phosphate (93845-96-6) → diphenyl hydrogen phosphate (838-85-7) + benzhydryl ether (574-42-5)

Guidance literature:

In dichloromethane; for 0.666667h; Ambient temperature;

DOI:10.1016/S0040-4039(01)91201-8

Reference yield: 52.0%

1,1-Diphenylmethanol (91-01-0) → benzophenone (119-61-9) + benzhydryl ether (574-42-5) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With dibenzoyl peroxide; In dichloromethane; for 3h; Ambient temperature; Irradiation;

upstream raw materials:

ethylmagnesium iodide

diethyl ether

benzhydryl acetate

methyl magnesium iodide

Downstream raw materials:

benzophenone

Diphenylmethane

2,5-bisbenzhydrylthiophene

((tert-butylperoxy)methylene)dibenzene

Refernces

Nafion-catalyzed preparation of benzhydryl ethers

10.1016/S0040-4039(02)01755-0

The research focuses on the development of an efficient and recyclable method for the preparation of benzhydryl ethers, a common protective group for alcohols in organic synthesis. The study utilizes Nafion-H, a perfluorinated sulfonic acid resin, as a solid acid catalyst for this purpose. The experiments involved mixing alcohol and diphenylmethanol in the presence of a catalytic amount of Nafion-H in acetonitrile at 80°C, optimizing the solvent, reaction temperature, and catalyst to substrate ratio. The reaction yield was found to be highest in acetonitrile, with primary alcohols being more reactive than secondary and tertiary alcohols. The method was extended to various hydroxyl compounds, and the results were summarized in a table, showing high yields for benzylic and primary alcohols with minimal formation of dibenzhydryl ether. The catalyst's recyclability was tested over eight reaction cycles without significant loss of activity. The products were analyzed using column chromatography, gas chromatography (GC), and proton nuclear magnetic resonance (1H NMR) to confirm their structures.