Dibenzyl ether

Base Information

• Chemical Name: Dibenzyl ether
• CAS No.: 103-50-4
• Molecular Formula: C14H14O
• Molecular Weight: 198.265
• Hs Code.: 2909 30 90
• European Community (EC) Number: 203-118-2
• NSC Number: 5931
• UNII: 2O6CNO27RJ
• DSSTox Substance ID: DTXSID5025819
• Nikkaji Number: J1.181I
• Wikipedia: Dibenzyl_ether
• Wikidata: Q11309584
• Metabolomics Workbench ID: 45256
• ChEMBL ID: CHEMBL152299
• Mol file: 103-50-4.mol

Synonyms:dibenzyl ether

Chemical Property of Dibenzyl ether

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.00444mmHg at 25°C
• Melting Point: 1.5-3.5 °C(lit.)
• Refractive Index: n20/D 1.562
• Boiling Point: 286.852 °C at 760 mmHg
• Flash Point: 135 °C
• PSA: 9.23000
• Density: 1.047 g/cm³
• LogP: 3.40340
• Storage Temp.: Store below +30°C.
• Solubility.: 42mg/l insoluble
• Water Solubility.: insoluble
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 198.104465066
• Heavy Atom Count: 15
• Complexity: 137

Purity/Quality:

95%, ^*data from raw suppliers

Dibenzyl Ether >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36/37/38-51/53
• Safety Statements: 23-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: C1=CC=C(C=C1)COCC2=CC=CC=C2
• Uses: Benzyl ether is used as an effective GFP friendly tissue clearing medium for mouse brains. It is also used in a study to develop a detailed protocol for performing 3D imaging of solvent-cleared organs and its application to various microscopy techniques. It is also employed as a plasticizer for nitrocellulose and synthetic rubber, a solvent in perfumery, and a flavoring agent in chewing gums and baked goods. Benzyl ether was used as an effective GFP friendly tissue clearing medium for mouse brains. It was used in a study to develop a detailed protocol for performing 3D imaging of solvent-cleared organs and its application to various microscopy techniques. Plasticizer for nitrocellulose; solvent in perfumery.

Technology Process of Dibenzyl ether

There total 417 articles about Dibenzyl 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: 90.0%

benzyl alcohol (100-51-6,185532-71-2) → dibenzyl ether (103-50-4) + benzaldehyde (100-52-7)

Guidance literature:

With polystyrene-supported(catecholato) oxoRe cat. act. by iPrOH; dimethyl sulfoxide; In toluene; for 2h; Heating; Dean-Stark apparatus;

DOI:10.1002/1522-2675(200210)85:10<3225::AID-HLCA3225>3.0.CO;2-H

Reference yield: 86.0%

benzaldehyde (100-52-7) → dibenzyl ether (103-50-4) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With Dimethylphenylsilane; In 1,1,2,2-tetrachloroethane; at 100 ℃; for 3h; chemoselective reaction;

DOI:10.1039/c7cy00336f

Reference yield: 75.0%

benzyl alcohol (100-51-6,185532-71-2) → dibenzyl ether (103-50-4) + benzyl chloride (100-44-7)

Guidance literature:

With bismuth(III) chloride; In tetrachloromethane; at 25 ℃; for 0.333333h; Yields of byproduct given;

DOI:10.1080/00397919808007004

upstream raw materials:

benzoic acid

bis(bromomethyl) ether

DBC

lithium methanolate

Downstream raw materials:

3-benzyldihydrofuran-2,5-dione

benzyl bromide

benzaldehyde

1-(ethoxymethyl)benzene

Refernces

• 1、 Du, Yuan-Peng,Héroguel, Florent,Nguyen, Xuan Trung,Luterbacher, Jeremy S.. "Post-synthesis deposition of mesoporous niobic acid with improved thermal stability by kinetically controlled sol-gel overcoating". . p. 23803 - 23811. Retrieved 2019.
• 2、 Stavber, Gaj,Zupan, Marko,Stavber, Stojan. "Iodine induced transformations of alcohols under solvent-free conditions". . p. 8463 - 8466. Retrieved 2006.
• 3、 Fan, Wenqing,Zhang, Qinghong,Deng, Weiping,Wang, Ye. "Niobic acid nanosheets synthesized by a simple hydrothermal method as efficient Bronsted acid catalysts". . p. 3277 - 3287. Retrieved 2013.
• 4、 Balu, Alina M.,Pineda, Antonio,Obermayer, David,Romero, Antonio A.,Kappe, C. Oliver,Luque, Rafael. "Versatile low-loaded mechanochemically synthesized supported iron oxide nanoparticles for continuous flow alkylations". . p. 16292 - 16295. Retrieved 2013.
• 5、 Suzuki, Takeshi,Oriyama, Takeshi. "Novel reactions of ethylene acetals with silyl-substituted nucleophiles. A mild and efficient procedure for the synthesis of homoallyl alkyl ethers and unsymmetrical dialkyl ethers". . p. 1263 - 1269. Retrieved 1999.
• 6、 Jia, Xiangkun,Fan, Xinlong,Liu, Yin,Li, Wei,Tian, Lei,Fan, Lili,Zhang, Baoliang,Zhang, Hepeng,Zhang, Qiuyu. "Quaternary ammonium functionalized Fe3O4@P(GMA-EGDMA) composite particles as highly efficient and dispersible catalysts for phase transfer reactions". . p. 60691 - 60697. Retrieved 2015.
• 7、 Takagaki, Atsushi,Tagusagawa, Caio,Takanabe, Kazuhiro,Kondo, Junko N.,Tatsumi, Takashi,Domen, Kazunari. "Effect of post-calcination thermal treatment on acid properties and pores structure of a mesoporous niobium-tungsten oxide". . p. 144 - 148. Retrieved 2012.
• 8、 Shimagaki et al.. "-". . p. 3435. Retrieved 1978.
• 9、 Komatsu, Naoki,Ishida, Jun-Ya,Suzuki, Hitomi. "Bismuth Bromide-Catalyzed reductive coupling of carbonyl compounds and its application to the synthesis of novel crownophanes". . p. 7219 - 7222. Retrieved 1997.
• 10、 Yadav, Ganapati D.,Sharma, Rajesh V.. "Synthesis, characterization and applications of highly active and robust sulfated Fe-TiO2 catalyst (ICT-3) with superior redox and acidic properties". . p. 121 - 128. Retrieved 2014.