Diphenylmethane

Base Information

• Chemical Name: Diphenylmethane
• CAS No.: 101-81-5
• Molecular Formula: C13H12
• Molecular Weight: 168.238
• Hs Code.: Oral rat: LD50: 2250 mg/kg
• European Community (EC) Number: 202-978-6
• NSC Number: 4708
• UNII: K3E387I0BC
• DSSTox Substance ID: DTXSID1041891
• Nikkaji Number: J3.597A
• Wikipedia: Diphenylmethane
• Wikidata: Q412882,Q83069339
• ChEMBL ID: CHEMBL1796022
• Mol file: 101-81-5.mol

Synonyms:diphenylmethane

Chemical Property of Diphenylmethane

Chemical Property:

• Appearance/Colour: colorless to pale yellow low melting solid
• Vapor Pressure: <1 mm Hg ( 77 °C)
• Melting Point: 24.5 °C
• Refractive Index: n20/D 1.577(lit.)
• Boiling Point: 264.3 °C at 760 mmHg
• PKA: 33.5(at 25℃)
• Flash Point: 104.9 °C
• PSA: 0.00000
• Density: 0.996 g/cm³
• LogP: 3.27740
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in ethanol, ether, benzene and chloroform.
• Water Solubility.: 14.1mg/L(25 oC)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 168.093900383
• Heavy Atom Count: 13
• Complexity: 111

Purity/Quality:

99% ^*data from raw suppliers

Benzylbenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25-58-54-44-29

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C(C=C1)CC2=CC=CC=C2
• Uses: Diphenylmethane is widely used in the synthesis of luminogens for aggregation-induced emission (AIE). It is used in the preparation of a polymerization initiator, diphenylmethyl potassium (DPMK). It is one of the precursors in the synthesis of a dendrimeric polycyclic aromatic hydrocarbon (PAH), hexakis[4-(1,1,2-triphenyl-ethenyl)phenyl]benzene. Diphenylmethane, is used as an adhesive chemical composition for making flexible laminates for use in food packaging.

Technology Process of Diphenylmethane

There total 1220 articles about Diphenylmethane 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: 54.0%

3-benzyl-4-phenyl-1,2,3-oxadiazol-3-ium-5-olate (20067-23-6) → Diphenylmethane (101-81-5) + benzoic acid benzyl ester (120-51-4) + benzyl oxo(phenyl)acetate (62977-82-6) + benzaldehyde (100-52-7) + benzoic acid (65-85-0,8013-63-6) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With oxygen; In benzene; for 336h; Product distribution; Ambient temperature;

DOI:10.1021/jo00157a011

Reference yield: 52.7%

dichloromethane (75-09-2) + phenylmagnesium chloride (100-59-4) → ethylbenzene (100-41-4,27536-89-6) + Diphenylmethane (101-81-5) + toluene (108-88-3,15644-74-3,16713-13-6)

Guidance literature:

With C₃₁H₃₇ClN₃NiO₂^(1-)*Li⁽¹⁺⁾; In tetrahydrofuran; at 25 ℃; for 0.333333h; Overall yield = 99.5 %; Inert atmosphere;

DOI:10.1016/j.molcata.2012.07.007

Reference yield: 10.0%

isoquinoline (119-65-3) + N-benzoyl benzophenone hydrazone (7355-77-3) → N-phenyl benzoyl amide (93-98-1,5705-51-1) + benzophenone (119-61-9) + 1-phenylisoquinoline (3297-72-1) + Diphenylmethane (101-81-5) + N-(diphenylmethylidene)phenylamine (574-45-8) + benzonitrile (100-47-0) + benzil (134-81-6) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

at 200 ℃; for 10h;

DOI:10.1007/s00706-011-0532-4

upstream raw materials:

tetrahydrofuran

ethanol

1,1,2,2-tetraphenyl-ethanol

sodium ethanolate

Downstream raw materials:

diphenylmethyllithium

(methyldiphenylsilyl)diphenylmethane

1,1,2,2-tetraphenylethane

tetraphenylethane-1,2-diol

Refernces

• 1、 Karami, Kazem,Ghasemi, Mahdiyeh,Naeini, Nasrin Haghighat. "Application of a dimeric P,C-palladacycle complex as a catalyst in Suzuki and Heck cross-coupling reactions". . p. 1352 - 1355. Retrieved 2013.
• 2、 Burton,Cheeseman. "-". . p. 986,988. Retrieved 1953.
• 3、 Johnston, Linda J.,Scaiano, J. C.,Shi, Ji-Liang,Siebrand, Willem,Zerbetto, Francesco. "Observation and Modelling of the Recombination Kinetics of Diphenylmethyl Radicals in the Cavities of Na-X Zeolite". . p. 10018 - 10024. Retrieved 1991.
• 4、 Olofsson, Kristofer,Kim, Sun-Young,Larhed, Mats,Curran, Dennis P.,Hallberg, Anders. "High-speed, highly fluorous organic reactions". . p. 4539 - 4541. Retrieved 1999.
• 5、 Anka-Lufford, Lukiana L.,Huihui, Kierra M. M.,Gower, Nicholas J.,Ackerman, Laura K. G.,Weix, Daniel J.. "Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents". . p. 11564 - 11567. Retrieved 2016.
• 6、 Tsuchimoto, Teruhisa,Hiyama, Tamejiro,Fukuzawa, Shin-Ichi. "Scandium(III) trifluoromethanesulfonate-catalysed reductive Friedel-Crafts benzylation of aromatic compounds using arenecarbaldehydes and propane-1,3-diol". . p. 2345 - 2346. Retrieved 1996.
• 7、 Corriu, R.,Guerin, C.,Henner, B.,Wang, Q.. "Pentavalent hydridosilicates: some aspects of the reactivity of potassium tetraethoxyhydridosilicate". . p. C7 - C10. Retrieved 1989.
• 8、 Zhou, Yunwen,Mu, Yanyu,Hsieh, Ming-Feng,Kabius, Bernd,Pacheco, Carlos,Bator, Carol,Rioux, Robert M,Rimer, Jeffrey D.. "Enhanced Surface Activity of MWW Zeolite Nanosheets Prepared via a One-Step Synthesis". . p. 8211 - 8222. Retrieved 2020.
• 9、 Hirsch, Florian,Constantinidis, Philipp,Fischer, Ingo,Bakels, Sjors,Rijs, Anouk M.. "Dimerization of the Benzyl Radical in a High-Temperature Pyrolysis Reactor Investigated by IR/UV Ion Dip Spectroscopy". . p. 7647 - 7652. Retrieved 2018.
• 10、 Sun, Hong-Bin,Li, Biao,Chen, Songjie,Li, Jie,Hua, Ruimao. "An efficient synthesis of unsymmetrical diarylmethanes from the dehydration of arenes with benzyl alcohols using InCl3·4H2O/acetylacetone catalyst system". . p. 10185 - 10188. Retrieved 2007.