4-Cyanobiphenyl

Base Information

• Chemical Name: 4-Cyanobiphenyl
• CAS No.: 2920-38-9
• Deprecated CAS: 1401716-51-5
• Molecular Formula: C13H9N
• Molecular Weight: 179.221
• Hs Code.: 29269090
• European Community (EC) Number: 220-860-2
• NSC Number: 176013
• DSSTox Substance ID: DTXSID0062713
• Nikkaji Number: J306.849H
• Wikidata: Q72457947
• Mol file: 2920-38-9.mol

Synonyms:4-CYANOBIPHENYL;2920-38-9;4-Phenylbenzonitrile;[1,1'-Biphenyl]-4-carbonitrile;4-Biphenylcarbonitrile;p-Phenylbenzonitrile;p-Cyanobiphenyl;Biphenyl-4-carbonitrile;4-Biphenylcarboxylic acid nitrile;(1,1'-Biphenyl)-4-carbonitrile;EINECS 220-860-2;MFCD00001821;NSC 176013;EC 220-860-2;4-Cyanodiphenyl;4-cyano biphenyl;4-cyano-biphenyl;NSC176013;4-phenyl-benzonitrile;4-cyano-1;4-Phenylbenzonitrile, 95%;SCHEMBL72569;DTXSID0062713;AMY19307;STR02867;STK028923;AKOS005380867;CS-W017260;NSC-176013;AC-18311;SY050385;FT-0618301;EN300-70788;3-formyl-1H-Indole-4-carboxylicacidmethylester;A819806;W-106999;Z57900333

Chemical Property of 4-Cyanobiphenyl

Chemical Property:

• Appearance/Colour: beige crystalline powder
• Vapor Pressure: 0.013-0.03Pa at 25℃
• Melting Point: 85-87 °C(lit.)
• Refractive Index: 1.7270 (estimate)
• Boiling Point: 332.3 °C at 760 mmHg
• Flash Point: 155.5 °C
• PSA: 23.79000
• Density: 1.11 g/cm³
• LogP: 3.22528
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: limited soluble
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 179.073499291
• Heavy Atom Count: 14
• Complexity: 211

Purity/Quality:

99% ^*data from raw suppliers

4-Cyanobiphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-36/37/39-26-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)C#N
• Uses: Intermediates of Liquid Crystals

Technology Process of 4-Cyanobiphenyl

There total 440 articles about 4-Cyanobiphenyl 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: 99.0%

4-Methylbiphenyl (644-08-6) → 4-cyano-1,1'-biphenyl (2920-38-9)

Guidance literature:

4-Methylbiphenyl; With hydrogen bromide; dihydrogen peroxide; In tetrachloromethane; water; at 20 ℃; for 1h; Irradiation;

With ammonia; iodine; In tetrachloromethane; water; acetonitrile; at 20 - 60 ℃; for 4h;

DOI:10.1002/ejoc.201402270

Reference yield: 99.0%

4-Phenylbenzaldehyde (3218-36-8) → 4-cyano-1,1'-biphenyl (2920-38-9)

Guidance literature:

With trifluorormethanesulfonic acid; O-benzenesulfonyl-acetohydroxamic acid ethyl ester; In dichloromethane; at 23 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01263

Reference yield: 94.0%

4-bromobenzenecarbonitrile (623-00-7) + triphenylbismuthane (603-33-8) → 4-cyano-1,1'-biphenyl (2920-38-9)

Guidance literature:

With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; triphenylphosphine; cesium fluoride; In N,N-dimethyl-formamide; at 90 ℃; for 1h; Inert atmosphere; Green chemistry;

DOI:10.1016/j.molcata.2016.07.016

upstream raw materials:

benzenediazonium

benzonitrile

hydrogen cyanide

4'-biphenyl chloride

Downstream raw materials:

biphenyl-4-carboxamidine

3,6-bis-biphenyl-4-yl-1,2-dihydro-[1,2,4,5]tetrazine

4-Phenylbenzaldehyde

biphenyl-4-carboxylic acid

Refernces

• 1、 Sau, Samaresh Chandra,Santra, Subhankar,Sen, Tamal K.,Mandal, Swadhin K.,Koley, Debasis. "Abnormal N-heterocyclic carbene palladium complex: Living catalyst for activation of aryl chlorides in Suzuki-Miyaura cross coupling". . p. 555 - 557. Retrieved 2012.
• 2、 Liu, Wei,Hou, Fanyi. "CuBr/proline-catalyzed cross-coupling of unactivated benzene with aryl halides". . p. 368 - 371. Retrieved 2015.
• 3、 Liu, Ping,Yan, Mei,He, Ren. "Bis(imino)pyridine palladium(II) complexes as efficient catalysts for the Suzuki-Miyaura reaction in water". . p. 131 - 134. Retrieved 2010.
• 4、 Campisciano, Vincenzo,Parola, Valeria La,Liotta, Leonarda F.,Giacalone, Francesco,Gruttadauria, Michelangelo. "Fullerene-ionic-liquid conjugates: A new class of hybrid materials with unprecedented properties". . p. 3327 - 3334. Retrieved 2015.
• 5、 Inamoto, Kiyofumi,Campbell, Laura D.,Doi, Takayuki,Koide, Kazunori. "A highly sensitive fluorescence method reveals the presence of palladium in a cross-coupling reaction mixture not treated with transition metals". . p. 3147 - 3148. Retrieved 2012.
• 6、 Zhang, Hui-Hui,Liu, Bin,Wang, Jing,Feng, Ke,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu. "Graphene-supported small-sized palladium nanoparticles made by facile photochemical approaches". . p. 6188 - 6192. Retrieved 2015.
• 7、 Mahdavi, Hossein,Rahmani, Ozra. "Polyacrylamide-g-Reduced Graphene Oxide Supported Pd Nanoparticles as a Highly Efficient Catalyst for Suzuki–Miyaura Reactions in Water". . p. 2292 - 2305. Retrieved 2016.
• 8、 Cassez, Andy,Ponchel, Anne,Hapiot, Frederic,Monflier, Eric. "Unexpected multifunctional effects of methylated cyclodextrins in a palladium charcoal-catalyzed Suzuki-Miyaura reaction". . p. 4823 - 4826. Retrieved 2006.
• 9、 Heugebaert, Thomas S.A.,De Corte, Simon,Sabbe, Tom,Hennebel, Tom,Verstraete, Willy,Boon, Nico,Stevens, Christian V.. "Biodeposited Pd/Au bimetallic nanoparticles as novel Suzuki catalysts". . p. 1410 - 1412. Retrieved 2012.
• 10、 Khazaei, Ardeshir,Khazaei, Marzieh,Nasrollahzadeh, Mahmoud. "Nano-Fe3O4@SiO2 supported Pd(0) as a magnetically recoverable nanocatalyst for Suzuki coupling reaction in the presence of waste eggshell as low-cost natural base". . p. 5624 - 5633. Retrieved 2017.