[1,1'-Biphenyl]-4,4'-dicarbonitrile

Base Information

• Chemical Name: [1,1'-Biphenyl]-4,4'-dicarbonitrile
• CAS No.: 1591-30-6
• Molecular Formula: C14H8 N2
• Molecular Weight: 204.231
• Hs Code.: 2926909090
• European Community (EC) Number: 216-468-6
• NSC Number: 87879
• UNII: 39C3SL9TAG
• DSSTox Substance ID: DTXSID2061806
• Nikkaji Number: J79.020F
• Wikidata: Q81989682
• Mol file: 1591-30-6.mol

Synonyms:1591-30-6;4,4'-BIPHENYLDICARBONITRILE;[1,1'-Biphenyl]-4,4'-dicarbonitrile;4,4'-Dicyanobiphenyl;Biphenyl-4,4'-dicarbonitrile;4,4'-Dicyanodiphenyl;4-(4-cyanophenyl)benzonitrile;4,4'-Diphenyldicarbonitrile;MFCD00013805;(1,1'-Biphenyl)-4,4'-dicarbonitrile;EINECS 216-468-6;NSC 87879;1,1'-Biphenyl-4,4'-dicarbonitrile;39C3SL9TAG;NSC-87879;4,4 inverted exclamation mark -Biphenyldicarbonitrile;4,4-Dicyanodiphenyl;EM-3993;4,4'-Bibenzonitrile;4,4'-Dibenzonitrile;[1,4'-dicarbonitrile;4,4/'-Dicyanobiphenyl;Maybridge3_005590;WLN: NCR DR DCN;UNII-39C3SL9TAG;SCHEMBL26246;YSWG189;Biphenyl-4,4''-dicarbonitrile;DTXSID2061806;HMS1446O02;BCP32356;NSC87879;4,4'-Biphenyldicarbonitrile, 97%;4,4\'-BIPHENYLDICARBONITRILE;AKOS015836412;AM85610;RS-1004;IDI1_016977;AC-27900;LS-44295;SY049676;B1181;CS-0110274;FT-0617003;A856070;W-107989

Chemical Property of [1,1'-Biphenyl]-4,4'-dicarbonitrile

Chemical Property:

• Melting Point: 236-236oC
• Refractive Index: 1.6152 (estimate)
• Boiling Point: 403.5°Cat760mmHg
• Flash Point: 199.2°C
• PSA: 47.58000
• Density: 1.2g/cm³
• LogP: 3.09696
• Water Solubility.: Insoluble in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 204.068748264
• Heavy Atom Count: 16
• Complexity: 279

Purity/Quality:

98% ^*data from raw suppliers

4,4''-Biphenyldicarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)C2=CC=C(C=C2)C#N
• Uses: Biphenyl-4,4'-dicarbonitrile is used as a pharmaceutical intermediate.

Technology Process of [1,1'-Biphenyl]-4,4'-dicarbonitrile

There total 165 articles about [1,1'-Biphenyl]-4,4'-dicarbonitrile 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: 95.0%

4-bromobenzenecarbonitrile (623-00-7) + zinc (7440-66-6) → (1,1'-biphenyl)-4,4'-dicarbonitrile (1591-30-6) + 4-cyanophenylzinc bromide (131379-14-1) + benzonitrile (100-47-0)

Guidance literature:

With trifluoroacetic acid; cobalt(II) bromide; zinc dibromide; In acetonitrile; the mixt. in CH3CN was stirred at room temp., then arylbromide was added, stirred at room temp.; GC analysis;

DOI:10.1021/ja0289494

Reference yield: 92.0%

4-Cyanochlorobenzene (623-03-0) → (1,1'-biphenyl)-4,4'-dicarbonitrile (1591-30-6) + benzonitrile (100-47-0)

Guidance literature:

With potassium hydroxide; In water; N,N-dimethyl-formamide; at 35 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ja309606k

Reference yield: 85.0%

4-iodobenzonitrile (3058-39-7) + (p-methoxyphenyl)dimethylsilanol (22868-26-4) → (1,1'-biphenyl)-4,4'-dicarbonitrile (1591-30-6) + 4'-methoxybiphenyl-4-carbonitrile (58743-77-4)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); triphenyl-arsane; caesium carbonate; In toluene; at 90 ℃; for 6h;

DOI:10.1021/ol034328j

upstream raw materials:

p,p'-diaminobiphenyl

4,4'-dinitrobiphenyl

potassium cyanide

sodium cyanide

Downstream raw materials:

4,4'-diacetylbiphenyl

4,4'-bis(4,5-dihydro-1H-imidazol-2-yl)biphenyl

4,4'-dibenzoyl-1,1'-biphenyl

4,4'-Bis-phenylacetyl-biphenyl

Refernces

• 1、 Kuroboshi, Manabu,Shiba, Takuya,Tanaka, Hideo. "Viologen as catalytic organic reductant: Electro-reductive dimerization of aryl bromides in a Pd/viologen double mediatory system". . p. 3666 - 3668. Retrieved 2013.
• 2、 Semmelhack et al.. "-". . p. 5908. Retrieved 1971.
• 3、 Contreras-Celedón, Claudia Araceli,Rincón-Medina, José Arturo,Mendoza-Rayo, Darío,Chacón-García, Luis. "Oxidative homocoupling of arylboronic acids catalyzed by a 4-aminoantipyrine-Pd(II)complex". . p. 439 - 442. Retrieved 2015.
• 4、 Prasad, K. Sudhakara,Noh, Hui-Bog,Reddy, S. Subba,Reddy, A. Eswar,Shim, Yoon-Bo. "Catalytic properties of Au and Pd nanoparticles decorated on Cu 2O microcubes for aerobic benzyl alcohol oxidation and Suzuki-Miyaura coupling reactions in water". . p. 72 - 77. Retrieved 2014.
• 5、 Rafiee, Fatemeh,Khavari, Parvaneh,Payami, Zahra,Ansari, Narges. "Palladium nanoparticles immobilized on the magnetic few layer graphene support as a highly efficient catalyst for ligand free Suzuki cross coupling and homo coupling reactions". . p. 78 - 85. Retrieved 2019.
• 6、 Prasanna,Bhat, Shrikanth K.,Usha,Hegde. "Ligand and Base Free Synthesis of Biaryls from Aryl Halides in Aqueous Media with Recyclable Ti0.97Pd0.03O1.97 Catalyst". . p. 3313 - 3322. Retrieved 2021.
• 7、 Moncomble, Aurelien,Floch, Pascal Le,Gosmini, Corinne. "Cobalt-catalyzed formation of symmetrical biaryls and its mechanism". . p. 4770 - 4774. Retrieved 2009.
• 8、 Abiraj,Srinivasa,Gowda, D. Channe. "Novel and efficient synthesis of symmetrical functionalized biaryls using zinc and triethylammonium formate". . p. 877 - 879. Retrieved 2004.
• 9、 Peng, Jianbiao,Liu, Xiang,Kishi, Yoshito. "Catalytic homocoupling of aryl, alkenyl, and alkynyl halides with Ni(II)-complexes and zirconocene dichloride". . p. 2172 - 2175. Retrieved 2011.
• 10、 Uberman, Paula M.,Martin, Sandra E.,Rossi, Roberto A.. "Synthesis of functionalized diaryldimethylstannanes from the Me 2Sn2- dianion by SRN1 reactions". . p. 9063 - 9066. Retrieved 2005.