Biphenylene

Base Information

• Chemical Name: Biphenylene
• CAS No.: 259-79-0
• Deprecated CAS: 95048-68-3,95048-69-4
• Molecular Formula: C12H8
• Molecular Weight: 152.196
• Hs Code.: 29029000
• European Community (EC) Number: 690-155-6
• NSC Number: 101862
• UNII: 0Z64I7D5M2
• DSSTox Substance ID: DTXSID3059765
• Nikkaji Number: J43.482E
• Wikipedia: Biphenylene
• Wikidata: Q3560509
• Metabolomics Workbench ID: 54805
• Mol file: 259-79-0.mol

Synonyms:BIPHENYLENE;259-79-0;Diphenylene;Cyclobutadibenzene;Dibenzocyclobutadiene;1,1'-Biphenylene;UNII-0Z64I7D5M2;0Z64I7D5M2;NSC 101862;NSC-101862;biphenylen;Biphenylene, 99%;Biphenylene (8CI)(9CI);NCIOpen2_001701;AMY013;DTXSID3059765;CHEBI:33079;MFCD00001110;NSC101862;AKOS004907822;AC-26543;AS-56289;B6284;CS-0155947;FT-0653158;F21332;A818122;J-016201;Q3560509

Chemical Property of Biphenylene

Chemical Property:

• Vapor Pressure: 0.0178mmHg at 25°C
• Melting Point: 113-114 °C(lit.)
• Refractive Index: 1.799
• Boiling Point: 262.417 °C at 760 mmHg
• Flash Point: 99.575 °C
• PSA: 0.00000
• Density: 1.19 g/cm³
• LogP: 3.33400
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 152.062600255
• Heavy Atom Count: 12
• Complexity: 133

Purity/Quality:

98%,99%, ^*data from raw suppliers

Biphenylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61-29-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C23

Technology Process of Biphenylene

There total 119 articles about Biphenylene 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: 30.0%

3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (34583-80-7) + chlorobenzene (108-90-7) → triphenylene (217-59-4) + bisbenzocyclobutene (259-79-0) + 2-chloro-1,1'-biphenyl (2051-60-7,108321-69-3) + 3,3′-dimethyl-2,2′,3,3′,4,4′,5,5′-octahydro-1,1′-bi-1H-3-benzazepine + 2,3,4,5-tetrahydro-3-methyl-1-phenyl-1H-3-benzoazepine (129666-25-7)

Guidance literature:

3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine; With sec.-butyllithium; In tetrahydrofuran; pentane; at -78 ℃; for 1h; Inert atmosphere;

chlorobenzene; With sec.-butyllithium; In tetrahydrofuran; pentane; at -78 - 20 ℃; regioselective reaction;

DOI:10.1055/s-0034-1380453

Reference yield: 5.0%

indantrione (938-24-9) → 2-phenylthiophene (825-55-8) + naphthalene (91-20-3,71998-51-1,72931-45-4) + 9-fluorenone (486-25-9,952573-42-1) + bisbenzocyclobutene (259-79-0)

Guidance literature:

With thiophene; at 500 ℃; under 1 - 5 Torr; Further byproducts given. Yields of byproduct given;

DOI:10.1021/ja00400a046

Reference yield:

2-(benzotriazol-1-yl)acetophenone (127876-36-2) → benzoxazole (273-53-0,29791-96-6) + phenanthridine (229-87-8) + 2-phenylbenzo[d]oxazole (833-50-1) + 7H-dibenzo[b,d]azepin-7-one (96794-10-4) + 5,6-dihydrodibenzo[b,d]azepin-7-one (110030-62-1) + 2-phenyl-4H-1,3-benzoxazin-4-one (3084-52-4) + 2-phenyl-4H-3,1-benzoxazin-4-one (1022-46-4) + bisbenzocyclobutene (259-79-0) + 1-phenyl-2-(phenylimino)ethanone (66749-85-7,66749-86-8,1865-10-7) + benzonitrile (100-47-0)

Guidance literature:

With Ti-MCM-41; at 300 ℃; for 2.77778E-06h; under 0.01 Torr; Flash photolysis;

DOI:10.1016/j.apcata.2009.11.003

upstream raw materials:

o-fluorobromobenzene

2,2'-dibromobiphenyl

2-bromo-dibenziodolium; iodide

diphenyleneiodonium

Downstream raw materials:

[1,1′-biphenyl]-2-yldimethylphosphine oxide

biphenyl

asymm.-Indacen, Cyclopentinden

acenaphthylene

Refernces

• 1、 Chinta, Bhavani Shankar,Lee, Daniel,Hoye, Thomas R.. "Coumarin (5,6-Benzo-2-pyrone) Trapping of an HDDA-Benzyne". . p. 2189 - 2193. Retrieved 2021.
• 2、 Ishida, Shintaro,Misawa, Yoshifumi,Sugawara, Shohei,Iwamoto, Takeaki. "Benzodisilacyclobutadienes: 8π-Electron Systems with an Antiaromatic Silicon Ring". . p. 13829 - 13832. Retrieved 2017.
• 3、 Adam,Balci,Kilic. "Oxyfunctionalization of biphenylene by singlet oxygen, hydrogen peroxide/methyltrioxorhenium, and dimethyldioxirane". . p. 8544 - 8546. Retrieved 1998.
• 4、 Wolovsky,Sondheimer. "". . p. 2844. Retrieved 1962.
• 5、 Ahrens, Alexander,Dreuw, Andreas,Hashmi, A. S. K.,Hoffmann, Marvin,Karger, Leonhard F. P.,Lustosa, Danilo M.,Rudolph, Matthias. "Experimental and theoretical studies on gold(iii) carbonyl complexes: reductive C,H- And C,C bond formation". supporting information. p. 8752 - 8760. Retrieved 2021/07/02.