4,4'-Dimethoxy-1,1'-biphenyl

Base Information

• Chemical Name: 4,4'-Dimethoxy-1,1'-biphenyl
• CAS No.: 2132-80-1
• Molecular Formula: C14H14O2
• Molecular Weight: 214.264
• Hs Code.: 2909309090
• NSC Number: 17524
• DSSTox Substance ID: DTXSID30175593
• Nikkaji Number: J254.633G
• Wikidata: Q63395236
• Metabolomics Workbench ID: 124287
• ChEMBL ID: CHEMBL1735271
• Mol file: 2132-80-1.mol

Synonyms:2132-80-1;4,4'-Dimethoxy-1,1'-biphenyl;4,4'-DIMETHOXYBIPHENYL;1-methoxy-4-(4-methoxyphenyl)benzene;1,1'-Biphenyl, 4,4'-dimethoxy-;4,4'-Dimethoxy-biphenyl;NSC17524;4,4'-Bianisole;p-(4-methoxyphenyl)anisole;Biphenyl,4,4'-dimethoxy-;4-(4-methoxyphenyl)anisole;MLS000550145;SCHEMBL197522;4,4'-Dimethoxybiphenyl, 99%;CHEMBL1735271;SCHEMBL12015236;DTXSID30175593;HMS2329L07;4,4'-DI-METHOXY-BIPHENYL;4,4'-Dimethoxy-1,1'-biphenyl #;MFCD00008402;NSC 17524;NSC-17524;AKOS003342509;1-methoxy-4-(4-methoxyphenyl)-benzene;NCGC00247070-01;AC-20959;AS-59595;SMR000113794;CS-0150407;FT-0634055;D94708;A815276;AB-131/05736040;J-013998;Q63395236

Chemical Property of 4,4'-Dimethoxy-1,1'-biphenyl

Chemical Property:

• Appearance/Colour: light yellow shiny flakes
• Melting Point: 179-180 °C (subl.)(lit.)
• Refractive Index: 1.5570 (estimate)
• Boiling Point: 338.4 °C at 760 mmHg
• Flash Point: 137.4 °C
• PSA: 18.46000
• Density: 1.057 g/cm³
• LogP: 3.37080
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 214.099379685
• Heavy Atom Count: 16
• Complexity: 167

Purity/Quality:

99% ^*data from raw suppliers

4,4′-Dimethoxybiphenyl 99% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=CC=C(C=C2)OC
• Uses: 4,4′-Dimethoxybiphenyl was used to study the coupled methyl-group rotation and methoxy-group libration.

Technology Process of 4,4'-Dimethoxy-1,1'-biphenyl

There total 742 articles about 4,4'-Dimethoxy-1,1'-biphenyl 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: 92.0%

2-bromothiophene (1003-09-4) + 4-methoxyphenyl magnesium bromide (13139-86-1) → 2-(4-methoxyphenyl)thiophene (42545-43-7) + 4,4'-Dimethoxybiphenyl (2132-80-1) + 2,2'-Bithiophene (492-97-7)

Guidance literature:

4-methoxyphenyl magnesium bromide; With bismuth(III) chloride;

2-bromothiophene; With potassium phosphate; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 90 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0030-1260554

Reference yield: 86.0%

para-nitrophenyl triflate (17763-80-3) + tris[2-(perfluorohexyl)ethyl](4'-methoxyphenyl)tin → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4-methoxy-4'-nitrobiphenyl (2143-90-0) + 4,4'-Dimethoxybiphenyl (2132-80-1) + chlorotris[2-(perfluorohexyl)ethyl]tin

Guidance literature:

With lithium chloride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 80 ℃; for 22h;

DOI:10.1021/jo9709413

Reference yield: 81.0%

para-iodoanisole (696-62-8) + o-cyanobromobenzene (2042-37-7) → biphenyl-2,2'-dicarbonitrile (4341-02-0) + 4,4'-Dimethoxybiphenyl (2132-80-1) + 4'-methoxybiphenyl-2-carbonitrile (125610-78-8) + benzonitrile (100-47-0)

Guidance literature:

With pyridine; tetrabutylammonium tetrafluoroborate; In acetonitrile; at 20 ℃; Electrolysis; iron rod as anode; stainless steel grid as cathode;

DOI:10.1016/S0040-4020(02)01030-X

upstream raw materials:

1-bromo-4-methoxy-benzene

7-bromo-benzo[1,3]dioxole-5-carbaldehyde

para-iodoanisole

bis(p-anisyl)mercury

Downstream raw materials:

4,4'-dimethoxy-[1,1'-biphenyl]-2-carboxylic acid

2-bromo-4-(3-bromo-4-methoxyphenyl)-1-methoxybenzene

4,4'-Dihydroxybiphenyl

4'-methoxy-1,1'-biphenyl-4-ol

Refernces

• 1、 Bazgir, Ayoob,Dabiri, Minoo,Movahed, Siyavash Kazemi. "Palladium nanoparticle decorated high nitrogen-doped graphene with high catalytic activity for Suzuki–Miyaura and Ullmann-type coupling reactions in aqueous media". . p. 265 - 274. Retrieved 2014.
• 2、 Lu, Feng. "Vanadium(IV) tetrachloride catalyzed oxidative homo-coupling of aryl lithium under mild reaction condition". . p. 2444 - 2446. Retrieved 2012.
• 3、 Ding, Nini,Zhang, Jun,Hor, T. S. Andy. "Formation and crystallographic elucidation of stable [4 + 2]-coordinate nickel(ii) N,S-heterocyclic carbene (NSHC) complexes". . p. 1853 - 1858. Retrieved 2009.
• 4、 Kitazawa, Yu,Otsuka, Mai,Kanazawa, Junichiro,Takita, Ryo,Uchiyama, Masanobu. "Palladium-Catalyzed Cross-Coupling Reaction of Lithiated Monocarba- closo -dodecaborate at the Carbon Vertex". . p. 2403 - 2407. Retrieved 2015.
• 5、 Courtois, Valerie,Barhdadi, Rachid,Condon, Sylvie,Troupel, Michel. "Catalysis by nickel-2,2'-dipyridylamine complexes of the electroreductive coupling of aromatic halides in ethanol". . p. 5993 - 5996. Retrieved 1999.
• 6、 Benmansour, Hadjar,Chambers, Richard D.,Sandford, Graham,Batsanov, Andrei S.,Howard, Judith A.K.. "Polyhalogenoheterocyclic compounds. Part 54: [1] Suzuki reactions of 2,4,6-tribromo-3,5-difluoropyridine". . p. 718 - 722. Retrieved 2007.
• 7、 Dumbre, Deepa,Choudhary, Vasant R.,Selvakannan. "Cu–Fe layered double hydroxide derived mixed metal oxide: Environmentally benign catalyst for Ullmann coupling of aryl halides". . p. 180 - 184. Retrieved 2016.
• 8、 Li, George Y.. "The first phosphine oxide ligand precursors for transition metal catalyzed cross-coupling reactions: C-C, C-N, and C-S bond formation on unactivated aryl chlorides". . p. 1513 - 1516. Retrieved 2001.
• 9、 Lv, Dan,Zhang, Yan-Yan,Li, Jing-Hua. "One-pot, nickel triflate-catalysed homocoupling of aryl chlorides in the presence of metallic magnesium". . p. 397 - 399. Retrieved 2009.
• 10、 Chen, Chen,Yang, Lian-Ming. "Nickel(II)-aryl complexes as catalysts for the Suzuki cross-coupling reaction of chloroarenes and arylboronic acids". . p. 2427 - 2430. Retrieved 2007.