Organic Chemicals

4,4'-DINITROBIPHENYL

  • Chemical Name: 4,4'-DINITROBIPHENYL
  • CAS: 1528-74-1
  • Purity: 99%
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  • Molecular Formula: C12H8 N2 O4
  • Molecular Weight: 244.207
  • Melting Point: 242°C 
  • Refractive Index: 1.6360 (estimate) 
  • Boiling Point: 418.1 °C at 760 mmHg 
  • Flash Point: 208.8 °C 
  • PSA: 91.64000 
  • Density: 1.368 g/cm3 
  • LogP: 4.21640 

1528-74-1 Relevant articles

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An iminophosphine-palladium complex has ...

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Newkome,Taylor

, p. 1362 (1979)

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The immobilization of copper(II) in orga...

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In this study, we have presented a new c...

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Water-dispersible sulfonated graphene (s...

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Band Gap Modification of TiO2 Nanoparticles by Ascorbic Acid-Stabilized Pd Nanoparticles for Photocatalytic Suzuki–Miyaura and Ullmann Coupling Reactions

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In this study, synthesis, characterizati...

An effective and environment-friendly system for Cu NPs@RGO-catalyzed C-C homocoupling of aryl halides or arylboronic acids in ionic liquids under microwave irradiation

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, p. 41108 - 41113 (2016)

As an outstanding mesh catalyst support,...

Direct homocoupling of aryl halides catalyzed by palladium

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, p. 2559 - 2560 (1998)

Symmetrical functionnalized biaryls are ...

PdAu alloy nanoparticles supported on nitrogen-doped carbon black as highly active catalysts for Ullmann coupling and nitrophenol hydrogenation reactions

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Noble metal-based catalysts have been pr...

Synthesis of gold nanoparticles decorated on sulfonated three-dimensional graphene nanocomposite and application as a highly efficient and recyclable heterogeneous catalyst for Ullmann homocoupling of aryl iodides and reduction of p-nitrophenol

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Gold nanoparticles were decorated onto s...

Palladium-catalyzed arylation of α,α-difluoro-allylic-β-hydroxyester

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The aryl-substituted α,α-difluoro-allyli...

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, p. 12005 - 12007 (2012)

The Au25(SR)18/CeO2 nanocluster catalyst...

Thiazole-based non-symmetric NNC-palladium pincer complexes as catalytic precursors for the Suzuki-Miyaura C-C coupling

Camacho-Espinoza, Martín,Reyes-Deloso, Alberto,Toscano, R. Alfredo,Penieres-Carrillo, J. Guillermo,López-Cortés, José G.,Ortega-Alfaro, M. Carmen,Ortega-Jiménez, Fernando

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We report an efficient synthesis of new ...

DEDIAZONIATION OF ARENEDIAZONIUM SALT WITH TRIVALENT PHOSPHORUS COMPOUNDS BY ONE-ELECTRON TRANSFER MECHANISM

Yasui, Shinro,Fujii, Masayuki,Kawano, Chihiro,Nishimura, Yukihiro,Ohno, Atsuyoshi

, p. 5601 - 5604 (1991)

Trivalent phosphorus compounds, tripheny...

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Schultz

, (1874)

-

-

Davey,Latter

, p. 264 (1948)

-

Highly water-dispersible magnetite-supported Pd nanoparticles and single atoms as excellent catalysts for Suzuki and hydrogenation reactions

Guarnizo,Angurell,Muller,Llorca,Seco,Rossell,Rossell

, p. 68675 - 68684 (2016)

The molecule 4-(diphenylphosphino)benzoi...

Tandem intramolecular silylformylation and silicon-assisted cross-coupling reactions. Synthesis of geometrically defined α,β-unsaturated aldehydes

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, p. 5153 - 5159 (2003)

The palladium- and copper-catalyzed cros...

RHODIUM CATALYZED REDUCTION OF ARYL IODIDES WITH A MODEL OF NAD(P)H

Yasui, Shinro,Nakamura, Kaoru,Ohno, Atsuyoshi

, p. 377 - 378 (1984)

Aryl iodides are reduced to the correspo...

Recyclable and reusable Pd(OAc)2/PPh3/PEG-2000 system for homocoupling reaction of arylboronic acids under air without base

Xia, Jianhui,Cheng, Mingzhu,Chen, Qiurong,Cai, Mingzhong

, p. 113 - 116 (2015)

A stable and efficient Pd(OAc)2/PPh3/PEG...

A new protocol for the one-pot synthesis of symmetrical biaryls

Nising, Carl F.,Schmid, Ulrike K.,Nieger, Martin,Braese, Stefan

, p. 6830 - 6833 (2004)

Biaryls play an important role in modern...

Suzuki Coupling of Chiral 1,1′-Binaphthyl Systems - New Synthetic Routes to Functionalize the 2- and 2,2′-Positions

Schilling, Birgit,Kaufmann, Dieter E.

, p. 701 - 709 (1998)

1,1′-Binaphthyl derivatives 1-5, substit...

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Hodgson,Ward

, p. 127,128 (1947)

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Electroreductive palladium-catalysed Ullmann reactions in ionic liquids: Scope and mechanism

Pachon, Laura Duran,Elsevier, Cornells J.,Rothenberg, Gadi

, p. 1705 - 1710 (2006)

A room-temperature catalytic alternative...

Icosahedral gold-platinum alloy nanocrystals in hollow silica: A highly active and stable catalyst for Ullmann reactions

Wu, Xiaoli,Tan, Longfei,Chen, Dong,Meng, Xianwei,Tang, Fangqiong

, p. 539 - 541 (2014)

Icosahedral Au-Pt alloy nanocrystals are...

Pd/TEMPO-catalyzed electrooxidative synthesis of biaryls from arylboronic acids or arylboronic esters

Mitsudo, Koichi,Shiraga, Takuya,Kagen, Daisuke,Shi, Deqing,Becker, James Y.,Tanaka, Hideo

, p. 8384 - 8388 (2009)

A facile electrooxidative method for syn...

The β-cyclodextrin decorated with palladium nanoparticles without pretreatment: An efficient heterogeneous catalyst for biaryls synthesis

Feiz, Afsaneh,Loni, Masood,Naderi, Soheila,Bazgir, Ayoob

, (2018)

β-Cyclodextrin decorated with palladium ...

A comparative homocoupling reaction of aryl halides using monomeric orthopalladated complex of 4-methoxybenzoylmethylenetri-phenylphosphorane under conventional and microwave irradiation conditions

Hajipour, Abdol R.,Karami, Kazem,Tavakoli, Ghazal

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The activity of [Pd(C6H4CH2NH 2-K2-C-N)P...

Pd-catalyzed oxidative homocoupling of arylboronic acids in aqueous ethanol at room temperature

Zhou, Zhonggao,Hu, Qiaosheng,Du, Ziyi,Xue, Jun,Zhang, Shiyong,Xie, Yongrong

, p. 940 - 943 (2012)

The authors demonstrate for the first ti...

Absolute Configuration Assignment from Optical Rotation Data by Means of Biphenyl Chiroptical Probes

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, p. 5682 - 5690 (2019)

A non-empirical approach for the assignm...

Cyclopalladated ferrocenylimine: a highly effective catalyst for the borylation/suzuki coupling reaction

Ma, Ning,Zhu, Zhiwu,Wu, Yangjie

, p. 4625 - 4629 (2007)

The cyclopalladated ferrocenylimine was ...

Synthesis of DMF-protected Au NPs with different size distributions and their catalytic performance in the Ullmann homocoupling of aryl iodides

Yao, Wang,Gong, Wei-Jie,Li, Hong-Xi,Li, Fei-Long,Gao, Jun,Lang, Jian-Ping

, p. 15752 - 15759 (2014)

DMF-stabilized Au nanoparticles (NPs) wi...

Investigation of the catalytic activity of a Pd/biphenyl-based phosphine system in the Ullmann homocoupling of aryl bromides

Nadri, Shirin,Azadi, Ehsan,Ataei, Ali,Joshaghani, Mohammad,Rafiee, Ezzat

, p. 2966 - 2970 (2011)

We described Ullmann homocoupling promot...

A Bio-Inspired Magnetically Recoverable Palladium Nanocatalyst for the Ullmann Coupling reaction of Aryl halides and Arylboronic acids In Aqueous Media

Dubey, Abhishek V.,Kumar, A. Vijay

, (2020)

Palladium nanoparticles supported on pol...

Microwave assisted efficient protocol for the classic Ullmann homocoupling reaction using Cu-Mg-Al hydrotalcite catalysts

Narasimharao, Katabathini,Al-Sabban, Ebtisam,Saleh, Tamer S.,Gallastegui, Ainara Garcia,Sanfiz, Almudena Celaya,Basahel, Sulaiman,Al-Thabaiti, Shaeel,Alyoubi, Abdulrahman,Obaid, Abdullah,Mokhtar, Mohamed

, p. 152 - 162 (2013)

Four hydrotalcite catalysts containing d...

One-pot two-step stannylation/Stille homocoupling of aryl bromides and iodides under solvent-free conditions

Gribanov, Pavel S.,Golenko, Yulia D.,Topchiy, Maxim A.,Philippova, Anna N.,Kirilenko, Nikita Yu.,Krivoshchapov, Nikolai V.,Sterligov, Grigorii K.,Asachenko, Andrey F.,Bermeshev, Maxim V.,Nechaev, Mikhail S.

, p. 323 - 325 (2018)

A new highly efficient solvent-free meth...

Electrooxidative homo-coupling of arylboronic acids catalyzed by electrogenerated cationic palladium catalysts

Mitsudo, Koichi,Shiraga, Takuya,Tanaka, Hideo

, p. 6593 - 6595 (2008)

An electrochemical method for generating...

Catalytic specificity of linear polystyrene-stabilized Pd nanoparticles during Ullmann coupling reaction in water and the associated mechanism

Ohtaka, Atsushi,Sakon, Akira,Yasui, Asuka,Kawaguchi, Taira,Hamasaka, Go,Uozumi, Yasuhiro,Shinagawa, Tsutomu,Shimomura, Osamu,Nomura, Ry?ki

, p. 87 - 93 (2018)

In the present work, heterogeneous Pd na...

Facile construction of symmetric biaryls using (BeDABCO)2Pd2Cl6 as an efficient and highly active catalyst under microwave irradiation

Hajipour, Abdol Reza,Rafiee, Fatemeh

, p. 147 - 151 (2015)

An efficient catalytic system using (BeD...

High thermal stability and rigid rod of novel organosoluble polyimides and polyamides based on bulky and noncoplanar naphthalene-biphenyldiamine

Liaw, Der-Jang,Chang, Feng-Chyuan,Leung, Man-Kit,Chou, Meng-Yen,Muellen, Klaus

, p. 4024 - 4029 (2005)

The synthesis of a naphthalene-substitut...

PALLADIUM CATALYZED REACTION OF HEXABUTYLDITIN WITH ARYL BROMIDES: PREPARATION OF NEGATIVELY SUBSITUTED ARYLTRIBUTYLTIN

Kosugi, Masanori,Shimizu, Kohji,Ohtani, Atsushi,Migita, Toshihiko

, p. 829 - 830 (1981)

Reaction of hexabutylditin with aryl bro...

Triazoliptycenes: A Twist on Iptycene Chemistry for Regioselective Cross-Coupling to Build Nonstacking Fluorophores

Kang, Taewon,Kim, Hongsik,Lee, Dongwhan

, p. 6380 - 6383 (2017)

Triazoliptycene fluorophores have been d...

Homocoupling of aryl halides promoted by tetrabutylammonium fluoride

Albanese, Domenico,Landini, Dario,Penso, Michele,Petricci, Silvia

, p. 199 - 200 (1999)

The palladium-catalysed homocoupling of ...

Palladium and copper-catalyzed ligand-free coupling of phenylhydrazines in water

Chauhan, Parul,Ravi, Makthala,Singh, Shikha,Raju, Kanumuri S. R.,Bajpai, Vikas,Kumar, Brijesh,Wahajuddin,Yadav, Prem. P.

, p. 43336 - 43340 (2014)

An efficient protocol has been developed...

Zeolite-assisted nitration of biphenyl using nitric acid

Tai, Yanfang,Peng, Xinhua,Shi, Chunjie,Dong, Xiongzi

, p. 867 - 872 (2015)

The nitration process using 95 % nitric ...

Efficient and high turnover homocoupling reaction of aryl iodide by the use of palladacycle catalyst. A convenient way to prepare poly-p-phenylene

Luo, Fen-Tair,Jeevanandam, Arumugasamy,Basu, Manas Kumar

, p. 7939 - 7942 (1998)

Monoiodoarenes undergo reductive couplin...

Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide

Ojha, Subhadra,Panda, Niranjan

supporting information, p. 1292 - 1298 (2022/02/19)

A novel Pd-catalyzed protocol for the de...

Palladium-catalyzed aryl group transfer from triarylphosphines to arylboronic acids

Enright, Dale R.,Gogate, Akash R.,Smoliakova, Irina P.,Vasireddy, Purna C. R.

, (2021/11/11)

A study of Pd-catalyzed arylation of ary...

Porphyrin n-pincer pd(Ii)-complexes in water: A base-free and nature-inspired protocol for the oxidative self-coupling of potassium aryltrifluoroborates in open-air

Hanafiah, Marlia M.,Lakkaboyana, Sivarama Krishna,Lakshmidevi, Jangam,Marella, Ravi Kumar,Naidu, Bandameeda Ramesh,Prasad, Sana Siva,Venkateswarlu, Katta

, (2021/09/13)

Metalloporphyrins (and porphyrins) are w...

Pd-catalyzed oxidative homocoupling of arylboronic acids in WEPA: A sustainable access to symmetrical biaryls under added base and ligand-free ambient conditions

Appa, Rama Moorthy,Lakshmidevi, Jangam,Naidu, Bandameeda Ramesh,Venkateswarlu, Katta

, (2021/01/11)

Symmetrical and unsymmetrical biaryls co...

1528-74-1 Process route

-butyl vinyl ether
111-34-2,92680-80-3

-butyl vinyl ether

para-nitrophenyl triflate
17763-80-3

para-nitrophenyl triflate

4-nitro-phenol
100-02-7,78813-13-5,89830-32-0

4-nitro-phenol

4,4'-dinitrobiphenyl
1528-74-1

4,4'-dinitrobiphenyl

bis(4-nitrophenyl)ether
101-63-3

bis(4-nitrophenyl)ether

(Z)-1-(2-butoxyethenyl)-4-nitrobenzene
97826-85-2

(Z)-1-(2-butoxyethenyl)-4-nitrobenzene

(E)-1-(2-butoxyethenyl)-4-nitrobenzene
97826-86-3

(E)-1-(2-butoxyethenyl)-4-nitrobenzene

1-(1-butoxyethenyl)-4-nitrobenzene
109125-23-7

1-(1-butoxyethenyl)-4-nitrobenzene

Conditions
Conditions Yield
With triethylamine; palladium diacetate; In N,N-dimethyl-formamide; at 95 ℃; for 18h; Product distribution; effect of lithium halides and tetrabutyl ammonium halides on cis/trans ratio, and ratio of α- and β-substitution products; var. solvents; other triflates;
4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

N,N-dimethyl-formamide
68-12-2,33513-42-7

N,N-dimethyl-formamide

4,4'-dinitrobiphenyl
1528-74-1

4,4'-dinitrobiphenyl

N,N-Dimethyl-4-nitroaniline
100-23-2

N,N-Dimethyl-4-nitroaniline

Conditions
Conditions Yield
With tetrabutylammomium bromide; triethylamine; palladium diacetate; at 115 ℃; for 72h;
17%
77%

1528-74-1 Upstream products

  • 636-98-6
    636-98-6

    p-nitrobenzene iodide

  • 92-52-4
    92-52-4

    biphenyl

  • 92-93-3
    92-93-3

    1-phenyl-4-nitrobenzene

  • 20246-81-5
    20246-81-5

    4,4'-dinitrodiphenic acid

1528-74-1 Downstream products

  • 1211-40-1
    1211-40-1

    4-amino-4'-nitrobiphenyl

  • 92-87-5
    92-87-5

    p,p'-diaminobiphenyl

  • 1591-30-6
    1591-30-6

    (1,1'-biphenyl)-4,4'-dicarbonitrile

  • 7334-13-6
    7334-13-6

    bis-(4'-nitro-biphenyl-4-yl)-diazene-N -oxide

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