Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 6
Submit an article Journal homepage
577
Views
54
CrossRef citations to date
0
Altmetric
Original Articles

Regio-selective Mono Nitration of Phenols with Ferric Nitrate in Room Temperature Ionic Liquid

R. Rajagopal Division of Organic Chemistry: Technology, National Chemical Laboratory, Pune, Maharashtra, India
&
K. V. Srinivasan Division of Organic Chemistry: Technology, National Chemical Laboratory, Pune, Maharashtra, IndiaCorrespondence[email protected]
Pages 961-966 | Received 17 Feb 2002, Published online: 17 Aug 2006

Citations (54)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (7)

Dandan Li, Yimeng Chen, Mengya Ma, Yanling Yu, Zhenzhen Jia, Penghui Li & Zhiyu Xie. (2019) Regioselective C5 nitration of N-protected indolines using ferric nitrate under mild conditions. Synthetic Communications 49:10, pages 1231-1240.
Read now
RajeshH. Vekariya & HiteshD. Patel. (2014) Selective Nitration of Phenolic Compounds by Green Synthetic Approaches. Synthetic Communications 44:16, pages 2313-2335.
Read now
Srinivas Pasnoori, Chinna Rajanna Kamatala, Satish Kumar Mukka & Rajendar Reddy Kancharla. (2014) Prussian Blue as an Eco-Friendly Catalyst for Selective Nitration of Organic Compounds Under Conventional and Nonconventional Conditions. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry 44:3, pages 364-370.
Read now
Firouzeh Nemati, Hossein Kiani & Yaser Saeidi Hayeniaz. (2011) Cellulose-Supported Ni(NO3)2 · 6H2O/2,4,6-Trichloro-1,3,5-triazine (TCT) as a Mild, Selective, and Biodegradable System for Nitration of Phenols. Synthetic Communications 41:20, pages 2985-2992.
Read now
Hassan Fathinejad Jirandehi & Marjan Mirzaeian. (2011) Nitration of Phenolic Compounds by Antimony Nitrate. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry 41:3, pages 284-286.
Read now
Xianghua Yang & Chanjuan Xi. (2007) Ce(SO4)2‐Mediated Nitration of N,N‐Dialkylanilines with NaNO2 in Water. Synthetic Communications 37:19, pages 3381-3392.
Read now
S. A. Siddiqui, R. N. Nadaf, R. Rajagopal, Thomas Daniel, R. J. Lahoti & K. V. Srinivasan. (2004) Ionic Liquid Promoted Rapid Synthesis of Aryl Hydrazones Under Ambient Conditions. Synthetic Communications 34:1, pages 41-48.
Read now

Articles from other publishers (47)

Sudhir P. Chaskar, Ramchandra Honparkhe, Jagdish Chavan, Amit Dhumal, Narendra K. Tripathy, Chinmoy Pramanik, Ashok Chaudhari, Rakesh G. Thorat & Mukund K. Gurjar. (2023) Unusual impurity formation during the process development of Olsalazine sodium leads to a new efficient and economical synthesis of tricaine mesylate. Journal of Heterocyclic Chemistry 60:8, pages 1464-1473.
Crossref
Alexandr K. Kharchenko, Ruslan V. Fauziev, Mikhail N. Zharkov, Ilya V. Kuchurov & Sergei G. Zlotin. (2021) Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium. RSC Advances 11:42, pages 25841-25847.
Crossref
Jian-Wei Wu, Pu Zhang & Zhi-Xin Guo. (2021) Nitration of deactivated aromatic compounds via mechanochemical reaction. Tetrahedron Letters 72, pages 153087.
Crossref
Christina Kannigadu & David. D. N'Da. (2020) Recent Advances in the Synthesis and Development of Nitroaromatics as Anti-Infective Drugs. Current Pharmaceutical Design 26:36, pages 4658-4674.
Crossref
Palani Natarajan, Renu Chaudhary & Paloth Venugopalan. (2019) Ipso-nitration of carboxylic acids using a mixture of nitronium tetrafluoroborate, base and 1-hexyl-3,4,5-trimethyl-1H-imidazolium tetrafluoroborate. Tetrahedron Letters 60:26, pages 1720-1723.
Crossref
Feng-Chao Guo, Min-Zun Ji, Pu Zhang & Zhi-Xin Guo. (2018) Facile nitration of aromatic compounds using Bi(NO3)3·5H2O/MgSO4 under mechanochemical conditions. Green Processing and Synthesis 7:5, pages 453-459.
Crossref
Ilya V. Kuchurov, Mikhail N. Zharkov, Leonid L. Fershtat, Nina N. Makhova & Sergey G. Zlotin. (2017) Prospective Symbiosis of Green Chemistry and Energetic Materials. ChemSusChem 10:20, pages 3914-3946.
Crossref
Hemchandra K. Chaudhari, Akshata Pahelkar & Balaram S. Takale. (2017) Preparative-scale synthesis of amino coumarins through new sequential nitration and reduction protocol. Tetrahedron Letters 58:43, pages 4107-4110.
Crossref
Yu. G. Khabarov, N. Yu. Kuzyakov, V. A. Veshnyakov, G. V. Komarova & A. Yu. Garkotin. (2017) Nitration of sulfate lignin under homogeneous conditions studied by electron spectroscopy. Russian Chemical Bulletin 65:12, pages 2925-2931.
Crossref
Govind Goroba Pawar, Abhilashamole Brahmanandan & Manmohan Kapur. (2016) Palladium(II)-Catalyzed, Heteroatom-Directed, Regioselective C–H Nitration of Anilines Using Pyrimidine as a Removable Directing Group. Organic Letters 18:3, pages 448-451.
Crossref
Chandra S. Azad, Vishal M. Balaramnavar, Imran A. Khan, Pawan K. Doharey, Jitendra K. Saxena & Anil K. Saxena. (2015) Operative conversions of 3-carboxy-4-quinolones into 3-nitro-4-quinolones via ipso -nitration: potential antifilarial agents as inhibitors of Brugia malayi thymidylate kinase . RSC Advances 5:100, pages 82208-82214.
Crossref
Yu-Feng Liang, Xinyao Li, Xiaoyang Wang, Yuepeng Yan, Peng Feng & Ning Jiao. (2015) Aerobic Oxidation of Pd II to Pd IV by Active Radical Reactants: Direct C–H Nitration and Acylation of Arenes via Oxygenation Process with Molecular Oxygen . ACS Catalysis 5:3, pages 1956-1963.
Crossref
Saitanya K. Bharadwaj, Purna K. Boruah & Pradip K. Gogoi. (2014) Phosphoric acid modified montmorillonite clay: A new heterogeneous catalyst for nitration of arenes. Catalysis Communications 57, pages 124-128.
Crossref
Cun Zhang, Mei-Jing Yu, Xiao-Yu Pan, Guo Wu, Liang Jin, Wei-Dan Gao, Meng Du & Jun-Chao Zhang. (2014) Regioselective mononitration of chlorobenzene using caprolactam-based Brønsted acidic ionic liquids. Journal of Molecular Catalysis A: Chemical 383-384, pages 101-105.
Crossref
Yang Lu, Yaming Li, Rong Zhang, Kun Jin & Chunying Duan. (2013) Regioselective ortho-nitration of N-phenyl carboxamides and primary anilines using bismuth nitrate/acetic anhydride. Tetrahedron 69:45, pages 9422-9427.
Crossref
Guobing Yan & Minghua Yang. (2013) Recent advances in the synthesis of aromatic nitro compounds. Organic & Biomolecular Chemistry 11:16, pages 2554.
Crossref
Hassan Hosseini-Monfared, Hannaneh Falakian, Rahman Bikas & Peter Mayer. (2013) Intramolecular hydrogen bond effect on keto-enolization of aroylhydrazone in copper(II) complexes. Inorganica Chimica Acta 394, pages 526-534.
Crossref
Li Xia Li, Qi Long Ling, Zu Liang Liu, Xiao Dong Xing, Xiao Qin Zhu & Xiao Meng. (2012) Reusable and Efficient Polystryrene-supported Acidic Ionic Liquid Catalyst for Mononitration of Aromatic Compounds. Bulletin of the Korean Chemical Society 33:10, pages 3373-3377.
Crossref
Li Xia Li, Qi Long Ling, Xiao Dong Xing, Ye Zhang & Zu Liang Liu. (2012) Reusable and Efficient PS-Supported Acidic Ionic Liquid Catalyst for Mononitration of Toluene. Advanced Materials Research 581-582, pages 252-256.
Crossref
Hamid Goudarziafshar. (2012) A new method for the mononitration of phenol derivatives by poly(4-vinylpyridinium nitrate) and silica sulfuric acid under mild conditions. Chinese Chemical Letters 23:4, pages 458-461.
Crossref
Seung-Uk Paik & Myoung-Geun Jung. (2012) Rapid Microwave-Assisted Copper-Catalyzed Nitration of Aromatic Halides with Nitrite Salts. Bulletin of the Korean Chemical Society 33:2, pages 689-691.
Crossref
A. Sri Hari Kumar, K.T. Venkateswara Rao, K. Upendar, Ch. Sailu, N. Lingaiah & P.S. Sai Prasad. (2012) Nitration of phenol over silica supported H4PW11VO40 catalyst. Catalysis Communications 18, pages 37-40.
Crossref
Urvashi Yadav, Hemant Mande & Prasanna Ghalsasi. (2011) Nitration of Phenols Using Cu(NO 3 ) 2 : Green Chemistry Laboratory Experiment . Journal of Chemical Education 89:2, pages 268-270.
Crossref
M. Nikoorazm, A. Ghorbani-Choghamarani & H. Goudarziafshar. (2011) Supported nitric acid on polyvinylpolypyrrolidone as an efficient and mild nitrating agent for the selective preparation of nitrophenols. Scientia Iranica 18:6, pages 1353-1355.
Crossref
Jason P. Hallett & Tom Welton. (2011) Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2. Chemical Reviews 111:5, pages 3508-3576.
Crossref
Arash Ghorbani-Choghamarani, Mohsen Nikoorazm, Hamid Goudarziafshar, Zahra Naserifar & Parisa Zamani. (2011) A Mild Procedure for the Preparation of o-Nitrophenols by Nitro Urea or Ammonium Nitrate in the Presence of Silica Sulfuric Acid (SiO2-OSO3H). Chinese Journal of Chemistry 29:4, pages 731-734.
Crossref
Li Ji, Chao Qian, Mei-xin Liu & Xin-zhi Chen. (2011) Highly Efficient Nitration of Phenolic Compounds using Some Nitrates and Oxalic Acid under Solvent-Free Conditions. Journal of Chemical Research 35:2, pages 101-103.
Crossref
M. Arshadi, M. Ghiaci & A. Gil. (2010) Nitration of Phenol over a ZSM-5 Zeolite. Industrial & Engineering Chemistry Research 49:12, pages 5504-5510.
Crossref
Abdolmajid Riahi, Mohanad Shkoor, Olumide Fatunsin, Mirza A. Yawer, Ibrar Hussain, Christine Fischer & Peter Langer. (2009) Regioselective synthesis of amino- and nitroarenes based on [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes. Tetrahedron 65:45, pages 9300-9315.
Crossref
Arash Ghorbani-Choghamarani, Hamid Goudarziafshar, Mohsen Nikoorazm & Somaieh Yousefi. (2009) Aluminum nitrate and silica sulfuric acid as efficient nitrating media for the mononitration of phenols under mild and heterogeneous conditions. Canadian Journal of Chemistry 87:8, pages 1144-1147.
Crossref
Shuojin Wang, Shaojie Jiang & Jin Nie. (2009) Lanthanide Bis[(trifluoromethyl)sulfonyl]imides as Reusable Catalysts for Mononitration of Substituted Benzenes in Ionic Liquids. Advanced Synthesis & Catalysis 351:11-12, pages 1939-1945.
Crossref
Hui Zhen Zhi, Jun Luo, Guang An Feng & Chun Xu Lv. (2009) An efficient method to synthesize HMX by nitrolysis of DPT with N2O5 and a novel ionic liquid. Chinese Chemical Letters 20:4, pages 379-382.
Crossref
Shuo‐Jin WANG, Zhi‐Ying SUN & Jin NIE. (2008) Nitration of Substituted Benzenes Catalyzed by Metal Bis[(perfluoroalkyl)sulfonyl]imides in Quaternary Ammonium Ionic Liquids. Chinese Journal of Chemistry 26:12, pages 2256-2260.
Crossref
Dong Fang, Qun-Rong Shi, Jian Cheng, Kai Gong & Zu-Liang Liu. (2008) Regioselective mononitration of aromatic compounds using Brønsted acidic ionic liquids as recoverable catalysts. Applied Catalysis A: General 345:2, pages 158-163.
Crossref
Martyn Earle, Peter Wasserscheid, Peter Schulz, Héléne Olivier‐Bourbigou, Frédéric Favre, Michel Vaultier, Andreas Kirschning, Vasundhara Singh, Anders Riisager, Rasmus Fehrmann & Sven Kuhlmann. 2007. Ionic Liquids in Synthesis. Ionic Liquids in Synthesis 265 568 .
Majid M. Heravi, Tina Benmorad, Khadijeh Bakhtiari, Fatemeh F. Bamoharram & Hossein H. Oskooie. (2007) H3+xPMo12−xVxO40 (heteropolyacids)-catalyzed regioselective nitration of phenol to o-nitrophenol in heterogeneous system. Journal of Molecular Catalysis A: Chemical 264:1-2, pages 318-321.
Crossref
Nitin S. Nandurkar, Mayur J. Bhanushali, Sachin R. Jagtap & Bhalchandra M. Bhanage. (2007) Ultrasound promoted regioselective nitration of phenols using dilute nitric acid in the presence of phase transfer catalyst. Ultrasonics Sonochemistry 14:1, pages 41-45.
Crossref
G. I. Borodkin & V. G. Shubin. (2006) Electrophilic reactions of aromatic and heteroaromatic compounds in ionic liquids. Russian Journal of Organic Chemistry 42:12, pages 1745-1770.
Crossref
V. Anuradha, P.V. Srinivas, P. Aparna & J. Madhusudana Rao. (2006) p-Toluenesulfonic acid catalyzed regiospecific nitration of phenols with metal nitrates. Tetrahedron Letters 47:28, pages 4933-4935.
Crossref
M. Muthukrishnan, Shivaji V. More, Dinesh R. Garud, C. V. Ramana, R. R. Joshi & R. A. Joshi. (2009) Pictet‐spengler cyclization in room temperature ionic liquid: A convenient access to tetrahydro β‐carbolines. Journal of Heterocyclic Chemistry 43:3, pages 767-772.
Crossref
J. Jon Paul Selvam, V. Suresh, K. Rajesh, S. Ravinder Reddy & Y. Venkateswarlu. (2006) Highly efficient nitration of phenolic compounds by zirconyl nitrate. Tetrahedron Letters 47:15, pages 2507-2509.
Crossref
Keith Smith, Shifang Liu & Gamal A. El-Hiti. (2005) Regioselective Mononitration of Simple Aromatic Compounds under Mild Conditions in Ionic Liquids. Industrial & Engineering Chemistry Research 44:23, pages 8611-8615.
Crossref
Hong-Bin Sun, Ruimao Hua & Yingwu Yin. (2005) Highly Efficient Nitration of Phenolic Compounds in Solid Phase or Solution Using Bi(NO 3 ) 3 ·5H 2 O as Nitrating Reagent . The Journal of Organic Chemistry 70:22, pages 9071-9073.
Crossref
Emilie Dal & N. Llewellyn Lancaster. (2005) Acetyl nitrate nitrations in [bmpy][N(Tf)2] and [bmpy][OTf], and the recycling of ionic liquids. Organic & Biomolecular Chemistry 3:4, pages 682.
Crossref
J.L. Chiara. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 709 852 .
Sanjay S. Palimkar, Shapi A. Siddiqui, Thomas Daniel, Rajgopal. J. Lahoti & Kumar V. Srinivasan. (2003) Ionic Liquid-Promoted Regiospecific Friedlander Annulation:  Novel Synthesis of Quinolines and Fused Polycyclic Quinolines. The Journal of Organic Chemistry 68:24, pages 9371-9378.
Crossref
R. Rajagopal & K. V. Srinivasan. (2003) Regio‐Selective Mono Nitration of Phenols with Ferric Nitrate in Room Temperature Ionic Liquid.. ChemInform 34:31.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.