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4-Iodobenzoylacetonitrile is a chemical compound characterized by its molecular formula C10H6INO and a molecular weight of 293.06 g/mol. It presents as a yellow solid with a melting point ranging from 113-116 °C. 4-Iodobenzoylacetonitrile is recognized for its reactivity and is predominantly utilized in the synthesis of pharmaceuticals and organic compounds, serving as an intermediate in the production of a variety of organic chemicals.

206346-33-0

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206346-33-0 Usage

Uses

Used in Pharmaceutical Synthesis:
4-Iodobenzoylacetonitrile is used as a key intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and medicinal compounds. Its reactivity allows for the creation of diverse chemical entities that can be further processed into therapeutic agents.
Used in Organic Compounds Synthesis:
In the realm of organic chemistry, 4-Iodobenzoylacetonitrile serves as a versatile precursor for the preparation of a wide array of organic compounds. Its unique structure and reactivity make it a valuable component in the synthesis of complex organic molecules.
Used in Chemical Production:
4-Iodobenzoylacetonitrile is employed as an intermediate in the production of various organic chemicals, playing a crucial role in the manufacturing process of different chemical products. Its presence in these processes is essential for achieving the desired chemical outcomes and final products.

Check Digit Verification of cas no

The CAS Registry Mumber 206346-33-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,6,3,4 and 6 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 206346-33:
(8*2)+(7*0)+(6*6)+(5*3)+(4*4)+(3*6)+(2*3)+(1*3)=110
110 % 10 = 0
So 206346-33-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H6INO/c10-8-3-1-7(2-4-8)9(12)5-6-11/h1-4H,5H2

206346-33-0Relevant articles and documents

Cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from N-allyl enamines

Zhai, Sheng-Xian,Dong, Hong-Ru,Chen, Zi-Bao,Hu, Yi-Ming,Dong, Heng-Shan

, p. 8405 - 8412 (2014)

An efficient iodine-mediated cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from easily prepared N-allyl enamines has been developed. The advantages of the reaction include facilitative preparation of substrates 3a-t, good functional group tolerance and transition-metal-free conditions.

Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles

Zeng, Ge,Liu, Jichao,Shao, Yinlin,Zhang, Fangjun,Chen, Zhongyan,Lv, Ningning,Chen, Jiuxi,Li, Renhao

, p. 861 - 867 (2021/01/09)

A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures.

Synthesis and Structure-Activity Relationship of Dual-Stage Antimalarial Pyrazolo[3,4- b]pyridines

Eagon, Scott,Hammill, Jared T.,Sigal, Martina,Ahn, Kevin J.,Tryhorn, Julia E.,Koch, Grant,Belanger, Briana,Chaplan, Cory A.,Loop, Lauren,Kashtanova, Anna S.,Yniguez, Kenya,Lazaro, Horacio,Wilkinson, Steven P.,Rice, Amy L.,Falade, Mofolusho O.,Takahashi, Rei,Kim, Katie,Cheung, Ashley,Dibernardo, Celine,Kimball, Joshua J.,Winzeler, Elizabeth A.,Eribez, Korina,Mittal, Nimisha,Gamo, Francisco-Javier,Crespo, Benigno,Churchyard, Alisje,García-Barbazán, Irene,Baum, Jake,Anderson, Marc O.,Laleu, Beno?t,Guy, R. Kiplin

, p. 11902 - 11919 (2020/11/26)

Malaria remains one of the most deadly infectious diseases, causing hundreds of thousands of deaths each year, primarily in young children and pregnant mothers. Here, we report the discovery and derivatization of a series of pyrazolo[3,4-b]pyridines targeting Plasmodium falciparum, the deadliest species of the malaria parasite. Hit compounds in this series display sub-micromolar in vitro activity against the intraerythrocytic stage of the parasite as well as little to no toxicity against the human fibroblast BJ and liver HepG2 cell lines. In addition, our hit compounds show good activity against the liver stage of the parasite but little activity against the gametocyte stage. Parasitological profiles, including rate of killing, docking, and molecular dynamics studies, suggest that our compounds may target the Qo binding site of cytochrome bc1.

Novel Pyrazolo[1,5-a]pyrimidines as Translocator Protein 18 kDa (TSPO) Ligands: Synthesis, in Vitro Biological Evaluation, [18F]-Labeling, and in Vivo Neuroinflammation PET Images

Damont, Annelaure,Médran-Navarrete, Vincent,Cacheux, Fanny,Kuhnast, Bertrand,Pottier, Géraldine,Bernards, Nicholas,Marguet, Frank,Puech, Frédéric,Boisgard, Rapha?l,Dollé, Frédéric

, p. 7449 - 7464 (2015/10/05)

A series of novel pyrazolo[1,5-a]pyrimidines, closely related to N,N-diethyl-2-(2-(4-(2-fluoroethoxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide (2, DPA-714), were synthesized and biologically in vitro evaluated for their potential to bind

Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers

Shen, Hang,Li, Jiaqiang,Liu, Qing,Pan, Jing,Huang, Ruofeng,Xiong, Yan

, p. 7212 - 7218 (2015/07/28)

An efficient method to synthesize β-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3·Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.

Preparation and evaluation of novel pyrazolo[1,5-a]pyrimidine acetamides, closely related to DPA-714, as potent ligands for imaging the TSPO 18 kDa with PET

Médran-Navarrete, Vincent,Damont, Annelaure,Peyronneau, Marie-Anne,Kuhnast, Bertrand,Bernards, Nicholas,Pottier, Géraldine,Marguet, Frank,Puech, Frédéric,Boisgard, Rapha?l,Dollé, Frédéric

, p. 1550 - 1556 (2014/03/21)

A series of four novel analogues of DPA-714, bearing a fluoroalkynyl side chain (with a length ranging from three to six carbon atoms) in replacement of the fluoroethoxy motif, have been synthetized in six steps from commercially available methyl 4-iodobe

Analogs of JHU75528, a PET ligand for imaging of cerebral cannabinoid receptors (CB1): Development of ligands with optimized lipophilicity and binding affinity

Fan, Hong,Kotsikorou, Evangelia,Hoffman, Alexander F.,Ravert, Hayden T.,Holt, Daniel,Hurst, Dow P.,Lupica, Carl R.,Reggio, Patricia H.,Dannals, Robert F.,Horti, Andrew G.

experimental part, p. 593 - 608 (2009/09/08)

Cyano analogs of Rimonabant with high binding affinity for the cerebral cannabinoid receptor (CB1) and with optimized lipophilicity have been synthesized as potential positron emission tomography (PET) ligands. The best ligands of the series are optimal t

Discovery of S-[5-amino-1-(4-fluorophenyl)-1H-pyrazol-4-yl]-[3-(2,3- dihydroxypropoxy)phenyl]-methanone (RO3201195), an orally bioavailable and highly selective inhibitor of p38 Map kinase

Goldstein, David M.,Alfredson, Tom,Bertrand, Jay,Browner, Michelle F.,Clifford, Ken,Dalrymple, Stacie A.,Dunn, James,Freire-Moar, Jose,Harris, Seth,Labadie, Sharada S.,La Fargue, JoAnn,Lapierre, Jean Marc,Larrabee, Susan,Li, Fujun,Papp, Eva,McWeeney, Daniel,Ramesha, Chakk,Roberts, Rick,Rotstein, David,San Pablo, Bong,Sjogren, Eric B.,So, On-Yee,Talamas, Francisco X.,Tao, Will,Trejo, Alejandra,Villasenor, Armando,Welch, Mary,Welch, Teresa,Weller, Paul,Whiteley, Phyllis E.,Young, Kelly,Zipfel, Sheila

, p. 1562 - 1575 (2007/10/03)

A novel class of highly selective inhibitors of p38 MAP kinase was discovered from high throughput screening. The synthesis and optimization of a series of 5-amino-N-phenyl-1H-pyrazol-4-yl-3-phenylmethanones is described. An X-ray crystal structure of this series bound in the ATP binding pocket of unphosphorylated p38a established the presence of a unique hydrogen bond between the exocyclic amine of the inhibitor and threonine 106 which likely contributes to the selectivity for p38. The crystallographic information was used to optimize the potency and physicochemical properties of the series. The incorporation of the 2,3-dihydroxypropoxy moiety on the pyrazole scaffold resulted in a compound with excellent drug-like properties including high oral bioavailability. These efforts identified 63 (RO3201195) as an orally bioavailable and highly selective inhibitor of p38 which was selected for advancement into Phase I clinical trials.

Allosteric modulation of the adenosine A1 receptor. Synthesis and biological evaluation of novel 2-amino-3-benzoylthiophenes as allosteric enhancers of agonist binding

Van Der Klein, Pieter A. M.,Kourounakis, Angeliki P.,IJzerman, Ad P.

, p. 3629 - 3635 (2007/10/03)

Novel allosteric enhancers of agonist binding to the rat adenosine A1 receptor are described. The lead compound for the new series was PD 81,723 ((2-amino-4,5-dimethyl-3-thienyl)[3-(trifluoromethyl)phenyl]methanone), a compound previously reported by Bruns and co-workers (Mol. Pharmacol. 1990, 38, 950-958). The 4,5-dimethyl group and the benzoyl moiety were targets for further modifications, leading to series of 4,5-dialkyl (12a-g), of tetrahydrobenzo (12h-u), and of tetrahydropyridine (13a-g) derivatives. A number of compounds, in particular 12b, 12e, 12j, 12n, and 12u, proved superior to PD 81,723. Their EC50 values for enhancing the binding of the adenosine A1 receptor agonist N6-cyclopentyladenosine to the receptor were lower, and/or their antagonistic activity on the adenosine A1 receptor was shown to be diminished.

Solid-phase C-acylation of active methylene compounds

Sim, Mui Mui,Lee, Cheng Leng,Ganesan

, p. 2195 - 2198 (2007/10/03)

Active methylene compounds were attached to the Wang resin by an ester linkage. C-acylation was achieved with a reactive species generated in sire by the combination of a carboxylic acid, diethyl phosphorocyanidate, and triethylamine. Cleavage from the resin with simultaneous decarboxylation gave the products in moderate to good yield.

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