69113-59-3 Usage
Description
3-Iodobenzonitrile is a halogenated aromatic nitrile characterized by the presence of an iodine atom and a nitrile group attached to a benzene ring. It is known for its standard molar enthalpy of formation, which has been determined through combustion calorimetry at a standard pressure of 0.1 MPa.
Uses
Used in Chemical Synthesis:
3-Iodobenzonitrile is utilized as a starting reagent in various chemical synthesis processes. It plays a crucial role in the synthesis of tetrachloroisophthalo-[14C]-nitrile (TCIN), a compound that may have applications in different chemical research and industrial processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Iodobenzonitrile is used as a key intermediate in the preparation of specific drug molecules. It contributes to the synthesis of 1-(3-iodophenyl)-3-2-[4-(trifluoromethyl)-1-piperidinyl]ethyl-2-imidazolidinonepiperidine derivative, a compound with potential therapeutic applications.
Used in Chiral Chemicals Production:
3-Iodobenzonitrile is also employed in the production of chiral amino acid anilide, an important class of chiral compounds that are vital in various chemical and pharmaceutical applications, including the development of enantiomerically pure drugs.
Used in Suzuki Reaction:
3-Iodobenzonitrile may be involved in the Suzuki reaction, a type of cross-coupling reaction used in organic chemistry to form carbon-carbon bonds. This reaction is widely used in the synthesis of various organic compounds, including pharmaceuticals and natural products, making 3-Iodobenzonitrile a valuable reagent in this context.
Synthesis Reference(s)
The Journal of Organic Chemistry, 55, p. 3552, 1990 DOI: 10.1021/jo00298a032
Check Digit Verification of cas no
The CAS Registry Mumber 69113-59-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,9,1,1 and 3 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 69113-59:
(7*6)+(6*9)+(5*1)+(4*1)+(3*3)+(2*5)+(1*9)=133
133 % 10 = 3
So 69113-59-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H4IN/c8-7-3-1-2-6(4-7)5-9/h1-4H
69113-59-3Relevant articles and documents
Revealing resonance effects and intramolecular dipole interactions in the positional isomers of benzonitrile-core thermally activated delayed fluorescence materials
Kukhta, Nadzeya A.,Higginbotham, Heather F.,Matulaitis, Tomas,Danos, Andrew,Bismillah, Aisha N.,Haase, Nils,Etherington, Marc K.,Yufit, Dmitry S.,McGonigal, Paul R.,Gra?ulevi?ius, Juozas Vidas,Monkman, Andrew P.
supporting information, p. 9184 - 9194 (2019/08/08)
We report on the properties of the three positional isomers of (2,7-di-tert-butyl-9,9-dimethylacridin-10(9H)-yl)benzonitrile, which are found to have comparable donor steric environments and donor-acceptor dihedral angles. An unexpected intramolecular dip
One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides
Leas, Derek A.,Dong, Yuxiang,Vennerstrom, Jonathan L.,Stack, Douglas E.
supporting information, p. 2518 - 2521 (2017/05/24)
A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.
Rapid and efficient copper-catalyzed finkelstein reaction of (hetero)aromatics under continuous-flow conditions
Chen, Mao,Ichikawa, Saki,Buchwald, Stephen L.
supporting information, p. 263 - 266 (2015/02/05)
A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.
