253-66-7 Usage
Description
Cinnoline, also known as 1,2-diaza-naphthalene, is an azaarene that serves as the parent compound for the class of cinnolines. It is a heterocyclic aromatic compound with a unique structure that features a 1,2-diaza analogue of naphthalene.
Uses
Used in Pharmaceutical Industry:
Cinnoline is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a versatile building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
Cinnoline is utilized as a starting material in the synthesis of a wide range of organic compounds, including dyes, pigments, and other specialty chemicals. Its reactivity and stability contribute to its usefulness in various chemical reactions.
Used in Research and Development:
Cinnoline serves as a valuable research tool in the study of heterocyclic chemistry and the development of new synthetic methods. Its unique properties and reactivity make it an interesting target for exploration in academic and industrial research settings.
Purification Methods
It is distilled at high vacuum, then recrystallised from pet ether. Keep it under N2 in sealed tubes in the dark at 0o. The hydrochloride [5949-24-6] M 166.6 crystallises from EtOH/Et2O and has m 156-158o (yellow monohydrate), and dehydrates on sublimation at 110-115o/3mm. The picrate has m 196-196.5o. [Beilstein 23 H 173, 23 III.IV 1217.]
Check Digit Verification of cas no
The CAS Registry Mumber 253-66-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,5 and 3 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 253-66:
(5*2)+(4*5)+(3*3)+(2*6)+(1*6)=57
57 % 10 = 7
So 253-66-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H6N2/c1-2-4-8-7(3-1)5-6-9-10-8/h1-6H
253-66-7Relevant articles and documents
Formation of Bicyclic Azepines by Intramolecular Trapping of Didehydroazepines
Murata, Shigeru,Miwa, Masaki,Tomioka, Hideo
, p. 1255 - 1256 (1995)
Photolysis of 2-(3-aminopropyl)phenyl azides 6 gives 2,3,4,4a-tetrahydro-1H-pyridoazepines 7 in good yields, which are formed by intramolecular trapping of the ring-expanded didehydroazepine intermediate with an amino group.
SUBSTITUTED ALKYLAMINE DERIVATIVES AND METHODS OF USE
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, (2008/06/13)
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Cyclization of 1-(2-alkynylphenyl)-3,3-dialkyltriazenes: A convenient, high-yield synthesis of substituted cinnolines and isoindazoles
Kimball, David B.,Weakley, Timothy J. R.,Haley, Michael M.
, p. 6395 - 6405 (2007/10/03)
A new route to isoindazoles and cinnolines through the cyclization of (2-alkynylphenyl)triazenes under neutral conditions is presented. The products that result from heating the starting triazenes depend on both the type of alkyne ortho to the triazene functionality and the temperature used. Butadiyne moieties ortho to dialkyltriazenes yield bis-isoindazole dimers when heated to 150 °C in MeI. A requirement for cyclization in MeI is that the (2-alkynylphenyl)triazene must contain a suitably electron-withdrawing substituent on the phenyl ring to deactivate the triazene toward methylation-induced decomposition to an iodoarene. Ethynyl moieties ortho to dialkyltriazenes yield both isoindazole dimers as well as 3-formylisoindazoles when subjected to the same conditions. Replacing MeI with 1,2-dichlorobenzene as solvent allows for the general cyclization of (2-ethynylphenyl)dialkyltriazenes. Heating to 170 °C results in a mixture of isoindazole and cinnoline products, whereas the cinnolines are produced exclusively in high yield at 200 °C. Alternatively, the isoindazoles can be obtained in good to excellent yield by stirring a 1,2-dichloroethane solution of the starting triazene with CuCl overnight at 50 °C.
