274-40-8 Usage
Description
Indolizine is a nitrogen-containing bicyclic aromatic compound with a unique fused-ring structure consisting of a six-membered pyridine ring and a five-membered pyrrole ring. It is known for its versatile chemical properties and potential applications in various fields due to its stability, which can be further enhanced by the presence of substituents, particularly aryl groups at the C2and C5-positions.
Uses
Used in Pharmaceutical Industry:
Indolizine is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and basicity make it a valuable building block in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
Indolizine serves as a key intermediate in the synthesis of a wide range of organic compounds, including natural products, agrochemicals, and other specialty chemicals. Its reactivity and stability make it an attractive candidate for use in various chemical reactions and processes.
Used in Material Science:
The unique properties of indolizine, such as its low melting point or high boiling point, sensitivity to light and air, and steam volatility, make it a potential candidate for use in the development of new materials with specific characteristics, such as light-sensitive materials or materials with tailored volatility properties.
Chemical Reactivity
Indolizines are chemically quite reactive and readily undergo electrophilic substitution reactions similar to indole
and isoindoles but show resistance to nucleophilic substitution reactions. The preferential site for electrophilic substitution
is C3 but may also take place at C1 as evident from the resonating structures. It is resistant to acid-catalyzed
polymerization. As regards protonation of indolizine it is protonated preferentially at C3 but in the case of the preoccupied
C3-position by an electron-donating substituent, protonation takes place at C1.
Synthesis Reference(s)
Journal of the American Chemical Society, 81, p. 1456, 1959 DOI: 10.1021/ja01515a044The Journal of Organic Chemistry, 22, p. 589, 1957 DOI: 10.1021/jo01356a621
Purification Methods
Purify indolizine through an alumina column in *C6H6 and elute with *C6H6 (toluene could be used instead). The eluate contained in the fluorescent band (using UV light 365mn) is collected, evaporated and the crystalline residue is sublimed twice at 40-50o/0.2-0.5mm. The colourless crystals darken on standing and should be stored in dark sealed containers. If the original sample is dark in color then it should be covered with water and steam distilled. The colourless crystals in the distillate are collected and dried between filter paper and sublimed. It protonates on C3 in aqueous acid. It should give one fluorescent spot on paper chromatography (Whatman 1) in 3% aqueous ammonia and in n-BuOH/AcOH/H2O (4:1:1). The picrate has m 101o from EtOH. [Armarego J Chem Soc 226 1964, Armarego J Chem Soc (B) 191 1966, Scholtz Chem Ber 45 734 1912, Beilstein 20 II 200, 20 III/IV 3195.]
Check Digit Verification of cas no
The CAS Registry Mumber 274-40-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,7 and 4 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 274-40:
(5*2)+(4*7)+(3*4)+(2*4)+(1*0)=58
58 % 10 = 8
So 274-40-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H7N/c1-2-6-9-7-3-5-8(9)4-1/h1-7H
274-40-8Relevant articles and documents
Chemistry of α-Amino Nitriles. Exploratory Experiments on Thermal Reactions of α-Amino Nitriles
Xiang, Yi-Bin,Drenkard, Susanne,Baumann, Karl,Hickey, Deirdre,Eschenmoser, Albert
, p. 2209 - 2250 (2007/10/02)
The paper extends a previously published report on chemical properties of α-amino nitriles and of members of the C3H4N2 ensemble (Scheme 1) as observed in experiments carried out under non-aqueous conditions.The reactions investigated and the observations made are summarized in some detail in the English footnotes (*) referring to Schemes 1-17 and Fig. 1.
REACTIONS OF NITROGEN CONTAINING AROMATIC ANIONS WITH CHLOROCARBENE
Burger, U.,Dreier, F.
, p. 2065 - 2072 (2007/10/02)
It is shown that the 4-azapentalene anion (1) and the dipyrroloimidazolyl anion (2) (Li salts) undergo eliminative ring fission upon reaction with chlorocarbene in tetrahydrofuran.Acetylenes (12 and 18) are the result.The reaction of 1 is accompanied by ring enlargement to indolizine (7).When the reaction of 1 with chlorocarbene is performed in diethylether, again 7 is produced, this time accompanied by a tetracyclic valence isomer, the pyrroloazabenzvalene (8).Mechanistic implications, based on the finding that the site of label incorporation in the enlarged products is solvent dependent, are discussed and compared with the corresponding reactions of carboaromatic anions.Use of intramolecular oxidative coupling for the synthesis of new pyrrolo annellated heterocyclic systems is made throughout this work.
