3389-21-7 Usage
Description
3-(2-Bromoethyl)indole is an organic compound that features an indole core with a bromoethyl group attached at the 3-position. This unique structure endows it with versatile chemical properties, making it a valuable intermediate in the synthesis of various complex organic molecules and pharmaceutical compounds.
Uses
Used in Pharmaceutical Synthesis:
3-(2-Bromoethyl)indole is used as a key intermediate in the synthesis of β-carboline derivatives, which are known for their diverse biological activities, including potential applications in the treatment of neurological disorders and as anticancer agents.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(2-Bromoethyl)indole is used as a building block for the preparation of 6,7-dihydro-12H-indolo[2,3-a]pyridocolinium bromide. 3-(2-BROMOETHYL)INDOLE can be further utilized in the development of novel organic materials and pharmaceuticals.
Used in Crown Ether Synthesis:
3-(2-Bromoethyl)indole is employed as a starting material for the synthesis of N-(2-(3-indolyl)ethyl)aza-crown ethers, such as N-(2-(3-Indolyl)ethyl)aza-12-crown-4, N-(2-(3-Indolyl)ethyl)aza-15-crown-5, and N-(2-(3-Indolyl)ethyl)aza-18-crown-6. These crown ethers have potential applications in supramolecular chemistry, as they can form complexes with various metal ions and organic substrates, leading to their use in sensors, catalysts, and drug delivery systems.
Overall, 3-(2-Bromoethyl)indole is a versatile chemical intermediate with applications in various industries, including pharmaceuticals, organic synthesis, and supramolecular chemistry. Its unique structure and reactivity make it a valuable component in the development of new compounds and materials with potential applications in medicine, materials science, and beyond.
Check Digit Verification of cas no
The CAS Registry Mumber 3389-21-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,3,8 and 9 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 3389-21:
(6*3)+(5*3)+(4*8)+(3*9)+(2*2)+(1*1)=97
97 % 10 = 7
So 3389-21-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H10BrN/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2
3389-21-7Relevant articles and documents
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Eryshev et al.
, (1974)
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A convenient synthesis of indole and 1,4-dihydropyridine hybrid macromolecules by dimerization of [2-(1h-indol-3-yl)ethyl]pyridinium salts
Ling, Gang,Zhang, Jing,Zhang, Rong-Zheng,Han, Fu-She
, p. 67 - 73 (2018/01/26)
The design and synthesis of a novel type of macrocyclic compounds containing indole and 1,4-dihydropyridine heterocyclic subunits is presented. The key reaction involved in the synthesis was a base-mediated dimerization of [2-(1H-indol-3-yl)ethyl]pyridinium salts. The structure of the macrocycles was unambiguously confirmed by NMR and HRMS spectroscopic and X-ray single crystal diffraction.
Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine
Tong, Shuo,Xu, Zhengren,Mamboury, Mathias,Wang, Qian,Zhu, Jieping
, p. 11809 - 11812 (2015/10/05)
Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxy, and amino groups were tolerated. From β,β-disubstituted o-nitrostyrenes, 2,3-disubstituted indoles were formed by a domino reduction/cyclization/migration process. Mild conditions, simple experimental procedure, ready accessibility of the starting materials and good to excellent yields characterize the present transformation. The methodology was used as a key step in a concise synthesis of rizatriptan and a formal total synthesis of aspidospermidine. Mild and efficient treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-Hamination process. A concise synthesis of a marketed drug (rizatriptan) and a formal total synthesis of aspidospermidine featuring this novel N-heterocyclization process are reported.
