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942-01-8 - 1,2,3,4-Tetrahydrocarbazole, 99% - B23657 - Alfa Aesar

B23657 1,2,3,4-Tetrahydrocarbazole, 99%

CAS Number
942-01-8
Synonyms

Size Price ($) Quantity Availability
25g 38.60
100g 103.00
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1,2,3,4-Tetrahydrocarbazole, 99%

MDL
MFCD00004959
EINECS
213-385-7

Chemical Properties

Formula
C12H13N
Formula Weight
171.24
Melting point
118-120°
Boiling Point
325-330°
Solubility
Insoluble in water. Solubility in methanol (almost transparency).

Applications

It finds its application as a pharmaceutical intermediate and in the synthesis of aspidospermidine alkaloids.

Notes

Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

Crosby U. Rogers and B. B. Corson. One-Step Synthesis of 1,2,3,4-Tetrahydrocarbazole and 1,2-Benzo-3,4-dihydrocarbazole.J. Am. Chem. Soc.,1947,69(11), 2910-2911.

Anahí Urrutia, et. al. Synthesis of aspidospermidine alkaloids from 1,2,3,4-tetrahydrocarbazole: Total stereoselective synthesis of (±)-18-noraspidospermidine.Tetrahedron.,2014,55(36), 11095-11108.

Deprotonation with excess superbasic n-BuLi/KO-t-Bu to give the N,ɑ-dianion has been studied in a variety of ether solvents. Formation of substantial amounts of the ɑ-ethyl derivative was observed with Et2O and THF, and also, remarkably, with various alkyl methyl ethers; e.g. in n-BuOMe, the ɑ-ethyl product was obtained in 60% yield. The ethyl group originates from the interaction of the solvent with the strong base, confirmed by the detection of ethylene in the absence of the tetrahydrocarbazole substrate: J. Org. Chem., 60, 8334 (1995). ɑ-Ethylation also occurred with 2-ethylindole, but not with 2-methyl- or 2-isopropyl analogues.

Photooxygenation with singlet oxygen, followed by reduction of the expected hydroperoxide to the allylic alcohol, is accompanied by ring contraction to a spiro ketone. The same product is formed in high yield on treatment of the spiroketone with mineral acid: J. Org. Chem., 61, 810 (1996):

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335-H303

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May be harmful if swallowed.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
133771
Harmonized Tariff Code
2933.99
TSCA
No
RTECS
FE6300000

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