T12408
1,2,3,4-Tetrahydrocarbazole
99%
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About This Item
Empirical Formula (Hill Notation):
C12H13N
CAS Number:
Molecular Weight:
171.24
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Assay
99%
bp
325-330 °C (lit.)
mp
118-120 °C (lit.)
SMILES string
C1CCc2c(C1)[nH]c3ccccc23
InChI
1S/C12H13N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1,3,5,7,13H,2,4,6,8H2
InChI key
XKLNOVWDVMWTOB-UHFFFAOYSA-N
Application
1,2,3,4-Tetrahydrocarbazole can be used as a starting material to prepare:
- Spiro[cyclopentane-1,2′-indolin-3′-one] by photooxygenation.
- 9-Acyl-1,2,3,4-tetrahydrocarbazoles by N-acylation reactions.
- Carbazole via palladium-catalyzed asymmetric hydrogenation reaction.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Xu-Fan Wang et al.
Organic letters, 12(5), 1140-1143 (2010-02-12)
A hydrogen bonding-mediated double Michael addition-aromatization cascade of 2-propenylindoles and nitroolefins has been disclosed. The methodology allows an efficient synthesis of diverse and structurally complex tetrahydrocarbazoles in good to excellent enantioselectivities and diastereoselectivities.
Synthesis of novel 1-substituted and 1, 9-disubstituted-1, 2, 3, 4-tetrahydro-9H-carbazole derivatives as potential anticancer agents
Shmeiss NAMM, et al.
Molecules (Basel), 5(10), 1101-1112 (2000)
P Crawford et al.
The Journal of chemical physics, 128(10), 105104-105104 (2008-03-19)
The carbazole moiety is a component of many important pharmaceuticals including anticancer and anti-HIV agents and is commonly utilized in the production of modern polymeric materials with novel photophysical and electronic properties. Simple carbazoles are generally produced via the aromatization
Uma Siripurapu et al.
Bioorganic & medicinal chemistry letters, 16(14), 3793-3796 (2006-05-20)
Comparison of several amine-substituted and methoxy-substituted analogs of N1-(4-aminobenzene)sulfonylindole suggests that these substituents might contribute to the 5-HT6 serotonin receptor affinity of these agents via their electronic effect on the indolic nucleus. Their 1,2,3,4-tetrahydrocarbazole counterparts behave differently.
Subhasish Neogi et al.
Journal of combinatorial chemistry, 12(5), 617-629 (2010-07-01)
The one-pot synthesis of a new substituted 1,2,3,4-tetrahydrocarbazoles has been described via Petasis reactions. These tetrahydrocarbazoles exhibits various medicinal importance and might be suitable for elaboration into larger peptides at carboxy termini. The scope and limitations of this method have
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