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T12408

Sigma-Aldrich

1,2,3,4-Tetrahydrocarbazole

99%

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About This Item

Empirical Formula (Hill Notation):
C12H13N
CAS Number:
942-01-8
Molecular Weight:
171.24
EC Number:
213-385-7
MDL number:
MFCD00004959
UNSPSC Code:
12352100
PubChem Substance ID:
24899946
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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

T12408-VAR:
T12408-1KG:
T12408-5G:
T12408-100G:
T12408-BULK:
T12408-25G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Carbazole ≥95% (GC)

Sigma-Aldrich

C5132

Carbazole

J Cao et al.
Chemosphere, 40(12), 1411-1416 (2000-05-02)
The solubilization of four pairs of substituted indole compounds (SICs) by beta-cyclodextrin (beta-CD) in water was investigated. The results show that 1,2,3,4-tetrahydrocarbazole and N-methyl-1,2,3,4-tetrahydrocarbazole form 1:1 inclusion complexes with beta-CD, while the other six SICs form 1:2 inclusion complexes, respectively.
Chao Zheng et al.
Accounts of chemical research, 53(4), 974-987 (2020-04-11)
ConspectusThe Pictet-Spengler reaction is a fundamental named reaction in organic chemistry, and it is the most straightforward method for the synthesis of tetrahydro-β-carbolines, a core structure embedded in numerous alkaloids. Spiroindolenines are often proposed as possible intermediates in Pictet-Spengler reactions.
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
Romano Di Fabio et al.
Bioorganic & medicinal chemistry letters, 16(6), 1749-1752 (2005-12-21)
The SAR of a new series of tetrahydrocarbazole derivatives is described: the appropriate decoration of this template led to the identification of a new class of NPY-1 antagonists showing good in vitro potency and a promising in vivo pharmacokinetic profile
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.
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