Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

T12408

Sigma-Aldrich

1,2,3,4-Tetrahydrocarbazole

99%

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

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.
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service