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325325

Sigma-Aldrich

9-Methylcarbazole

99%

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About This Item

Empirical Formula (Hill Notation):
C13H11N
CAS Number:
1484-12-4
Molecular Weight:
181.23
EC Number:
216-054-5
MDL number:
MFCD00013431
UNSPSC Code:
12352100
PubChem Substance ID:
24859501

Assay

99%

mp

90-92 °C (lit.)

SMILES string

Cn1c2ccccc2c3ccccc13

InChI

1S/C13H11N/c1-14-12-8-4-2-6-10(12)11-7-3-5-9-13(11)14/h2-9H,1H3

InChI key

SDFLTYHTFPTIGX-UHFFFAOYSA-N

General description

9-Methylcarbazole is a nitrogen-containing polycyclic aromatic hydrocarbon.[1] Claisen-Schmidt condensation of 3-formyl-9-methylcarbazole with various amides of 3-aminoacetophenone yields N-{3-[3-(9-methyl-9H-carbazol-3-yl)-acryloyl]-phenyl}-benzamide/amide derivatives.[2]

Application

9-Methylcarbazole was used in facile synthesis of an organic electric conducting nanowire.[3]

Signal Word

Danger

Hazard Statements

H302,H318,H400

Precautionary Statements

P273 - P280 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Dam. 1

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

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

325325-VAR:
325325-BULK:
325325-5G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKBQ7701V
MKAA2178V
MKAA2178
02309BW
13826AI

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Doreen Waldau et al.
Applied microbiology and biotechnology, 83(1), 67-75 (2009-01-17)
Different 9H-carbazole derivatives have been investigated within the last decades due to their broad range of pharmacological applications. While the metabolism of 9H-carbazole has previously been reported, nothing was known about the bacterial transformation of 2,3,4,9-tetrahydro-1H-carbazole and 9-methyl-9H-carbazole. Thus, for
R Akasaka et al.
Archives of biochemistry and biophysics, 301(2), 355-360 (1993-03-01)
Cytochrome c (cyt.c) was shown to catalyze cytochrome P450 (P450)-like oxidative reactions, such as N-, and O-demethylation, S-oxidation, and epoxidation of olefins. A more detailed examination showed that (i) N-methylcarbazole and thioanisole oxidation with H2(18)O2 catalyzed by cyt.c resulted in
G L Kedderis et al.
The Journal of biological chemistry, 261(34), 15910-15914 (1986-12-05)
Chloroperoxidase, horseradish peroxidase, hemoglobin, myoglobin, lactoperoxidase, and microperoxidase catalyzed the ethyl hydroperoxide-dependent oxidation of N-methylcarbazole to N-(hydroxymethyl)carbazole and N-formylcarbazole as major products. Mass spectral analysis of the N-(hydroxymethyl)carbazole formed during the peroxidase-catalyzed N-demethylation of N-methylcarbazole in 18O-enriched medium indicated partial
G L Kedderis et al.
Molecular pharmacology, 23(3), 758-760 (1983-05-01)
The source of the oxygen atom in the product of the cytochrome P-450-catalyzed N-demethylation of N-methylcarbazole was determined by mass spectral analysis of the carbinolamine precursor of formaldehyde formed during incubation in oxygen 18-enriched medium. Initial experiments demonstrated that N-(hydroxymethyl)carbazole
T Shen et al.
Chemical research in toxicology, 7(2), 231-238 (1994-03-01)
The oxidation rate of NADPH is markedly stimulated during the mechanism-based inactivation of cytochrome P450 2B1 by N-methylcarbazole (NMC) in a reconstituted system consisting of NADPH-cytochrome P450 reductase, cytochrome P450 and phospholipid. The stimulation of NADPH oxidation in this system
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