336467

Sigma-Aldrich

Benz[cd]indol-2(1H)-one

technical grade

Synonym(s):
NSC 25094
Empirical Formula (Hill Notation):
C11H7NO
CAS Number:
Molecular Weight:
169.18
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

grade

technical grade

Quality Level

mp

173-178 °C (lit.)

solubility

methanol: soluble 25 mg/mL, clear to slightly hazy, yellow to brown

SMILES string

O=C1Nc2cccc3cccc1c23

InChI

1S/C11H7NO/c13-11-8-5-1-3-7-4-2-6-9(12-11)10(7)8/h1-6H,(H,12,13)

InChI key

GPYLCFQEKPUWLD-UHFFFAOYSA-N

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General description

Benz[cd]indol-2(1H)-one is also referred as naphtholactam.

Application

Benz[cd]indol-2(1H)-one was used in the synthesis of 2-oxo-1,2-dihydrobenzo[cd]indole-6-sulfonamide analog, novel Mycobacterium protein tyrosine phosphatase B (mPTPB) inhibitor.
  • Reactant in photo-Fries rearrangement
  • Reactant in preparation of potential antitumor agents
  • Reactant in synthesis of inhibitors of thymidylate synthase

Packaging

5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Lan Chen et al.
ACS medicinal chemistry letters, 1(7), 355-359 (2010-12-01)
Mycobacterium protein tyrosine phosphatase B (mPTPB) is an essential virulence factor required for Mycobacterium tuberculosis (Mtb) survival in host macrophages. Consequently, mPTPB represents an exciting new target with a completely novel mechanism of action. We screened a library of 7,500...
Saeed I Khan et al.
Acta crystallographica. Section C, Crystal structure communications, 68(Pt 1), o1-o6 (2012-01-10)
Weakly diffracting crystals of benz[cd]indol-2(1H)-one (naphtholactam), C(11)H(7)NO, were unsuitable for data collection by early photographic methods. However, a diffractometer data set collected at room temperature in 1989 was solved and refined. The peak scans were broad, and the results indicated...
Articles
The Fries rearrangement reaction is an organic name reaction which involves the conversion of phenolic esters into hydroxyaryl ketones on heating in the presence of a catalyst. Suitable catalysts for this reaction are Brønsted or Lewis acids such as HF, AlCl3, BF3, TiCl4, or SnCl4. The Fries rearrangement reaction is an ortho, para-selective reaction, and is used in the preparation of acyl phenols. This organic reaction has been named after German chemist Karl Theophil Fries.
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