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Sigma-Aldrich

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

technical grade

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Synonym(s):
NSC 25094
Empirical Formula (Hill Notation):
C11H7NO
CAS Number:
130-00-7
Molecular Weight:
169.18
EC Number:
204-973-4
MDL number:
MFCD00009748
UNSPSC Code:
12352100
PubChem Substance ID:
24860382
NACRES:
NA.22

grade

technical grade

form

solid

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

  • Reactant in photo-Fries rearrangement
  • Reactant in preparation of potential antitumor agents
  • Reactant in synthesis of inhibitors of thymidylate synthase
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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

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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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

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