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A38800

Sigma-Aldrich

2-Aminoanthracene

96%

Synonym(s):

2-Anthramine

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About This Item

Empirical Formula (Hill Notation):
C14H11N
CAS Number:
Molecular Weight:
193.24
Beilstein:
2209414
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

96%

form

powder

mp

238-241 °C (lit.)

SMILES string

Nc1ccc2cc3ccccc3cc2c1

InChI

1S/C14H11N/c15-14-6-5-12-7-10-3-1-2-4-11(10)8-13(12)9-14/h1-9H,15H2

InChI key

YCSBALJAGZKWFF-UHFFFAOYSA-N

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Application

2-Aminoanthracene can be used as a reactant to prepare:
  • Steroid derived naphthoquinoline asphaltene compounds via multicomponent cyclocondensation reaction with 5-α-cholestan-3-one and aromatic aldehydes.
  • Naphtho[2,3- f ]quinoline derivatives by reacting with aromatic aldehyde and acetone or acetophenone catalyzed by iodine.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - 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

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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Steroid-Derived Naphthoquinoline Asphaltene Model Compounds: Hydriodic Acid Is the Active Catalyst in I2-Promoted Multicomponent Cyclocondensation Reactions
Schulze M, et al.
Organic Letters, 17(23), 5930-5933 (2015)
An efficient method for the synthesis of naphthoquinoline derivatives catalyzed by iodine
Wang W, et al.
Heterocyclic Communications, 18(1), 17-21 (2012)
Jason M God et al.
Journal of medicinal food, 10(1), 54-59 (2007-05-03)
The initiating event in carcinogenesis is a somatic mutation. During progression of the disease, additional mutations accumulate as the transformed cells develop the ability to proliferate and metastasize. These mutations can be produced by reactive oxygen species (ROS) generated through
H W Zhao et al.
Mutation research, 564(2), 103-113 (2004-10-28)
Exposure of rats to diesel exhaust particles (DEP) or carbon black (CB) has been shown to induce time-dependent changes in CYP1A1and CYP2B1 in the lung. The present study evaluated the role of these metabolic enzymes on the pulmonary bioactivation of
Rodrigo Juliano Oliveira et al.
Toxicology in vitro : an international journal published in association with BIBRA, 20(7), 1225-1233 (2006-05-24)
Due to the need to identify new antimutagenic agents and to determine their mechanism of action, the present study examined the mechanism of action of the beta-glucan with regard to antimutagenicity using the micronucleus assay in CHO-k1 and HTC cell

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