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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:
613-13-8
Molecular Weight:
193.24
Beilstein:
2209414
EC Number:
210-330-9
MDL number:
MFCD00003582
UNSPSC Code:
12352100
PubChem Substance ID:
24890821
NACRES:
NA.22

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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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An efficient method for the synthesis of naphthoquinoline derivatives catalyzed by iodine
Wang W, et al.
Heterocyclic Communications, 18(1), 17-21 (2012)
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)
Jason A Scott et al.
Environmental toxicology and chemistry, 28(6), 1304-1310 (2009-01-27)
Environmentally relevant mixtures of polycyclic aromatic hydrocarbons (PAHs; e.g., crude oils) are often rich in alkyl-PAHs, such as retene (7-isopropyl-1-methylphenanthrene), which produce dioxin-like toxicity in fish embryos. The mechanism of alkyl-PAH toxicity is not well understood but was previously thought
A Di Sotto et al.
Journal of ethnopharmacology, 127(3), 731-736 (2009-12-09)
The aerial parts of Sisymbrium officinale Scop. are commonly used to treat airway ailments, moreover in antiquity the herbal drug was reputed to possess anticancer properties. The results obtained in present work support the traditional use and the properties ascribed
Junichiro Saito et al.
Mutation research, 609(1), 68-73 (2006-08-04)
Magnolol, a component of the bark of Magnolia obovata, has been reported to possess various biological activities, such as anti-carcinogenicity, anti-promotion activity and anti-oxidative activity. These findings suggest potential for this compound in cancer chemoprevention. Interestingly, there have been no
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