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Merck

A38800

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-330-9
Beilstein/REAXYS Number:
2209414
MDL number:
Assay:
96%
Form:
powder
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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

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves



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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