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N9005

Sigma-Aldrich

1-Naphthylamine

97%

Synonym(s):

α-Naphthylamine, 1-Aminonaphthalene

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About This Item

Linear Formula:
C10H7NH2
CAS Number:
Molecular Weight:
143.19
Beilstein:
386133
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

color

light tan to purple

bp

301 °C (lit.)

mp

47-50 °C (lit.)

density

1.114 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

Nc1cccc2ccccc12

InChI

1S/C10H9N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,11H2

InChI key

RUFPHBVGCFYCNW-UHFFFAOYSA-N

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General description

α-Naphthylamine, a naphthalene substituted by an amino group is an organic dye used as a detection reagent in the synthesis of novel azo dyes.

Application

1-Naphthylamine has been used in the synthesis of Pitnot-2, an inactive analog of clathrin inhibitor Pitstop 2.
It can also be used as a starting material to synthesize:
  • [(S)-HY-Phos], a novel chiral phosphine-phosphoramidite ligand for use in rhodium-catalyzed asymmetric hydrogenation of various functionalized olefins.
  • N-(naphthalen-1-yl)picolinamide.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 1A

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis of the Pitstop family of clathrin inhibitors.
Robertson M J, et al.
Nature Protocols, 9(7), 1592-1592 (2014)
Novel chiral phosphine-phosphoramidite ligands derived from 1-naphthylamine for highly efficient Rh-catalyzed asymmetric hydrogenation.
Yu S B, et al.
Tetrahedron Asymmetry, 19(15), 1862-1866 (2008)
Cobalt?Catalyzed, Aminoquinoline?Directed C (sp2)- H Bond Alkenylation by Alkynes.
Grigorjeva L and Daugulis O
Angewandte Chemie (International Edition in English), 126(38), 10373-10376 (2014)
V Chubanov et al.
British journal of pharmacology, 166(4), 1357-1376 (2012-01-17)
Transient receptor potential cation channel subfamily M member 7 (TRPM7) is a bifunctional protein comprising a TRP ion channel segment linked to an α-type protein kinase domain. TRPM7 is essential for proliferation and cell growth. Up-regulation of TRPM7 function is
Xiaolin Zhang et al.
Inorganic chemistry, 51(4), 2325-2331 (2012-02-10)
A unique gadolinium complex, Nap-DO3A-Gd, comprising a naphthylamine luminescent moiety, a di-2-picolylamine (DPA) binding chelator, and a 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid (DO3A) moiety has been designed and synthesized as a dual-functional probe for selective magnetic resonance imaging and fluorescent sensing of copper(II)

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