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557927

Sigma-Aldrich

1-Ethynylnaphthalene

97%

Synonym(s):

α-Ethynylnaphthalene, α-Naphthylacetylene, 1-Ethynylnaphthalene, 1-Naphthylacetylene, 1-Naphthylethyne

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About This Item

Linear Formula:
C10H7C≡CH
CAS Number:
15727-65-8
Molecular Weight:
152.19
MDL number:
MFCD02093737
UNSPSC Code:
12352100
PubChem Substance ID:
24879707
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.6500 (lit.)

density

1.070 g/mL at 25 °C (lit.)

SMILES string

C#Cc1cccc2ccccc12

InChI

1S/C12H8/c1-2-10-7-5-8-11-6-3-4-9-12(10)11/h1,3-9H

InChI key

MCZUXEWWARACSP-UHFFFAOYSA-N

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General description

1-Ethynylnaphthalene can be prepared from 1-acetonaphthone or 1-naphthyl-2-trimethylsilylacetylene.

Application

1-Ethynylnaphthalene may be used to synthesize bis-6,6′-(ethynyl-1-naphthalene)-2,2′-bipyridine.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

136.0 °F - closed cup

Flash Point(C)

57.8 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC2874V
BGBB4129V
20397LJ
00412LH
14427AE

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G J Hammons et al.
Chemical research in toxicology, 2(6), 367-374 (1989-11-01)
Since the N-oxidation of several carcinogenic arylamines has been shown to be catalyzed preferentially by cytochrome P-450IA2 in several species, homologous ethynyl-substituted aromatic hydrocarbons, 2-ethynylnaphthalene, 1-ethynylnaphthalene, and 2-ethynylfluorene, were synthesized and examined as potential mechanism-based inactivators of this monooxygenase. By
Bipyridylacetylenes 1: the synthesis of some bipyridylacetylenes via the palladium-catalyzed coupling of acetylenes with 2, 2'-dibromobipyridyl, and the single crystal X-ray structure of 6, 6'-bisphenylethynyl-2, 2'-bipyridine.
Butler IR and Soucy-Breau C.
Canadian Journal of Chemistry, 69(7), 1117-1123 (1991)

Articles

New Aromatic Terminal Alkynes

The terminal alkyne functionality has a wide range of applications including most recently the synthesis of spiropyran substituted 2,3-dicyanopyrazines and (±)-asteriscanolide, as well as conversion to enamines using resin-bound 2° amines.

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