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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

557927-VAR:
557927-5G:
557927-BULK:

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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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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