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Key Documents

682756

Sigma-Aldrich

1-(3-Bromo-1-propynyl)naphthalene

97%

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About This Item

Empirical Formula (Hill Notation):
C13H9Br
CAS Number:
Molecular Weight:
245.11
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

solid

mp

43-47 °C

functional group

bromo

SMILES string

BrCC#Cc1cccc2ccccc12

InChI

1S/C13H9Br/c14-10-4-8-12-7-3-6-11-5-1-2-9-13(11)12/h1-3,5-7,9H,10H2

InChI key

LHDMQJTYLOVTPS-UHFFFAOYSA-N

Application

Reagent for the protection of alcohols in the form of a 1-naphthylpropargyl ether that can be cleaved with DDQ.[1]

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves


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David Crich et al.
Organic letters, 8(21), 4879-4882 (2006-10-06)
[reaction: see text] The (1-naphthyl)propargyl group is introduced as a sterically unobtrusive alcohol protecting group that is cleaved in a single step by exposure to dichlorodicyanoquinone in wet dichloromethane. In conjunction with the 4,6-O-benzylidene protecting group, and the use of

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