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N206

Sigma-Aldrich

2-Naphthaldehyde

98%

Synonym(s):

β-Naphthaldehyde

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5 G
$50.30
25 G
$128.00
100 G
$496.00

About This Item

Linear Formula:
C10H7CHO
CAS Number:
Molecular Weight:
156.18
Beilstein/REAXYS Number:
507750
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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Quality Level

assay

98%

form

crystals

mp

58-61 °C (lit.)

storage temp.

−20°C

SMILES string

[H]C(=O)c1ccc2ccccc2c1

InChI

1S/C11H8O/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-8H

InChI key

PJKVFARRVXDXAD-UHFFFAOYSA-N

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Application

2-Naphthaldehyde can be used as a reactant:
  • In proline catalyzed aldol reaction.[1]
  • In asymmetric three-component Mannich reaction.[2]
  • For the synthesis of Hantzsch 1,4-dihydropyridines.13}
  • Asymmetric benzoin condensation reaction.[3]
  • For the synthesis of pyrazolo[1,2−b]phthalazinediones.[4]
  • For the synthesis C60 by flash vacuum pyrolysis.[5]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Proline-catalyzed direct asymmetric aldol reactions.
List B, et al.
Journal of the American Chemical Society, 122(10), 2395-2396 (2000)
Amelioration of H4 [W12SiO40] by nanomagnetic heterogenization: For the synthesis of 1H-pyrazolo [1, 2-b] phthalazinedione derivatives.
Arora P and Rajput JK
Applied Organometallic Chemistry, 32(2), e4001-e4001 (2018)
The direct catalytic asymmetric three-component Mannich reaction.
List B
Journal of the American Chemical Society, 122(38), 9336-9337 (2000)
An efficient nucleophilic carbene catalyst for the asymmetric benzoin condensation.
Enders D and Kallfass U
Angewandte Chemie (International Edition in English), 41(10), 1743-1745 (2002)
Zhipeng Zhang et al.
Nature communications, 7, 12478-12478 (2016-08-18)
Due to the high versatility of chiral cyanohydrins, the catalytic asymmetric cyanation reaction of carbonyl compounds has attracted widespread interest. However, efficient protocols that function at a preparative scale with low catalyst loading are still rare. Here, asymmetric counteranion-directed Lewis

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