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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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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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1 of 4

This Item
N109146692C2648
Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

storage temp.

room temp

form

crystals

form

liquid

form

solid

form

powder

mp

58-61 °C (lit.)

mp

1-2 °C (lit.)

mp

51-54 °C (lit.)

mp

-

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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Dong-Sheng Lee et al.
Chirality, 28(1), 65-71 (2015-10-22)
Chiral O,N,O-tridentate phenol ligands bearing a camphor backbone were found to be effective chiral catalysts for the enantioselective addition of diethylzinc to aromatic aldehydes, resulting in high enantioselectivities (80-95% ee) at room temperature.
A rational chemical synthesis of C60.
Scott LT, et al.
Science, 295(5559), 1500-1503 (2002)
Proline-catalyzed direct asymmetric aldol reactions.
List B, et al.
Journal of the American Chemical Society, 122(10), 2395-2396 (2000)
The direct catalytic asymmetric three-component Mannich reaction.
List B
Journal of the American Chemical Society, 122(38), 9336-9337 (2000)
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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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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