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N206

Sigma-Aldrich

2-Naphthaldehyde

98%

Synonym(s):

β-Naphthaldehyde

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About This Item

Linear Formula:
C10H7CHO
CAS Number:
66-99-9
Molecular Weight:
156.18
Beilstein:
507750
EC Number:
200-640-2
MDL number:
MFCD00004094
UNSPSC Code:
12352100
PubChem Substance ID:
24897548
NACRES:
NA.22

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.
  • In asymmetric three-component Mannich reaction.
  • For the synthesis of Hantzsch 1,4-dihydropyridines.13}
  • Asymmetric benzoin condensation reaction.
  • For the synthesis of pyrazolo[1,2−b]phthalazinediones.
  • For the synthesis C60 by flash vacuum pyrolysis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Proline-catalyzed direct asymmetric aldol reactions.
List B, et al.
Journal of the American Chemical Society, 122(10), 2395-2396 (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
The direct catalytic asymmetric three-component Mannich reaction.
List B
Journal of the American Chemical Society, 122(38), 9336-9337 (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)
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.
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