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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ9392
MKCP5044
MKCN5048
MKCJ2466
MKCG1679

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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
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)
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)
A novel TMSI-mediated synthesis of Hantzsch 1, 4-dihydropyridines at ambient temperature.
Sabitha G, et al.
Tetrahedron Letters, 44(21), 4129-4131 (2003)
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