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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

N206-VAR-A:
N206-BULK-A:
N206-10KG-A:
N206-5G-A:
N206-100G-A:
N206-25G-A:

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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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