ChemicalBook Product Catalog Chemical Reagents Organic reagents Aromatic aldehydes 1-BROMO-2-NAPHTHALDEHYDE

1-BROMO-2-NAPHTHALDEHYDE

Product Name1-BROMO-2-NAPHTHALDEHYDE
CAS3378-82-3
MFC11H7BrO
MW235.08
EINECS222-180-1
MOL File3378-82-3.mol

Chemical Properties

Melting point	118°C
Boiling point	347℃
Density	1.552
Flash point	120℃
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	soluble in Methanol
form	crystals
Appearance	Off-white to yellow Solid
BRN	2613639
InChI	InChI=1S/C11H7BrO/c12-11-9(7-13)6-5-8-3-1-2-4-10(8)11/h1-7H
InChIKey	CYGUXEZVBLMVRV-UHFFFAOYSA-N
SMILES	C1(Br)=C2C(C=CC=C2)=CC=C1C=O
CAS DataBase Reference	3378-82-3(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
WGK Germany	3
HS Code	29130000
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Light yellow solid

Uses

1-Bromo-2-naphthaldehyde is used as a reagent in the synthesis of Hoveyda-Grubbs type metathesis catalysts which are used in cross olefin metathesis. 1-Bromo-2-naphthaldehyde is also used in the preparation of novel (-)-cercosporamide derivatives as potent selective PPARγ modulators.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 4617, 1981 DOI: 10.1021/jo00335a076

Synthesis

37763-43-2

3378-82-3

General procedure for the synthesis of 1-bromo-2-naphthalene formaldehyde from 1-bromo-2-(bromomethyl)naphthalene: In a 2L reactor, 4-methylmorpholine N-oxide (61.4 g, 524 mmol), molecular sieves (200 g) and acetonitrile (1.2 L) were added and stirred for 30 min at 0 °C under nitrogen protection. Subsequently, 1-bromo-2-(bromomethyl)naphthalene (78 g, 262 mmol) was added and stirring was continued for 6 hours at room temperature. After completion of the reaction, the reaction mixture was filtered and the filtrate was washed with dichloromethane. The filtrate was concentrated and purified by column chromatography to afford 1-bromo-2-naphthaldehyde (45 g) in 73% yield.

References

[1] European Journal of Organic Chemistry, 2012, # 31, p. 6155 - 6164,10
[2] European Journal of Organic Chemistry, 2012, # 31, p. 6155 - 6164
[3] Tetrahedron Letters, 1994, vol. 35, # 48, p. 8985 - 8988
[4] Patent: US2018/72753, 2018, A1. Location in patent: Paragraph 0163-0164
[5] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 9, p. 1363 - 1378

1-BROMO-2-NAPHTHALDEHYDE

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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