6-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE Chemical Properties

Melting point:

102-105 °C(lit.)

Boiling point:

282.1±35.0 °C(Predicted)

Density 

1.653±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO : 113 mg/mL (489.09 mM)

form 

powder to crystal

pka

7.21±0.15(Predicted)

color 

Light yellow to Yellow to Orange

InChI

InChI=1S/C8H7BrO3/c1-12-7-3-2-6(9)5(4-10)8(7)11/h2-4,11H,1H3

InChIKey

JUPJZUTYDWXZAQ-UHFFFAOYSA-N

SMILES

C(=O)C1=C(Br)C=CC(OC)=C1O

CAS DataBase Reference

20035-41-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2913000090

MSDS

• Language:English Provider:SigmaAldrich

6-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE Usage And Synthesis

Uses

6-Bromo-2-hydroxy-3-methoxybenzaldehyde may be used in the synthesis of:

• 2-benzyloxy-6-bromo-3-methoxybenzaldehyde
• biphenyls
• antihypertensive natural products S-(+)-XJP and R-(-)-XJP

General Description

6-Bromo-2-hydroxy-3-methoxybenzaldehyde is a bromobenzaldehyde derivative. It participates in the synthesis of (±)-norannuradhapurine. Its crystals exhibit monoclinic crystal system and space group P2₁/n.

Synthesis

2-Acetoxy-3-methoxy-6-bromobenzaldehyde (48.2 g, 176.5 mmol) was used as starting material and dissolved in methanol (500 mL). Subsequently, 6 N hydrochloric acid (500 mL) was slowly added and the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the product was separated by diafiltration. The filter cake was washed with petroleum ether (100 mL × 3) and subsequently dried under vacuum to afford the yellow solid product 6-bromo-2-hydroxy-3-methoxybenzaldehyde (40.4 g, 99% yield).

References

[1] Patent: CN108358761, 2018, A. Location in patent: Paragraph 0042; 0043; 0078; 0079; 0096; 0097; 0105; 0106
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 14, p. 2731 - 2737
[3] Patent: US2003/220304, 2003, A1
[4] Patent: US2006/293394, 2006, A1. Location in patent: Figure 12
[5] Tetrahedron Letters, 2003, vol. 44, # 27, p. 5129 - 5132

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