6-Bromo-2-hydroxy-3-methoxybenzaldehyde

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6-Bromo-2-hydroxy-3-methoxybenzaldehyde Basic information
Product Name:6-Bromo-2-hydroxy-3-methoxybenzaldehyde
Synonyms:6-Bromo-2-hydroxy-2-methoxybenzaldehyde;6-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE 99+%;2-Hydroxy-3-methoxy-6-bromobenzaldehyde;NSC95682;6-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE (NSC95682);6-Bromo-2-hydroxy-3-methoxybenzaldehyde >;Benzaldehyde, 6-bromo-2-hydroxy-3-methoxy-;IRE1,6 Bromo 2 hydroxy 3 methoxybenzaldehyde,6Bromo2hydroxy3methoxybenzaldehyde,inhibit,Inhibitor,NSC-95682,Inositol requiring enzyme 1,NSC 95682
CAS:20035-41-0
MF:C8H7BrO3
MW:231.04
EINECS:
Product Categories:Building Blocks;Carbonyl Compounds;Aldehydes;C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
Mol File:20035-41-0.mol
6-Bromo-2-hydroxy-3-methoxybenzaldehyde Structure
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)
pka7.21±0.15(Predicted)
form powder to crystal
color Light yellow to Yellow to Orange
InChIInChI=1S/C8H7BrO3/c1-12-7-3-2-6(9)5(4-10)8(7)11/h2-4,11H,1H3
InChIKeyJUPJZUTYDWXZAQ-UHFFFAOYSA-N
SMILESC(=O)C1=C(Br)C=CC(OC)=C1O
CAS DataBase Reference20035-41-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
HS Code 2913000090
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
6-Bromo-2-hydroxy-3-methoxybenzaldehyde Usage And Synthesis
Uses6-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 Description6-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
Benzaldehyde, 2-(acetyloxy)-6-bromo-3-methoxy-

159263-87-3

6-BROMO-2-HYDROXY-3-METHOXYBENZALDEHYDE

20035-41-0

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
6-Bromo-2-hydroxy-3-methoxybenzaldehyde Preparation Products And Raw materials
Raw materialsBenzaldehyde, 2-(acetyloxy)-6-bromo-3-methoxy--->2-Acetoxy-3-methoxybenzaldehyde 97-->Water-->Methanol-->Hydrochloric acid
Tag:6-Bromo-2-hydroxy-3-methoxybenzaldehyde(20035-41-0) Related Product Information
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