3-BROMO-2-HYDROXY-5-NITROBENZALDEHYDE Chemical Properties

Melting point:

146-149 °C

Boiling point:

299.6±40.0 °C(Predicted)

Density 

1.928±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

pka

3.38±0.44(Predicted)

color 

Light orange to Yellow to Green

Sensitive 

Air Sensitive

BRN 

1213613

InChI

InChI=1S/C7H4BrNO4/c8-6-2-5(9(12)13)1-4(3-10)7(6)11/h1-3,11H

InChIKey

BESBCGANGAEHPM-UHFFFAOYSA-N

SMILES

C(=O)C1=CC([N+]([O-])=O)=CC(Br)=C1O

CAS DataBase Reference

16789-84-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22

Safety Statements 

36/37

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2913000090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-BROMO-2-HYDROXY-5-NITROBENZALDEHYDE Usage And Synthesis

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 5867, 2007 DOI: 10.1021/jo070477u

Synthesis

General procedure for the synthesis of 3-bromo-2-hydroxy-5-nitrobenzaldehyde from 5-nitrosalicylaldehyde: 2-hydroxy-5-nitrobenzaldehyde (2.0 g, 12 mmol) and dichloromethane (30 mL) were added to a 100 mL two-necked flask, followed by the addition of bromine (2.24 g, 14 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the reaction was quenched with saturated aqueous sodium thiosulfate (100 mL) and the mixture was transferred to a separatory funnel for layering. The aqueous phase was extracted with ethyl acetate (100 mL × 2). The organic phases were combined, washed with saturated brine (80 mL × 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether, v/v = 1/20) to afford 3-bromo-2-hydroxy-5-nitrobenzaldehyde as a yellow solid (2.89 g, 98% yield). Mass spectrum (ES-API, cation mode) m/z: 246.9 [M + 2]+.

References

[1] Organic Letters, 2011, vol. 13, # 1, p. 26 - 29
[2] Tetrahedron Letters, 2005, vol. 46, # 51, p. 8959 - 8963
[3] Patent: WO2017/36404, 2017, A1. Location in patent: Page/Page column 115
[4] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
[5] Patent: CN108623615, 2018, A. Location in patent: Paragraph 0332; 0547; 0548; 0549

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