3-BROMO-2-HYDROXY-5-NITROBENZALDEHYDE

3-BROMO-2-HYDROXY-5-NITROBENZALDEHYDE Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

3-BROMO-2-HYDROXY-5-NITROBENZALDEHYDE Chemical Properties,Usage,Production

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