2-NITRO 5-BROMO-BENZALDEHYDE Chemical Properties

Melting point:

71.0 to 75.0 °C

Boiling point:

330.5±27.0 °C(Predicted)

Density 

1.781±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Light red to Green

λmax

276nm(CH3CN)(lit.)

InChI

InChI=1S/C7H4BrNO3/c8-6-1-2-7(9(11)12)5(3-6)4-10/h1-4H

InChIKey

UFRVBZVJVRHSNR-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

20357-20-4

Safety Information

Risk Statements 

43

Safety Statements 

36/37

RTECS 

CU4875000

HS Code 

2913000090

Toxicity

mouse,LD50,intravenous,32mg/kg (32mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07008,

2-NITRO 5-BROMO-BENZALDEHYDE Usage And Synthesis

Uses

2-Bromo-5-nitrobenzaldehyde is a cholesteryl ester transfer protein (CETP) inhibitor. 2-Bromo-5-nitrobenzaldehyde is a commonly used reactant for the synthesis of (-)-Linarinic acid derivatives as neuroprotective agents against oxygen glucose deprivation (OGD)-??induced cell damage.

Synthesis

1. Concentrated nitric acid (10 mL) is slowly added dropwise to a solution of concentrated sulfuric acid (120 mL) containing 3-bromobenzaldehyde (11.7 mL, 100 mmol) at 5°C. The reaction system is allowed to come to room temperature with continuous stirring overnight. 2. The reaction system was allowed to warm naturally to room temperature with continuous stirring overnight. 3. The reaction mixture was slowly poured into ice water and the resulting precipitate was collected by filtration. 4. 4. The precipitate was dissolved in dichloromethane, dried by adding anhydrous magnesium sulfate, and the solvent was subsequently concentrated under reduced pressure. 5. The crude product was purified by fast column chromatography on silica gel with 25% ethyl acetate/isohexane as eluent to afford the target compound 5-bromo-2-nitrobenzaldehyde (16g, 70% yield). 6. The product NMR hydrogen spectral data (500 MHz, CDCl3): δ 10.41 (1H, s), 8.06 (1H, d, J = 2.1 Hz), 8.02 (1H, d, J = 8.6 Hz), 7.87 (1H, dd, J = 2.1,8.6 Hz).

References

[1] Chemistry - A European Journal, 2013, vol. 19, # 7, p. 2442 - 2449
[2] Patent: CN105669566, 2016, A. Location in patent: Paragraph 0027; 0028; 0029; 0030; 0031
[3] Journal of Organic Chemistry, 2014, vol. 79, # 17, p. 7822 - 7830
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 33, p. 6115 - 6122
[5] Patent: WO2006/100519, 2006, A1. Location in patent: Page/Page column 16-17

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