5-Methoxy-2-nitrobenzaldehyde Chemical Properties

Melting point:

83 °C

Boiling point:

354.7±27.0 °C(Predicted)

Density 

1.322±0.06 g/cm3(Predicted)

storage temp. 

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

form 

crystalline solid

color 

Yellow

InChI

InChI=1S/C8H7NO4/c1-13-7-2-3-8(9(11)12)6(4-7)5-10/h2-5H,1H3

InChIKey

BNTDDWPHSMILHQ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

20357-24-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HS Code 

2912490090

5-Methoxy-2-nitrobenzaldehyde Usage And Synthesis

Uses

5-Methoxy-2-nitrobenzaldehyde is a starting material used to synthesize a novel class of cis-locked combretastatins named combretabenzodiazepines which shows cytotoxic and antitubulin activity.

Synthesis

Step 1. Synthesis of 5-methoxy-2-nitrobenzaldehyde: 5-hydroxy-2-nitrobenzaldehyde (1 eq.), iodomethane (1.1 eq.) and potassium carbonate (1 eq.) were dissolved in DMF at room temperature and the reaction was stirred for 16 hours. Upon completion of the reaction, the reaction mixture was concentrated and subsequently partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated to give 5-methoxy-2-nitrobenzaldehyde in quantitative yield. Mass spectrometry analysis showed the molecular ion peak [M+H]+ = 182.

References

[1] Patent: US2005/85482, 2005, A1. Location in patent: Page/Page column 13; 17
[2] Patent: WO2010/51031, 2010, A1. Location in patent: Page/Page column 45
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1678 - 1681
[4] Patent: CN107522766, 2017, A. Location in patent: Paragraph 0136; 0137; 0138
[5] Chemical Communications, 2011, vol. 47, # 42, p. 11683 - 11685

5-Methoxy-2-nitrobenzaldehyde(20357-24-8)Related Product Information

• 3,5-Dimethoxybenzaldehyde
• 2,6-Dimethoxybenzaldehyde
• 4-Nitrobenzaldehyde
• p-Anisaldehyde
• 2-Bromo-5-methoxybenzaldehyde
• Veratraldehyde
• (Trifluoromethoxy)benzene
• 3-Methoxybenzaldehyde
• o-Anisaldehyde
• 4-Nitrobenzoic acid
• 3-(METHOXYMETHOXY)BENZALDEHYDE
• 5-METHOXYTHIOPHENE-2-CARBOXYLIC ACID
• 5-METHOXY-2-METHYL-BENZOIC ACID METHYL ESTER
• 5-Methoxy-2-(trifluoroMethyl)benzaldehyde
• Nitrobenzene
• ETHYL 4,5-DIMETHOXY-2-NITROBENZOATE
• 6-Nitroveratraldehyde
• Methyl 2-nitro-3,4,5-trimethoxybenzoate