5-Nitrovanillin Chemical Properties

Melting point:

172-175 °C (lit.)

Boiling point:

334.23°C (rough estimate)

Density 

1.5023 (rough estimate)

vapor pressure 

0.001Pa at 25℃

refractive index 

1.5700 (estimate)

Flash point:

97℃

storage temp. 

Inert atmosphere,2-8°C

solubility 

2.1g/L in organic solvents at 20 ℃

form 

powder to crystal

pka

4.97±0.38(Predicted)

color 

Yellow to Brown to Dark green

Water Solubility 

700mg/L at 23℃

Sensitive 

Air Sensitive

BRN 

1973746

LogP

0.301 at 23℃

CAS DataBase Reference

6635-20-7(CAS DataBase Reference)

EPA Substance Registry System

5-Nitrovanillin (6635-20-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

HS Code 

29130000

MSDS

• Language:English Provider:5-Nitrovanillin
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Nitrovanillin Usage And Synthesis

Chemical Properties

yellow-green fine crystalline powder

Uses

5-Nitrovanillin is a reagent used in the synthesis of feruloyl and caffeoyl which have antitumor properties.

Definition

ChEBI: A member of the class of benzaldehydes that is vanillin in which the hydrogen ortho- to the hydroxy group is substituted by a nitro group.

Flammability and Explosibility

Non flammable

Synthesis

The general procedure for the synthesis of 5-nitrovanillin from vanillin was as follows: vanillin (94 mg, 1 mmol) was dissolved in 3 mL of glacial acetic acid in a 50 mL test tube. Solid Y(NO3)3-6H2O (383 mg, 1 mmol) was then added and the reaction mixture was shaken continuously for 10 min at room temperature. The reaction process was monitored by thin layer chromatography (TLC) in petroleum ether with 10% ethyl acetate. Upon completion of the reaction, 30 mL of ice-cold water was added to the reaction mixture and allowed to stand for 15 min. The solid product formed was collected by filtration and washed with cold water. The solid product obtained was used directly for analysis without further purification. The experimental methods for synthesizing compounds 2a-2e are detailed in Supporting Information.

Purification Methods

It forms yellow plates from AcOH and needles from EtOH [Slotta & Szyszke Chem Ber 68 184 1935]. With diazomethane, 5-nitro-3,4-dimethoxyacetophenone is formed [Brady & Manjunath J Chem Soc 125 1067 1924]. The methyl ether crystallises from EtOAc or AcOH, m 88o, 90-91o, and the phenylhydrazone has m 108-110o (from aqueous EtOH). [Finger & Schott J Prakt Chem [2] 115 288 1927.] The oxime has m 216o (from EtOH or AcOH), and the oxime acetate has m 147o (from aqueous EtOH) [Vogel Monatsh Chem 20 384 1899, Brady & Dunn J Chem Soc 107 1861 1915]. [Beilstein 8 III 2064.]

References

[1] Journal of Physical Organic Chemistry, 2000, vol. 13, # 9, p. 511 - 517
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3396 - 3411
[3] Tetrahedron Letters, 2006, vol. 47, # 15, p. 2507 - 2509
[4] Synthetic Communications, 2008, vol. 38, # 11, p. 1745 - 1752
[5] Tetrahedron, 1992, vol. 48, # 10, p. 1895 - 1910

5-Nitrovanillin(6635-20-7)Related Product Information

• 3,4-DIMETHOXY-5-NITRO-BENZOIC ACID
• 5-Nitrovanillin
• Vanillin
• 3,4-DIMETHOXY-5-NITRO-BENZALDEHYDE
• 3-ETHOXY-4-HYDROXY-5-NITROBENZALDEHYDE
• CHEMBRDG-BB 6766958
• CHEMBRDG-BB 6755049
• 4-Hydroxy-3-methoxy-5-nitrobenzaldehyde(5-Nitrovanillin)
• 3-METHOXY-5-NITRO-4-(PYRIDIN-4-YLMETHOXY)BENZALDEHYDE
• RARECHEM AL BF 0173
• 2-(4-FORMYL-2-METHOXY-6-NITROPHENOXY)-N-PROP-2-YNYLACETAMIDE
• AKOS B028931
• N-ETHYL-2-(4-FORMYL-2-METHOXY-6-NITROPHENOXY)ACETAMIDE
• 3-METHOXY-5-NITRO-4-(PYRIDIN-3-YLMETHOXY)BENZALDEHYDE
• AKOS 201-11
• RARECHEM AL BE 0173
• 3-METHOXY-5-NITRO-4-(PYRIDIN-2-YLMETHOXY)BENZALDEHYDE
• RARECHEM AL BI 0173