3-Nitro-4,5-dihydroxybenzaldehyde Chemical Properties

Melting point:

147 °C

Boiling point:

310.9±42.0 °C(Predicted)

Density 

1.667±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO

form 

Solid

pka

4.78±0.38(Predicted)

color 

Dark Yellow

InChI

InChI=1S/C7H5NO5/c9-3-4-1-5(8(12)13)7(11)6(10)2-4/h1-3,10-11H

InChIKey

BBFJODMCHICIAA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

116313-85-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25-36-43

Safety Statements 

26-36/37-45

RTECS 

CU5665000

HS Code 

2912.49.2600

Toxicity

mouse,LDLo,oral,312mg/kg (312mg/kg),Helvetica Chimica Acta. Vol. 72, Pg. 952, 1989.

3-Nitro-4,5-dihydroxybenzaldehyde Usage And Synthesis

Chemical Properties

Dark Yellow Solid

Uses

3,4-Dihydroxy-5-nitrobenzaldehyde (Entacapone EP Impurity C) is an Entacapone (E558500) impurity.

Uses

Entacapone (E558500) impurity.

Synthesis

The general procedure for the synthesis of 3,4-dihydroxy-5-nitrobenzaldehyde from 5-nitrovanillin was as follows: iodine (2.095 g), aluminum powder (0.368 g) and acetonitrile (40 mL) were added to a 100 mL aubergine flask, heated to reflux, and stirred for 2 hr until the violet-red color of the iodine disappeared completely. Subsequently, pyridine (1.597 g) and 5-nitrovanillin (0.986 g) were added and the reaction was continued for 18 hours. After completion of the reaction, the mixture was cooled to room temperature and then acidified by adding 2 mol/L dilute hydrochloric acid (10 mL) to the reaction solution. The reaction mixture was extracted with ethyl acetate (50 mL x 3), the organic phases were combined and dried with anhydrous sodium sulfate. The filtrate was concentrated to dryness by rotary evaporator to remove the solvent. Finally, the residue was purified by fast column chromatography (mobile phase of ethyl acetate to petroleum ether 1:3, v/v) to afford the target product 3,4-dihydroxy-5-nitrobenzaldehyde (yellow solid, 0.650 g, 71% yield).

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 5, p. 1969 - 1989
[2] Journal of Organic Chemistry, 2000, vol. 65, # 23, p. 8001 - 8010
[3] Journal of the American Chemical Society, 2000, vol. 122, # 44, p. 10781 - 10787
[4] Organic Letters, 2008, vol. 10, # 7, p. 1369 - 1372
[5] Patent: WO2016/199943, 2016, A1. Location in patent: Paragraph 0402

3-Nitro-4,5-dihydroxybenzaldehyde(116313-85-0)Related Product Information

• 2,4-Dimethylbenzaldehyde
• Solvent Red 43
• 3-Nitrobenzaldehyde
• Protocatechualdehyde
• 3,4-Dimethylbenzaldehyde
• 4-Hydroxybenzaldehyde
• 3-Hydroxybenzaldehyde
• 4-Nitrobenzaldehyde
• 2,4-Dihydroxybenzaldehyde
• Entacapone EP IMpurity B
• Entacapone EP Impurity G
• 3,4-Dihydroxy-5-Nitrobenzoic Acid
• (E/Z)-3-O-Methyl Entacapone
• (alphaE)-alpha-[(3,4-Dihydroxy-5-nitrophenyl)methylene]-beta-oxo-1-piperidinepropanenitrile
• (2E)-2-Cyano-3-(3-ethoxy-4-hydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide
• 2-Propenamide, 2-cyano-3-(3,4-dihydroxyphenyl)-N,N-diethyl-, (2E)-
• TYRPHOSTIN AG 1290
• Entacapone Impurity 13