3-Nitrosalicylaldehyde Chemical Properties

Melting point:

105-109 °C(lit.)

Boiling point:

295.67°C (rough estimate)

Density 

1.5216 (rough estimate)

refractive index 

1.6280 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder

pka

5.07±0.24(Predicted)

color 

Yellow to brown

Water Solubility 

slightly soluble

Sensitive 

Air Sensitive

CAS DataBase Reference

5274-70-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzaldehyde, 2-hydroxy-3-nitro-(5274-70-4)

EPA Substance Registry System

Benzaldehyde, 2-hydroxy-3-nitro- (5274-70-4)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22-20/21/22

Safety Statements 

26-36-36/37/39

WGK Germany 

3

TSCA 

Yes

HS Code 

29130000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Nitrosalicylaldehyde Usage And Synthesis

Chemical Properties

yellow to brown crystalline powder

Uses

2-Hydroxy-3-nitrobenzaldehyde may be used in the synthesis of 5-acetyl-4-aryl-6-methyl-1,2,3,4-tetrahydro pyrimidine.

General Description

2-Hydroxy-3-nitrobenzaldehyde can be extracted from the leaves of Actephila merrilliana. Its molecule is planar. On reaction with dapsone, it affords a colorless solution.

Synthesis

GENERAL METHOD: Salicylaldehyde (10 mmol) was mixed with urea nitrate (10 mmol) in acetonitrile-water solvent mixture (95:5, 5 ml, v/v) in a 25 ml round bottom flask. The reaction mixture was placed in a Milestone Start SYNTH microwave reactor and heated at 80°C for 40-50 min. Upon completion of the reaction, the reaction mixture was cooled to room temperature, quenched with water and extracted with dichloromethane. The organic phase was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to afford the target product 3-nitrosalicylaldehyde. In all experiments, o-nitrosalicylaldehyde was selectively generated and no para-nitro-substituted by-products were detected. The resulting compounds were characterized by 1H NMR, 13C NMR, melting point determination (for solid samples), GC-MS analysis and comparison with standards.

References

[1] Chinese Chemical Letters, 2010, vol. 21, # 4, p. 403 - 406
[2] Synthetic Communications, 2011, vol. 41, # 20, p. 2985 - 2992
[3] Tetrahedron Letters, 2014, vol. 55, # 7, p. 1320 - 1322
[4] Patent: WO2012/92880, 2012, A1. Location in patent: Page/Page column 57-58
[5] Tetrahedron, 1969, vol. 25, p. 3251 - 3266

3-Nitrosalicylaldehyde(5274-70-4)Related Product Information

• 5-Methylsalicylaldehyde
• 4-Nitrobenzoic acid
• 3-NITRO BENZALDEHYDE
• CHLOROPHOSPHONAZO III
• 4-Hydroxy-3-nitrobenzaldehyde
• 3-Nitrobenzaldehyde
• 4-Hydroxybenzaldehyde
• 4-Nitrobenzaldehyde
• 3-Nitrotoluene
• Salicylaldehyde
• 2,4,6-Trinitrotoluene
• Nitromethane
• Nitrobenzene
• 2-NITROSALICYLALDEHYDE,2-HYDROXY 5-NITROBENZALDEHYDE/5-NITROSALICYLALDEHYDE,5-NITROSALICYLALDEHYDE,2-Hydroxy5-Nitrobenzaldehyae(5-nitrosalicylaldehyde
• 5-METHOXY-3-NITROSALICYLALDEHYDE 97%,5-METHOXY-3-NITROSALICYLALDEHYDE
• 3-Nitrosalicylic acid
• 3,5-Dinitrosalicylic acid
• 2,6-DIMETHOXY-3-NITROBENZOIC ACID