| Identification | More | [Name]
3-Nitrosalicylaldehyde | [CAS]
5274-70-4 | [Synonyms]
2-HYDROXY-3-NITROBENZALDEHYDE
3-NITROSALICYLALDEHYDE
AKOS B029850
LABOTEST-BB LT00939229
2-hydroxy-3-nitro-benzaldehyd
3-nitro-2-hydroxybenzaldehyde
3-nitrosalicaldehyde | [EINECS(EC#)]
226-098-7 | [Molecular Formula]
C7H5NO4 | [MDL Number]
MFCD00041874 | [Molecular Weight]
167.12 | [MOL File]
5274-70-4.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29130000 |
| Hazard Information | Back Directory | [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 |
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