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3-Nitrosalicylaldehyde

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  • 2019-07-10
  • CAS:5274-70-4
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3-Nitrosalicylaldehyde Basic information
Product Name:3-Nitrosalicylaldehyde
Synonyms:2-hydroxy-3-nitro-benzaldehyd;LABOTEST-BB LT00939229;2-HYDROXY-3-NITROBENZALDEHYDE;3-NITROSALICYLALDEHYDE;AKOS B029850;3-nitro-2-hydroxybenzaldehyde;3-nitrosalicaldehyde;3-Nitrosalicylaldehyde, 98% 1GR
CAS:5274-70-4
MF:C7H5NO4
MW:167.12
EINECS:226-098-7
Product Categories:Aromatic Aldehydes & Derivatives (substituted);organic synthesis and intermediates;Benzaldehyde;1
Mol File:5274-70-4.mol
3-Nitrosalicylaldehyde Structure
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
pka5.07±0.24(Predicted)
form Crystalline Powder
color Yellow to brown
Water Solubility slightly soluble
Sensitive Air Sensitive
InChI1S/C7H5NO4/c9-4-5-2-1-3-6(7(5)10)8(11)12/h1-4,10H
InChIKeyNUGOTBXFVWXVTE-UHFFFAOYSA-N
SMILESOc1c(C=O)cccc1[N+]([O-])=O
CAS DataBase Reference5274-70-4(CAS DataBase Reference)
NIST Chemistry ReferenceBenzaldehyde, 2-hydroxy-3-nitro-(5274-70-4)
EPA Substance Registry SystemBenzaldehyde, 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 TSCA listed
HS Code 29130000
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
3-Nitrosalicylaldehyde Usage And Synthesis
Chemical Propertiesyellow to brown crystalline powder
Uses2-Hydroxy-3-nitrobenzaldehyde may be used in the synthesis of 5-acetyl-4-aryl-6-methyl-1,2,3,4-tetrahydro pyrimidine.
General Description2-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
Salicylaldehyde

90-02-8

3-Nitrosalicylaldehyde

5274-70-4

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
Tag: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

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