| Identification | More | [Name]
2-HYDROXY-5-IODO-BENZALDEHYDE | [CAS]
1761-62-2 | [Synonyms]
2-HYDROXY-5-IODO-BENZALDEHYDE
5-IODOSALICYLALDEHYDE
AKOS B028970
LABOTEST-BB LT00137782
SALOR-INT L497630-1EA
Iodosalicylaldehyde,5-
5-IODO-2-HYDROXYBENZALDEHYDE | [EINECS(EC#)]
625-766-9 | [Molecular Formula]
C7H5IO2 | [MDL Number]
MFCD00723501 | [Molecular Weight]
248.02 | [MOL File]
1761-62-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
98-100 °C (lit.) | [Boiling point ]
282.0±30.0 °C(Predicted) | [density ]
30 g/mL at 25 °C(lit.)
| [storage temp. ]
Store Cold | [pka]
7.56±0.18(Predicted) | [Appearance]
Light brown to yellow Solid | [Sensitive ]
Light Sensitive | [InChI]
InChI=1S/C7H5IO2/c8-6-1-2-7(10)5(3-6)4-9/h1-4,10H | [InChIKey]
PDFVIWFKGYODKD-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC(I)=CC=C1O | [CAS DataBase Reference]
1761-62-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
2913000090 |
| Hazard Information | Back Directory | [Uses]
5-Iodosalicylaldehyde may be used to synthesize:
- 5-formylsalicylaldehyde
- 5-ortho-carboranylsalicylaldehyde
- new salen (N,N′-Bis(salicylidene)ethylenediamine) ligands that are tethered to a p-acylthio(phenylacetylene)n linker
| [General Description]
5-Iodosalicylaldehyde is a salicylaldehyde derivative. | [Synthesis]
General procedure for the synthesis of 5-iodosalicylaldehyde from salicylaldehyde: To a stirred solution of salicylaldehyde (1 mmol) in dichloromethane (CH2Cl2) or 1,2-dichloroethane ((CH2Cl)2) (0.1 M) was added triphenylphosphorane bis(trifluoromethylsulfonyl)imide (Ph3PAuNTf2) (0.025 mmol, 19 mg; if toluene-ligated Ph3PAuNTf2 complex, the ratio was 2:1), followed by the addition of N-iodosuccinimide (NIS) (1.1 mmol, 248 mg). The reaction mixture was stirred at room temperature or reacted under reflux conditions until complete conversion of salicylaldehyde was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the resulting crude product was purified by fast column chromatography using different ratios of hexane and ethyl acetate (EtOAc) as eluents to finally obtain purified 5-iodosalicylaldehyde. | [References]
[1] Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4306 - 4312
[2] Synlett, 2014, vol. 25, # 3, p. 399 - 402
[3] European Journal of Organic Chemistry, 2016, vol. 2016, # 12, p. 2177 - 2186
[4] Angewandte Chemie - International Edition, 2007, vol. 46, # 4, p. 572 - 575
[5] Chemistry - A European Journal, 2013, vol. 19, # 7, p. 2442 - 2449 |
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