2-HYDROXY-5-IODO-BENZALDEHYDE Chemical Properties

Melting point:

98-100 °C (lit.)

Boiling point:

282.0±30.0 °C(Predicted)

Density 

30 g/mL at 25 °C(lit.)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2913000090

MSDS

• Language:English Provider:SigmaAldrich

2-HYDROXY-5-IODO-BENZALDEHYDE Usage And Synthesis

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

2-HYDROXY-5-IODO-BENZALDEHYDE(1761-62-2)Related Product Information

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