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3-Iodobenzaldehyde

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3-Iodobenzaldehyde Basic information
Product Name:3-Iodobenzaldehyde
Synonyms:3-IODOBENZALDEHYDE;3-Iodobenzaldehyde 99%;3-IODOBENZALDEHYDE, 99+%;1-Formyl-3-iodobenzene;3-Iodobenzaldehyde>;m-Iodobenzaldehyde;Benzaldehyde, 3-iodo-;13C6]-3-Iodobenzaldehyde
CAS:696-41-3
MF:C7H5IO
MW:232.02
EINECS:626-706-4
Product Categories:Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Adehydes, Acetals & Ketones;Iodine Compounds;Aldehydes;C7;Carbonyl Compounds
Mol File:696-41-3.mol
3-Iodobenzaldehyde Structure
3-Iodobenzaldehyde Chemical Properties
Melting point 57-60 °C (lit.)
Boiling point 124-125°C 13mm
density 1.8576 (estimate)
Fp 124-125°C/13mm
storage temp. 2-8°C
form Crystalline Powder, Crystals or Needles
color White to pale yellow
Water Solubility Slightly soluble in water.
Sensitive Air & Light Sensitive
BRN 1854653
InChIKeyRZODAQZAFOBFLS-UHFFFAOYSA-N
CAS DataBase Reference696-41-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
Hazard Note Irritant
HazardClass IRRITANT, AIR SENSITIVE, KEEP COLD
HS Code 29130000
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
3-Iodobenzaldehyde Usage And Synthesis
Chemical PropertiesPale yellow crystalline powder
Uses3-Iodobenzaldehyde is used as an organic reagent.
General Description3-Iodobenzaldehyde can be prepared by the iodination of benzaldehyde using 1,3-diiodo-5,5-dimethylhydantoin in sulfuric acid.
Synthesis
3-IODOBENZYL ALCOHOL

57455-06-8

3-Iodobenzaldehyde

696-41-3

3-Iodobenzaldehyde (12) was synthesized as follows: pyridinium chlorochromate (2.45 g, 11.4 mmol) and dry diatomaceous earth (about 2.00 g) were suspended in anhydrous dichloromethane (20 ml) at room temperature and stirred for 15 minutes. Subsequently, a solution of 3-iodobenzyl alcohol (11) (1.02 g, 4.35 mmol) in anhydrous dichloromethane (5 ml) was added to this suspension. The reaction mixture was protected from light and stirring was continued for 2 hours at room temperature. After completion of the reaction, the reaction solution was diluted with ether and filtered through diatomaceous earth. The resulting turbid brown filtrate was concentrated to a reddish brown gelatinous paste, which was redissolved in dichloromethane and purified by short silica gel column chromatography using dichloromethane as eluent. A clarified colorless solution was finally obtained, and 3-iodobenzaldehyde (12) was concentrated to give 3-iodobenzaldehyde (12) as a white solid (0.953 g, 95% yield).1H NMR (400 MHz, CDCl3) data were as follows: δ 7.29 (t, J = 7.8 Hz, 1H, H5); 7.85 (br d, J = 7.8 Hz, 1H, H6); 7.96 (br d, J =7.8 Hz, 1H, H4); 8.21 (br s, 1H, H2); 9.93 (s, 1H, CHO).

References[1] Advanced Synthesis and Catalysis, 2004, vol. 346, # 7, p. 767 - 776
[2] Patent: WO2005/82894, 2005, A1. Location in patent: Page/Page column 41-42
[3] Bulletin of the Chemical Society of Ethiopia, 2013, vol. 27, # 1, p. 131 - 136
[4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 20, p. 3047 - 3052
[5] Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 585 - 596
Tag:3-Iodobenzaldehyde(696-41-3) Related Product Information
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