3-Iodobenzaldehyde Chemical Properties

Melting point:

57-60 °C (lit.)

Boiling point:

124-125°C 13mm

Density 

1.8576 (estimate)

Flash point:

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

InChIKey

RZODAQZAFOBFLS-UHFFFAOYSA-N

CAS DataBase Reference

696-41-3(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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Iodobenzaldehyde Usage And Synthesis

Chemical Properties

Pale yellow crystalline powder

Uses

3-Iodobenzaldehyde is used as an organic reagent.

General Description

3-Iodobenzaldehyde can be prepared by the iodination of benzaldehyde using 1,3-diiodo-5,5-dimethylhydantoin in sulfuric acid.

Synthesis

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

3-Iodobenzaldehyde(696-41-3)Related Product Information

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• 3,5-DIIODO-4-HYDROXYBENZALDEHYDE
• 3,5-Diiodosalicylic acid
• 3,5-DIIODOSALICYLALDEHYDE
• 5-Iodovanillin
• 3,4,5-Triiodobenzoic acid
• 2,3,5-Triiodobenzoic acid
• 3-Iodobenzoic acid
• 2-HYDROXY-3-METHOXY-5-IODOBENZALDEHYDE
• 3,5-DIIODO-4-HYDROXYBENZOIC ACID
• 4-Amino-3,5-diiodobenzoic acid
• 5-Iodosalicylic acid
• METHYL 5-IODOSALICYLATE
• 3-Iodo-4-methylbenzoic acid
• 2-AMINO-3,5-DIIODOBENZOIC ACID
• 6-FLUORO-2-IODOBENZALDEHYDE
• 2-FLUORO-5-IODOBENZALDEHYDE 97,2-Fluoro-5-iodobenzaldehyde
• 3,5-Diiodobenzaldehyde