4-Iodobenzaldehyde Chemical Properties

Melting point:

78-82 °C (lit.)

Boiling point:

265°C(lit.)

Density 

1.8576 (estimate)

storage temp. 

2-8°C

form 

Crystals

color 

Yellow

Water Solubility 

Insoluble in water.

Sensitive 

Air & Light Sensitive

BRN 

636101

InChI

InChI=1S/C7H5IO/c8-7-3-1-6(5-9)2-4-7/h1-5H

InChIKey

NIEBHDXUIJSHSL-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(I)C=C1

CAS DataBase Reference

15164-44-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT, AIR SENSITIVE, KEEP COLD

HS Code 

29130000

MSDS

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

4-Iodobenzaldehyde Usage And Synthesis

Chemical Properties

Yellow crystals

Uses

4-Iodobenzaldehyde is used in synthesis of 4-[2-(trimethylsilyl)ethynyl]benzaldehyde, 5,15-dimesityl-10-(3-[2-(trimethylsilyl)ethynyi]phenyl}-20-(4-iodophenyl)porphyrin, and 5,15-dimesityl-10-[3,5-bis{2-[4-(N,N?-difluoroboryl-1,9-dimethyidipyrrin-5-yl)-phenyl]ethynyl}phenyl]-20-(4-iodophenyl)porphyrin.

Uses

4-Iodobenzaldehyde has been used in the preparation of:

• benzaldimine monolayers
• 4-[2-(trimethylsilyl)ethynyl]benzaldehyde
• 5,15-dimesityl-10-(3-[2-(trimethylsilyl)ethynyi]phenyl}-20-(4-iodophenyl)porphyrin
• 5,15-dimesityl-10-[3,5-bis{2-[4-(N,N′-difluoroboryl-1,9-dimethyidipyrrin-5-yl)-phenyl]ethynyl}phenyl]-20-(4-iodophenyl)porphyrin, multipigment building block

Synthesis

A mixture of 10.0g p-bromobenzaldehyde (54mmol), 81.1gKI (488mmol, 9.0eq), 31.7gCuI (166mmol, 3.1eq) and 150ml freshly distilled DMI was placed in a 500ml three-neck flask. The mixture was purged with nitrogen and heated at 200°C with vigorous stirring for 6 hours. After cooling to room temperature, add salt water and ice. The reaction vessel was placed in an ice bath for several hours and precipitated inorganic salts were removed by filtration. After the filtrate was extracted with diethyl ether, the extracts were combined and washed with brine. Removal of the solvent under reduced pressure gave the product 4-Iodobenzaldehyde.

4-Iodobenzaldehyde (15164-44-0)Related Product Information

• 4-Iodobenzoic acid
• 4-Iodoanisole
• Acetrizoic acid
• DIATRIZOIC ACID
• sodium acetrizoate
• IODIPAMIDE
• 4'-Iodoacetophenone
• Methyl 4-iodobenzoate
• 4-Iodobenzoyl chloride
• 3,4,5-Triiodobenzoic acid
• 3-HYDROXY-2,4,6-TRIIODOBENZOIC ACID
• 3-Amino-2,4,6-triiodobenzoic acid
• Ethyl 4-iodobenzoate
• Metrizamide
• MEGLUMINE DIATRIZOATE
• 4-IODOBENZALDEHYDE
• Diatrizoate sodium
• 2-Hydroxy-3-iodobenzaldehyde