2-IODOBENZALDEHYDE Chemical Properties

Melting point:

36-39 °C (lit.)

Boiling point:

129 °C (14 mmHg)

Density 

1.8576 (estimate)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

Low Melting Crystalline Mass or Powder

color 

White to light beige

Sensitive 

Light Sensitive

BRN 

1927296

InChI

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

InChIKey

WWKKTHALZAYYAI-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=CC=C1I

CAS DataBase Reference

26260-02-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT, AIR SENSITIVE, KEEP COLD

HS Code 

29130000

MSDS

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

2-IODOBENZALDEHYDE Usage And Synthesis

Chemical Properties

white to light beige low melting crystalline

Uses

2-Iodo-benzaldehyde is a very useful synthetic intermediate. It is halogenated Benzaldehyde (B119740) which is mainly used as a precursor to other organic compounds, such as pharmaceuticals, and plastic additives.

Uses

2-Iodobenzaldehyde may be used as a reactant in the synthesis of the following heterocycles:

• 2,3-diaryl-1-indenones
• indolo[1,2-a]quinazolines
• Baylis-Hillman (BH) adducts

• 5-phenylindazolo[3,2-b]quinazolin-7(5H)-one
• 4-(3-iodophenyl)-2,2:6,2-terpyridine
• fluoren-9-one
• 2-formyl-3′-methoxybiphenyl

General Description

2-Iodobenzaldehyde (o-iodobenzaldehyde) is a 2-halobenzaldehyde derivative. Its crystals belong to the orthorhombic crystal system and P2₁2₁2₁ space group.

Synthesis

General procedure for the synthesis of 2-iodobenzaldehyde from 2-formylphenylboronic acid: 2-formylphenylboronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol), (CF3)2CFI (0.178 g, 0.6 mmol) and DMF (2 mL) were added to a closed tube with a rubber stopper. The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the resulting suspension was poured into water and extracted with ethyl acetate. The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using petroleum ether/ethyl acetate (20:1, v/v) as eluent to give 0.086 g of 2-iodobenzaldehyde as a light yellow solid (0.35 mmol, 87% yield).

References

[1] Journal of Fluorine Chemistry, 2016, vol. 189, p. 59 - 67

2-IODOBENZALDEHYDE(26260-02-6)Related Product Information

• Acetrizoic acid
• 2-FLUORO-6-IODOBENZOIC ACID
• Methyl 2-iodobenzoate
• 2-Iodobenzoic acid
• 1-BROMO-3-(1,3-DIOXOLAN-2-YL)-4-FLUOROBENZENE
• 2,3,5-Triiodobenzoic acid
• 2-Iodosobenzoic acid
• 2-IODOBENZALDEHYDE
• Metrizamide
• 2-IODOBENZOYL CHLORIDE
• 3-Amino-2,4,6-triiodobenzoic acid
• 3-HYDROXY-2,4,6-TRIIODOBENZOIC ACID
• 2'-IODOHIPPURIC ACID
• 2-Iodoxybenzoic acid
• 5-BROMO-2-IODOBENZALDEHYDE
• 2-HYDROXY-3-METHOXY-5-IODOBENZALDEHYDE
• 2-BROMO-4-IODOBENZALDEHYDE
• 3-HYDROXY-4-IODOBENZALDEHYDE