2-Iodobenzyl alcohol Chemical Properties

Melting point:

89-92 °C (lit.)

Boiling point:

145°C/10mmHg(lit.)

Density 

1.7904 (estimate)

refractive index 

1.6349

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Needle-Like Powder

pka

14.01±0.10(Predicted)

color 

White to yellow or pinkish

Water Solubility 

Insoluble in water.

Sensitive 

Light Sensitive

BRN 

2079487

InChI

InChI=1S/C7H7IO/c8-7-4-2-1-3-6(7)5-9/h1-4,9H,5H2

InChIKey

WZCXOBMFBKSSFA-UHFFFAOYSA-N

SMILES

C1(CO)=CC=CC=C1I

CAS DataBase Reference

5159-41-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38-36/37/38

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

F 

8-10

HS Code 

29062990

MSDS

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

2-Iodobenzyl alcohol Usage And Synthesis

Chemical Properties

white to yellow or pinkish needle-like powder

Uses

2-Iodobenzyl alcohol was used in the synthesis of substituted seven-membered lactones, 2-[(E)-(1?-iodo-2?-propenyl)]benzyl alcohol2 and 2,3-diphenyl-1-indenone.

Uses

2-Iodobenzyl alcohol was used in the synthesis of:

• substituted seven-membered lactones
• 2-[(E)-(1′-iodo-2′-propenyl)]benzyl alcohol
• 2,3-diphenyl-1-indenone

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 3052, 1974 DOI: 10.1021/jo00934a028

Synthesis

The general procedure for the synthesis of 2-iodobenzyl alcohol from 2-iodobenzoic acid was as follows: to a tetrahydrofuran (THF) solution (16 mL) of commercially available o-iodobenzoic acid (4.15 g, 16.8 mmol) was slowly added borane-dimethyl sulfide complex (1.90 mL, 20.0 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 15 hours before the reaction was quenched by the addition of phosphate buffer (pH 7). Subsequently, the reaction mixture was extracted three times with ethyl acetate and the organic phases were combined. The organic phase was washed with saturated brine and dried with anhydrous sodium sulfate. Concentration under reduced pressure to remove the solvent gave o-iodobenzyl alcohol (3.84 g, 98% yield) as a white solid, which could be used in the next reaction without further purification. The crude o-iodobenzyl alcohol (3.77 g, 16.1 mmol) was added to a dichloromethane (DCM, 33 mL) suspension of dimethyl sulfoxide (DMSO, 14.0 g, 161 mmol). The reaction mixture was stirred at room temperature for 30 h before being filtered through a diatomaceous earth pad, using dichloromethane as the eluent. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 5:1) to afford o-iodobenzaldehyde (3.36 g, 90% yield) as light yellow crystals.

References

[1] Chemistry - A European Journal, 2018, vol. 24, # 70, p. 18653 - 18657
[2] Tetrahedron Letters, 1987, vol. 28, # 2, p. 171 - 174
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 15, p. 4669 - 4678
[4] Organic Letters, 2015, vol. 17, # 5, p. 1126 - 1129
[5] Journal of Fluorine Chemistry, 2015, vol. 179, p. 106 - 115

2-Iodobenzyl alcohol(5159-41-1)Related Product Information

• Ethyl acetate
• Ioversol
• Iodixanol
• (Diacetoxyiodo)benzene
• 1-Bromo-4-iodobenzene
• 1,4-Diiodobenzene
• Phenethyl alcohol
• Benzyl alcohol
• 4-Nitrobenzyl alcohol
• 4-Iodoanisole
• N1,N3-Bis(1,3-dihydroxypropan-2-yl)-5-(2-hydroxypropanamido)-2,4,6-triiodoisophthalamide
• 2,3,5-Triiodobenzoic acid
• 2-Iodosobenzoic acid
• 3-Amino-2,4,6-triiodobenzoic acid
• 3-HYDROXY-2,4,6-TRIIODOBENZOIC ACID
• 2-Iodobenzoic acid
• sodium acetrizoate
• 2-Iodoxybenzoic acid