1-Fluoro-3-iodobenzene Chemical Properties

Melting point:

-42°C

Boiling point:

77-78 °C/19 mmHg (lit.)

Density 

1.89 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.584(lit.)

Flash point:

153 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

Specific Gravity

1.890

color 

Clear yellow or pink

Sensitive 

Light Sensitive

BRN 

2039305

InChIKey

VSKSBSORLCDRHS-UHFFFAOYSA-N

CAS DataBase Reference

1121-86-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-fluoro-3-iodo-(1121-86-4)

EPA Substance Registry System

m-Fluoroiodobenzene (1121-86-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29039990

MSDS

• Language:English Provider:1-Fluoro-3-iodobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1-Fluoro-3-iodobenzene Usage And Synthesis

Chemical Properties

clear yellow or pink liquid

Uses

3-Fluoroiodobenzene was used to prepare methyl 4-iodobenzo[b]thiophene-2-carboxylate, key intermediate for the synthesis of 4-substituted benzo[b]thiophene-2-carboxamidines.

General Description

3-Fluoroiodobenzene participates in palladium-catalyzed hydroarylation of arylpropiolamides.

Synthesis

The general procedure for the synthesis of m-fluoroiodobenzene from 3-fluoroaniline was as follows: an aqueous solution (20 mL) of NaNO2 (6.4 g, 92.75 mmol) was slowly added dropwise at 0 °C to a solution of 3-fluoroaniline (10 g, 90.09 mmol) dissolved in 32% H2SO4 (179 g). The reaction mixture was stirred continuously at 0 °C for 1 hour. Subsequently, an aqueous solution (30 mL) of KI (22.4 g, 134.94 mmol) was added while maintaining 0 °C and stirring was continued at 0 °C for 1 hour. After completion of the reaction, the aqueous phase was extracted with EtOAc (2 x 250 mL). The organic phases were combined and washed sequentially with water (5×200mL) and 10% NaHSO3 solution (3×200mL), dried over Na2SO4 and concentrated under reduced pressure to remove the solvent, yielding 17.7 g of 1-fluoro-3-iodobenzene as a yellow solid in 82% yield.

References

[1] Patent: WO2008/103615, 2008, A1. Location in patent: Page/Page column 40
[2] Journal of the American Chemical Society, 1963, vol. 85, p. 709 - 724

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