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1-Fluoro-3-iodobenzene

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1-Fluoro-3-iodobenzene Basic information
Product Name:1-Fluoro-3-iodobenzene
Synonyms:3-Fluoroiodobenzene (stabilized with Copper chip);1-Fluoro-3-iodobenzene, 98+%;Benzene, 1-fluoro-3-iodo-;1-Iodo-3-fluorobenzene;3-Fluoro-1-iodobenzene;1-Fluoro-3-iodobenzene,99%;1-Fluoro-3-iodobenzene,97%;3-Fluoroiodobenzene, 97+%
CAS:1121-86-4
MF:C6H4FI
MW:222
EINECS:214-339-9
Product Categories:Fluorinated benzene series;Aryl;Halogenated Hydrocarbons;Aromatic Hydrocarbons (substituted) & Derivatives;Benzene series;Miscellaneous;Fluorine Compounds;Iodine Compounds;C6
Mol File:1121-86-4.mol
1-Fluoro-3-iodobenzene Structure
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.)
Fp 153 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
form Liquid
color Clear yellow or pink
Specific Gravity1.890
Sensitive Light Sensitive
BRN 2039305
InChIKeyVSKSBSORLCDRHS-UHFFFAOYSA-N
CAS DataBase Reference1121-86-4(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1-fluoro-3-iodo-(1121-86-4)
EPA Substance Registry Systemm-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 Information
ProviderLanguage
1-Fluoro-3-iodobenzene English
SigmaAldrich English
ACROS English
ALFA English
1-Fluoro-3-iodobenzene Usage And Synthesis
Chemical Propertiesclear yellow or pink liquid
Uses3-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 Description3-Fluoroiodobenzene participates in palladium-catalyzed hydroarylation of arylpropiolamides.
Synthesis
3-Fluoroaniline

372-19-0

1-Fluoro-3-iodobenzene

1121-86-4

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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