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1-Fluoro-3,3-dimethyl-1,2-benziodoxole
(CAS RN:1391728-13-4 Product Number:F0957)

Structure

1-Fluoro-3,3-dimethyl-1,2-benziodoxole

General Information

Product Number F0957

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Purity/Analysis Method >98.0%(T)
Storage Temperature
M.F. / M.W. C9H10FIO=280.08
CAS RN 1391728-13-4
Related CAS RN
MDL Number
  • Product Details
  • Safety & Regulations
  • Reference & Application

Specification

Purity(Iodometric Titration) min. 98.0 %
Melting point 85.0 to 89.0 deg-C

References

Reaxys-RN 23779593
PubChem SID 253661001

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P264
  • :Wash hands and face thoroughly after handling.
  • P280
  • :Wear protective gloves, eye protection.
  • P302+P352+P332+P313+P362+P364
  • :If on skin: Wash with plenty of soap and water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.
  • P305+P351+P338+P337+P313
  • :If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

Transport Information

HS Number 2934.99.4400

Application

An Air- and Moisture- stable Electrophilic Fluorinating Reagent

Monofluorination of β-ketoesters1) : Ethyl 3-oxo-3-phenylpropanoate (0.062 mL, 0.357 mmol) is added to a solution of 1-fluoro-3,3-dimethyl-1,2-benziodoxole 1 (0.200 g, 0.715 mmol) in Et3N・3HF (0.71 M solution in dichloromethane, 1.4 mL, 0.96 mmol). The flask is then sealed and heated to 40 °C for 24 hours. After the reaction, the reaction mixture is cooled to room temperature and a saturated solution of NaHCO3 (4 mL) is added. The organic layer is separated and the aqueous layer is extracted with more dichloromethane (3 x 5 mL). The organic layers are then combined, dried and concentrated. The crude product is purified by column chromatography (silica gel, eluent: EtOAc/Hexane = 5/95) to provide 2 as a yellow oil (0.106 g, 0.225 mmol, 63%).

References

Hypervalent Iodine-Catalyzed Balz–Schiemann Fluorination

F0957_04

3-Ethoxycarbonylbenzenediazonium tetrafluoroborate (132.0 mg, 0.5 mmol), 1-fluoro-3,3-dimethyl-1,2-benziodoxole (28.0 mg, 0.1 mmol) and a solution of BF3·OEt2 (0.1 mmol) in benzotrifluoride (5.0 mL) are charged into flask. The mixture is sealed. Stirred for 36 h at 45 °C, the mixture is directly purified through column chromatography on silica gel with petroleum ether : diethyl ether = 40:1 as the eluent to give ethyl 3-fluorobenzoate as a colorless oil (58.2 mg, 70%).

References

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