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CAS RN: 185739-14-4 | Product Number: D6545

2,2-Difluoroethenyl 4-Methylbenzene-1-sulfonate

Chemical Structure of 2,2-Difluoroethenyl 4-Methylbenzene-1-sulfonate

Purity: >98.0%(GC)
Synonyms:
  • 2,2-Difluorovinyl 4-Methylbenzenesulfonate
  • 2,2-Difluorovinyl Tosylate
  • Toluene-4-sulfonic Acid 2,2-Difluorovinyl Ester
Product Documents:
1G
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5G
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Product Number D6545
Purity / Analysis Method >98.0%(GC)
Molecular Formula / Molecular Weight C__9H__8F__2O__3S = 234.22 
Physical State (20 deg.C) Liquid
Storage Temperature Refrigerated (0-10°C)
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive,Moisture Sensitive,Heat Sensitive
CAS RN 185739-14-4
Reaxys Registry Number 7638656
MDL Number

MFCD27946567

Specifications
Appearance Colorless to Light yellow clear liquid
Purity(GC) min. 98.0 %
NMR confirm to structure
Properties (reference)
Flash point 115 °C
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
Related Laws:
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Application
TCI Practical Example: Suzuki-Miyaura Cross-Coupling of Aromatic Boronic Acids Using a Novel Difluorovinylating Agent

TCI Practical Example: Suzuki-Miyaura Cross-Coupling of Aromatic Boronic Acids Using a Novel Difluorovinylating Agent

Used Chemicals

Procedure

4-Biphenylboronic acid (100 mg, 0.51 mmol), 2,2-difluorovinyl tosylate (177 mg, 0.76 mmol), Pd2(dba)3 (11.5 mg, 0.01 mmol), and PCy3·HBF4 (9.2 mg, 0.03 mmol) were added into the reaction vessel. To this, tripotassium phosphate (182 mg, 0.86 mmol) in water (670 µL) and THF (3.4 mL) were added subsequentially. The vessel was purged with nitrogen and the mixture was stirred at 70 °C for 20 hours. Then the reaction mixture was filtered under vacuum to remove the insoluble, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) to afford 4-(2,2-difluorovinyl)biphenyl (93.8 mg, 88% yield) as a white solid.

Experimenter’s Comments

The reaction was monitored by TLC (hexane, Rf = 0.4) and UPLC-MS.

Analytical Data

4-(2,2-Difluorovinyl)biphenyl

1H NMR (400 MHz, CDCl3); δ 7.61- 7.57 (m, 4H), 7.46- 7.33 (m, 5H), 5.32 (dd, J = 26.4, 3.6 Hz, 1H).

Lead Reference


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