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CAS RN: 140681-55-6 | Product Number: F0358

N-Fluoro-N'-(chloromethyl)triethylenediamine Bis(tetrafluoroborate)


Purity: >95.0%(T)
Synonyms:
  • 1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate)
  • F-TEDA-BF4
Documents:
5G
$32.00
Contact Us Contact Us ≥40 
25G
$94.00
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100G
$281.00
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Product Number F0358
Purity / Analysis Method >95.0%(T)
Molecular Formula / Molecular Weight C__7H__1__4B__2ClF__9N__2 = 354.26 
Physical State (20 deg.C) Solid
Store Under Inert Gas Store under inert gas
Condition to Avoid Moisture Sensitive
CAS RN 140681-55-6
Reaxys Registry Number 5368649
PubChem Substance ID 87570129
Merck Index (14) 8425
MDL Number

MFCD00142607

Specifications
Appearance White to Light yellow powder to crystal
Purity(Iodometric Titration) min. 95.0 %
Properties (reference)
Melting Point 175 °C
Solubility in water Soluble
GHS
Pictogram Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H302 : Harmful if swallowed.
H318 : Causes serious eye damage.
H317 : May cause an allergic skin reaction.
H412 : Harmful to aquatic life with long lasting effects.
H251 : Self-heating; may catch fire.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P261 : Avoid breathing dust/ fume/ gas/ mist/ vapors/ spray.
P273 : Avoid release to the environment.
P270 : Do not eat, drink or smoke when using this product.
P235 + P410 : Keep cool. Protect from sunlight.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P272 : Contaminated work clothing must not be allowed out of the workplace.
P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.
P333 + P313 : If skin irritation or rash occurs: Get medical advice/ attention.
P363 : Wash contaminated clothing before reuse.
P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
P407 : Maintain air gap between stacks/ pallets.
P420 : Store away from other materials.
Related Laws:
Transport Information:
UN Number (DOT-AIR) UN3088
Class (DOT-AIR) 4.2
Packing Group (TCI-A) II
HS Number 2933.99.9701
Application
TCI Practical Example: Fluorination of 1,3-Dicarbonyl Compound Using F-TEDA-BF4

TCI反応実例:F-TEDA-BF4を用いたフッ素化反応

Used Chemicals

Procedure

To a solution of acetoacetanilide (194 mg, 1.1 mmol) in acetonitrile and water (1:1, 4 mL) was added F-TEDA-BF4 (778 mg, 2.2 mmol). The reaction mixture was stirred at r.t. for 24 hours. Then solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 0:1 - 1:9 on silica gel) to give 2,2-difluoro-3-oxo-N-phenylbutanamide as a light yellow liquid (214 mg,y. 92%).

Experimenter’s Comments

The reaction mixture was monitored by LC.

Analytical Data

2,2-Difluoro-3-oxo-N-phenylbutanamide

1H NMR (270 MHz, CDCl3); δ 7.97 (brs, 1H), 7.57-7.53 (m, 2H), 7.38 (t, 2H, J = 8.1 Hz), 7.25-7.18 (m, 1H), 6.60 (t, 1H, J = 73 Hz), 2.52 (t, 3H, J = 1.6 Hz).

Lead Reference


Application
Metal-Free Fluorination of C(sp3)-H Bonds using a Catalytic N-Oxyl Radical

D4413

Typical Procedure: To a solution of 4-phenylbutyl benzoate (55.6 mg, 0.219 mmol) and NDHPI (1.36 mg, 0.00547 mmol) in MeCN (2.2 mL) is added F-TEDA-BF4 (155 mg, 0.438 mmol) at room temperature. The mixture is degassed by freeze-thaw for 3 times under Ar atmosphere, and stirred at 50 °C for 5 h. The reaction mixture is then neutralized with saturated aqueous NaHCO3, and extracted with EtOAc (3 mL×3). The combined organic layers are dried over Na2SO4, and concentrated. The residue is purified with flash column chromatography (silica gel, hexane : Et2O=30 : 1) to provide 4-benzoyloxy-1-phenylbutyl fluoride (43.1 mg, Y. 72%).

References


Application
Regioselective Fluorohydroxylation Reaction of Arylallenes

Reference


Application
Regiospecific fluorination of functionalized phenols

Typical procedue: To 4-(biphenyl)tributylstananne (44.3 mg) in acetone (2.0 mL) at 23°C is added silver triflate (51.4 mg) and N-fluoro-N'-(chloromethyl)triethylenediamine bis(tetrafluoroborate) (F-TEDA-BF4) (42.5 mg). The reaction mixture is stirred for 20 min at 23°C and then concentrated in vacuo. The residue is purified by preparative TLC eluting with hexane to give 12.0 mg of the fluorinated compound as colorless solid (70% yield).

References


PubMed Literature


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