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Published TCIMAIL newest issue No.197
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CAS RN: 140681-55-6 | Product Number: F0358
N-Fluoro-N'-(chloromethyl)triethylenediamine Bis(tetrafluoroborate)
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Purity: >95.0%(T)
Synonyms:
- 1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate)
- F-TEDA-BF4
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 5G |
€26.00
|
8 | ≥100 |
|
| 25G |
€86.00
|
7 | ≥100 |
|
| 100G |
€231.00
|
3 | ≥100 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| 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 |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| 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 |
|
| 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 | P261 : Avoid breathing dust. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. 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 or pallets. P413 : Store bulk masses greater than .? kg/ .? lbs at temperatures not exceeding .? °C/ .? °F. |
Related Laws:
Transport Information:
| UN Number | UN3088 |
| Class | 4.2 |
| Packing Group | II |
| HS Number | 2933599565 |
Application
TCI Practical Example: Fluorination of 1,3-Dicarbonyl Compound Using F-TEDA-BF4
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Used Chemicals
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Procedure
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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%).
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Experimenter’s Comments
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The reaction mixture was monitored by LC.
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Analytical Data
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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).
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Lead Reference
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- Chemoselective Mono- and Difluorination of 1,3-Dicarbonyl Compounds
Application
Metal-Free Fluorination of C(sp3)-H Bonds using a Catalytic N-Oxyl Radical
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
- Metal-free fluorination of C(sp3)-H bonds using a catalytic N-oxyl radical
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
Articles/Brochures
TCIMAIL
[TCI Practical Example] Fluorination Using F-TEDA-BF4[Research Articles] Metal-Free Fluorination of C(sp3)-H Bonds using a Catalytic N-Oxyl Radical
[TCI Practical Example] The Deoxyfluorination of Alcohol Using a Photoredox Catalyst
Product Documents (Note: Some products will not have analytical charts available.)
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