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Published TCIMAIL newest issue No.198

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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

Product Documents:

Size	Unit Price	Belgium	Japan*
5G	€26.00	13	≥100
25G	€86.00	9	≥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).

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General Information plus

Product Number	F0358
Purity / Analysis Method	>95.0%(T)
Molecular Formula / Molecular Weight	C₇H₁₄B₂ClF₉N₂ = 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 & Properties plus

Safety & Regulations plus

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

Applications & Literature plus

Application

TCI Practical Example: Fluorination of 1,3-Dicarbonyl Compound Using F-TEDA-BF₄

Used Chemicals

Acetoacetanilide [A0046]
N-Fluoro-N'-(chloromethyl)triethylenediamine Bis(tetrafluoroborate) (= F-TEDA-BF₄) [F0358]
Acetonitrile
Water

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

Chemoselective Mono- and Difluorination of 1,3-Dicarbonyl Compounds

L. Tang, Z. Yang, J. Jiao, Y. Cui, G. Zou, Q. Zhou, Y. Zhou, W. Rao, X. Ma, J. Org. Chem. 2019, 84, 10449.

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

Metal-free fluorination of C(sp³)-H bonds using a catalytic N-oxyl radical
- Y. Amaoka, M. Nagatomo, M. Inoue, Org. Lett. 2013, 15, 2160.

Application

Regioselective Fluorohydroxylation Reaction of Arylallenes

Reference

C. Zhou, J. Li, B. Lu, C. Fu, S. Ma, Org. Lett. 2008, 10, 581.

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

T. Furuya, A. E. Strom, T. Ritter, J. Am. Chem. Soc. 2009, 131, 1662.

PubMed Literature

Articles/Brochures

Quaternary Ammonium Salts

Sulfur Dioxide (SO2) Surrogate Reagents Usable for Sulfonylation

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

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Appearance	White to Light yellow powder to crystal
Purity(Iodometric Titration)	min. 95.0 %

Melting Point	175 °C
Solubility in water	Soluble

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

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

Used Chemicals

Procedure

Experimenter’s Comments

Analytical Data

Lead Reference

References

Reference

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Safety Data Sheet (SDS)

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

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

Used Chemicals

Procedure

Experimenter’s Comments

Analytical Data

Lead Reference

References

Reference

References

Articles/Brochures

Safety Data Sheet (SDS)

Specifications

C of A & Other Certificates

Sample C of A

Analytical Charts

Other Documents

Product Categories

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Chemistry

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Chemistry