659-18-7

Usage

Uses

Used in Pharmaceutical Industry:
TRIS(2,2,2-TRIFLUOROETHYL) BORATE is used as a therapeutic agent for the treatment of hypertension and glaucoma. Its selective blocking of beta1 adrenergic receptors helps in managing high blood pressure and reducing intraocular pressure, which are common issues in these conditions.
Used in Chemical Synthesis:
TRIS(2,2,2-TRIFLUOROETHYL) BORATE is used as a reagent to promote the direct formation of amides from carboxylic acids and amines under thermal and microwave conditions. This application is particularly useful in the synthesis of various organic compounds and pharmaceuticals, as it simplifies the process and increases the efficiency of amide bond formation.

InChI:InChI=1/C6H6BF9O3/c8-4(9,10)1-17-7(18-2-5(11,12)13)19-3-6(14,15)16/h1-3H2

Synthetic route

2,2,2-trifluoroethanol (75-89-8) → tris(2,2,2-trifluoroethyl) borate (659-18-7)

Conditions	Yield
With boron tribromide at -78 - 70℃; Inert atmosphere; Neat (no solvent);	90%
With boron trioxide at 80℃; for 8h;	48%
With boron trichloride; pentane at -80℃;
With boron trioxide
With boron trichloride In Petroleum ether

boron trioxide + 2,2,2-trifluoroethanol (75-89-8) → tris(2,2,2-trifluoroethyl) borate (659-18-7)

Conditions	Yield
at 80℃; under 760.051 Torr; for 24h;	44%

2,2,2-trifluoroethanol (75-89-8) + boron trichloride (10294-34-5) → tris(2,2,2-trifluoroethyl) borate (659-18-7)

Conditions	Yield
With n-butyllithium In diethyl ether 0°C, allowing to warm to room temp. after addn. of OHCH2CF3 and n-C4H9Li, stirring for 1 h, recooling to -78°C, addn. of BCl3, molar ratio of C6H5BCl2:OHCH2CF3:n-C4H9Li=1:3:3, stirring overnight;	36%

BF3*CH3SH + 2,2,2-trifluoroethanol (75-89-8) → tris(2,2,2-trifluoroethyl) borate (659-18-7)

Conditions	Yield
In neat (no solvent) mixing (-20°C, over 15 min), stirring (room temp., 12 h); pentane addn., fractional distn.;

picoline (108-89-4) + tris(2,2,2-trifluoroethyl) borate (659-18-7) → [B(CH2CF3)3][4-methylpyridine]

Conditions	Yield
In diethyl ether B compd. was added with stirring to methylpyridine in Et2O under N2; stirred for 20 min; solvent removed (vac.);	84%

tris(2,2,2-trifluoroethyl) borate (659-18-7) + boron trichloride (10294-34-5) → Cl2BOCH2CF3 (131252-33-0) + ClB(OCH2CF3)2 (131252-32-9)

Conditions	Yield
In pentane -78°C, molar ratio of B(OCH2CF3)3:BCl3=2:1, stirring overnight; fractional distn., elem. anal.;	A n/a B 36%

tris(2,2,2-trifluoroethyl) borate (659-18-7) → bis(trifluoromethylchloromethoxy)chloroborane (684-71-9)

Conditions	Yield
With chlorine Irradiation;

tris(2,2,2-trifluoroethyl) borate (659-18-7) → boric acid tris-(1-chloro-2,2,2-trifluoro-ethyl) ester (688-34-6)

Conditions	Yield
With chlorine Irradiation;

tris(2,2,2-trifluoroethyl) borate (659-18-7) + chlorine (7782-50-5) → bis(trifluoromethylchloromethoxy)chloroborane (684-71-9)

Conditions	Yield
Irradiation (UV/VIS); passing Cl2 into B(OCH2CF3)3, UV irradn. 25 h; distn.;

tris(2,2,2-trifluoroethyl) borate (659-18-7) + L-phenylalanine (63-91-2) → C13H13BF6NO4(1-)*H(1+)

Conditions	Yield
In [D3]acetonitrile at 40℃; for 0.5h; Reagent/catalyst; Sonication;

tris(2,2,2-trifluoroethyl) borate (659-18-7) + D-(R)-phenylalanine (673-06-3) → C13H13BF6NO4(1-)*H(1+)

Conditions	Yield
In [D3]acetonitrile at 40℃; for 0.5h; Reagent/catalyst; Sonication;

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 10294-34-5 boron trichloride 

Relevant academic research and scientific papers

Direct amidation of unprotected amino acids using B(OCH2CF3)3

A commercially available borate ester, B(OCH2CF3)3, can be used to achieve protecting-group free direct amidation of α-amino acids with a range of amines in cyclopentyl methyl ether. The method can be applied to the synthesis of medicinally relevant compounds, and can be scaled up to obtain gram quantities of products.

Direct synthesis of amides from carboxylic acids and amines using B(OCH2CF3)3

B(OCH2CF3)3, prepared from readily available B2O3 and 2,2,2-trifluoroethanol, is as an effective reagent for the direct amidation of a variety of carboxylic acids with a broad range of amines. In most cases, the amide products can be purified by a simple filtration procedure using commercially available resins, with no need for aqueous workup or chromatography. The amidation of N-protected amino acids with both primary and secondary amines proceeds effectively, with very low levels of racemization. B(OCH2CF3)3 can also be used for the formylation of a range of amines in good to excellent yield, via transamidation of dimethylformamide.

Borate esters as convenient reagents for direct amidation of carboxylic acids and transamidation of primary amides

Simple borates serve as effective promoters for amide bond formation with a variety of carboxylic acids and amines. With trimethyl or tris(2,2,2- trifluoroethyl) borate, amides are obtained in good to excellent yield and high purity after a simple work-up procedure. Tris(2,2,2-trifluoroethyl) borate can also be used for the straightforward conversion of primary amides to secondary amides via transamidation. The Royal Society of Chemistry 2011.

The synthesis of a new family of boron-based anion receptors and the study of their effect on ion pair dissociation and conductivity of lithium salts in nonaqueous solutions

A new family of anion receptors based on boron compounds has been synthesized. These compounds can be used as anion receptors in lithium battery electrolytes. This family includes various borane and borate compounds with different fluorinated aryl and fluorinated alkyl groups. When these anion receptors are used as additives in 1,2-dimethoxyethane (DME) solutions containing various lithium salts, the ionic conductivities of these solutions are greatly increased. The electrolytes tested in this study were DME solutions containing the following lithium salts: LiF, LiCl, LiBr, LiI, CF3COOLi, and C2F5COOLi. Without the additive, the solubility of LiF in DME (and all other nonaqueous solvents) is very low. With some of these boron compounds as additives, LiF solutions in DME with concentration as high as 1 M were obtained. The solubilities of the other salts were also increased by these additives. Near edge X-ray absorption fine structure (NEXAFS) spectroscopy studies show that Cl- and I- anions are complexed with these compounds in DME solutions containing LiCl or LiI salts. The degree of complexation is also closely related to the structures of the fluorinated aryl and alkyl groups, which act as electron-withdrawing groups. The NEXAFS results are in good agreement with ionic conductivity studies.