350-70-9

Basic information

• Product Name: BORON TRIS(TRIFLUOROACETATE)
• Synonyms: BORON TRIS(TRIFLUOROACETATE);Boron tris(trifluoroacetate) solution;tris(trifluoroacetoxy)borane;BORON TRIS(TRIFLUOROACETATE), 1.0M SOLUT ION IN TRIFLUOROACETIC ACID;Acetic acid, trifluoro-, trianhydride with boric acid (H3BO3);trifluoroacetic acid, trianhydride with boric acid;Tri(trifluoroacetoxy)borane;2,2,2-trifluoroacetic acid bis[(2,2,2-trifluoroacetyl)oxy]boranyl ester
• CAS NO: 350-70-9
• Molecular Formula: C₆BF₉O₆
• Molecular Weight: 349.86
• EINECS: 206-507-5
• Product Categories: Deprotecting Reagents;Others;Protection and Derivatization
• Mol File: 350-70-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 116.7°Cat760mmHg
• Flash Point: 24.4°C
• Appearance: Yellow to orange to brown/Liquid
• Density: 1.521 g/mL at 25 °C
• Vapor Pressure: 18mmHg at 25°C
• Refractive Index: 1.307
• CAS DataBase Reference: BORON TRIS(TRIFLUOROACETATE)(CAS DataBase Reference)
• NIST Chemistry Reference: BORON TRIS(TRIFLUOROACETATE)(350-70-9)
• EPA Substance Registry System: BORON TRIS(TRIFLUOROACETATE)(350-70-9)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 1742 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 350-70-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 350-70-9 differently. You can refer to the following data:
1. Reactant for:Trifluoroacetylation of arenes
2. Boron tris(trifluoroacetate) is a useful building block in synthetic chemistry. It can also be employed as a catalyst for homoallyboration reactions.

InChI:InChI=1/C6BF9O6/c8-4(9,10)1(17)20-7(21-2(18)5(11,12)13)22-3(19)6(14,15)16

Upstream product

• 76-05-1 trifluoroacetic acid 
• 400-53-3 trimethylsilyl trifluoroacetate 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 11113-50-1 boric acid 
• 407-25-0 trifluoroacetic anhydride 
• 10294-33-4 boron tribromide 
• 873-51-8 phenylborondichloride 

Downstream Products

• 330-25-6 tetrakis-trifluoroacetoxy-diboroxane 
• 407-25-0 trifluoroacetic anhydride 
• 85054-14-4 C₃₂H₃₉F₃ 
• 2314-97-8 iodotrifluoromethane 
• 60669-28-5 Trifluoromethyliodine(III) bis-trifluoroacetate 
• 68591-06-0 2,2,2-trifluoro-1,1,1-tri(4-methoxyphenyl)ethane 
• 61204-09-9 1,1,1-tris-(p-tolyl)-2,2,2-trifluoroethane 
• 85054-16-6 1,1-Bis-(2,4-dimethoxy-phenyl)-2,2,2-trifluoro-ethanol 
• 85054-18-8 C₁₄H₁₁F₃O₃ 

Relevant articles and documents

Synthesis and photophysical properties of ditrifluoroacetoxyboron complexes with curcumin analogues

A new class of ditrifluoroacetoxyboron complexes were designed and synthesized by chelation reaction of curcumins with boron trifluoroacetate. Their photophysical behaviors were studied in different solvents, powder state and PMMA polymer films. The results indicated that these complexes revealed a green to yellow emission at 486–595 nm in solution or PMMA films and an orange to red emission at 598–710 nm in powder state. Especially, complex 2c displayed the strongest emission intensity, the highest quantum yield in solution and the longest fluorescence lifetime in powder state in these complexes. In addtion, the emission bathochromic shifts of these complexes as a function of the solvent polarity parameter ET(30) were investigated by Lippert–Mataga approximation. It was observed that these complexes exhibited the higher values of the dipole moment difference (Δμ) between the ground and excited states, which implied an intense intramolecular charge transfer characteristics and a noticeable emission solvatochromic effect.

Boron carboxylate catalysis of homoallylboration

Boron tris(trifluoroacetate) is identified as the first effective catalyst for the homoallyl- and homocrotylboration of aldehydes by cyclopropylcarbinylboronates. NMR spectroscopic studies and theoretical calculations of key intermediates and transition states both suggest that a ligand-exchange mechanism, akin to our previously reported PhBCl 2-promoted homoallylations, is operative. Our experimental and theoretical results also suggest that the catalytic activity of boron tris(trifluoroacetate) might originate from more facile catalytic turnover of the trifluoroacetate ligands (in agreement with DFT calculations) or from a lower propensity for formation of off-pathway reservoir intermediates (as observed by 1H NMR). This work shows that carboxylates are viable catalytic ligands for homoallyl- and homocrotylations of carbonyl compounds and opens the door to the development of catalytic asymmetric versions of this transformation.

Preparation of phenylalkyl ethers and phenyl esters from benzenediazonium tetrafluoroborate with alkoxytrimethylsilanes and trimethylsilyl esters

Sonication assisted reaction of benzenediazonium tetrafluoroborate with alkoxytrimethylsilanes and trimethylsilyl esters gives phenylalkyl ethers and phenyl esters, respectively, with trialkyl(aryl) borates as byproducts. The scope of the reaction, experimental conditions and proposed mechanism are discussed.