462-34-0

Basic information

• Product Name: Boron trifluoride tetrahydrofuran complex
• Synonyms: BORON TRIFLUORIDE TETRAHYDROFURAN COMPLEX;trifluoro(tetrahydrofuran)boron;BORON TRIFLUORIDE TETRAHYDROFURANE;Boron, trifluoro(tetrahydrofuran)-, (T-4)-;Boron trifluoride tetrahydrofuran complex 95%;Borontrifluoridetetrahydrofurancomplex95%;Trifluor(tetrahydrofuran)bor;Boron trifluoride tetrahydrofuran complex,50%
• CAS NO: 462-34-0
• Molecular Formula: C₄H₈BF₃O
• Molecular Weight: 139.91
• EINECS: 207-325-9
• Product Categories: Furan&Benzofuran;Boron;BoronSynthetic Reagents;Catalysis and Inorganic Chemistry;Chemical Synthesis;Lewis Acids
• Mol File: 462-34-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: −123 °C(lit.)
• Boiling Point: 180 °C(lit.)
• Flash Point: 198 °F
• Appearance: Colorless to light yellow liquid
• Density: 1.268 g/mL at 25 °C(lit.)
• Vapor Pressure: 11Pa
• Storage Temp.: Store below +30°C.
• Solubility: Miscible with dimethyl formamide.
• Explosive Limit: 2.3-17.7%(V)
• Water Solubility: hydrolysis
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: Boron trifluoride tetrahydrofuran complex(CAS DataBase Reference)
• NIST Chemistry Reference: Boron trifluoride tetrahydrofuran complex(462-34-0)
• EPA Substance Registry System: Boron trifluoride tetrahydrofuran complex(462-34-0)

Safety Data

• Hazard Codes: C,T
• Statements: 34-48/23-35-20/22
• Safety Statements: 26-27-36/37/39-45-28A-23-28
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 462-34-0(Hazardous Substances Data)

Usage

Description

Boron trifluoride tetrahydrofuran complex is a chemical compound consisting of boron trifluoride (BF3) and tetrahydrofuran (THF) molecules. It is a versatile reagent used in various chemical reactions and synthesis processes.

Uses

Used in Organic Synthesis:
Boron trifluoride tetrahydrofuran complex is used as a reagent for the deoxofluorination of alcohols and carbonyls, which is a key step in the synthesis of various organic compounds.
Used in Polymer Synthesis:
Boron trifluoride tetrahydrofuran complex is used as a reagent in the synthesis of methacrylate-PEG-methacrylate-boron trifluoride self-doped gel polymer electrolytes, which are important materials for energy storage and conversion applications.
Used in Hydroboration-Oxidation Reactions:
Boron trifluoride tetrahydrofuran complex is used as a reagent in the hydroboration-oxidation of divinylferrocene, a reaction that is crucial for the synthesis of organometallic compounds.
Used in the Synthesis of Biologically Active Molecules:
Boron trifluoride tetrahydrofuran complex is used as a reagent in the synthesis of various biologically active molecules, including NK1 receptor antagonists, complex polyketide natural products, and selective serotonin reuptake inhibitors. These molecules have potential applications in pharmaceuticals and drug development.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C4H8O.B.3FH/c1-2-4-5-3-1;;;;/h1-4H2;;3*1H/q;+3;;;/p-3

Synthetic route

boron trifluoride-tetrahydrofuran complex (462-34-0) → 1-[(76)Br]bromo-2-phenylethyne

Conditions	Yield
With peracetic acid; ammonium 76Br-bromide; ammonia In methanol; water at 20℃; for 0.166667h;	80%

boron trifluoride-tetrahydrofuran complex (462-34-0) + Pentaerythritol (115-77-5) → C5H8B2F2O4

Conditions	Yield
Stage #1: boron trifluoride-tetrahydrofuran complex; Pentaerythritol In acetonitrile at 20℃; for 1h; Stage #2: With chloro-trimethyl-silane In acetonitrile at 80℃; for 10h; Reagent/catalyst; Temperature;	96%

N-trimethylsilylpyrrolidine (15097-49-1) + boron trifluoride-tetrahydrofuran complex (462-34-0) + sulfur tetrafluoride (7783-60-0) → pyrrolidinodifluorosulfiniumtetrafluoroborate

Conditions	Yield
Stage #1: N-trimethylsilylpyrrolidine; sulfur tetrafluoride In dichloromethane at -78 - 20℃; Inert atmosphere; Stage #2: boron trifluoride-tetrahydrofuran complex In dichloromethane at 20 - 25℃; for 2h; Inert atmosphere;	85%
Stage #1: N-trimethylsilylpyrrolidine; sulfur tetrafluoride In dichloromethane at -65 - 20℃; Inert atmosphere; Stage #2: boron trifluoride-tetrahydrofuran complex In dichloromethane at 25℃; for 2h; Inert atmosphere;	85%

boron trifluoride-tetrahydrofuran complex (462-34-0) + sulfur tetrafluoride (7783-60-0) + N-(trimethylsilyl)phenyl(methyl)amine (17890-34-5) → N-methyl-N-phenylaminodifluorosulfiniumtetrafluoroborate

Conditions	Yield
Stage #1: sulfur tetrafluoride; N-(trimethylsilyl)phenyl(methyl)amine In dichloromethane at -78 - 20℃; Inert atmosphere; Stage #2: boron trifluoride-tetrahydrofuran complex In dichloromethane at 20 - 25℃; for 2.16667h; Inert atmosphere;	93%
Stage #1: sulfur tetrafluoride; N-(trimethylsilyl)phenyl(methyl)amine In dichloromethane at -70 - 20℃; Inert atmosphere; Stage #2: boron trifluoride-tetrahydrofuran complex In dichloromethane at 25℃; for 2.16667h; Inert atmosphere;	93%

boron trifluoride-tetrahydrofuran complex (462-34-0) + sulfur tetrafluoride (7783-60-0) + N-trimethylsilyl-N-methyl-2-aminopyridine (92982-38-2) → N-methyl-N-(2-pyridyl)aminodifluorosulfinium tetrafluoroborate

Conditions	Yield
Stage #1: sulfur tetrafluoride; N-trimethylsilyl-N-methyl-2-aminopyridine In dichloromethane at -78 - 20℃; Inert atmosphere; Stage #2: boron trifluoride-tetrahydrofuran complex In dichloromethane at 20 - 21℃; for 1.58333h; Inert atmosphere;	78%
Stage #1: sulfur tetrafluoride; N-trimethylsilyl-N-methyl-2-aminopyridine In dichloromethane at -70 - 20℃; Inert atmosphere; Stage #2: boron trifluoride-tetrahydrofuran complex In dichloromethane at 21℃; for 1.58333h; Inert atmosphere;	78%

boron trifluoride-tetrahydrofuran complex (462-34-0) + diethylamino-sulfur trifluoride (38078-09-0) → ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate

Conditions	Yield
In diethyl ether at 20 - 30℃; for 1.25h; Inert atmosphere;	85%

4-(trimethylsilyl)morpholine (13368-42-8) + boron trifluoride-tetrahydrofuran complex (462-34-0) + sulfur tetrafluoride (7783-60-0) → difluoro-4-morpholinylsulfonium tetrafluoroborate

Conditions	Yield
Stage #1: 4-(trimethylsilyl)morpholine; sulfur tetrafluoride In dichloromethane at -78 - 20℃; Inert atmosphere; Stage #2: boron trifluoride-tetrahydrofuran complex In dichloromethane at 25℃; for 4h; Inert atmosphere;	92%

boron trifluoride-tetrahydrofuran complex (462-34-0) + sulfur tetrafluoride (7783-60-0) + N,N-diethyl-1,1,1-trimethylsilanamine (996-50-9) → ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate

Conditions	Yield
Stage #1: sulfur tetrafluoride; N,N-diethyl-1,1,1-trimethylsilanamine In dichloromethane at -78 - 20℃; Inert atmosphere; Stage #2: boron trifluoride-tetrahydrofuran complex In dichloromethane at 15 - 25℃; for 1.5h; Inert atmosphere;	89%

boron trifluoride-tetrahydrofuran complex (462-34-0) + sulfur tetrafluoride (7783-60-0) + N-Methyl-N-(trimethylsilyl)benzylamin (14884-70-9) → N-benzyl-N-methylaminodifluorosulfinium tetrafluoroborate

Conditions	Yield
Stage #1: sulfur tetrafluoride; N-Methyl-N-(trimethylsilyl)benzylamin In dichloromethane at -78 - 20℃; Inert atmosphere; Stage #2: boron trifluoride-tetrahydrofuran complex In dichloromethane at 20 - 25℃; for 1.16667h; Inert atmosphere;	73%

boron trifluoride-tetrahydrofuran complex (462-34-0) + lithium oxalate (553-91-3) → lithium oxalate-boron trifluoride

Conditions	Yield
at 23℃; for 24h;	94.7%
at 23℃; for 24h;	94.7%

1-hexene (592-41-6) + boron trifluoride-tetrahydrofuran complex (462-34-0) → 2-butyl-1-fluoroborirane + 2-hexene (592-43-8)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; magnesium In tetrahydrofuran at 0 - 20℃; for 14h; Inert atmosphere;

boron trifluoride-tetrahydrofuran complex (462-34-0) + non-1-ene (124-11-8) → 1-fluoro-2-heptylborirane + cis,trans-2-nonylene (2216-38-8)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; magnesium In tetrahydrofuran at 0 - 20℃; for 14h; Inert atmosphere;

boron trifluoride-tetrahydrofuran complex (462-34-0) + 1-Decene (872-05-9) → 2-decene (20063-97-2, 20348-51-0, 6816-17-7) + 1-fluoro-2-octylborirane

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; magnesium In tetrahydrofuran at 0 - 20℃; for 14h; Inert atmosphere;

boron trifluoride-tetrahydrofuran complex (462-34-0) + 1-dodecene (112-41-4) → dodec-2-ene (1652-96-6) + 2-decyl-1-fluoroborirane

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; magnesium In tetrahydrofuran at 0 - 20℃; for 14h; Inert atmosphere;

boron trifluoride-tetrahydrofuran complex (462-34-0) + 1-tetradecene (1120-36-1) → tetradec-2-ene (1652-97-7) + 2-dodecyl-1-fluoroborirane

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; magnesium In tetrahydrofuran at 0 - 20℃; for 14h; Inert atmosphere;

boron trifluoride-tetrahydrofuran complex (462-34-0) + oct-1-ene (111-66-0) → 2-octene (111-67-1) + 1-fluoro-2-hexylborirane

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; magnesium In tetrahydrofuran at 0 - 20℃; for 14h; Inert atmosphere;

boron trifluoride-tetrahydrofuran complex (462-34-0) + 4-Aminobenzonitrile (873-74-5) → 4-cyanophenyldiazonium tetrafluoroborate (2252-32-6)

Conditions	Yield
With tert.-butylnitrite In isopropyl alcohol at 0 - 20℃; for 1.25h;	91%

boron trifluoride-tetrahydrofuran complex (462-34-0) + 7-Amino-2-methyl-chromone (30779-70-5) → 2-methyl-4-oxo-4H-chromene-7-diazonium tetrafluoroborate

Conditions	Yield
With tert.-butylnitrite In ethanol at 0 - 20℃; for 1.25h;	88%

boron trifluoride-tetrahydrofuran complex (462-34-0) + anthranilic acid nitrile (1885-29-6) → 2-cyano-benzenediazonium tetrafluoroborate (55165-45-2)

Conditions	Yield
With tert.-butylnitrite In ethanol at 0 - 20℃; for 2h;	89%

boron trifluoride-tetrahydrofuran complex (462-34-0) + 2,3,4,5,6-pentafluorophenylmagnesium bromide (879-05-0) → tris(pentafluorophenyl)borate (1109-15-5)

Conditions	Yield
In dibutyl ether; methyl cyclohexane at 20 - 30℃; for 2.5h; Solvent; Inert atmosphere;

boron trifluoride-tetrahydrofuran complex (462-34-0) + 4-methoxycarbonyl aniline (619-45-4) → 4-(methoxycarbonyl)benzenediazonium tetrafluoroborate

Conditions	Yield
With tert.-butylnitrite In tetrahydrofuran at 0 - 20℃; for 1.25h;	77%

boron trifluoride-tetrahydrofuran complex (462-34-0) + 3-nitro-aniline (99-09-2) → 3-nitrophenyldiazonium tetrafluoroborate (586-36-7)

Conditions	Yield
With tert.-butylnitrite In tetrahydrofuran at 0 - 20℃; for 1.25h;	73%

boron trifluoride-tetrahydrofuran complex (462-34-0) + 6-(trifluoromethyl)pyridin-3-amine (106877-33-2) → 2-trifluoromethyl-pyridine-5-diazonium tetrafluoroborate

Conditions	Yield
With tert.-butylnitrite In ethanol at 0 - 20℃; for 1.25h;	70%

boron trifluoride-tetrahydrofuran complex (462-34-0) → (C4H7)O(BF3)(1-)

Conditions	Yield
With F(1-) In gaseous matrix byproducts: HF; He buffer gas (0.4 Torr), room temp.;

boron trifluoride-tetrahydrofuran complex (462-34-0) + Mes2P-C{=C(H)-Ph}-AltBu2 (1308317-96-5, 1308318-08-2) → C34H46AlBF3P

Conditions	Yield
In toluene at 20℃; for 15h; Inert atmosphere; Schlenk technique;	95%

boron trifluoride-tetrahydrofuran complex (462-34-0) + 4-methoxy-aniline (104-94-9) + isopentyl nitrite (110-46-3) → 4-methoxybenzenediazonium tetrafluoroborate (459-64-3)

Conditions	Yield
Stage #1: boron trifluoride-tetrahydrofuran complex; 4-methoxy-aniline In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: isopentyl nitrite In tetrahydrofuran at 0℃; for 0.25h;	92%

boron trifluoride-tetrahydrofuran complex (462-34-0) + 1-Decene (872-05-9) → 1-fluoro-2-octylborirane

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; magnesium In tetrahydrofuran Schlenk technique;
With bis(cyclopentadienyl)titanium dichloride; magnesium In tetrahydrofuran at 20℃;

Upstream product

• 109-99-9 tetrahydrofuran 
• 7637-07-2 boron trifluoride 

Downstream Products

• 110-51-0 borane pyridine 
• 1109-15-5 tris(pentafluorophenyl)borate 
• 111-67-1 2-octene 
• 20063-97-2 2-decene 
• 592-43-8 2-hexene 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 55165-45-2 2-cyano-benzenediazonium tetrafluoroborate 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 586-36-7 3-nitrophenyldiazonium tetrafluoroborate 
• 41288-96-4 6-chloropyridine-3-ol 
• 1722-26-5 triethylamine-borane 

Relevant articles and documents

HIGH SPECIFIC ACTIVITY PREPARATION OF F-18 TETRAFLUOROBORATE

Embodiments of the invention provide methods of synthesizing 18F-tetrafluoroborate (18F-TFB) via direct radiofluorination on boron trifluoride (BF3) to enhance both labeling yield and specific activity. Uses of 18F-TFB are also contemplated.