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

Chemical Properties

Colorless to light yellow liqui

Uses

Reactant or reagent involved in:Deoxofluorination of alcohols and carbonylsSynthesis of methacrylate-PEG-methacrylate-boron trifluoride self-doped gel polymer electrolytesHydroboration-oxidation of divinylferroceneReagent involved in the synthesis of biologically active molecules such as: NK1 receptor antagonists Complex polyketide natural productsSelective serotonin reuptake inhibitors

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

• 1722-26-5 triethylamine-borane 
• 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 
• 110-51-0 borane pyridine 

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.