109-63-7

Basic information

• Product Name: Boron trifluoride etherate
• Synonyms: 1’-oxybis[ethane]]-trifluoro[(beta-4)-boro;bf3-ethercomplex;Borane, trifluoro-, compd. with 1,1'-oxybis(ethane) (1:1);borane,trifluoro-,cmpdwith1,1’-oxybis(ethane)(1:1);Borane,trifluoro-,compd.with1,1’-oxybis[ethane](1:1);Boron fluoride diethyl etherate;Boron fluoride etherate;Boron fluoride monoetherate
• CAS NO: 109-63-7
• Molecular Formula: C₄H₁₀BF₃O
• Molecular Weight: 141.93
• EINECS: 203-689-8
• Product Categories: Industrial/Fine Chemicals;Organometallics;Boron Trifluorides;Boron Trihalides;B (Classes of Boron Compounds);Biochemistry;Reagents for Oligosaccharide Synthesis;Fluoro series;Fine Chemical
• Mol File: 109-63-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: −58 °C(lit.)
• Boiling Point: 126-129 °C(lit.)
• Flash Point: 118 °F
• Appearance: brown/liquid
• Density: 1.15 g/mL(lit.)
• Vapor Density: 4.9 (vs air)
• Vapor Pressure: 4.2 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.344(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with ether and alcohol.
• Explosive Limit: 5.1-18.2%(V)
• Water Solubility: Reacts
• Sensitive: Moisture Sensitive
• Stability: Stable. Highly flammable. May form explosive peroxides in contact with air or oxygen. Reacts exothermically with water to form e
• Merck: 14,1350
• BRN: 3909607
• CAS DataBase Reference: Boron trifluoride etherate(CAS DataBase Reference)
• NIST Chemistry Reference: Boron trifluoride etherate(109-63-7)
• EPA Substance Registry System: Boron trifluoride etherate(109-63-7)

Safety Data

• Hazard Codes: T,C
• Statements: 10-14-20/22-35-48/23-34-14/15-23-22
• Safety Statements: 16-23-26-36/37/39-45-8-28A-43
• RIDADR: UN 2604 8/PG 1
• WGK Germany: 3
• F: 10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: I
• Hazardous Substances Data: 109-63-7(Hazardous Substances Data)

Usage

Chemical Description

Different sources of media describe the Chemical Description of 109-63-7 differently. You can refer to the following data:
1. Boron trifluoride etherate is a Lewis acid that is commonly used as a catalyst in organic synthesis.
2. Boron trifluoride etherate is a Lewis acid used as a catalyst in organic synthesis.
3. Boron trifluoride etherate is a Lewis acid catalyst used to obtain 1-(p_nitrophenyl)cyclopentane carboxaldehyde.

Chemical Properties

Different sources of media describe the Chemical Properties of 109-63-7 differently. You can refer to the following data:
1. Colorless to brown fuming liquid.
2. Boron trifluoride etherates: (compounded with methyl ether) is moisture-sensitive, corrosive, flammable liquid.

uses

Boron trifluoride diethyl etherate is used as a Lewis acid catalyst in Mukaiyama aldol addition, alkylation, acetylation, isomerization, dehydrations and condensation reactions. It is involved in the prepattion of polyethers in polymerization reactions. As a catalyst, it is used in the preparation of cyclopentyl- and cycloheptyl[b]indoles and other diborane. It is also used in sensitive neutron detectors in ionization chambers as well as monitoring radiation levels in earth?s atmosphere.

Preparation

Different sources of media describe the Preparation of 109-63-7 differently. You can refer to the following data:
1. Boron trifluoride gas, produced by heating the sulfuric acid, calcium fluoride (fluorite) and boric acid together, reacts with ether boron to produce the trifluoride etherate crude product, thus we can refine it to get the finished product. The consumption of raw material is as followed: boric acid (≥98%), 560kg/t; calcium fluoride(≥90%) 1150kg/t; fuming sulfuric acid (104.5%), 4100kg/t; ether(≥99%) 725kg/t.In absorption method shown in the chemical equations as followed, diethyl ether absorb boron trifluoride gas, produced by heating the sulfuric acid, calcium fluoride (fluorite) and boric acid together, to produce trifluoride etherate crude complex compound by vacuum distillation.3H2SO4+2H33BO3+3CaF2→2BF3+3CaSO4+6H2OBF3+(C2H5)2O→(C2H5)2O?BF3
2. Boron trifluoride etherate is prepared by the reaction of vapors of boron trifluoride with that of anhydrous diethyl ether:BF3 (g) + (C2H5)2O (g) → (C2H5)2O?BF3.

Toxicity

See boron trifluoride.

Physical properties

Fuming liquid; stable at ambient temperatures but hydrolyzed on exposure to moist air; density 1.125 g/mL; refractive index 1.348; solidifies at -60.4°C; boils at 125.7°C; flash point (open cup) 147°F (68.8°C); decomposes in water.

Uses

Catalyst in acetylation, alkylation, polymerization, dehydration, and condensation reactions.

Application

Catalyst in the synthesis of polyol chains. Reagent for the coupling of imines to allylstannanes and 4′-nitrobenzenesulfenanilide to alkenes and alkynes.Lewis acid reagent with broad applicationCatalyst used in the preparation of cyclopentyl- and cycloheptyl[b]indoles from aryl cyclopropyl ketones via [3+2] cycloaddition.

General Description

Boron trifluoride etherate is a fuming liquid. Boron trifluoride etherate may be corrosive to skin, eyes and mucous membranes. Boron trifluoride etherate may be toxic by inhalation. Upon exposure to water Boron trifluoride etherate may emit flammable and corrosive vapors. Boron trifluoride etherate is used as a catalyst in chemical reactions.

Air & Water Reactions

Highly flammable. Fuming liquid, immediately hydrolyzed by moisture in air to form hydrogen fluoride [Merck 11th ed. 1989].

Reactivity Profile

Boron trifluoride diethyl ether complex is a stable, highly flammable, colourless to brown fuming, corrosive liquid with a sharp pungent odour. It forms explosive peroxides in contact with air or oxygen. It reacts exothermically with water to form extremely flammable diethyl ether and toxic, corrosive boron trifluoride hydrates. The chemical is incompatible with bases, amines, and alkali metals. It immediately gets hydrolysed by moisture in air to form hydrogen fluoride. Boron trifluoride diethyl ether has applications in chemical laboratory as a catalyst in chemical reactions.

Hazard

The compound is highly toxic by inhalation. Skin contact causes burns.

Health Hazard

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Flammable

Potential Exposure

Used as a catalyst.

Shipping

Diethyl: UN2604 Boron trifluoride diethyl etherate, Hazard class: 8; Labels: 8—Corrosive material, 3—Flammable liquid. Dimethyl: UN2965 Boron trifluoride dimethyl etherate, Hazard class: 4.3; Labels: 4.3— Dangerous when wet, 8—Corrosive material, 3— Flammable liquid.

Incompatibilities

Reacts with air forming corrosive hydrogen fluoride vapors. Incompatible with oxidizers (may cause fire and explosion), water, steam or heat, forming corrosive and flammable vapors. Peroxide containing etherate reacts explosively with aluminum lithium hydride, magnesium tetrahydroaluminate. Mixtures with phenol react explosively with 1,3-butadiene. Presumed to form explosive peroxides.

InChI:InChI:1S/C4H10BF3O/c1-3-9(4-2)5(6,7)8/h3-4H2,1-2H3

Synthetic route

2,4,6-tris(trilfuoromethyl)phenyllithium (444-40-6) + boron trichloride (10294-34-5) → BF2Cl*Et2O (99919-68-3) + BFCl2*Et2O (99919-69-4) + boron trifluoride diethyl etherate (109-63-7) + 2,4,6-(CF3)3C6H2BCl2 (681812-01-1) + bis-(2,4,6-tris-trifluoromethyl-phenyl) fluoroborane (681812-02-2)

Conditions

Yield

In diethyl ether under an inert atm.; to a soln. of Li-contg. compd. in hexanes and Et2O was added dropwise an excess of B-contg. compd. (1 M in heptane) at -78°C ; the react. mixt. was allowed to warm to room temp. for 6 h; the soln. was filtered and the solvents were removed under vac.; a mixt.of yellow oil and white solid; the mixt. was vac. distd. at 60°C /0.05 Torr; the residue was sublimed at 95°C under vac.;

A n/a B n/a C n/a D 5% E 24%

boron trifluoride diethyl etherate (109-63-7) + 3-acetoxy-4-methoxyphenol (99179-72-3) → 1-(2,4-dihydroxy-5-methoxyphenyl)ethan-1-one (7298-21-7)

Conditions	Yield
at 70℃; for 2h;	100%

boron trifluoride diethyl etherate (109-63-7) + 1-[bis(diisopropylamino)boryl]imidazole (675837-54-4) → 1-[bis(diisopropylamino)boryl]imidazole(N(3)-B)trifuoroborane (675837-55-5)

Conditions	Yield
In tetrahydrofuran under Ar; BF3*OEt2 added to soln. of N-compd. in THF at -78°C, mixt. allowed to warm to room temp., stirred for 7 h; evapn. of solvent;	100%

boron trifluoride diethyl etherate (109-63-7) + acetylacetone (123-54-6) → (acetylacetonato)borondifluoride (15390-25-7)

Conditions	Yield
With potassium carbonate In dichloromethane at 20℃; for 0.5h;	100%
In dichloromethane for 12h; Inert atmosphere;	96%
With diphenyl acetylene In dichloromethane at 20℃; for 12h;	83%

C2H5OCOC4N(CH3)2CHC4H2N(OCH3)C4H4N*HCl (946613-44-1) + boron trifluoride diethyl etherate (109-63-7) → [(C2H5OCOC4N(CH3)2CHC4HN(OCH3)C4H3NH)BF2] (1318245-52-1)

Conditions	Yield
With (C2H5)3N In dichloromethane (C2H5)3N added to a soln. of ligand salt under N2, stirred for 10 min, Bcomplex added, stirred at room temp. for 2 h; poured into an aq. soln. of citric acid, extd. (ether), the org. layer washed with aq. citric acid, dried (Na2SO4), concd. (vac.), filtered (silica, CH2Cl2), concd. (vac.);	100%

boron trifluoride diethyl etherate (109-63-7) + (1E,4Z,6E)-5-hydroxy-4-(3-methoxyphenyl)-1,7-bis(4-methoxyphenyl)hepta-1,4,6-trien-3-one (1430883-93-4) → (1E,4Z,6E)-5-(difluoroboryloxy)-4-(3-methoxyphenyl)-1,7-bis(4-methoxyphenyl)hepta-1,4,6-trien-3-one

Conditions	Yield
In dichloromethane Reflux;	100%

boron trifluoride diethyl etherate (109-63-7) + (1E,4Z,6E)-5-hydroxy-1,4,7-tris(4-methoxyphenyl)hepta-1,4,6-trien-3-one (1430883-95-6) → (1E,4Z,6E)-5-(difluoroboryloxy)-1,4,7-tris(4-methoxyphenyl)hepta-1,4,6-trien-3-one

Conditions	Yield
In dichloromethane Reflux;	100%

boron trifluoride diethyl etherate (109-63-7) + methyl 4-((1E,3Z,6E)-3-hydroxy-1,7-bis(4-methoxyphenyl)-5-oxohepta-1,3,6-trien-4-yl)benzoate (1430883-98-9) → (1E,4Z,6E)-5-(difluoroboryloxy)-4-(4-methoxyphenyl)-1,7-bis(4-methoxyphenyl)hepta-1,4,6-trien-3-one

Conditions	Yield
In dichloromethane Reflux;	100%

boron trifluoride diethyl etherate (109-63-7) + (1E,4Z,6E)-5-hydroxy-1,7-bis(4-methoxyphenyl)-4-phenylhepta-1,4,6-trien-3-one (1430884-00-6) → (1E,4Z,6E)-5-(difluoroboryloxy)-1,7-bis(4-methoxyphenyl)-4-phenylhepta-1,4,6-trien-3-one

Conditions	Yield
In dichloromethane Reflux;	100%

boron trifluoride diethyl etherate (109-63-7) + (1E,4Z,6E)-5-hydroxy-1,7-bis(4-methoxynaphthalen-1-yl)-4-phenylhepta-1,4,6-trien-3-one (1430884-04-0) → (1E,4Z,6E)-5-(difluoroboryloxy)-1,7-bis(4-methoxynaphthalen-1-yl)-4-phenylhepta-1,4,6-trien-3-one

Conditions	Yield
In dichloromethane Reflux;	100%

boron trifluoride diethyl etherate (109-63-7) + (1E,4Z,6E)-5-hydroxy-1,7-bis(6-methoxynaphthalen-2-yl)-4-phenylhepta-1,4,6-trien-3-one (1430884-06-2) → (1E,4Z,6E)-5-(difluoroboryloxy)-1,7-bis(6-methoxynaphthalen-2-yl)-4-phenylhepta-1,4,6-trien-3-one

Conditions	Yield
In dichloromethane Reflux;	100%

boron trifluoride diethyl etherate (109-63-7) + (1E,4Z,6E)-5-hydroxy-1,7-bis(9-methyl-9H-carbazol-3-yl)-4-phenylhepta-1,4,6-trien-3-one (1430884-08-4) → (1E,4Z,6E)-5-(difluoroboryloxy)-1,7-bis(9-methyl-9H-carbazol-3-yl)-4-phenylhepta-1,4,6-trien-3-one

Conditions	Yield
In dichloromethane Reflux;	100%

18-crown-6 ether (17455-13-9) + iodosylbenzene (536-80-1) + boron trifluoride diethyl etherate (109-63-7) → C6H6BF4IO*C12H24O6

Conditions	Yield
In dichloromethane at -78 - 0℃; for 4h; Inert atmosphere;	100%

boron trifluoride diethyl etherate (109-63-7) + 2,2'-[(1E,1'E)-(ethane-1,2-diylbis(azanylylidene)bis(methanylylidene))]bis(4-benzhydrylphenol) → 3,3'-(ethane-1,2-diyl)bis(2,2-difluoro-6-benzhydryl-2H-benzo[e][1,3,2]oxazaborinin-3-ium-2-uide)

Conditions	Yield
Stage #1: 2,2'-[(1E,1'E)-(ethane-1,2-diylbis(azanylylidene)bis(methanylylidene))]bis(4-benzhydrylphenol) With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane for 0.166667h; Heating; Stage #2: boron trifluoride diethyl etherate In 1,2-dichloro-ethane for 0.5h; Inert atmosphere; Heating;	100%

boron trifluoride diethyl etherate (109-63-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → dimethylformamide borontrifluoride

Conditions	Yield
In tetrahydrofuran at 0℃;	100%

boron trifluoride diethyl etherate (109-63-7) + Acetanilid (103-84-4) → C8H9BF3NO

Conditions	Yield
In toluene Reflux;	100%

2,5-diacetoxytoluene (717-27-1) + boron trifluoride diethyl etherate (109-63-7) → 1-(2,5-dihydroxy-4-methylphenyl)ethanone (54698-17-8)

Conditions	Yield
at 130℃; for 4h; Inert atmosphere;	100%

boron trifluoride diethyl etherate (109-63-7) + C72H98Br2N6O2 → C72H96B2Br2F4N6O2

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	100%

boron trifluoride diethyl etherate (109-63-7) + C72H100N6O2 → C72H98B2F4N6O2

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	100%

boron trifluoride diethyl etherate (109-63-7) + 3,3’-dimethoxy-2,2’-diphenyl-6-(pentafluorophenyl)dipyrrin → N,N’-difluoroboryl-3,3’-dimethoxy-2,2’-diphenyl-6-(pentafluorophenyl)dipyrrin

Conditions	Yield
Stage #1: 3,3’-dimethoxy-2,2’-diphenyl-6-(pentafluorophenyl)dipyrrin With triethylamine In toluene at 70℃; for 0.5h; Inert atmosphere; Stage #2: boron trifluoride diethyl etherate In toluene at 110℃; for 4h; Inert atmosphere;	100%

boron trifluoride diethyl etherate (109-63-7) + C119H128N10Ni2 → C119H127BF2N10Ni2

Conditions	Yield
With triethylamine In toluene	100%

diethyl ether (60-29-7) + boron trifluoride diethyl etherate (109-63-7) + 1-(4-bromo-2-azidophenyl)-4-phenyl-1H-1,2,3-triazole → 1-(2-azido-4-bromophenyl)-3-ethyl-4-phenyl-1H-1,2,3-triazol-3-ium tetrafluoroborate

Conditions	Yield
Stage #1: diethyl ether; boron trifluoride diethyl etherate With epichlorohydrin In diethyl ether for 1h; Inert atmosphere; Reflux; Stage #2: 1-(4-bromo-2-azidophenyl)-4-phenyl-1H-1,2,3-triazole In dichloromethane	100%

boron trifluoride diethyl etherate (109-63-7) + (1s,3s)-4-((1E,4Z,6E)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trien-1-yl)-2-methoxyphenyladamantane-1-carboxylate → C32H33BF2O7

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere;	100%

boron trifluoride diethyl etherate (109-63-7) + C17H18N2O6 → C17H17BF2N2O6

Conditions	Yield
In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%

boron trifluoride diethyl etherate (109-63-7) + N-hydroxy-4-methoxy-N-(2-(4-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethyl)benzamide → C21H24BF2NO4

Conditions	Yield
In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%

boron trifluoride diethyl etherate (109-63-7) + N-(3,5-dimethoxyphenethyl)-N-hydroxy-4-methoxybenzamide → C18H20BF2NO5

Conditions	Yield
In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%

nitrosyl(5,10,15,20-tetraphenylporphyrinato)(pyridine)cobalt(III) (75778-52-8) + boron trifluoride diethyl etherate (109-63-7) → pyCo(tetraphenylporphyrin)NO*BF3 + benzaldehyde (100-52-7)

Conditions	Yield
With benzyl alcohol In 1,2-dichloro-ethane byproducts: BF3-pyridine complex, H2O; under Ar addn. of BF3*Et2O to mixt. of alcohol and complex in (CH2)2Cl2, further addn. of BF3*Et2O, heating in 60°C oil bath for 45 min,addn. 1 drop of pyridine in hexane, removing BF3-pyridine complex pptd.; solvent removing in vac., addn. of petroleum ether to resulting oil, filtration, drying under Ar;	A n/a B 99%

cyclopentadienyl-dicarbonyl-triethoxysilylmethyl-iron (375391-20-1) + boron trifluoride diethyl etherate (109-63-7) → cyclopentadienyl-dicarbonyl-trifluorosilylmethyl-iron (375391-21-2)

Conditions	Yield
In toluene under N2, excess of BF3(OEt2) was added, stirring for 30 min; volatiles were removed;	99%

boron trifluoride diethyl etherate (109-63-7) + ((CH3)3C)2PCN(CH(CH3)2)2 (443147-01-1) → ((CH3)3C)2PC(BF3)N(CH(CH3)2)2

Conditions	Yield
In tetrahydrofuran treatment THF soln. carbene with 1 equiv. BF3*OEt2;	99%

2,4-dimethyl-1H-pyrrole (625-82-1) + 2-pyrrole aldehyde (1003-29-8) + boron trifluoride diethyl etherate (109-63-7) → 5,5-difluoro-1,3-dimethyl-5H-4λ4,5λ,4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine (154793-49-4)

Conditions	Yield
Stage #1: 2,4-dimethyl-1H-pyrrole; 2-pyrrole aldehyde With trichlorophosphate In dichloromethane at -5 - 20℃; for 6h; Inert atmosphere; Stage #2: boron trifluoride diethyl etherate With N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;	99%
Stage #1: 2,4-dimethyl-1H-pyrrole; 2-pyrrole aldehyde With trichlorophosphate In dichloromethane at 0 - 20℃; for 2h; Stage #2: boron trifluoride diethyl etherate With triethylamine In dichloromethane at 20℃; for 1h;	36.1%
With N-ethyl-N,N-diisopropylamine; trichlorophosphate In dichloromethane (N2) to soln. pyrrole 2-carboxyaldehyde in CH2Cl2 at -5°C, 2,4-dimethylpyrrole was added, stirred for 3 min, POCl3 was dropwise added, stirred at -5°C for 3 h and at room temp. 3 h, i-Pr2NEt and BF3*Et2O were added, stirred for 3 h; react. mixt. was washed with H2O, dried over Na2SO4, evapd., residue waschromd. on silica (hexane/EtOAc, 5:1);	32.8%

acetylferrocene (1271-55-2) + boron trifluoride diethyl etherate (109-63-7) → [Fe(C5H5)(C5H4C(OBF3)CH3)] (1162093-13-1)

Conditions	Yield
In diethyl ether under dry N2; mixing of soln. at equimolar ratio; solvent was evapd., crystals were grown by vapor diffusion of pentane into chloroform soln. at -30°C over 2 days; NMR, IR, XRD;	99%

Upstream product

• 7637-07-2 boron trifluoride 
• 60-29-7 diethyl ether 
• 2261-02-1 acetylium tetrafluoroborate 
• 67969-82-8 tetrafluoroboric acid diethyl ether 
• 35963-96-3 Trifluorsulfonium-tetrafluoroborat 
• 122-51-0 orthoformic acid triethyl ester 
• 368-39-8 triethyloxonium fluoroborate 
• 64-17-5 ethanol 
• 444-40-6 2,4,6-tris(trilfuoromethyl)phenyllithium 
• 10294-34-5 boron trichloride 

Downstream Products

• 103185-78-0 8-phenyl-8-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)octanoic acid 
• 19287-45-7 diborane 
• 90536-74-6 Ethyl 2,4,6-trihydroxybenzoate 
• 869535-58-0 1-(2,3,5,6-tetramethylbenzyl)cyclopropylamine 
• 195385-82-1 α-naphthyl 2,3,5-tri-O-benzoyl-β-D-ribofuranoside 
• 195385-86-5 1-Tetralone-5-yl 2,3,5-tri-O-benzoyl-β-D-Ribofuranoside 
• 195385-83-2 3-Trifluoroacetamidophenyl 2,3,5-tri-O-benzoyl β-D-ribofuranoside 
• 163439-82-5 (3R,4R)-1-benzyl-3,4-pyrrolidinediol 
• 10201-71-5 3-methoxypyridin-2-amine 
• 121099-56-7 7-(4-fluorophenyl)-7-(2-hydroxy-3,5,6-trimethylphenyl)heptanoic acid 
• 779329-95-2 4-methyl-1-[[4-(trifluoromethyl)phenoxy]methyl]-2,6,7-trioxabicyclo[2.2.2]octane 

Relevant articles and documents

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