Boron trifluoride diethyl etherate

Boron trifluoride diethyl etherate Property

Melting point:

−58 °C(lit.)

Boiling point:

126-129 °C(lit.)

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.)

Flash point:

118 °F

storage temp. 

Store below +30°C.

solubility 

Miscible with ether and alcohol.

form 

liquid

color 

brown

Specific Gravity

1.126 (20/4℃)

explosive limit

5.1-18.2%(V)

Water Solubility 

Reacts

Sensitive 

Moisture Sensitive

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

Merck 

14,1350

BRN 

3909607

Exposure limits

ACGIH: TWA 0.1 ppm; Ceiling 0.7 ppm

Stability:

Stable. Highly flammable. May form explosive peroxides in contact with air or oxygen. Reacts exothermically with water to form extremely flammable diethyl ether and toxic, corrosive boron trifluoride hydrates. Also incompatible with bases, amines, alkali metals.

InChI

1S/C4H10O.BF3/c1-3-5-4-2;2-1(3)4/h3-4H2,1-2H3;

InChIKey

MZTVMRUDEFSYGQ-UHFFFAOYSA-N

SMILES

B(F)(F)F.O(CC)CC

CAS DataBase Reference

109-63-7(CAS DataBase Reference)

NIST Chemistry Reference

Boron trifluoride etherate(109-63-7)

EPA Substance Registry System

Boron, trifluoro[1,1'-oxybis[ethane]]-, (T-4)- (109-63-7)

Safety

Hazard Codes 

T,C

Risk 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

WGK Germany 

3

F 

10

Autoignition Temperature

185 °C DIN 51794

TSCA 

TSCA listed

HazardClass 

8

PackingGroup 

I

HS Code 

29319090

Storage Class

3 - Flammable liquids

Hazard Classifications

Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Dam. 1
Flam. Liq. 3
Skin Corr. 1B
STOT RE 1 Inhalation

Hazardous Substances Data

109-63-7(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H314Causes severe skin burns and eye damage

H372Causes damage to organs through prolonged or repeated exposure

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P314Get medical advice/attention if you feel unwell.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

Boron trifluoride diethyl etherate Chemical Properties,Usage,Production

Chemical Properties

Colorless to brown fuming 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

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+6H2O
BF3+(C2H5)2O→(C2H5)2O•BF3

Toxicity

See boron trifluoride.

Chemical Properties

Boron trifluoride etherates: (compounded with methyl ether) is moisture-sensitive, corrosive, flammable liquid.

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.

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 earths atmosphere.

Preparation

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)₂OBF₃.

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 application
Catalyst 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

reaction suitability

core: boron
reagent type: Lewis acid
reagent type: catalyst

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.