ethoxyethane; trifluoroborane

• ChemBase ID: 98870
• Molecular Formular: C4H10BF3O
• Molecular Mass: 141.9278096
• Monoisotopic Mass: 142.07768
• SMILES: FB(F)F.O(CC)CC
• Canonical SMILES: FB(F)F.CCOCC
• InChI: InChI=1S/C4H10O.BF3/c1-3-5-4-2;2-1(3)4/h3-4H2,1-2H3
• InChIKey: KZMGYPLQYOPHEL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethoxyethane; trifluoroborane
• IUPAC Traditional name: boron trifluoride; diethyl ether
• Synonyms: Boron trifluoride diethyl ether complex; Trifluoroborane diethyl ether complex; Boron trifluoride etherate; Boron fluoride-ether; Boron trifluoride diethyl etherate; min, packaged under Argon in resealable ChemSeal? bottles; 三氟化硼乙醚

Database IDs

• CAS Number: 109-63-7
• EC Number: 203-689-8
• MDL Number: MFCD00013194
• Beilstein Number: 3909607
• Merck Index: 141350
• PubChem SID: 162085214
• PubChem CID: 8000

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.83816534
• LogD (pH = 7.4): 0.83816534
• Log P: 0.83816534
• Molar Refractivity: 22.5097 cm^3
• Polarizability: 8.788117 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Liquid
• Melting Point: -60°C
• Boiling Point: 125-126°C
• Flash Point: 47°C(116°F)
• Density: 1.130
• Refractive Index: 1.3440

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Toxic (T)
• UN Number: UN2604
• Hazard Class: 8
• Packing Group: I
• Risk Statements: 10-22-23-35-48/23
• Safety Statements: 23-26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Hazard statements: H331-H302-H372-H314-H318-H226
• GHS Precautionary statements: P260-P280-P303+P361+P353-P305+P351+P338-P310; P260-P280-P305+P351+P338-P309-P310

Product Information

• Purity: 46.5% BF; 98+%

REFERENCES

• Lewis acid catalyst in a wide variety of applications, for example:
• Has also been used in conjunction with BMS in the reduction of amides: J. Org. Chem., 47, 3153 (1982).
• For use in the cleavage of ethers, see Tetra-n-butylammonium iodide, A15484.
• For analogous 1,4-addition to p-benzoquinones, see 2,3-Dimethoxy-5-methyl-1,4-benzoquinone, B24777.
• Mild dehydration of tertiary alcohols to alkenes: Tetrahedron Lett., 32, 6489 (1991). In the Diels-Alder reaction: J. Am. Chem. Soc., 99, 8116 (1977). In THP protection of alcohols: Synthesis, 81, (1972).
• Reaction with Sodium borohydride, 35788, can be used for the in situ generation of diborane. For use in the hydroboration of ɑ-pinene, see: Org. Synth. Coll., 6, 943 (1988).
• Catalyst for rearrangement of epoxides to carbonyl compounds, e.g. stilbene oxide to diphenylacetaldehyde and ring-contraction of isophorone oxide: Org. Synth. Coll., 4, 375 and 957 (1963), respectively.
• Reaction with ortho esters gives high yields of crystalline dialkoxycarbenium salts, useful as powerful and selective alkylating agents, (compare Triethyloxonium tetrafluoroborate, A14420 and Trimethyloxonium tetrafluoroborate, A15175): Synth. Commun., 19, 2307 (1989).
• Catalyst for the reaction of allyltin reagents with aldehydes and ketones. Addition to the carbonyl group proceeds with allylic rearrangement: Chem. Lett., 919, 977 (1979); Acc. Chem. Res., 20, 243 (1987):