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70863

Sigma-Aldrich

1-Butyl-2,3-dimethylimidazolium tetrafluoroborate

≥97.0%

Synonym(s):

[BDMIM][BF4]

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About This Item

Empirical Formula (Hill Notation):
C9H17BF4N2
CAS Number:
402846-78-0
Molecular Weight:
240.05
MDL number:
MFCD03427618
UNSPSC Code:
12352100
PubChem Substance ID:
57652264
NACRES:
NA.22

Assay

≥97.0%

form

liquid

impurities

≤1% water

mp

37 °C
37 °C

density

1.198 g/mL at 20 °C (lit.)

SMILES string

F[B-](F)(F)F.CCCCn1cc[n+](C)c1C

InChI

1S/C9H17N2.BF4/c1-4-5-6-11-8-7-10(3)9(11)2;2-1(3,4)5/h7-8H,4-6H2,1-3H3;/q+1;-1

InChI key

VCAIYEJBOWHUGP-UHFFFAOYSA-N

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General description

1-Butyl-2,3-dimethylimidazolium tetrafluoroborate is a task-specific ionic liquid.

Application

[bdmim]BF4 can be used as a solvent when lipase needs to be recycled during lipase-catalyzed transesterification with vinyl acetate as acyl donor. The [bdmim]BF4/toluene biphasic solvent forms an efficient system for the Negishi cross-coupling reaction between aryl zinc halides and aryl iodides.

Other Notes

Ionic liquid, suitable for use in strongly basic conditions, for aldol condensations

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Palladium catalyzed cross-couplings of organozincs in ionic liquids.
Sirieix J, et al.
Synlett, 2000(11), 1613-1615 (2000)
1-Butyl-2, 3-dimethylimidazolium tetrafluoroborate: the most desirable ionic liquid solvent for recycling use of enzyme in lipase-catalyzed transesterification using vinyl acetate as acyl donor.
Itoh T, et al.
Journal of Molecular Catalysis. B, Enzymatic, 26(1), 41-45 (2003)
The local structure of ionic liquids: cation?cation NOE interactions and internuclear distances in neat [BMIM][BF4] and [BDMIM][BF4]
Mele, Andrea, et al.
Angewandte Chemie (International Edition in English), 45.7, 1123-1126 (2006)
Stetter reaction in room temperature ionic liquids and application to the synthesis of haloperidol
Anjaiah, Siddam, Srivari Chandrasekhar, and Rene Gree
Advanced Synthesis & Catalysis, 346.11, 1329-1334 (2004)
Hydrolase-catalyzed Kinetic Resolution of 5-[4-(1-Hydroxyethyl) phenyl]-10, 15, 20-tris (pentafluorophenyl) porphyrin in Ionic Liquids
Ema, Tadashi, Tokuhiro Doi, and Takashi Sakai
Chemistry Letters (Jpn), 37.1, 90-91 (2007)
View All Related Papers

Articles

Task-Specific Ionic Liquids

Functionalized imidazolium cations with thioether, urea, or thiourea derivatized side chains act as metal-ligating moieties, whereas the PF6– anions provide the desired water immiscibility.

Task-Specific Ionic Liquids

Functionalized imidazolium cations with thioether, urea, or thiourea derivatized side chains act as metal-ligating moieties, whereas the PF6– anions provide the desired water immiscibility.

Task-Specific Ionic Liquids

Functionalized imidazolium cations with thioether, urea, or thiourea derivatized side chains act as metal-ligating moieties, whereas the PF6– anions provide the desired water immiscibility.

Task-Specific Ionic Liquids

Functionalized imidazolium cations with thioether, urea, or thiourea derivatized side chains act as metal-ligating moieties, whereas the PF6– anions provide the desired water immiscibility.

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