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913383

Sigma-Aldrich

1,3-Dimethylimidazoyl-2-ylidene borane

≥95%

Synonym(s):

(1,3-Dimethyl-1H-imidazol-3-ium-2-yl)trihydroborate, NHC-borane

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About This Item

Empirical Formula (Hill Notation):
C5H11BN2
CAS Number:
1211417-77-4
Molecular Weight:
109.97
MDL number:
MFCD32857291

Assay

≥95%

form

crystals

availability

available only in USA

mp

138-139 °C

storage temp.

2-8°C

SMILES string

[B-H]c1[n+](cc[n]1C)C

InChI key

WDITXRGBBBKEET-UHFFFAOYSA-N

Application

1,3-Dimethylimidazoyl-2-ylidene borane is stable NHC-borane developed in the Curran lab. It is a diverse reductant as well as a versatile hydroboration reagent.

Other Notes

Facile Synthesis of α-N-Heterocyclic Carbene-Boryl Ketones from N-Heterocyclic Carbene-Boranes and Alkenyl Triflates

Difluorination at Boron Leads to the First Electrophilic Ligated Boryl Radical (NHC-BF2.)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

913383-VAR:
913383-250MG:
913383-BULK:
913383-1G:

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Daniel Subervie et al.
Angewandte Chemie (International ed. in English), 57(32), 10251-10256 (2018-06-22)
1,3-Dimethylimidazol-2-ylidene difluoroborane (NHC-BF2 H) was prepared in a one-pot, two-step reaction from the parent ligated borane (NHC-BH3 ). The derived difluoroboryl radical (NHC-BF2. ) was generated by laser flash photolysis experiments and characterized by UV spectroscopy and rate-constant measurements. It is
Wen Dai et al.
Journal of the American Chemical Society, 141(31), 12355-12361 (2019-07-12)
Reactions of readily available alkenyl triflates with N-heterocyclic carbene (NHC)-boranes in the presence of diisopropyl ethyl amine provided about three dozen stable α-NHC-boryl ketones. Isolated yields were typically 40-56% for B-unsubstituted NHC-boranes (NHC-BH3), and somewhat lower for NHC-boranes with B-substituents

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