901267
Hexamethylborazine
≥95%
Synonym(s):
1,2,3,4,5,6-Hexamethyl-1,3,5,2,4,6-triazatriborinane
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About This Item
Empirical Formula (Hill Notation):
C6H18B3N3
CAS Number:
Molecular Weight:
164.66
MDL number:
UNSPSC Code:
12161600
NACRES:
NA.22
Quality Level
Assay
≥95%
form
powder or crystals
reaction suitability
core: boron
reagent type: catalyst
mp
99 °C
storage temp.
−20°C
SMILES string
B1(N(B(N(B(N1C)C)C)C)C)C
InChI
1S/C6H18B3N3/c1-7-10(4)8(2)12(6)9(3)11(7)5/h1-6H3
InChI key
LCHQMXUQYONIOI-UHFFFAOYSA-N
Application
Hexamethylborazine has been developed by the Szymczak lab for the delivery of alkyl and hydride nucleophiles in addition to being a key component in the synthesis of recyclable trifluoromethylation reagents.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Tyler J Carter et al.
Angewandte Chemie (International ed. in English), 51(52), 13168-13172 (2012-11-20)
Recharging spent BN fuel: {Cr(CO)(3)} mediates the reduction of borazines by hydride and methyl nucleophiles to generate anionic complexes of dearomatized hexamethylborazine. Subsequent quenching leads to the release of a substituted cyclotriborazane, successfully demonstrating the stepwise reduction of a B=N
Manganese-mediated hydride delivery to a borazine by stepwise reduction and protonation.
Carter TJ, et al.
Organometallics, 33 (7), 1540-1543 (2014)
Anna S Lisovenko et al.
Inorganic chemistry, 49(22), 10357-10369 (2010-10-23)
Donor-acceptor complexes of borazine (BZ) and its substituted derivatives with Lewis acids (A = MCl(3), MBr(3); M = B, Al, Ga) and Lewis bases (D = NH(3), Py) have been theoretically studied at the B3LYP/TZVP level of theory. The calculations
Recyclable Trifluoromethylation Reagents from Fluoroform.
Geri J B and Szymczak N K
Journal of the American Chemical Society, 139(29), 9811-9814 (2017)
Jacob B Geri et al.
Journal of the American Chemical Society, 139(29), 9811-9814 (2017-07-14)
We present a strategy to rationally prepare CF3- transfer reagents at ambient temperature from HCF3. We demonstrate that a highly reactive CF3- adduct can be synthesized from alkali metal hydride, HCF3, and borazine Lewis acids in quantitative yield at room
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