912395
NaBHT
Synonym(s):
Sodium butylated hydroxytoluene
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About This Item
Empirical Formula (Hill Notation):
C15H23NaO
CAS Number:
Molecular Weight:
242.33
UNSPSC Code:
12352111
NACRES:
NA.22
MDL number:
SMILES string
[Na+].[O-]c1c(cc(cc1C(C)(C)C)C)C(C)(C)C
InChI
1S/C15H24O.Na/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7;/h8-9,16H,1-7H3;/q;+1/p-1
InChI key
AOIQNBCUUALSSZ-UHFFFAOYSA-M
form
powder
storage temp.
−20°C
Quality Level
Application
NaBHT is an organic soluble base used for the Pd-catalyzed arylation of base-sensitve amines with aryl halides. NaBHT has also been show to be an efficient hydride source for the Pd-catalyzed reduction of aryl halides.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Abir Khadra et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(13), 3206-3212 (2017-01-10)
The Pd-PEPPSI-IPentCl precatalyst (PEPPSI=pyridine-enhanced precatalyst preparation stabilisation initiation) has been demonstrated to be highly effective in the coupling of hetero(aryl)chlorides to free 2-aminopyridine substrates to produce N-(hetero)aryl-2-aminopyridine derivatives. The catalyst has proven to be competent in a number of other
Sepideh Sharif et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(57), 13099-13103 (2019-09-21)
NaBHT (sodium butylated hydroxytoluene), a hindered and soluble base for the efficient arylation of various base-sensitive amines and (hetero)aryl halides has been found to have an unanticipated role as a hydride donor to reduce (hetero)aryl halides and allylic acetates. Mechanistic
Sepideh Sharif et al.
Angewandte Chemie (International ed. in English), 54(33), 9507-9511 (2015-06-23)
A single set of reaction conditions for the palladium-catalyzed amination of a wide variety of (hetero)aryl halides using primary alkyl amines has been developed. By combining the exceptionally high reactivity of the Pd-PEPPSI-IPent(Cl) catalyst (PEPPSI=pyridine enhanced precatalyst preparation, stabilization, and
A General Protocol for the Broad-Spectrum Cross-Coupling of Nonactivated Sterically Hindered 1° and 2° Amines
Khadra A, et al.
Organometallics, 36 (18), 3573-3577 (2017)
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