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912395

Sigma-Aldrich

NaBHT

Synonym(s):

Sodium butylated hydroxytoluene

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About This Item

Empirical Formula (Hill Notation):
C15H23NaO
CAS Number:
16654-89-0
Molecular Weight:
242.33
MDL number:
MFCD30474994
UNSPSC Code:
12352111
NACRES:
NA.22
Pricing and availability is not currently available.

form

powder

Quality Level

100

storage temp.

−20°C

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

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.

Other Notes

Sodium Butylated Hydroxytoluene (NaBHT) as a New and Efficient Hydride Source for Pd-Catalysed Reduction Reactions

related product

Product No.
Description
Pricing

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

912395-BULK:
912395-5G:
912395-1G:
912395-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7192
MKCV9698

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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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