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900421

Sigma-Aldrich

9-Mesityl-3,6-di-tert-butyl-10-phenylacridinium tetrafluoroborate

≥95%

Synonym(s):

3,6-Bis(1,1-dimethylethyl)-10-phenyl-9-(2,4,6-trimethylphenyl)-acridinium tetrafluoroborate, 3,6-Di-tert-butyl-9-(2,4,6-trimethylphenyl)-10-phenylacridinium tetrafluoroborate

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About This Item

Empirical Formula (Hill Notation):
C36H40BF4N
CAS Number:
Molecular Weight:
573.51
UNSPSC Code:
12352005
NACRES:
NA.22

Quality Level

Assay

≥95%

form

powder or crystals

reaction suitability

core: acridinium
reagent type: catalyst
reaction type: Photocatalysis

mp

277.2 °C

photocatalyst activation

455 nm

SMILES string

[F-][B+3]([F-])([F-])[F-].C=1C=CC(=CC1)[N+]=2C=3C=C(C=CC3C(=C4C=CC(=CC42)C(C)(C)C)C=5C(=CC(=CC5C)C)C)C(C)(C)C

InChI

InChI=1S/C36H40N.BF4/c1-23-19-24(2)33(25(3)20-23)34-29-17-15-26(35(4,5)6)21-31(29)37(28-13-11-10-12-14-28)32-22-27(36(7,8)9)16-18-30(32)34;2-1(3,4)5/h10-22H,1-9H3;/q+1;-1

InChI key

YUNSHKYOOCWQRB-UHFFFAOYSA-N

Application

9-Mesityl-3,6-di-tert-butyl-10-phenylacridinium tetrafluoroborate is an acridium-based photocatalyst that can be an alternative to transition-metal-based photocatalysts due to its higher chemical stability and attenuated redox potential.
When employed with TEMPO, this acridinium photocatalyst promotes the site-selective amination of a variety of simple and complex aromatics with heteroaromatic azoles. When ammonium carbamate is used as the amine, anilines can be achieved directly.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Acridinium-Based Photocatalysts: A Sustainable Option in Photoredox Catalysis.
Joshi-Pangu A, et al.
The Journal of Organic Chemistry, 81(16), 7244-7249 (2016)

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