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216690

Sigma-Aldrich

2,2,2-Triphenylacetophenone

98%

Synonym(s):

Benzopinacolone, Phenyl trityl ketone

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About This Item

Linear Formula:
(C6H5)3CCOC6H5
CAS Number:
466-37-5
Molecular Weight:
348.44
EC Number:
207-375-1
MDL number:
MFCD00004762
UNSPSC Code:
12352100
PubChem Substance ID:
24852973
NACRES:
NA.22

assay

98%

form

solid

mp

182-184 °C (lit.)

SMILES string

O=C(c1ccccc1)C(c2ccccc2)(c3ccccc3)c4ccccc4

InChI

1S/C26H20O/c27-25(21-13-5-1-6-14-21)26(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H

InChI key

CFBBKHROQRFCNZ-UHFFFAOYSA-N

General description

Asymmetric reduction of 2,2,2-triphenylacetophenone using with potassium 9-O-(1,2: 5, 6-di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclo [3.3.1] nonane (chiral reducing agent) has been reported. Dehydrative cyclization of 2,2,2-triphenylacetophenone has been reported.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Chiral synthesis via organoboranes. 15. Selective reductions. 42. Asymmetric reduction of representative prochiral ketones with potassium 9-O-(1, 2: 5, 6-di-O-isopropylidene-. alpha.-D-glucofuranosyl)-9-boratabicyclo [3.3. 1] nonane.
Brown HC, etal.
The Journal of Organic Chemistry, 53(6), 1231-1238 (1988)
Douglas A Klumpp et al.
Applied catalysis. A, General, 336(1-2), 128-132 (2008-03-01)
The hydroxyalkylation reactions of aceanthrenequinone (6) and acenapthenequinone (7) with a series of arenes have been studied. In reactions with the Brønsted superacid CF(3)SO(3)H (triflic acid), the condensation products are formed in good yields (58-99%, 10 examples) with high regioselectivity.

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