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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

Quality Level

100

Assay

98%

form

solid

mp

182-184 °C (lit.)

functional group

ketone
phenyl

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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

216690-BULK:
216690-5G:
216690-VAR:
216690-25G:

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Certificates of Analysis (COA)

Lot/Batch Number
03812DO
10915CY
07803EO
12702BN
01718TR

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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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