P45605
3,3-Dimethyl-2-butanone
97%
Synonym(s):
α,α,α-Trimethylacetone, tert-Butyl methyl ketone, Pinacolone
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About This Item
Linear Formula:
CH3COC(CH3)3
CAS Number:
Molecular Weight:
100.16
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
200-920-4
Beilstein/REAXYS Number:
1209331
MDL number:
Assay:
97%
InChI
1S/C6H12O/c1-5(7)6(2,3)4/h1-4H3
InChI key
PJGSXYOJTGTZAV-UHFFFAOYSA-N
SMILES string
CC(=O)C(C)(C)C
assay
97%
refractive index
n20/D 1.396 (lit.)
bp
106 °C (lit.)
density
0.801 g/mL at 25 °C (lit.)
Quality Level
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Application
3,3-Dimethyl-2-butanone is an aliphatic ketone can undergo asymmetric reduction to the corresponding alcohol with diisopinocampheylchloroborane with high enantiomeric excess.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Flam. Liq. 2
Storage Class
3 - Flammable liquids
wgk
WGK 2
flash_point_f
41.0 °F - closed cup
flash_point_c
5 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Y Chen et al.
The Journal of organic chemistry, 66(11), 3930-3939 (2001-05-26)
To investigate the effects of electron-donating and electron-withdrawing substituents upon the reaction of porphyrins with osmium tetraoxide, and the pinacol-pinacolone rearrangement of the resulting diols, a series of meso-substituted porphyrins were prepared by total synthesis. Porphyrins with electron-donating substitutents at
Kosuke Namba et al.
Organic letters, 14(5), 1222-1225 (2012-02-22)
An efficient method for the construction of dihydroquinoline derivatives possessing a quaternary carbon center is developed by an application of Hg(OTf)(2)-catalyzed vinylogous semi-pinacol-type rearrangement. The reaction was found to be specifically catalyzed by mercury salt and to proceed via a
Highly efficient asymmetric reduction of. alpha.-tertiary alkyl ketones with diisopinocampheylchloroborane.
Brown H C, et al.
The Journal of Organic Chemistry, 51(17), 3394-3396 (1986)
Direct conversion of arylamines to pinacol boronates: a metal-free borylation process.
Fanyang Mo et al.
Angewandte Chemie (International ed. in English), 49(10), 1846-1849 (2010-02-04)
Makoto Shimizu et al.
Organic letters, 4(23), 4097-4099 (2002-11-09)
The pinacol reaction of beta-halogenated alpha,beta-unsaturated aldehydes was promoted by titanium tetraiodide to give coupling products in good yields with high dl-selectivity. Subsequent reduction with H(2)/Pd-C gave saturated vic-diols in good yields. Heck coupling reaction enabled the displacement of halogens
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