3,3-Dimethyl-2-butanone

Base Information

• Chemical Name: 3,3-Dimethyl-2-butanone
• CAS No.: 75-97-8
• Molecular Formula: C6H12O
• Molecular Weight: 100.161
• Hs Code.: 29141990
• European Community (EC) Number: 200-920-4
• NSC Number: 935
• UNII: 3U1AAG3528
• DSSTox Substance ID: DTXSID5021752
• Nikkaji Number: J4.165C
• Wikipedia: Pinacolone
• Wikidata: Q222983
• ChEMBL ID: CHEMBL3183565
• Mol file: 75-97-8.mol

Synonyms:3,3-Dimethyl-2-butanone;Pinakolin [German];2-Butanone,3,3-dimethyl-;3,3-Dimethylbutanone;t-butyl methyl ketone;Pinacoline;Methyl t-butyl ketone;3,3-dimethylbutan-2-one;tert-Butyl methyl ketone;2, 2-Dimethyl-3-butanone;Ketone, tert-butyl methyl;2,2-Dimethyl-3-butanone;Methyltert-butyl ketone;2-Butanone, 3,3-dimethyl-;4-01-00-03310 (Beilstein Handbook Reference);1,1,1-Trimethylacetone;2,2-Dimethylbutanone;3, 3-Dimethyl-2-butanone;Ketone, t-butyl methyl;Pinacolin;Pinakolin;Methyl tert-butyl ketone;

Chemical Property of 3,3-Dimethyl-2-butanone

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 23.4mmHg at 25°C
• Melting Point: -52.5 °C
• Refractive Index: n20/D 1.396(lit.)
• Boiling Point: 104.9 °C at 760 mmHg
• Flash Point: 23.9 °C
• PSA: 17.07000
• Density: 0.802 g/cm³
• LogP: 1.62150
• Water Solubility.: 2.44 g/100 mL (15℃)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 100.088815002
• Heavy Atom Count: 7
• Complexity: 76.7

Purity/Quality:

98%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): F, Xn, Xi
• Hazard Codes: F:Flammable;;
• Statements: R11:; R22:
• Safety Statements: S16:; S20/21:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: CC(=O)C(C)(C)C

Technology Process of 3,3-Dimethyl-2-butanone

There total 307 articles about 3,3-Dimethyl-2-butanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-tert-Butyl-2-methyl-1,3-dioxolane (6135-54-2) + chloranil (118-75-2) → 3,3-dimethyl-butan-2-one (75-97-8) + 2,3,5,6-tetrachlorobenzene-1,4-diol (87-87-6) + C18Cl10O6

Guidance literature:

In acetonitrile; for 3h; Product distribution; Mechanism; Irradiation; various ketals under different reaction conditions;

DOI:10.1016/S0040-4020(96)01123-4

Reference yield:

2,3-Dimethyl-2-butene (563-79-1) → 2,3-dimethyl-2,3-epoxybutane (5076-20-0) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3,3-dimethyl-butan-2-one (75-97-8) + 3,3-dimethyldioxirane (74087-85-7) + hydroxy-2-propanone (116-09-6) + acetone (67-64-1)

Guidance literature:

With ozone; at -254.16 - -238.16 ℃; for 19h; Irradiation; Inert atmosphere;

DOI:10.1021/jp108457w

Reference yield:

3-methyl-3-tert-butyl-1,2-dioxetane (86954-72-5) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3,3-dimethyl-butan-2-one (75-97-8)

Guidance literature:

In xylene; at 60 ℃; Rate constant; Thermodynamic data; Mechanism; activation energy;

DOI:10.1021/jo00169a020

upstream raw materials:

tetrachloromethane

3,4,4-trimethyl-pent-2-enoic acid

phthalic anhydride

2,3-dimethyl-2,3-butane diol

Downstream raw materials:

(4E,6E)-2,2-dimethyl-7-phenylhepta-4,6-dien-3-one

2,2-dimethyl-5-(3-pyridyl)pentane-3,5-dione

2,2-dimethyl-5-(4-pyridyl)pentane-3,5-dione

(E)-4,4-dimethyl-1-(3,4-methylenedioxyphenyl)pent-1-en-3-one

Refernces

• 1、 Uchida, Sayaka,Lesbani, Aldes,Ogasawara, Yoshiyuki,Mizuno, Noritaka. "Ionic crystals [M3O(OOCC6H5) 6(H2O)3]4[α-SiW 12O40] (M = Cr, Fe) as heterogeneous catalysts for pinacol rearrangement". . p. 775 - 777. Retrieved 2012.
• 2、 Ikushima, Yutaka,Hatakeda, Kiyotaka,Sato, Osamu,Yokoyama, Toshirou,Arai, Masahiko. "Acceleration of synthetic organic reactions using supercritical water: Noncatalytic Beckmann and pinacol rearrangements". . p. 1908 - 1918. Retrieved 2000.
• 3、 Arzoumanian et al.. "". . p. 3445. Retrieved 1974.
• 4、 Ogiwara, Naoki,Tamai, Nanako,Uchida, Sayaka,Weng, Zhewei,Yan, Li-Kai,Zhao, Congcong,Zhou, Wei. "Isomeric effects on the acidity of Al13Keggin clusters in porous ionic crystals". supporting information. p. 8893 - 8896. Retrieved 2021/09/10.
• 5、 Ye, Danfeng,Liu, Zhiyuan,Sessler, Jonathan L.,Lei, Chuanhu. "Base-free oxidation of alcohols enabled by nickel(ii)-catalyzed transfer dehydrogenation". supporting information. p. 11811 - 11814. Retrieved 2020/10/13.