Tetramethyl-1,3-cyclobutanedione

Base Information

• Chemical Name: Tetramethyl-1,3-cyclobutanedione
• CAS No.: 933-52-8
• Molecular Formula: C8H12 O2
• Molecular Weight: 140.182
• Hs Code.: 2914290090
• European Community (EC) Number: 213-269-6
• NSC Number: 72172,46472
• UNII: RT4AQ22KS4
• DSSTox Substance ID: DTXSID4044745
• Nikkaji Number: J33.998I
• Wikipedia: 2,2,4,4-Tetramethylcyclobutanedione
• Wikidata: Q27288281
• ChEMBL ID: CHEMBL3183999
• Mol file: 933-52-8.mol

Synonyms:933-52-8;Tetramethyl-1,3-cyclobutanedione;Tetramethylcyclobutane-1,3-dione;2,2,4,4-tetramethylcyclobutane-1,3-dione;1,3-Cyclobutanedione, 2,2,4,4-tetramethyl-;2,2,4,4-TETRAMETHYL-1,3-CYCLOBUTANEDIONE;Dimethyl Ketene Dimer;Tetramethylcyclobuta-1,3-dione;1,1,3,3-Tetramethylcyclobutanedione;2,2,4,4-Tetramethylcyclobutanedione;NSC 72172;HSDB 5522;EINECS 213-269-6;NSC 46472;UNII-RT4AQ22KS4;RT4AQ22KS4;AI3-15918;DTXSID4044745;Tetramethyl-1.3-cyclobutanedione;MFCD00001331;NSC-46472;NSC-72172;2,2,4,4-tetramethyl-cyclobutane-1,3-dione;1,3,3-Tetramethylcyclobutanedione;2,4,4-Tetramethylcyclobutanedione;WLN: L4V CVTJ B1 B1 D1 D1;2,4,4-Tetramethyl-1,3-cyclobutanedione;Dimethylkene dimer;NCIOpen2_000393;SCHEMBL820210;CHEMBL3183999;DTXCID2024745;NSC46472;NSC72172;Tox21_301434;AKOS004910158;SB12445;Tetramethyl-1,3-cyclobutanedione, 99%;1.1.3.3-Tetramethylcyclobutandion-2.4;NCGC00256072-01;AS-50366;CAS-933-52-8;LS-55895;SY048707;2,2,4,4-tetramethylcyclobutan-1,3-dione;2, 2,4,4-tetramethyl-1,3-cyclobutanedione;CS-0047858;D0258;FT-0676077;2,2,4,4-Tetramethyl cyclobutane-1,3-dione;EN300-160112;P10002;A859826;J-640318;J-800321;Q27288281

Chemical Property of Tetramethyl-1,3-cyclobutanedione

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.215mmHg at 25°C
• Melting Point: 114-116 °C(lit.)
• Refractive Index: 1.4580 (estimate)
• Boiling Point: 95-159 °C750 mm Hg(lit.)
• Flash Point: 74.3°C
• PSA: 34.14000
• Density: 0.995g/cm³
• LogP: 1.19060
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: It is soluble in chloroform.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 140.083729621
• Heavy Atom Count: 10
• Complexity: 167

Purity/Quality:

99% ^*data from raw suppliers

Tetramethyl-1,3-Cyclobutanedione ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC1(C(=O)C(C1=O)(C)C)C
• Uses: Tetramethyl-1,3-cyclobutanedione is used as a chemical for life science research. It is also used to make other chemical, as well as an chemical and organic intermediate.

Technology Process of Tetramethyl-1,3-cyclobutanedione

There total 31 articles about Tetramethyl-1,3-cyclobutanedione 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: 85.0%

cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole (80409-75-2,343865-40-7) + isobutyryl chloride (79-30-1) → 2,2,4,4-tetramethyl-1,3-cyclobutanedione (933-52-8) + (2aS,4aS,7aR,7bS)-2,2,6,6-Tetramethyl-2a,4a,7a,7b-tetrahydro-2H-5,7-dioxa-cyclobuta[e]inden-1-one

Guidance literature:

With triethylamine; In tetrahydrofuran; for 27h; Heating;

DOI:10.1021/ja076663z

Reference yield: 72.0%

1,1,3,3-tetramethyl-8-thia-5,6-diazaspiro[3.4]oct-5-en-2-one (23604-61-7) → 2,2,4,4-tetramethyl-1,3-cyclobutanedione (933-52-8)

Guidance literature:

With water; trifluoroacetic acid; In tetrahydrofuran; at 40 ℃; for 8h;

DOI:10.1002/1522-2675(20010613)84:6<1805::AID-HLCA1805>3.0.CO;2-T

Reference yield: 71.7%

isobutyryl chloride (79-30-1) → 2,2,4,4-tetramethyl-1,3-cyclobutanedione (933-52-8)

Guidance literature:

With triethylamine; zinc; In ethyl acetate; at 40 - 68 ℃; for 20.5h;

upstream raw materials:

dimethylketene

dimethylmalonic anhydride

triethylamine

isobutyryl chloride

Downstream raw materials:

5-hydroxy-2,4,4,5-tetramethyl-hexan-3-one

acetone

2,4-dimethylpentan-3-one

benzophenone

Refernces

• 1、 Mloston, Grzegorz,Romanski, Jaroslaw,Linden, Anthony,Heimgartner, Heinz. "Unexpected products from the reaction of 2,2,4,4-tetramethylcyclobutane- 1,3-dione with the Makosza reagent". . p. 1302 - 1310. Retrieved 1999.
• 2、 Binsch et al.. "". . p. 4497. Retrieved 1968.
• 3、 -. "Tetramethylcyclobutanedione and tetramethylcyclobutane diol Method for manufacturing the same". Paragraph 0043-0074. . Retrieved 2021/09/29.
• 4、 -. "PROCESS FOR PREPARING 2,2,4,4-TETRAMETHYL-1,3-CYCLOBUTANEDIOL". Paragraph 0094; 0095. . Retrieved 2019/10/22.