933-52-8

Basic information

• Product Name: TETRAMETHYL-1,3-CYCLOBUTANEDIONE
• Synonyms: TETRAMETHYL-1,3-CYCLOBUTANEDIONE;TETRAMETHYLCYCLOBUTANE-1,3-DIONE;TIMTEC-BB SBB008408;RARECHEM AQ C4 0041;DIMETHYL KETENE DIMER;2,2,4,4-TETRAMETHYL-1,3-CYCLOBUTANEDIONE;1,1,3,3-Tetramethylcyclobutanedione;2,2,4,4-Tetramethyl cyclobutane-1,3-dione
• CAS NO: 933-52-8
• Molecular Formula: C8H12O2
• Molecular Weight: 140.18
• EINECS: 213-269-6
• Product Categories: Organics;Cyclobutanes & Cyclobutenes;Simple 4-Membered Ring Compounds;C7 to C8;Carbonyl Compounds;Ketones;Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 933-52-8.mol
• Article Data: 21

Chemical Properties

• Melting Point: 114-116 °C(lit.)
• Boiling Point: 95-159 °C750 mm Hg(lit.)
• Flash Point: 120-122°C/150mm
• Appearance: /
• Density: 1.0373 (rough estimate)
• Vapor Pressure: 0.215mmHg at 25°C
• Refractive Index: 1.4580 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: It is soluble in chloroform.
• CAS DataBase Reference: TETRAMETHYL-1,3-CYCLOBUTANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAMETHYL-1,3-CYCLOBUTANEDIONE(933-52-8)
• EPA Substance Registry System: TETRAMETHYL-1,3-CYCLOBUTANEDIONE(933-52-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: GU1775000
• TSCA: Yes
• Hazardous Substances Data: 933-52-8(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

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.

Synthesis Reference(s)

Canadian Journal of Chemistry, 50, p. 3923, 1972 DOI: 10.1139/v72-619

Purification Methods

Crystallise the dione from *C6H6 and dry it in vacuo over P2O5 in an Abderhalden pistol. [Beilstein 7 III 3234, 7 IV 2004.]

InChI:InChI=1/C8H12O2/c1-7(2)5(9)8(3,4)6(7)10/h1-4H3

Upstream product

• 22922-58-3 dimethylmalonic anhydride 
• 121-44-8 triethylamine 
• 79-30-1 isobutyryl chloride 
• 861356-33-4 3,3,7,7,10,10-hexamethyl-[1,5]dioxecane-2,4,6,8,10-pentaone 
• 931-89-5 (E)-cyclooctene 
• 15848-07-4 thiobenzophenone S-oxide 
• 10181-59-6 2,2,4,4-tetramethyl-3-thioxocyclobutanone 
• 27378-01-4 silver ketenide 
• 74-88-4 methyl iodide 
• 598-26-5 dimethylketene 
• 598-26-5 dimethylketene cation radical 
• 97-72-3 2-Methylpropionic anhydride 
• 79-31-2 isobutyric Acid 
• 75-07-0 acetaldehyde 

Downstream Products

• 103-48-0 phenylethyl isobutyrate 
• 4447-70-5 2,2,4-Trimethyl-3-oxopentanoate 
• 590-35-2 2,2-dimethylpentane 
• 24642-79-3 1,1,3,3-tetramethylcyclobutane 
• 7374-59-6 1,1,3,3-tetrachloro-2,2,4,4-tetramethylcyclobutane 
• 1888-57-9 2,5-dimethylhexan-3-one 
• 565-80-0 2,4-dimethylpentan-3-one 
• 10181-56-3 2,2,4,4-tetramethylcyclobutane-1,3-dithione 
• 10181-59-6 2,2,4,4-tetramethyl-3-thioxocyclobutanone 
• 598-26-5 dimethylketene 
• 633303-45-4 3,3-dichloro-2,2,4,4-tetramethylcyclobutan-1-one 
• 814876-19-2 3,3-dichloro-2,2,4,4-tetramethylcyclobutanethione 
• 82338-36-1 2,2,4,4-tetramethylcyclopentenone (triphenylphosphoranylidene)hydrazone 
• 81396-36-3 2,2,5,5-tetramethylcyclopent-3-en-1-one 

Relevant articles and documents

Episulfidation of trans-Cyclooctene with an 1,2,4-Oxadithiolane

The dipolar cycloaddition of thiobenzophenone S-oxide (1) and 2,2,4,4-tetramethyl-3-thioxocyclobutanone (2) generates the labile 1,2,4-oxadithiolane I, which in the presence of trans-cyclooctene (3) affords trans-episulfide (9). In this direct sulfur tran

The fluoride anion-catalyzed sulfurization of thioketones with elemental sulfur leading to sulfur-rich heterocycles: First sulfurization of thiochalcones ?

Fluoride anion was demonstrated as a superior activator of elemental sulfur (S8) to perform sulfurization of thioketones leading to diverse sulfur-rich heterocycles. Due to solubility problems, reactions must be carried out either in THF using tetrabutylammonium fluoride (TBAF) or in DMF using cesium fluoride (CsF), respectively. The reactive sulfurizing reagents are in situ generated, nucleophilic fluoropolysulfide anions FS(8?x)?, which react with the C=S bond according to the carbophilic addition mode. Dithiiranes formed thereby, existing in an equilibrium with the ring-opened form (diradicals/zwitterions) are key-intermediates, which undergo either a step-wise dimerization to afford 1,2,4,5-tetrathianes or an intramolecular insertion, leading in the case of thioxo derivatives of 2,2,4,4-tetramethylcyclobutane-1,3-dione to ring enlarged products. In reactions catalyzed by TBAF, water bounded to fluoride anion via H-bridges and forming thereby its stable hydrates is involved in secondary reactions leading, e.g., in the case of 2,2,4,4-tetramethyl-3-thioxocyclobutanone to the formation of some unexpected products such as the ring enlarged dithiolactone and ring-opened dithiocarboxylate. In contrast to thioketones, the fluoride anion catalyzed sulfurization of their α,β-unsaturated analogues, i.e., thiochalcones is slow and inefficient. However, an alternative protocol with triphenylphosphine (PPh3) applied as a catalyst, offers an attractive approach to the synthesis of 3H-1,2-dithioles via 1,5-dipolar electrocyclization of the in situ-generated α,β-unsaturated thiocabonyl S-sulfides. All reactions occur under mild conditions and can be considered as attractive methods for the preparation of sulfur rich heterocycles with diverse ring-size.

Preparation method of 2, 2, 4, 4-tetramethyl-1, 3-cyclobutanediol

The invention discloses a preparation method of 2, 2, 4, 4-tetramethyl-1, 3-cyclobutanediol, which comprises the following steps: dissolving isobutyryl chloride in a first organic solvent, adding triethylamine and zinc powder while stirring, heating to reflux, reacting, cooling, filtering, washing, and carrying out reduced pressure distillation to obtain a distillation substrate; and dissolving the distillation substrate in a second organic solvent, cooling, filtering, introducing hydrogen under the action of a catalyst, and carrying out a reaction to obtain the product. According to the method, on the basis of the process of the BASF company, after triethylamine hydrochloride is formed by triethylamine serving as an acid-binding agent, triethylamine is released from the triethylamine hydrochloride by using proper metal, so that the triethylamine serving as the acid-binding agent can be recycled, and the triethylamine only plays a role of a bridge in a system; through continuous exchange and circulation of a small amount of triethylamine, the reaction is carried out until the reaction is complete.

PROCESS FOR PREPARING 2,2,4,4-TETRAMETHYL-1,3-CYCLOBUTANEDIOL

Disclosed is a method for preparing 2,2,4,4-tetramethyl-1,3-cyclobutanediol, which prepares (E) 2,2,4,4-tetramethyl-1,3-cyclobutanediol (CBDO) which is a final material by sequentially going through (A) methacrylic acid (MAA) as a raw material, and (B) isobutyric acid (IBA), (C) isobutyric anhydride (IBAN), and (D) 2,2,4,4-tetramethyl-1,3-cyclobutanedione (CBDK) as an intermediate. According to the present invention, the method for preparing 2,2,4,4-tetramethyl-1,3-cyclobutanediol which is economical and eco-friendly by optimizing preparation steps and maximizing the efficiency is provided.COPYRIGHT KIPO 2019