2,2,5-Trimethyl-1,3-dioxane-4,6-dione

Base Information

• Chemical Name: 2,2,5-Trimethyl-1,3-dioxane-4,6-dione
• CAS No.: 3709-18-0
• Molecular Formula: C7H10O4
• Molecular Weight: 158.154
• Hs Code.: 29171990
• European Community (EC) Number: 223-050-7
• NSC Number: 233870
• UNII: K6BV95MJT8
• DSSTox Substance ID: DTXSID90190585
• Nikkaji Number: J205.624K
• Wikidata: Q72514033
• Mol file: 3709-18-0.mol

Synonyms:2,2,5-Trimethyl-1,3-dioxane-4,6-dione;3709-18-0;Methyl Meldrum's acid;K6BV95MJT8;1,3-Dioxane-4,6-dione, 2,2,5-trimethyl-;EINECS 223-050-7;MFCD00006637;NSC-233870;2,2,5-trimethyl-1,3-dioxan-4,6-dione;NSC233870;UNII-K6BV95MJT8;SCHEMBL146063;KJMCAXYHYPDRAV-UHFFFAOYSA-;AMY7670;DTXSID90190585;BCP03720;AKOS015904420;CS-W016208;NSC 233870;2,2,5-Trimethyl-m-dioxane-4,6-dione;AS-13414;SY042991;1,3-Dioxane-4,6-dione2,2,5-trimethyl;FT-0634986;D71065;EN300-157893;2,2,5-Trimethyl-1,3-dioxane-4,6-dione, 97%;A823529;W-106569;4-Nitrobenzyl-(1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[(diphenylphosphono)oxy]-1-methylcarbapen-2-em-3-ca

Chemical Property of 2,2,5-Trimethyl-1,3-dioxane-4,6-dione

Chemical Property:

• Appearance/Colour: White to slightly pink crystalline powder
• Vapor Pressure: 6.96E-05mmHg at 25°C
• Melting Point: 111-114 °C(lit.)
• Refractive Index: 1.427
• Boiling Point: 343.6 °C at 760 mmHg
• PKA: 13.14±0.40(Predicted)
• Flash Point: 183.4 °C
• PSA: 52.60000
• Density: 1.13 g/cm³
• LogP: 0.45860
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 187

Purity/Quality:

99.5% ^*data from raw suppliers

2,2,5-Trimethyl-1,3-dioxane-4,6-dione ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(=O)OC(OC1=O)(C)C
• Uses: 2,2,5-Trimethyl-1,3-dioxane-4,6-dione is used as a reagent in the synthesis of 3'',4''-bis-difluoromethoxycinnamoylanthranilate (FT061) which is an orally-active antifibrotic agent that reduces albuminuria in rat models of progressive diabetic nephropathy. 2,2,5-Trimethyl-1,3-dioxane-4,6-dione was used for trapping the adduct formed during the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates.

Technology Process of 2,2,5-Trimethyl-1,3-dioxane-4,6-dione

There total 33 articles about 2,2,5-Trimethyl-1,3-dioxane-4,6-dione 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: 94.0%

2,2,5-trimethyl-5-(1-((4-octyloxy)phenyl)ethyl)-1,3-dioxane-4,6-dione → 2,2,5-trimethyl-1,3-dioxane-4,6-dione (3709-18-0) + 1-ethyl-4-octyloxybenzene (1379023-18-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 65 ℃; for 24h; under 760.051 Torr; Sealed tube;

DOI:10.1002/adsc.201600535

Reference yield: 84.0%

methyl-propanedioic acid (516-05-2) + acetone (67-64-1) → 2,2,5-trimethyl-1,3-dioxane-4,6-dione (3709-18-0)

Guidance literature:

With sulfuric acid; acetic anhydride; at 20 ℃; for 6h; Cooling with ice;

DOI:10.3762/bjoc.17.135

Reference yield: 80.0%

5-(4-octyloxybenzyl)-2,2,5-trimethyl-1,3-dioxane-4,6-dione → 2,2,5-trimethyl-1,3-dioxane-4,6-dione (3709-18-0) + 1-methyl-4-(octyloxy)benzene (67698-82-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 65 ℃; for 24h; under 760.051 Torr; Solvent; Temperature; Sealed tube;

DOI:10.1002/adsc.201600535

upstream raw materials:

methyl-propanedioic acid

acetone

1-<(6-hydroxy-2,2-dimethyl-4-oxo-4H-1,3-dioxin-5-yl)methyl>pyridinium hydroxide

5-dimethylsulfonio-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide

Downstream raw materials:

6-(tert-Butyl-diphenyl-silanyloxy)-2,2,5-trimethyl-[1,3]dioxin-4-one

rac-2-methyl-3-oxo-3-(phenylthio)propanoic acid

Refernces

• 1、 Oliveira, Jo?o A.C.,Kiala, Gredy,Siopa, Filipa,Bernard, Aurélie,Gontard, Geoffrey,Oble, Julie,Afonso, Carlos A.M.,Poli, Giovanni. "Palladium-catalyzed allylic substitution between C-based nucleophiles and 6-azabicyclo[3.1.0]-hex-3-en-2-oxy derivatives: A new selectivity paradigm". . . Retrieved 2020.
• 2、 Yu, Jin-Sheng,Noda, Hidetoshi,Shibasaki, Masakatsu. "Quaternary β2,2-Amino Acids: Catalytic Asymmetric Synthesis and Incorporation into Peptides by Fmoc-Based Solid-Phase Peptide Synthesis". supporting information. p. 818 - 822. Retrieved 2017/12/26.