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

Base Information

• Chemical Name: 3,6-Dimethyl-1,4-dioxane-2,5-dione
• CAS No.: 95-96-5
• Deprecated CAS: 116559-43-4,137566-94-0,153381-12-5,219616-64-5,51019-72-8,615-95-2,87760-46-1,340821-71-8,612845-77-9,1310566-98-3,1351306-95-0,1415890-67-3,2129300-88-3,2324093-62-9,2649110-75-6,1310566-98-3,1351306-95-0,137566-94-0,1415890-67-3,153381-12-5,219616-64-5,340821-71-8,51019-72-8,612845-77-9,615-95-2,87760-46-1
• Molecular Formula: C6H8O4
• Molecular Weight: 144.127
• Hs Code.: 29322090
• European Community (EC) Number: 202-468-3,608-832-1
• NSC Number: 403080
• UNII: 7EH08MWO6M
• DSSTox Substance ID: DTXSID7041253
• Nikkaji Number: J4.715E
• Wikipedia: Lactide
• Wikidata: Q421313
• RXCUI: 2550708
• ChEMBL ID: CHEMBL3185272
• Mol file: 95-96-5.mol

Synonyms:3,6-dimethyl-1,4-dioxane-2,5-dione;dilactide;lactide

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

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.311Pa at 25℃
• Melting Point: 116-119 °C
• Boiling Point: 285.5 °C at 760 mmHg
• Flash Point: 150.6 °C
• PSA: 52.60000
• Density: 1.186 g/cm³
• LogP: -0.13660
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in chloroform and methanol. Slightly soluble in benzene.
• Water Solubility.: 16.3g/L at 20℃
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 144.04225873
• Heavy Atom Count: 10
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

DL-Lactide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC1C(=O)OC(C(=O)O1)C
• Uses: DL-Lactide is used to produce 2-hydroxy-propionic acid 1-(1-phenyl-ethoxycarbonyl)-ethyl ester. It acts as an important raw material and an intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyes. It is involved in enzymatic alcoholysis to produce both alkyl (R)-lactates and alkyl (S,S)-lactyllactates.DL-Lactide is often used as a protective layer in wound coatings, or as anchors, screws or mesh in surgery, since it degrades in about six months to the innocuous lactic acid. Enzymatic alcoholysis of this racemic lactide catalyzed by commercial Novozym? 435 produces both alkyl (R)-lactates and alkyl (S,S)-lactyllactates in good yield and high enantiopurity. DL-Lactide is used to produce 2-hydroxy-propionic acid 1-(1-phenyl-ethoxycarbonyl)-ethyl ester. It acts as an important raw material and an intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyes. It is involved in enzymatic alcoholysis to produce both alkyl (R)-lactates and alkyl (S,S)-lactyllactates.

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

There total 33 articles about 3,6-Dimethyl-1,4-dioxane-2,5-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: 98.6%

(3R,6S)-3,6-dimethyl-1,4-dioxane-2,5-dione (13076-19-2,26680-10-4,26969-66-4,615-95-2) → D,L-lactide (95-96-5,26680-10-4,26969-66-4,615-95-2)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; tris(pentafluorophenyl)borate; In toluene; at 20 ℃; for 0.0833333h; Reagent/catalyst; Solvent; Temperature; Catalytic behavior; Glovebox; Inert atmosphere;

DOI:10.1021/jacs.5b08658

Reference yield: 95.8%

LACTIC ACID (849585-22-4,106989-11-1,26811-96-1,31587-11-8,26100-51-6) → D,L-lactide (95-96-5,26680-10-4,26969-66-4,615-95-2)

Guidance literature:

With poly(dioctylstannane); at 150 - 200 ℃; for 4h; under 0.1 - 760 Torr; Inert atmosphere; Dean-Stark;

Reference yield: 73.0%

Ammonium lactate (515-98-0) → D,L-lactide (95-96-5,26680-10-4,26969-66-4,615-95-2)

Guidance literature:

With ytterbium(III) triflate; In 5,5-dimethyl-1,3-cyclohexadiene; at 180 ℃; for 14h; Reagent/catalyst;

upstream raw materials:

ethyl 2-hydroxypropionate

L-Lactic acid

D-Lactic acid

LACTIC ACID

Downstream raw materials:

benzyl dilactate

2,3-Pentanedione

2-acetoxypropionic acid

acetaldehyde

Refernces

Behavior of Mixed Halogenated Phenols in the Zincke Method of Nitration

10.1021/ja01332a059

The study investigates the behavior of mixed halogenated phenols and cresols in the Zincke method of nitration. Various mixed halogenated phenols, such as 2-bromo-4-chlorophenol, 2-chloro-4-bromophenol, and their derivatives, were prepared and subjected to nitration. The researchers observed that when bromine occupies both ortho and para positions in a phenol or cresol, isomeric mononitro compounds can be formed. For the first time, it was shown that a phenol with hydrogen in one ortho position and bromine in the other can undergo nitration at both positions in the same experiment. Chlorine was found not to be replaceable by the nitro group under the studied conditions. The study also provided further evidence supporting the view that only one acetyl-benzoyl derivative can be prepared from an o-aminophenol regardless of the order of introduction of the acyl radicals.