2,2-Dimethyl-1,3-dioxane-4,6-dione
MELDRUM'S ACID · Meldrum’s acid · MELDRUMS ACID · CYCL-ISOPROPYLIDENE MALONATE · ISOPROPYLIDENE MALONATE · Isopropyl Malonate · MALONIC ACID CYCLIC ISOPROPYLIDENE ESTER · Mie acid
Identifiers & Physical Properties
| CAS No. | 2033-24-1 |
|---|---|
| Molecular formula | C6H8O4 |
| Average molar mass | 144.12 g/mol |
| Monoisotopic mass | 144.04225874 g/mol |
| SMILES | CC1(C)OC(=O)CC(=O)O1 |
| InChIKey | GXHFUVWIGNLZSC-UHFFFAOYSA-N |
| PubChem CID | 16249 |
| EC No. | 217-992-8 |
| DTXSID | DTXSID7051846 |
Chemical & Physical Properties
| XLogP | 0.6 |
|---|---|
| Topological polar surface area | 52.6 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 0 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 164 |
| Chemical classes | Other Classes -> Other Organic Compounds |
| SpringerMaterials Properties | Chemical shift |
| Physical Description | Solid[Merck Index] White powder[Alfa Aesar MSDS] |
| Melting point | 92-96 °C(lit.) |
| Boiling point | 182.71°C (rough estimate) |
| Density | 1.1311 (rough estimate) |
| Vapor pressure | 0.044-133Pa at 25℃ |
| Refractive index | 1.4434 (estimate) |
| Storage conditions | 2-8°C |
| Solubility | dioxane: soluble5%, clear to very slightly hazy, colorless to faintly yellow2.5 g/100 mL (20 ºC) |
| pKa (acidity coefficient) | 5.1(at 25℃) |
| Physical state | Crystals or Powder |
| Color | Brownish-white to beige-brown |
| Merck | 14,5817 |
| BRN | 117310 |
| InChI | 1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3 |
| InChIKey | GXHFUVWIGNLZSC-UHFFFAOYSA-N |
| SMILES | CC1(C)OC(=O)CC(=O)O1 |
| LogP (partition coefficient) | -1.58-4.786 at 25℃ |
| CAS DataBase Reference | 2033-24-1(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | DD139RP1SC |
| NIST Chemistry Reference | 1,3-Dioxane-4,6-dione, 2,2-dimethyl-(2033-24-1) |
| EPA Substance Registry System | 1,3-Dioxane-4,6-dione, 2,2-dimethyl- (2033-24-1) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xi,T |
| Risk statements (R) | 36/37/38-45 |
| Safety statements (S) | 37/39-24/25-53-45-36-26 |
| Water hazard class (WGK) | 3 |
| RTECS number | JH0800000 |
| F | 10-21 |
| TSCA inventory status | TSCA listed |
| Hazard class | IRRITANT |
| Customs code | 29322090 |
| Storage class | 11 - Combustible Solids |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 26.1% (12 of 46) of reports.WarningH315 (39.1%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 46 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: 1,3-Dioxane-4,6-dione, 2,2-dimethyl-Status: Active Update: 09-08-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/186351,3-Dioxane-4,6-dione, 2,2-dimethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Hazards summary | A skin and strong eye irritant[Alfa Aesar MSDS] See 1,3-Dioxane. |
| Hazard Classes and Categories | Skin Irrit. 2 (39.1%) |
| F | 10-21 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | JH0800000 |
| Customs code | 29322090 |
| Risk statements (R) | 36/37/38-45 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi,T |
| Safety statements (S) | 37/39-24/25-53-45-36-26 |
| Hazard class | IRRITANT |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| REACH registrations | Active |
| GHS precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
Applications & Uses
Description
Meldrum's acid, also known as 2,2-dimethyl-1,3-dioxane-4,6-dione, is an organic compound with the formula C6H8O4. The compound was first made in 1908 by Andrew Norman Meldrum by a condensation reaction of malonic acid with acetone in acetic anhydride and sulfuric acid. Meldrum misidentified the structure as a β-lactone of β-hydroxyisopropylmalonic acid. Yet Meldrum's acid has a high acidity with a pKa of 4.97, because like ascorbic acid, deprotonation at the methylene next to the carbonyls produces a stable enolate. Because of this property Meldrum's acid like malonic acid is a reactant in Knoevenagel condensations.
Uses
An antimicrobial agent
Uses
Meldrum's acid serves as an intermediate in a variety of organic synthesis reactions. It is commonly used as an alternative to acyclic malonic esters and generally acts as a C3O2 synthon in organic synthesis.
General Description
2,2-Dimethyl-1,3-dioxane-4,6-dione (Meldrum′s acid) is widely used in organic synthesis, especially for multiple C-C bond formations due to its adequate acidity (pKa 4.83) and steric rigidity. Knoevenagel condensation reaction between aldehydes and Meldrum′s acid are accelerated in ionic liquids.
Preparation & Synthesis
Preparation
2,2-Dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid)is usually prepared by condensation of malonic acid with acetone in acetic anhydride in the presence of sulfuric acid. Excellent yield of the product was achieved when acetic anhydride was added in a slow, controlled manner to a mixture of acetone, malonic acid and an acid catalyst.