2,2-Dimethyl-1,3-dioxane-4,6-dione
- CAS No.
- 2033-24-1
- Chemical Name:
- 2,2-Dimethyl-1,3-dioxane-4,6-dione
- Synonyms
- MELDRUMS ACID;MELDRUM'S ACID;CYCL-ISOPROPYLIDENE MALONATE;ISOPROPYLIDENE MALONATE;Isopropyl Malonate;MALONIC ACID CYCLIC ISOPROPYLIDENE ESTER;Mie acid;Meldrumic acid;1,3-Dioxane-4,6-dione, 2,2-dimethyl-;Meldrum’s acid, Malonic acid cyclic isopropylidene ester
- CBNumber:
- CB8411057
- Molecular Formula:
- C6H8O4
- Molecular Weight:
- 144.13
- MDL Number:
- MFCD00006638
- MOL File:
- 2033-24-1.mol
- MSDS File:
- SDS
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 temp. | 2-8°C |
solubility | dioxane: soluble5%, clear to very slightly hazy, colorless to faintly yellow |
pka | 5.1(at 25℃) |
form | Crystals or Powder |
color | Brownish-white to beige-brown |
Water Solubility | 2.5 g/100 mL (20 ºC) |
Merck | 14,5817 |
BRN | 117310 |
InChIKey | GXHFUVWIGNLZSC-UHFFFAOYSA-N |
LogP | -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) |
SAFETY
Risk and Safety Statements
Symbol(GHS) | ![]() GHS07 |
|||||||||
---|---|---|---|---|---|---|---|---|---|---|
Signal word | Warning | |||||||||
Hazard statements | H315-H319-H335 | |||||||||
Precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a | |||||||||
Hazard Codes | Xi,T | |||||||||
Risk Statements | 36/37/38-45 | |||||||||
Safety Statements | 37/39-24/25-53-45-36-26 | |||||||||
WGK Germany | 3 | |||||||||
RTECS | JH0800000 | |||||||||
F | 10-21 | |||||||||
TSCA | Yes | |||||||||
HazardClass | IRRITANT | |||||||||
HS Code | 29322090 | |||||||||
NFPA 704 |
|
2,2-Dimethyl-1,3-dioxane-4,6-dione price More Price(44)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich | 210145 | 2,2-Dimethyl-1,3-dioxane-4,6-dione 98% | 2033-24-1 | 10g | $29 | 2024-03-01 | Buy |
Sigma-Aldrich | 210145 | 2,2-Dimethyl-1,3-dioxane-4,6-dione 98% | 2033-24-1 | 25g | $52.2 | 2024-03-01 | Buy |
TCI Chemical | M0799 | Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione) >98.0%(T) | 2033-24-1 | 25g | $40 | 2024-03-01 | Buy |
TCI Chemical | M0799 | Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione) >98.0%(T) | 2033-24-1 | 100g | $96 | 2024-03-01 | Buy |
Alfa Aesar | A15603 | Isopropylidene malonate, 98% | 2033-24-1 | 25g | $51.8 | 2024-03-01 | Buy |
2,2-Dimethyl-1,3-dioxane-4,6-dione Chemical Properties,Uses,Production
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.
Chemical Properties
The compound appears as white to beige crystals. It has a melting point of 94-95℃ (decomposition), is insoluble in water, and is soluble in ethanol and acetone.
Application
2,2-Dimethyl-1,3-dioxane-4,6-dione was used in the synthesis of:
macrocyclic β-keto lactone
4-pyridyl-substituted heterocycles
2-substituted indoles
isofraxidin.
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.
Preparation
2,2-Dimethyl-1,3-dioxane-4,6-dione 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.
Synthesis Reference(s)
Journal of the American Chemical Society, 70, p. 3426, 1948 DOI: 10.1021/ja01190a060
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.
Flammability and Explosibility
Non flammable
Purification Methods
Crystallise the dione from Me2CO/H2O. It is a synthon for the C3 malonic acid moiety. [Arnette et al. J Am Chem Soc 106 6759 1984, Bihlmayer et al. Monatsh Chem 98 564 1967, Review: McNab Chem Soc, Rev 7 345 1978, Chan & Huang Synthesis 452 1982, Beilstein 19/5 V 8.]
2,2-Dimethyl-1,3-dioxane-4,6-dione Preparation Products And Raw materials
Raw materials
Preparation Products
1of4
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
Xinxiang Hongqi District Houyuan Trading Co.,Ltd | +86-0373-3695376 +86-13937349994 | HYJM@houyuanjm.com | China | 300 | 58 |
Hebei Mojin Biotechnology Co., Ltd | +8613288715578 | sales@hbmojin.com | China | 12450 | 58 |
Shanghai UCHEM Inc. | +862156762820 +86-13564624040 | sales@myuchem.com | China | 7034 | 58 |
Hebei Guanlang Biotechnology Co,.LTD | +8619930503252 | daisy@crovellbio.com | China | 5828 | 58 |
Henan Bao Enluo International TradeCo.,LTD | +86-17331933971 +86-17331933971 | deasea125996@gmail.com | China | 2503 | 58 |
Henan Fengda Chemical Co., Ltd | +86-371-86557731 +86-13613820652 | info@fdachem.com | China | 20294 | 58 |
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD | +8615383190639 | admin@86-ss.com | China | 1000 | 58 |
Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29798 | 60 |
Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | info@dakenam.com | China | 16914 | 58 |
Beijing Cooperate Pharmaceutical Co.,Ltd | 010-60279497 | sales01@cooperate-pharm.com | CHINA | 1811 | 55 |
Related articles
- Synthesis methods of 2,2-Dimethyl-1,3-dioxane-4,6-dione
- 2,2-Dimethyl-1,3-dioxane-4,6-dione is an organic compound, which is a white solid at room temperature and decomposes when heat....
- Jun 14,2022
- Application and toxicological of 2,2-Dimethyl-1,3-dioxane-4,6-dione
- Meldrum’s acid (2,2-dimethyl-1,3-dioxane-4,6-dione; isopro-pylidene malonate) is an organic compound, discovered in 1908 by A.....
- Apr 12,2022
- Uses and Synthesis of Meldrum’s acid
- Meldrum’s acid has attracted considerable attention due to its high acidity (pKa = 4.97) and rigid cyclic structure. Acylated ....
- Mar 22,2022
View Lastest Price from 2,2-Dimethyl-1,3-dioxane-4,6-dione manufacturers
Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
---|---|---|---|---|---|---|---|---|
![]() |
2024-08-24 | 2,2-Dimethyl-1,3-dioxane-4,6-dione
2033-24-1
|
US $1000.00-400.00 / kg | 1kg | 99% | 5000 | HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD | |
![]() |
2024-08-22 | 2,2-Dimethyl-1,3-dioxane-4,6-dione
2033-24-1
|
US $0.00 / KG | 25KG | 98%min | 30tons/month | WUHAN FORTUNA CHEMICAL CO., LTD | |
![]() |
2024-08-07 | 2,2-dimethyl-1,3-dioxane-4,6-dione; Meldrum's acid; Isopropylidene malonate
2033-24-1
|
US $36.00 / kg | 1kg | 0.99 | 100kg | Shanghai UCHEM Inc. |
-
- 2,2-Dimethyl-1,3-dioxane-4,6-dione
2033-24-1
- US $1000.00-400.00 / kg
- 99%
- HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
-
- 2,2-Dimethyl-1,3-dioxane-4,6-dione
2033-24-1
- US $0.00 / KG
- 98%min
- WUHAN FORTUNA CHEMICAL CO., LTD
-
- 2,2-dimethyl-1,3-dioxane-4,6-dione; Meldrum's acid; Isopropylidene malonate
2033-24-1
- US $36.00 / kg
- 0.99
- Shanghai UCHEM Inc.