ChemicalBook > CAS DataBase List > 2,2-Dimethyl-1,3-dioxane-4,6-dione

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

Product Name
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
Formula Weight
144.13
MOL File
2033-24-1.mol
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2,2-Dimethyl-1,3-dioxane-4,6-dione Property

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)
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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
210145
Product name
2,2-Dimethyl-1,3-dioxane-4,6-dione
Purity
98%
Packaging
10g
Price
$29
Updated
2024/03/01
Sigma-Aldrich
Product number
210145
Product name
2,2-Dimethyl-1,3-dioxane-4,6-dione
Purity
98%
Packaging
25g
Price
$52.2
Updated
2024/03/01
TCI Chemical
Product number
M0799
Product name
Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione)
Purity
>98.0%(T)
Packaging
25g
Price
$40
Updated
2024/03/01
TCI Chemical
Product number
M0799
Product name
Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione)
Purity
>98.0%(T)
Packaging
100g
Price
$96
Updated
2024/03/01
Alfa Aesar
Product number
A15603
Product name
Isopropylidene malonate, 98%
Packaging
25g
Price
$51.8
Updated
2024/03/01
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2,2-Dimethyl-1,3-dioxane-4,6-dione Chemical Properties,Usage,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

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.

Uses

An antimicrobial agent

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

Malonic acid

Preparation Products

4-Chloroquinoline QUINOLINE-4-BORONIC ACID 6-bromoquinolin-4(3H)-one QUINOLINE-4-CARBOXYLIC ACID 7-DIETHYLAMINO-3-THENOYLCOUMARIN 3-(4-Nitrophenyl)propanoic acid 6-BROMO-4-CHLOROQUINOLINE 3-(2-THIENYL)PROPIONIC ACID 4-IODOQUINOLINE 4-Bromoquinoline 4,7-DIMETHOXY-1,10-PHENANTHROLINE, 97% 3-(4-NITRO-PHENYL)-PROPAN-1-OL
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View Lastest Price from 2,2-Dimethyl-1,3-dioxane-4,6-dione manufacturers

Hebei Mujin Biotechnology Co.,Ltd
Product
2,2-Dimethyl-1,3-dioxane-4,6-dione 2033-24-1
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-23
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
2,2-Dimethyl-1,3-dioxane-4,6-dione 2033-24-1
Price
US $1000.00-400.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-12
WUHAN FORTUNA CHEMICAL CO., LTD
Product
2,2-Dimethyl-1,3-dioxane-4,6-dione 2033-24-1
Price
US $0.00/KG
Min. Order
25KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-09

2033-24-1, 2,2-Dimethyl-1,3-dioxane-4,6-dioneRelated Search:

Diisopropyl malonate Isopropylmalonic acid Malonic acid Dimethyl carbonate Dimethyl sulfoxide Tris(trimethylsilyl)phosphate N,N-Dimethylformamide DIMETHYLGLYOXIME DISODIUM SALT Methyl acrylate Dimethyl fumarate Isopropyl acetate Dimethyl succinate Acetone oxime Isopropyl palmitate 1,4-Dioxane ETHANE Folic acid Citric acid

  • MELDRUMS ACID
  • 'MELDRUM'S ACID'
  • MELDRUM'S ACID
  • MALONIC ACID CYCLIC ISOPROPYLIDENE ESTER
  • LABOTEST-BB LT00233174
  • Isopropyl Malonate
  • Meldrum’s acid, Malonic acid cyclic isopropylidene ester
  • 2,2-DiMethyl-1,3-dioxane-4,6-dione, 98% 25GR
  • 2,2-Dimethyl-1,3-dioxane-4,6-dione cycl-Isopropylidene Malonate Malonic Acid Cyclic Isopropylidene Ester
  • 2,2-dimethyl-1,3-dioxane-4,6-diacetone
  • 2,2-Dimethyl-4,6-dioxo-m-dioxane
  • 2,2-Dimethyl-m-dioxane-4,6-dione
  • 2,2-dimethyl-m-dioxane-6-dione
  • Malonic acid, cyclic isopropylidene ester (8CI)
  • 4,6-Diketo-2,2-dimethyl-1,3-dioxane
  • 2，2-t×ù-1，3-táù·-4，6-tía
  • 2，2-t×ù-1，3-tfòíé-4，6-tía
  • tá·()òì±￥
  • Tá·()òì±￥;2,2-T×ù-1,3-Táù·-4,6-TíA;2,2-T×ù-1,3-TFòíé-4,6-TíA
  • 2,2-Dimethyl-1,3-dioxane-4,7-dione
  • CYCLIC-ISOPROPYLIDENE MALONATE
  • CYCL-ISOPROPYLIDENE MALONATE
  • ISOPROPYLIDENE MALONATE
  • 2,2-DIMETHYL-1,3-DIOXAN-4,6-DIONE
  • 2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE
  • AKOS B029723
  • SUB-ISOPROPYL MALONATE
  • MELDRUM'S ACID (2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE)
  • 2,2-Dimethyl-1,3-dioxane-4,6-dione (meldrum acid)
  • 1,3-Dioxane-4,6-dione, 2,2-dimethyl-
  • 2,2-DIMETHYL-1,3-DIOXANE-4,6-DIIONE
  • 2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE,99+%
  • 2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE (MELDRUM''S ACID)
  • Cycl-isopropylidene malonate ( Meldrum's Acid )
  • cycl-Isopropylidene malonate, Malonic acid cyclic isopropylidene ester, Meldrums acid
  • Meldrumic acid
  • 2,2-Dimethyl-4H-1,3-dioxin-4,6(5H)-dione
  • Malonic acid isopropylidene ester
  • Propanedioic acid isopropylidene ester
  • 2,2-Dimethyl-1,3-dioxane-4,6-dione,98%
  • 2,2-Dimethyl-1,3-dio
  • 6-dione,2,2-dimethyl-3-dioxane-4
  • m-Dioxane-4,6-dione, 2,2-dimethyl-
  • Meldrumacid
  • 2,2-Dimethyl-1,3-dioxane-4,6-dione~Malonic acid isopropylidene cyclic ester~Meldrums Acid
  • Malonic acid isopropylidene cyclicester
  • NSC 688343
  • NSC 71902
  • MeldruM's ac
  • 2,2-DiMethyl-1,3-dioxane-4,6-dione 98%
  • Malonic acid and isopropyl ester
  • Mie acid
  • 2,2-dimethyl-1,3-dioxane-4,6-quinone
  • Dimethyl-1,3-dioxane-4,6-dione
  • Meldrum's acid 2,2-Dimethyl-1,3-dioxan-4,6-dione
  • 2,2-Dimethyl-1,3-dioxane-4,6-dione 2033-24-1
  • Meldrum's acid 2033-24-1
  • Meldrum's acid 2033-24-1 Factory 2,2-Dimethyl-1,3-dioxane-4,6-dione