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ChemicalBook > Product Catalog >Chemical Reagents >Organic reagents >aliphatic ketones >2,2-Dimethyl-1,3-dioxane-4,6-dione

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

2,2-Dimethyl-1,3-dioxane-4,6-dione Structure
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
MOL File:
2033-24-1.mol
MSDS File:
SDS
Modify Date:
2024/4/2 17:31:45
Request For Quotation

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

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)

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
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2,2-Dimethyl-1,3-dioxane-4,6-dione price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 210145 2,2-Dimethyl-1,3-dioxane-4,6-dione 98% 2033-24-1 10G ₹1959.33 2022-06-14 Buy
Sigma-Aldrich(India) 210145 2,2-Dimethyl-1,3-dioxane-4,6-dione 98% 2033-24-1 25G ₹3658.85 2022-06-14 Buy
Sigma-Aldrich(India) 210145 2,2-Dimethyl-1,3-dioxane-4,6-dione 98% 2033-24-1 100G ₹8465.15 2022-06-14 Buy
ALFA India ALF-A15603-36 Isopropylidene malonate, 98% 2033-24-1 500g ₹19840 2022-05-26 Buy
TCI Chemicals (India) M0799 Meldrum's Acid (=2,2-Dimethyl-1,3-dioxane-4,6-dione) 2033-24-1 25G ₹4000 2022-05-26 Buy
Product number Packaging Price Buy
210145 10G ₹1959.33 Buy
210145 25G ₹3658.85 Buy
210145 100G ₹8465.15 Buy
ALF-A15603-36 500g ₹19840 Buy
M0799 25G ₹4000 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.

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.

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.

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.

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.

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 Ethyl propionylacetate Diethyl isopropylmalonate 3-CYCLOPROPYL-3-OXO-PROPIONIC ACID ETHYL ESTER
3-(4-Bromophenyl)propionic acid Ethyl isobutyrylacetate 3,4-Dimethoxyhydrocinnamic acid
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2,2-Dimethyl-1,3-dioxane-4,6-dione Suppliers

Global( 738)Suppliers
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GLR Innovations +91 9891111994 New Delhi, India 4542 58 Inquiry
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ALMELO PRIVATE LIMITED +91-9100991345 +91-8500807769 Telangana, India 114 58 Inquiry
Ergam Life Sciences Pvt. Ltd. +91-8125300959 +91-08125300959 Telangana, India 68 58 Inquiry
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GLR Innovations 58
SYNGREEN LIFESCIENCES PVT.LTD 58
NSR Laboratories Pvt. Ltd. 58
PURALABS 58
V B Organics 58
SRC Laboratories Pvt Ltd 58
VASISTA LIFE SCIENCES PRIVATE LIMITED 58
SVS INTERCHEM 58
ALMELO PRIVATE LIMITED 58
Ergam Life Sciences Pvt. Ltd. 58

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'MELDRUM'S ACID' LABOTEST-BB LT00233174 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 CYCLIC-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) 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 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 2,2-dimethyl-1,3-dioxane-4,6-quinone 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 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 2,2-Dimethyl-1,3-dioxane-4,6-dione In stock Factory Meldrum'sAcid(=2,2-Dimethyl-1,3-dioxane-4,6-dione)> 2,2-Dimethyl-1,3-dioxane-4,6-dione, 98%, for synthesis Meldrum's acMeldrum's acid id Sitagliptin Impurity 108 -1,3-dioxane-4,6-dione Meldrum'saci 2,2-Dimethyl-1,3-dioxane-4,6 Isopropylidene malonate (Meldrum's acid) Meldrum’s acid, ≥98%