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

2,2-Dimethyl-1,3-dioxane-4,6-dione Structure
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
MDL Number:
MFCD00006638
MOL File:
2033-24-1.mol
MSDS File:
SDS
Last updated:2024-04-02 17:31:45
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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)
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)  GHS hazard pictograms
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
1
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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
Product number Packaging Price Buy
210145 10g $29 Buy
210145 25g $52.2 Buy
M0799 25g $40 Buy
M0799 100g $96 Buy
A15603 25g $51.8 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 synthesis

141-82-2
67-64-1
2033-24-1
Synthesis of 2,2-Dimethyl-1,3-dioxane-4,6-dione from Malonic acid and Acetone

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( 724)Suppliers
Supplier Tel Email 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 12456 58
Shanghai UCHEM Inc. 		+862156762820 +86-13564624040 sales@myuchem.com China 6710 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 7845 58
Capot Chemical Co.,Ltd. 		571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Shanghai Daken Advanced Materials Co.,Ltd 		+86-371-66670886 info@dakenam.com China 15928 58
Beijing Cooperate Pharmaceutical Co.,Ltd 		010-60279497 sales01@cooperate-pharm.com CHINA 1811 55
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21691 55
Shanghai Time Chemicals CO., Ltd. 		+86-021-57951555 +8617317452075 jack.li@time-chemicals.com China 1807 55
Supplier Advantage
Xinxiang Hongqi District Houyuan Trading Co.,Ltd 		58
Hebei Mojin Biotechnology Co., Ltd 		58
Shanghai UCHEM Inc. 		58
Henan Bao Enluo International TradeCo.，LTD 		58
Henan Fengda Chemical Co., Ltd 		58
Capot Chemical Co.,Ltd. 		60
Shanghai Daken Advanced Materials Co.,Ltd 		58
Beijing Cooperate Pharmaceutical Co.,Ltd 		55
Henan Tianfu Chemical Co.,Ltd. 		55
Shanghai Time Chemicals CO., Ltd. 		55

Related articles

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
2,2-Dimethyl-1,3-dioxane-4,6-dione pictures 2024-04-26 2,2-Dimethyl-1,3-dioxane-4,6-dione
2033-24-1
 US $22.00-18.00 / kilograms 10kilograms 99% 100tons Hebei Dangtong Import and export Co LTD
2,2-Dimethyl-1,3-dioxane-4,6-dione pictures 2024-04-02 2,2-Dimethyl-1,3-dioxane-4,6-dione
2033-24-1
 US $32.00-1.20 / kg 1kg 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
2,2-dimethyl-1,3-dioxane-4,6-dione； Meldrum's acid; Isopropylidene malonate pictures 2024-02-23 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 Spectrum

2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)MS2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)1HNMR2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)13CNMR2,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)IR12,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)IR22,2-Dimethyl-1,3-dioxane-4,6-dione(2033-24-1)Raman

2033-24-1(2,2-Dimethyl-1,3-dioxane-4,6-dione)Related 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

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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%