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

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

Iupac Name:2,2-dimethyl-1,3-dioxane-4,6-dione
CAS No.: 2033-24-1
Molecular Weight:144.12532
Modify Date.: 2022-11-29 09:07
Introduction: Meldrum`s acid is an intermediate for different organic syntheses. For typical reactions please consult the Meldrum`s acid brochure, which you can order. Contact us. Product Data Sheet View more+
1. Names and Identifiers
1.1 Name
2,2-Dimethyl-1,3-dioxane-4,6-dione
1.2 Synonyms

1,3-Dioxane-4,6-dione, 2,2-dimethyl- 2,2-Dimethyl-1,3-dio 2,2-Dimethyl-4,6-diketo-1,3-dioxane cycl-Isopropylidene Malonate EINECS 217-992-8 Isopropyl Malonate isopropylidene malonate LABOTEST-BB LT00233174 MALONIC ACID CYCLIC ISOPROPYLIDENE ESTER Meldrum acid Meldrum&rsquos acid Meldrum’s acid, Malonic acid cyclic isopropylidene ester Meldrumacid Meldrumic acid MELDRUMS ACID 'MELDRUM'S ACID' MELDRUM'S ACID MFCD00006638 sub-Isopropyl malonate

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1.3 CAS No.
2033-24-1
1.4 CID
16249
1.5 EINECS(EC#)
217-992-8
1.6 Molecular Formula
C6H8O4 (isomer)
1.7 Inchi
InChI=1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3
1.8 InChIkey
GXHFUVWIGNLZSC-UHFFFAOYSA-N
1.9 Canonical Smiles
CC1(OC(=O)CC(=O)O1)C
1.10 Isomers Smiles
CC1(OC(=O)CC(=O)O1)C
2. Properties
2.1 Density
1.201
2.1 Melting point
92-96℃
2.1 Boiling point
356.7 °C at 760 mmHg
2.1 Refractive index
1.571
2.1 Flash Point
195.1 °C
2.1 Precise Quality
144.04200
2.1 PSA
52.60000
2.1 logP
0.21260
2.1 Solubility
dioxane: soluble5%, clear to very slightly hazy, colorless to faintly yellow
2.2 Appearance
Colorless Liqiud
2.3 Storage
Moisture Sensitive. Ambient temperatures.
2.4 Chemical Properties
Crystals, white to beige
2.5 Color/Form
White to Yellow Solid
2.6 pKa
5.1(at 25℃)
2.7 Water Solubility
2.5 g/100 mL (20 oC)
2.8 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 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
3.2 Usage
Meldrum`s acid is an intermediate for different organic syntheses. For typical reactions please consult the Meldrum`s acid brochure, which you can order. Contact us. Product Data Sheet
4. Safety and Handling
4.1 Hazard Codes
Xi; T
4.1 Risk Statements
R36/37/38
4.1 Safety Statements
S24/25;S37/39
4.1 Hazard Class
IRRITANT
4.1 Hazard Declaration
H315
4.1 RIDADR
NONH for all modes of transport
4.1 Caution Statement
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
4.1 WGK Germany
3
4.1 RTECS
JH0800000
4.1 Report

Reported in EPA TSCA Inventory.

4.2 Safety

Hazard Codes:?IrritantXi,?ToxicT
Risk Statements: 36/37/38-45?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R45:May cause cancer.
Safety Statements: 37/39-24/25-53-45-36-26?
S37/39:Wear suitable gloves and eye/face protection.?
S24/25:Avoid contact with skin and eyes.?
S53:Avoid exposure - obtain special instructions before use.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: JH0800000
F: 10-21

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4.3 Specification

?Meldrum's acid , its cas register number is 2033-24-1. It also can be called?2,2-Dimethyl-1,3-dioxane-4,6-dione ; 2,2-Dimethyl-4,6-dioxo-m-dioxane ; 2,2-Dimethyl-m-dioxane-4,6-dione ; Isopropylidene malonate ; m-Dioxane-4,6-dione, 2,2-dimethyl- ; 1,3-Dioxane-4,6-dione, 2,2-dimethyl- ; Malonic acid, cyclic isopropylidene ester (8CI) .It is a brown white solid. It is an intermediate for different organic syntheses.

4.4 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 180mg/kg (180mg/kg) ? U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04102,

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Usage
Isopropylidene malonate is an important reagent in synthetic chemistry and involved in the formation of new C-C bonds, rings, amides, esters, and acids. The presence of carbonyl groups at C-4 and C-6 positions favors the alkylation and acylation reactions due to its acidic nature. It is also employed as an antimicrobial agent. It is used in the preparation of 4-pyridyl-substituted heterocycles, 2-substituted indoles, isofraxidin and macrocyclic beta-keto lactones. Further, it is involved in the Knoevenagel condensation reaction with aldehydes.
9.1 Merck
14,5817
9.2 BRN
117310
9.3 Chemical Properties
Crystals, white to beige
9.4 Uses
Meldrum`s acid is an intermediate for different organic syntheses. For typical reactions please consult the Meldrum`s acid brochure, which you can order. Contact us. Product Data Sheet
9.5 Uses
An antimicrobial agent
9.6 Uses
In organic synthesis as a substitute for acyclic malonic esters and generally as a C3O2 synthon.
9.7 Uses
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.
9.8 Mesh Entry Terms
2,2-dimethyl-1,3-dioxane-4,6-dione
9.9 Manufacturing Info
1,3-Dioxane-4,6-dione, 2,2-dimethyl-: ACTIVE
10. Computational chemical data
  • Molecular Weight: 144.12532g/mol
  • Molecular Formula: C6H8O4
  • Compound Is Canonicalized: True
  • XLogP3-AA: 0.6
  • Exact Mass: 144.04225873
  • Monoisotopic Mass: 144.04225873
  • Complexity: 164
  • Rotatable Bond Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Topological Polar Surface Area: 52.6
  • Heavy Atom Count: 10
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccBgOAAAAAAAAAAAAAAAAAAAAAAAAAAkAAAAAAAAAAAAAAAAGgAAAAAACASAgAACCAAABAAIAACQCAAAAAAAAAAAAAEAAAAQAAQIAAAiAAABIAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
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