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

3D Mol Similar

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+

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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; View all

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:?Xi,?T
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; View all

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

6. NMR Spectrum

Mass spectrum (electron ionization)

7. Synthesis Route

2033-24-1Total: 22 Synthesis Route

141-82-2 171 Suppliers

2033-24-1 268 Suppliers

Literatures:
Zhurnal Obshchei Khimii, , vol. 20, p. 425,600; engl. Ausg. S. 449, 635
Yield: null

108-22-5 44 Suppliers

2033-24-1 268 Suppliers

Literatures:
US4576746 A1, ;
Yield: null

7270-63-5 22 Suppliers

2033-24-1 268 Suppliers

Literatures:
Russian Journal of Organic Chemistry, , vol. 42, # 8 p. 1213 - 1219
Yield: null

View all

8. Precursor and Product

precursor:

64-17-5

34107-52-3

38806-12-1

1214-54-6

141-52-6

68695-08-9

67-56-1

141-82-2

105-53-3

594-71-8

108-22-5

996-82-7

7270-63-5

View all

product :

25464-86-2

70912-53-7

70912-52-6

3709-28-2

56766-77-9

2231-66-5

75307-61-8

15568-87-3

3962-41-2

66696-76-2

75307-68-5

759-36-4

75307-67-4

72324-46-0

85920-63-4

3709-18-0

66145-20-8

81710-05-6

15795-47-8

3709-32-8

26250-90-8

72651-98-0

75307-59-4

72651-95-7

7270-63-5

View all

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

"What is the Synthesis Method for Meldrum's Acid and Its Applications in Organic Synthesis? Jun 14 2022
Title: "What is the Synthesis Method for Meldrum's Acid and Its Applications in Organic Synthesis?" Introduction: Meldrum's acid, also known as 2,2-Dimethyl-4,6-dioxo-l,3-dioxane, is a versatile compo..
What Makes Meldrum's Acid a Versatile Tool in Organic Synthesis? Apr 12 2022
Meldrum's acid, also known as 2,2-dimethyl-1,3-dioxane-4,6-dione or isopropylidene malonate, is an organic compound that was discovered in 1908 by A. N. Meldrum. However, it took 40 years for the corr..
What is Meldrum's Acid and its Applications in Organic Synthesis? Mar 20 2022
General Description Meldrum's acid, also known as 2,2-dimethyl-1,3-dioxane-4,6-dione or isopropylidene malonate, is an organic compound discovered by A.N. Meldrum in 1908. Initially misidentified as a..