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
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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
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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:?
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
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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
7. Synthesis Route
2033-24-1Total: 22 Synthesis Route
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
-
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..
-
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..
-
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..
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