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Methyl acetoacetate

CAS：105-45-3
MW:116.11522
MF：C5H8O3

Methyl acetoacetate, with the chemical formula C5H8O3 and CAS registry number 105-45-3, is a compound commonly used in organic synthesis. Flash point 158°F. Denser than water and slightly soluble in water. Vapors heavier than air. This colorless liquid, also known as acetoacetic ester or MAE, is characterized by its acetoacetic ester functional group, consisting of a ketone and an ester. Methyl acetoacetate serves as a versatile building block in the production of various pharmaceuticals, agrochemicals, and flavor compounds. It participates in numerous reactions such as Claisen condensation, Michael addition, and Knoevenagel condensation, making it valuable in the preparation of complex organic molecules. Its applications extend to the fields of medicinal chemistry, flavor and fragrance industry, and materials science, contributing significantly to the advancement of chemical synthesis and product development. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Methyl acetoacetate

1.2 Synonyms: 3-OXBUTANOIC ACID METHYL ESTER; 3-OXOBUTANOIC ACID METHYL ESTER; 3-OXOBUTYRIC ACID METHYL ESTER; ACETOACETIC ACID METHYL ESTER; ACETOACETIC ESTER (METHYL); ACETYL METHYL ACETATE; ACM; Butanoic acid, 3-oxo-, methyl ester; EINECS 203-299-8; HYL ACETOACETATE; Methyl 3-oxobutanoate; Methyl 3-Oxobutyrate; methyl acetoacetate(MAA); MFCD00008784;

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1.3 CAS No.: 105-45-3

1.4 CID: 7757

1.5 EINECS: 203-299-8

1.6 Molecular Formula: C5H8O3

1.7 Inchi: InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3

1.8 InChkey: WRQNANDWMGAFTP-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(=O)CC(=O)OC

1.10 Isomers Smiles: CC(=O)CC(=O)OC

2. Properties

2.1 Vapour pressure: 4.0 (Air= 1)

2.2 Solubility: 460 g/L (20 oC)

2.3 Viscosity: 1.704 cPa at 20 °C

2.4 VaporDensity: 4.0 (Air= 1)

2.5 Appearance: Colorless liquid.

2.6 Storage: Ambient temperatures.

2.7 Autoignition Temperature: 536 °F (USCG, 1999)

2.8 Carcinogenicity: Not listed by ACGIH, IARC,NTP, or California Proposition 65. Methyl acetoacetate Preparation Products And Raw materials Raw materials

2.9 Chemical Properties: Colorless, clear liquid

2.10 Color/Form: Colorless liquid

2.11 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes

2.12 Odor: Agreeable odor

2.13 PH: 3.8 (863g/l, H2O, 20℃)

2.14 pKa: 10.67±0.46(Predicted)

2.15 Water Solubility: 460 g/L (20 oC)

2.16 Spectral Properties: Index of refraction: 1.4184 at 20 deg C/D
MAX ABSORPTION (ALCOHOL): 240 NM (LOG E= 3.18)
SADTLER REFERENCE NUMBER: 65 (IR, PRISM)
MASS: 63210 (NIST/EPA/MSDC Mass Spectral Database 1990 version)
IR: 15003 (Sadtler Research Laboratories IR grating)
UV: HBCP
1H NMR: 10319 (Sadtler Research Laboratories Spectral Collection)

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2.17 Stability: Stable under normal temperatures and pressures.

2.18 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Description: Methyl acetoacetate (CAS 105-45-3) is a colorless liquid with a fruity odor. Its basic structure consists of a methyl group (CH3) attached to the acetoacetate functional group (CH3C(O)CH2COO-). This chemical is highly soluble in water and has a boiling point of 167-168°C. It is also flammable and should be handled with caution.

Applicable fields
Methyl acetoacetate has various applications in different fields:

Chemical Industry: In the chemical industry, methyl acetoacetate is used as a building block for the synthesis of various compounds. It serves as a precursor for the production of pharmaceuticals, agrochemicals, and dyes. The mechanism of action involves its reactivity with other chemicals to form new compounds.

Flavor and Fragrance Industry: Methyl acetoacetate is also utilized in the flavor and fragrance industry. It is used as a raw material for the synthesis of fruity and floral aroma compounds. Its mechanism of action involves contributing to the desired scent or flavor profile of the final product.

Storage Conditions
Methyl acetoacetate should be stored in a cool and dry place, away from direct sunlight.

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3.2 Produe Method: Methyl acetoacetate is produced by a reaction of methylacetate with sodium methoxide.

3.3 Usage: Methyl acetoacetate (MAA) is a starting material for the syntheses of alpha-substituted aceto- acetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives.

4. Safety and Handling

4.1 Octanol/Water Partition Coefficient: log Kow = -0.69 /Estimated/

4.2 Other Preventative Measures: If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

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4.3 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

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4.4 Fire Fighting Procedures: ... /Use/ foam, carbon dioxide, dry chemical.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.

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4.5 FirePotential: FIRE HAZARD: Moderate, when exposed to heat or flame.

4.6 Safety Profile: Moderately toxic by ingestion. A skin and severe eye irritant. Combustible when exposed to heat or flame. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

4.7 Formulations/Preparations: /Available as/ liquid grades, assay 98%

4.8 Protective Equipment and Clothing: Methyl... acetoacetate may be irritating /to eyes and skin/.

4.9 Skin, Eye, and Respiratory Irritations: Methyl... acetoacetate may be irritating /to eyes and skin/.

4.10 Safety: Hazard Codes:Xi
Risk Statements:36
36:Irritating to the eyes
Safety Statements:26
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:1
HS Code:29183000
Hazardous Substances Data:105-45-3(Hazardous Substances Data)

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4.11 Specification: Colorless, clear liquid
usageEng:Methyl acetoacetate (MAA) is a starting material for the syntheses of alpha-substituted aceto- acetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives.
Safety Statements:26
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

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4.12 Toxicity: May be harmful by inhalation, ingestion, or skin absorption. Causes eye irritation. May cause skin irritation.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention.
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

1H NMR : 90 MHz in CDCl3

IR : liquid film

Raman : 4880 A,200 M,liquid

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

105-45-3Total: 47 Synthesis Route

79-20-9 162 Suppliers

105-45-3 245 Suppliers

623-43-8 68 Suppliers

105-45-3 245 Suppliers

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8. Precursor and Product

precursor:

623-43-8

141-97-9

6330-25-2

2911-22-0

1487-49-6

79-20-9

771-03-9

4525-25-1

product:

623-58-5

4755-81-1

591-60-6

108-26-9

141-97-9

691-45-2

3600-18-8

3976-69-0

689-77-0

541-50-4

9. Computed Properties

Molecular Weight：116.11522g/mol
Molecular Formula：C₅H₈O₃
Compound Is Canonicalized：True
Exact Mass：0
XLogP3-AA：116.047344113
Monoisotopic Mass：116.047344113
Complexity：106
Rotatable Bond Count：3
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：3
Topological Polar Surface Area：43.4
Heavy Atom Count：：8
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：AAADccBgMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAACASAgAICCAAABAAIAICQCAAAAAAAAAAAAAEAAAAAABQIAAAAAAAEIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

Usage: Methyl acetoacetate is used as a chemical reagent used in the synthesis of pharmaceuticals. It participates in the Biginelli reaction, forming molecules including dihydropyrimidinones.Methyl acetoacetate (MAA) is used for the synthesis of alpha-substituted aceto- acetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives.

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Merck: 14,6009

BRN: 506727

Chemical Properties: Colorless, clear liquid

Uses: Methyl acetoacetate (MAA) is a starting material for the syntheses of alpha-substituted aceto- acetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives.

Uses: 3-Oxobutanoic Acid Methyl Ester is a chemical reagent used in the synthesis of pharmaceuticals. It participates in the Biginelli reaction, forming molecules including dihydropyrimidinones.

Production Methods: Methyl acetoacetate is produced by a reaction of methyl acetate with sodium methoxide.

General Description: A clear colorless liquid. Flash point 158°F. Denser than water and slightly soluble in water. Vapors heavier than air.

Air & Water Reactions: Very slightly soluble in water.

Reactivity Profile: Methyl acetoacetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides

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Hazard: Toxic by ingestion and inhalation.

Health Hazard: May be harmful by inhalation, ingestion, or skin absorption. Causes eye irritation. May cause skin irritation.

Safety Profile: Moderately toxic by ingestion. A skin and severe eye irritant. Combustible when exposed to heat or flame. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

Carcinogenicity: Not listed by ACGIH, IARC, NTP, or California Proposition 65.

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12. Related Questions

: What are the improved methods for the production of Methyl acetoacetate?Methyl acetoacetate is widely used in various fields such as pesticides, pharmaceuticals, dyes, polymer stabilizers, solvents, and organic synthesis. It serves as an intermediate for various fungicide..; What is the current research progress of Methyl acetoacetate?Background and overview Methyl acetoacetate is a colorless and transparent liquid with aromatic odor, relative density (d°) 1.0762, melting point -31.9℃, boiling point 171.7℃, refractive index (n°) ..; What are the applications of Methyl acetoacetate?Methyl acetoacetate has the molecular formula C5H8O3. This component itself has a strong odor, so it is necessary to wear protective clothing and masks in many processing companies to withstand its sm..; What will be the major enol form of methyl acetoacetate? I presume the best enol form would have a double bond between the two C=O" style="position: relative;" tabindex="0" id="MathJax-Element-2-Frame" class="MathJax">C=OC=O so they're conjugated, but I'm ..

13. Realated Product Infomation