Methyl acetoacetate
- Iupac Name：methyl 3-oxobutanoate
- CAS No.: 105-45-3
- Molecular Weight：116.11522
- Modify Date.: 2022-04-18 04:07
- Introduction: 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.
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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
- 1.3 CAS No.
- 105-45-3
- 1.4 CID
- 7757
- 1.5 EINECS(EC#)
- 203-299-8
- 1.6 Molecular Formula
- C5H8O3 (isomer)
- 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
- 3.1 Density
- 1.077
- 3.1 Melting point
- -80℃
- 3.1 Boiling point
- 169-170℃
- 3.1 Refractive index
- 1.4175-1.4295
- 3.1 Flash Point
- 67℃
- 3.1 Vapour pressure
- 1.54mmHg at 25°C
- 3.1 Precise Quality
- 116.04700
- 3.1 PSA
- 43.37000
- 3.1 logP
- 0.13850
- 3.1 Solubility
- 460 g/L (20 oC)
- 3.2 Viscosity
- 1.704 cPa at 20 °C
- 3.3 VaporDensity
- 4.0 (Air= 1)
- 3.4 Appearance
- Colorless liquid.
- 3.5 Storage
- Ambient temperatures.
- 3.6 Autoignition Temperature
- 536 °F (USCG, 1999)
- 3.7 Carcinogenicity
- Not listed by ACGIH, IARC,NTP, or California Proposition 65. Methyl acetoacetate Preparation Products And Raw materials Raw materials
- 3.8 Chemical Properties
- Colorless, clear liquid
- 3.9 Color/Form
- Colorless liquid
- 3.10 Decomposition
- When heated to decomposition it emits acrid smoke and irritating fumes
- 3.11 Odor
- Agreeable odor
- 3.12 PH
- 3.8 (863g/l, H2O, 20℃)
- 3.13 pKa
- 10.67±0.46(Predicted)
- 3.14 Water Solubility
- 460 g/L (20 oC)
- 3.15 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)
- 3.16 Stability
- Stable under normal temperatures and pressures.
- 3.17 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 4.1 Produe Method
- Methyl acetoacetate is produced by a reaction of methylacetate with sodium methoxide.
- 4.2 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
- 5.1 Symbol
- GHS07
- 5.1 Hazard Codes
- Xi
- 5.1 Signal Word
- Warning
- 5.1 Risk Statements
- R36
- 5.1 Safety Statements
- S26
- 5.1 Packing Group
- Z01
- 5.1 Octanol/Water Partition Coefficient
- log Kow = -0.69 /Estimated/
- 5.2 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.
- 5.3 Hazard Declaration
- H319
- 5.3 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.
- 5.4 RIDADR
- 无资料?
- 5.4 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.
- 5.5 FirePotential
- FIRE HAZARD: Moderate, when exposed to heat or flame.
- 5.6 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.
- 5.7 Caution Statement
- P305 + P351 + P338
- 5.7 Formulations/Preparations
- /Available as/ liquid grades, assay 98%
- 5.8 WGK Germany
- 1
- 5.8 RTECS
- AK5775000
- 5.8 Protective Equipment and Clothing
- Methyl... acetoacetate may be irritating /to eyes and skin/.
- 5.9 Skin, Eye, and Respiratory Irritations
- Methyl... acetoacetate may be irritating /to eyes and skin/.
- 5.10 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)
- 5.11 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
- 5.12 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
7. Synthesis Route
105-45-3Total: 16 Synthesis Route
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Literatures:
Mitsudome, Takato; Yoshida, Syuhei; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi
Angewandte Chemie - International Edition, 2013 , vol. 52, # 23 p. 5961 - 5964
Angew. Chem., 2013 , vol. 125, # 23 p. 6077 - 6080,4
Yield: ~73%
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9. Other Information
- 9.0 Merck
- 14,6009
- 9.1 BRN
- 506727
- 9.2 Chemical Properties
- Colorless, clear liquid
- 9.3 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.
- 9.4 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.
- 9.5 Production Methods
- Methyl acetoacetate is produced by a reaction of methyl acetate with sodium methoxide.
- 9.6 General Description
- A clear colorless liquid. Flash point 158°F. Denser than water and slightly soluble in water. Vapors heavier than air.
- 9.7 Air & Water Reactions
- Very slightly soluble in water.
- 9.8 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
- 9.9 Hazard
- Toxic by ingestion and inhalation.
- 9.10 Health Hazard
- May be harmful by inhalation, ingestion, or skin absorption. Causes eye irritation. May cause skin irritation.
- 9.11 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.
- 9.12 Carcinogenicity
- Not listed by ACGIH, IARC, NTP, or California Proposition 65.
- 9.13 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.
10. Computational chemical data
- Molecular Weight: 116.11522g/mol
- Molecular Formula: C5H8O3
- Compound Is Canonicalized: True
- XLogP3-AA: 0
- Exact Mass: 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==
12. Realated Product Infomation
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