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Methyl acetoacetate(CAS No. 105-45-3)

Methyl acetoacetate C5H8O3 (cas 105-45-3) Molecular Structure

105-45-3 Structure

Identification and Related Records

【Name】
Methyl acetoacetate
【Iupac name】
methyl 3-oxobutanoate
【CAS Registry number】
105-45-3
【Synonyms】
MAA
Methyl acetoacetaten 99%
6-Methoxy-2-(4-Methoxyphenyl)Benzothiophene
Acetoacetic acid methyl ester
Butanoic acid, 3-oxo-, methyl ester:
【EINECS(EC#)】
203-299-8
【Molecular Formula】
C5H8O3 (Products with the same molecular formula)
【Molecular Weight】
116.12
【Inchi】
InChI=1/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3
【InChIKey】
WRQNANDWMGAFTP-UHFFFAOYSA-N
【Canonical SMILES】
CC(=O)CC(=O)OC
【MOL File】
105-45-3.mol

Chemical and Physical Properties

【Appearance】
Colorless liquid.
【Density】
1.077
【Melting Point】
-80℃
【Boiling Point】
169-170℃
【Vapour】
1.54mmHg at 25°C
【Refractive Index】
1.4175-1.4295
【Flash Point】
67℃
【Water】
460 g/L (20℃)
【Solubilities】
460 g/L (20 oC)
【Color/Form】
Colorless liquid
【Stability】
Stable under normal temperatures and pressures.
【HS Code】
29183000
【Storage temp】
Store in a cool, dry place. Keep container closed when not in use.
【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)
【Computed Properties】
Molecular Weight:116.11522 [g/mol]
Molecular Formula:C5H8O3
XLogP3-AA:0
H-Bond Donor:0
H-Bond Acceptor:3
Rotatable Bond Count:3
Tautomer Count:5
Exact Mass:116.047344
MonoIsotopic Mass:116.047344
Topological Polar Surface Area:43.4
Heavy Atom Count:8
Formal Charge:0
Complexity:106
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Anion Count:1
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:12

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36
【Safety Statements 】
S26
【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)
【PackingGroup 】
Z01
【Skin, Eye, and Respiratory Irritations】
Methyl... acetoacetate may be irritating /to eyes and skin/.
【Transport】
无资料?
【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.
【Fire Potential】
FIRE HAZARD: Moderate, when exposed to heat or flame.
【Formulations/Preparations】
/Available as/ liquid grades, assay 98%
【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.
【Protective Equipment and Clothing】
Methyl... acetoacetate may be irritating /to eyes and skin/.
【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
【Octanol/Water Partition Coefficient】
log Kow = -0.69 /Estimated/
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Reaction of methyl acetate with sodium methoxide
Acetoacetic esters are generally made from diketene and the corresponding alcohol as a solvent in the presence of a catalyst. In the case of liquid alcohols, manufacturing is carried out by continuous reaction in a tubular reactor with carefully adjusted feeds of diketene, alcohol, and catalyst, or alcohol-catalyst blend followed by continuous purification. For solid alcohol, an inert solvent is used. Catalysts used include strong acids, tertiary amines, salts such as sodium acetate, organophosphorus compounds, and organometallic compounds. /Acetoacetic Esters/
U.S. Production

This chemical is listed as a High Production Volume (HPV) (65FR81686; http://www.epa.gov/opptintr/chemrtk/hpvchmlt.htm). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438; http://www.epa.gov/oppt/iur/index.htm).
(1972) PROBABLY GREATER THAN 9.08X10+5 GRAMS
(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS
【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.

Biomedical Effects and Toxicity

【Pharmacological Action】
May be harmful by inhalation, ingestion, or skin absorption. Causes eye irritation. May cause skin irritation.
【Therapeutic 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.
【Biomedical Effects and Toxicity】
Like other esters, /methyl acetoacetate/ is potentially skin-absorbable.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
The rate constant for the vapor-phase reaction of methyl acetoacetate with photochemically-produced hydroxyl radicals has been reported as 3.25X10-13 cu cm/molecule-sec at 25 deg C(1). This corresponds to an atmospheric half-life of about 5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 0.57 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 140 and 14 days at pH values of 7 and 8, respectively(3). Methyl acetoacetate is not expected to be susceptible to direct photolysis by sunlight(SRC), since it does not absorb light with wavelengths >290 nm(4).

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