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108-59-8 molecular structure
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1,3-dimethyl propanedioate

ChemBase ID: 85346
Molecular Formular: C5H8O4
Molecular Mass: 132.11462
Monoisotopic Mass: 132.04225874
SMILES and InChIs

SMILES:
O(C(=O)CC(=O)OC)C
Canonical SMILES:
COC(=O)CC(=O)OC
InChI:
InChI=1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3
InChIKey:
BEPAFCGSDWSTEL-UHFFFAOYSA-N

Cite this record

CBID:85346 http://www.chembase.cn/molecule-85346.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,3-dimethyl propanedioate
IUPAC Traditional name
dimethyl malonate
Synonyms
Malonic acid dimethyl ester
Dimethyl malonate
Propanedioic acid dimethyl ester
Dimethyl malonate
丙二酸二甲酯
CAS Number
108-59-8
EC Number
203-597-8
MDL Number
MFCD00008460
Beilstein Number
774261
Merck Index
146096
PubChem SID
24848281
24882580
162072462
24854457
PubChem CID
7943
Chemspider ID
21106102
Wikipedia Title
Dimethyl_malonate

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.90322  H Acceptors
H Donor LogD (pH = 5.5) -0.039329175 
LogD (pH = 7.4) -0.03933052  Log P -0.039329156 
Molar Refractivity 28.526 cm3 Polarizability 11.623122 Å3
Polar Surface Area 52.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Slightly soluble in water expand Show data source
Apperance
Colorless liquid expand Show data source
Melting Point
-62 - -60°C expand Show data source
-62 °C(lit.) expand Show data source
-62°C expand Show data source
-62°C expand Show data source
Boiling Point
180-181 °C(lit.) expand Show data source
180-181°C expand Show data source
180–181 °C expand Show data source
180-181°C expand Show data source
Flash Point
185 °F expand Show data source
85 °C expand Show data source
85°C expand Show data source
90°C(194°F) expand Show data source
Density
1.154 expand Show data source
1.156 expand Show data source
1.156 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
1.4130 expand Show data source
n20/D 1.413 expand Show data source
n20/D 1.413(lit.) expand Show data source
Vapor Density
>1 (vs air) expand Show data source
Hydrophobicity(logP)
0.069 expand Show data source
Storage Warning
Irritant expand Show data source
RTECS
OO0950000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
15 expand Show data source
26-36 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H227 expand Show data source
H315-H319-H335 expand Show data source
GHS Precautionary statements
P210-P280-P370+P378A-P403+P235-P501A expand Show data source
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
Purity
≥96.0% (GC) expand Show data source
≥99% expand Show data source
95% expand Show data source
98% expand Show data source
98+% expand Show data source
Grade
purum expand Show data source
Linear Formula
CH2(COOCH3)2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia
Sigma Aldrich - 136441 external link
Packaging
1 kg in glass bottle
250 g in glass bottle

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • For successive C-alkylation, using NaOMe/MeOH, followed by NaH/THF, see: Org. Synth. Coll., 8, 381 (1993). For Michael addition to ɑ?-unsaturated acids, catalyzed by the Li salt of L-proline, see: J. Chem. Soc., Chem. Commun., 1088 (1991). For Knoevenagel reaction with (R)-citronellal, catalyzed by piperidine/AcOH, to give the alkylidene derivative, see: Org. Synth. Coll., 9, 310 (1998).
  • • C-Arylation with ortho-nitroaryl halides can be accomplished with NaH in DMSO. The products can be readily converted to substituted oxindoles: Synthesis, 51 (1993):
  • • Arylation with benzene: Tetrahedron Lett., 27, 2763 (1986), and free-radical substitution with thiophene or furan at the 2-position: Heterocycles, 27, 2627 (1988), are promoted by Ce(IV) salts.
  • • See also Diethyl malonate, A15468.
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PATENTS

PATENTS

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INTERNET

INTERNET

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