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10227-18-6 molecular structure
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1,4-dimethyl but-2-ynedioate

ChemBase ID: 78495
Molecular Formular: C6H6O4
Molecular Mass: 142.10944
Monoisotopic Mass: 142.02660867
SMILES and InChIs

SMILES:
O(C(=O)C#CC(=O)OC)C
Canonical SMILES:
COC(=O)C#CC(=O)OC
InChI:
InChI=1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
InChIKey:
VHILMKFSCRWWIJ-UHFFFAOYSA-N

Cite this record

CBID:78495 http://www.chembase.cn/molecule-78495.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,4-dimethyl but-2-ynedioate
IUPAC Traditional name
1,4-dimethyl but-2-ynedioate
Synonyms
Dimethyl 2-butynedioate
Dimethyl acetylenedicarboxylate
DMAD
Acetylenedicarboxylic
acid dimethyl ester
Dimethyl acetylenedicarboxylate
Acetylenedicarboxylic acid dimethyl ester
Butynedioic acid dimethyl ester
Dimethyl acetylenedicarboxylate
Dimethyl but-2-yne-1,4-dioate
dimethyl but-2-ynedioate
丁炔二酸二甲酯
CAS Number
10227-18-6
762-42-5
EC Number
212-098-4
MDL Number
MFCD00008456
Beilstein Number
607063
PubChem SID
24893421
162043261
24845139
PubChem CID
12980
Chemspider ID
12440
Wikipedia Title
Dimethyl_acetylenedicarboxylate

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 0.9685472  LogD (pH = 7.4) 0.9685472 
Log P 0.9685472  Molar Refractivity 32.5402 cm3
Polarizability 12.367345 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
Insoluble in water expand Show data source
Soluble in most
organic solvents
expand Show data source
Apperance
Colorless liquid expand Show data source
Melting Point
-18 - -16°C expand Show data source
-18°C expand Show data source
-18°C expand Show data source
c expand Show data source
Boiling Point
195–198 °C
96–98° at 8 mm Hg
expand Show data source
195-198°C expand Show data source
95-98 °C/19 mmHg(lit.) expand Show data source
95-98°C/19mm expand Show data source
Flash Point
186.8 °F expand Show data source
187 °F expand Show data source
86 °C expand Show data source
86°C expand Show data source
86°C(186°F) expand Show data source
Density
1.156 expand Show data source
1.156 g/mL at 25 °C(lit.) expand Show data source
1.1564 g/cm3 expand Show data source
Refractive Index
1.447 expand Show data source
1.4470 expand Show data source
1.4480 expand Show data source
n20/D 1.447 expand Show data source
n20/D 1.447(lit.) expand Show data source
Hydrophobicity(logP)
-0.09 expand Show data source
Storage Warning
Corrosive/Harmful/Air Sensitive/Light Sensitive/Lachrymatory/Keep Cold/Store under Argon expand Show data source
Light Sensitive expand Show data source
RTECS
ES0175000 expand Show data source
European Hazard Symbols
Corrosive Corrosive (C) expand Show data source
X expand Show data source
UN Number
3265 expand Show data source
UN1760 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
8 expand Show data source
Packing Group
2 expand Show data source
II expand Show data source
Risk Statements
21/22-34 expand Show data source
34 expand Show data source
R34 expand Show data source
Safety Statements
23-26-27-36/37/39-45 expand Show data source
26-36/37/39-45 expand Show data source
S23 S26 S27
S36/37/39 S45
expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Danger expand Show data source
Main Hazard
Toxic gas expand Show data source
GHS Hazard statements
H302-H314 expand Show data source
H314-H318-H302-H227 expand Show data source
GHS Precautionary statements
P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A expand Show data source
P280-P305 + P351 + P338-P310 expand Show data source
Personal Protective Equipment
Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 3265 8/PG 2 expand Show data source
Purity
≥96.0% (GC) expand Show data source
95% expand Show data source
97% expand Show data source
98% expand Show data source
99% expand Show data source
Grade
purum expand Show data source
Linear Formula
CH3OCOC≡CCO2CH3 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - D138401 external link
Packaging
5, 25 g in glass bottle
Application
Versatile dienophile used in Diels-Alder reactions.1,2,3

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Dienophile in Diels-Alder and related reactions. For addition to a bis-allene, followed by dimerization to a paracyclophane, see: Org. Synth. Coll., 7, 485 (1990).
  • • For use in the masking of double bonds for subsequent release by cycloreversion, see: J. Org. Chem., 44, 962 (1979). Review of cycloreversion reactions in organic synthesis: Synthesis, 121 (1985).
  • • Used in synthesis of a wide variety of heterocyclic systems including benzo[b]thiophenes from thiophenols: Acta Chem. Scand.,27, 595 (1973), and chromones from phenols: Austral. J. Chem., 48, 677 (1995):
  • • Stabilized anions derived from cyclic ?-keto phosphonates undergo ring expansion, via a tandem Michael-Aldol-fragmentation mechanism, to give phosphonates with an additional two carbons in the ring, thus providing a route to highly functionalized medium ring compounds: J. Org. Chem., 60, 3084 (1995):
  • • Reacts with activated carbonyl compounds, such as ɑ-keto esters or ɑ-keto nitriles, in the presence of triphenylphosphine, to give highly functionalized -butyrolactones: J. Org. Chem., 61, 4516 (1996). For a further example with reaction scheme, see 2,2,2-Trifluoroacetophenone, A11403.
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PATENTS

PATENTS

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INTERNET

INTERNET

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