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2999-46-4 molecular structure
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ethyl 2-isocyanoacetate

ChemBase ID: 78318
Molecular Formular: C5H7NO2
Molecular Mass: 113.11458
Monoisotopic Mass: 113.04767847
SMILES and InChIs

SMILES:
[N+](#[C-])CC(=O)OCC
Canonical SMILES:
[C-]#[N+]CC(=O)OCC
InChI:
InChI=1S/C5H7NO2/c1-3-8-5(7)4-6-2/h3-4H2,1H3
InChIKey:
FPULFENIJDPZBX-UHFFFAOYSA-N

Cite this record

CBID:78318 http://www.chembase.cn/molecule-78318.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
ethyl 2-isocyanoacetate
IUPAC Traditional name
ethyl 2-isocyanoacetate
Synonyms
Ethyl isocyanoacetate
ethyl 2-isocyanoacetate
Isocyanoacetic acid ethyl ester
Ethyl isocyanoacetate
异氰基乙酸乙酯
异氰乙酸乙酯
CAS Number
2999-46-4
EC Number
221-077-9
MDL Number
MFCD00000007
Beilstein Number
3588613
PubChem SID
162043087
24881207
24853557
PubChem CID
533707

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 16.10355  H Acceptors
H Donor LogD (pH = 5.5) -1.9777237 
LogD (pH = 7.4) -1.9777237  Log P -1.9777237 
Molar Refractivity 37.1139 cm3 Polarizability 11.067871 Å3
Polar Surface Area 30.66 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Boiling Point
194-196 °C(lit.) expand Show data source
194-196°C expand Show data source
194-196°C expand Show data source
Flash Point
183.2 °F expand Show data source
84 °C expand Show data source
84°C expand Show data source
84°C(183°F) expand Show data source
Density
1.035 expand Show data source
1.035 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
1.4220 expand Show data source
n20/D 1.418 expand Show data source
n20/D 1.418(lit.) expand Show data source
Hydrophobicity(logP)
-0.067 expand Show data source
Storage Warning
Moisture & Light Sensitive expand Show data source
Toxic/Moisture Sensitive/Light Sensitive/Store under Argon/Keep Cold expand Show data source
European Hazard Symbols
X expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
2810 expand Show data source
UN2810 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
6.1 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Risk Statements
20/21/22-36/37/38 expand Show data source
20/22 expand Show data source
Safety Statements
9-26-36/37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H332 expand Show data source
H331-H302-H312-H315-H319-H335-H227 expand Show data source
GHS Precautionary statements
P210-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 2810 6.1/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98.0% (GC) expand Show data source
95% expand Show data source
98% expand Show data source
Grade
purum expand Show data source
Linear Formula
CNCH2COOCH2CH3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 226319 external link
Application
Cyclization synthon used to prepare pyrroles,1,2 oxazolines,3 benzodiazepines,4 oxazoles5 and imidazoles.6
General description
Material may darken upon storage
Packaging
5, 25 g in glass bottle
Sigma Aldrich - 58822 external link
Caution
discolors to brown on storage
Other Notes
Reviews1,2; Synthesis of α-amino acids3

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • The method has been extended to nitroaromatics, leading to pyrroles and porphyrins fused with aromatic rings: J. Chem. Soc., Perkin 1, 417 (1996).
  • • Base-catalyzed Michael addition to nitroalkenes provides a route to substituted pyrroles, valuable as intermediates for porphyrin synthesis: J. Chem. Soc., Chem. Commun., 1098 (1985); Tetrahedron, 46, 7483, 7587 (1990); Org. Synth. Coll., 9, 242 (1998).
  • • The terminal carbon also undergoes nucleophilic attack on an acyl chloride to give an ɑ-keto imidoyl chloride, which cyclizes in base to a 2-acyl-5-ethoxy oxazole: Synth. Commun., 26, 1149 (1996).
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PATENTS

PATENTS

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INTERNET

INTERNET

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