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Sigma-Aldrich

Methyl isocyanoacetate

technical grade, 95%

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Linear Formula:
CNCH2COOCH3
CAS Number:
39687-95-1
Molecular Weight:
99.09
Beilstein:
3537963
EC Number:
254-593-8
MDL number:
MFCD00000006
PubChem Substance ID:
24854350
NACRES:
NA.22

grade

technical grade

Quality Level

100

Assay

95%

form

liquid

refractive index

n20/D 1.417 (lit.)

bp

75-76 °C/10 mmHg (lit.)

density

1.09 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

COC(=O)C[N+]#[C-]

InChI

1S/C4H5NO2/c1-5-3-4(6)7-2/h3H2,2H3

InChI key

CRXFROMHHBMNAB-UHFFFAOYSA-N

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General description

Methyl isocyanoacetate undergoes direct aldol reaction with carbonyl compounds in the presence of solid-phase catechol-copper network catalyst to yield corresponding oxazolines. It also participates in four-component Ugi condensation reaction.

Application

Methyl isocyanoacetate has been used in the copper-catalyzed, diastereoselective synthesis of oxazolines.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H312 + H332 - H314

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

183.2 °F - closed cup

Flash Point(C)

84 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Hidetoshi Ohta et al.
Chemistry, an Asian journal, 6(9), 2545-2549 (2011-07-14)
The development of a highly active solid-phase catechol-copper network catalyst for direct aldol reaction is described. The catalyst was prepared from an alkyl-chain-linked bis(catechol) and a copper(II) complex. The direct aldol reaction between carbonyl compounds (aldehydes and ketones) and methyl
Tetrahedron Letters, 47, 8641-8641 (2006)
X C Liu et al.
Biotechnology and bioengineering, 69(4), 457-460 (2000-06-22)
The chemoenzymatic preparation of a nine-member Ugi condensation library is described. The carboxylic acid and amine precursors are based on 3-hydroxybutyrate and 4-amino-1-butanol, respectively, and have been acylated selectively using a variety of acyl donors catalyzed by porcine pancreatic lipase.
Stefan Oelmann et al.
Biomacromolecules, 20(1), 90-101 (2018-06-06)
A Passerini three-component polymerization was performed for the synthesis of amphiphilic star-shaped block copolymers with hydrophobic cores and hydrophilic coronae. The degree of polymerization of the hydrophobic core was varied from 5 to 10 repeating units, and the side chain

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