Merck
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238880

Sigma-Aldrich

Methyl isocyanoacetate

technical grade, 95%

Linear Formula:
CNCH2COOCH3
CAS Number:
Molecular Weight:
99.09
Beilstein:
3537963
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Quality Level

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.

Packaging

1, 5 g in glass bottle

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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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