Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

238880

Sigma-Aldrich

Methyl isocyanoacetate

technical grade, 95%

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
CNCH2COOCH3
CAS Number:
39687-95-1
Molecular Weight:
99.09
Beilstein:
3537963
EC Number:
254-593-8
MDL number:
MFCD00000006
UNSPSC Code:
12352100
PubChem Substance ID:
24854350
NACRES:
NA.22

grade

technical grade

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.)

functional group

amine

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCP3970
MKCG4152
MKBV8507V
MKBN4031V
SHBB8122V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Tetrahedron Letters, 47, 8641-8641 (2006)
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service