Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

226319

Sigma-Aldrich

Ethyl isocyanoacetate

95%

Synonym(s):

α-Isocyanoacetic acid ethyl ester, (Ethoxycarbonyl)methyl isonitrile, 2-Ethoxy-2-oxoethyl isocyanide, 2-Ethyloxycarbonylmethyl isocyanide, Ethoxycarbonylmethyl isocyanide, Ethyl α-isocyanoacetate, Ethyl 2-isocyanoacetate, Isocyanoacetic acid ethyl ester

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

About This Item

Linear Formula:
CNCH2COOCH2CH3
CAS Number:
2999-46-4
Molecular Weight:
113.11
Beilstein:
3588613
EC Number:
221-077-9
MDL number:
MFCD00000007
UNSPSC Code:
12352100
PubChem Substance ID:
24853557
NACRES:
NA.22
Pricing and availability is not currently available.

Assay

95%

form

liquid

refractive index

n20/D 1.418 (lit.)

bp

194-196 °C (lit.)

density

1.035 g/mL at 25 °C (lit.)

functional group

amine
ester
isonitrile

storage temp.

2-8°C

SMILES string

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

InChI

1S/C5H7NO2/c1-3-8-5(7)4-6-2/h3-4H2,1H3

InChI key

FPULFENIJDPZBX-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Ethyl isocyanoacetate is an isocyanide ester that serves as a building block for the production of heterocycles.[1]

Application

Ethyl isocyanoacetate was used in the synthesis of 7-aza-tetrahydroindoles[2]. It was also used to prepare pyrroles[3][4], oxazolines[5], benzodiazepines[6], oxazoles[7] and imidazoles[8].

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H332

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

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
STBL1708
STBJ3749
STBH6685
STBH2264
STBG8437

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, 34, 5463-5463 (1993)
Marcus Baumann et al.
Organic letters, 8(23), 5231-5234 (2006-11-03)
[Structure: see text] A multipurpose mesofluidic flow reactor capable of producing gram quantities of material has been developed as an automated synthesis platform for the rapid on-demand synthesis of key building blocks and small exploratory libraries. The reactor is configured
Yifei Li et al.
Chemical communications (Cambridge, England), 48(100), 12228-12230 (2012-11-13)
A novel and efficient route for the synthesis of 7-aza-tetrahydroindoles from N-aryl/alkyl-alkenoylacetamides and ethyl isocyanoacetate is described. A mechanism, involving a stepwise [3+2] cycloaddition-intramolecular aza-Michael addition cascade, is proposed that explains the origin of the double nucleophilic attack on the
Chikashi Kanazawa et al.
Journal of the American Chemical Society, 128(33), 10662-10663 (2006-08-17)
The copper-catalyzed reaction between two different isocyanides produces the corresponding heteroaromatization products, imidazoles, in good yields. The reaction proceeds most probably through the activation of the sp3 C-H bond in the isocyanides by a copper catalyst, followed by a [3
Tetrahedron Letters, 35, 2493-2493 (1994)
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

Reviews

No rating value

Active Filters

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