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226319

Sigma-Aldrich

Ethyl isocyanoacetate

95%

Synonyme(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

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About This Item

Formule linéaire :
CNCH2COOCH2CH3
Numéro CAS:
2999-46-4
Poids moléculaire :
113.11
Beilstein:
3588613
Numéro CE :
221-077-9
Numéro MDL:
MFCD00000007
Code UNSPSC :
12352100
ID de substance PubChem :
24853557
Nomenclature NACRES :
NA.22

113.00 CHF

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Devis pour commande en gros

Essai

95%

Forme

liquid

Indice de réfraction

n20/D 1.418 (lit.)

pb

194-196 °C (lit.)

Densité

1.035 g/mL at 25 °C (lit.)

Groupe fonctionnel

amine
ester
isonitrile

Température de stockage

2-8°C

Chaîne SMILES 

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

InChI

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

Clé InChI

FPULFENIJDPZBX-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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].

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302 + H332

Classification des risques

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

183.2 °F - closed cup

Point d'éclair (°C)

84 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificats d'analyse (COA)

Lot/Batch Number
STBL1708
STBJ3749
STBH6685
STBH2264
STBG8437

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Consulter la Bibliothèque de documents

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
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
Tetrahedron Letters, 35, 2493-2493 (1994)
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
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  1. How can I determine the shelf life / expiration / retest date of this product?

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    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

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  2. 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

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