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226319

Sigma-Aldrich

Ethyl isocyanoacetate

95%

Sinónimos:

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

Fórmula lineal:
CNCH2COOCH2CH3
Número de CAS:
2999-46-4
Peso molecular:
113.11
Beilstein:
3588613
Número CE:
221-077-9
Número MDL:
MFCD00000007
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24853557
NACRES:
NA.22
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Nivel de calidad

100

Ensayo

95%

Formulario

liquid

índice de refracción

n20/D 1.418 (lit.)

bp

194-196 °C (lit.)

densidad

1.035 g/mL at 25 °C (lit.)

grupo funcional

amine
ester
isonitrile

temp. de almacenamiento

2-8°C

cadena SMILES

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

InChI

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

Clave InChI

FPULFENIJDPZBX-UHFFFAOYSA-N

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Descripción general

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

Aplicación

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].

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H302 + H332

Clasificaciones de peligro

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

183.2 °F - closed cup

Punto de inflamabilidad (°C)

84 °C - closed cup

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
STBL1708
STBJ3749
STBH6685
STBH2264
STBG8437

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Tetrahedron Letters, 47, 5481-5481 (2006)
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
Flow-assisted synthesis of heterocycles via multicomponent reactions
Van MS, et al.
Syntheses of Heterocyclic Compounds. , 133-159 (2018)
Z Q Gu et al.
Journal of medicinal chemistry, 36(8), 1001-1006 (1993-04-16)
A series of imidazo[1,5-a][1,4]benzodiazepine esters have been synthesized with varying ester side chains and 8-position substituents. The affinities of these compounds were evaluated at both "diazepam-insensitive" (DI) and diazepam-sensitive (DS) subtypes of the benzodiazepine receptor (BZR). A profound steric effect
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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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