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226319

Sigma-Aldrich

Ethyl isocyanoacetate

95%

Sinonimo/i:

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

Formula condensata:
CNCH2COOCH2CH3
Numero CAS:
Peso molecolare:
113.11
Beilstein:
3588613
Numero CE:
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

95%

Forma fisica

liquid

Indice di rifrazione

n20/D 1.418 (lit.)

P. eboll.

194-196 °C (lit.)

Densità

1.035 g/mL at 25 °C (lit.)

Gruppo funzionale

amine
ester
isonitrile

Temperatura di conservazione

2-8°C

Stringa SMILE

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

InChI

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

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Descrizione generale

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

Applicazioni

Ethyl isocyanoacetate was used in the synthesis of 7-aza-tetrahydroindoles. It was also used to prepare pyrroles, oxazolines, benzodiazepines, oxazoles and imidazoles.

Pittogrammi

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Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

183.2 °F - closed cup

Punto d’infiammabilità (°C)

84 °C - closed cup

Dispositivi di protezione individuale

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


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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
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
Tetrahedron Letters, 47, 5481-5481 (2006)

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