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C88505

Sigma-Aldrich

Cyanoacetic acid

99%

Sinónimos:

2-Cyanoacetic acid, Cyanoethanoic acid, Malonic mononitrile, Monocyanoacetic acid

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About This Item

Fórmula lineal:
NCCH2COOH
Número de CAS:
372-09-8
Peso molecular:
85.06
Beilstein:
506325
Número CE:
206-743-9
Número MDL:
MFCD00002677
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24893110
NACRES:
NA.22
En este momento no podemos mostrarle ni los precios ni la disponibilidad

presión de vapor

0.1 mmHg ( 100 °C)

Nivel de calidad

100

Ensayo

99%

Formulario

crystals

bp

108 °C/0.15 mmHg (lit.)

mp

64-70 °C (lit.)

solubilidad

H2O: 50 mg/mL, clear, colorless to very faintly yellow

cadena SMILES

OC(=O)CC#N

InChI

1S/C3H3NO2/c4-2-1-3(5)6/h1H2,(H,5,6)

Clave InChI

MLIREBYILWEBDM-UHFFFAOYSA-N

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Aplicación

Cyanoacetic acid can be used as a reagent:
  • Along with acetic anhydride for cyanoacetylation of various pyrroles, indoles, and aniline derivatives. It can also be used in other reactions such as cyclizations, syntheses of coumarins and other heterocycles.[1]
  • To prepare of key intermediate via Knoevenagel condensation in the total synthesis of 5-acetamido-substituted melatonin derivatives as MT3 receptor ligands.[2]
  • In the synthesis of aminopyrrolinone derivatives by reacting Ugi adducts of cyanoacetic acid and aromatic aldehydes.[3]

Pictogramas

CorrosionExclamation mark
GHS05,GHS07

Palabra de señalización

Danger

Frases de peligro

H302 + H332,H314

Clasificaciones de peligro

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Riesgos supl.

EUH031

Código de clase de almacenamiento

8A - Combustible corrosive hazardous materials

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

224.6 °F - closed cup

Punto de inflamabilidad (°C)

107 °C - closed cup

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
MKCX2849
MKCT6916
MKCS4798
MKCS4797
MKCR6404

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Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride
Slaett J, et al.
Synthesis, 2004(16), 2760-2765 (2004)
Synthesis of novel ??3 receptor ligands via an unusual Knoevenagel condensation
Volkova MS, et al.
Bioorganic & medicinal chemistry letters, 22(24), 7578-7581 (2012)
The Ugi Reaction of Cyanoacetic Acid as a Route to Tetramic Acid Derivatives
Alvarez-Rodriguez NV, et al.
Synlett, 26(16), 2253-2256 (2015)
Kan Wang et al.
Chemical biology & drug design, 75(3), 277-283 (2010-07-28)
The design of an unprecedented multicomponent reaction to and synthesis of 2-amino-5-ketoaryl pyrroles are described. The compounds (14 examples) can be synthesized by reacting aminoacetophenone sulfonamides, (hetero)aromatic aldehydes, and malonodinitrile or cyanoacetic acid derivatives in one-pot manner. Pharmacophore features and
Julien Warnan et al.
Macromolecular rapid communications, 32(15), 1190-1194 (2011-06-29)
A series of three poly(3-hexylthiophene) functionalized either with a cyanoacetic acid (CA) or a rhodanine-3-acetic acid anchoring groups were synthesized and characterized. The TiO(2) based dye-sensitized solar cells have been fabricated and performances were tested. We show that shorter chain
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Questions

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  1. 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

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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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