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C88505

Sigma-Aldrich

Cyanoacetic acid

99%

Synonym(s):

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

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About This Item

Linear Formula:
NCCH2COOH
CAS Number:
372-09-8
Molecular Weight:
85.06
Beilstein:
506325
EC Number:
206-743-9
MDL number:
MFCD00002677
UNSPSC Code:
12352100
PubChem Substance ID:
24893110
NACRES:
NA.22
Pricing and availability is not currently available.

vapor pressure

0.1 mmHg ( 100 °C)

Quality Level

100

Assay

99%

form

crystals

bp

108 °C/0.15 mmHg (lit.)

mp

64-70 °C (lit.)

solubility

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

SMILES string

OC(=O)CC#N

InChI

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

InChI key

MLIREBYILWEBDM-UHFFFAOYSA-N

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Application

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]

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H332,H314

Hazard Classifications

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

Supplementary Hazards

EUH031

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

224.6 °F - closed cup

Flash Point(C)

107 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX2849
MKCT6916
MKCS4798
MKCS4797
MKCR6404

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Synthesis of novel ??3 receptor ligands via an unusual Knoevenagel condensation
Volkova MS, et al.
Bioorganic & medicinal chemistry letters, 22(24), 7578-7581 (2012)
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)
Yijun Huang et al.
Molecular diversity, 15(1), 3-33 (2010-03-02)
The Gewald reaction of sulfur, cyanoacetic acid derivatives, and oxo-component (G-3CR) yielding highly substituted 2-aminothiophene derivatives has seen diverse applications in combinatorial and medicinal chemistry. Its products are of great use in pharmaceutical industry mainly as small molecular weight inhibitors.
B S Kim et al.
Neuroradiology, 45(7), 445-450 (2003-06-05)
Congenital arteriovenous fistulae (AVF) of the internal maxillary artery (IMA) are rare. We present the angiographic findings and management of six AVF of the IMA, selected from 147 patients with facial vascular malformations. The fistula was thought to be congenital
S Kotha et al.
Amino acids, 32(3), 387-394 (2006-10-13)
Two synthetic routes to bis-armed-alpha-amino acid derivatives are described. The first route involves alkylation of dibromo derivatives with ethyl isocyanoacetate under phase-transfer catalysis (PTC) conditions. The second route uses a palladium-mediated Suzuki-Miyaura cross-coupling reaction between a DL-4-boronophenylalanine derivative and aromatic
View All Related Papers

Questions

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  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

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  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

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