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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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25 G
$63.27
500 G
$152.00
1 KG
$232.00

About This Item

Linear Formula:
NCCH2COOH
CAS Number:
372-09-8
Molecular Weight:
85.06
Beilstein/REAXYS Number:
506325
EC Number:
206-743-9
MDL number:
MFCD00002677
UNSPSC Code:
12352100
PubChem Substance ID:
24893110
NACRES:
NA.22

$63.27

List Price$70.30Save 10%
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Available to ship onMay 01, 2025Details

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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

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH031

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

224.6 °F - closed cup

flash_point_c

107 °C - closed cup

ppe

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

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Certificates of Analysis (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)
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
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
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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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