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MilliporeSigma

108421

Methyl cyanoacetate

99%

Synonym(s):

Methyl 2-cyanoacetate

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25 G

$63.10

500 G

$107.00

$63.10


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About This Item

Linear Formula:
NCCH2COOCH3
CAS Number:
Molecular Weight:
99.09
NACRES:
NA.22
PubChem Substance ID:
eCl@ss:
39031513
UNSPSC Code:
12352100
EC Number:
203-288-8
MDL number:
Beilstein/REAXYS Number:
773945
Assay:
99%

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InChI key

ANGDWNBGPBMQHW-UHFFFAOYSA-N

InChI

1S/C4H5NO2/c1-7-4(6)2-3-5/h2H2,1H3

SMILES string

COC(=O)CC#N

vapor density

3.41 (vs air)

vapor pressure

0.2 mmHg ( 20 °C)

assay

99%

refractive index

n20/D 1.417 (lit.)

bp

204-207 °C (lit.)

mp

−13 °C (lit.)

density

1.123 g/mL at 25 °C (lit.)

functional group

ester, nitrile

Quality Level

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1 of 4

This Item
233412E1842528440
assay

99%

assay

97%

assay

≥98%

assay

≥97.0% (GC)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

bp

204-207 °C (lit.)

bp

-

bp

208-210 °C (lit.)

bp

40-42 °C/0.1 mmHg (lit.)

refractive index

n20/D 1.417 (lit.)

refractive index

-

refractive index

n20/D 1.418 (lit.)

refractive index

n20/D 1.420

density

1.123 g/mL at 25 °C (lit.)

density

-

density

1.063 g/mL at 25 °C (lit.)

density

0.988 g/mL at 20 °C (lit.)

mp

−13 °C (lit.)

mp

130-132 °C (lit.)

mp

−22 °C (lit.)

mp

-

General description

Methyl cyanoacetate is the intermediate product in pharmaceutical organic synthesis as well as in the synthesis of some biologically active compounds used in agriculture[1]. It undergoes calcite or fluorite catalyzed Knövenagel condensation with aromatic aldehydes, giving the corresponding arylidenemalononitriles and (E)-α-cyanocinnamic esters[2].

Application

Methyl cyanoacetate may be used in the synthesis of various 1,2,5-tricarbonyl compounds[3].

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves


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Construction of 1, 2, 5-Tricarbonyl Compounds using Methyl Cyanoacetate as a Glyoxylate Anion Synthon Combined with Copper (I) Iodide-Catalyzed Aerobic Oxidation.
Kim SH, et al.
Advanced Synthesis & Catalysis, 353(18), 3335-3339 (2011)
Conformational isomerism in methyl cyanoacetate: A combined matrix-isolation infrared spectroscopy and molecular orbital study.
Reva ID, et al
Physical Chemistry Chemical Physics, 3(19), 4235-4241 (2011)
Calcite and fluorite as catalyst for the Knovenagel condensation of malononitrile and methyl cyanoacetate under solvent-free conditions.
Wada S and Suzuki H.
Tetrahedron Letters, 44(2), 399-401 (2003)
Søren S Donau et al.
Chemosphere, 233, 873-878 (2019-07-26)
The cyanoacrylate ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (phenamacril), has been introduced as an effective agent against several fungi species belonging to the Fusarium genus. However, in current literature, knowledge about the environmental behavior of this fungicide is limited and there are no data
Yulia Kaluzhny et al.
Alternatives to laboratory animals : ATLA, 43(2), 101-127 (2015-05-23)
The 7th Amendment to the EU Cosmetics Directive and the EU REACH Regulation have reinforced the need for in vitro ocular test methods. Validated in vitro ocular toxicity tests that can predict the human response to chemicals, cosmetics and other

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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/418/501/product-dating-information-06-25-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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