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E1505

Sigma-Aldrich

Ethyl 2-cyanoacrylate

liquid

Synonym(s):

ethyl 2-cyanoprop-2-enoate

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About This Item

Empirical Formula (Hill Notation):
C6H7NO2
CAS Number:
Molecular Weight:
125.13
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23
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form

liquid

storage temp.

2-8°C

SMILES string

CCOC(=O)C(=C)C#N

InChI

1S/C6H7NO2/c1-3-9-6(8)5(2)4-7/h2-3H2,1H3

InChI key

FGBJXOREULPLGL-UHFFFAOYSA-N

General description

Ethyl 2-cyanoacrylate belongs to the class of monomers known as cyanoacrylates. Ethyl 2-cyanoacrylate polymers are primarily used as adhesives due to their fast-setting and strong bonding properties. They are widely utilized for bonding a variety of materials, including metals, plastics, rubber, ceramics, and wood. These adhesives are used in industries such as automotive, electronics, crafts, and general repairs. Ethyl 2-cyanoacrylate adhesives find applications in industrial and manufacturing processes. They are used for sealing products, encapsulating electronics, and securing parts during assembly.[1][2]

Application

Ethyl 2-cyanoacrylate, commonly known as super glue, has several uses in the field of bioadhesives:
  • Wound Closure: Ethyl 2-cyanoacrylate is often used in medical settings to close small cuts and wounds. It forms a strong bond when it comes into contact with moisture, effectively sealing the wound.
  • Tissue Adhesives: In surgical and medical applications, ethyl 2-cyanoacrylate is used to adhere tissues together. It can be used as an alternative to traditional sutures or staples in certain procedures.
  • Drug Delivery Systems: In some cases, ethyl 2-cyanoacrylate has been investigated as a component in drug delivery systems and tissue engineering due to its biocompatibility and ability to form strong bonds with biological materials.
  • It can also be mixed with hydrophobic silica nanoparticles for the designing of cotton fabrics for medical applications.[3]

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

185.0 °F - closed cup

Flash Point(C)

85 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Ana Isabel Quilez-Molina et al.
Polymers, 12(9) (2020-09-10)
Applications of cyanoacrylate monomers are generally limited to adhesives/glues (instant or superglues) and forensic sciences. They tend to polymerize rapidly into rigid structures when exposed to trace amounts of moisture. Transforming cyanoacrylate monomers into transparent polymeric films or coatings can
Willian Morais De Melo et al.
Journal of oral and maxillofacial surgery : official journal of the American Association of Oral and Maxillofacial Surgeons, 71(1), 35-41 (2012-10-30)
Cyanoacrylate has been used as a commercial tissue adhesive. Recently, ethyl 2-cyanoacrylate has been suggested for the fixation of onlay autogenous bone graft. However, ethyl 2-cyanoacrylate must be biocompatible with bone tissue. This study evaluated the cytotoxicity of cyanoacrylate adhesives
A McDowell et al.
New Zealand veterinary journal, 57(6), 370-377 (2009-12-08)
To investigate polymeric nanoparticles as an oral delivery system for protein biocontrol agents for control of the brushtail possum, Trichosurus vulpecula. Insulin-loaded poly(ethyl 2-cyanoacrylate) (PECA) nanoparticles were prepared using interfacial polymerisation, and characterised for size, zeta potential, and efficiency of
Qiwen Chen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(44), 12458-12464 (2011-09-20)
A carbon nanotube/poly(ethyl 2-cyanoacrylate) (CNT/PECA) composite electrode was developed for enhanced amperometric detection. The composite electrode was fabricated on the basis of water-vapor-initiated polymerization of a mixture of CNTs and ethyl 2-cyanoacrylate in the bore of a piece of fused
Histopathological effects of ethyl 2-cyanoacrylate tissue adhesive following surgical application: an experimental study
Kaplan M, et al.
European Journal of Cardio-Thoracic Surgery : Official Journal of the European Association For Cardio-Thoracic Surgery, 25(2), 167-172 (2004)

Questions

1–2 of 2 Questions  
  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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