10258-54-5

Usage

Uses

Used in Chemical Synthesis Industry:
2-Methoxyethyl cyanoacetate is used as an intermediate for numerous organic syntheses, particularly in the production of alpha-cyanoacrylic adhesives. Its chemical properties allow it to serve as a key component in the synthesis of various compounds, contributing to the development of new products and materials.
Used in Adhesive Production:
In the adhesive industry, 2-Methoxyethyl cyanoacetate plays a crucial role as an intermediate in the production of alpha-cyanoacrylic adhesives. These adhesives are known for their strong bonding capabilities and quick curing times, making them ideal for various applications, such as manufacturing, construction, and consumer products.

InChI:InChI=1/C6H9NO3/c1-9-4-5-10-6(8)2-3-7/h2,4-5H2,1H3

Upstream product

• 109-86-4 2-methoxy-ethanol 
• 372-09-8 cyanoacetic acid 
• 13361-36-9 2-methoxyethyl 2-chloroacetate 
• 151-50-8 potassium cyanide 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 27816-23-5 2-methoxyethyl 2-cyanoacrylate 
• 40674-31-5 {(E)-4-[Bis-(2-chloro-ethyl)-amino]-phenylimino}-cyano-acetic acid 2-methoxy-ethyl ester 
• 105-34-0 methyl 2-cyanoacetate 
• 109-86-4 2-methoxy-ethanol 
• 13361-30-3 isopropyl cyanoacetate 
• 15725-46-9 (E)-ethyl 2-cyano-3-(2,6-dichlorophenyl)acrylate 
• 120068-79-3 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole 
• 352663-32-2 C₂₁H₂₂N₂O₉ 
• 313381-77-0 C₂₅H₂₄N₂O₇ 
• 1202935-23-6 C₂₁H₃₁N₂O₈PS 
• 1202935-45-2 C₂₃H₃₄FN₂O₈PS 
• 1202935-37-2 C₂₃H₃₅N₂O₈PS 
• 1202935-30-5 C₂₁H₃₀FN₂O₈PS 

Relevant academic research and scientific papers

Synthesis and Herbicidal Activity of 2-Cyano-3-(2-chlorothiazol-5-yl)methylaminoacrylates

A series of 2-cyano-3-(2-chlorothiazol-5-yl)methylaminoacrylates were synthesized as herbicidal inhibitors of PSII electron transport. All of these compounds exhibited good herbicidal activities. In particular, (Z)-ethoxyethyl 2-cyano-3-isopropyl-3-(2-chlorothiazol-5-yl)methylaminoacrylate showed excellent herbicidal activities even at a dose of 75 g/ha. A suitable group at the 3-position of acrylate was essential for high herbicidal activity. 2-Cyanoacrylates containing a 2-chloro-5-thiazolyl group are a novel class of herbicides and display herbicidal activities comparable to existing analogues bearing chloropyridyl or chlorophenyl.

Structure-Property Relationships of Polyethylene Glycol Modified Fluorophore as Near-Infrared Aβ Imaging Probes

To optimize the lipophilicity and improve in vivo pharmacokinetics of near-infrared probes targeted Aβ plaques, we designed, synthesized, and evaluated a series of polyethylene glycol modified probes with hydroxyl and methoxyl terminals. The relationships between chemical structure and optical, biological properties were systemically elucidated. The results indicated that a desired Aβ probe should keep a balance among molecular rigidity, size, and lipophilicity. Probe 12d displayed improved properties including intense and selective response to Aβ1-42 aggregates (Kd = 7.3 nM, 22-fold fluorescence enhancement and emission maxima at 715 nm upon interaction with Aβ1-42 aggregates), sufficient blood-brain barrier penetration (3.04% ID/g), and fast wash out from the brain (brain2 min/brain60 min = 10.1). Clear fluorescence signals retention in transgenic mice than control mice in in vivo near-infrared imaging. Hence, polyethylene glycol modified probes retained favorable optical properties but displayed great improvement of biological properties for Aβ detection.

Synthesis and antiviral bioactivities of 2-cyano-3-substitutedamino(phenyl) methylphosphonylacrylates (Acrylamides) containing alkoxyethyl moieties

An efficient reaction under microwave irradiation has been developed for the synthesis of a series of novel 2-cyano-3-substituted-amino(phenyl) methylphosphonylacrylates (acrylamides) II. The products obtained in shorter reaction time with moderate yields are fully characterized by elemental analysis, IR, 1H, 13C, and 31P NMR spectral data. The role of introducing various substituents and the effect of incorporating a-aminophosphonates with an alkoxyethyl moiety into the parent cyanoacrylate (acrylamide) structure are investigated. Among the studied compounds, both II-17 and II-24 displayed good in vivo curative, protection, and inactivation effects, which were comparable to those of the commercial reference ningnanmycin (inhibitory rates of 58.8, 60.2, 78.9% and 60.0, 58.9, 85.5%, respectively, at 500 mg/L against TMV). To the best of the authors' knowledge, this is the first report on the synthesis and antiviral activity of the title compounds II.

Synthesis and herbicidal activity of 2-cyano-3-substituted-pyridinemethylaminoacrylates

Two series of 2-cyano-3-substituted-pyridinemethylaminoacrylates, namely 12 new (Z)-2-cyano-3-methylthio-3-substituted-pyridinemethaneaminoacrylates and 10 new (Z)-2-cyano-3-alkyl-3-substituted-pyridinemethaneaminoacrylates, were synthesized as herbicidal inhibitors of photosystem II (PSII) electron transport. All of these compounds were confirmed by 1H NMR, elemental, IR, and mass spectrum analyses. Their herbicidal activities were evaluated. Some compounds exhibited excellent herbicidal activities, even at a dose of 75 g/ha. A suitable substituent at the 2-position of the pyridine ring and the well-fit group at the 3-position of acrylate were essential for high herbicidal activity. 2-Cyanoacrylates containing a substituted pyridine ring provide higher herbicidal activities than parent compounds containing phenyl. These PSII inhibitor herbicides are safe to corn, which is a major crop in China.

Novel 2-amino-1,4-dihydropyridine calcium antagonists. II. Synthesis and antihypertensive effects of 2-amino-1,4-dihydropyridine derivatives having N,N-dialkylaminoalkoxycarbonyl groups at 3- and/or 5-positions

Novel 2-amino-1,4-dihydropyridine derivatives I, which contain N,N-dialkylaminoalkoxycarbonyl groups at the 3- and/or 5-position, were synthesized and their antihypertensive effects were evaluated in spontaneously hypertensive rats. Remarkably prolonged duration of antihypertensive action was observed when a tertiary amino group was introduced into either the 3- or 5-ester side-chain of the 1,4-dihydropyridine ring. In particular, the compounds containing cyclic amino moieties at the 3-position showed greater potency than those with acyclic amino moieties. Chemical modification studies indicated that the two ester side-chains of 1,4-dihydropyridine at the 3- and 5-position might function in a different manner in relation to the antihypertensive activities. 3-(1-Benzhydrylazetidin-3-yl) 5-isopropyl 2-amino-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxyl ate, I-43 (CS-905), exhibited potent and long-lasting antihypertensive effects with gradual onset of action, and is a promising candidate as an antihypertensive drug.

The Influence of Electron Delocalization on the Rate Constants for Competing BAc2 and E1cb Ester Hydrolyses

The influence of electron-pair delocalization and leaving-group basicity upon the (E1cb)anion and (BAc2)anion mechanisms of ester hydrolysis are discussed.