1888-94-4

Usage

Uses

2-Chloroethyl methacrylate is used as a monomer to prepare poly(2-chloroethyl methacrylate).

InChI:InChI=1/C6H9ClO2/c1-5(2)6(8)9-4-3-7/h1,3-4H2,2H3

Upstream product

• 80-62-6 methacrylic acid methyl ester 
• 107-07-3 2-chloro-ethanol 
• 920-46-7 Methacryloyl chloride 
• 868-77-9 2-methyl-2-propenoic acid 2-hydroxyethyl ester 

Downstream Products

• 35838-12-1 tris-<2-(2-methyl 2-propenoic acid) ethyl ester> isocyanuric acid ester 
• 1055194-69-8 C₁₄H₁₇NO₄ 

Relevant academic research and scientific papers

Preparation and functionalization of linear and reductively degradable highly branched cyanoacrylate-based polymers

Ethyl cyanoacrylate (ECA) was polymerized radically in the presence of small amounts of trifluoroacetic acid as effective inhibitor of incidental anionic polymerization. Methyl methacrylate and other functional vinyl monomers (e.g., 2-chloroethyl and 2-bromoethyl methacrylate) were copolymerized with ECA, yielding linear ECA-rich copolymers, which could readily undergo further modifications, for instance nucleophilic substitution with azide. In the presence of a disulfide-containing dimethacrylate crosslinker and a chain transfer agent (CBr4) during the free radical copolymerizations of ECA with methacrylates, highly branched ECA-based polymers containing disulfide groups at the branching points were obtained prior to gelation. The polymers degraded upon addition of reducing agents. The prepared polymers, which contained peripheral (chain end) alkyl bromide groups as well as pendant alkyl chloride or bromide groups were then reacted with sodium azide, affording azide-containing polymers that were reacted with functional alkynes under copper-catalyzed “click” chemistry conditions.

The mechanism of a phosphazene-phosphazane rearrangement

The phosphazene-phosphazane rearrangement of N3P3Cl5O(CH2)2OC(O)CMeCH2 (8) has been examined in detail using one and two dimensional NMR (31P, 1H) spectroscopy and mass spectrometry. The mixed phosphazene-phosphazane [NPCl2]2[N((CH2)2OC(O)CMeCH2)P(O)Cl] (14), [NPCl2]2[NHP(O)Cl] (13) and a two ring assembly [NPCl2]2[NP(O{(NPCl2)2(N((CH2)2OC(O)CMeCH2)P(O)}] (15) have all been detected in the product mixture. The rate of the rearrangement has been measured at five temperatures by 31P and 1H NMR. The reaction is first order in 8 (T1/2 at 111° is 4.65 hours). The activation enthalpy is positive and the activation entropy is negative. A mechanism involving competing intra and inter molecular processes which fits the product distribution and kinetic data has been proposed. Several other methyacrylphosphazenes were examined under the same thermolysis conditions. The rearrangement was observed and the rates obtained in cases where the (CH2)2 spacer unit of the methacrylate was replaced by linear and branched propyl units. The rearrangement was not observed when the methacrylate was appended to a spirocyclic unit, the spacer unit was extended to the n-butyl group and when the methacrylate unit was replaced by a methoxy group. These results are all consistent with the proposed mechanism. This investigation resolves conflicting results previous reported for the rearrangement.

Effective addition of organic chloride salts on atom transfer radical polymerization in fluoroalcohols

Atom transfer radical polymerization (ATRP) of methyl methacrylate (MMA) in the presence of organic chloride salts, imidazolium chlorides, using alkyl bromide initiator was carried out in 2,2,2-trifluoroethanol (TFE) at 333 K. The ATRP using a sufficient large amount of chloride salts proceeded in a controlled manner to produce polymers with narrow molecular weight distributions (M w/Mn 1.2). The model reaction using an alkyl bromide and the imidazolium chloride indicated that a halogen exchange reaction occurred during the ATRP in TFE to form a chloride-terminated propagating species from the alkyl bromide. ATRP of MMA in TFE using an alkyl chloride initiator and CuCl catalyst, however, gave low initiation efficiency and loss of control over the polymerization. The combination of the alkyl bromide initiator, CuBr, and a sufficient amount of organic chloride salts was very effective to improve the control of ATRP in protic solvents, especially in fluoroalcohols. A methacrylate monomer bearing imidazolium chloride moiety was synthesized and polymerized by ATRP without added chloride salts to produce the polymers with well-controlled molecular weights and narrow polydispersities.

Enhanced delivery of the RAPTA-C macromolecular chemotherapeutic by conjugation to degradable polymeric micelles

Macromolecular ruthenium complexes are a promising avenue to better and more selective chemotherapeutics. We have previously shown that RAPTA-C [RuCl2(p-cymene)(PTA)], with the water-soluble 1,3,5- phosphaadamantane (PTA) ligand, could be attached to a polymer moiety via nucleophilic substitution of an available iodide with an amide in the PTA ligand. To increase the cell uptake of this macromolecule, we designed an amphiphilic block copolymer capable of self-assembling into polymeric micelles. The block copolymer was prepared by ring-opening polymerization of d,l-lactide (3,6-dimethyl-1,4-dioxane-2,5-dione) using a RAFT agent with an additional hydroxyl functionality, followed by the RAFT copolymerization of 2-hydroxyethyl acrylate (HEA) and 2-chloroethyl methacrylate (CEMA). The Finkelstein reaction and reaction with PTA led to polymers that can readily react with the dimer of RuCl2(p-cymene) to create a macromolecular RAPTA-C drug. RAPTA-C conjugation, micellization, and subsequent cytotoxicity and cell uptake of these polymeric moieties was tested on ovarian cancer A2780, A2780cis, and Ovcar-3 cell lines. Confocal microscopy images confirmed cell uptake of the micelles into the lysosome of the cells, indicative of an endocytic pathway. On average, a 10-fold increase in toxicity was found for the macromolecular drugs when compared to the RAPTA-C molecule. Furthermore, the cell uptake of ruthenium was analyzed and a significant increase was found for the micelles compared to RAPTA-C. Notably, micelles prepared from the polymer containing fewer HEA units had the highest cytotoxicity, the best cell uptake of ruthenium and were highly effective in suppressing the colony-forming ability of cells.

LIGHT FILTERS COMPRISING A NATURALLY OCCURRING CHROMOPHORE AND DERIVATIVES THEREOF

A composition comprising a polymer backbone and at least one side group, wherein the side group comprises a benzene ring-based chromophore comprising a ketone at the 1-position, a substituted or unsubstituted amino group at the 2-position, and an oxygen atom at the 3-position of the benzene ring. The chromophore is a kynurenine-based compound. Methods of making and using the composition are also provided. The composition can be used in an ophthalmic lens or device for protecting the retina by blocking UV rays and filtering violet rays.