2 dodecylthiocarbonothioylthio 2 methylpropionic acid

Manufactured by Merck Group

Sourced in United States

2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid is a chemical compound used as a laboratory reagent. It has the molecular formula C~17~H~34~O~2~S~3~. The compound serves as a chain transfer agent in polymerization reactions.

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7 protocols using 2 dodecylthiocarbonothioylthio 2 methylpropionic acid

Synthesis and Characterization of Sulfobetaine-Based Polymers

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Sulfobetaine (SPB) monomer was donated by Osaka Organic Chemical (Osaka, Japan) and used without further purification. 2-(Dodecylthiocarbonothioylthio)-2-methylpropionic acid, Thioflavin T (ThT), Micrococcus lysodeikticus, and lysozyme from chicken egg white were purchased from Sigma-Aldrich. Azobisisobutyronitrile (AIBN) was purchased from Wako Pure Chemical Industries (Osaka, Japan) and was recrystallized from methanol before use. Ethylene glycol dimethacrylate, BuMA and 4,4′-azobis-(4-cyanovaleric acid) (V-501, initiator) were purchased from TCI (Tokyo, Japan). Prior to its use, the inhibitor from BuMA was removed by passing through an inhibitor removal prepacked column (Sigma-Aldrich).

Rajan R, & Matsumura K. (2017). Inhibition of protein aggregation by zwitterionic polymer-based core-shell nanogels. Scientific Reports, 7, 45777.

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Thermoresponsive Polymer Synthesis

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N-isopropylacrylamide (NIPAAm), 2,2-azobisisobutyronitrile (AIBN), 1,4-dioxane, hexane, acetone, 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid, N,N′-methylenebis(acrylamide), fluorescein O-methacrylate, fluorescein (free acid), sodium thiocyanate (NaSCN), and sodium sulfate (Na₂SO₄) were purchased from Sigma Aldrich (St. Louis, MO, USA). Deuterated chloroform was supplied from Cambridge Isotope Ltd., (Tewksbury, MA, USA) and N,N-dimethylformamide (DMF) was purchased from Rathburn (Walkerburn, UK).

Joubert F., Cheong Phey Denn P., Guo Y, & Pasparakis G. (2019). Comparison of Thermoresponsive Hydrogels Synthesized by Conventional Free Radical and RAFT Polymerization. Materials, 12(17), 2697.

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Synthesis of Methoxypolyethylene Glycol-Functionalized Polymer

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All the chemicals were analytical grade and used as received without any further purifications. 4-hydroxybenzaldehyde, Methoxypolyethylene glycols, 2-(Dodecyl- thiocarbonothioylthio)-2-methylpropionic acid (DDMAT), 11-bromoundecan-1-ol, Azo-bisisobutyronitrile (AIBN), Methacryloyl chloride, 4-butylphenylethylketone, N,N-Dimethylformamide (DMF), were all purchased from Sigma-Aldrich and Alfa-Aesar. Anisole was procured from Sigma-Aldrich with extra-dry grade purification.

Li J., Chen Z., Umar A., Liu Y., Shang Y., Zhang X, & Wang Y. (2017). Probe Into the Influence of Crosslinking on CO2 Permeation of Membranes. Scientific Reports, 7, 40082.

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Synthesis of Diverse Acrylate and Methacrylate Monomers

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Glyceryl monomethacrylate (GMA; 98%, supplied
by GEO Specialty Chemicals), poly(ethylene glycol) methyl ether acrylate
(PEGA, M_n = 480, Sigma-Aldrich), poly(ethylene
glycol) methyl ether methacrylate (PEGMA, M_n = 950, Sigma-Aldrich), acrylic acid (AA, 99%; Fisher), methacrylic
acid (MAA, ≥99%; Merck), lauryl acrylate (LA, >98%, TCI
Chemicals), iso-octyl acrylate (ⁱOA, >90%;
Sigma-Aldrich),
2-ethylhexyl acrylate (EHA, Alfa Aesar, 98%), iso-bornyl acrylate (ⁱBA 99%; Alfa Aesar), tert-butyl acrylate (^tBuA, 99%; Alfa Aesar), 3,5,5-trimethylhexyl
acrylate (TMHA; Sigma-Aldrich), 3,5,5-trimethylhexyl methacrylate
(TMHMA, ABCR), and tert-octyl acrylamide (OAA; supplied
by ABCR, Germany) were all used as received. Asoisobutyronitrile (AIBN)
was recrystallized twice from mEthanol. Ethanol (99.8%, Fisher), mEthanol
(>99%, Sigma-Aldrich), THF, and n-heptane (>99%,
Sigma-Aldrich) were used as received. 2-(Dodecylthiocarbonothioylthio)-2-methylpropionic
acid (DDMAT, 98%) was purchased from Sigma-Aldrich and used as received.
MilliQ water was obtained from an Elga Elgastat Option 3A Water Purifier
system.

Jennings J., Webster-Aikman R.R., Ward-O’Brien N., Xie A., Beattie D.L., Deane O.J., Armes S.P, & Ryan A.J. (2022). Hydrocarbon-Based Statistical Copolymers Outperform Block Copolymers for Stabilization of Ethanol–Water Foams. ACS Applied Materials & Interfaces, 14(34), 39548-39559.

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RAFT Polymerization of Styrene and Acrylic Acid

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2-(Dodecylthiocarbonothioylthio)-2-methylpropionic acid as the RAFT-agent, and styrene (ST), acrylic acid (AA) monomers were acquired from Sigma Aldrich. Isopropyl alcohol (IPA), chloroform, benzene, o-xylene, benzophenone (BP), acetic acid, toluidine blue (TB), hydrochloric acid, N,N-dimethylformamide and sodium hydroxide have a purity of analytical grade ≥95%. Deionized water (18.2 MΩ) was prepared by Akvilon-D 301, PVC film (ISOLAB Laborgeraete GmbH, Germany), UV lamp (OSRAM Ultra Vitalux E27, Slovakia) was used in grafting, and a UV lamp (Osram Puritec, Germany) was used in photosensitization.

Muslimova I.B., Zhumanazar N., Melnikova G.B., Yeszhanov A.B., Zhatkanbayeva Z.K., Chizhik S.A., Zdorovets M.V., Güven O, & Korolkov I.V. (2024). Preparation and application of stimuli-responsive PET TeMs: RAFT graft block copolymerisation of styrene and acrylic acid for the separation of water–oil emulsions. RSC Advances, 14(20), 14425-14437.

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Synthesis of Functional Polymers

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Dopamine hydrochloride, sodium tetraborate
decahydrate (Na₂B₄O₇·10H₂O), sodium carbonate (Na₂CO₃), trisDCMP,
and 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid were purchased
from Sigma-Aldrich Co. LLC. Hydrochloric acid (HCl), 2,2-dimethoxypropane,
ethyl acetate, sodium sulfate (Na₂SO₄), hexane,
TFA, and ethyl acetate were purchased from Kanto Chemical Co. Inc.
Acryloyl chloride, 2,2′-azobis(isobutyronitrile) (AIBN), N,N-dimethylformamide (DMF), tetrahydrofuran
(THF), and p-toluenesulfonic acid monohydrate (p-TsOH·H₂O) were obtained from Tokyo Chemical
Industry Co., Ltd. Diphenyl-2,4,6-trimethylphenylsulfonium p-toluenesulfonate was obtained from Wako Pure Chemical
Co. All of the chemicals and solvents were of reagent grade and were
used as received.

Kohri M., Yamazaki S., Irie S., Teramoto N., Taniguchi T, & Kishikawa K. (2018). Adhesion Control of Branched Catecholic Polymers by Acid Stimulation. ACS Omega, 3(12), 16626-16632.

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Synthesis of CTA Agents for RAFT Copolymerization

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1-Dodecanthiol, carbon disulfide, potassium phosphate, 2-bromo-2-methylpropionic acid, and acetone were purchased from Sigma-Aldrich (St. Louis, MO) and used for the synthesis of 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid as a CTA for the RAFT copolymerization of acrylate monomers. The other CTA, 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanoic acid, was purchased from Sigma-Aldrich and used for the RAFT copolymerizations when the copolymerization mixture contained a methacrylate monomer. Azobisisobutyronitrile (AIBN, 98%) was purchased from Junsei (Tokyo, Japan) and purified by recrystallization in methanol. Poly(ethylene glycol) methyl ether acrylate (PEGA), dodecyl acrylate (DA), poly(ethylene glycol) methyl ether methacrylate (PEGMA), and dodecyl methacrylate (DMA) were purchased from Sigma-Aldrich and TCI (Tokyo, Japan). They were purified by passing through a basic alumina column prior to polymerization. HPLC grade toluene was purchased from Burdick & Jackson (Morristown, NJ) and used as a polymerization solvent after purification using a solvent purification system (C&T International, Suwon, Korea).

Shin M., Kim H., Park G., Park J., Ahn H., Yoon D.K., Lee E, & Seo M. (2022). Bilayer-folded lamellar mesophase induced by random polymer sequence. Nature Communications, 13, 2433.

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