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121-68-6

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121-68-6 Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 1282, 1965 DOI: 10.1021/jo01015a530

Check Digit Verification of cas no

The CAS Registry Mumber 121-68-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 1 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 121-68:
(5*1)+(4*2)+(3*1)+(2*6)+(1*8)=36
36 % 10 = 6
So 121-68-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H6S2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)

121-68-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name benzenecarbodithioic acid

1.2 Other means of identification

Product number -
Other names m-dithiobenzoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:121-68-6 SDS

121-68-6Relevant articles and documents

Thermally controlled wettability of a nanoporous membrane grafted with catechol-tethered poly(N-isopropylacrylamide)

Kim, Jee Seon,Kim, Taek Gyung,Kong, Won Ho,Park, Tae Gwan,Nam, Yoon Sung

, p. 9227 - 9229 (2012)

A nanoporous membrane is coated with catechol-tethered poly(N- isopropylacrylamide). The thermosensitive variation of surface wettability determines the hindered diffusivity of dextran (40 kDa) through the nanopores.

Synthesis and characterization of well-defined optically active methacrylic diblock copolymers

Achilleos, Mariliz,Kafouris, Demetris,Holder, Simon J.,Krasia-Christoforou, Theodora

, p. 4215 - 4222 (2012)

A new, simple, and cost-effective approach toward the development of well-defined optically active diblock copolymers based on methacrylate monomers is described for the first time. Starting from the low-cost optically active (S)-(-)-2-methyl-1-butanol, a new optically active methacrylic monomer, namely, (S)-(+)-2-methyl-1-butyl methacrylate [(S)-(+)-MBuMA], was synthesized. Reversible addition fragmentation chain transfer polymerization was then used for preparing well-defined poly[(S)-(+)-MBuMA] homopolymers and water-soluble diblock copolymers based on [(S)-(+)-MBuMA] and the hydrophilic and ionizable monomer 2-(dimethyl amino)ethyl methacrylate (DMAEMA). The respective homopolymers and diblock copolymers were characterized in terms of their molecular weights, polydispersity indices, and compositions by size exclusion chromatography and 1H NMR spectroscopy. Polarimetry measurements were used to determine the specific optical rotations of these systems. The structural and compositional characteristics of micellar nanostructures possessing an optically active core generated by p((S)-(+)-MBuMA)-b-p(DMAEMA) chains characterized by predetermined molecular characteristics may be easily tuned to match biological constructs. Consequently, the aggregation behavior of the p[(S)-(+)-MBuMA]-b-p[DMAEMA] diblock copolymers was investigated in aqueous media by means of dynamic light scattering and atomic force microscopy, which revealed the formation of micelles in neutral and acidified aqueous solutions.

Thermal decomposition of cumyl dithiobenzoate

Liu, Yang,He, Junpo,Xu, Jiangtao,Fan, Deqin,Tang, Wei,Yang, Yuliang

, p. 10332 - 10335 (2005)

Thermal decomposition of cumyl dithiobenzoate (CDB), a reagent widely used in controlled polymerization of various monomers, was investigated. CDB was synthesized by flash chromatography followed by recrystallization and obtained as large purple crystals. A close analysis of the MS spectra revealed the presence of isopropylbenzene and cumyl thiobenzoate. Results show that the polymeric dithioesters, which are more stable than CDB, are formed after the initiation period, accounting for the fact that CDB-mediated RAFT polymerization of styrene works well at high temperature.

Intracellular nitric oxide delivery from stable NO-polymeric nanoparticle carriers

Duong, Hien T. T.,Kamarudin, Zulkamal M.,Erlich, Rafael B.,Li, Yang,Jones, Mathew W.,Kavallaris, Maria,Boyer, Cyrille,Davis, Thomas P.

, p. 4190 - 4192 (2013)

The encapsulation of S-nitrosoglutathione into polymeric nanoparticles substantially improves NO stability in aqueous media without affecting the efficacy of intracellular delivery. The combination of nano-NO delivery and chemotherapy has been found to enhance antitumour activity of chemotherapeutics, as demonstrated using preliminary in vitro experiments with neuroblastoma cells.

RAFT polymer end-group modification and chain coupling/conjugation Via disulfide bonds

Boyer, Cyrille,Liu, Jingquan,Bulmus, Volga,Davis, Thomas P.

, p. 830 - 847 (2009)

End-group modification of polymers prepared by reversible additionfragmentation chain transfer (RAFT) polymerization was accomplished by the conversion of trithiocarbonate or dithioester end-groups into a pyridyl disulfide (PDS) functionality. Several different polymers, such as poly(methyl methacrylate), polystyrene, poly(oligoethylene glycol-acrylate), poly(hydroxypropylacrylamide), and poly(N-isopropylacrylamide) were prepared by RAFT polymerization, and subjected to aminolysis in the presence of 2,2′-dithiodipyridine to yield thiol-terminated polymers with yields in the range 6590% dependent on the polymer structure. Furthermore, this PDS end-group was utilized to generate higher-order architectures, such as diblock copolymers with high yields and selectively. In addition, the PDS end-groups were used for the bioconjugation of different biomolecules, such as oligonucleotides, carbohydrates, and peptides. The successful modification of well-defined polymers was confirmed by a combination of UV-vis, NMR spectroscopy, and gel permeation chromatography.

First RAFT polymerization of captodative 2-acetamidoacrylic acid (AAA) monomer: An experimental and theoretical study

Dedeo?lu, Burcu,U?ur, Ilke,De?irmenci, Isa,Aviyente, Viktorya,Bar?in, Bilin?,?ayli, G?khan,Acar, Havva Yagci

, p. 5122 - 5132 (2013)

A capto-dative monomer, 2-acetamidoacrylic acid (AAA), was homopolymerized through RAFT polymerization method using 2-(2-cyanopropanyl dithiobenzoate) (CPDB) as a chain transfer agent and AIBN free radical initiator in DMF at 70 C. DFT calculations were performed in the selection of the CTA for this unique monomer as well as to elucidate the influence of cd-stabilized growing radical on the kinetic parameters in comparison to methacrylic acid (MAA) and N-(prop-1-en-2-yl)acetamide (NPAA), which represent the captive and dative groups of AAA, respectively. Keq for these three monomers is in the order of AAA β > k-add for NPAA and MAA, for AAA k-add is about four orders of magnitude larger than kβ. This is the major disadvantage in the RAFT process of AAA using CPDB. Yet, poly(AAA) could be achieved with PDI as low as 1.49. Molecular weight of the polymer can be tuned by the monomer/AIBN ratio. First block copolymers of AAA with MAA and MMA using poly(AAA) as a macro-CTA were also synthesized, indicating the presence of active chain ends.

Simplification of the synthesis of the reversible addition-fragmentation chain transfer agent 2-(2-cyanopropyl)-dithiobenzoate

Milovanovic, Milos B.,Avramovic, Milena,Katsikas, Lynne,Popovic, Ivanka G.

, p. 1711 - 1719 (2010)

The general literature procedure for the preparation of the reversible addition-fragmentation chain transfer (RAFT) agent 2-(2-cyanopropyl)- dithiobenzoate (CPDB) was modified by omitting the recrystallisation of the intermediate di(thiobenzoyl)disulphide. The yield of the CPDB in the simplified synthesis was increased four times compared to the standard one. The behaviour of the CPDB obtained by the modified procedure and by the standard one in the polymerisation of methyl methacrylate was investigated. The CPDB synthesized by the simplified procedure showed itself to be a good RAFT agent, giving excellent control over the polymerisation of methyl methacrylate and it behaved in the same manner as the CPDB prepared by the literature method. The obtained poly(methyl methacrylate) had a narrow molecular weight distibution (PD = 1.1).

Reaction of cyclic tetrathiophosphates with carboxylic acids as a means to generate dithioesters and control radical polymerization by RAFT

Dureault, Alex,Gnanou, Yves,Taton, Daniel,Destarac, Mathias,Leising, Frederic

, p. 2869 - 2872 (2003)

Radical control: Controlled free-radical polymerization of styrene and methyl (meth)acrylate is achieved by using Davy reagents or P4S10 in conjunction with benzoic acid, which leads to in situ formation of dithioesters that act as chain-transfer agents and thus control the reaction. In the case of P4S10/PhCOOH, d[thiobenzoic acid is the key intermediate in this process (see scheme).

Monodisperse, micron-sized reactive low molar mass polymer microspheres by two-stage living radical dispersion polymerization of styrene

Song, Jing-She,Winnik, Mitchell A.

, p. 8318 - 8325 (2006)

Living/controlled radical dispersion polymerization of styrene was carried out in ethanol and in ethanol-water mixtures in the presence of perfluorohexyl iodide (C6F13I, 2-5 wt % based on styrene) as a degenerative chain transfer (DCT) agent or 1-cyano-1-methylpropyl dithiobenzoate (CMPDB, 0.5 and 1.0 mol % based on styrene) as a reversible addition-fragmentation chain transfer (RAFT) agent. These reagents disrupt the nucleation stage of particle formation when present at the start of the reaction. If their addition is delayed until the nucleation stage is complete, the reaction acquires the characteristics of a living/controlled radical polymerization: Mn increases linearly with the monomer conversion, and the molar mass distribution is much narrower (minimal Mw/M n: 1.2) than polystyrene prepared without C6F 13I or CMPDB. For reactions in ethanol, at low molar mass, the particles formed have a broad size distribution as a consequence of the solubility of the polymer at the reaction temperature, followed by precipitation upon cooling. When the reactions were run in a more polar medium (95 wt % aqueous ethanol), the polymer molecules precipitated as they were formed and were absorbed by the existing particles in the solution. The particles formed had an average diameter in the range 1-3 μm with a very narrow size distribution (CV 1%). The polymer chains in these particles are reactive and chain-extendible.

Imparting nanoparticle function with size-controlled amphiphilic polymers

Chen, Yingchuan,Thakar, Rahul,Snee, Preston T.

, p. 3744 - 3745 (2008)

Herein we report our method of water solubilization and subsequent functionalization of a variety of nanoparticle systems with amphiphilic polymers containing build-in "chemical handles". We have used these polymers, which have narrow polydispersity indices, to impart water solubility and chemical sensitivity toward targeted species (here: pH). These material systems have high chemical conjugation efficiencies in aqueous conditions which may be used to create a variety of chemical and biological multifunctional materials. Copyright

Carbohydrate-based amphiphilic diblock copolymers with pyridine for the sensitive detection of protein binding

Otsuka, Hidenori,Hagiwara, Toshiya,Yamamoto, Sayuri

, p. 6764 - 6773 (2014)

Glycopolymers are useful macromolecules for presenting carbohydrates in multivalent form. Here, amphiphilic block copolymers consisting of hydrophilic lactose and hydrophobic pyridine were synthesized via reversible addition-fragmentation chain transfer polymerization (RAFT). RAFT polymerization of 2-O-methacryloyloxyethyl-(-D-lactoseheptaacetate) (2-O-MALac) was performed using cumyl dithiobenzoate (CDB) as the chain transfer agent to give well-defined glycopolymers. The livingness of the process was further demonstrated by successfully chain-extending one of obtained glycopolymers with 4-pyridyl methyl methacrylate affording narrow dispersed diblocks. With the obtained block copolymers, a glycosurface was generated on the gold surface of quartz crystal microbalance (QCM) through self-assembled strategy by the use of gold affinitive pyridine functional group. Furthermore, the resulting glycosurface was used to detect the binding of lactose specific lectin, ricinus communis agglutinin (RCA120) without non-specific protein adsorption.

Strain-Promoted 1,3-Dithiolium-4-olates–Alkyne Cycloaddition

Kumar, Ramar Arun,Pattanayak, Manas R.,Yen-Pon, Expédite,Eliyan, Jijy,Porte, Karine,Bernard, Sabrina,Riomet, Margaux,Thuéry, Pierre,Audisio, Davide,Taran, Frédéric

supporting information, p. 14544 - 14548 (2019/09/17)

Reported here is the reactivity of mesoionic 1,3-dithiolium-4-olates towards strained alkynes, leading to thiophene cycloaddition products. In the process, the potential of these dipoles towards orthogonal reaction with azides, allowing efficient double ligation reactions, was discovered. A versatile process to access benzo[c]thiophenes, in an unprecedented divergent fashion, was developed and provides a new entry to unconventional polyaromatic thiophenes.

Pt nanoparticles stabilized by thermosensitive polymer as effective and recyclable catalysts for the asymmetric hydrogenation of ethyl pyruvate

Yu, Wenjun,Lou, Lan-Lan,Yu, Kai,Li, Shanshan,Shi, Yang,Liu, Shuangxi

, p. 52500 - 52508 (2016/06/13)

Thermosensitive and thiol-terminated poly(N-isopropylacrylamide)s (PNIPAM-SHs) were synthesized and used to stabilize Pt nanoparticles. After chiral modification with cinchonidine, these nanocatalysts were firstly applied in the asymmetric hydrogenation of ethyl pyruvate. The influences of reaction solvent, chiral modifier concentration, hydrogen pressure, mean molecular weight and amount of polymer on the catalytic performance were investigated. These colloidal Pt catalysts exhibited remarkably high catalytic activity and enantioselectivity. Especially, high turnover frequencies up to 17:820 h-1 were achieved, which is the best result for this reaction with regard to the colloidal Pt catalysts. The high catalytic activity was associated with the high hydrophobicity of isopropyl groups in polymer moieties in the catalyst. Moreover, recycling experiments showed that the thermosensitivity of PNIPAM-SH made these colloidal Pt catalysts easier to recover and reuse. Excellent stability and reusability were presented over these catalysts, and no obvious decrease in catalytic activity and enantioselectivity was observed for eleven runs.

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