2-{[(Butylsulfanyl)carbonothioyl]sulfanyl}propanoic acid

Name: 2-{[(Butylsulfanyl)carbonothioyl]sulfanyl}propanoic acid
SKU: ACM480436462
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CAS

480436-46-2

Catalog Number

ACM480436462

Category

Main Products

Molecular Weight

238.39

Molecular Formula

C8H14O2S3

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Specification

Synonyms

2-Butylsulfanyl-thiocarbonylsulfanyl-propionic acid

Appearance

Yellow to orange to brown
solid

Synthesis of RAFT Statistical Copolymers Using 2-{[(Butylsulfanyl)carbonothioyl]sulfanyl}propanoic Acid as Chain Transfer Agent

Synthetic route used to coat GO with a polymeric shell using 2-{[(butylsulfanyl)carbonothioyl] sulfanyl} propanoic acid chain transfer agent.

Huynh, Vien T., et al. Journal of Polymer Science Part A: Polymer Chemistry, 2015, 53(12), 1413-1421.

The research produced low molecular weight anionic RAFT statistical copolymers of sodium styrene sulfonate acrylic acid and butyl acrylate BA through initial synthesis with 2-{[(Butylsulfanyl)carbonothioyl]sulfanyl}propanoic acid as the chain transfer agent. The copolymers were then used to stabilize graphene oxide (GO) pretreated with polyallylamine hydrochloride (PAH). The resulting coated GO demonstrated good dispersibility in both water and various organic solvents with differing polarities.
The coating process involved a synthetic route that included: (i) the alternate adsorption of the positively charged PAH, followed by (ii) the negatively charged macro-RAFT copolymer, and ultimately (iii) chain extension of the adsorbed macro-RAFT copolymer using a 10/1 w/w mixture of MMA and BA under stave-fed conditions.
Detailed synthesis procedure of copolymers: The copolymer synthesis required the combination of 2-{[(Butylsulfanyl)carbonothioyl]sulfanyl}propanoic acid (1.2 g, 5.0 mmol), 4,4'-azobis(4-cyanovaleric acid) (V-501, 0.074 g, 0.3 mmol), acrylic acid (AA, 3.64 g, 50.5 mmol), sodium styrene sulfonate (StS, 5.19 g, 25.2 mmol), and butyl acrylate (BA, 2.64 g, 20.6 mmol) with dioxane (10.00 g) and water (10.69 g) in a 50 mL round-bottom flask. A magnetic stirrer mixed the solution which was then purged with nitrogen for 10 minutes and the temperature was increased to 70°C for 7 hours while continuous stirring was maintained. The copolymer solution achieved a solids content of 34.9%.

2-{[(Butylsulfanyl)Carbonothioyl]Sulfanyl}Propanoic Acid Chain Transfer Agent for the Synthesis of Thermosensitive Copolymers

Properties of poly(eDEGA-stat-mDEGA) copolymers synthesized with PABTC as chain transfer agent.

Voorhaar, Lenny, et al. Controlled Radical Polymerization: Materials. American Chemical Society, 2015, 63-77.

This study utilized 2-{[(butylsulfanyl)carbonothioyl]sulfanyl}propanoic acid (PABTC) as a chain transfer agent (CTA) to synthesize two series of thermosensitive statistical copolymers via high-throughput automated RAFT polymerization. The copolymers comprised di(ethylene glycol) ethyl ether acrylate (eDEGA) combined with either di(ethylene glycol) methyl ether acrylate (mDEGA) or tri(ethylene glycol) methyl ether acrylate (mTEGA), aiming to precisely tailor their phase transition temperatures. PABTC was selected for its versatility in mediating RAFT polymerization across diverse acrylates and acrylamides.
Synthesis Protocol
Stock solutions of PABTC, AIBN initiator, and monomers in DMF were argon-purged for ≥30 minutes and maintained under inert conditions using a nitrogen-flushed automated synthesizer. Reactors underwent ten vacuum-argon degassing cycles prior to reagent transfer at 10°C. Polymerizations employed a molar ratio of [M]:[PABTC]:[AIBN] = 100:1:0.1, with total monomer concentration fixed at 2.0 M in DMF (4 mL volume). Comonomer ratios (eDEGA:mDEGA and eDEGA:mTEGA) spanned 100:0 to 0:100 in incremental steps, with reactions conducted in duplicate. After collecting a t = 0 sample for baseline conversion analysis, reactors were heated to 70°C (11-minute ramp) to initiate polymerization. Aliquots (50 µL) were extracted every 20 minutes into acetone for GC/SEC monitoring. Reactions ceased after 2 hours by cooling to 10°C.
Purification
Crude polymers were diluted with water, heated (80°C), and centrifuged (7500 RPM, 1 minute). After decanting, residues were redissolved in cold water, reheated, and recentrifuged. Polymers were then dissolved in dichloromethane and vacuum-dried. mTEGA homopolymers underwent dialysis to remove residual monomers.

What is the molecular formula of the chemical?

The molecular formula is C8H14O2S3.

What are the synonyms of the chemical?

The synonyms of the chemical are:
480436-46-2
2-(Butylthiocarbonothioylthio)propanoic acid
2-{[(Butylsulfanyl)carbonothioyl]sulfanyl}propanoic acid
2-{[(BUTYLSULFANYL)METHANETHIOYL]SULFANYL}PROPANOIC ACID
1671063-74-3

What is the molecular weight of the chemical?

The molecular weight is 238.4 g/mol.

When was the chemical created and modified?

The chemical was created on August 20, 2012, and last modified on October 21, 2023.

What is the IUPAC name of the chemical?

The IUPAC name of the chemical is 2-butylsulfanylcarbothioylsulfanylpropanoic acid.

What is the InChI of the chemical?

The InChI of the chemical is: InChI=1S/C8H14O2S3/c1-3-4-5-12-8(11)13-6(2)7(9)10/h6H,3-5H2,1-2H3,(H,9,10)

What is the InChIKey of the chemical?

The InChIKey of the chemical is VQUDUXBWOHBISV-UHFFFAOYSA-N.

What is the Canonical SMILES of the chemical?

The Canonical SMILES of the chemical is CCCCSC(=S)SC(C)C(=O)O.