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Cas Database

39549-10-5

39549-10-5

Identification

  • Product Name:1-(p-tolylthio)pyrrolidine-2,5-dione

  • CAS Number: 39549-10-5

  • EINECS:

  • Molecular Weight:221.28

  • Molecular Formula: C11H11NO2S

  • HS Code:2930909090

  • Mol File:39549-10-5.mol

Synonyms:N-(p-tolylthio)succinimide;1-(p-tolylthio)pyrrolidine-2,5-dione;2,5-Pyrrolidinedione,1-[(4-methylphenyl)thio];N-(Toluol-4-sulfenyl)-succinimid;4-tolylsulfensuccinimide;N-(p-Tolyl-sulfenyl)-succinimid;N-(4-methylbenzene)thiosuccinimide;N-(toluene-4-sulfenyl)-succinimide;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 19 Articles be found

Regioselective C-H Thioarylation of Electron-Rich Arenes by Iron(III) Triflimide Catalysis

Dodds, Amy C.,Sutherland, Andrew

, p. 5922 - 5932 (2021/05/04)

A mild and regioselective method for the preparation of unsymmetrical biaryl sulfides using iron(III) catalysis is described. Activation of N-(arylthio)succinimides using the powerful Lewis acid iron(III) triflimide allowed the efficient thiolation of a range of arenes, including anisoles, phenols, acetanilides, and N-heterocycles. The method was applicable for the late-stage thiolation of tyrosine and tryptophan derivatives and was used as the key step for the synthesis of pharmaceutically relevant biaryl sulfur-containing compounds such as the antibiotic dapsone and the antidepressant vortioxetine. Kinetic studies revealed that while N-(arylthio)succinimides bearing electron-deficient arenes underwent thioarylation catalyzed entirely by iron(III) triflimide, N-(arylthio)succinimides with electron-rich arenes displayed an autocatalytic mechanism promoted by the Lewis basic product.

Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N -Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes

Kumari, Arram Haritha,Kumar, Jangam Jagadesh,Krishna, Gamidi Rama,Reddy, Raju Jannapu

supporting information, p. 2850 - 2864 (2021/05/18)

An efficient nickel-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes were also successfully explored in this 1,2-thiosulfonylation process. Moreover, the nickel-catalyzed geminal -dithiolation of alkynyl bromides with N -arylthio succinimides provides 1,1-dithioalkenes in high yields. The present protocol is reliable on gram scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene is achieved in a scale-up synthesis. Following control experiments, a plausible mechanism is proposed to rationalize the experimental outcome and the vicinal thio-sulfonylation.

Catalytic Electrophilic Thiocarbocyclization of Allenes

Jiang, Quanbin,Li, Huimin,Zhao, Xiaodan

supporting information, p. 8777 - 8782 (2021/11/17)

An efficient approach via catalytic electrophilic thiocarbocyclization of allenes to construct indene-based sulfides with excellent regioselectivities is disclosed. The reactions were carried out at low temperatures by selenide catalysis in the presence o

3-Thiolated pyrroles/pyrrolines: controllable synthesis and usage for the construction of thiolated fluorophores

Tian, Jun,Yuan, Kang-Ning,Liu, Wen,Chang, Hong-Hong,Li, Xing,Gao, Wen-Chao

supporting information, p. 1943 - 1946 (2021/03/02)

Thiolation/cyclization of homopropargylic tosylamides allowed the selective synthesis of 3-thiolated pyrroles and pyrrolines controlled by solvents. Moreover, the desired 3-thiolated pyrroles were readily transformed to organic fluorophores benzothienopyrrole and bisthiolated boron dipyrromethene (S-BODIPY).

Enantioselective Construction of Axially Chiral Amino Sulfide Vinyl Arenes by Chiral Sulfide-Catalyzed Electrophilic Carbothiolation of Alkynes

Ji, Jieying,Jiang, Quanbin,Liang, Yaoyu,Luo, Jie,Zhang, Xiaoyan,Zhao, Xiaodan

supporting information, p. 4959 - 4964 (2020/02/11)

The enantioselective construction of axially chiral compounds by electrophilic carbothiolation of alkynes is disclosed for the first time. This enantioselective transformation is enabled by the use of a Ts-protected bifunctional sulfide catalyst and Ms-protected ortho-alkynylaryl amines (Ts=tosyl; Ms=mesyl). Both electrophilic arylthiolating and electrophilic trifluoromethylthiolating reagents are suitable for this reaction. The obtained products of axially chiral vinyl–aryl amino sulfides can be easily converted into biaryl amino sulfides, biaryl amino sulfoxides, biaryl amines, vinyl–aryl amines, and other valuable difunctionalized compounds.

Process route upstream and downstream products

Process route

para-thiocresol
106-45-6

para-thiocresol

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione
39549-10-5

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

Conditions
Conditions Yield
para-thiocresol; With sulfuryl dichloride; triethylamine; In dichloromethane; at 0 - 20 ℃;
Succinimide; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h;
60%
N-chloro-succinimide
128-09-6

N-chloro-succinimide

para-thiocresol
106-45-6

para-thiocresol

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione
39549-10-5

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione

Conditions
Conditions Yield
N-chloro-succinimide; para-thiocresol; In toluene; at 20 ℃; for 1h; Inert atmosphere;
With triethylamine; In toluene; at 40 ℃; for 16h; Inert atmosphere;
90%
With triethylamine; In dichloromethane; at 0 - 20 ℃; for 15h; Inert atmosphere;
64%
With triethylamine; In benzene; at 20 - 30 ℃; for 0.5h;
62%
With triethylamine; In dichloromethane; at 0 - 20 ℃; for 15h; Inert atmosphere;
57%
With triethylamine; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;
N-chloro-succinimide; para-thiocresol; In toluene; at 25 ℃; for 0.75h; Inert atmosphere;
With triethylamine; In toluene; at 25 ℃; for 12h; Inert atmosphere;
With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2.16667h; Inert atmosphere;
In dichloromethane; at 0 ℃; for 2.25h; Inert atmosphere;
para-thiocresol
106-45-6

para-thiocresol

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione
39549-10-5

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione

Conditions
Conditions Yield
para-thiocresol; With sulfuryl dichloride; triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
Succinimide; With triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
93%
para-thiocresol; With sulfuryl dichloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 1.25h; Inert atmosphere;
Succinimide; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h;
93%
para-thiocresol; With sulfuryl dichloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2.5h;
Succinimide; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;
45%
para-thiocresol; With sulfuryl dichloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 0.75h;
Succinimide; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h;
para-thiocresol; With sulfuryl dichloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2.5h;
Succinimide; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

para-bromotoluene
106-38-7

para-bromotoluene

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione
39549-10-5

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione

Conditions
Conditions Yield
With diammonium sulfide; 2-Methylpiperidin; In dimethyl sulfoxide; at 20 - 90 ℃; for 12h; Reagent/catalyst; Solvent; Catalytic behavior; Inert atmosphere;
98.6%
N-chloro-succinimide
128-09-6

N-chloro-succinimide

thiophenol
108-98-5

thiophenol

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione
39549-10-5

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione

Conditions
Conditions Yield
N-chloro-succinimide; thiophenol; In toluene; at 20 ℃; for 0.75h;
With triethylamine; In toluene; at 20 ℃; for 0.666667h;
62%
N-chloro-succinimide
128-09-6

N-chloro-succinimide

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

p-methylbenzenesulfenyl chloride
933-00-6

p-methylbenzenesulfenyl chloride

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione
39549-10-5

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione

Conditions
Conditions Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In dichloromethane; at 20 ℃; for 2h;
para-thiocresol
106-45-6

para-thiocresol

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione
39549-10-5

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: FeCl3 / acetone; H2O / Heating
2: 24 percent / benzene / 0.25 h / Heating
With iron(III) chloride; In water; acetone; benzene;
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione
39549-10-5

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione

Conditions
Conditions Yield
In benzene; for 0.25h; Heating;
24%
4-methylphenyl methylsulfide
623-13-2

4-methylphenyl methylsulfide

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione
39549-10-5

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione

Conditions
Conditions Yield
With tetrachloromethane; N-Bromosuccinimide;
1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione
39549-10-5

1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione

Conditions
Conditions Yield
Trimethylsilylimid (5), p-CH3-Ph-S-Cl;
N-Chlor-succinimid, Bis-(p-tolyl)-disulfid;
N-Chlorsuccinimid, Bis-(p-tolyl)-disulfid;
Succinimid (5), entspr. Sulfenylchlorid;
N-Chlorsuccinimid, p-Thiokresol;
Di-p-tolyl-disulfid, N-Brom-succinimid, Benzoylperoxid, neben p-Tolyl-sulfenylbromid;

Global suppliers and manufacturers

Global( 2) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
  • GIHI CHEMICALS CO.,LIMITED
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-571-86217390
  • Emails:info@gihichem.com
  • Main Products:66
  • Country:China (Mainland)
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