Name: 183267-04-1|1-(Trifluoromethylthio)pyrrolidine-2,5-dione|95%
Brand: Ambeed
SKU: A986831
Rating: 94 (40 reviews)

1
[ 173681-56-6 ]
[ 183267-04-1 ]
[ 1584705-63-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

2
[ 5957-89-1 ]
[ 183267-04-1 ]
[ 1584705-68-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

3
[ 183267-04-1 ]
[ 524713-66-4 ]
[ 1584705-58-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

4
[ 4385-61-9 ]
[ 183267-04-1 ]
[ 1584705-61-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

5
[ 5957-90-4 ]
[ 183267-04-1 ]
[ 1584705-60-1 ]

Yield	Reaction Conditions	Operation in experiment
59%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

6
[ 27012-22-2 ]
1-((trifluoromethyl)thio)pyrrolidine-2,5-dione [ No CAS ]
[ 1584705-65-6 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2046 - 2049

7
[ 46181-30-0 ]
1-((trifluoromethyl)thio)pyrrolidine-2,5-dione [ No CAS ]
[ 1584705-64-5 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2046 - 2049

8
[ 4467-06-5 ]
[ 183267-04-1 ]
[ 1584705-59-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

9
[ 10273-89-9 ]
[ 183267-04-1 ]
[ 1584705-67-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

10
[ 4373-61-9 ]
[ 183267-04-1 ]
[ 1584705-69-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

11
[ 4373-58-4 ]
[ 183267-04-1 ]
[ 1584705-70-3 ]

Yield	Reaction Conditions	Operation in experiment
61%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

12
[ 7431-45-0 ]
1-((trifluoromethyl)thio)pyrrolidine-2,5-dione [ No CAS ]
[ 1584705-66-7 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2046 - 2049

13
[ 66318-88-5 ]
[ 183267-04-1 ]
[ 1584705-75-8 ]

Yield	Reaction Conditions	Operation in experiment
69%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

14
[ 230-27-3 ]
[ 183267-04-1 ]
[ 1584705-56-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

15
[ 1008-89-5 ]
[ 183267-04-1 ]
[ 1584705-57-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium diacetate; acetic acid at 110℃; for 24h; Inert atmosphere; Sealed tube;
63%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Kovács, Szabolcs; Bayarmagnai, Bilguun; Goossen, Lukas J. [Advanced Synthesis and Catalysis, 2017, vol. 359, # 2, p. 250 - 254]
[2]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

16
[ 76759-26-7 ]
[ 183267-04-1 ]
[ 1584705-74-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With Pd(OTf)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>4</SUB> In acetic acid at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Xu, Chunfa; Shen, Qilong [Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049]

17
[ 52466-50-9 ]
[ 183267-04-1 ]
[ 2080748-97-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With C₃₈H₄₆N₄O₁₂ In dichloromethane at -10℃; for 72h; stereoselective reaction;

Reference： [1]Zhao, Bo-Liang; Du, Da-Ming [Organic Letters, 2017, vol. 19, # 5, p. 1036 - 1039]

18
[ CAS Unavailable ]
[ 183267-04-1 ]
[ 175400-81-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium decatungstate In acetonitrile at 20℃; for 18h; Inert atmosphere; Irradiation;	8 Synthesis of S-(trifluoromethyl) thiobenzoate (3a) In a dry 10 mL screw cap tube equipped with a magnetic stir bar, add 2c (0.2 mmol), NaDT (2 mol %),Aldehyde (0.30 mmol) followed by dry acetonitrile (2 mL) under nitrogen. The reaction mixture was allowed to stir at room temperature for 18 hours under illumination from a 40W LED. Et2O (30 mL) was then added, the resulting mixture was washed with water (3 x 30 mL), and the organic layer was dried over MgSO4. The solvent was removed by rotary evaporation in an ice bath and the resulting product was purified by flash chromatography on silica gel;Using petroleum ether (Rf=0.6) as eluent, the title compound 3a (42 mg) was obtained in 91%.
91%	With sodium decatungstate In acetonitrile at 20℃; for 18h; Inert atmosphere; Irradiation;	8 Synthesis of S-(trifluoromethyl) thiobenzoate (3a) In a dry 10 mL screw cap tube equipped with a magnetic stir bar, add 2c (0.2 mmol), NaDT (2 mol %),Aldehyde (0.30 mmol) followed by dry acetonitrile (2 mL) under nitrogen. The reaction mixture was allowed to stir at room temperature for 18 hours under illumination from a 40W LED. Et2O (30 mL) was then added, the resulting mixture was washed with water (3 x 30 mL), and the organic layer was dried over MgSO4. The solvent was removed by rotary evaporation in an ice bath and the resulting product was purified by flash chromatography on silica gel;Using petroleum ether (Rf=0.6) as eluent, the title compound 3a (42 mg) was obtained in 91%.
42 %Spectr.	With benzoic acid sodium salt; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In acetonitrile at 20℃; Inert atmosphere; Irradiation;

91 %Spectr.

With sodium decatungstate In acetonitrile at 20℃; for 18h; Inert atmosphere; Irradiation;

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN113860981, 2021, A Location in patent: Paragraph 0070-0074
[2]Current Patent Assignee: SHANDONG UNIVERSITY - CN113860981, 2021, A Location in patent: Paragraph 0070-0074
[3]Mukherjee, Satobhisha; Patra, Tuhin; Glorius, Frank [ACS Catalysis, 2018, vol. 8, # 7, p. 5842 - 5846]
[4]Ye, Zhegao; Lei, Ziran; Ye, Xiaodong; Zhou, Liejin; Wang, Yanan; Yuan, Zheliang; Gao, Feng; Britton, Robert [Journal of Organic Chemistry, 2022, vol. 87, # 1, p. 765 - 775]

19
[ 183267-04-1 ]
[ CAS Unavailable ]
[ 1927969-10-5 ]

Yield	Reaction Conditions	Operation in experiment
19 %Spectr.	With iron(III) chloride; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5h;

Reference： [1]Mao, Runze; Bera, Srikrishna; Cheseaux, Alexis; Hu, Xile [Chemical Science, 2019, vol. 10, # 41, p. 9555 - 9559]

20
[ 214907-25-2 ]
[ 183267-04-1 ]
[ 1401715-73-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With [2,2]bipyridinyl; copper(l) iodide; sodium carbonate In dimethyl sulfoxide at 60℃; Sealed tube;	4 Example 4: Synthesis of trans-4-methoxystyryl trifluoromethyl sulfide Accurately weigh styrylboronic acid (74mg, 0.5mmol), N-trifluoromethylthiosuccinimide (149mg, 0.75mmol), cuprous iodide (10mg, 0.05mmol), 2,2-bipyridine (8mg, 0.05mmol) and anhydrous sodium carbonate (210mg, 2.0mmol) in a dry and clean 50ml reaction tube, sealed after the completion of the ventilation operation. Add dimethyl sulfoxide solvent with a volume of 5ml into the reaction vessel and stir repeatedly for 8-12h at 60°C. After the reaction, it was cooled to room temperature, diluted with ethyl acetate and washed with distilled water and saturated sodium chloride solution, concentrated in vacuo and dried over anhydrous magnesium sulfate, concentrated again, and purified by column chromatography.70 mg of trans-4-methoxystyryl trifluoromethyl sulfide was obtained, and the yield was 60%

Reference： [1]Current Patent Assignee: JIANGNAN UNIVERSITY - CN112608260, 2021, A Location in patent: Paragraph 0054-0056

21
[ 516-12-1 ]
[ 1927969-10-5 ]
[ 183267-04-1 ]

Yield	Reaction Conditions	Operation in experiment
45%	With silver fluoride at 50℃; for 24h;	3 Example 3: In this example, N-iodosuccinimide and 4-phenylbenzoic acid trifluoromethyl thioester (S-(trifluoromethyl)[1,1'-biphenyl]-4-carbothioate) are used Reaction synthesis of the trifluoromethyl sulfide reagent: The synthesis steps and process are: add 4-phenylbenzoic acid trifluoromethyl thioester 3a (0.4 mmol, 112.8 mg) and silver fluoride (0.45 mmol, 57.2 mg) into a 10 mL reaction tube equipped with a magnetic stir bar. , 3.0 mL of acetonitrile, mix well and add N-iodosuccinimide 2c (0.4 mmol, 90.0 mg); fix the reaction tube on a magnetic stirrer, react at 50 for 24 hours, after completion, separate and purify to obtain the target Product 1, the yield is 45%.

Reference： [1]Current Patent Assignee: SHANDONG LINGHAI BIO TECH - CN112778190, 2021, A Location in patent: Paragraph 0016

22
[ 128-08-5 ]
[ 1927969-10-5 ]
[ 183267-04-1 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium fluoride; 18-crown-6 ether at 30℃; for 6h;	2; 6-9 Example 2: In this example, N-bromosuccinimide and 4-phenylbenzoic acid trifluoromethyl thioester (S-(trifluoromethyl)[1,1'-biphenyl]-4-carbothioate) are used Reaction synthesis of the trifluoromethyl sulfide reagent: The synthesis steps and process are: add 4-phenylbenzoic acid trifluoromethyl thioester 3a (0.4 mmol, 112.8 mg) and potassium fluoride (0.6 mmol, 34.8 mg) into a 10 mL reaction tube equipped with a magnetic stir bar. , 18-crown ether-6 (1.0 mmol, 264 mg), 4.0 mL benzotrifluoride, N-bromosuccinimide 2b (0.45 mmol, 80.1 mg); fix the reaction tube on a magnetic stirrer, The reaction was conducted at 30°C for 6 hours, and the target product 1 was obtained by separation and purification after completion, with a yield of 58%.

Reference： [1]Current Patent Assignee: SHANDONG LINGHAI BIO TECH - CN112778190, 2021, A Location in patent: Paragraph 0015; 0019-0022

23
[ 128-08-5 ]
[ 1927969-09-2 ]
[ 183267-04-1 ]

Yield	Reaction Conditions	Operation in experiment
32%	With tetramethylammonium fluoride In 1,4-dioxane at 25℃; for 18h;	4 Example 4: In this example, N-bromosuccinimide was used to react with trifluoromethyl 4-(tert-butyl)benzothioate to synthesize the three Fluoromethyl curing reagent: The synthesis steps and process are: add p-tert-butyl benzoic acid trifluoromethyl thioester 3b (0.4 mmol, 104.8 mg), tetramethylammonium fluoride (0.5 mmol, 46.6 mg), 3.0 mL 1,4 dioxane, N-bromosuccinimide 2b (0.4 mmol, 71.2 mg); fix the reaction tube on a magnetic stirrer, and react at 25°C for 18 hours. After separation and purification, the target product 1 was obtained with a yield of 32%.

Reference： [1]Current Patent Assignee: SHANDONG LINGHAI BIO TECH - CN112778190, 2021, A Location in patent: Paragraph 0017

24
[ 128-08-5 ]
(S-(trifluoromethyl)dodecanethioate) [ No CAS ]
1-((trifluoromethyl)thio)pyrrolidine-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With silver fluoride In acetonitrile at 40℃; for 24h;	5 Example 5: In this example, the trifluoromethyl sulfide reagent was synthesized by the reaction of N-bromosuccinimide and S-(trifluoromethyl) dodecanethioate: The synthesis steps and process are: add dodecanoic acid trifluoromethyl thioester 3c (0.4 mmol, 113.6 mg), silver fluoride (0.5 mmol, 63.5 mg), 3.0 mL acetonitrile into a 10 mL reaction tube equipped with a magnetic stir bar After mixing, add N-bromosuccinimide 2b (0.4 mmol, 71.2 mg); fix the reaction tube on a magnetic stirrer and react at 40°C for 24 hours. After the completion of separation and purification, the target product 1 is obtained. The rate is 70%.

Reference： [1]Current Patent Assignee: SHANDONG LINGHAI BIO TECH - CN112778190, 2021, A Location in patent: Paragraph 0017

25
[ 128-09-6 ]
[ 1927969-10-5 ]
[ 183267-04-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetrabutyl ammonium fluoride In acetonitrile at 25℃; for 12h;	1 Example 1: In this example, N-chlorosuccinimide and 4-phenylbenzoic acid trifluoromethyl thioester (S-(trifluoromethyl)[1,1'-biphenyl]-4-carbothioate) are used Reaction synthesis of the trifluoromethane sulfide reagent: The synthesis steps and process are: add 4-phenylbenzoic acid trifluoromethyl thioester 3a (0.4 mmol, 112.8 mg), tetrabutylammonium fluoride (0.5 mmol, 130.5) into a 10 mL reaction tube equipped with a magnetic stirrer. mg), 3.5 mL acetonitrile, mix well and add N-chlorosuccinimide 2a (0.4 mmol, 53.4 mg); fix the reaction tube on a magnetic stirrer, react at 25°C for 12 hours, and separate and purify after completion The target product 1 was obtained with a yield of 62%.

Reference： [1]Current Patent Assignee: SHANDONG LINGHAI BIO TECH - CN112778190, 2021, A Location in patent: Paragraph 0013-0014

26
[ CAS Unavailable ]
[ 183267-04-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
39%	With [2,2]bipyridinyl; copper (I) iodide; anhydrous sodium carbonate In acetonitrile at 60℃; for 24h; Inert atmosphere; stereospecific reaction;	(II) General procedure for copper(I)-Promoted Triuoromethylthiolation of Styreneboronic acid with N-trifluoromethylthiosuccinimide General procedure: To a 25 mL flask charged with aryl vinyl boric acid (1.0 equiv, 0.3 mmol), N-trifluoromethylthiosuccinimide (1.5 equiv), CuI (10 mmol%), Na2CO3 (4.0 equiv) and bpy (20 mmol%) was slowly added CH3CN (5 mL) by syringe at room temperature under N2 atmosphere. The reaction mixture was stirred at 60 °C for 12 hours (monitored by TLC). After cooling to room temperature, the suspension was filtered through a short pad of celite and the adsorbent was washed with DCM (2×5 mL). Then the filtrate was further washed with water (10 mL) and saturated NaCl solution (10 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by silica gel flash column chromatography using EtOAc/PE (V/V = 1/15) as eluent to afford the products.