Name: 29364-29-2|Sodium 2-methyl-2-propanethiolate|98%
Brand: Ambeed
SKU: A453384
Price: 19.0 USD
Availability: InStock
Rating: 99 (26 reviews)

1
[ 29270-55-1 ]
[ 29364-29-2 ]
[ 60716-16-7 ]

Reference： [1]Tetrahedron,1976,vol. 32,p. 1037 - 1040

2
(E/Z)-crotyl bromide [ No CAS ]
[ 29364-29-2 ]
[ 32931-15-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	In methanol at 0℃; for 3h;

Reference： [1]Binns, Malcolm R.; Haynes, Richard K.; Katsifis, Andrew G.; Schober, Paul A.; Vonwiller, Simone C. [Journal of the American Chemical Society, 1988, vol. 110, # 16, p. 5411 - 5423]

3
[ 57253-30-2 ]
[ 29364-29-2 ]
[ 114652-46-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	In methanol at 0℃;

Reference： [1]Haynes, Richard K.; Katsifis, Andrew G.; Vonwiller, Simone C.; Hambley, Trevor W. [Journal of the American Chemical Society, 1988, vol. 110, # 16, p. 5423 - 5433]

4
[ 1015-45-8 ]
[ 29364-29-2 ]
[ 131791-38-3 ]

Yield	Reaction Conditions	Operation in experiment
79%	In ethanol at 20℃; for 15h;

Reference： [1]Adam, Waldemar; Heil, Markus [Journal of the American Chemical Society, 1991, vol. 113, # 5, p. 1730 - 1736]

5
[ 57253-29-9 ]
[ 29364-29-2 ]
[ 114652-47-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	In methanol at 0℃;

Reference： [1]Haynes, Richard K.; Katsifis, Andrew G.; Vonwiller, Simone C.; Hambley, Trevor W. [Journal of the American Chemical Society, 1988, vol. 110, # 16, p. 5423 - 5433]

6
[ 29364-29-2 ]
[ 158775-23-6 ]
(3aR,5S,6S,6aR)-5-((2R,4R)-2-tert-Butylsulfanylmethyl-2-methyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 85℃; for 8h;

Reference： [1]Duhamel, Pierre; Ple, Gerard; Valnot, Jean-Yves [Heterocycles, 1994, vol. 37, # 2, p. 751 - 758]

7
[ 29364-29-2 ]
[ 158775-22-5 ]
(3aR,5S,6S,6aR)-5-((2S,4R)-2-tert-Butylsulfanylmethyl-2-methyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 85℃; for 8h;

Reference： [1]Duhamel, Pierre; Ple, Gerard; Valnot, Jean-Yves [Heterocycles, 1994, vol. 37, # 2, p. 751 - 758]

8
[ 29364-29-2 ]
[ 39824-26-5 ]
[ 128708-97-4 ]

Yield	Reaction Conditions	Operation in experiment
81.6%	In ethanol; N,N-dimethyl-formamide for 0.5h;

Reference： [1]Kappler, Francis; Hampton, Alexander [Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2545 - 2551]

9
[ 75-66-1 ]
[ 29364-29-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In diethyl ether at 0℃;
	With sodium hydroxide In methanol at 20℃; for 0.333333h;	3.B Method B; [0115] To a solution of sodium hydroxide (120 mg, 3 mmol, in oil, 60% cont.) in anhydrous methanol (5 ml) was added tert-butyl mercaptan (0.406 ml). The mixture was stirred for 20 minutes at room temperature. The reaction mixture was concentrated dryness under reduced pressure. The obtained sodium isopropylmercaptan was dissolved in HMPT (2 ml). 1,3,5-trichlorobenzene (1) (1.8 g, 10 mmol) was added thereto. The mixture was stirred for 2 hours and 50 minutes at 80[deg.] C. The reaction mixture was poured into ice-water. The mixture was extracted with ethylacetate, washed with water, dried over sodium sulphate, filtrated and concentrated under reduced pressure. The obtained residue was chromatographed twice on silica gel (SiO2 15 g, elution: n-hexane) to yield the objective (4) (293 mg). Yield 41%.
	With sodium

	With sodium hydride In tetrahydrofuran; mineral oil
	With sodium hydride In tetrahydrofuran

Reference： [1]Shi; Linden; Heimgartner [Helvetica Chimica Acta, 1994, vol. 77, # 7, p. 1903 - 1920]
[2]Current Patent Assignee: SHIONOGI & CO., LTD. - US2003/195363, 2003, A1 Location in patent: Page/Page column 8
[3]Lee, Sang Hyup [Bulletin of the Korean Chemical Society, 2013, vol. 34, # 1, p. 121 - 127]
[4]Chan, Ka-Wang; Ng, Wai-Ming; Cheung, Wai-Man; Lai, Chun-Sing; Sung, Herman H.Y.; Williams, Ian D.; Leung, Wa-Hung [Journal of Organometallic Chemistry, 2016, vol. 812, p. 151 - 157]
[5]Cappellani, E. Paul; Drouin, Samantha D.; Golombek, Adina; Maltby, Patricia A.; Morris, Robert H.; Rennie, Benjamin E.; Schweitzer, Caroline T. [Inorganica Chimica Acta, 2021, vol. 516]

10
[ 20027-95-6 ]
[ 29364-29-2 ]
2,6-Dimethyl-1,5-bis(2-methyl-2-propylthio)naphthalene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 97 - 102

11
[ 29364-29-2 ]
[ 75-28-5 ]

Yield	Reaction Conditions	Operation in experiment
	With (C5H4Me)2Mo2Co2(μ3-S)2(μ4-S)(CO)4 In acetonitrile at 80℃; for 2.5h;

Reference： [1]Druker, Scott H.; Curtis, M. David [Journal of the American Chemical Society, 1995, vol. 117, # 23, p. 6366 - 6367]

12
[ 29364-29-2 ]
[ 176199-35-2 ]
(R)-2-tert-Butoxycarbonylamino-3-(4-tert-butylsulfanyl-phenyl)-propionic acid [ No CAS ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 1431 - 1440
[2]Synthetic Communications,1996,vol. 26,p. 1431 - 1440

13
[ 29364-29-2 ]
[ 55758-02-6 ]
[ 178811-40-0 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 3617 - 3618

14
[ 29364-29-2 ]
[ 78846-88-5 ]
[ 460720-21-2 ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 650,p. 43 - 56

15
[ 32768-54-0 ]
[ 29364-29-2 ]
[ 943601-93-2 ]

Reference： [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 2743 - 2749

16
[ 6574-97-6 ]
[ 29364-29-2 ]
[ 880877-36-1 ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 3479 - 3489
[2]Journal of Organometallic Chemistry,2007,vol. 692,p. 2743 - 2749
[3]Journal of Organometallic Chemistry,2007,vol. 692,p. 2750 - 2760

17
[ 6574-99-8 ]
[ 29364-29-2 ]
[ 942057-34-3 ]

Reference： [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 2743 - 2749

18
[ 29364-29-2 ]
[ 312638-89-4 ]
[ 455954-58-2 ]

Yield	Reaction Conditions	Operation in experiment
	In DMF (N,N-dimethyl-formamide) at 20℃; for 18h;	1 4-Cyclohexyl-4-(isopropylthiomethyl)piperidine trifluoroacetate To a stirred solution of Intermediate 1d (4 mmol) in DMF (25 mL) at rt was added sodium 2-methyl-2-propanethiolate (2 g, 20 mmol). The resultant suspension was stirred at rt for 18 hr then poured into water (75 mL) and extracted with EtOAc (275 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. Chromatography over silica eluting with 5:95 EtOAc/hexane furnished the N-protected product as a clear colourless oil.
	In DMF (N,N-dimethyl-formamide) at 20 - 60℃; for 18h;	O.A PIPERIDINE INTERMEDIATES 17-21; Scheme O; Step A To a stirred solution of tert-butyl 4-cyclohexyl-4- { [(methylsulfonyl) oxy] methyl} [PIPERIDINE-L-CARBOXYLATE O-1)] (3 g, 8.0 mmol) in DMF (30 [ML)] at room temperature was added sodium 2-methyl-2-propanethiolate (0.78 g, 8.0 [MMOL).] The resultant suspension was stirred at [60°C] for 18 h and then poured into water (150 mL) and extracted with diethyl ether (3 x 100 mL). The combined organic extracts were washed with brine, dried over [NA2S04] and concentrated. Flash chromatography over silica (5% EtOAc in hexane) yielded [0-2] (W = iPr) as a clear colorless oil (2.4 g). ES-MS: calcd for C21H37NO2S : 355.25 ; Found: 378 [(MS +] Na).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US6350760, 2002, B1 Location in patent: Page column 49-50
[2]Current Patent Assignee: MERCK & CO INC - WO2004/24720, 2004, A1 Location in patent: Page 62

19
[ 29364-29-2 ]
[ 365996-28-7 ]
[ 865469-29-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	In DMF (N,N-dimethyl-formamide) at 70℃; for 3h;	397.D A 250 mL-flask was charged with mesylate 397d (3.0 g) and t-butylthiol sodium salt (3.44 g). The flask was flushed with nitrogen and 100 mL of dry DMF were added. The resulting solution was degassed (vacuum/nitrogen- flush) and heated to 70 °C. The flow of the reaction was monitored by TLC (ethyl acetate/hexanes; 2: 8). All the starting material was consumed in about 3 h. The reaction mixture was dissolved in 300 mL of ethyl acetate and washed with water (3 x 50 mL) and brine (1 x 50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated. No further purification was done for the product 397e (2.78 g; 95 %).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2005/87731, 2005, A1 Location in patent: Page/Page column 322-323

20
C₁₃H₂₄O₅S [ No CAS ]
[ 29364-29-2 ]
[ 865469-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₁₃H₂₄O₅S; sodium tert-butyl thiolate In DMF (N,N-dimethyl-formamide) at 20℃; Stage #2: With hydrogenchloride In DMF (N,N-dimethyl-formamide); water; ethyl acetate	621.5 Step 5 The residue from step 4 was dissolved in DMF (1 Oml) and sodium tert- butyl thiolate was added and the resulting reaction mixture was stirred at room temperature under an atmosphere of nitrogen overnight. The reaction mixture was partitioned between EtOAc and aq. 10% HCI. The organic phase was separated, washed with water (X4), dried (MgS04) and the volatiles removed under reduced pressure. The residue was purified by silica gel column chromatography using EtOAc-Hexanes (3: 7) as eluent to give the carboxylic acid (621 C ; 0.214g).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2005/87731, 2005, A1 Location in patent: Page/Page column 307

21
[ 1048697-25-1 ]
[ 29364-29-2 ]
C₄₁H₄₅N₅O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	In tetrahydrofuran at 65℃; for 16h;	136 Example 136: 3'-f 5-1( 1R)-1-amino-1-meth(at)phenylethyll-1,3,4-oxadiazol-2-yl 1-3-(tert-butylthio)-5'-( r(21-yn-l- ylpyrrolidin-l-yllcarbonyl} biphenyl-2-carbonitrile; To a solution containing 75 mg (0.12 mmol) of the fluoro nitrile (Intermediate LXIII) in 2.0 mL of THF was added 16 mg (0.14 mmol) of sodium tert-butylate. The reaction mixture was heated at 65°C for 16h before it was cooled, evaporated and subjected to reverse phase chromatography to give xx (? ) mg (36%) of the corresponding thiol derivative. This compound was dissolved in 3.0 mL of dichloromethane and cooled to 0°C. Trifluoroacetic acid (3.0 mL) was added and the resulting solution was stirred for 3 h. Evaporation of the solvent and reverse phase chromatography left the TFA salt of the desired compound. HRMS (M+H) = 604.2696. ¹H NMR (CD30D) 8 8.39 (s, 0.3H), 8.28 (s, 0.7H), 8.21 (s, 0.3H), 8.13 (s, 0.7H), 7.97 (s, 0.3H), 7.86 (s, 0.7H), 7.80 (m, 1H), 7.69 (d, J=7.5 Hz, 1H), 7.30-7.21 (m, 5H), 7.20 (d, J=7.5 Hz, 1H), 7.19-7.10 (m, 2H), 4.60 (bs, 1H), 3.67 (bt, 2H), 3.30 (s, 3H), 2.22-2.02 (m, 6H), 1.95 (s, 3H), 1.41 (s, 9H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2005/103020, 2005, A1 Location in patent: Page/Page column 165

22
[ 724788-78-7 ]
[ 29364-29-2 ]
[ 724788-79-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	In toluene at 60 - 70℃; for 21h;	15.e e) [4-[(1 ,1-dimethylethyl)thio]-5-([4-(methoxy)phenyl]methyl}oxy)-2-pyridinyl]methyl acetate; To a solution of (5-([4-(methoxy)phenyl]methyl}oxy)-4- [(trifluoromethyl)sulfonyl]oxy}-2-pyridinyl)methyl acetate (10 g, 23 mmol) in anhydrous toluene, (R)-(+)-2,2 bis(diphenylphosphino)-1 ,1-binaphthyl (312 mg, 0.4 mmol) was added. The reaction mixture was degassed before adding palladium acetate (103 mg, 0.4 mmol). Sodium 2-methyl-2-propanethiolate was added, the system degassed again and the reaction mixture was strirred at 6O0C for 3 hours, under argon atmosphere then at 70oC for a further 18 hours. The reaction mixture was filtered and the filtrate was evaporated under vacuum. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted several times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum. The residue was chromatographed on silica gel eluting with 20-35% ethyl acetate in hexane to afford the product as an oil (9.1 g, 100%); MS (+ve ion electrospray) m/z 376(MH+).
100%	In toluene at 60 - 70℃; for 18h;	9.e e) [4-[(1,1 -dimethylethyl)thio]-5-([4-(methoxy)phenyl]methyl}oxy)-2-pyridinyl]methylacetate; To a solution of (5-([4-(methoxy)phenyl]methyl}oxy)-4-[(trifluoromethyl)sulfonyljoxy}-2-pyridinyl)methyl acetate (10 g, 23 mmol) in anhydroustoluene, (R)-(+)-2,2 bis(diphenylphosphino)-1,1-binaphthyl (312 mg, 0.4 mmol) wasadded. The reaction mixture was degassed before adding palladium acetate (103 mg, 0.4mmol). Sodium 2-methyl-2-propanethiolate was added, the system degassed again andthe reaction mixture was stirred at 60°C for 3 hours, under argon atmosphere then at70oC for a further 18 hours. The reaction mixture was filtered and the filtrate wasevaporated under vacuum. The residue was partitioned between ethyl acetate and water.The aqueous layer was extracted several times with ethyl acetate. The combined organicextracts were dried over magnesium sulfate and evaporated under vacuum. The residuewas chromatographed on silica gel eluting with 20-35% ethyl acetate in hexane to affordthe product as an oil (9.1 g, 100%); MS (+ve ion electrospray) m/z 376(MH+).
100%	With palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In toluene at 60 - 70℃; for 21h;

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2006/2047, 2006, A2 Location in patent: Page/Page column 91
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2006/14580, 2006, A1 Location in patent: Page/Page column 42
[3]Location in patent: scheme or table Barfoot, Christopher W.; Brown, Pamela; Dabbs, Steven; Davies, David T.; Hennessy, Alan J.; Miles, Timothy J.; Pearson, Neil D. [Tetrahedron Letters, 2010, vol. 51, # 38, p. 5038 - 5040]

23
concentrated acetic acid [ No CAS ]
3-[(2-chloro)propionyl]-6-methoxyphenylaceticacid [ No CAS ]
methanol-CH₂ Cl₂ [ No CAS ]
diethyl ether-CH₂ Cl₂ [ No CAS ]
[ 107-47-1 ]
[ 29364-29-2 ]
[ 7669-54-7 ]
[ 33513-42-7 ]
[ 167764-30-9 ]

Yield	Reaction Conditions	Operation in experiment
59%	With hydrogenchloride In tetrahydrofuran; diethyl ether; dichloromethane; water	4 Preparation of 3-[2-[(2-Nitrophenyl)dithio]propionyl]-6-methoxyphenylacetic acid (5). EXAMPLE 4 Preparation of 3-[2-[(2-Nitrophenyl)dithio]propionyl]-6-methoxyphenylacetic acid (5). To a 50 mL round bottom flask containing 0.9 grams (8.82 mmole) of the sodium salt of 2-methyl-2-propanethiol was added 0.25 grams of sodium hydride (11.3 mmole) and the resulting mixture placed under vacuum and then under a nitrogen atmosphere. To the mixture was then added 15 mL of anhydrous tetrahydrofuran and the mixture cooled to 0° C. To the cooled mixture was added 1.5 grams (5.84 mmole) of 9 dissolved in 15 mL of anhydrous THF over a period of 10 minutes. After addition, the reaction mixture was allowed to stir, at room temperature and under a nitrogen atmosphere for 18 hours. After 18 hours the volatile components of the reaction mixture were removed under reduced pressure to give a brown solid. The brown solid was dissolved in 80 mL of H2 O and aqueous washed with 100 mL of diethyl ether. The aqueous layer was then acidified with 1 mL of concentrated HCl (pH=1) and then extracted (2100 mL) with diethyl ether and organic layers combined, dried over MgSO4, filtered and volatile components removed under reduced pressure to give 1.75 grams of the t-butyl thioether product which was used without any further purification. To a 25 mL round bottom flask containing 1.75 grams (5.64 mmole) of the crude t-butyl thioether was added 2 mL of dimethyl formamide, 4 mL of concentrated acetic acid and 1 mL of H2 O and mixture sonicated until the solution was complete. To the solution was then added 1.6 grams (8.44 mmole) of 2-nitrobenzenesulfenyl chloride and mixture stirred, in the dark, for 24 hours. After 24 hours, the volatile components of the reaction mixture were removed under reduced pressure to give an oil/water mixture. To the mixture was then added 15 mL of H2 O, cooled to freezing and then lyophilized overnight. After lyophilization, the remaining solid was taken up in CH2 Cl2 and purified by flash chromatography (SiO2, 3.517 cm column) first with CH2 Cl2, then with 50% diethyl ether-CH2 Cl2 and then with 10% methanol-CH2 Cl2 to isolate a yellow oil which crystallized upon standing to give 1.41 grams (59% yield) of 5 as a yellow crystalline solid.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US5502246, 1996, A

24
[ 381675-07-6 ]
[ 29364-29-2 ]
2-(4-tert-Butylsulfanyl-phenyl)-2,3-dihydro-phthalazine-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With copper(l) iodide; ethylene glycol In 1-methyl-pyrrolidin-2-one at 150℃; for 96h;	ZA.1 Method ZA - sulfanyl substituted 2-phenylphthalazinones from 2-(iodophenyl)phthalazinonesExample ZA-I: 2-[4-(2-Methyl-propane-2-sulfonylVpheixyll-4-(5-methyl-lH- p yr azol- 3 - ylamino ) -2H -phthalazin- 1 - one2-(4-tert-Butylsulfanyl-phenyl)-2,3-dihydro-phthalazine-l,4-dione4-Hydroxy-2-(4-iodophenyl)-2H-phthalazin-l-one (see Method Q) (0.3Og, O.δmmol), sodium 2-methyl-propane-2-thiolate (0.094g, O.δmmol), CuI (0.01 Ig, O.Ommol) and ethylene glycol (O.lOg, l.mmol) were dissolved in N-methyl- pyrrolidinone (NMP) (0.5ml) under argon and heated to 1500C. Stirring at this temperature was continued for 4 d before the mixture "was allowed to warm to room temperature. H2O (50ml) was added and the precipitated solid was collected by filtration. The title compound was obtained after purification of the raw product by chromatography over silica gel with dichloromethane (O.21g, 78%).1H-NMR: (400 MHz, D6-DMSO) 12.35 (IH, s), 8.73 (IH, d), 8.33-8.41 (3H, m), 8.14 (2H, d), 8.01 (2H, d), 1.70 (9H, s); MS (ESI+) = 327.14 (M+H)+.
78%	With copper(l) iodide; ethylene glycol In 1-methyl-pyrrolidin-2-one at 150℃; for 96h;	ZA-1 2-(4-tert-Butylsulfanyl-phenyl)-2,3-dihydro-phthalazine-1,4-dione: 4-Hydroxy-2-(4-iodo-phenyl)-2H-phthalazin-1-one (see Method Q) (0.30 g, 0.8 mmol), sodium 2-methyl-propane-2-thiolate (0.094 g, 0.8 mmol), CuI (0.011 g, 0.06 mmol) and ethylene glycol (0.10 g, 1.6 mmol) were dissolved in N-methyl-pyrrolidinone (NMP) (0.5 ml) under argon and heated to 150° C. Stirring at this temperature was continued for 4 d before the mixture was allowed to warm to RT. H2O (50 ml) was added and the precipitated solid was collected by filtration. The title compound was obtained after purification of the raw product by chromatography over silica gel with DCM (0.21 g, 78%). 1H-NMR: (400 MHz, D6-DMSO) 12.35 (1H, s), 8.73 (1H, d), 8.33-8.41 (3H, m), 8.14 (2H, d), 8.01 (2H, d), 1.70 (9H, s); MS (ESI+)=327.14 (M+H)+.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2006/32518, 2006, A1 Location in patent: Page/Page column 206
[2]Current Patent Assignee: ROCHE HOLDING AG - US2007/219195, 2007, A1 Location in patent: Page/Page column 58

25
1-(1-acetylpyrazol-3-yl)-6,6-dimethyl-3-methanesulphinyl-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one [ No CAS ]
[ 29364-29-2 ]
6,6-dimethyl-3-[(1,1-dimethylethyl)thio]-1-(pyrazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	In tetrahydrofuran	23 6,6-dimethyl-3-[(1,1-dimethylethyl)thio]-1-(pyrazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one EXAMPLE 23 6,6-dimethyl-3-[(1,1-dimethylethyl)thio]-1-(pyrazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one To a stirred solution of 1-(1-acetylpyrazol-3-yl)-6,6-dimethyl-3-methanesulphinyl-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (73 mg, 0.21 mmol) in THF (7 mL) was added sodium 2-methyl-2-propanethiolate (47 mg, 0.42 mmol). After 90 min more sodium 2-methyl-2-propanethiolate (15 mg, 0.14 mmol) was added, and after a further 30 min the mixture was partitioned between EtOAc (15 mL) and water (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluding with petrol:EtOAc (1:1), to give the title compound (34 mg, 48%) as a yellow solid. mp 220-222° C. Found: C, 60.67; H, 6.39; N, 8.31%. C17H22N2OS2 requires: C, 61.04; H, 6.63; N, 8.37%. 1NHMR (360 Hz, d6-DMSO)δ 1.00 (6H, s), 1.45 (9H, s), 2.39 (2H, s), 2.88 (2H, s), 6.54 (1H, br s), 7.87 (1H, br s), 13.07 (1H, br s). MS (ES+) 335 (M+1).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US6262103, 2001, B1

26
[ 29364-29-2 ]
[ 943026-54-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: (4-[(phenylmethyl)oxy]-5-[(trifluoromethyl)sulfonyl]oxy}-2-pyridinyl)methyl acetate With (R)-(+)-2,2’-bis(diphenylphosphino)-1,1’-binaphthalene In toluene for 0.166667h; Stage #2: sodium tert-butyl thiolate In toluene at 80℃; for 7h;	23A.d (d) (5-[(l,l-Dimethylethyl)thio]-4-[(phenyhnethyl)oxy]-2-pyridinyl}methyl acetate • To a solution of (4-[(phenylmethyl)oxy]-5-[(trifluoromethyl)sulfonyl]oxy}-2- pyridinyl)methyl acetate (12.15g, 30 mmol) in toluene (500 ml) was added (R)-(+)- 2,2'-bis(diphenylphosptano)-l,r-binaphtliyl (1.87g, 3 mmol). The reaction mixture was purged with argon. Palladium acetate (663mg, 3mmol) was added and the mixture was stirred for 10 minutes. 2-Methyl-2-propanethiol sodium salt (4.69, 41.8 mmol) was added and the reaction mixture was flushed again with argon then heated to 8O0C for 7 hours then cooled. The solvent was evaporated. The residue was partitioned between a 1 : 1 mixture of water and EtOAc. The organic layer was separted and washed with brine, dried over magnesium sulphate and filtered through Kieselguhr. The residue was chromatographed eluting with s 4:1 mixture of hexane:EtOAc affording the product (8.3g, 80%). MS (+ve ion electrospray) m/z 346 (MH+).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2007/71936, 2007, A1 Location in patent: Page/Page column 63-64

27
[ 14508-49-7 ]
[ 29364-29-2 ]
[ 70170-22-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	In tetrahydrofuran; water; ethyl acetate	P.5 2-(tert-Butylthio) pyrazine Production Example 5 2-(tert-Butylthio) pyrazine After dissolving 2.305 g of 2-chloropyrazine in 60 ml of tetrahydrofuran, 2.76 g of sodium tert-butylthiolate was added while stirring and the mixture was heated to reflux for 3 hours. Water was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue and filtration was performed with NH silica gel and silica gel. The solvent was distilled off under reduced pressure to obtain the title compound (3.217 A, 95% yield). 1H-NMR (400MHz, CDCl3); δ (ppm) 1.54 (9H, s), 8.28 (1H, d, J=2.8 Hz), 8.44 (1H, dd, J=2.8, 1.6 Hz), 8.50 (1H, d, J=1.6 Hz).

Reference： [1]Current Patent Assignee: EISAI CO LTD - US2004/167224, 2004, A1

28
[ 33100-27-5 ]
[ 50960-82-2 ]
[ 29364-29-2 ]
[ 172702-24-8 ]
[Na(15-crown-5)]2[Au₄Cl₆S₂] [ No CAS ]
[Na(15-crown-5)]4[AuCl₂]2[Au₄Cl₆S₂] [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1995,p. 3917 - 3924

29
[Na(THF)1.5][Cp*2UCl₂] [ No CAS ]
[ 29364-29-2 ]
Na[Cp*2U(StBu)(S)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With Na#Hg In tetrahydrofuran byproducts: isobutane, isobutylene; stirring at 20°C for 18 h, filtration, evapn.; extn. (pentane);
95%	In tetrahydrofuran under Ar atm. (Na(THF)1.5)(Cp*2UCl2), NaStBu, and THF were stirred for 18 h at 20°C; soln. was filtered and evapd. to dryness, residue was extd. in pentane, solvent was evapd.;

Reference： [1]Ventelon, Lionel; Lescop, Christophe; Arliguie, Therese; Leverd, Pascal C.; Lance, Monique; Nierlich, Martine; Ephritikhine, Michel [Chemical Communications, 1999, # 7, p. 659 - 660]
[2]Arliguie, Thérèse; Lescop, Christophe; Ventelon, Lionel; Leverd, Pascal C.; Thuéry, Pierre; Nierlich, Martine; Ephritikhine, Michel [Organometallics, 2001, vol. 20, # 17, p. 3698 - 3703]

30
[ 4249-10-9 ]
[ 29364-29-2 ]
iron(II) chloride [ No CAS ]
[ 212910-07-1 ]

Reference： [1]Inorganic Chemistry,1998,vol. 37,p. 4015 - 4021

31
[ 33100-27-5 ]
[ 50960-82-2 ]
[ 29364-29-2 ]
[ 172702-24-8 ]
[ 172702-23-7 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1995,p. 3917 - 3924

32
[ 26305-75-9 ]
[ 29364-29-2 ]
octa-μ(3)-thio-hexakis(triphenyphosphine)-octahedro-hexacobalt-triphenylphosphine-1,2-dichloroethane-water (1/2/2/1) [ No CAS ]

Reference： [1]Acta Crystallographica, Section C: Crystal Structure Communications,1995,vol. 51,p. 1275 - 1278

33
[ 29364-29-2 ]
[ 202533-73-1 ]
[ 1056250-05-5 ]

Yield	Reaction Conditions	Operation in experiment
76.4%	With pyridine at 20℃; for 16h;	2 Example 2 Synthesis of 5',3'-O-(Tetraisopropyldisiloxane-1,3-divl) 2'-O-t-butylthiocarbonyl (BSC) uridine 5',3'-O-(Tetraisopropyldisiloxane-1,3-diyl) 2'-O-(p-nitrophenyl)carbonate protected uridine (15 mmole) was coevaporated 3 times with pyridine, and then dried on vacuum pump for 4 hours. Anhydrous pyridine (150 mL) and sodium 2-methyl-2-propanethiolate (24 mmole) were added, and the mixture was stirred at room temperature for 16 hours. The product was purified by column chromatography using hexanes with a gradient of EtOAc (0-30%). Yield 76.4% ESI MS: 609 (M+Li), 637 (M+Cl)

Reference： [1]Current Patent Assignee: UNIVERSITY OF COLORADO (SYSTEM) - US2008/227964, 2008, A1 Location in patent: Page/Page column 19

34
[ 75-15-0 ]
[ 29364-29-2 ]
[ 2632-10-2 ]
[ 218795-37-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4746 - 4752

35
[ 724788-70-9 ]
[ 29364-29-2 ]
[ 1075260-22-8 ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: 8-bromo-7-fluoro-2-methoxy-1,5-naphthyridine In toluene for 0.166667h; Stage #2: sodium tert-butyl thiolate In toluene at 80℃; for 72h; Heating / reflux;	69.a Example 69; (6R)-6-({4-[(2,3-dihydro[l,4]dioxino[2,3-c]pyridin-7- ylmethyl)amino]-l-piperidinyl}methyl)-3-fluoro-5,6-dihydro-8H- [ 1 ,4] thiazino [2,3,4-de] - 1 ,5-naphthyridin-8-one dihydrochloride; (a) 8-[(l , 1 -Dimethylethyl)thio]-7-fluoro-2-(methyloxy)- 1 ,5-naphthyridine; A mixture of 8-bromo-7-fluoro-2-(methyloxy)-l,5-naphthyridine (for a synthesis see WO2004058144, Example 53(g)) (2.57g, 10 mmol) and (s)-(-)-tol- BINAP (620mg, 10 mol%) in toluene (170ml) was purged with argon, the flask evacuated and the procedure repeated three times. Palladium (II) acetate (220 mg) was added and the mixture stirred for 10 min. Solid sodium tert-butyl thyiolate (1.56g) was added and the flask purged with argon. The reaction mixture was heated to 8O0C for 24h , then refluxed for 2 days. The solvent was evaporated and the residue partitioned between water and ethyl acetate . The organic phase was washed with brine, dried (MgSO4) and evaporated. The residue was chromatographed on silica eluting with 0 - 100% ethyl acetate in hexane to afford the title compound as a pale yellow oil (1.58g, 59%). MS (ES+), m/z 267 (MH+, 40%).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2008/128953, 2008, A1 Location in patent: Page/Page column 67-68

36
[ 101333-46-4 ]
[ 29364-29-2 ]
[ 521278-08-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate In water for 2h;	36.A Example 36; Preparation of Interemdiate Compound 36G; Step A - Synthesis of Compound 36B; 36 A 36 B; To a stirred solution of aqueous HCl (15 mL of cone HCl in 50 mL of water) was added 3-amino-4-methyl benzoic acid (36 A, 5.0 g; 33.0 mmol). The mixture was cooled in an ice- water bath followed by slow addition of a solution of sodium nitrite (1.1 eq, 2.50 g) in water (12 mL). The mixture was stirred for 30 min at which point the mixture was a homogeneous dark solution. A saturated aqueous solution of sodium acetate was added until pH 6 was attained. Sodium t-butylthiolate (0.5 eq, 1.85 g) was added in one portion. The reaction was stirred for 2 h and the resulting precipitate was collected by filtration (whatman No.1), washed with water (20 mL) and dried under vacuum to give the product 36B (2.7 g; 64 %) as a tan solid.
	With sodium acetate In water for 2h;	17.A Example 17; Preparation of Interemdiate Compound 17G; Step A - Synthesis of Compound 17 B; 17A 17B; To a stirred solution of aqueous HCl (15 mL of cone HCl in 50 mL of water) was added 3-amino-4-methyl benzoic acid (17A, 5.0 g; 33.0 mmol). The mixture was cooled in an ice- water bath followed by slow addition of a solution of sodium nitrite (1.1 eq, 2.50 g) in water (12 mL). The mixture was stirred for 30 min at which point the mixture was a homogeneous dark solution. A saturated aqueous solution of sodium acetate was added until pH 6 was attained. Sodium t-butylthiolate (0.5 eq, 1.85 g) was added in one portion. The reaction was stirred for 2 h and the resulting precipitate was collected by filtration (whatman No.1), washed with water (20 mL) and dried under vacuum to give the product 17B (2.7 g; 64 %) as a tan solid.
	With sodium acetate In water for 2h;	19.A Example 19; Preparation of Interemdiate Compound 19G; Step A - Synthesis of Compound 19B; 19A 19B; To a stirred solution of aqueous HCl (15 mL of cone HCl in 50 mL of water) was added 3-amino-4-methyl benzoic acid (19A, 5.0 g; 33.0 mmol). The mixture was cooled in an ice- water bath followed by slow addition of a solution of sodium nitrite (1.1 eq, 2.50 g) in water (12 mL). The mixture was allowed to stir for 30 minutes at which point the mixture was a homogeneous dark solution. A saturated aqueous solution of sodium acetate was added until pH 6 was attained. Sodium t-butylthiolate (0.5 eq, 1.85 g) was added in one portion. The reaction was allowed to stir for 2 h and the resulting precipitate was collected by filtration (whatman No.1), washed with water (20 mL) and dried under vacuum to provide the product 19B (2.7 g; 64 %) as a tan solid.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/32123, 2009, A2 Location in patent: Page/Page column 171
[2]Current Patent Assignee: MERCK & CO INC - WO2009/32125, 2009, A1 Location in patent: Page/Page column 110-111
[3]Current Patent Assignee: MERCK & CO INC - WO2009/32124, 2009, A1 Location in patent: Page/Page column 185

37
[ 636-28-2 ]
[ 29364-29-2 ]
[ 1043877-63-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	In N,N-dimethyl-formamide at 50℃; for 5h; Inert atmosphere;

Reference： [1]Wang, Yongfeng; Parkin, Sean R.; Gierschner, Johannes; Watson, Mark D. [Organic Letters, 2008, vol. 10, # 15, p. 3307 - 3310]

38
[ 29364-29-2 ]
[ 149965-41-3 ]
[ 960409-48-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	In ethanol; for 15.0h;Reflux; Inert atmosphere;	To a solution of sodium tert-butyl thiolate (1.08 g, 9.64 mmol) in 42 ml of ethanol <strong>[149965-41-3]5-Bromo-2-chlorobenzyl bromide</strong> (2.74 g, 9.64 mmol) dissolved in 19 ml of ethanol was added and the mixture was brought to reflux under an atmosphere of argon for 15 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure and the residue was dissolved in ethylacetate and washed with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure, yielding 2.34 g (84%) of the desired product.

Reference： [1]Patent: US2009/203696,2009,A1 .Location in patent: Page/Page column 27

39
[ 110-52-1 ]
[ 29364-29-2 ]
[ 1119801-76-1 ]

Yield	Reaction Conditions	Operation in experiment
21%	In N,N-dimethyl-formamide at 70℃; for 23h;	21 4-Bromobutyl 1,1-dimethylethyl sulfide 4-Bromobutyl 1,1-dimethylethyl sulfide A solution of 1,4-dibromobutane (commercially available, for example, from Aldrich) (4.7 ml, 40 mmol) in DMF (10 ml) was treated with sodium 2-methyl-2-propanethiolate (commercially available, for example, from Aldrich) (3.36 g, 30 mmol) and the mixture was heated for 23 h at 70° C. The mixture was allowed to cool to room temperature, and partitioned between water and EtOAc. The organic solution was washed with water (*4), aqueous sodium bicarbonate solution, brine, dried (MgSO4), and evaporated. The residue was purified by flash column chromatography on silica (200 g) eluding with 0-50% EtOAc-cyclohexane to give the title compound (1.4 g, 21%): 1H NMR δ (CDCl3) 3.46 (2H, t, J=7 Hz), 2.96 (2H, t, J=7 Hz), 2.15-2.03 (4H, m), 1.44 (9H, s).
21%	In N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2009/270355, 2009, A1 Location in patent: Page/Page column 25
[2]Procopiou, Panayiotis A.; Ford, Alison J.; Gore, Paul M.; Hancock, Ashley P.; Hodgson, Simon T.; Holmes, Duncan S.; Looker, Brian E.; Vile, Sadie; Clark, Kenneth L.; Saunders, Ken A.; Slack, Robert J.; Watts, Clarissa J. [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4914 - 4919]

40
[ 29364-29-2 ]
[ 540-51-2 ]
[ 5396-50-9 ]

Yield	Reaction Conditions	Operation in experiment
9%	In N,N-dimethyl-formamide at 70 - 80℃;	11 Intermediate 112-[(1,1-Dimethylethyl)thio]ethanolA mixture of bromoethanol (commercially available, for example, from Avocado) (1.5 ml, 21 mmol) and sodium 2-methyl-2-propanethiolate (commercially available, for example, from Aldrich) (2.5 g, 22 mmol) in DMF (10 ml) were heated to 70° C. overnight. The mixture was cooled to room temperature, diluted with water and extracted with EtOAc (×2). The organic solution was washed with water, brine, dried (MgSO4), and evaporated under reduced pressure to give a mixture containing starting material and product by NMR (578 mg). This was re-dissolved in DMF (5 ml) and treated with sodium 2-methyl-2-propanethiolate (2.5 g, 22 mmol) and heated to 80° C. for 4 days. The mixture was cooled to room temperature, diluted with water and extracted with EtOAc (×2). The organic solution was washed with water (×5), brine, dried (MgSO4), and evaporated under reduced pressure to give the title compound (332 mg, 9%): 1H NMR δ (CDCl3) 3.73 (2H, t, J=6 Hz), 2.77 (2H, t, J=6 Hz), 2.19-2.07 (1H, br), 1.31 (9H, s).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2009/270355, 2009, A1 Location in patent: Page/Page column 23

41
[ 29364-29-2 ]
(+/-)-7-bromo-<5>-helicene [ No CAS ]
[ 1186023-04-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In butan-1-ol at 100℃; for 14h;

Reference： [1]Goretta, Sarah; Tasciotti, Christelle; Mathieu, Simon; Smet, Mario; Maes, Wouter; Chabre, Yoann M.; Dehaen, Wim; Giasson, Richard; Raimundo, Jean-Manuel; Henry, Claude R.; Barth, Clemens; Gingras, Marc [Organic Letters, 2009, vol. 11, # 17, p. 3846 - 3849]

42
[ 2458-12-0 ]
[ 29364-29-2 ]
[ 521278-08-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	Stage #1: 3-amino-p-toluic acid With hydrogenchloride; sodium nitrite In water for 0.5h; Stage #2: With sodium acetate In water Stage #3: sodium tert-butyl thiolate In water for 2h;	14.B To a stirred solution of aqueous HCl (15 niL of cone HCl in 50 mL of water) was added 3-amino~4-methyl benzoic acid (14 A, 5.0 g; 33.0 mmol). The mixture was cooled in an ice- water bath followed by slow addition of a solution of sodium nitrite (I.I eq, 2.50 g) in water (12 mL). The mixture was stirred for 30 min at which point the mixture was a homogeneous dark solution. A saturated aqueous solution of sodium acetate was added until pH 6 was attained. Sodium t-butylthiolate (0.5 eq, 1.85 g) was added in one portion. The reaction was stirred for 2 h and the resulting precipitate was collected by filtration (whatman No.1), washed with water (20 mL) and concentrated in vacuo to provide the product 14B (2.7 g; 64 %) as a tan solid.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/152200, 2009, A1 Location in patent: Page/Page column 81

43
[ 591-50-4 ]
[ 201230-82-2 ]
[ 29364-29-2 ]
[ 13291-44-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With bis-triphenylphosphine-palladium(II) chloride; 2-methylpropan-2-thiol In tetrahydrofuran at 70℃; for 24h; Autoclave;

Reference： [1]Hu, Yanhe; Liu, Jing; Lu, Zhixin; Luo, Xiancai; Zhang, Heng; Lan, Yu; Lei, Aiwen [Journal of the American Chemical Society, 2010, vol. 132, # 9, p. 3153 - 3158]

44
[ 637-87-6 ]
[ 201230-82-2 ]
[ 29364-29-2 ]
[ 1213298-45-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With bis-triphenylphosphine-palladium(II) chloride; 2-methylpropan-2-thiol In tetrahydrofuran at 70℃; for 24h; Autoclave;

Reference： [1]Hu, Yanhe; Liu, Jing; Lu, Zhixin; Luo, Xiancai; Zhang, Heng; Lan, Yu; Lei, Aiwen [Journal of the American Chemical Society, 2010, vol. 132, # 9, p. 3153 - 3158]

45
[ 583-55-1 ]
[ 201230-82-2 ]
[ 29364-29-2 ]
[ 1213298-46-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With bis-triphenylphosphine-palladium(II) chloride; 2-methylpropan-2-thiol In tetrahydrofuran at 70℃; for 24h; Autoclave;

Reference： [1]Hu, Yanhe; Liu, Jing; Lu, Zhixin; Luo, Xiancai; Zhang, Heng; Lan, Yu; Lei, Aiwen [Journal of the American Chemical Society, 2010, vol. 132, # 9, p. 3153 - 3158]

46
[ 201230-82-2 ]
[ 696-62-8 ]
[ 29364-29-2 ]
[ 96025-43-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	With bis-triphenylphosphine-palladium(II) chloride; 2-methylpropan-2-thiol In tetrahydrofuran at 120℃; for 12h; Autoclave;

Reference： [1]Hu, Yanhe; Liu, Jing; Lu, Zhixin; Luo, Xiancai; Zhang, Heng; Lan, Yu; Lei, Aiwen [Journal of the American Chemical Society, 2010, vol. 132, # 9, p. 3153 - 3158]

47
[ 29364-29-2 ]
[ 316808-11-4 ]
[ 1227255-00-6 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 3827 - 3832

48
[ 2402-78-0 ]
[ 29364-29-2 ]
[ 122733-89-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	In N,N-dimethyl-formamide at 80℃; for 12h;	91.A A suspension of sodium 2-methylpropane-2-thiolate (188 mg, 1.68 mmol) in DMF was treated with 2,6- dichloropyridine (4865 μl, 1.46 mmol) at ambient temperature in a vial. The vial was capped and heated to 80° C with rapid stirring of the colorless solution. After 12 hours, the reaction was cooled to ambient temperature and diluted with ethyl acetate. The ethyl acetate solution was washed with brine solution, dried with sodium sulfate, filtered, concentrated and purified on silica gel. Elution with 2% to 10% ethyl acetate/hexanes provided the title compound (271 mg, 1.34 mmol, 92.0 % yield) as a light yellow oil.

Reference： [1]Current Patent Assignee: PFIZER INC - WO2010/75200, 2010, A1 Location in patent: Page/Page column 115

49
[ 2613-27-6 ]
[ 29364-29-2 ]
[ 1272542-21-8 ]

Yield	Reaction Conditions	Operation in experiment
14%	In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
14%	In N,N-dimethyl-formamide at 20℃; for 1h;	13 -BuSNa (274 mg, 2.44 mmol, 3 eq.) was added in three minutes to a stirred solution of l-nitro-4-(pentafluorosulfanyl)benzene (1) (203 mg, 0.82 mmol, 1 eq.) in DMF (1.2 mL) at room temperature. After reaction time of one hour, saturated aqueous solution of NH4C1 (15 mL) and water (5 mL) were added and the product was extracted to Et20 (3 χ 20 mL). The combined organic phase was washed with saturated aqueous solution of NaCl (15 mL), dried with anhydrous MgS04 and solvent was removed under reduced pressure. Column chromatography using silica gel (Rf 0.52, hexane) gave a mixture of product 3m and t-BuSSBu-t as a colorless liquid (165 mg, corresponding to 33 mg of pure 3m, 14 mol. %). 1H NMR (400 MHz) 1.31 (s, 9H, C(CH3)3), 7.58-7.63 (m, 2H, CArH), 7.68-7.72 (m, 2Η, CMH); 19F NMR (376 MHz) 62.4 (d, 4F, 2JFF = 150.0 Hz, SF4), 82.7-84.3 (m, IF, SF); MS (EI) m/z 292 QJf, 13%), 236 (39), 127 (14), 83 (13), 57 (100), 41 (28)

Reference： [1]Beier, Petr; Pastyrikova, Tereza; Vida, Norbert; Iakobson, George [Organic Letters, 2011, vol. 13, # 6, p. 1466 - 1469]
[2]Current Patent Assignee: CZECH ACADEMY OF SCIENCES - WO2012/45290, 2012, A1 Location in patent: Page/Page column 17

50
[ 108-36-1 ]
[ 29364-29-2 ]
(3-bromophenyl)(tert-butyl)sulfane [ No CAS ]
[ 25752-96-9 ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one at 80℃; for 120h;	17 Preparation 17 1-bromo-3-[(1 ,1-dimethylethyl)sulfonyl]-5-methylbenzene1 ,3-dibromobenzene (1.023 mL, 8.48 mmol) was dissolved in N-Methyl-2-pyrrolidone (NMP) (20 mL) and t-butylthiol sodium salt (3.17 g, 25.4 mmol) was slowly added at room temperature. Reaction was slightly exothermic and turned medium pink/red color.Reaction was heated at 80°C for 5 days. Reaction was cooled to room temperature and 0.5 mL 6M NaOH (aq) and 20 mL water were added and mixture was stirred for 10 minutes. Hexanes were added, layers were separated and hexanes were washed again with brine. Organics, were concentrated to give 3.0 g light yellow liquid, a mixture of ~2:1 desired product:bis-alkylated product. MS (m/z), did not ionize. Crude product was used as-is in next reaction. 1-bromo-3-[(1 ,1-dimethylethyl)thio]benzene (3.00 g, 12.24 mmol) was dissolved in Dichloromethane (DCM) (50 mL) and cooled in an ice/water bath, MCPBA (6.86 g, 30.6 mmol) was added in portions and reaction was stirred at room temperature for 120 minutes. Reaction was diluted with satd. NaHCC^, layers were separated and organics were washed with 2M NaOH and brine. Organics were concentrated and purified by column chromatography to give the title compound as a white solid (1.90 g, 90% yield for oxidation, based on 62% purity of starting material). 1H NMR (400 MHz, CHLOROFORM-d) δ 8.05 (t, J = 1.77 Hz, 1 H), 7.82 (m, 2H), 7.46 (t, J = 7.83 Hz, 1 H), 1.38 (s, 9H); MS (m/z) 277/279.
	In 1-methyl-pyrrolidin-2-one at 80℃; for 120h;	10 Preparation 10 1 -bromo-3-[( 1 , 1 -dimethy lethyl)sulfony l]-5-methy Ibenzene 1 ,3-Dibromobenzene (1.023 mL, 8.48 mmol) was dissolved in N-Methyl-2- pyrrolidone (NMP) (20 mL) and t-butylthiol sodium salt (3.17 g, 25.4 mmol) was slowly added at room temperature. Reaction was slightly exothermic and turned medium pink/red color. Reaction was heated at 80°C for 5 days. Reaction was cooled to room temperature and 0.5 mL 6M NaOH (aq) and 20 mL water were added and mixture was stirred for 10 minutes. Hexanes were added, layers were separated and hexanes were washed again with brine. Organics were concentrated to give 3.0 g light yellow liquid, a mixture of ~2:1 desired product:bis-alkylated product. MS (m/z), did not ionize. Crude product was used as-is in next reaction. 1-bromo-3-[(1 ,1-dimethylethyl)thio]benzene (3.00 g, 12.24 mmol) was dissolved in Dichloromethane (DCM) (50 mL) and cooled in an ice/water bath, MCPBA (6.86 g, 30.6 mmol) was added in portions and reaction was stirred at room temperature for 120 minutes. Reaction was diluted with satd. NaHCC^, layers were separated and organics were washed with 2M NaOH and brine. Organics were concentrated and purified by column chromatography to give the title compound as a white solid (1.90 g, 90% yield for oxidation, based on 62% purity of starting material). 1H NMR (400 MHz, CHLOROFORM-d) δ 8.05 (t, J = 1.77 Hz, 1 H), 7.82 (m, 2H), 7.46 (t, J = 7.83 Hz, 1 H), 1.38 (s, 9H); MS (m/z) 277/279.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/120025, 2011, A1 Location in patent: Page/Page column 55-56
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2011/120026, 2011, A1 Location in patent: Page/Page column 40

51
[ 29364-29-2 ]
[ 153493-48-2 ]
[ 1355353-80-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	In tetrahydrofuran at -20 - -5℃;

Reference： [1]Location in patent: experimental part Konstantinov, Lidia S.; Popov, Vadim V.; Obruchnikova, Natalia V.; Lyssenko, Konstantin A.; Ananyev, Ivan V.; Rakitin, Oleg A. [ARKIVOC, 2011, vol. 2011, # 11, p. 69 - 81]

52
[ 31169-27-4 ]
[ 29364-29-2 ]
[ 1370008-67-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	In dimethyl sulfoxide; at 0 - 20℃; for 4h;	3-(4-tert-butylsulfanylthieno[3,2-d]pyrimidin-7-yl)cyclopent-2-en-1-oneSodium 2-methyl-2-propanethiolate (5.60 g, 50 mmol) is added to a solution of 7-bromo-4-chloro-thieno[3,2-d]pyrimidine (10.0 g, 40 mmol) in DMSO (150 mL) at 0° C.The resulting mixture is warmed up to room temperature and stirred for 4 hr, poured into ice (1500 g) and stirred until all ice melt during which a precipitate formed.The precipitate is collected by filtration, washed with water (500 mL) and dried over lyophilization to give 7-bromo-4-tert-butylsulfanyl-thieno[3,2-d]pyrimidine (10.38 g, 86percent). LCMS (m/z) M+H=303.2 and 305.1; tR=3.51 min.

Reference： [1]Patent: US2012/77814,2012,A1 .Location in patent: Page/Page column 55-56

53
[ 451-46-7 ]
[ 29364-29-2 ]
[ 13205-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-fluorobenzoic acid ethyl ester; sodium tert-butyl thiolate In N,N-dimethyl-formamide at 80℃; for 2h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide	Step 1: 4-(tert-Butylthio)benzoic acid[00411] Ethyl 4-fluorobenzoate (1.5 g, 8.9 mmol) and tert-butylsulfanylsodium(2.00 g, 17.8 mmol) were combined in N,N-dimethylformamide (10 mL). The reaction mixture was heated at 80 °C for 2 hours. A large amount of precipitate formed and an additional 15 mL of Ν,Ν-dimethylformamide was added and the reaction mixture was stirred for an additional 20 hours at 80 °C. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was discarded, and the water layer was made acidic with 4M hydrochloric acid. The water layer was extracted two times with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered, and evaporated to dryness to yield 4-(tert- butylthio)benzoic acid as a colorless oil. ESI-MS m/z calc. 210.3, found 211.1 (M+l)+.
	Stage #1: 4-fluorobenzoic acid ethyl ester; sodium tert-butyl thiolate In N,N-dimethyl-formamide at 80℃; for 22h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide	1 4-(tert-Butylsulfonyl)benzoic acid Step 1: Ethyl 4-fluorobenzoate (1.5 g, 8.9 mmol) and tert-butylsulfanylsodium (2.00 g, 17.8 mmol) were combined in DMF (10 mL). The reaction mixture was heated at 80° C. for 2 hours. A large amount of precipitate formed and an additional 15 mL of DMF was added and the reaction mixture was stirred for an additional 20 hours at 80° C. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was discarded, and the water layer was made acidic with 4M hydrochloric acid. The water layer was extracted two times with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered, and evaporated to dryness to yield 4-(tert-butylthio)benzoic acid as a colorless oil. ESI-MS m/z calc. 210.3. found 211.1 (M+1) +. Retention time: 1.74 minutes (3 min run).

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - WO2012/112743, 2012, A1 Location in patent: Page/Page column 157
[2]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US2012/196869, 2012, A1 Location in patent: Paragraph 0383; 0384; 0385

54
C₂₃H₁₈Cl₂F₃N₅O₂ [ No CAS ]
[ 29364-29-2 ]
[ 1401607-04-2 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h;	5.11 N-{2-[4-({3-Chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-2-(ethylsulfonyl)acetamide (9) General procedure: Under ice-cooling, to a solution of 6 (222 mg, 0.497 mmol) and 4-methylmorpholine (3.0 mL, 27.3 mmol) in THF (7.0 mL) was added chloroacetyl chloride (0.7 mL, 8.78 mmol), and the mixture was stirred at 0 °C for 5 h. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate (100 mL) under ice-cooling, and the mixture was extracted with AcOEt (100 mL). The extract was dried over anhydrous magnesium sulfate and concentrated in vacuo, and then the residue was dissolved in a mixed solvent of DMF (3.5 mL) and THF (6.0 mL). To the mixture was added sodium ethanethiolate (630 mg, 7.49 mmol), and the mixture was stirred at room temperature for 2 h. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate (100 mL) under ice-cooling and the mixture was extracted with AcOEt (100 mL). The extract was dried over anhydrous magnesium sulfate and concentrated in vacuo, and the residue was purified by silica gel column chromatography (AcOEt/MeOH eluent, 100:0 to 90:10) to give 9 as oil. 9 was dissolved in dichloromethane (7.0 mL), and to the solution were added m-chloroperbenzoic acid (162 mg, 0.939 mmol) at room temperature. The mixture was stirred at room temperature for 1 h. Saturated aqueous sodium thiosulfate solution (100 mL) was added to the reaction mixture under ice-cooling, and then the mixture was stirred at room temperature for 1 h. The mixture was extracted with dichloromethane (100 mL) and the extract was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was dissolved in dichloromethane (5.0 mL), and to the solution were added titanium tetraisopropoxide (0.9 mL, 3.06 mmol), MeOH (0.50 mL) and 70% aqueous tert-butyl hydroperoxide solution (10 mL, 72.2 mmol), and the mixture was stirred at room temperature for 1 h. Saturated aqueous sodium thiosulfate solution (100 mL) was added to the reaction mixture under ice-cooling, and the mixture was stirred at room temperature for 1 h. The mixture was extracted with dichloromethane (100 mL) and the extract was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography AcOEt/MeOH eluent, 100:0 to 90:10) and crystallization from diethyl etherAcOEthexane to give 167 mg (58%) of 1d as colorless crystals. The following compounds (1e, 1f) were prepared from 6 and the corresponding sodium thiolate by a method similar to that described for 1d.

Reference： [1]Kawakita, Youichi; Seto, Masaki; Banno, Hiroshi; Ohta, Yoshikazu; Tamura, Toshiya; Yusa, Tadashi; Miki, Hiroshi; Kamiguchi, Hidenori; Ikeda, Yukihiro; Tanaka, Toshimasa; Kamiyama, Keiji; Ishikawa, Tomoyasu; Miwa, Kazuhiro [Bioorganic and medicinal chemistry, 2012, vol. 20, # 20, p. 6171 - 6180,10]

55
[ 2257-69-4 ]
[ 29364-29-2 ]
[ 1409975-81-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; scandium tris(trifluoromethanesulfonate) at 160℃; for 0.5h; Microwave irradiation;	198.198A A mixture of 4-chlorophthalazin-1(2H)-one (200 mg, 1.11 mmol), sodium 2-methylpropane-2-thiolate (248 mg, 2.22 mmol), tris(trifluoromethylsulfonyloxy)scandium (54.5 mg, 0.11 mmol) and K2CO3 (308 mg, 2.22 mmol) was heated at 160° C. under microwave condition for 30 minutes. The mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered, and chromatographed (0-30% EtOAc/DCM) to give 52 mg (20%) of the title compound as a white solid: MS (DCI) 235 (M+H).

Reference： [1]Current Patent Assignee: ABBVIE INC - US2012/289500, 2012, A1 Location in patent: Page/Page column 50

56
[ 23229-26-7 ]
[ 29364-29-2 ]
[ 1428548-89-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	In acetonitrile at 100℃; for 0.5h; Inert atmosphere; Microwave irradiation;	2,5-bis(tert-Butylthio)pyrazine (8b) To a solution of 2,5-dibromopyrazine (7, 165 mg, 0.694 mmol) in acetonitrile (6 mL) was added sodium 2-methylpropane-2-thiolate (195 mg, 1.734 mmol). The mixture was stirred for 30 min at 100 °C with microwave irradiation. The reaction mixture was filtered and concentrated in vacuo. The crude product was added to a silica gel (24 g) column and was eluted with 0-50% EtOAc in hexanes to give product 8b (170 mg, 0.663 mmol, 96% yield) as a light yellow crystalline solid. 1H NMR (500 MHz, CDCl3) d: 8.42 (s, 2H), 1.50 (s, 18H); 13C NMR (125 MHz, CDCl3) d: 152.2, 146.6, 48.3, 31.0; LRMS (ESI+) calculated for C12H20N2S2, 256.1, found m/z 257.1 (M + 1).

Reference： [1]Li, Jie Jack; Meng, Wei; Wu, Shung; Wu, Yong-Jin; Guernon, Jason; Allen, Martin P.; Miller, Michael M.; Cheng, Peter T.; Chen, Bang-Chi [Tetrahedron Letters, 2013, vol. 54, # 15, p. 1938 - 1942]

57
[ 87-41-2 ]
[ 29364-29-2 ]
[ 1154908-67-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 2-benzofuran-1(3H)-one; sodium tert-butyl thiolate In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃;
72%	In N,N-dimethyl-formamide at 110℃; for 3h;

Reference： [1]Malwal, Satish R.; Gudem, Mahesh; Hazra, Anirban; Chakrapani, Harinath [Organic Letters, 2013, vol. 15, # 5, p. 1116 - 1119]
[2]Malwal, Satish R.; Chakrapani, Harinath [Organic and Biomolecular Chemistry, 2015, vol. 13, # 8, p. 2399 - 2406]

58
[ 29364-29-2 ]
[ 85027-68-5 ]
[ 74213-37-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	In tetrahydrofuran; water at 0 - 20℃; for 4h;	cis-(4R)-t-Butylthio-(3R)-phenylacetamidoazetidin-2-one (21). To a stirred solution of compound 20 (0.28 g, 1.1 mmol) in THF at 0 °C was added a solution of sodium tbutanethiolate 0.12 g, 1.1 mmol) in H2O. At the end of the addition, the ice bath was removed. After being stirred for 4 h at room temperature, the reaction mixture was diluted with EtOAc (15 mL) and washed three times with brine. The organic layer was dried over MgSO4 and evaporated to dryness. Column chromatography of the residue on a silica gel column with EtOAc-hexanes (2:1) as an eluent gave the title compound (0.16 g, 51%).

Reference： [1]Lee, Sang Hyup [Bulletin of the Korean Chemical Society, 2013, vol. 34, # 1, p. 121 - 127]

59
N-(1,3-benzothiazol-5-yl)-6-iodo-7-(methyloxy)-4-quinazolinamine [ No CAS ]
[ 29364-29-2 ]
4-(benzo[d]thiazol-5-ylamino)-6-(tert-butylthio)quinazolin-7-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	In N,N-dimethyl-formamide at 150℃;	33 Example 33. 4-(benzo[d]thiazol-5-ylamino )-6-(tert-butylthio )quinazolin-7-ol To a solution of N-1,3-benzothiazol-5-yl-6-iodo-7-(methyloxy)-4-quinazolinamine(100 mg, 0.23 mmol) in DMF (2 mL) was added sodium 2-methyl-2-propanethiolate (258mg, 2.30 mmol). The reaction mixture was stirred at 150 oc for 3 days. The solvent wasevaporated under vacuum and crude material was purified by column chromatography to5 provide 45 mg of the title compound (49%). MS: m/z: 383 [M+H+]
49%	In N,N-dimethyl-d<SUB>6</SUB>-formamide at 150℃; for 72h;	33 4-(benzo[d]thiazol-5-ylamino)-6-(tert-butylthio)quinazolin-7-ol Example 33 4-(benzo[d]thiazol-5-ylamino)-6-(tert-butylthio)quinazolin-7-ol To a solution of N-1,3-benzothiazol-5-yl-6-iodo-7-(methyloxy)-4-quinazolinamine (100 mg, 0.23 mmol) in DMF (2 mL) was added sodium 2-methyl-2-propanethiolate (258 mg, 2.30 mmol). The reaction mixture was stirred at 150 °C for 3 days. The solvent was evaporated under vacuum and crude material was purified by column chromatography to provide 45 mg of the title compound (49%). MS: m/z: 383 [M+H]+.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2013/25958, 2013, A1 Location in patent: Page/Page column 77; 78
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - EP2744501, 2016, B1 Location in patent: Paragraph 0222; 0223

60
[ 16567-18-3 ]
[ 29364-29-2 ]
[ 653570-21-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium hydroxide In dimethyl sulfoxide at 20 - 80℃; Inert atmosphere;	4.2. 2-Methyl-8-thioterbutylquinoline (TTbQ-Me) To a solution of KOH (8 g; 142.6 mmol) in DMSO (20 ml), sodium terbutylate (3.20 g; 26.4 mmol) and 8-bromoquinoline (2 g;9.0 mmol) were added under inert atmosphere (Ar) and the mixture was stirred at R.T. for 5 h and overnight at 80 oC. 50 ml of H2O and 50 ml of diethyl ether were added to the resulting solution and the organic phase was separated and dried on Na2SO4. The suspension was filtered off (G3) and the resulting clear solution was dried under vacuum. The crude product was purified by flash chromatography on silica column with a mixture of CH2Cl2/Et2O(70/30 v/v). 0.95 g (46% yield) of the title product was obtained upon evaporation of the solvent. 1H NMR (CDCl3, T 298 K, ppm) d: 1.40 (s, 9H, tBu), 2.81 (s, 3H,CH3 quinoline), 7.31 (d, 1H, J 8.4 Hz, H3), 7.44 (dd, 1H, J 8.1, 7.2 Hz,H6), 7.77 (dd, 1H, J 8.1, 1.4 Hz, H5), 8.00 (dd, 1H, J 7.2, 1.4 Hz, H7),8.04 (d, 1H, J 8.40 Hz, H4).13C{1H} NMR (CDCl3, T 298 K, ppm) d: 25.6 (CH3, CH3 quinoline),31.3 (CH3, CMe3), 46.9 (C, CMe3), 122.0 (CH, C3), 125.0 (CH, C6),127.0 (C, C10), 128.4 (CH, C5), 133.2 (C, C8), 136.4 (CH, C4), 137.9 (CH,C7), 148.8 (C, C9), 159.2 (C, C2). Anal calc. for C14H17NS: C, 72.68; H,7.41; N, 6.05. Found C, 72.71; H, 7.29; N, 5.93%.

Reference： [1]Canovese, Luciano; Visentin, Fabiano; Santo, Claudio; Bertolasi, Valerio [Journal of Organometallic Chemistry, 2014, vol. 749, p. 379 - 386]

61
Mo(NtBu)2Cl(dmampS) [ No CAS ]
[ 29364-29-2 ]
Mo(NtBu)2(dmampS)(StBu) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 20℃; Inert atmosphere;	2.4 Synthesis of Mo(N^tBu)₂(dmampS)(S^tBu) (3) Mo(NtBu)2Cl(dmampS) (0.5g, 1.2mmol) and Na(StBu) (0.14g, 1.2mmol) were suspended in THF (100mL). After stirring the mixture at room temperature overnight, the reaction mixture was filtered and then solvent was removed in vacuo at 25°C. The crude product (0.4g, 70%) was purified by sublimation at 65°C under a reduced pressure of 10-1Torr. 1H NMR (C6D6, 300MHz): δ 1.40 (s, 6H, (CH3)2NCH2C(CH3)2S-), 1.46 (s, 18H, =NC(CH3)3), 1.73 (s, 9H, (CH3)3CS-), 2.51 (s, 2H, (CH3)2NCH2C(CH3)2S-), 2.62 (s, 6H, (CH3)2NCH2C(CH3)2S-). 13C NMR (C6D6, 300MHz): δ 31.5, 34.6, 36.4, 43.8, 44.0, 50.4, 69.7, 78.2. FT-IR (KBr, cm-1): 2970 (s), 2920 (s), 1452 (m), 1473 (s), 1400 (s), 1 (s), 1243 (w), 1207 (s), 1150 (w), 1127 (m), 1024 (w), 1005 (w), 963 (w), 917 (br), 866 (w), 837 (m), 801 (w), 746 (w), 606 (m), 562 (w), 476 (m), 460 (m). EI-MS: 461 [M+H]+. MoN3C18S2H41 (459.63): Calcd. C, 47.04; H, 8.99; N, 9.14; S, 13.95. Found: C, 46.31; H, 9.13; N, 8.87; S, 12.34%.

Reference： [1]Yeo, So Jeong; Oh, Hyunji; You, Tae-Soo; Jeon, Dong Ju; Chung, Taek-Mo; Park, Bo Keun; Kim, Chang Gyoun [Polyhedron, 2015, vol. 100, p. 199 - 205]

62
W(NtBu)2Cl(dmampS) [ No CAS ]
[ 29364-29-2 ]
W(NtBu)2(dmampS)(StBu) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In tetrahydrofuran for 24h; Inert atmosphere; Reflux;	2.7 Synthesis of W(N^tBu)₂(dmampS)(S^tBu) (6) W(NtBu)2Cl(dmampS) (1.0g, 2.0mmol) and Na(StBu) (0.2g, 2.0mmol) were suspended in THF (100mL) and the mixture was refluxed for 24h. After cooling, solvent was removed in vacuo to obtain 6 as yellow powder. The crude product was sublimed at 110°C under a reduced pressure of 10-1Torr to give yellow microcrystalline material. (0.9g, 78%). 1H NMR (C6D6, 300MHz): δ 1.38 (s, 6H, (CH3)2NCH2C(CH3)2S-), 1.49 (s, 18H, =NC(CH3)3), 1.74 (s, 9H, (CH3)3CS-), 2.60 (s, 2H, (CH3)2NCH2C(CH3)2S-), 2.65 (s, 6H, (CH3)2NCH2C(CH3)2S-). 13C NMR (C6D6, 300MHz): δ 31.9, 33.1, 34.0, 44.4, 48.4, 50.2, 67.2, 78.2. FT-IR (KBr, cm-1): 2970 (s), 2893 (s), 2703 (w), 2597 (w), 1513 (w), 1453 (m), 1402 (w), 1375 (m), 1356 (m), 1280 (m), 1233 (s), 1215 (s), 1130 (m), 1098 (w), 1062 (w), 1026 (w), 1008 (w), 970 (w), 911 (br), 838 (s), 777 (br), 608 (w), 585 (w), 561 (w), 481 (w), 465 (w). EI-MS: 547 [M]+. WN3C18S2H41 (547.51): Calcd. C, 39.49; H, 7.55; N, 7.67; S, 11.71. Found: C, 39.10; H, 7.86; N, 7.07; S, 12.43%.

Reference： [1]Yeo, So Jeong; Oh, Hyunji; You, Tae-Soo; Jeon, Dong Ju; Chung, Taek-Mo; Park, Bo Keun; Kim, Chang Gyoun [Polyhedron, 2015, vol. 100, p. 199 - 205]

63
[ 29364-29-2 ]
[ 942-91-6 ]
[ 5925-55-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide; In diethyl ether; water; at 20℃; for 5h;	In a 500 mL roundbottomed flask equipped with a magnetic stirrer, 150 mL of a diethyl ether solution of s-(thiobenzoyl)thioglycolic acid (0.27 g, 2.4 mmol) was added to 100 mL of an aqueous basic solution (NaOH, 1 mol L-1) of sodium 2-methyl-2-propanethiolate (0.510g, 2.9 mmol). This biphasic mixture was vigorously stirred at room temperature for 5 hours. Then, the purple ether phase was removed and washed twice with 500 mL of an aqueous basic solution (NaOH 1 mol L-1) and twice with 500 mL of a 10% NaCl aqueous solution and dried over anhydrous magnesium sulfate. Purification by silica gel chromatography (Kiesegel-60) with petroleum ether/ethyl acetate (99/1 :v/v) as eluent gave tert-butyl dithiobenzoate (t-BDB) as a dark purple oil (90% yield). 1 H NMR (CDCL3) d (ppm): 1.69 (S, 9H, 3*CH3), 7.36 (m, 2H, meta-ArH), 7.50 (m, 1H, para-ArH) and 7.88 (m, 2H, ortho-ArH).

Reference： [1]Patent: EP2960263,2015,A1 .Location in patent: Paragraph 0097

64
Mo(NtBu)2Cl2(dimethoxyethane) [ No CAS ]
[ 29364-29-2 ]
2C₄H₉N^(2-)*Mo⁽⁶⁺⁾*2C₄H₉S^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: Mo(N<SUP>t</SUP>Bu)<SUB>2</SUB>Cl<SUB>2</SUB>(dimethoxyethane); sodium tert-butyl thiolate In tetrahydrofuran at 20℃; for 24h; Stage #2: at 65℃;	Mo(NtBu)2Cl2(DME) (DME=dimethoxyethane) (1.00g, 2.50mmol) and Na(StBu) (0.60g, 5.00mmol) were suspended in THF (tetrahydrofuran, 30mL). After stirring the mixture at room temperature for 24h, the reaction mixture was evaporated in vacuo to obtain yellow powder. The crude product was sublimed at 65°C under a reduced pressure of 10-1Torr to give yellow microcrystalline material(0.77g, 74%). 1H NMR (C6D6, 300MHz): δ 1.36 (s, 18H,=NC(CH3)3), 1.69 (s, 18H, -SC(CH3)3). 13C NMR (C6D6, 300MHz): δ 32.0 (=NC(CH3)3), 35.9 (-SC(CH3)3), 45.6 (-SC(CH3)3), 70.7 (=NC(CH3)3). FT-IR (KBr, cm-1): 2973 (vs), 2922 (vs), 2889 (vs), 2856 (vs), 2707 (w), 2570 (w), 2379 (w), 2289 (w), 2161(w), 1721 (w), 1667 (w), 1575 (w), 1470 (s), 1452 (vs), 1390 (m), 1357 (vs), 1242 (vs), 1205 (vs), 1161 (vs), 1117 (s), 1026 (m), 898 (m, br), 840 (m), 804 (m), 837 (s), 804 (w), 748 (w), 574 (w), 546 (m), 470 (w), 438 (m). EI-MS: 418 [M]+. Anal. Calcd for C16H36MoN2S2: calcd. C 46.13, H 8.71, N 6.73, S 15.39; found: C 45.42, H 8.72, N 6.57, S 14.39.

Reference： [1]Jang, Yujin; Kim, Jun Beom; Hong, Tae Eun; Yeo, So Jeong; Lee, Sunju; Jung, Eun Ae; Park, Bo Keun; Chung, Taek-Mo; Kim, Chang Gyoun; Lee, Do-Joong; Lee, Han-Bo-Ram; Kim, Soo-Hyun [Journal of Alloys and Compounds, 2016, vol. 663, p. 651 - 658]

65
4,4-dichloro-1,1-bis(4-chlorophenyl)-2-azabuta-1,3-diene [ No CAS ]
[ 29364-29-2 ]
1,1-bis(4-chlorophenyl)-3,4-bis(tertbutylthio)-2-azabuta-1,3-diene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	In N,N-dimethyl-formamide at 20℃; for 8h;	11 General procedure for the synthesis of 2-azabuta-1,3-dienes 5, 6, and 7. General procedure: 1,1-Diaryl-4,4-dichloro-2-azabuta-1,3-diene (1.1 mmol)was stirred with an excess of thiolate (10 mmol) in dry DMF(10 mL). The reaction mixture was stored at room temperaturefor 8 h, then poured into water (100 mL) and extracted with diethyl ether (150 mL). The organic solutionwas washed three times with water, dried over anhydroussodium sulfate and evaporated. The crude residue wasrecrystallized from ethanol or hexane.

Reference： [1]Kinghat, Rodolphe; Schmitt, Gérard; Ciamala, Kabula; Khatyr, Abderrahim; Knorr, Michael; Jacquot-Rousseau, Sandrine; Rousselin, Yoann; Kubicki, Marek M. [Comptes Rendus Chimie, 2016, vol. 19, # 3, p. 319 - 331]

66
[ 29364-29-2 ]
[ 239806-18-9 ]
1,1-diphenyl-3,4-bis(tertbutylthio)-2-azabuta-1,3-diene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In N,N-dimethyl-formamide at 20℃; for 8h;	10 General procedure for the synthesis of 2-azabuta-1,3-dienes 5, 6, and 7. General procedure: 1,1-Diaryl-4,4-dichloro-2-azabuta-1,3-diene (1.1 mmol)was stirred with an excess of thiolate (10 mmol) in dry DMF(10 mL). The reaction mixture was stored at room temperaturefor 8 h, then poured into water (100 mL) and extracted with diethyl ether (150 mL). The organic solutionwas washed three times with water, dried over anhydroussodium sulfate and evaporated. The crude residue wasrecrystallized from ethanol or hexane.

Reference： [1]Kinghat, Rodolphe; Schmitt, Gérard; Ciamala, Kabula; Khatyr, Abderrahim; Knorr, Michael; Jacquot-Rousseau, Sandrine; Rousselin, Yoann; Kubicki, Marek M. [Comptes Rendus Chimie, 2016, vol. 19, # 3, p. 319 - 331]

67
(2S,4S)-1-((R)-2-(2-naphthamido)-3-cyclohexylpropanoyl)-4-hydroxy-N-((R)-2-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)propyl)pyrrolidine-2-carboxamide [ No CAS ]
[ 29364-29-2 ]
(2S,4R)-1-((R)-2-(2-naphthamido)-3-cyclohexylpropanoyl)-4-(tert-butylthio)-N-((R)-2-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)propyl)pyrrolidine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	Stage #1: (2S,4S)-1-((R)-2-(2-naphthamido)-3-cyclohexylpropanoyl)-4-hydroxy-N-((R)-2-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)propyl)pyrrolidine-2-carboxamide With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 23℃; for 1.33333h; Stage #2: sodium tert-butyl thiolate In ethanol at 23℃;	9.1 Step 1: Preparation of (2S,4R)- 1 -((R)-2-(2-naphthamido)-3 -cyclohexylpropanoyl)-4- (tert-butylthio)-N-((R)-2-methyl- 1 -((3 aS,4S,6S, 7aR)-3 a, 5,5 -trimethylhexahydro-4, 6- methanobenzo[d] [1,3 ,2]dioxaborol-2-yl)propyl)pyrrolidine-2-carboxamide Into a 25 mL round-bottom flask, equipped with a magnetic stir bar and under nitrogen was added (2S,45)- 1 -((R)-2-(2-naphthamido)-3 -cyclohexylpropanoyl)-4- hydroxy-N-((R)-2-methyl- 1 -((3 aS,4S, 6S,7aR)-3 a, 5,5 -trimethylhexahydro-4,6- methanobenzo[d] [1,3,2] dioxaborol-2-yl)propyl)pyrrolidine-2-carb oxamide (336 mg, 0.5 mmol, 1.0 equiv), EtN(iPr)2 (130 1iL, 0.75 mmol, 1.5 equiv) and CH2C12 (5 mL). The solution was cooled to 0 °C in an ice bath and treated with drop wise addition of triflic anhydride (109 1iL, 0.65 mmol, 1.3 equiv). The solution was stirred at 0 °C for 20 minutes and then allowed to warm to room temperature over 1 h. The reaction mixture was quenched with water (20 mL) and extracted with CH2C12 (3 x 10 mL) using a 75 mL separatory funnel. The combined organic layers were washed with brine (10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The crude reaction mixture as taken up in ethanol (10 mL) and split into two portions. One portion (5 mL, approx 0.25 mmol) was treated with sodium thio tert-butoxide (56 mg, 0.5 mmol, 2.0 equiv) and stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and purified by reverse-phase column chromatography through a Cl 8 column, eluting with 90:10 to 0:100 H20:MeCN + 0.1% formic acid as a gradient. Fractions containing the desired product were concentrated under reduced pressure to afford the title compound (27 mg, 14%). H20:MeCN + 0.1% formic acid as a gradient. Fractions containing the desired product were concentrated under reduced pressure to afford the title compound (27 mg, 14%).

Reference： [1]Current Patent Assignee: OPHTHOTECH CORPORATION - WO2016/100555, 2016, A1 Location in patent: Paragraph 0154

68
[ 10381-82-5 ]
[ 29364-29-2 ]
8-(tertbutylthio)caffeine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In ethanol for 14h; Reflux;	Synthesis of C8-subsitutedthiocaffeine analogues (4-10) General procedure: A mixture of 8-bromocaffeine (1 mmol) and the appropriate sodium thiolate(4 mmol) in ethanol was heated under reflux for 2-48 h and when cooled to roomtemperature. The solution was evaporated until the product started toprecipitate. The resulting precipitate was filtered off and recrystallizatedfrom ethanol (compounds 4-7), petroleum ether (compounds 8 and 9) and ethanol : chloroform; 2 : 1 (compound 10).

Reference： [1]Jasiewicz, Beata; Sierakowska, Arleta; Wandyszewska, Natalia; Warżajtis, Beata; Rychlewska, Urszula; Wawrzyniak, Rafał; Mrówczyńska, Lucyna [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 3994 - 3998]

69
Cl₄NRu [ No CAS ]
[ 29364-29-2 ]
Na(H₂O)₂[Ru(NO)(SBu^t)(μ-SBu^t)]₃(μ₃-S)(μ₃-O) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Schlenk technique;	5 2.5 Preparation of Na(H₂O)₂[Ru(NO)(SBu^t)(μ-SBu^t)]₃(μ₃-S)(μ₃-O) (Na(H₂O)₂2) To a solution of Ru(NO)Cl3 (24 mg, 0.10 mmol) in thf (10 mL) was added 3 equivalents of NaSBut (34 mg, 0.3 mmol). The reaction mixture was stirred at room temperature for 12 h. The volatiles were removed in vacuo, and the residue was extracted with hexanes. Recrystallization from hexanes at room temperature afforded red crystals which were suitable for X-ray analysis. Yield: 36 mg (76%). 1H NMR (400 MHz, acetone-d6): δ = 1.80 (s, 27H, But), 1.91 (s, 27H, But), 3.02 (br. s, 4H, H2O) ppm. IR (KBr, cm-1): 1786 [ν(N-O)], 1792 [ν(N-O)], 1801 [ν(N-O)]. MS (FAB): m/z 967 (M+ - 2H2O - S). Anal. Calcd for C24H58N3NaO6Ru3S7·H2O: C, 27.36; H, 5.74; N, 3.99; S, 21.29. Found: C, 27.16; H, 5.44; N, 3.55; S, 21.12.

Reference： [1]Chan, Ka-Wang; Ng, Wai-Ming; Cheung, Wai-Man; Lai, Chun-Sing; Sung, Herman H.Y.; Williams, Ian D.; Leung, Wa-Hung [Journal of Organometallic Chemistry, 2016, vol. 812, p. 151 - 157]

70
W(NtBu)2Cl(dmampS) [ No CAS ]
[ 29364-29-2 ]
C₁₇H₄₁N₃S₂W [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In tetrahydrofuran for 24h;	preparation of W(N^tBu)2(S^tBu)(dmampS) 100 mL Herr Lenk flask in Example 1 from the obtained W(NtBu)2Cl(dmampS) (1.0 g, 2.0 mmol, 1 eq) and sodium 2-methylpropane-2-thiolate (0.2 g, 2.0 mmol, 1 eq ) after the insert after the addition of tetrahydrofuran (50 mL) was stirred for 24 hours. After filtering the solution obtained by removing the solvent under reduced pressure to sublimation at 110 °C under reduced pressure to remove the impurities to get a yellow solid compound. And the obtained compound is 0.9 g, the yield was 78%

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - KR101485520, 2015, B1 Location in patent: Paragraph 0080; 0081

71
[ 886762-64-7 ]
[ 29364-29-2 ]
2-(tert-butylthio)-3-methylbenzaldehyde [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5676 - 5679

72
[ 29364-29-2 ]
[ 89763-93-9 ]
[ 1383611-96-8 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5676 - 5679

73
[ 437-81-0 ]
[ 29364-29-2 ]
2-(tert-butylthio)-6-fluorobenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In N,N-dimethyl-formamide at 0 - 20℃; for 14h;

Reference： [1]Bouisseau, Anaïs; Glancy, John; Willis, Michael C. [Organic Letters, 2016, vol. 18, # 21, p. 5676 - 5679]

74
Mo(NtBu)2Cl(dmampS) [ No CAS ]
[ 29364-29-2 ]
C₁₈H₄₁MoN₃S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In tetrahydrofuran for 24h; Schlenk technique;	2 (0.5 g, 1.2 mmol, 1 eq) Mo(NtBu)2Cl(dmampS) and sodium 2-methylpropane-2-thiolate (0.14 g, 1.2 mmol, 1 eq) obtained in Example 3 were added to a 50 mL Schlenk flask, , Tetrahydrofuran (30 mL) was added, and the mixture was stirred for 24 hours. The resulting solution was filtered, and the solvent was removed under reduced pressure to obtain a yellow solid compound. Subsequently, the solution was sublimed at 60 ° C under reduced pressure to remove impurities. The obtained compound was 0.4 g, and the yield was 76%.

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - KR101485522, 2015, B1 Location in patent: Paragraph 0077-0084

75
C₂₀H₃₀Cl₂N₄W [ No CAS ]
[ 29364-29-2 ]
C₁₆H₃₆N₂S₂W [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In tetrahydrofuran for 24h;	1 Preparation of W(NtBu)2(StBu)2 In a 50 mL Schlenk flaskW (NtBu) 2Cl2 (py) (py = pyridine) (0.1 g, 0.2 mmol, 1 eq) andSodium 2-methylpropane-2-thiolate (0.04 g, 0.4 mmol, 2 eq)After addition of tetrahydrofuran (50 mL)And the mixture was stirred for 24 hours.The reaction solution was filtered, and the solvent was removed under reduced pressure to obtain a green solid compound. The obtained compound was 0.08 g,The yield was 89%.

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - KR101505126, 2015, B1 Location in patent: Paragraph 0060-0061

76
[(6RS)-2-(2-acetamidopyridin-4-yl)-3-anilino-4-oxo-4,5,6,7-tetrahydro-1H-indol-6-yl]methyl methanesulfonate [ No CAS ]
[ 29364-29-2 ]
N-4-[(6RS)-6-[(tert-butylsulfanyl)methyl]-4-oxo-3-(phenylamino)-4,5,6,7-tetrahydro-1H-indol-2-yl]pyridin-2-ylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	In N,N-dimethyl acetamide at 100℃; for 5h;	191 Exampe 191 N-4-[(6RS)-6-[(tert-butylsulfanyl)methyl]-4-oxo-3-(phenylamino)-4,5,6,7-tetrahydro-1H-indol-2-yl]pyridin-2-ylacetamide A mixture of [(6RS)-2-(2-acetamidopyridin-4-yl)-3-anilino-4-oxo-4,5,6,7-tetrahydro-1 H-indol-6- yl]methyl methanesulfonate (151-1; 75mg, 160 pmol) and sodium 2-methylpropane-2-thiolate (108 mg, 960 pmol) in DMA (3 mL)was stirred at 100C for S h. Water was added, the mixture concentrated and pudfied by preparalive HPLC (basic method) to gve the hUe compound (45 mg,58%).1H NMR (400 MHz, DMSO-d6) ö ppm 1.29 (9H), 2.07 (3H), 2.25-2.36 (2H), 2.40-2.48 (1H), 2.61-2.71 (3H), 3.11 (1H), 6.55 (2H), 6.60 (1H), 7.01 (2H), 7.15 (1H), 7.35 (1H), 8.07 (1H), 8.23 (1H),10.33 (1H), 11.94 (1H)

Reference： [1]Current Patent Assignee: BAYER AG - WO2016/202755, 2016, A1 Location in patent: Page/Page column 221; 222

77
[ 29364-29-2 ]
rac-(E)-1,3-bis(4-chlorophenyl)-2-propen-1-yl acetate [ No CAS ]
C₁₉H₂₀Cl₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With bis(η3-allyl-μ-chloropalladium(II)); trimethylsilyl (E)-N-(trimethylsilyl)formimidate; potassium acetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In dichloromethane at -15℃; for 18h; Inert atmosphere; enantioselective reaction;

Reference： [1]Cai, Junmei; Cai, Juewang; Zheng, Purui; Wang, Xiaorong; Zhao, Xiaoming [RSC Advances, 2017, vol. 7, # 1, p. 256 - 259]

78
[ 2508-01-2 ]
[ 29364-29-2 ]
3-[2-(tert-butylthio)ethyl]-2-oxazolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.6%	With air for 3h; Reflux;	6.1 Step 1: Synthesis of 3-[2-(tert-Butylthio)ethyl]-2-oxazolidinone (Structural Formula (2^C-3)) This reaction was carried out in air. To a 200 mL four-necked round-bottom flask, a magnetic stirrer bar, a condenser, and a thermometer were attached. Then, 3-(2-chloroethyl)-2-oxazolidinone (6-1) (12.5 g, 83.8 mmol, 1.0 equivalents) obtained in Step 1 of Example 1, MeOH (80 mL), and sodium salt of 2-methyl-2-propanethiol (5-8) (NaStBu) (purity: 98.7%, 10.0 g, 88.0 mmol, 1.05 equivalents) were introduced sequentially, and the obtained suspension was stirred under reflux for 3 hours. The reaction liquid was concentrated under reduced pressure, and the obtained residue was directly filtered and purified by silica gel column chromatography (eluent: toluene/ethyl acetate=2/1 to 1/2) to obtain 15.6 g of title compound (2C-3) as a colorless liquid. Isolated yield: 91.6%. 1H NMR (400 MHz, CDCl3): δ=4.36-4.28 (m, 2H), 3.68-3.62 (m, 2H), 3.44 (t, J=6.8 Hz, 2H), 2.72 (t, J=6.8 Hz, 2H), 1.31 (s, 9H). 13C NMR (100 MHz, CDCl3): δ=158.26, 61.76, 45.31, 44.58, 42.50, 30.91, 26.58.

Reference： [1]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - US2017/233418, 2017, A1 Location in patent: Paragraph 0233; 0234; 0235; 0236; 0237; 0238

79
(NEt₄)[Ni(2-(N-(dimethylaminoethyl)aminocarbonyl)benzenethiolate)Cl] [ No CAS ]
[ 29364-29-2 ]
[Ni₃(2-(N-(dimethylaminoethyl)aminocarbonyl)benzenethiolate)2(tert-butylthiolate)2] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In methanol for 24h; Inert atmosphere;	3 [Ni3(NNAmS)2(StBu)2], 7f Under nitrogen, a solution of sodium 2-methyl-2-propanethiolate(0.13 g, 1.15 mmol) in 10 mL of methanol was added dropwiseto a solution of (NEt4)[Ni(NNAmS)Cl] (0.365 g, 1.15 mmol) in 20 mLof methanol. The solution turned dark red. While stirring for 24 h ablack precipitate deposited which was isolated by filtration,washed with diethyl ether and dried, resulting in 7f as a blackpowder (0.12 g, 0.33 mmol, 86%). Vapor diffusion of hexanes intoa CH2Cl2 solution under nitrogen yielded dark red crystals whichwere suitable for X-ray diffraction. Elemental Anal.: Calc. forC30H46N4O2S4Ni3: C, 45.10; H, 5.76; N, 7.01. Found: C, 44.63; H,5.90; N, 6.87. IR (cm1): 3059, 2970, 2886, 1650, 1572, 1527,1455, 1147, 1004, 749. ESI-MS (negative mode, methanol, m/z):369 [Ni(NNAmS)(StBu)], (positive mode) 799 [{Ni3(NNAmS)2(StBu)2}+H]+, 821 [{Ni3(NNAmS)2(StBu)2}+Na]+. UV-Vis (methanol);kmax (nm): 269, 318, 405. 1H NMR (CD3OD, d, integration notpossible due to minimal solubility): 1.36 (s, S(C(CH3)3), 1.68 (s, N(CH3)2), 3.31 (m, NCH2), 3.48 (m, NCH2), 7.10-7.45 (m, Ar-H).

Reference： [1]Senaratne, Nilmini K.; Mwania, Tom M.; Moore, Curtis E.; Eichhorn, David M. [Inorganica Chimica Acta, 2018, vol. 476, p. 27 - 37]

80
[Ni(2-(N-(dimethylaminoethyl)iminomethyl)benzenethiolate)Cl] [ No CAS ]
[ 29364-29-2 ]
[Ni(2-(N-(dimethylaminoethyl)iminomethyl)benzenethiolate)(tert-butylthiolate)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	In methanol for 24h; Inert atmosphere;	3 [Ni(NNImS)(StBu)], 3f Under nitrogen, a solution of sodium 2-methyl-2-propanethiolate(0.018 g, 0.16 mmol) in 10 mL methanol was added dropwiseto a solution of [Ni(NNImS)Cl] (0.045 g, 0.15 mmol) in 10 mL ofmethanol. After stirring for 24 h, the resulting black solution wasfiltered and the solvent removed under reduced pressure to givea black solid. Extraction with CH2Cl2, filtration and removal ofthe solvent under reduced pressure gave 3f as a black powder(0.02 g, 0.06 mmol, 38%). X-ray quality crystals were formed byvapor diffusion of diethyl ether into a CH2Cl2 solution under anitrogen environment. Elemental Anal. Calc. for C15H24N2S2Ni: C,50.72; H, 6.81; N, 7.89. Found: C, 49.40; H, 6.70; N, 7.46. IR (KBrpellet, cm1): 2960, 2922, 1602, 1588, 1530, 1512, 1456, 1362,1218, 1158, 1069, 1007, 869, 784, 749, 720, 702. ESI-MS (positivemode, methanol, m/z): 355 [Ni(NNImS)StBu+H]+, 265 [Ni(NNImS)]+,619 [{Ni(NNImS)}2StBu]+. UV-Vis (acetonitrile); kmax (nm): 253,456. 1H NMR (CD3CN, d): 8.23 (s, 1H, NH), 7.94-6.94 (m, 4H,Ar-H), 3.70 (t, 2H, NCH2), 2.63 (s, 6H, N(CH3)2), 2.40 (t, 2H,N(CH3)2CH2), 1.53 (s, 9H, S(CH3)3).

Reference： [1]Senaratne, Nilmini K.; Mwania, Tom M.; Moore, Curtis E.; Eichhorn, David M. [Inorganica Chimica Acta, 2018, vol. 476, p. 27 - 37]

81
[ 1072-97-5 ]
[ 29364-29-2 ]
[ 71167-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; <i>L</i>-proline; sodium hydroxide In dimethyl sulfoxide at 120℃; for 12h; Inert atmosphere; Sealed tube;	Synthesis of 5-tert-butylsulfanyl-pyridin-2-ylamine (I-1) To a mixture of 5-bromo-pyridin-2-ylamine (300 mg, 1.73 mmol) in DMSO (3 mL) are added sodium 2-methyl-2-propanethiolate (388 mg, 3.47 mmol) and NaOH (35 mg, 0.87 mmol). The mixture is degassed with Ar for 20 min. To the reaction mixture are added L-proline (100 mg, 0.870 mmol) and CuI (330 mg, 1.73 mmol) and the reaction is heated to 120° C. for 12 h in a sealed tube. The reaction is then cooled to room temperature, poured into ice water, and extracted with EtOAc (2×). The solvent is removed under reduced pressure to provide 200 mg of crude 5-tert-butylsulfanyl-pyridin-2-ylamine (I-1) that was used without further purification.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US2018/72717, 2018, A1 Location in patent: Paragraph 0235

82
3,3'-bis(chloromethyl)-9,9'-dimethyl-9H,9'H-1,1'-bipyrido[3,4-b]indole [ No CAS ]
[ 29364-29-2 ]
3,3'-bis((tert-butylthio)methyl)-9,9'-dimethyl-9H,9'H-1,1'-bipyrido[3,4-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: sodium tert-butyl thiolate With sodium hydride In N,N-dimethyl-formamide Cooling with ice; Inert atmosphere; Stage #2: 3,3'-bis(chloromethyl)-9,9'-dimethyl-9H,9'H-1,1'-bipyrido[3,4-b]indole In N,N-dimethyl-formamide for 2h; Inert atmosphere;	3.2 Synthesis of compound 3 General procedure: The corresponding thiol (200mg) dissolved in anhydrous DMF, the NaH (1.2 equiv.) was added into the thiol solution under ice-bath. After compound 2 (1.0 equiv.) was added into the solution, it was stirred for 2h. After reaction finished examined by TLC, the reaction was quenched by ice-water. Ethyl acetate (15×3mL) was used to extract the reactants. The combined organic layers were dried over Na2SO4. The organic solvents was removed under the reduced pressure to afford the residue which was isolated and purified by column chromatography using the mixture of ethyl acetate/petroleum (8/1, v/v) to give compound 3.

Reference： [1]Xing, Yongfei; Wu, Shijie; Dong, Mengxian; Wang, Jie; Liu, Li; Zhu, Huajie [Tetrahedron, 2019, vol. 75, # 36]

83
[ 110-06-5 ]
[ 29364-29-2 ]

Yield	Reaction Conditions	Operation in experiment
	With diethylene glycol dimethyl ether; sodium In tetrahydrofuran for 24h; Inert atmosphere;	Di-tertbutyldisulfide (1.1 mL, 5.7 mmol) and diglyme(0.5 mL) were added to a suspension of sodium (0.23 g, 10 mmol) in THF (20 mL). The reaction mixture was stirred for 24 h

Reference： [1]Skabitskii; Sakharov; Pasynskii; Eshmakov [Russian Journal of Coordination Chemistry, 2019, vol. 45, # 8, p. 539 - 547][Koord. Khim., 2019, vol. 45, # 8, p. 451 - 460,10]

84
[ 32995-11-2 ]
[ 29364-29-2 ]
trans-RuH(StBu)(1,2-bis(diethylphosphino)ethane)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In acetone Inert atmosphere;	trans-FeH(X)(depe)2, 1a, 1b, 1d, 1e General procedure: The complex FeHCl(depe)2 (0.2g, 0.4 mmol) and a slight excess of NaX (X = N3 , NCO , NCS , Br ) were stirred overnight in acetone (20 mL). The fine sodium salts that formed were filtered off through Celite and the filtrate taken to dryness. The solid was dissolved in benzene (5 mL) and hexanes (5 mL) added. The volume of this solution was reduced under vacuum and placed in the refrigerator. The solid that formed was filtered off and the filtrate was slowly taken to dryness to leave the product as needles.

Reference： [1]Cappellani, E. Paul; Drouin, Samantha D.; Golombek, Adina; Maltby, Patricia A.; Morris, Robert H.; Rennie, Benjamin E.; Schweitzer, Caroline T. [Inorganica Chimica Acta, 2021, vol. 516]

85
[ 155477-65-9 ]
[ 29364-29-2 ]
C₆₄H₅₀F₂₄P₄RuS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 20℃; for 0.0833333h; Inert atmosphere;	trans-RuH(X)(dtfpe)2, 2m, 2o General procedure: A mixture of [RuH(dtfpe)2]BF4 (0.2 g)and an excess amount of MX (KNCS for 2o, NaStBu for 2 m) in MeOH (10 mL) was stirred at room temperature for 5 min to give a colorless solution. The MeOH was removed completely under vacuum. The residue was extracted with CH2Cl2 (10 mL). Addition of hexane (20 mL) produced a white solid.

Reference： [1]Cappellani, E. Paul; Drouin, Samantha D.; Golombek, Adina; Maltby, Patricia A.; Morris, Robert H.; Rennie, Benjamin E.; Schweitzer, Caroline T. [Inorganica Chimica Acta, 2021, vol. 516]

86
[ 75-15-0 ]
[ 29364-29-2 ]
[ 71127-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 0 - 20℃; for 3h;	3.2. Preparation of sodium t-butyltrithiocarbonate Sodium t-butyl thiolate (5.60 g, 50 mmol) was dissolved in 100 mL of THF and cooled to 0 °C. To this solution carbon disulfide (3.02 mL, 50 mmol) was added dropwise. The cooling bath was removed and the mixture was warmed to room temperature for 3 hrs. The resulting yellow solution was used for farther reactions.

Reference： [1]El-khateeb, Mohammad; Moriyama, Hayato; Yoshida, Yukihiro; Kitagawa, Hiroshi [Inorganica Chimica Acta, 2021, vol. 522]

87
tert-butyl 3-(6-fluoropyridin-3-yl)azetidine-1-carboxylate [ No CAS ]
[ 29364-29-2 ]
tert-butyl 3-(6-tert-butylsulfanyl-3-pyridyl)azetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	In dimethyl sulfoxide at 100℃; for 72h; Inert atmosphere;	2 Step 2: tert-Butyl 3-(6-tert-butylsulfanyl-3-pyridyl)azetidine-1-carboxylate To a solution of tert-butyl 3-(6-fluoro-3-pyridyl)azetidine-1-carboxylate (555.6 mg, 1.98 mmol, 1.0 equiv) in DMSO (8.9 mL) was added sodium 2-methyl-2-propanethiolate (222.3 mg, 1.98 mmol, 1.0 equiv; CAS RN 29364-29-2) and the reaction mixture was heated at 100 °C for 2 d. Again, sodium 2-methyl-2-propanethiolate (333.5 mg, 2.97 mmol, 1.5 equiv; CAS RN 29364- 29-2) was added and heating at 100 °C continued for 1 d. The reaction mixture was poured on water and extracted with ethyl acetate, the organic phase washed with water and dried over MgSO4and then concentrated. The crude compound was purified by silica gel chromatography using a MPLC system eluting with a gradient of n-heptane : ethyl acetate (100 : 0 to 70 : 30) to give the title compound as an orange oil (121 mg, 19 %). MS (ESI): m/z = 323.2 [M+H]+.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2022/49134, 2022, A1 Location in patent: Page/Page column 91; 213

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	29364-29-2	MDL No. :	MFCD00043311
Formula :	C₄H₉NaS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	TUZFIWBNGKNFPW-UHFFFAOYSA-M
M.W :	112.17	Pubchem ID :	5147913
Synonyms :

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	27.69
TPSA :	0.0 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.92 cm/s

[ CAS No. 29364-29-2 ] {[proInfo.proName]}

Quality Control of [ 29364-29-2 ]

Related Doc. of [ 29364-29-2 ]

Product Details of [ 29364-29-2 ]

Calculated chemistry of [ 29364-29-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 29364-29-2 ]

Application In Synthesis of [ 29364-29-2 ]

[ 29364-29-2 ] Synthesis Path-Upstream 1~2

[ 29364-29-2 ] Synthesis Path-Downstream 1~87

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	-10.24
Log Po/w (XLOGP3) :	1.5
Log Po/w (WLOGP) :	1.33
Log Po/w (MLOGP) :	1.82
Log Po/w (SILICOS-IT) :	0.87
Consensus Log Po/w :	-0.94

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.48
Solubility :	3.71 mg/ml ; 0.0331 mol/l
Class :	Very soluble
Log S (Ali) :	-1.11
Solubility :	8.75 mg/ml ; 0.078 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.1
Solubility :	8.85 mg/ml ; 0.0789 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.43

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3263
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling