Name: 1074-36-8|4-Mercaptobenzoic acid|95%
Brand: Ambeed
SKU: A293197
Price: 18.0 USD
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1
[ 67-56-1 ]
[ 1074-36-8 ]
[ 6302-65-4 ]

Yield	Reaction Conditions	Operation in experiment
97.7%	With sulfuric acid;Reflux;	To a solution of <strong>[1074-36-8]4-mercapto benzoic acid</strong> (5 g, 32.4 mmol) in methanol (25 mL) was added catalytic H2SO4 (1-2 drops) and refluxed for 5-6 h. TLC (mobile phase-10% methanol in chloroform Rf. S.M.-0.2, product-0.6) shows absence of starting material and formation of product; the methanol was distilled off in vacuo and the residue was diluted with ethyl acetate. The organic layer was washed with water (2×25 mL) followed by 10% aq. sodium bicarbonate solution. The organic layer was dried over Na2SO4 and concentrated in vacuo to obtained the product as an off-white solid (Yield-5 g). (0429) Yield: 97.7% (0430) HPLC Purity: 97.08% (0431) 1H NMR: Consistent with structure (0432) LCMS: MH+: 169 (Mol. Wt. 168)
95%	With sulfuric acid; at 90℃; for 24h;	General procedure: Esters 7-8 and 10-11 were prepared according to modified literature methods [27,28].The carboxylic acid (6 or 9) was dissolved in either methanol (30 mL) or ethanol (30 mL), with 2 dropsof concentrated sulfuric acid added to the solution before refluxing at 90 C for 24 h. The reactionprogress was monitored by TLC (cyclohexane-ethyl acetate; 1:1). The reaction was concentrated underreduced pressure to yield a white solid.Methyl-p-mercaptobenzoate (7)The residue was purified with column chromatography (cyclohexane-ethyl acetate; 3:1) to producea white solid. Yield: 319 mg, 95%. The NMR data were in agreement with those reported inliterature [27,28]. 1H-NMR (400 MHz, CDCl3, delta ppm): 7.88 (d, J = 8.6 Hz, 2H, CH), 7.27 (d, J = 8.6 Hz,2H, CH), 3.89 (s, 3H, CH3), 3.60 (s, 1H, SH). 13C-NMR (101 MHz, CDCl3, delta ppm): 166.9 (C=O), 138.3(CH), 130.2 (CH), 128.1 (CH), 127.1 (CH), 52.0 (CH3).
86%	With sulfuric acid; In chloroform; at 75℃;	Sulfuric acid (1.6mL) was added drop wise to a mixture comprising 4-sulfanylbenzoic acid (1.6g, 10.4 mmol), methanol (2.52 mL, 62.2 mmol) and chloroform (6.4mL). The mixture was stirred overnight at 75C, and the solution was extracted with chloroform. The organic layer was washed with aqueous saturated NaHC03, dried over MgSC^, and the solvent was evaporated to afford methyl 4-sulfanyl benzoate compound as a yellow solid in 86% yield.The compounds were confirmed using 1H and 13C NMR with the following spectral information:1H NMR (CD3OD): delta = 7.96-7.93 (m, 2H), 7.52-7.49 (m, 2H), 3.88 (s, 3H), 3.17 (s, 1H); 13C (CD3OD): delta = 165.44, 144.12, 129.27, 127.77, 124.97, 51.19

	With thionyl chloride; at 0℃; for 10h;Heating / reflux;	Thionyl chloride (3.7 mL) was added to a suspension of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (5.14 g) in methanol (30 mL) under cooling with ice, followed by heating under reflux for ten hours. After cooling, the precipitated crystals were collected by filtration, washed with methanol, and dried to yield a crystalline product (3.70 g). A mixture of the resulting crystals (0.17 g), the compound (0.24 g) obtained in Step 3 of Example 1, anhydrous potassium carbonate (0.70 g) and anhydrous dimethylformamide (1.0 mL) was stirred at 100 to 110C under nitrogen atmosphere for twenty hours. The reaction mixture was poured into an ice water (10 mL) and was extracted with ethyl acetate. The combined organic layer was washed with brine and was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography [Chromatorex NH] (eluent; hexane:ethyl acetate = 1:1) to yield the titled compound (0.25 g) as crystals.
	With thionyl chloride; N,N-dimethyl-formamide; at 0 - 20℃; for 2.08333h;Heating / reflux;	Dimethylformamide (ten drops) was added to a suspension of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (5.0 g) in methanol (32 mL), followed by dropwise addition of thionyl chloride (3.5 mL) under cooling with ice-water. The mixture was stirred at room temperature for five minutes and was heated under reflux for two hours. Insoluble matter was collected by filtration, washed with methanol, and dried to yield crystals (4.50 g). Anhydrous potassium carbonate (4.34 g) was added to a solution of the crystals (2.00 g) and 1-(tert-butoxycarbonyl)piperidine-4-spiro-2'-oxirane (2.23 g) in 4-methyl-2-pentanone (26 mL), followed by heating under reflux under nitrogen atmosphere for nine hours. The reaction mixture was mixed with an ice water (50 mL) and was extracted with ethyl acetate. The organic layer was sequentially washed with water and brine and was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography [Chromatorex NHTM] (eluent; hexane:ethyl acetate = 19:1 to 1:1), and crystallized from a 5:1 mixture of hexane and ether to yield the titled compound (2.55 g) as crystals.

Reference： [1]Patent: US9212151,2015,B2 .Location in patent: Page/Page column 100
[2]Molecules,2018,vol. 23
[3]Organic Letters,2017,vol. 19,p. 4150 - 4153
[4]Bulletin of the Chemical Society of Japan,2008,vol. 81,p. 361 - 368
[5]Patent: WO2012/152943,2012,A1 .Location in patent: Page/Page column 16
[6]RSC Advances,2020,vol. 10,p. 15726 - 15733
[7]Chemistry - A European Journal,2018,vol. 24,p. 818 - 821
[8]Journal of Organic Chemistry,1951,vol. 16,p. 810,812
[9]Journal of the Chemical Society,1963,p. 1947 - 1954
[10]Patent: EP1568688,2005,A1 .Location in patent: Page/Page column 44
[11]Patent: EP1568688,2005,A1 .Location in patent: Page/Page column 45
[12]Journal of Organic Chemistry,2008,vol. 73,p. 8057 - 8068

2
[ 10130-89-9 ]
[ 1074-36-8 ]

Reference： [1]Journal of the Chemical Society,1942,p. 376
[2]Journal of the Chemical Society,1922,vol. 121,p. 2024

3
[ 1155-51-7 ]
[ 1074-36-8 ]

Yield	Reaction Conditions	Operation in experiment
38%	With acetic acid; zinc for 4h; Heating;
	With triphenylphosphine In 1,4-dioxane; water at 30℃;
	With sodium carbonate; aluminium

	With sodium hydroxide; sodium dithionite
	With iron; sodium carbonate
	With hydrogenchloride; acetic acid; zinc
	With acetic acid; zinc
	Multi-step reaction with 2 steps 1: HCl / 1.)reflux, 2 h 2.)r.t., 18 h 2: 42 percent / Zn/AcOH / 4 h / Heating
	With hydrogenchloride; zinc In water Inert atmosphere; Cooling with ice;
	Multi-step reaction with 2 steps 1: aq. phosphate buffer; dimethyl sulfoxide / 0.5 h 2: GLUTATHIONE / pH 7.4
	With acetic acid; zinc

Reference： [1]Werbel; Newton; Elslager [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 3, p. 497 - 500]
[2]Overman,L.E. et al. [Journal of the American Chemical Society, 1974, vol. 96, # 19, p. 6081 - 6089]
[3]Buechi,J. [Diss. <E.T.H. Zuerich 1929> S. 90, 91]
[4]Hopper; MacGregor; Wilson [Journal of the Society of Dyers and Colourists, 1941, vol. 57, p. 6,7]
[5]Thompson [Journal of the Society of Chemical Industry, 1925, vol. 44, p. 196 T][Chemisches Zentralblatt, 1925, vol. 96, # II, p. 172]
[6]Pierson et al. [Journal of Polymer Science, 1955, vol. 17, p. 221,233]
[7]Gialdi et al. [Farmaco, Edizione Scientifica, 1959, vol. 14, p. 216,232] Brown et al. [Journal of the American Chemical Society, 1958, vol. 80, p. 4964,4967]
[8]Werbel; Newton; Elslager [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 3, p. 497 - 500]
[9]Location in patent: experimental part Xu, Hua-Jian; Liang, Yu-Feng; Cai, Zhen-Ya; Qi, Hong-Xia; Yang, Chun-Yan; Feng, Yi-Si [Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2296 - 2300]
[10]Zheng, Yiwu; Shen, Yang; Meng, Xiaoting; Wu, Yaqi; Zhao, Yibing; Wu, Chuanliu [ChemMedChem, 2019, vol. 14, # 12, p. 1196 - 1203]
[11]Quadrelli, Paolo [Arkivoc, 2021, vol. 2021, # 8]

4
[ 1074-36-8 ]
[ 1155-51-7 ]

Yield	Reaction Conditions	Operation in experiment
99.5%		Synthesis of B; Compound A (25.0 g. 0.162 mol) was dissolved in methanol ( 100 ml) and triethylamine (23 ml). Then, to the resultant mixture, a 30% hydrogen peroxide aqueous solution (9 ml) was added dropwise, over 10 minutes, under cooling to 50C to 25C under stirring. The reaction liquid was stirred at 250C for additional 30 minutes, and concentrated hydrochloric acid ( 1 5 ml) was added dropwise into the reaction liquid cooled to 50C to 250C under stirring. Then, water (200 ml ) was added thereto, and the whole was stirred at 250C for 1 hour. The thus-precipitated crystals w ere filtered and sufficiently washed with water. The thus-obtained crystals were dried, to thereby obtain EPO <DP n="72"/>white crystals of B (24.7 g. yield 99.5%).
80%		The <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (0.53 g; 3.4 mmol) and Iodine (0.44g; 1.7 mmol) were dissolved in 10 ml of ethanol. Triethylamine (1.5ml; 10.2 mmol) was added and the solution was stirred overnight (16h).The excess of iodine was removed with the addiction of a 10% solution of sodium thiosulfate . The cloudy solution was concentrated and combined with HCl 0,01 M till the pH became acid.The pallid yellow precipitate was collected, dried under vacuum and washed with petroleum ether. <n="20"/>This step did not need further purification.YIELD: 80%
41.6%	With iodine; In ethanol; at 20℃;	After iodine was dissolved to be saturated in 95% ethanol, the solution was slowly added dropwise at room temperature to a solution of <strong>[1074-36-8]4-mercapto benzoic acid</strong> (500 mg, 3.24 mmol) dissolved in ethanol (32 ml). As the reaction proceeded, the reddish brown color of iodine disappeared and crystals were formed, and the iodine was continuously added until the yellow color of the reacted solution no longer disappeared. The generated soli was filtered, and washed with ethanol. The filtered crystals were dried at 50 C. in vacuo to give a gray solid of 4,4'-disulfanediyldibenzoic acid (413 mg, 1.348 mmol, 41.6%). 1H-NMR (DMSO-d6, Varian 400 MHz): delta7.64 (4H, d, J=7.6 Hz), 7.93 (4H, d, J=8.0 Hz), 13.06 (2H, s)

Reference： [1]Patent: WO2007/37039,2007,A1 .Location in patent: Page/Page column 70-71
[2]Journal of the American Chemical Society,2005,vol. 127,p. 8036 - 8043
[3]Green Chemistry,2019,vol. 21,p. 1432 - 1438
[4]New Journal of Chemistry,2003,vol. 27,p. 1115 - 1123
[5]Inorganic Chemistry,2016,vol. 55,p. 12982 - 12996
[6]Inorganic Chemistry,2018,vol. 57,p. 2736 - 2743
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[9]Journal of the American Chemical Society,2016,vol. 138,p. 14206 - 14209
[10]Journal of Molecular Catalysis B: Enzymatic,2016,vol. 126,p. 106 - 114
[11]Patent: US2018/327357,2018,A1 .Location in patent: Paragraph 0163; 0164
[12]Journal of the American Chemical Society,2013,vol. 135,p. 10314 - 10317
[13]Green Chemistry,2017,vol. 19,p. 4061 - 4066
[14]Journal of the Chemical Society,1922,vol. 121,p. 2024
[15]Journal of the Chemical Society,1922,vol. 121,p. 2024
[16]Thermochimica Acta,2010,vol. 502,p. 51 - 59
[17]Chemical Communications,2011,vol. 47,p. 893 - 895
[18]Journal of Physical Chemistry A,2010,vol. 114,p. 12010 - 12015
[19]Chemical Communications,2014,vol. 50,p. 3716 - 3718
[20]Chemical Communications,2017,vol. 53,p. 5706 - 5709
[21]Angewandte Chemie - International Edition,2019,vol. 58,p. 14303 - 14310
Angew. Chem.,2019,vol. 131,p. 14441 - 14448,8

5
[ 34662-31-2 ]
[ 1074-36-8 ]
[ 74761-53-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With triethylamine In acetone for 0.25h;

Reference： [1]Werbel; Newton; Elslager [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 3, p. 497 - 500]

6
[ 50-00-0 ]
[ 1074-36-8 ]
[ 619-26-1 ]
4-[Methyl-(3-nitro-phenyl)-amino]-methylsulfanyl}-benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 80℃; for 2h;

Reference： [1]Eldin, Sherif; Jencks, William P. [Journal of the American Chemical Society, 1995, vol. 117, # 17, p. 4851 - 4857]

8
[ 7647-01-0 ]
[ 10130-89-9 ]
[ 64-19-7 ]
zinc [ No CAS ]
[ 1074-36-8 ]

Reference： [1]Journal of the Chemical Society,1922,vol. 121,p. 2024

9
[ 1074-36-8 ]
[ 107-07-3 ]
[ 7184-99-8 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium hydroxide; In methanol; at 25 - 30℃; for 4h;Reflux;	Example 84; Preparation of S-[4-(N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]-4-chlorophenyl}carbamoyl)phenyl]-S-{(2-diethylamino)ethyl}sulfoximideStep 1 Preparation of 4-(2-Hydroxy-ethylsulfanyl)-benzoic acidTo a stirred solution of <strong>[1074-36-8]4-mercapto benzoic acid</strong> (10 g, 0.0645 mmol) in methanol (100 mL) was added KOH (10.8 g, 0.1935 mol) at 25-30 C. Chloroethanol (10.3 g, 0.1290 mol) was then added to it. Reaction mixture was refluxed for 4 hr. Excess methanol was evaporated and then quenched in dil.HCl. Product obtained was filtered. Drying afforded 8 g of titled compound in 62% yield.
		To a solution of 400 mg of 4-thiobenzoic acid in 2.85 ml of NaOH · 2N, 0.160 ml of 2-chloroethanol were added. The solution was refluxed for 1 hour, 2.85 ml of hydrochloric acid 2N were then added dropwise and the precipitated was filtered and dried yielding 370 mg of a white solid. FAB-MS: m/z 220, (60, (M+H]+)PMR (CDCl3) d:7.61 (d, J= 15.7 Hz, 1H), 7.33 (m, 2H), 6.55 (m, 2H), 6.21 (d, J= 15.7 Hz, 1H), 4.22 (q, J=7.1 Hz, 2H), 3.9 (b.s., 1H), 3.19 (q, J=7.1 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H), 1.28 (t, J=7.1 Hz, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1653 - 1656
[2]Patent: US2011/65717,2011,A1 .Location in patent: Page/Page column 20
[3]Patent: EP1100778,2004,B1 .Location in patent: Page 10

10
[ 1074-36-8 ]
[ 53339-53-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 16.5h;Inert atmosphere; Reflux;	4gLiAlH4 was added to 50 ml of tetrahydrofuran to form a suspension, N2 was protected, 8.5 g of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> was dissolved in 100 ml of tetrahydrofuran,Slowly added dropwise to the above suspension. After stirring, stirring was continued for 30 minutes, then the temperature was raised to reflux and stirred for 16 hours.After completion of the reaction, 40 ml of ethyl acetate and 50 ml of 15% H2SO4 solution were added and the mixture was filtered and the aqueous phase was extracted with 50 ml of ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to give 7.5 g of pale yellow or Colorless liquid. Purification by gelatin column chromatography (ethyl acetate: petroleum ether = 75: 25) gave 7.1 g of a white solid, yield 93%.
67%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 17h;	Lithium aluminum hydride (4.766 g, 125.6 mmol) was added to a solution of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (1, 9.682 g, 62.79 mmol) in 100 mL THF and stirred for 17 h at rt. The reaction mixture was quenched with 2 M HCl to pH 2. The aqueous solution was extracted with diethylether (3 × 50 mL). The organic solution was dried by anhydrous sodium sulfate, filtered, and evaporated to give 4-mercaptobenzyl alcohol (2) as a white solid (5.873 g, 67%), mp 56-60C. 1H NMR (CDCl3, 300 MHz): delta 2.14 (broad s, 1H), 3.46 (s, 1H), 4.63 (s, 2H), 7.21-7.28 (m, 4H). 13C NMR (CDCl3, 75 MHz): delta 65.1, 128.1, 129.9, 130.3, 138.7.
66%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 12h;Inert atmosphere;	To a stirrer solution of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (2.0 g, 13 mmol) in THF dry (25 mL) in a three-neck flask under N2 atmosphere, L1AIH4 1 M in THF (39 mL, 39 mmol) is added at 0 C in 30'. The mixture is left to stir at rt for 12 hours. Then, the reaction is cooled at 0 C, quenched with 3 mL of water and acidified to pH 2 with HCI 1 M. Ethyl acetate is added and the organic layer washed with H2O and brine, dried over anhydrous sodium sulfate, filtered and the solvent removed by rotatory evaporation. The resulting residue is purified by flash column chromatography with a medium pressure system Sepacore Buchi (silica gel; gradient petroleum ether/ethyl acetate B% 0-25 in 3 minutes, 25-25 in 6', 25-100 in 3') to give alcohol [36] (1 .2 mg, yield 66%) as a yellow solid. MS: m/z 141 .2 [M+H]+ 1H NMR (400 MHz, CDCIs) delta 7.25 - 7.06(m, 4H), 4.43 (s, 2H), 3.72 (s, 1 H), 3.48 (s, 1 H).

54%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃;Inert atmosphere;	Lithium aluminum (740 mg, 19.4 mmol) was suspended in 15 mL of tetrahydrofuran,Under nitrogen protection, keep at 0 .A solution of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (1.0 g, 6.48 mmol) in tetrahydrofuran (15 mL) was slowly added dropwise to the lithium aluminum hydride tetrahydrofuran system, and the mixture was kept overnight.After quenching the reaction with 0.5 mL of water, the pH was adjusted to 2 with 2M hydrochloric acid, and extraction was performed with ethyl acetate.The organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.Purification on a silica gel column gave 4-mercaptobenzyl alcohol (440 mg, 54%).
54%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃;Inert atmosphere;	Lithium aluminum hydride (1.5 g, 38.8 mmol) was suspended in 30 mL of tetrahydrofuran, and the temperature was maintained at 0 C under the protection of nitrogen.A solution of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (2.0 g, 12.96 mmol) in tetrahydrofuran (20 mL) was slowly added dropwise to the lithium aluminum hydride tetrahydrofuran system, and the mixture was kept overnight.The reaction was quenched with 1.0 mL of water, the pH was adjusted to about 2 with 2M hydrochloric acid, and extracted with ethyl acetate.The organic phase was washed with water, saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.Purification by silica gel column chromatography gave 4-mercaptobenzyl alcohol (880 mg, 54%).
44%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 96h;Cooling with ice; Inert atmosphere;	After LiAlH4 (5.51 g, 145 mmol) was added to dry tetrahydrofuran (THF, 170 mL), the mixture was stirred slightly under ice-cooling, and the inside of the reaction vessel was replaced with argon.Thereafter, a THF solution (130 mL) of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (7.57 g, 49.1 mmol) was added, and the mixture was stirred for 4 days.The reaction was stopped by adding a saturated aqueous solution of ammonium chloride, methanol was added, and then ultrasonic vibration was applied to dissolve the rattan oily substance, which was then dissolved with celite.After concentration under reduced pressure, ethyl acetate was added, and the mixture was washed twice with water and once with a saturated aqueous solution of sodium chloride.Collect the organic phase, dry over anhydrous sodium sulfate and filter the solution.After being obtained, it was concentrated under reduced pressure.Silica gel chromatography of the residue (hexane: acetic acid(Developed with chill = 1: 1, eluted with chloroform: methanol = 100: 0))There was obtained (4-mercaptophenyl) methanol (3.05 g, 21.8 mmol, yield 44%) as a white solid.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 16h;	<strong>[1074-36-8]4-mercaptobenzoic acid</strong> (10.0 g, 64.9 mmol) was added to a solution of lithium aluminum hydride (3.69 g, 97.3 mmol) in THF (500 ml) at 0 C. The mixture was then warmed to room temperature and stirred for 16 h, then quenched with 2M HC1 to pH = 2. The aqueous solution was extracted with diethyl ether (3 x 500 mL), the combined organic layers dried with sodium sulfate, and the solvent removed in vacuo to give 8A, which was used without further purification (6.70 g, 43% purity, 20.6 mmol, 31% yield).
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 16h;	<strong>[1074-36-8]4-mercaptobenzoic acid</strong> (10.0 g, 64.9 mmol) was added to a solution of lithium aluminum hydride (3.69 g, 97.3 mmol) in THF (500 ml) at 0 C. The mixture was then warmed to room temperature and stirred for 16 h, then quenched with 2M HC1 to pH = 2. The aqueous solution was extracted with diethyl ether (3 x 500 mL), the combined organic layers dried with sodium sulfate, and the solvent removed in vacuo to give 17D, which was used without further purification (6.70 g, 43% purity, 20.6 mmol, 31% yield).

Reference： [1]Patent: CN103910663,2016,B .Location in patent: Paragraph 0064-0066
[2]Chemical Communications,2015,vol. 51,p. 5721 - 5724
[3]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6233 - 6236
[4]Patent: WO2018/178060,2018,A1 .Location in patent: Page/Page column 86-88
[5]Journal of the American Chemical Society,2017,vol. 139,p. 4009 - 4018
[6]Angewandte Chemie - International Edition,2017,vol. 56,p. 3206 - 3210
Angew. Chem.,2017,vol. 129,p. 3254 - 3258,5
[7]Patent: CN110314235,2019,A .Location in patent: Paragraph 0040; 0044-0045; 0054
[8]Patent: CN110314238,2019,A .Location in patent: Paragraph 0043; 0047-0048; 0057
[9]Journal of Organic Chemistry,2001,vol. 66,p. 4244 - 4249
[10]Patent: JP2019/196349,2019,A .Location in patent: Paragraph 0084
[11]Bioorganic and medicinal chemistry letters,2020,vol. 30
[12]Journal of the Chemical Society,1963,p. 1947 - 1954
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[14]Patent: WO2018/112176,2018,A1 .Location in patent: Paragraph 00386
[15]Chemical Communications,2018,vol. 54,p. 13252 - 13255
[16]Patent: WO2019/118830,2019,A1 .Location in patent: Paragraph 0343; 0352

11
[ 10419-77-9 ]
[ 1074-36-8 ]
[ 634158-87-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃; for 6h;

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

12
[ 6705-49-3 ]
[ 1074-36-8 ]
[ 681824-23-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	In water at 30℃; for 1h;

Reference： [1]Fringuelli, Francesco; Pizzo, Ferdinando; Vaccaro, Luigi [Journal of Organic Chemistry, 2004, vol. 69, # 7, p. 2315 - 2321]

13
[ 10276-21-8 ]
[ 1074-36-8 ]
3,5,5-trimethyl-2-(4-carboxyphenylthio)cyclohex-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water at 30℃; for 1h;

Reference： [1]Fringuelli, Francesco; Pizzo, Ferdinando; Vaccaro, Luigi [Journal of Organic Chemistry, 2004, vol. 69, # 7, p. 2315 - 2321]

14
[ 1074-36-8 ]
[ 50916-55-7 ]
[ 722516-86-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In ethanol Heating / reflux;	Preparation of 4- { [2- (3-CYANOPHENYL)-2-OXOETHYL] THIO} BENZOIC acid (VIB 385) To 3-cyanobromoacetophenone (363.3 mg, 1.62 mmole) and anhydrous K2CO3 (896 mg, 6. 48 mmole) in ethanol (20 ml), 250 mg (1.62 mmole) 4-mercaptobenzoic acid was added and the mixture refluxed overnight. The solvent was evaporated and water added to the solid residue. The basic aqueous solution was extracted with ethyl acetate to remove unreacted bromoacetophenone. The aqueous layer was acidified to yield a precipitate which was filtered and dried (377 mg). The solid was further purified by flash chromatography (CHC13 : CH30H 99: 1 to 95: 5. The homogeneous fractions were pooled and evaporated to yield product (110 mg). m/z 296 (M-1) +'HNMR (DMSO) 8 4.9 (2H, s,- CH2-), 7.44 (2H, d, 2xArH), 7.63 (1H, d, ArH), 7.76 (1H, t, ArH), 7.83 (2H, d, 2xArH), 7.93 (1H, d, ArH), 8.13 (1H, d, ArH), 8.29 (1H, d, ArH), 8.54 (1H, d, ArH).

Reference： [1]Current Patent Assignee: THE BURNET INSTITUTE - WO2004/58747, 2004, A1 Location in patent: Page 48

15
[ 53595-65-6 ]
[ 1074-36-8 ]
[ 900814-30-4 ]

Yield	Reaction Conditions	Operation in experiment
		INTERMEDIATE 30; This shows the preparation of 4-[5-(aminosulfonyl)-2-thienyl]thio}benzoic acid.To a solution of 5-bromothiophene-2-sulfonamide (242 mg) and 4-mercaptobenzoic acid (154 mg) in DMF (1 mL) was added aqueous 2 N sodium hydroxide solution (1 mL). The reaction mixture was heated in a CEM Discover microwave at 150C for 25 min. After this time it was allowed to cool, then it was diluted with water (20 mL) and acidified with 10 % v/v aqueous hydrochloric acid. The fine precipitate that formed was difficult to filter so the EPO <DP n="47"/>majority of the liquid was decanted from the solid, and the gelatinous residue concentrated to dryness in vacuo to give the title compound 4-[5-(aminosulfonyl)-2- thienyl]thio}benzoic acid (280mg).1H NMR (300 MHz, DMSO) δ 13.03 (s, 1H), 7.91 (d, 2H), 7.85 (s, 2H), 7.59 (d, 1H), 7.50 (d, 1H), 7.34 (d, 2H).
	With sodium hydroxide; In water; N,N-dimethyl-formamide; at 150℃; for 0.416667h;Microwave;	This shows the preparation of 4-[5-(aminosulfonyl)-2-thienyl]thio}benzoic acid.I0 To a solution of 5-bromothiophene-2-sulfonamide (242 mg) and 4-mercaptobenzoic acid (154 mg) in DMF (1 mL) was added aqueous 2 N sodium.hydroxide solution (1 mL). The reaction mixture was heated in a CEM Discover microwave at 1500C for 25 min. After this time it was allowed to cool, then it was diluted with water (20 mL) and acidified with 10% v/v aqueous hydrochloric acid. The fine precipitate that formed was difficult to filter is so the majority of the liquid was decanted from the solid, and the gelatinous residue concentrated to dryness in vacuo to give the title compound 4-[5-(aminosulfonyl)-2- thienyl]thio}benzoic acid (280 mg).1HNMR (300 MHz, DMSO) δ 13.03 (s, IH), 7.91 (d, 2H), 7.85 (s, 2H), 7.59 (d, IH), 7.50 (d, IH), 7.34 (d, 2H).

Reference： [1]Patent: WO2006/75955,2006,A1 .Location in patent: Page/Page column 45-46
[2]Patent: WO2006/85815,2006,A1 .Location in patent: Page/Page column 42

16
[ 1074-36-8 ]
[ 6302-65-4 ]

Yield	Reaction Conditions	Operation in experiment
712 mg (Y: 38%)	With sulfuric acid; In methanol;	EXAMPLE 112 Methyl 4-mercaptobenzoate STR108 To a solution of 4-mercaptobenzoic acid (Apin, 1.72 g, 11.17 mmol) in anhydrous methyl alcohol (20.0 mL) was added concentrated sulfuric acid (0.43 mL). The reaction mixture is then warmed to reflux for 16 h, concentrated in vacuo, diluted with ethyl acetate (100 mL) and washed with saturated sodium bicarbonate (2*100 mL). The organic phase is then separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 712 mg (Y: 38%) of the title product; 1 H-NMR (CDCl3): delta7.89 (d, J=8.7 Hz, 2H), 7.29 (d, J=8.7 Hz, 2H), 3.90 (s, 3H), 3.60 (s, 1H).
712 mg (Y: 38%)	With sulfuric acid; In methanol;	EXAMPLE 112 Methyl 4-mercaptobenzoate STR108 To a solution of 4-mercaptobenzoic acid (Apin, 1.72 g, 11.17 mmol) in anhydrous methyl alcohol (20.0 mL) was added concentrated sulfuric acid (0.43 mL). The reaction mixture is then warmed to reflux for 16 h, concentrated in vacuo, diluted with ethyl acetate (100 mL) and washed with saturated sodium bicarbonate (2*100 mL). The organic phase is then separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 712 mg (Y: 38%) of the title product; 1 H-NMR (CDCl3): delta 7.89 (d, J=8.7 Hz, 2H), 7.29 (d, J=8.7 Hz, 2H), 3.90 (s, 3H), 3.60 (s, 1H).

Reference： [1]Patent: US5618839,1997,A
[2]Patent: US5648385,1997,A
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 8885 - 8889
Angew. Chem.,2014,p. 9031 - 9035,5
[4]ChemMedChem,2018,vol. 13,p. 1353 - 1362

17
conc. H₂ SO₄ [ No CAS ]
4-[2[(t-butyldimethylsilyloxy)-ethyl]thio]benzoic acid [ No CAS ]
[ 1074-36-8 ]
[ 101166-65-8 ]
[ 160743-68-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; In methanol; N,N-dimethyl-formamide;	A solution of 4-mercaptobenzoic acid (5.09 g, 33 mmol) in DMF (60 ml) was added to a slurry of 60percent NaOH (2.64 g, 66 mmol) in DMF (60 ml) under argon at 0° C. This mixture was stirred at 0° C. for 90 minutes prior to the dropwise addition of a solution of 1-(tert.-butyldimethylsilyloxy)-2-iodoethane (8.59 g, 30 mmol) in DMF (30 ml). The resultant reaction mixture was stirred for 3 hours at room temperature, then poured over a mixture of 0.5N HCl (70 ml) and ice (200 g) and diluted with water (500 ml). The precipitate that formed was collected by filtration to give a peach-colored solid (9.28 g, 99percent yield) which was used without further purification. The above product 4-[2[(t-butyldimethylsilyloxy)-ethyl]thio]benzoic acid (8.75 g, 28 mmol) was dissolved in CH3 OH (300 ml) containing conc. H2 SO4 (3 ml) and this solution was refluxed overnight. The solvent was removed by concentration, in vacuo, and the residue was partitioned between saturated NaHCO3 (300 ml) and ether (300 ml). The layers were separated and the aqueous phase extracted with EtOAc (200 ml). The combined organic extracts were dried over Na2 SO4 and concentrated, in vacuo, to give an orange gum which was purified by flash chromatography. Elution with hexane/EtOAc (2:1) yielded the product as a white solid (3.53 g, 59percent yield) which melted at 58° C. The following analyses indicate that that product was methyl 4-(2-hydroxyethyl)thio benzoate: NMR(CDCL3) delta=7.94(2H, d, J=8.5 Hz), 7.36(2H,, d J=8.5 Hz), 3.90(3H, s), 3.83(2H, q, J=6.1 Hz), 3.21 (2H, t, J=6.1 Hz), 1.96(1H, t, J=6.1 Hz)

Reference： [1]Patent: US5726312,1998,A

18
conc. H₂ SO₄ [ No CAS ]
4-[2[(t-butyldimethylsilyloxy)ethyl]thio]benzoic acid [ No CAS ]
[ 1074-36-8 ]
[ 101166-65-8 ]
[ 160743-68-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; In methanol; N,N-dimethyl-formamide;	A solution of 4-mercaptobenzoic acid (5.09 g, 33 mmol) in DMF (60 ml) was added to a slurry of 60percent NaOH (2.64 g, 66 mmol) in DMF (60 ml) under argon at 0° C. This mixture was stirred at 0° C. for 90 minutes prior to the dropwise addition of a solution of 1-(tert.-butyldimethylsilyloxy)-2-iodoethane (8.59 g, 30 mmol) in DMF (30 ml). The resultant reaction mixture was stirred for 3 hours at room temperature, then poured over a mixture of 0.5N HCl (70 ml) and ice (200 g) and diluted with water (500 ml). The precipitate that formed was collected by filtration to give a peach-colored solid (9.28 g, 99percent yield) which was used without further purification. The above product 4-[2[(t-butyldimethylsilyloxy)ethyl]thio]benzoic acid (8.75 g, 28mmol) was dissolved in CH3 OH (300 ml) containing conc. H2 SO4 (3 ml) and this solution was refluxed overnight. The solvent was removed by concentration, in vacuo, and the residue was partitioned between saturated NaHCO3 (300 ml) and ether (300 ml). The layers were separated and the aqueous phase extracted with EtOAc (200 ml). The combined organic extracts were dried over Na2 SO4 and concentrated, in vacuo, to give an orange gum which was purified by flash chromatography. Elution with hexane/EtOAc (2:1) yielded the product as a white solid (3.53 g, 59percent yield) which melted at 58° C. The following analyses indicate that that product was methyl 4-(2-hydroxyethyl)thio benzoate: NMR(CDCL3) delta=7.94(2H, d, J=8.5 Hz), 7.36(2H, d, J=8.5 Hz), 3.90(3H, s), 3.83(2H, q, J=6.1 Hz), 3.21 (2H, t, J=6.1 Hz), 1.96(1H, t, J=6.1 Hz)

Reference： [1]Patent: US5739141,1998,A

19
[ 926293-55-2 ]
[ 1074-36-8 ]
[ 926643-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;	A mixture of <strong>[926293-55-2]6-bromo-2-methylpyridine-3-carboxaldehyde</strong> (0.400 g, 2.00 mmol), 4- mercapto-benzoic acid (0.463 g, 3.00 mmol) and K2CO3 (0.414 g, 3.00 mmol) in DMF (5 mL) was stirred at room temperature for 3 h. CH3I (1.13 g, 8.00 mmol) and another portion of K2CO3 (0.414 g, 3.00 mmol) were added, and the mixture was stirred for another 2 h. Aqueous work-up and purification by flash chromatography on silica gel (CH2Cl2) afforded 4-(5-formyl- 6-methyl-pyridin-2-ylsulfanyl)-benzoic acid methyl ester as a pale yellow solid (0.487 g, 85%). 1H NMR (CDCl3) 52.81 (s, 3H), 3.96 (s, 3H), 6.85 (d, IH, J= 8.1 Hz), 7.67-7.70 (m, 2H), 7.85 (d, IH, J= 8.1 Hz), 8.09-8.13 (m, 2H), 10.22 (s, IH).

Reference： [1]Patent: WO2007/22371,2007,A2 .Location in patent: Page/Page column 58

20
[ 1074-36-8 ]
[ 4919-48-6 ]

Yield	Reaction Conditions	Operation in experiment
99.5%	With dihydrogen peroxide; triethylamine; In methanol; water; at 25℃; for 0.5h;	25.0 g (0.162 mol) of the compound A was dissolved in a mixed solvent of 100 mL of methanol and 23 mL of triethylamine. The resultant solution was cooled to 5 C, and 9 mL of a 30% hydrogen peroxide aqueous solution was dropwise added thereto while the solution of the compound A was stirred and the internal temperature was maintained at or under 25C. After the dropwise addition, the reaction solution was further stirred at 25 C for 30 minutes, and then cooled to 5 C again. While the solution was stirred, 15 mL of concentrated hydrochloric acid was dropwise added thereto. Thereafter, 200 mL of water was further added thereto, and the resultant solution was stirred at 25 C for 1 hour. The precipitated crystal was filtrated, washed sufficiently with water, and dried to yield 24.7 g of the intermediate product B as a white crystal (yield: 99.5%).

Reference： [1]Patent: EP1826200,2007,A2 .Location in patent: Page/Page column 162-163

21
[ 1074-36-8 ]
[ 107-14-2 ]
[ 405924-26-7 ]

Yield	Reaction Conditions	Operation in experiment
88%		4-(2H-Tetrazol-5-ylmethylsulfanyl)benzoic acid To a solution of sodium hydroxide (10.4 g, 0.26 mol) in degassed water (600 mL) was added <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (20.0 g, 0.13 mol). This solution was stirred for 30 minutes. To a solution of potassium carbonate (9.0 g, 65 mmol) in degassed water (400 mL) was added chloroacetonitrile (9.8 g, (0.13 mol) portion-wise. These two solutions were mixed and stirred for 48 hours at RT under N2. The mixture was filtered and washed with heptane. The aqueous phase was acidified with 3N hydrochloric acid and the product was filtered off, washed with water and dried, affording 4-cyanomethylsulfanylbenzoic acid (27.2 g, 88%).
88%		To a solution of sodium hydroxide (10.4 g, 0.26 mol) in degassed water (600 mL) was added <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (20.0 g, 0.13 mol). This solution was stirred for 30 minutes. To a solution of potassium carbonate (9.0 g, 65 mmol) in degassed water (400 mL) was added chloroacetonitrile (9.8 g, (0.13 mol) portion-wise. These two solutions were mixed and stirred for 48 hours at RT under N2. The mixture was filtered and washed with heptane. The aqueous phase was acidified with 3N hydrochloric acid and the product was filtered off, washed with water and dried, affording 4-cyanomethylsulfanylbenzoic acid (27.2 g, 88%).
		To a solution of sodium hydroxide (10.4 g, 0.26 rnol) in degassed water (600 mL) was added <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (20.0 g, 0.13 mol). This solution was stirred for 30 minutes. To a so¬ lution of potassium carbonate (9.0 g, 65 mmol) in degassed water (400 mL) was added chloroacetonitrile (9.8 g, (0.13 mol) portion-wise. These two solutions were mixed and stirred for 48 hours at RT under N2. The mixture was filtered and washed with heptane. The aque¬ ous phase was acidified with 3N hydrochloric acid and the product was filtered off, washed with water and dried, affording 4-cyanomethylsulfanylbenzoic acid (27.2 g, 88%). This com¬ pound was used without further purification in the following step.

Reference： [1]Patent: US2005/65066,2005,A1 .Location in patent: Page/Page column 142
[2]Patent: US2003/229120,2003,A1 .Location in patent: Page 93
[3]Patent: WO2006/5683,2006,A1 .Location in patent: Page/Page column 262

22
[ 15278-97-4 ]
[ 1074-36-8 ]
[ 346706-12-5 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,2001,p. 1058 - 1062

23
[ 15529-90-5 ]
[ 1074-36-8 ]
[ 346706-14-7 ]

Yield	Reaction Conditions	Operation in experiment
69%		H2mba (0.245?g, 1.58?mmol) was dissolved in a solution of KOH (0.089?g, 1.58?mmol) in 20?mL of ethanol (16?mL) and water (4?mL) and was stirred for 20?min at room temperature. [AuCl(PEt3)] was added to the solution afterwards, and the mixture was stirred for 2?h. The solvents were removed under reduced pressure, and the residue was washed with water (3 x 2?mL) and then diethyl ether (3??3?mL) to afford compound 3 as white powder in 69% yield (0.512?g). Anal. Calc. for C13H20AuO2PS (468.30): C, 33.34; H, 4.30; S, 6.85. Found: C, 33.04; H, 4.42; S, 6.40. 31P{1H} NMR (CDCl3): delta 36.92. 1H NMR (CDCl3): delta 7.79 (2H, d, 3JH-H?=?8.3?Hz, 2-C6H4), delta 7.60 (2H, d, 3JH-H?=?8.2?Hz, 3-C6H4), delta 1.88 (6H, m, -CH2CH3), delta 1.25 (9H, dt, 3JH-H?=?18.5, 7.6?Hz, -CH2CH3). 13C{1H} NMR (CDCl3): delta 171.90 (s, C=O), delta 153.05 (s, 4-C6H4), delta 132.34 (s, 2-C6H4), delta 130.02 (s, 3-C6H4), delta 124.05 (s, 1-C6H4), delta 18.46, (d, 3JC-P?=?33.3?Hz, -CH2CH3), delta 9.41 (s, -CH2CH3). IR (cm-1): 2962?m, br (OH), 1668?s, 1578?s (nuasym CO2), 1325?m, 1292 vs (nusym CO2), 1176?m, 1085?m, 760?m pH 2 (5??10-5?M in 1:99 DMSO:H2O)?=?4.53.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 161,p. 310 - 322
[2]Journal of the Chemical Society, Dalton Transactions,2001,p. 1058 - 1062

24
[ 1074-36-8 ]
[ 195455-54-0 ]
[ 943616-64-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	In ethanol; water at 80℃;	30.30a The product from Example 9a (0.94 g, 3.31 mmol) was reacted with 4-mercapto- benzoic acid (0.51 g, 3.31 mmol) in aqueous ethanol at 800C under nitrogen. The reaction mixture was poured into water and acidified with glacial acetic acid. The solid product was collected by filtration, water washed and dried in vacuo to give the title compound (0.877 g, 91 %) sufficiently pure for use as isolated.

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2008/133753, 2008, A2 Location in patent: Page/Page column 76

25
[ 67108-80-9 ]
[ 1074-36-8 ]
[ 1037687-66-3 ]

Reference： [1]Inorganic Chemistry,2008,vol. 47,p. 5815 - 5820

26
[ 447460-31-3 ]
[ 1074-36-8 ]
[ 447460-32-4 ]

Yield	Reaction Conditions	Operation in experiment
71%		Compound 42. 4-Mercaptobenzoic acid (0.54 g, 3.50 mmol) was dissolved in DMA (10 mL) and cooled in an ice bath. Sodium hydride (60% suspension in oil, 0.30 g, 7.5 mmol) was added and the reaction mixture was stirred for 20 min. The ice bath was removed and the reaction mixture was stirred for 1 h. The flask was cooled to 0 C. again and compound 41 (1.0 g, 3.46 mmol) dissolved in DMA (5 mL) was added. The reaction mixture was stirred at 0 C. for 30 min, then allowed to warm to rt and stirred overnight. The reaction mixture was diluted with CH2Cl2 and washed with 5% aq HCl, water, and brine. The organic layer was dried with Na2SO4 and the solvents were evaporated. The crude product was purified via sgc (5% MeOH/CH2Cl2) to give Coompound 42 as a solid (1.04 g, 71%).

Reference： [1]Patent: US2003/232859,2003,A1 .Location in patent: Page 47

27
[ 1074-36-8 ]
[ 53784-84-2 ]
6-perdeoxy-6-per(4-carboxyphenyl)thio-γ-cyclodextrin sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-mercaptobenzoic acid With sodium hydride In DMF (N,N-dimethyl-formamide) for 0.5h; Stage #2: octakis(6-bromo-6-deoxy)-γ-cyclodextrin In DMF (N,N-dimethyl-formamide) at 70℃; for 24h;	8 EXAMPLE 8; 6-Per-deoxy-6-per-(4-carboxyphenyl)thio-γ-cyclodextrin, Sodium Salt To a solution of 4-mercaptobenzoic acid (856 mg) in DMF (30 ml) was added 60% sodium hydride dispersed in oil (372 mg) portionwise over 30 min. The mixture was cooled and per-6-deoxy-per-6-bromo-γ-cyclodextrin (1.0 g) was added in one portion and the mixture was stirred at 70° C. for 24 h. The mixture was allowed to cool to room temperature and quenched with the addition of water (20 ml) before evaporating to a low volume. The solution was poured into ethanol (250 ml) and the precipitate was collected by filtration, dissolved in water (20 ml) and dialysed (MWCO 1000) by changing the external water four times. Internal solution was evaporated to low volume and poured into acetone (250 ml). The solid precipitate was collected by filtration and dried under vacuum at 70° C. to afford the title compound (1.2 g) as a white solid. 1H NMR (D2O, 343K) δ 7.70 (16H, d, J=8.1 Hz, Ar-H), 7.23 (16H, d, J=7.3 Hz, Ar-H), 5.15 (8H, s, CyD 1-H), 4.00-3.96 (16H, m, CyD 3,5-H), 3.55-3.53 (24H, m, CyD 6',4,2-H), 3.15 (8H, m, CyD 6-H); MALDI-TOF m/z 2383.7 for [M-Na8+H6], calcd for C104H104Na8O48S8 M 2562.39.

Reference： [1]Current Patent Assignee: MERCK & CO INC; ORGANON & CO - US6670340, 2003, B1 Location in patent: Page column 11

28
[ 1074-36-8 ]
[ 109-64-8 ]
[ 1001437-90-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine; In acetonitrile; at 0℃; for 3h;	Example 11 <n="36"/>[ (4-{ [3- (Nitrooxy) propyl] thio}benzoyl) oxy] methyl 2- (acetyloxy) benzoate: compound (11)4- [ (3-Bromopropyl) thio] benzoic acidTo a sospension of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> 90% (3.0 g, 17.50 mmol) in CH3CN (30 mL) , stirred at 0C, 1, 3-dibromopropane (9.0 mL, 87.50 mmol) and Et3N (5.00 mL, 35.0 mmol) were added. After 3 hours the reaction was completed. The mixture was poured in HCl IM (30 mL) and extracted with CH2CI2 (3 x 40 mL) ; the combined organic layers were washed with brine (30 mL) , dried with MgSO4. filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (PE/EtOAc/HCOOH 90/10/0.1 to 70/30/0.1 v/v/v) to give the title compound (3.32 g) as white solid. Yield 70 %. TLC: Rf = 0.38 PE/EtOAc/HCOOH 80/20/0.1 v/v/v1H-NMR (CD3OD) delta 2.18 (2H, qi) , 3.18 (2H, t, J = 6.9 Hz), 3.57 (2H, t, J = 7.2 Hz), 7.37 (2H, d, Arom) , 7.92 (2H, d, Arom) . 13C-NMR (CD3OD) delta 30.9, 32.5, 32.9, 127.7, 128.7, 131.0, 144.7, 169.5. MS (CI) m/z 275/277 (M+l)+.

Reference： [1]Patent: WO2009/49961,2009,A2 .Location in patent: Page/Page column 35

29
[ 1074-36-8 ]
[ 220270-86-0 ]
[ 1144618-69-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In acetonitrile; at 0℃; for 2h;	4- [ (3-Methyl-furoxan-4-yl) methyl] thio}benzoic acid <n="52"/>To a sospension of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> 90 % (1.0 g, 5.34 mmol) in CH3CN (10 mL) , stirred at 0 C, 4-bromomethyl-3- methyl furoxan (1.13 g, 5.84 mmol; J. Med. Chem. 1998, 41, 5393-5401) and Et3N (1.63 mL, 11.67 mmol) were added. After 2 hours the reaction was completed. The mixture was poured in HCl IM (20 mL) and extracted with EtOAc (3 x 20 mL) ; the combined organic layers were dried with MgSO4, filtered and concentrated under reduced pressure. The crude product was treated with iPr2O/MeOH to give the title compound (1.41 g) as white solid.Yield 90 %.TLC: Rf = 0.31 PE/EtOAc/HCOOH 60/40/0.1 v/v/v1H-NMR (DMSO-d6) delta 2.23 (3H, s) , 4.25 (2H, s) , 7.43 (2H, d, Arom) , 7.95 (2H, d, Arom) . 13C-NMR (CDCl3) delta 7.8, 27.3, 112.4, 128.5, 129.4, 130.0, 139.1, 154.7, 167.4. MS (CI) m/z 267 (M+l)+.

Reference： [1]Patent: WO2009/49961,2009,A2 .Location in patent: Page/Page column 50-51

30
[ 1074-36-8 ]
[ 220270-87-1 ]
[ 1144618-71-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In acetonitrile; at 0℃; for 1h;	Example 20[ (4-{ [ (3-Aminocarbonyl-furoxan-4-yl)methyl] thio}benzoyl) oxy]methyl 2- (acetyloxy) benzoate: compound (21)4- ({ [3- (Aminocarbonyl) -furoxan-4-yl] methyl} thio) benzoic acid <n="54"/>To a sospension of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> 90 % (1.16 g, 6.75 mmol) in CH3CN (10 mL) , stirred at 0 C, 4- bromomethyl-3-aminocarbonyl furoxan (1.5 g, 6.75 mmol; J. Med. Chem. 1998, 41, 5393-5401) and Et3N (1.9 mL, 13.5 mmol) were added. After 1 hours the reaction was completed. The mixture was poured in HCl IM (20 mL) and extracted with CH2CI2 (3 x 20 mL) ; the combined organic layers were dried with MgSO4, filtered and concentrated under reduced pressure. The crude product was treated with iPr2O/CH2Cl2 to give the title compound (1.69 g) as white solid. Yield 85 %. TLC: Rf = 0.16 PE/EtOAc/HCOOH 80/20/0.1 v/v/v1H-NMR (CD3OD) delta 4.53 (2H, s) , 7.50 (2H, d, Arom) , 7.97 (2H, d, Arom) . 13C-NMR (CD3OD + DMSO-d6) delta 27.9, 126.8,128.6, 129.3, 130.7, 131.1, 141.8, 156.9, 167.9. MS (CI) m/z 296 (M+l)+.

Reference： [1]Patent: WO2009/49961,2009,A2 .Location in patent: Page/Page column 52-53

31
[ 2179-57-9 ]
[ 1074-36-8 ]
[ 1166842-03-0 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 8833 - 8838

32
[ 619-58-9 ]
[ 1074-36-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodiumsulfide nonahydrate; copper; ethane-1,2-dithiol; In dimethyl sulfoxide; at 90℃; for 12h;Inert atmosphere; Sealed tube;	248 mg (1 mmol) of 4-iodobenzoic acid and 720.54 mg (3 mmol) of sodium sulfide nonahydrate were added, copper powder 12.70 mg (0.2 mmol), ethanedithiol 8.4 uL (0.1 mmol) and 3 mL of solvent DMSO was placed in a 25 mL reaction tube equipped with a magnet, sealed with argon, heated and stirred, and reacted in an oil bath at 90 C for 12 hours. After completion of the reaction, the reaction solution was washed with NaOH solution and transferred to a 250 mL separatory funnel. The ether was extracted and the upper organic solvent was removed. The aqueous phase was adjusted to pH 1-3, extracted with dichloromethane and washed with water. Dried over magnesium sulfate. Evaporated under reduced pressure and subjected to column chromatography to afford 152 mg of product as a white solid, yield 99%
99%	With sodiumsulfide nonahydrate; copper; ethane-1,2-dithiol; In dimethyl sulfoxide; at 100℃; for 20h;Inert atmosphere; Green chemistry;	General procedure: To a test tube containing a magnetic bar was added aryl iodide(1 mmol), copper powder (6.35 mg, 0.1 mmol), Na2S·9H2O(720.54 mg, 3 mmol), and DMSO (2 mL). After flushing withargon, 1,2-ethanedithiol (8.4 muL, 0.1 mmol) was added. Themixture was stirred in the oil bath at 100 C for 20 h. Aftercooled to ambient temperature, the reaction mixture was distributedin aq HCl (5%) and EtOAc. The organic layer was separated and washed with water and brine, dried, and concentratedunder vacuum. The crude product was further purifiedby column chromatography using ethyl acetate/n-hexane aseluent to provide the desired aryl thiol.

Reference： [1]Patent: CN106916090,2017,A .Location in patent: Paragraph 0037; 0038
[2]Synlett,2017,vol. 28,p. 2272 - 2276
[3]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2205 - 2212
[4]Chinese Journal of Chemistry,2010,vol. 28,p. 1441 - 1443
[5]Organic Letters,2009,vol. 11,p. 5250 - 5253

33
[ 1174738-27-2 ]
[ 1074-36-8 ]
[ 1174737-87-1 ]

Yield	Reaction Conditions	Operation in experiment
99%		A solution of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (0.73 g, 4.71 mmol, 2.25 eq) in dry N, N- dimethylformamide (30 ml) is treated with sodium thiosulfate (0.7 g, 4.03 mmol, 1.93 eq) over molecular sieves (4A beads, 0.53 g) for 1 hour. Sodium hydride (60% dispersion in oil, 0.24 g, 6.02 mmol, 2.87 eq) is added, then cis-3-(piperidin-1- yl)cyclobutyl 4-bromobenzenesulfonate a12 (0.78 g, 2.09 mmol, 1 eq) and the mixture is stirred 2 h at 200C and 12 h at 500C. The mixture is concentrated to dryness. The resulting solid is triturated in ethyl acetate (25 ml), acetonitrile (2 x 25 ml) and dichloromethane (25 ml). The solid is then taken up in methanol (3 x 20 ml) and filtered. The methanol phases are pooled and concentrated to dryness. The resulting solid is then purified by chromatography over silicagel (gradient: dichloromethane/methanol 100:0 to 0:100) to afford 0.56 g of 4-[trans-3-(piperidin-1- yl)cyclobutyl]sulfanyl}benzoic acid a13. Yield: 99 %. LC-MS (MH+): 292.

Reference： [1]Patent: WO2009/147149,2009,A1 .Location in patent: Page/Page column 38

34
[ 299962-60-0 ]
[ 1074-36-8 ]
[ 1035354-34-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 4-mercaptobenzoic acid With sodium hydroxide In tetrahydrofuran; water at 0℃; Stage #2: 4-chloro-1,2,7,8,9,10,11,13-octahydro-13-oxo-[1]benzothieno[2',3':4,5]pyrimido[1,2-a]azepine-3-carboxaldehyde In tetrahydrofuran; water at 0 - 20℃;

Reference： [1]Location in patent: experimental part Lilienkampf, Annamaria; Karkola, Sampo; Alho-Richmond, Sari; Koskimies, Pasi; Johansson, Nina; Huhtinen, Kaisa; Vihko, Kimmo; Wähälä, Kristiina [Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6660 - 6671]

35
[ 67194-84-7 ]
[ 1074-36-8 ]
[ 1217309-62-0 ]
[ 1155-51-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With iodine In ethanol; water for 3h; Reflux;

Reference： [1]Location in patent: experimental part Gangjee, Aleem; Jain, Hiteshkumar D.; Phan, Jaclyn; Guo, Xin; Queener, Sherry F.; Kisliuk, Roy L. [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 2, p. 953 - 961]

36
[ 1074-36-8 ]
[ 86499-96-9 ]
[ 1239584-07-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3897 - 3902

37
[ 1074-36-8 ]
[ 76-83-5 ]
[ 854895-10-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	In N,N-dimethyl-formamide; at 20℃; for 36h;	4-Mercaptobenzoic acid (1.54 g, 10 mmol) and trityl chloride (2.79 g, 10 mmol) were dissolved in DMF (25 mL) and stirred at an ambient temperature for 36 h. The solvent was removed under reduced pressure. The residue was dissolved in chloroform (50 mL), and washed with water (3*25 mL). The organic layer was dried over MgSO4, filtered, and concentrated. Compound 1 was obtained as a white solid (3.20 g, 81%). 1H NMR (500 MHz, CDCl3): 7.67 (d, 2H), 7.21-7.39 (m, 15H), 6.99 (d, 2H).

Reference： [1]Chemical Communications,2010,vol. 46,p. 7403 - 7405
[2]Journal of the American Chemical Society,2013,vol. 135,p. 12360 - 12365
[3]Angewandte Chemie - International Edition,2020,vol. 59,p. 3671 - 3677
Angew. Chem.,2020,vol. 132,p. 3700 - 3706,7
[4]Patent: US2016/97759,2016,A1 .Location in patent: Paragraph 0158

38
[ 1074-36-8 ]
[ 51762-67-5 ]
[ 1017280-81-7 ]

Yield	Reaction Conditions	Operation in experiment
88%		25 g (0.144 mole) of 3-nitrophthalonitrile and 22.4 g (0.145 mole) of 4-mercaptobezoic acid were dissolved in 125 ml of N-methylpyrrolidone, followed by stirring at room temperature (20 to 28C). To this solution was added portionwise 30.7 g of sodium carobonate. After completion of the addition, the reaction liquid was heated at 40C to 45C, followed by stirring for 2 hours to complete the reaction. This reaction liquid was poured into 1000 ml of water under stirring, and then a 35% by mass aqueous hydrochloric acid was added thereto adjust the pH to 3. The deposited crystal was filtered, washed with water, and dried. This crystal was dispersed in 300 ml of methanol, followed by stirring. This crystal was filtered and dried to obtain 35.5 g (yield: 88.0% by mass) of an intermediate J.

Reference： [1]Patent: EP2275495,2011,A1 .Location in patent: Page/Page column 25

39
[ 698-72-6 ]
[ 1074-36-8 ]
[ 1258424-47-3 ]

Yield	Reaction Conditions	Operation in experiment
72%		To the <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (318 mg of 90% acid, 1.85 mMol) in 1 OmL of THF at 0 C was added DIPEA (645 muL, 478 mg, 3.7 mMol) followed by dichloroethyltriazine (compound 3) (300mg, 1.69 mMol) in 5mL of THF. Reaction mixture was stirred at 0 C for 30 minutes followed by 2 hours at room temperature. Disappearance of starting material was confirmed by TLC (CH2Cl2/Me0H 95/5). 5 mL of IN HCl was added, organic layer was separated and aqueous fraction was extracted with EtOAc (3x50mL). Organic fractions were combined, washed with brine, dried over Na2SO4, filtered and solvent was removed under reduced pressure. Flash column chromatography (silica, CH2Cl2ZMeOH 95/5) yielded 360 mg (72%) of 99 as off-white solid. IH NMR (400 MHz, CDCl3) delta 8.18 (d, J = 8.4Hz, 2H), 7.72 (d, J = 8.8 Hz, 2H), 2.78 (q, J = 7.2Hz, 2H), 1.24 (t, J = 7.2 Hz, 3H). MS (ESI) m/z 296 [M+H]+.

Reference： [1]Patent: WO2010/144359,2010,A1 .Location in patent: Page/Page column 122-123

40
[ 1074-36-8 ]
[ 162411-28-1 ]
[ 1345697-56-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	In N,N-dimethyl-formamide; at 20℃; for 12h;Inert atmosphere;	EXAMPLE 6. Preparation of a compound having a structure shown in formula IX A 20 ml solution comprising 10 mmol 4-carboxyl thiophenol and 1 mmol of the intermediate having a structure shown in formula XVIII prepared in EXAMPLE 1 of the present invention in anhydrous DMF was stirred at room temperature and in nitrogen atmosphere for 12 hours. The solvent was removed by rotary evaporation. The precipitate was washed with diethyl ether, and further purified by silica gel column chromatography with a mixed solution of dichloromethane and methanol (9:1 in volume ratio) as an eluent, resulting in a compound having the structure shown in formula IX, with a yield of 83%. The compound provided according to the present invention was detected, with a result as follows: UV-vis max (in MeOH): 837 nm, 1HNMR (400 MHz, CD3OD): delta 8.87 (d, 2H, J = 14 Hz), 8.15 (d, 2H, J = 14 Hz), 7.91-7.99 (m, 6H), 7.57-7.63 (m, 4H), 7.44 (t, 2H, J = 7.2 Hz), 7.36 (d, 2H, J = 8.4 Hz), 6.40 (d, 2H, J = 14 Hz), 4.27 (t, 4H, J = 7.6 Hz), 2.85-2.92 (m, 8H), 1.93-2.10 (m, 10H), 1.77 (s, 12H). EIMS (m/z): 989 (M+ +2Na).

Reference： [1]Patent: EP2940021,2015,A1 .Location in patent: Paragraph 0056; 0057
[2]Bioconjugate Chemistry,2011,vol. 22,p. 2283 - 2295
[3]Chemistry - A European Journal,2013,vol. 19,p. 6670 - 6684
[4]Photochemistry and Photobiology,2015,vol. 91,p. 1219 - 1230

41
[ 5061-21-2 ]
[ 1074-36-8 ]
[ 1098379-73-7 ]

Yield	Reaction Conditions	Operation in experiment
58%	With triethylamine; In acetonitrile; at 80℃;	Intermediate 4: 4-((2-oxotetrahydrofuran-3-yI)thio)benzoic acidHTo a suspension of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (2 g, 12.97 mmol) in MeCN (30 mL) were added 3- bromodihydrofuran-2(3H)-one (1.318 mL, 14.27 mmol) and Et3N (1.450 mL, 10.4 mmol). The reaction mixture was stirred at 80 C overnight. The precipitate was filtered off and the filtrate concentrated under vacuum. The residue was suspended in DCM, collected by filtration and washed with DCM and water to give the intermediate 4 (1 .79 g, 58%) as white powder.
	With triethylamine; In dichloromethane; for 0.5h;Inert atmosphere; Cooling with ice;	Step a: Preparation of 4-[(2-oxotetrahydrofuran-3-yl)sulfanyl]benzoic acidTo an ice cooled solution of 4-mercaptobenzoicacid (0.5 g, 0.003 moles) in dichloromethane (5 mL) under argon atmosphere were added triethylamine (0.909 g, 0.009 moles) and a solution of bromo lactone (0.53 g, 0.003 moles) in dichloromethane (5 mL) drop wise. The reaction mixture was allowed to stir for about 30 minutes. After completion, reaction mixture was diluted by adding water and extracting indichloromethane. The combined organic layer was dried over anhydrous sodium sulphate and concentrated to get crude product which was purified by silica gel column using 70% ethyl acetate in hexane as eluent to get desired compound.Yield: 0.800 gLCMS: 239.16 (M+l)

Reference： [1]Patent: WO2014/118133,2014,A1 .Location in patent: Page/Page column 25
[2]Patent: WO2012/38943,2012,A1 .Location in patent: Page/Page column 24-25

42
[ 768-59-2 ]
[ 1074-36-8 ]
[ 1272244-15-1 ]

Yield	Reaction Conditions	Operation in experiment
77%	With water; palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate at 120℃; for 24h; chemoselective reaction;
75%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ In water at 100 - 120℃; for 16h; Sealed tube;

Reference： [1]Hikawa, Hidemasa; Yokoyama, Yuusaku [Organic and Biomolecular Chemistry, 2012, vol. 10, # 15, p. 2942 - 2945]
[2]Hikawa, Hidemasa; Azumaya, Isao [Organic and Biomolecular Chemistry, 2014, vol. 12, # 31, p. 5964 - 5972]

43
[ 1074-36-8 ]
[ 100-51-6 ]
[ 22855-95-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With water; palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate at 120℃; for 24h; chemoselective reaction;
80%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ In water at 120℃; for 16h; Sealed tube;

Reference： [1]Hikawa, Hidemasa; Yokoyama, Yuusaku [Organic and Biomolecular Chemistry, 2012, vol. 10, # 15, p. 2942 - 2945]
[2]Hikawa, Hidemasa; Azumaya, Isao [Organic and Biomolecular Chemistry, 2014, vol. 12, # 31, p. 5964 - 5972]

44
[ 1006-94-6 ]
[ 1074-36-8 ]
5-methoxyl-3-[(4-carboxyphenyl)thio]-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With tert.-butylhydroperoxide; iodine; In acetonitrile; at 80℃;	General procedure: A mixture of indole 1 (0.5mmol), thiol 2 (0.505mmol) and TBHP (0.51mmol) were dissolved in MeCN (2.0mL) at 60C in a flask, then iodine (0.10mmol, 10mol%) was added. The reaction proceeded under an air atmosphere for 0.5-1.0 h until complete consumption of starting material as monitored by TLC. The reaction mixture was quenched by the addition of saturated aq Na2S2O3 (5mL) and then extracted with EtOAc (2×10mL). The combined organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum and the crude product was purified by column chromatography using petroleum ether/ethyl acetate as eluent to provide the product 3.

Reference： [1]RSC Advances,2013,vol. 3,p. 22280 - 22284
[2]Tetrahedron,2015,vol. 71,p. 8885 - 8891

45
[ 1074-36-8 ]
[ 14533-86-9 ]
C₁₈H₁₅NO₄S [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 5017 - 5021

46
C₁₈H₁₅NO₄S [ No CAS ]
[ 1074-36-8 ]
[ 14533-86-9 ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 5017 - 5021

47
[ 71637-34-8 ]
[ 1074-36-8 ]
[ 1154617-95-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ In water at 100 - 120℃; for 16h; Sealed tube;

Reference： [1]Hikawa, Hidemasa; Azumaya, Isao [Organic and Biomolecular Chemistry, 2014, vol. 12, # 31, p. 5964 - 5972]

48
[ 2314-97-8 ]
[ 1074-36-8 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(2,2'-bipyridyl)ruthenium dichloride; triethylamine In acetonitrile at 20℃; for 1h; Irradiation;

Reference： [1]Straathof, Natan J. W.; Tegelbeckers, Bart J. P.; Hessel, Volker; Wang, Xiao; Nol, Timothy [Chemical Science, 2014, vol. 5, # 12, p. 4768 - 4773]

49
[ 934-00-9 ]
[ 1074-36-8 ]
4-(3,4-dihydroxy-5-methoxyphenylsulfanyl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium acetate In water; acetonitrile Electrolysis;	4.2. Electro-organic synthesis of sulfanyl derivatives (1a-=4a) General procedure: In typical procedure 80 mL of 0.15 M CH3COONa solution containing 5% acetonitrile was pre-electrolyzed at chosen potential (see Table 1) using undivided cell. Subsequently added 1 mm catechol 1a and 1 mm 4-Mercapto-benzoic acid 3 were added to the cell. The electrolysis was terminated when the decay of the current became more than 95%. During electrolyses process,washed the GC with acetone, because during electrolyses non conducting layers is formed on the surface of working electrode. At the end of electrolyses process the cell was placed in refrigerator overnight. The solid precipitated (ppt) was collected by filtration and washed with distilled water several time and recrystallized from solvent (methanol:acetone 30:70).The products were characterized using modern techniques IR, H NMR, CNMR, and MS.

Reference： [1]Khan, Zia Ul Haq; Khan, Arif Ullah; Chen, Yongmei; Khan, Shafiullah; Kong, Dandan; Tahir, Kamran; Khan, Faheem Ullah; Wan, Pingyu; Jin, Xin [Tetrahedron, 2015, vol. 71, # 11, p. 1674 - 1678]

50
[ 1074-36-8 ]
[ 1151989-04-6 ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 5721 - 5724
[2]Journal of the American Chemical Society,2017,vol. 139,p. 4009 - 4018

51
[ 1074-36-8 ]
[ 25440-14-6 ]
5,10,15,20-tetrakis(4-carboxyphenylthio-2,3,5,6-tetrafluorophenyl)porphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		The protons signal relative to N-H was not observed, due to their replacement by deuterium from deuterated methanol in porphyrins P2-P6. Finally, the fifth fraction was identified as porphyrin P6 (3.1% yield), m.p. > 300 C, 1H NMR: deltaH ppm (Acetone-d6) 9.46 (broad, 8H, H-beta), 8.14 (d, J = 8.4 Hz, 8H, S-C6H4-CO2H), 7.82 (d, J = 8.3 Hz, 8H, S-C6H4-CO2H), and -2.87 (s, 2H, NH). 19F NMR: deltaF ppm (Acetone-d6) -162.02 (dd, J = 11.9 and 24.7 Hz, 8F, F-meta), and -157.70 (dd, J = 11.9 and 24.7 Hz, 8F, F-ortho). UV-vis (Acetone) lambdamax, nm (log ?): 412 (5.14), 504 (4.07), 582 (3.57). HRMS (FAB+) m/z: calcd for C72H31F16N4O8S4 (M+H)+: 1511.0764; found: 1511.0752.

Reference： [1]Applied Catalysis A: General,2015,vol. 503,p. 9 - 19
[2]Journal of Porphyrins and Phthalocyanines,2014,vol. 18,p. 967 - 974

52
[ 933779-29-4 ]
[ 1074-36-8 ]
[Au(Hmba)(MPPF)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		[Au(Hmba)(MPPF)] (compound 5). <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (0.109 g, 0.70 mmol) and KOH (0.040 g, 0.70 mmol) were dissolved in 20 mL of a 4:1 EtOH/H2O mixture giving rise to a pale yellow solution that was stirred at RT for 10 minutes becoming colorless. The addition of [AuCl(MPPF)] (0.426 g, 0.70 mmol) led to thick yellow suspension that was stirred for 1 hour at RT. After solvents removal, the crude was washed with water (3×5 mL) and a 9:1 n-Hexane/Et2O mixture (3×10 mL). Compound 6 was then isolated as a fine yellow solid in 89% yield (0.455 g). Crystals of compound 6 were obtained from a solution of compound 6 in CH2Cl2 layered with n-hexane at RT as orange prisms.

Reference： [1]Chemical Science,2015,vol. 6,p. 5269 - 5283
[2]Patent: US2015/353591,2015,A1 .Location in patent: Paragraph 0051

53
[ 207399-07-3 ]
[ 1074-36-8 ]
C₄₃H₄₉N₂O₂S⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Macromolecular Bioscience,2016,p. 1432 - 1441
[2]Journal of Materials Chemistry B,2015,vol. 3,p. 8321 - 8327

54
[ 1074-36-8 ]
[ 80-40-0 ]
[ 13205-49-7 ]

Yield	Reaction Conditions	Operation in experiment
43%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20℃; for 20h;Inert atmosphere;	To a solution of ethyl 4-methylbenzenesulfonate (300 mg, 1.5 mmol, 1.0 eq.) in toluene (9 ml) were added 4-mercaptobenzoic acid (278 mg, 1.8 mmol, 1.2 eq.) and DBU (300 mul, 2.0 mmol, 1.3 eq.) and the mixture was stirred for 20 h at rt. The reaction was quenched with aq. sat NH4Cl (3 ml) and was diluted with H2O and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (3 x 20 ml) and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Separation via column chromatography on silica gel (CyH/EtOAc 1:1) afforded the desired product as white solid (118 mg, 43%).

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 182,p. 121 - 126

55
[ 1074-36-8 ]
[ 123-31-9 ]
[ 1155-51-7 ]
C₁₃H₈O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Myceliophthora thermophila laccase In aq. phosphate buffer at 20℃; for 0.333333h; Green chemistry; Enzymatic reaction;	2.3 Experimental procedures General procedure: For analytical experiments one thiol (1-5 mM) and one p-hydroquinone (1 mM) were incubated with laccase (activity 1 U) in a final volume of 4 ml of the respective buffer (sodium acetate buffer, pH 5 for Pycnoporus cinnabarinus and citrate phosphate buffer, pH 7 for Myceliophthora thermophila, both stored at 4°C and used at room temperature for reactions). Reaction mixtures were incubated with agitation at 200 rpm at room temperature in brown-glass-bottles. After incubation for 20 min, 2 h, or 24 h the mixture was analyzed by HPLC, LC-10AT VP system (Shimadzu, Germany) consisting of a FCV-10AL VP pump, SPD-M10A VP diode array detector, and a SCL-10A VP control unit controlled by Class-VP version 6.12 SP5. The separation of substances was achieved on a RP18 column at a flow rate of 1 mL min-1. The solvent system consisted of methanol (eluent A) and 0.1% phosphoric acid (eluent B), starting from an initial ration of 10% A and 90% B and reaching 100% methanol within 14min.

Reference： [1]Schlippert, Max; Mikolasch, Annett; Hahn, Veronika; Schauer, Frieder [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 126, p. 106 - 114]

56
[ 95-71-6 ]
[ 1074-36-8 ]
[ 1155-51-7 ]
4-(4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)sulfanylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.6%	With Myceliophthora thermophila laccase In aq. phosphate buffer at 20℃; for 0.333333h; Green chemistry; Enzymatic reaction;	2.3 Experimental procedures General procedure: For analytical experiments one thiol (1-5 mM) and one p-hydroquinone (1 mM) were incubated with laccase (activity 1 U) in a final volume of 4 ml of the respective buffer (sodium acetate buffer, pH 5 for Pycnoporus cinnabarinus and citrate phosphate buffer, pH 7 for Myceliophthora thermophila, both stored at 4°C and used at room temperature for reactions). Reaction mixtures were incubated with agitation at 200 rpm at room temperature in brown-glass-bottles. After incubation for 20 min, 2 h, or 24 h the mixture was analyzed by HPLC, LC-10AT VP system (Shimadzu, Germany) consisting of a FCV-10AL VP pump, SPD-M10A VP diode array detector, and a SCL-10A VP control unit controlled by Class-VP version 6.12 SP5. The separation of substances was achieved on a RP18 column at a flow rate of 1 mL min-1. The solvent system consisted of methanol (eluent A) and 0.1% phosphoric acid (eluent B), starting from an initial ration of 10% A and 90% B and reaching 100% methanol within 14min.

Reference： [1]Schlippert, Max; Mikolasch, Annett; Hahn, Veronika; Schauer, Frieder [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 126, p. 106 - 114]

57
[ 95-71-6 ]
[ 1074-36-8 ]
[ 1155-51-7 ]
C₂₈H₁₈O₈S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Myceliophthora thermophila laccase In aq. phosphate buffer at 20℃; for 0.333333h; Green chemistry; Enzymatic reaction;	2.3 Experimental procedures General procedure: For analytical experiments one thiol (1-5 mM) and one p-hydroquinone (1 mM) were incubated with laccase (activity 1 U) in a final volume of 4 ml of the respective buffer (sodium acetate buffer, pH 5 for Pycnoporus cinnabarinus and citrate phosphate buffer, pH 7 for Myceliophthora thermophila, both stored at 4°C and used at room temperature for reactions). Reaction mixtures were incubated with agitation at 200 rpm at room temperature in brown-glass-bottles. After incubation for 20 min, 2 h, or 24 h the mixture was analyzed by HPLC, LC-10AT VP system (Shimadzu, Germany) consisting of a FCV-10AL VP pump, SPD-M10A VP diode array detector, and a SCL-10A VP control unit controlled by Class-VP version 6.12 SP5. The separation of substances was achieved on a RP18 column at a flow rate of 1 mL min-1. The solvent system consisted of methanol (eluent A) and 0.1% phosphoric acid (eluent B), starting from an initial ration of 10% A and 90% B and reaching 100% methanol within 14min.

Reference： [1]Schlippert, Max; Mikolasch, Annett; Hahn, Veronika; Schauer, Frieder [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 126, p. 106 - 114]

58
[ 1074-36-8 ]
[ 608-43-5 ]
[ 1155-51-7 ]
4-(4,5-dimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)sulfanylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With Myceliophthora thermophila laccase In aq. phosphate buffer at 20℃; for 0.333333h; Green chemistry; Enzymatic reaction;	2.3 Experimental procedures General procedure: For analytical experiments one thiol (1-5 mM) and one p-hydroquinone (1 mM) were incubated with laccase (activity 1 U) in a final volume of 4 ml of the respective buffer (sodium acetate buffer, pH 5 for Pycnoporus cinnabarinus and citrate phosphate buffer, pH 7 for Myceliophthora thermophila, both stored at 4°C and used at room temperature for reactions). Reaction mixtures were incubated with agitation at 200 rpm at room temperature in brown-glass-bottles. After incubation for 20 min, 2 h, or 24 h the mixture was analyzed by HPLC, LC-10AT VP system (Shimadzu, Germany) consisting of a FCV-10AL VP pump, SPD-M10A VP diode array detector, and a SCL-10A VP control unit controlled by Class-VP version 6.12 SP5. The separation of substances was achieved on a RP18 column at a flow rate of 1 mL min-1. The solvent system consisted of methanol (eluent A) and 0.1% phosphoric acid (eluent B), starting from an initial ration of 10% A and 90% B and reaching 100% methanol within 14min.

Reference： [1]Schlippert, Max; Mikolasch, Annett; Hahn, Veronika; Schauer, Frieder [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 126, p. 106 - 114]

59
[ 1074-36-8 ]
[ 608-43-5 ]
[ 1155-51-7 ]
C₂₂H₁₆O₆S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Myceliophthora thermophila laccase In aq. phosphate buffer at 20℃; for 0.333333h; Green chemistry; Enzymatic reaction;	2.3 Experimental procedures General procedure: For analytical experiments one thiol (1-5 mM) and one p-hydroquinone (1 mM) were incubated with laccase (activity 1 U) in a final volume of 4 ml of the respective buffer (sodium acetate buffer, pH 5 for Pycnoporus cinnabarinus and citrate phosphate buffer, pH 7 for Myceliophthora thermophila, both stored at 4°C and used at room temperature for reactions). Reaction mixtures were incubated with agitation at 200 rpm at room temperature in brown-glass-bottles. After incubation for 20 min, 2 h, or 24 h the mixture was analyzed by HPLC, LC-10AT VP system (Shimadzu, Germany) consisting of a FCV-10AL VP pump, SPD-M10A VP diode array detector, and a SCL-10A VP control unit controlled by Class-VP version 6.12 SP5. The separation of substances was achieved on a RP18 column at a flow rate of 1 mL min-1. The solvent system consisted of methanol (eluent A) and 0.1% phosphoric acid (eluent B), starting from an initial ration of 10% A and 90% B and reaching 100% methanol within 14min.

Reference： [1]Schlippert, Max; Mikolasch, Annett; Hahn, Veronika; Schauer, Frieder [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 126, p. 106 - 114]

60
[ 824-46-4 ]
[ 1074-36-8 ]
[ 1155-51-7 ]
4-(4-methoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)sulfanyl benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.3%	With Myceliophthora thermophila laccase; In aq. phosphate buffer; at 20℃; for 0.333333h;pH 7;Green chemistry; Enzymatic reaction;	General procedure: For analytical experiments one thiol (1-5 mM) and one p-hydroquinone (1 mM) were incubated with laccase (activity 1 U) in a final volume of 4 ml of the respective buffer (sodium acetate buffer, pH 5 for Pycnoporus cinnabarinus and citrate phosphate buffer, pH 7 for Myceliophthora thermophila, both stored at 4C and used at room temperature for reactions). Reaction mixtures were incubated with agitation at 200 rpm at room temperature in brown-glass-bottles. After incubation for 20 min, 2 h, or 24 h the mixture was analyzed by HPLC, LC-10AT VP system (Shimadzu, Germany) consisting of a FCV-10AL VP pump, SPD-M10A VP diode array detector, and a SCL-10A VP control unit controlled by Class-VP version 6.12 SP5. The separation of substances was achieved on a RP18 column at a flow rate of 1 mL min-1. The solvent system consisted of methanol (eluent A) and 0.1% phosphoric acid (eluent B), starting from an initial ration of 10% A and 90% B and reaching 100% methanol within 14min.

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2016,vol. 126,p. 106 - 114

61
[ 824-46-4 ]
[ 1074-36-8 ]
[ 1155-51-7 ]
C₂₁H₁₄O₇S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Myceliophthora thermophila laccase In aq. phosphate buffer at 20℃; for 0.333333h; Green chemistry; Enzymatic reaction;	2.3 Experimental procedures General procedure: For analytical experiments one thiol (1-5 mM) and one p-hydroquinone (1 mM) were incubated with laccase (activity 1 U) in a final volume of 4 ml of the respective buffer (sodium acetate buffer, pH 5 for Pycnoporus cinnabarinus and citrate phosphate buffer, pH 7 for Myceliophthora thermophila, both stored at 4°C and used at room temperature for reactions). Reaction mixtures were incubated with agitation at 200 rpm at room temperature in brown-glass-bottles. After incubation for 20 min, 2 h, or 24 h the mixture was analyzed by HPLC, LC-10AT VP system (Shimadzu, Germany) consisting of a FCV-10AL VP pump, SPD-M10A VP diode array detector, and a SCL-10A VP control unit controlled by Class-VP version 6.12 SP5. The separation of substances was achieved on a RP18 column at a flow rate of 1 mL min-1. The solvent system consisted of methanol (eluent A) and 0.1% phosphoric acid (eluent B), starting from an initial ration of 10% A and 90% B and reaching 100% methanol within 14min.

Reference： [1]Schlippert, Max; Mikolasch, Annett; Hahn, Veronika; Schauer, Frieder [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 126, p. 106 - 114]

62
[ 15233-65-5 ]
[ 1074-36-8 ]
[ 1155-51-7 ]
C₁₅H₁₂O₆S [ No CAS ]
C₂₂H₁₆O₈S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Myceliophthora thermophila laccase In aq. phosphate buffer at 20℃; for 0.333333h; Green chemistry; Enzymatic reaction;	2.3 Experimental procedures General procedure: For analytical experiments one thiol (1-5 mM) and one p-hydroquinone (1 mM) were incubated with laccase (activity 1 U) in a final volume of 4 ml of the respective buffer (sodium acetate buffer, pH 5 for Pycnoporus cinnabarinus and citrate phosphate buffer, pH 7 for Myceliophthora thermophila, both stored at 4°C and used at room temperature for reactions). Reaction mixtures were incubated with agitation at 200 rpm at room temperature in brown-glass-bottles. After incubation for 20 min, 2 h, or 24 h the mixture was analyzed by HPLC, LC-10AT VP system (Shimadzu, Germany) consisting of a FCV-10AL VP pump, SPD-M10A VP diode array detector, and a SCL-10A VP control unit controlled by Class-VP version 6.12 SP5. The separation of substances was achieved on a RP18 column at a flow rate of 1 mL min-1. The solvent system consisted of methanol (eluent A) and 0.1% phosphoric acid (eluent B), starting from an initial ration of 10% A and 90% B and reaching 100% methanol within 14min.

Reference： [1]Schlippert, Max; Mikolasch, Annett; Hahn, Veronika; Schauer, Frieder [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 126, p. 106 - 114]

63
[ 15233-65-5 ]
[ 1074-36-8 ]
[ 1155-51-7 ]
C₂₂H₁₆O₈S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26.2%	With Pycnoporus cinnabarinus laccase In aq. acetate buffer at 20℃; for 2h; Green chemistry; Enzymatic reaction;	2.3 Experimental procedures General procedure: For analytical experiments one thiol (1-5 mM) and one p-hydroquinone (1 mM) were incubated with laccase (activity 1 U) in a final volume of 4 ml of the respective buffer (sodium acetate buffer, pH 5 for Pycnoporus cinnabarinus and citrate phosphate buffer, pH 7 for Myceliophthora thermophila, both stored at 4°C and used at room temperature for reactions). Reaction mixtures were incubated with agitation at 200 rpm at room temperature in brown-glass-bottles. After incubation for 20 min, 2 h, or 24 h the mixture was analyzed by HPLC, LC-10AT VP system (Shimadzu, Germany) consisting of a FCV-10AL VP pump, SPD-M10A VP diode array detector, and a SCL-10A VP control unit controlled by Class-VP version 6.12 SP5. The separation of substances was achieved on a RP18 column at a flow rate of 1 mL min-1. The solvent system consisted of methanol (eluent A) and 0.1% phosphoric acid (eluent B), starting from an initial ration of 10% A and 90% B and reaching 100% methanol within 14min.

Reference： [1]Schlippert, Max; Mikolasch, Annett; Hahn, Veronika; Schauer, Frieder [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 126, p. 106 - 114]

64
[ 97-53-0 ]
[ 1074-36-8 ]
C₁₇H₁₈O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With (2,4,6-trimethylbenzoyl)diphenylphosphine oxide; In 1,4-dioxane; ethanol; at 40℃; for 30h;UV-irradiation;	100g eugenol, 200g<strong>[1074-36-8]4-mercapto benzoic acid</strong>, 35g2, 4, 6-trimethyl benzoyl diphenyl phosphine oxide, is dissolved in dioxane, and the mixed solution of ethanol, in 40 C lower 365 nm ultraviolet lamp irradiation 30 hours, pressure reducing rotary evaporated to remove the mixed solvent, water washing and drying to obtain eugenol-mercapto benzoic acid compound, the yield is 92%.

Reference： [1]Patent: CN105503674,2016,A .Location in patent: Paragraph 0085; 0086

65
[ 1074-36-8 ]
[ 21571-66-4 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11193 - 11197
Angew. Chem.,2016,vol. 128,p. 11359 - 11363,5

66
[ 1074-36-8 ]
[ 206268-72-6 ]
4-[(4,5-dicyano-2-nitrophenyl)sulfanyl]benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; In water; N,N-dimethyl-formamide; at 25℃; for 1h;	General procedure: A solution of 1.38 g (0.01 mol) of anhydrous potassium carbonate in 7 mL of water was added to a solution of 2.52 g (0.01 mol) of 4-bromo-5-nitrophthalonitrile (1) and 0.01 mol of the corresponding benzoic acid in 50 mL of DMF in a two-neck flask equipped with a reflux condenser. The reaction mixture was stirred at 25 for 1 h. A precipitate formed and was filtered off, washed with 5% aqueous HCl until colorless filtrates, and dried in air at 70-80. To isolate compounds 2 and 3, the reaction mixture was acidified with 5% aqueous HCl, and the precipitate that formed was filtered off and washed with acidified water. During synthesis of dinitirile 4, abundant precipitate formed and was filtered off. Dilution of the filtrate with water gave more precipitate which was filtered off and combined with the first portion. The combined precipitate was washed with acidified water. The yields of 24 were 63-78%.

Reference： [1]Russian Journal of General Chemistry,2017,vol. 87,p. 3063 - 3070
Ross. Khim. Zh.,2015,vol. 59,p. 8 - 16,9
[2]Journal of Porphyrins and Phthalocyanines,2017,vol. 21,p. 37 - 47

67
[ 1074-36-8 ]
[ 206268-72-6 ]
4,4′-((4,5-dicyano-1,2-phenylene)bis(sulfanediyl))dibenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; In water; N,N-dimethyl-formamide; at 80 - 90℃; for 24h;	General procedure: A solution of 5.52 g (0.04 mol) of anhydrous potassium carbonate in 7 mL of water was added to a solution of 2.52 g (0.01 mol) of 4-bromo-5-nitrophthalonitrile (1) and 0.02 mol of corresponding benzoic acid in 50 mL of DMF in a two-necked flask equipped with a reflux condenser. The resulting mixture was diluted with water, heated with stirring at 80-90C for 24 h, and poured into acidified water. The solid target product was filtered off and washed with 5% aqueous HCl until colorless washings.

Reference： [1]Journal of Porphyrins and Phthalocyanines,2017,vol. 21,p. 37 - 47
[2]Russian Journal of General Chemistry,2018,vol. 88,p. 2020 - 2027
Ross. Khim. Zh.,2016,vol. 60,p. 80 - 88,9

68
[ 2179-57-9 ]
[ 1074-36-8 ]
[ 16195-39-4 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 776 - 780

69
[ 70258-18-3 ]
[ 1074-36-8 ]
C₁₃H₁₀ClNO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium hydroxide; In ethanol; at 20℃; for 10h;Reflux;	General procedure: To a solution of 2 (or 4)-mercaptobenzoic acid (3.1 g, 20 mmol), compound 1 (3.3 g, 22 mmol) andanhydrous ethanol (100 mL) was added potassium hydroxide (2.2 g, 40 mmol) at room temperature.The resulting mixture was heated to reflux for 10 h. Then it was cooled to room temperature, allowed tosettle for 2 h, and the precipitates were collected by filtration. To the solid was added 100 mL of water,followed by adding 5% hydrochloric acid to adjust the pH to 2-3. The precipitates were filtered off to obtain compound 2.

Reference： [1]Molecules,2017,vol. 22

70
[ 1897-41-2 ]
[ 1074-36-8 ]
4,4',4'',4'''-((3,6-dicyanobenzene-1,2,4,5-tetrayl)tetrakis(sulfanediyl))-tetrabenzoic acid [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 13660 - 13668
[2]Chemical Communications,2019,vol. 55,p. 4841 - 4844

71
[ 2160-62-5 ]
[ 1074-36-8 ]
[ 74-88-4 ]
C₁₃H₉NO₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		[00811] A mixture of <strong>[2160-62-5]5-bromothiophene-2-carbonitrile</strong> (406 mg, 2.83 mmol), 4-mercaptobenzoic acid (479 mg, 3.1 1 mmol), and K2CO3 (781 mg, 5.65 mmol) in DMF (1 1 mL) was stirred at 120C for 2.5 h. After cooling to rt, Mel (750 L, 1 1 .32 mmol) was added and the mixture was stirred at 50 C for 2 h. EtOAc was added and the organic phase was washed with H20/brine 1 :1 (3 x), dried over Na2S04 and filtered. The solvent was removed under reduced pressure and the crude treated with BF3.THF complex (1 .0 M in THF; 7.0 mL, 7.0 mmol). The mixture was stirred for at rt for 1 h, and then quenched slowly with EtOH. The mixture was heated at reflux for 1 h before the solvent was removed under reduced pressure. DCM (40 mL) was added, followed by Et3N (480 mu, 3.45 mmol) and B0C2O (753 mg, 3.45 mmol). The mixture was stirred at rt for 12 h and then diluted with DCM. The organic phase was washed with H2O, dried over Na2S04, filtered and the solvent was removed under reduced pressure. The crude was purified by chromatography (EtOAc/cyclohexane 2?20%) to afford methyl 4-((5-(((te/ -butoxycarbonyl)amino)methyl)thiophen-2-yl)thio)benzoate (288 mg, 27%). H NMR (500 MHz, CDC ) delta 7.90 (d, J = 8.2 Hz, 2H), 7.09 - 7.22 (m, 3H), 6.96 (br. s, 1 H), 4.83 - 5.09 (m, 1 H), 4.48 (br. s, 1 H), 3.89 (s, 3H), 1 .47 (s, 9H).

Reference： [1]Patent: WO2017/141049,2017,A1 .Location in patent: Paragraph 00811

72
[ 947-95-5 ]
[ 1074-36-8 ]
4-(4-formyl-3-methyl-1-phenyl-1H-pyrazol-5-ylthio)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With copper(l) iodide; triphenylphosphine; potassium hydroxide In N,N-dimethyl-formamide at 70℃; for 2h; Inert atmosphere;	3 4.2.1.1. Method (A). General procedure: A mixture of 4-hydroxybenzoic acid (1.38g, 10mmol) or 4-mercaptobenzoic acid (1.54g, 10mmol), potassium hydroxide (2.24g, 40mmol), triphenylphosphine (0.524g, 2mmol) and cupper (I) iodide (0.19g, 1mmol) in DMF (20mL) was treated with 5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3) (2.02mg, 10mmol). The mixture was heated to 70°C and stirred under Argon for 2h. The reaction was quenched with water and extracted with ethyl acetate. The organics were dried (Na2SO4), concentrated, and purified by column chromatography (0-25% EtOAc/n-hexane).

Reference： [1]Galal, Shadia A.; Khairat, Sarah H.M.; Ali, Hamed I.; Shouman, Samia A.; Attia, Yasmin M.; Ali, Mamdouh M.; Mahmoud, Abeer E.; Abdel-Halim, Abeer H.; Fyiad, Amal A.; Tabll, Ashraf; El-Shenawy, Reem; El Abd, Yasmine S.; Ramdan, Raghda; El Diwani, Hoda I. [European Journal of Medicinal Chemistry, 2018, vol. 144, p. 859 - 873]

73
[ 1074-36-8 ]
[ 25440-14-6 ]
5-[4-carboxyphenylthio-2,3,5,6-tetrafluorophenyl]-10,15,20-tris(pentafluorophenyl)porphyrin [ No CAS ]
C₅₈H₂₀F₁₈N₄O₄S₂ [ No CAS ]
C₅₈H₂₀F₁₈N₄O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33.6%	Stage #1: 4-mercaptobenzoic acid With pyridine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: tetrakis(pentafluorophenyl)porphyrin In N,N-dimethyl-formamide for 1h;	Synthesis of metalloporphyrins (see The second and third fractions were identified as porphyrins P3 and P4. Porphyrin P3 (17% yield), m.p. > 300 °C. 1H NMR: δH ppm (CD3OD): 9.18 (broad, 8H, H-β), 8.08 (d, J = 8.4 Hz, 4H, S-C6H4-CO2H), and 7.67 (d, J = 8.4 Hz, 4H, S-C6H4-CO2H). 19F NMR: δF ppm (CD3OD) -188.67 to -188.49 (m, 4F, F-meta), -179.01 (t, J = 20.4 Hz, 2F, F-para), -163.73 (dd, J = 7.8 and 23.0 Hz, 4F, F-ortho), -162.89 (dd, J = 12.2 and 24.4 Hz, 4F, F-meta), and -158.68 (dd, J = 12.2 and 24.4 Hz, 4F, F-ortho). UV-vis (CHCl3) λmax, nm (log ɛ): 412 (5.24), 506 (4.06), 584 (3.90). HRMS (FAB+) m/z: calcd for C58H21F18N4O4S2 (M+H)+: 1243.0711; found: 1243.0696. Porphyrin P4 (12% yield), m.p. > 300 °C. 1H NMR: δH ppm (CD3OD): 9.18 (broad, 8H, H-β), 8.08 (d, J = 8.2 Hz, 4H, S-C6H4-CO2H), and 7.67 (d, J = 8.2 Hz, 4H, S-C6H4-CO2H). 19F NMR: δF ppm (CD3OD) -190.20 to -190.03 (m, 4F, F-meta), -180.54 (t, J = 20.2 Hz, 2F, F-para), -165.27 (dd, J = 7.3 and 22.6 Hz, 4F, F-ortho), -164.41 (dd, J = 12.3 and 24.5 Hz, 4F, F-meta), and -158.68 (dd, J = 12.3 and 24.5 Hz, 4F, F-ortho). UV-vis (CHCl3) λmax, nm (log ɛ): 412 (5.22), 506 (4.08), 582 (3.66). HRMS (FAB+) m/z: calcd for C58H21F18N4O4S2 (M+H)+: 1243.0711; found: 1243.0675. The fourth fraction was identified as porphyrin P5 (37% yield), m.p. > 300 °C. 1H NMR: δH ppm (CD3OD): 9.24 (broad, 8H, H-β), 8.16 (d, J = 8.4 Hz, 6H, S-C6H4-CO2H), and 7.75 (d, J = 8.4 Hz, 6H, S-C6H4-CO2H). 19F NMR: δF ppm (CD3OD) -190.19 to -190.02 (m, 2F, F-meta), -180.53 (t, J = 20.4 Hz, 1F, F-para), -165.25 (dd, J = 7.6 and 22.6 Hz, 2F, F-ortho), -164.40 to 164.21 (m, 4F, F-meta), and -160.20 (dd, J = 12.3 and 24.7 Hz, 4F, F-ortho). UV-vis (CH3OH) λmax, nm (log ɛ): 410 (5.16), 504 (4.13), 582 (3.65). HRMS (FAB+) m/z: calcd for C65H26F17N4O6S3 (M+H)+: 1377.0738; found: 1377.0737.

Reference： [1]de F. Castro, Kelly A.D.; Simões, Mário M.Q.; da Graça P.M.S. Neves, Maria; Cavaleiro, José A.S.; Ribeiro, Ronny R.; Wypych, Fernando; Nakagaki, Shirley [Applied Catalysis A: General, 2015, vol. 503, p. 9 - 19]

74
[ 1074-36-8 ]
[ 25440-14-6 ]
5-[4-carboxyphenylthio-2,3,5,6-tetrafluorophenyl]-10,15,20-tris(pentafluorophenyl)porphyrin [ No CAS ]
5,10,15,20-tetrakis(4-carboxyphenylthio-2,3,5,6-tetrafluorophenyl)porphyrin [ No CAS ]
C₅₈H₂₀F₁₈N₄O₄S₂ [ No CAS ]
C₅₈H₂₀F₁₈N₄O₄S₂ [ No CAS ]
C₆₅H₂₅F₁₇N₄O₆S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 19% 2: 17% 3: 12% 4: 37% 5: 3.1%	Stage #1: 4-mercaptobenzoic acid With pyridine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: tetrakis(pentafluorophenyl)porphyrin In N,N-dimethyl-formamide for 3h;	Synthesis of metalloporphyrins (see Fig. 1 ): In a round-bottom flask, 0.4 mmol of 4-mercaptobenzoic acid was dissolved in 15 mL of DMF containing 0.5 mL of pyridine. The reaction mixture was kept under magnetic stirring at room temperature for 30 min. Porphyrin P1 (0.1 mmol) was added, and the reaction mixture was kept under magnetic stirring for 3 h and monitored by TLC. Then, the solvent was evaporated under reduced pressure, and the crude solid was purified by preparative TLC (thin-layer chromatography - silica was the stationary phase, and chloroform/methanol (9:1 v/v) was the mobile phase). In this process, several fractions were separated and numbered from 1 to 5. The first fraction was identified as porphyrin P2 (19% yield), m.p. > 300 °C. 1H NMR: δH ppm (CD3OD) 9.20 (broad, 8H, H-β), 8.07 (d, J = 9 Hz, 2H, S-C6H4-CO2H), and 7.66 (d, J = 9 Hz, 2H, S-C6H4-CO2H). 19F NMR: δF ppm (CD3OD) -188.35 to -188.17 (m, 6F, F-meta), -178.57 (t, J = 20.0 Hz, 3F, F-para), -163.67 (dd, J = 7.5 and 22.8 Hz, 6F, F-ortho), -162.80 (dd, J = 12.3 and 24.3 Hz, 2F, F-meta), and -158.51 (dd, J = 12.3 and 24.3 Hz, 2F, F-ortho). UV-vis (CHCl3) λmax, nm (log ɛ): 414 (5.20), 506 (4.08), 584 (3.90). HRMS (FAB+) m/z: calcd for C51H16F19N4O2S (M+H)+: 1109.0685; found: 1109.0667.

Reference： [1]de F. Castro, Kelly A.D.; Simões, Mário M.Q.; da Graça P.M.S. Neves, Maria; Cavaleiro, José A.S.; Ribeiro, Ronny R.; Wypych, Fernando; Nakagaki, Shirley [Applied Catalysis A: General, 2015, vol. 503, p. 9 - 19]

75
[ 53339-53-0 ]
[ 1074-36-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With diethylene glycol dimethyl ether at 70℃; for 0.5h; Sonication;	20 Example 20: Preparation of 4-mercaptobenzoic acid: In a 10 mL round bottom flask, 0.70 g of 4-mercaptobenzyl alcohol and 2 g of diethylene glycol dimethyl ether were sequentially added, and the resulting mixture was subjected to ultrasonic irradiation at 40 kHz/30 W/70 ° C for 30 minutes in an ultrasonic reaction apparatus.Diethylene glycol dimethyl ether is removed under reduced pressure,Recrystallization to 4-mercaptobenzoic acid0.72 g, yield 94%.
84%	With oxygen at 120℃; for 16h; Green chemistry;

Reference： [1]Current Patent Assignee: CENTRAL SOUTH UNIVERSITY - CN108467342, 2018, A Location in patent: Paragraph 0136; 0137
[2]Liu, Kai-Jian; Jiang, Si; Lu, Ling-Hui; Tang, Ling-Li; Tang, Shan-Shan; Tang, Hai-Shan; Tang, Zilong; He, Wei-Min; Xu, Xinhua [Green Chemistry, 2018, vol. 20, # 13, p. 3038 - 3043]

76
[ 1074-36-8 ]
[ 274924-71-9 ]
4-[2-(1H-1,2,3-benzotriazol-1-yl)-4,5-dicyanophenylsulfanyl]benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In water; N,N-dimethyl-formamide; at 25℃; for 0.5h;	General procedure: a. A solution of 0.68 g (5 mmol) of anhydrous KCO3 in 4 mL of water was added to a mixture of 0.5 mmol of compound 2 and 0.06 g (0.5 mmol) of 1H-benzotriazole 25 mL of DMF. The reaction mixture was stirred at 70 for 1 h. The precipitate that formed was filtered off, washed with 5% aqueous HCl, and dried. b. A solution of 0.07 g (0.5 mmol) of anhydrous KCO3 in 4 mL of water was added to a mixture of 0.15 g(0.5 mmol) of 4-(1H-benzotriazol-1-yl)-5-nitrophthalonitrile and 0.5 mmol of the corresponding benzoic acid in 25 mL of DMF. The reaction mixture was stirred at 25 for 0.5 H. The resulting precipitate was filtered off, washed with 5% aqueous HCl, and dried.

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 751 - 757
Zh. Org. Khim.,2018,vol. 88,p. 672 - 678,7

77
[ 5147-00-2 ]
[ 1074-36-8 ]
C₁₀H₁₁NO₄S [ No CAS ]

Reference： [1]ChemCatChem,2018,vol. 10,p. 3671 - 3674

78
[ 1074-36-8 ]
(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) chloride [ No CAS ]
(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) p-mercaptobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; In water; ethyl acetate; at 20℃; for 24h;	(1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) chloride (63 mg, 0.10 mmol) andp-mercaptobenzoic acid (31 mg, 0.20 mmol) were dissolved in ethyl acetate (5 mL), and K2CO3(27 mg, 0.20 mmol) was dissolved in water (5 mL). Both solutions were mixed and stirred vigorouslyat rt for 24 h. The two phases were separated, and the aqueous phase was re-extracted twice with ethylacetate (10 mL). The combined organic phase was washed with 8% HCl (2 x 10 mL), before dryingover MgSO4 and filtered. The filtrate was concentrated to approximately 3 mL before the addition ofpentane (40 mL). The solution was cooled down to -26 C to allow the product to precipitate out ofthe solution before filtering and drying in vacuo. An off-white product was isolated. Yield: 55 mg,70%. 1H-NMR (400 MHz, CDCl3, delta ppm): 7.63 (d, J = 8.4 Hz, 2H, Hb), 7.47 (d, J = 8.4 Hz, 2H, Ha),7.34-7.18 (m, 12H, CH), 7.09-6.96 (m, 8H, CH), 5.45 (s, 4H, CH2-benzyl). 13C-NMR (101 MHz, CDCl3, delta ppm): 182.3 (NCN), 171.7 (C=O), 153.7, 135.8, 132.0, 131.8, 130.6, 129.4, 129.3, 128.6, 128.6, 128.1, 127.3,127.2, 123.1 (CHimidazol + CHphenyl + CHbenzyl), 52.6 (CH2). MS (QMS-MS/MS) m/z: 773.15 [M + Na]+.IR (ATR): 3056 (w), 1668 (w), 1580 (w), 1487 (m), 1446 (w), 1025 (m), 764 (m), 729 (s), 694 (s), 628(w),518 (w). Melting point range: 177-179 C. Anal. calcd for C36H29N2O2SAu (750.70): C, 57.59; H, 3.90;N, 3.73; S, 4.27; Found: C, 57.33; H, 3.72; N, 3.60; S, 4.59.

Reference： [1]ChemMedChem,2019,vol. 14,p. 1086 - 1095
[2]Molecules,2018,vol. 23

79
[ 1074-36-8 ]
[ 195455-54-0 ]
[ 943616-65-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: ethanol; water / 80 °C 2.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 0.5 h / 0 - 20 °C 2.2: 0 - 20 °C

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2008/133753, 2008, A2

80
[ 2516-96-3 ]
[ 1074-36-8 ]
2-((4-carboxyphenyl)thio)-5-nitrobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium hydroxide In ethanol Reflux;	5 2-((4-Carboxyphenyl)thio)-5-nitrobenzoic acid (23) To a solution of 5-nitro-2-chlorobenzoic acid (19.2 g, 95.3 mmol) in absolute ethanol (300 mL) was added a solution of 4-mercaptobenzoic acid (16.1 g, 105 mmol) and potassium hydroxide (14.0 g, 250 mmol) in ethanol (600 mL) while stirring. The reaction mixture was refluxed overnight. The warm mixture was then concentrated in vacuo, water was added, and the mixture was acidified to pH 2 with conc HCl. The resulting solid was filtered and washed with water. The crude product was crystallized from 80% aq ethanol to obtain 2-((4-carboxyphenyl)thio)-5-nitrobenzoic acid (23) (24.4 g, 81%) as light-yellow crystals, mp 238-240 °C. The spectral data were as follows: 1H NMR (400 MHz, DMSO-d6) δ 13.7 (br s, 2H), 8.62 (d, J = 2.7 Hz, 1H), 8.16 (dd, J = 9.0, 2.7 Hz, 1H), 8.05 (d, J = 8.5 Hz, 2H), 7.71 (d, J = 8.5 Hz, 2H), 6.91 (d, J = 9.0 Hz, 1H).; 13C NMR (100 MHz, DMSO-d6) δ 167.34, 166.46, 151.11, 144.82, 136.59, 136.05, 132.86, 131.72, 128.44, 128.11, 127.39, 126.42. HRMS (ESI/IT-TOF) m/z: [M - H]+ calcd for C14H8NO6S 318.0078, found 318.0070.

Reference： [1]Li, Lingzi; Ndzeidze, Gilbert N.; Steinmetz, Mark G. [Tetrahedron, 2019, vol. 75, # 1, p. 70 - 83]

81
[ 87-82-1 ]
[ 1074-36-8 ]
4,4',4'',4''',4'''',4'''''-(benzene-1,2,3,4,5,6-hexaylhexakis(sulfanediyl))hexabenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; Inert atmosphere;

Reference： [1]Chen, Guilin; Zhou, Zaicai; Feng, Hui; Zhang, Chenyan; Wang, Yifan; Qian, Zhaosheng; Pan, Jianwei [Chemical Communications, 2019, vol. 55, # 33, p. 4841 - 4844]

82
[ 1074-36-8 ]
C₄₀H₂₈B₂ClF₂FeN₇O₇S [ No CAS ]
C₄₇H₃₃B₂F₂FeN₇O₉S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With triethylamine; In dichloromethane; at 20℃;Inert atmosphere;	Complex 3 (0.935 g, 1.03 mmol) and a 50% excess of para-mercaptobenzoicacid (0.240 g, 1.55 mmol) were dissolved in dichloromethane (10 mL) under argon and a solution of triethylamine (0.5 mL, 3.6 mmol) in dichloromethane (10 mL) was added dropwise tothe stirring reaction mixture. Then this mixture was stirred overnight at r.t., washed with 1M aqueous hydrochloric acid (5 mL) and water (5 mL). The obtained dichloromethane solution was dried with Na2SO4, evaporated to dryness in vacuo and the solid residue was purified by column chromatography on silica gel (eluent: dichloromethane - methanol 96:4 (v/v) mixture, Rf=0.50). The major elute was evaporated to dryness, the solid residue was washed with hexane and dried in vacuo. The yield of a red solid product was 0.65 g (62%). Calc. for C47H33B2F2FeN7O9S2: C, 55.38; H, 3.26; N, 9.62. Found (%): C, 55.23;H, 3.37; N, 9.41. MS HR-APPI (positive range) m/z: calcd. forC47H33B2F2FeN7O9S2: 1019.13, found: 1019.13. 1H NMR (CD3CN, delta,ppm) 2.48 (m, 1H, CH), 4.12 (m, 2H, CH2N), 7.28 (d, 2H, ArCOO), 7.32(d, 2H, ArCON), 7.37 - 7.41 (m, 20H, Ph), 7.72 (d, 2H, ArCON), 7.90(d, 2H, ArCOO). 13C{1H} NMR (CD3CN, delta, ppm) 29.63 (s, CH2N), 71.81(s, HC?C), 81.24 (s, HC?C), 129.12 (s, Ph), 129.93 (s, Ph), 130.22 (s,Ar), 130.57 (s, Ar), 131.26 (s, Ph), 131.27 (s, Ph), 131.36 (s, Ar),131.41 (s, Ar), 134.25, 134.28 (both s, ipso-Ar), 136.41, 138.53 (both s,ipso-SAr), 147.07, 147.70 (both s, SC=N), 158.55 (s, PhC=N),166.49, 166.98 (both s, C=O). 11B NMR (CD3CN, delta, ppm) 3.69 (two d,J11B-19F=17 Hz, O3BF). 19F NMR (CD3CN, delta, ppm) -168.04 (m,O3BF). UV-vis (CH2Cl2), lambdamax, nm(epsilon·10-3, mol-1 l cm-1): 252(47),265(4.3), 285(3.9), 366(3.7), 403(2.2), 481(27), 511(2.0).

Reference： [1]Inorganica Chimica Acta,2019,vol. 496

83
[ 62595-74-8 ]
[ 1074-36-8 ]
4-((2,6-dioxopiperidin-3-yl)thio)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h;	Step A: 4-((2,6-dioxopiperidin-3-yl)thio)benzoic acid (I-10). A mixture of 4- mercaptobenzoic acid (200 mg, 1.30 mmol), <strong>[62595-74-8]3-bromopiperidine-2,6-dione</strong> (250 mg, 1.30 mmol), and Cs2CO3 (509 mg, 1.56 mmol) in DMF (20 mL) was stirred for 1 h at rt. To the mixture was added H2O (50 mL) and it was then extracted with EtOAc (50 mL x 2). The combined organic layer was washed with brine (50 mL x 3), dried over Na2SO4, filtered, concentrated in vacuo, and purified by column chromatography (DCM/MeOH = 10/1) to give 4-((2,6-dioxopiperidin-3- yl)thio)benzoic acid (120 mg, 35% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm: 12.98 (s, 1H), 10.98 (s, 1H), 7.88-7.85 (m, 2H), 7.55-7.53 (m, 2H), 4.58-4.55 (dd, J = 4.4 Hz, J = 8.8 Hz, 1H), 2.64-2.53 (m, 2H), 2.29-2.25 (m, 1H), 2.04-1.99 (m, 1). LC-MS: Calculated exact mass = 265.29; Found [M+H]+ = 266.1.

Reference： [1]Patent: WO2019/140387,2019,A1 .Location in patent: Paragraph 00393; 00394

84
[ 62595-74-8 ]
[ 1074-36-8 ]
4-((2,6-dioxopiperidin-3-yl)thio)benzamide [ No CAS ]

Reference： [1]Patent: WO2019/140387,2019,A1

85
[ 1074-36-8 ]
[ 114077-82-6 ]
C₁₃H₉NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	To a solution of <strong>[114077-82-6]4-chloronicotinaldehyde</strong> (10 g, 70.92 mmol, 1.0 eq) in DMF (100 mL) was added 4-mercaptobenzoic acid (13.1 g, 85.11 mmol, 1.2 eq) and K2CO3 (29.4 g, 0.213 mol, 3.0 eq) at room temperature under nitrogen atmosphere. The mixture was stirred at room temperature for 16 h. TLC analysis of the reaction mixture showed full conversion to the desired product. Then the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford PI-c.1 (11 g, 59%).

Reference： [1]Patent: US2019/352288,2019,A1 .Location in patent: Paragraph 0570-0571

86
[ 1074-36-8 ]
C₂₀H₁₈ClNO₄ [ No CAS ]
C₂₇H₂₃NO₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With triethylamine; In acetonitrile; at 20℃; for 2h;Inert atmosphere;	Compound 1 (65 mg, 0.2 mmol) and compound 2 (31 mg, 0.2 mmol) and 1.2 times the equivalent of triethylamine were added to 3 mL of anhydrous acetonitrile, and stirred at room temperature for 2 hours under the protection of argon. Purification by column chromatography gave compound 3 as a yellow solid (67.0 mg, yield 72%).

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 9631 - 9635
[2]Patent: CN110498786,2019,A .Location in patent: Paragraph 0004; 0025

87
[ 1074-36-8 ]
[ 2926-29-6 ]
[ 330-17-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrabutylammonium tetrafluoroborate; sodium bromide In acetonitrile at 20℃; for 10h; Electrolysis; Inert atmosphere;

Reference： [1]Zhu, Xing-Xing; Wang, Huai-Qin; Li, Chen-Guang; Xu, Xiao-Lan; Xu, Jun; Dai, Jian-Jun; Xu, Hua-Jian [Journal of Organic Chemistry, 2021, vol. 86, # 22, p. 16114 - 16120]

88
hydrogen tetrachloroaurate(III) trihydrate [ No CAS ]
[ 1074-36-8 ]
[ 244193-52-0 ]
Au₁₂⁽³⁵⁺⁾*9.2C₁₂H₂₃N₂⁽¹⁺⁾*18C₇H₄O₂S^(2-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With carbon monoxide; sodium hydroxide In water monomer at 25℃; for 24h;

Reference： [1]Lin, Yingzheng; Liu, Jian; Liu, Zhihe; Long, Minnan; Xie, Jianping; Yao, Qiaofeng; Zhang, Bihan; Zhu, Moshuqi [Angewandte Chemie - International Edition, 2022, vol. 61, # 9][Angew. Chem., 2022]

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+

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CAS No. :	1074-36-8	MDL No. :	MFCD00016617
Formula :	C₇H₆O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LMJXSOYPAOSIPZ-UHFFFAOYSA-N
M.W :	154.19	Pubchem ID :	95738
Synonyms :

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.65
TPSA :	76.1 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.54 cm/s

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Log Po/w (iLOGP) :	1.24
Log Po/w (XLOGP3) :	2.39
Log Po/w (WLOGP) :	1.67
Log Po/w (MLOGP) :	1.87
Log Po/w (SILICOS-IT) :	1.5
Consensus Log Po/w :	1.73

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Log S (ESOL) :	-2.68
Solubility :	0.322 mg/ml ; 0.00209 mol/l
Class :	Soluble
Log S (Ali) :	-3.63
Solubility :	0.0362 mg/ml ; 0.000235 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.87
Solubility :	2.1 mg/ml ; 0.0136 mol/l
Class :	Soluble

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

Signal Word:	Danger	Class:	9
Precautionary Statements:	P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501	UN#:	3077
Hazard Statements:	H302-H319-H332-H372-H400	Packing Group:	Ⅲ
GHS Pictogram:

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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.
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[ CAS No. 1074-36-8 ] {[proInfo.proName]}

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