[ CAS No. 60-23-1 ] {[proInfo.proName]}

Name: 60-23-1|2-Aminoethanethiol|95%
Brand: Ambeed
SKU: A381010
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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 60-23-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 60-23-1 ]

SDS Specification

Alternatived Products of [ 60-23-1 ]

Product Details of [ 60-23-1 ]

CAS No. :	60-23-1	MDL No. :	MFCD00008196
Formula :	C₂H₇NS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UFULAYFCSOUIOV-UHFFFAOYSA-N
M.W :	77.15	Pubchem ID :	6058
Synonyms :	cysteamine;β-Mercaptoethylamine;NSC 647528;L 1573;Cystagon;Mercaptamine;Thioethanolamine;Decarboxycysteine;2-Mercaptoethylamine

Calculated chemistry of [ 60-23-1 ]

Physicochemical Properties

Num. heavy atoms :	4
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	22.36
TPSA :	64.82 Å²

Pharmacokinetics

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) :	-7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.05
Log Po/w (XLOGP3) :	-0.43
Log Po/w (WLOGP) :	-0.13
Log Po/w (MLOGP) :	-0.23
Log Po/w (SILICOS-IT) :	-0.12
Consensus Log Po/w :	0.03

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.02
Solubility :	80.5 mg/ml ; 1.04 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.47
Solubility :	26.4 mg/ml ; 0.342 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.32
Solubility :	37.4 mg/ml ; 0.484 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 60-23-1 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P270-P272-P280-P273-P302+P352-P305+P351+P338-P310-P330-P363-P403-P501	UN#:	3335
Hazard Statements:	H302-H317-H318-H412	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 60-23-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 60-23-1 ]
Downstream synthetic route of [ 60-23-1 ]

[ 60-23-1 ] Synthesis Path-Upstream 1~14

1
[ 60-23-1 ]
[ 123-90-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 20, p. 3784 - 3786

2
[ 75-07-0 ]
[ 60-23-1 ]
[ 24050-16-6 ]
[ 2346-00-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 1998, vol. 46, # 1, p. 224 - 227

3
[ 60-23-1 ]
[ 75-05-8 ]
[ 2346-00-1 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1954, vol. 590, p. 55,61

4
[ 60-23-1 ]
[ 927-80-0 ]
[ 2346-00-1 ]

Reference： [1] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1954, vol. 57, p. 281,282

5
[ 60099-09-4 ]
[ 60-23-1 ]
[ 504-79-0 ]
[ 290-87-9 ]

Reference： [1] Tetrahedron Letters, 1982, vol. 23, # 47, p. 4903 - 4906
[2] Tetrahedron Letters, 1982, vol. 23, # 47, p. 4903 - 4906
[3] Tetrahedron Letters, 1982, vol. 23, # 47, p. 4903 - 4906

6
[ 105-39-5 ]
[ 60-23-1 ]
[ 20196-21-8 ]

Yield	Reaction Conditions	Operation in experiment
18%	With potassium carbonate In ethanol at 20 - 75℃; for 26 h;	To a solution of 2-aminoehtane-1-thiol (4.5 g, 40 mmol, 1.0 equiv) and K₂CO₃ (5.5 g, 40 mmol, 1.0 equiv.) in EtOH (80 mL) was added ethyl chloroacetate (40 mmol, 1 equiv). The resulting solution was stirred at room temperature for 2 h and at 75 °C for 24 h. After filtration, all volatiles were removed in vacuo. The crude product was purified by flash column chromatography (SiO₂, EtOAc) to give thiomorpholin-3-one as white solid in 18percent yield.

Reference： [1] Tetrahedron, 2015, vol. 71, # 37, p. 6349 - 6353

7
[ 1369959-37-4 ]
[ 60-23-1 ]
[ 2896-98-2 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 14, p. 2739 - 2741,3

8
[ 292638-85-8 ]
[ 60-23-1 ]
[ 2896-98-2 ]

Reference： [1] Chemische Berichte, 1963, vol. 96, p. 88 - 92

9
[ 1362772-43-7 ]
[ 60-23-1 ]
[ 2896-98-2 ]
[ 6265-93-6 ]

Reference： [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 45, p. 10690 - 10693

10
[ 60-23-1 ]
[ 140-88-5 ]
[ 2896-98-2 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1977, vol. 15, p. 720 - 726

11
[ 60-23-1 ]
[ 298-12-4 ]
[ 16310-13-7 ]

Reference： [1] Bioconjugate Chemistry, 2017, vol. 28, # 2, p. 325 - 329
[2] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 8, p. 1180 - 1183
[3] Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 272, p. 1515 - 1517
[4] Comptes rendus hebdomadaires des séances de l'Académie des sciences, 1963, vol. 256, p. 4114 - 4116

12
[ 20461-86-3 ]
[ 60-23-1 ]
[ 16310-13-7 ]

Reference： [1] Ukrainskii Khimicheskii Zhurnal (Russian Edition), 1958, vol. 24, p. 632,634[2] Chem.Abstr., 1959, p. 12281

13
[ 60-23-1 ]
[ 10191-60-3 ]
[ 26364-65-8 ]

Yield	Reaction Conditions	Operation in experiment
67.1%	for 3 h; Heating / reflux	Reference Example 1 To 500 ml of ethanol 146.24 g of dimethyl N-cyanoiminodithiocarbonate ester (1 mole) and 77.15 g of 2-aminoethane thiol (1 mole) were added.. The mixture was heated and refluxed under agitation for 3 hours.. After the end of the reaction, the mixture was cooled to room temperature, then the precipitated crystals were filtered.. The crystals thus obtained were washed with ethanol, then dried to obtain 85.25 g of the above compound. (If making the purity of the above product 100percent, the yield of the N-cyanoiminothiazolidine becomes 67.1percent.)

Reference： [1] Patent: WO2018/157800, 2018, A1, . Location in patent: Paragraph 0997-0999
[2] Patent: EP1460068, 2004, A1, . Location in patent: Page 5
[3] Archiv der Pharmazie, 1972, vol. 305, # 10, p. 731 - 737

14
[ 24771-25-3 ]
[ 60-23-1 ]
[ 26364-65-8 ]

Reference： [1] Organic Preparations and Procedures International, 1991, vol. 23, # 6, p. 721 - 728

[ 60-23-1 ] Synthesis Path-Downstream 1~87

1
[ 100-52-7 ]
[ 60-23-1 ]
[ 4569-82-8 ]

Reference： [1]Organic Magnetic Resonance,1981,vol. 17,p. 68 - 70
[2]Tetrahedron,1990,vol. 46,p. 6545 - 6552
[3]Justus Liebigs Annalen der Chemie,1954,vol. 590,p. 55,61
[4]Mendeleev Communications,2009,vol. 19,p. 92 - 93

3
[ 3025-95-4 ]
[ 60-23-1 ]
[ 502484-68-6 ]
[ 1801-61-2 ]

Reference： [1]Journal of the Chemical Society,1951,p. 3425

4
[ 110-67-8 ]
[ 60-23-1 ]
[ 98548-74-4 ]

Reference： [1]Tohoku Yakka Daigaku Kiyo,1958,p. 43
Chem.Abstr.,1958,p. 10176

5
[ 1071-37-0 ]
[ 60-23-1 ]
[ 1190-74-5 ]

Reference： [1]Patent: DE567015,1926,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 18,p. 3072
[2]Patent: US1785916,1927,

6
[ 60-23-1 ]
[ 75-05-8 ]
[ 2346-00-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1954,vol. 590,p. 55,61

7
[ 60-23-1 ]
[ 927-80-0 ]
[ 2346-00-1 ]

Reference： [1]Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences,1954,vol. 57,p. 281,282

8
[ 60-23-1 ]
[ 107-35-7 ]

Yield	Reaction Conditions	Operation in experiment
98.4%	With 2,2,6,6-tetramethyl-piperidine In water at 140℃; for 0.166667h;	1-4 8.4g of V-Y(30) molecular sieve catalyst with a V loading of 3wt% is pre-added to the oxidation reactor,Additive tetramethylpiperidine: 0.25g, amino mercaptan aqueous solution (28wt%) 1000g,After the temperature is increased to 140°C, air is introduced for oxidation, and the pressure is adjusted to 0.4Mpa,The oxidation time is 10min, after the reaction is over, filter,After crystallization and other post-treatments, 396.2 g of the final taurine product was obtained, with an oxidation yield of 98.4%.
	With dihydrogen peroxide; acetic acid

Reference： [1]Current Patent Assignee: WANHUA CHEMICAL GROUP CO LTD - CN111362845, 2020, A Location in patent: Paragraph 0036; 0039-0041; 0044-0045; 0048-0049; 0052
[2]Ratschinskii et al. [Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2998,3001,3002;engl.Ausg.S.3027,3028,3030]

9
[ 2379-60-4 ]
[ 60-23-1 ]
7-nitro-3,4-dihydro-2H-[1,4]thiazino[2,3-b]quinoxaline [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1970,vol. 47,p. 1150 - 1152

10
[ 2025-40-3 ]
[ 60-23-1 ]
[ 4569-82-8 ]

Reference： [1]Chemische Berichte,1969,vol. 102,p. 522 - 527

11
[ 292638-85-8 ]
[ 60-23-1 ]
[ 2896-98-2 ]

Reference： [1]Chemische Berichte,1963,vol. 96,p. 88 - 92

12
[ 24973-22-6 ]
[ 60-23-1 ]
[ 67189-28-0 ]

Reference： [1]European Journal of Medicinal Chemistry,1978,vol. 13,p. 149 - 151

13
[ 60-23-1 ]
[ 10191-60-3 ]
[ 26364-65-8 ]

Yield	Reaction Conditions	Operation in experiment
67.1%	In ethanol; for 3h;Heating / reflux;	Reference Example 1 To 500 ml of ethanol 146.24 g of dimethyl N-cyanoiminodithiocarbonate ester (1 mole) and 77.15 g of 2-aminoethane thiol (1 mole) were added.. The mixture was heated and refluxed under agitation for 3 hours.. After the end of the reaction, the mixture was cooled to room temperature, then the precipitated crystals were filtered.. The crystals thus obtained were washed with ethanol, then dried to obtain 85.25 g of the above compound. (If making the purity of the above product 100%, the yield of the N-cyanoiminothiazolidine becomes 67.1%.)

Reference： [1]Patent: WO2018/157800,2018,A1 .Location in patent: Paragraph 0997-0999
[2]Patent: EP1460068,2004,A1 .Location in patent: Page 5
[3]Archiv der Pharmazie,1972,vol. 305,p. 731 - 737

14
[ 60-23-1 ]
[ 939-69-5 ]
[ 2590-08-1 ]

Reference： [1]Journal of Organic Chemistry,1965,vol. 30,p. 2344 - 2348

15
[ 60-23-1 ]
[ 140-88-5 ]
[ 2896-98-2 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1977,vol. 15,p. 720 - 726

16
[ 60-23-1 ]
[ 2958-87-4 ]
8-chloro-3,4-dihydro-2H-[1,4]thiazino[2,3-b]quinoxaline [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1970,vol. 47,p. 1150 - 1152

17
[ 591-11-7 ]
[ 60-23-1 ]
7-(1-hydroxyethyl)-<1,4>-thiazepan-5-one [ No CAS ]
7-(1-hydroxyethyl)-<1,4>-thiazepan-5-one [ No CAS ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 10701 - 10708

18
[ 4434-13-3 ]
[ 60-23-1 ]
[ 120332-30-1 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 1528 - 1532

19
[ 4744-50-7 ]
[ 60-23-1 ]
[ 134150-47-3 ]

Reference： [1]Archiv der Pharmazie,1991,vol. 324,p. 185 - 187

20
[ 70-18-8 ]
[ 13244-81-0 ]
[ 27025-41-8 ]
[ 60-23-1 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 123 - 127

21
[ 35231-44-8 ]
[ 60-23-1 ]
[ 133932-27-1 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2268 - 2274

22
[ 27025-41-8 ]
[ 60-23-1 ]
[ 70-18-8 ]
[ 13244-81-0 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 123 - 127

23
[ 69-78-3 ]
[ 60-23-1 ]
[ 15139-21-6 ]
[ 71899-86-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1101 - 1105

24
[ 6575-00-4 ]
[ 60-23-1 ]
[ 96159-89-6 ]

Reference： [1]European Journal of Medicinal Chemistry,1985,vol. 20,p. 16 - 24

25
[ 76972-25-3 ]
[ 60-23-1 ]
9b-(2,3-Dimethyl-phenyl)-2,3-dihydro-9bH-thiazolo[2,3-a]isoindol-5-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2526 - 2535

26
[ 32673-41-9 ]
[ 60-23-1 ]
[ 38603-70-2 ]

Reference： [1]Archiv der Pharmazie,1980,vol. 313,p. 544 - 549

27
[ 201230-82-2 ]
[ 60-23-1 ]
[ 2682-49-7 ]

Reference： [1]Phosphorus and Sulfur and the Related Elements,1988,vol. 38,p. 137 - 148
[2]Tetrahedron,2002,vol. 58,p. 7805 - 7808

28
[ 38585-62-5 ]
[ 60-23-1 ]
[ 38603-73-5 ]

Reference： [1]Archiv der Pharmazie,1980,vol. 313,p. 544 - 549

29
[ 100361-18-0 ]
[ 60-23-1 ]
[ 124256-17-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 2190 - 2196

30
[ 135544-68-2 ]
[ 60-23-1 ]
[ 135920-21-7 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 3489 - 3492

31
[ 60-23-1 ]
[ 126-84-1 ]
[ 22907-30-8 ]

Reference： [1]European Journal of Medicinal Chemistry,1984,vol. 19,p. 119 - 122

32
[ 60-23-1 ]
[ 19179-31-8 ]
[ 96159-91-0 ]

Reference： [1]European Journal of Medicinal Chemistry,1985,vol. 20,p. 16 - 24

33
[ 24424-99-5 ]
[ 60-23-1 ]
[ 67385-09-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 4h; Inert atmosphere;
98%	In lithium hydroxide monohydrate at 20℃; for 4h; Inert atmosphere;
79.9%	With triethylamine In dichloromethane at 12℃; for 16h;	1.25.1 1.25.1 Preparation of Compound 2 To a solution of compound 1 (10 g, 129.8 mmol) in DCM (150 mL) added Boc2O (28 g, 129.8 mmol) followed by TEA (19.7 g, 194.7 mmol). The mixture was stirred at 12° C. for 16 h. The mixture was concentrated to give the crude product, which was purified by chromatography on silica gel PE:EA (10:1) to give compound 2 as colorless oil (18.3 g, 79.9%).

79.9%	With triethylamine In dichloromethane at 12℃; for 16h;	I.1.25.1 1.25.1 Preparation of Compound 2 To a solution of compound 1 (10 g, 129.8 mmol) in DCM (150 mL) added Boc2O (28 g, 129.8 mmol) followed by TEA (19.7 g, 194.7 mmol). The mixture was stirred at 12° C. for 16 h. The mixture was concentrated to give the crude product, which was purified by chromatography on silica gel PE:EA (10:1) to give compound 2 as colorless oil (18.3 g, 79.9%).
26%	With Sodium hydrogenocarbonate In lithium hydroxide monohydrate; acetonitrile at 0 - 20℃; for 4h;	87.1 rM)utyl(2-mercaptoethyl)carbamate (339): To the stirred solution of 2- aminoethane-1 -thiol (1.0 g, 12.96 mmol) in acetonitrile(10 mL)/ water (5 mL), NaHCCh (2.18 g, 25.92 mmol) was added. Then di-tert-butyldicarbonate (5.66 g, 25.92 mmol) was added slowly at 0 °C and the reaction mixture was stirred at room temperature for 4 h. The progress of the reaction was monitored by TLC. After completion of starting material, reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (2 X 100 mL). The combined organic layer was dried over anhydrous NazSCh and concentrated under reduced pressure to get crude compound. The obtained crude compound was purified by silica gel column chromatography using 5% methanol in DCM to afford 600 mg (26% yield) of tert-butyl (2-mercaptoethyl) carbamate (339) as a colorless gum. rH NMR (400 MHz, CDCh) 5 ppm: 5.02 (s, 1H), 3.44 (q, J= 6.0 Hz, 2H), 2.79 (t, J= 6.4 Hz, 2H), 2.67-2.62 (m, 1H), 1.49-1.44(m, 9H).
	With N-ethyl-N,N-diisopropylamine In acetonitrile at 0℃; for 0.5h;
	With triethylamine In dichloromethane at 20℃;
	With triethylamine In dichloromethane at 20℃; Inert atmosphere;	9 REFERENCE EXAMPLE 9tert-butyl N-(2-sulfanylethyl)carbamate Into a 2000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-aminoethane-1-thiol (50 g, 648.10 mmol, 1.00 equiv), dichloromethane (1000 mL), di-tert-butyl dicarbonate (116 g, 531.51 mmol, 1.20 equiv), and TEA (134 g, 1.32 mol, 3.00 equiv). The resulting solution was stirred overnight at room temperature. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of 100 mL of water. The resulting mixture was washed with 2x500 mL of 0.5N hydrogen chloride and 2x500 mL of Brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:8) to give the title compound.
	In lithium hydroxide monohydrate at 20℃; for 6h; Inert atmosphere;	1 Example 1: Preparation of an amine compound represented by the formula (2-1) To a 50 mL round flask was added 17 mL of distilled water2-aminoethanethiolAnd 21.27 g of ditertiary butyl dicarbonateAnd the reaction was carried out in an argon atmosphere to separate the final product TBMC.Then add 13.69 g of the synthesized TBMC and 26.93 ml of triethylamine to the 50-mL round-bottomed flask with argon.Thereafter, an ice bath was installed and 4.15 g (0.035 mol) of divinylsulfone (DVS) was added slowly at 0 ° C.The reaction was allowed to proceed at room temperature for 24 hours. 4.149 g of high purity white powder of sulfonyldicarbamate was obtained.

Reference： [1]Wang, Yanyan; Fan, Jingwei; Darensbourg, Donald J. [Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10206 - 10210][Angew. Chem., 2015, vol. 127, # 35, p. 10344 - 10348,5]
[2]Hossain, Khohinur; Florean, Luca; Del Tedesco, Anna; Cattaruzza, Elti; Geppi, Marco; Borsacchi, Silvia; Canton, Patrizia; Benedetti, Alvise; Riello, Pietro; Scarso, Alessandro [Chemistry - A European Journal, 2021, vol. 27, # 71, p. 17941 - 17951]
[3]Current Patent Assignee: JOHNSON & JOHNSON INC - US2015/197493, 2015, A1 Location in patent: Paragraph 0648; 0649; 0650
[4]Current Patent Assignee: JOHNSON & JOHNSON INC - US2015/225355, 2015, A1 Location in patent: Paragraph 0644
[5]Current Patent Assignee: ELUCIDA ONCOLOGY - WO2022/93800, 2022, A2 Location in patent: Paragraph 00868-00869
[6]Saha, Uttam K.; Roy, Rene [Journal of the Chemical Society. Chemical communications, 1995, # 24, p. 2571 - 2574]
[7]Suzuki, Takayoshi; Hisakawa, Shinya; Itoh, Yukihiro; Suzuki, Nobuaki; Takahashi, Katsumasa; Kawahata, Masatoshi; Yamaguchi, Kentaro; Nakagawa, Hidehiko; Miyata, Naoki [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4208 - 4212]
[8]Current Patent Assignee: MERCK & CO INC - WO2016/206101, 2016, A1 Location in patent: Page/Page column 45; 46
[9]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - KR2018/103401, 2018, A Location in patent: Paragraph 0144; 0145; 0147; 0148

34
[ 69-78-3 ]
[ 60-23-1 ]
[ 71899-86-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	In water; acetonitrile;	2-Aminoethanethiol (1.0 g, 13.0 mmol) and 5,5'-dithio-bis(2-nitrobenzoic acid) (1.75 g, 4.4 mmol) were combined in acetonitrile (100 mL) and water (25 mL) and stirred at room temperature for 14 hr. The reaction mixture was diluted with water (450 mL) and purified by preparative reverse phase HPLC on a Waters Delta Prep 4000 with a Vydac 5.0*2.5 cm preparative C-18 column to give 8a (1.0 g, 40%) 1H NMR (D2O): delta7.95 (d, 1H, J=8.7 Hz), 7.61 (dd, 1H, J=8.7, 2.2 Hz), 7.58 (d, 1H, J=2.2 Hz), 3.18 (t, 2H, J=6.5 Hz), 2.92 (t, 2H, J=6.7 Hz).

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 5891 - 5896
[2]Patent: US6307018,2001,B1

35
[ 3984-34-7 ]
[ 60-23-1 ]
[ 182957-13-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	With toluene-4-sulfonic acid In butan-1-ol for 2h; Heating;
	Yield given;

Reference： [1]Trapani, Giuseppe; Franco, Massimo; Latrofa, Andrea; Carotti, Angelo; Cellamare, Saverio; Serra, Mariangela; Ghiani, Cristina A.; Tuligi, Graziella; Biggio, Giovanni; Liso, Gaetano [Journal of Pharmacy and Pharmacology, 1996, vol. 48, # 8, p. 834 - 840]
[2]Aicher, Thomas D.; Knorr, Douglas C.; Smith, Howard C. [Tetrahedron Letters, 1998, vol. 39, # 47, p. 8579 - 8580]

36
[ 76-83-5 ]
[ 60-23-1 ]
[ 1095-85-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With chloro-trimethyl-silane; acetic acid at 40℃; for 4h;	7.7.3 7.3. Add 100g (1.3mol) of 2-mercaptoethylamine to glacial acetic acid, increase the temperature, then add 525.2g (1.625mol) of triphenylchloromethane, then slowly add 155.3g (1.43mol) of trimethylchlorosilane, mechanical The temperature was raised to 40 and reacted for 4h under stirring, and then the temperature was lowered to about 5. The pH value of the system was adjusted with 20% by mass sodium acetate aqueous solution and stirred for crystallization. Then the system was filtered and the filter cake was washed with water and ether to obtain S -Tritylcysteamine, dried to obtain 347.9g (84%, 1.09mol).
80%	With trifluoroacetic acid at 20℃; for 3h; Inert atmosphere;
80%	With trifluoroacetic acid at 20℃; for 3h;	1 Preparation of 2-(tritylthio)ethanamine (1): Example 1 N-allyl-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-N-(2-(tritylthio)ethyl)acetamide (3) Preparation of 2-(tritylthio)ethanamine (1): To a 500 Ml round bottom flastk is charged trifluoroacetic acid (100 Ml), cysteamine (6.9 g, 89.6 mmol) and trityl chloride (25 g, 89.6 mmol). The mixture was stirred for 3 hours at room temperature. The trifluoroacetic acid was removed in vacuo and 2M NaOH (500 Ml) was added. The precipitate which formed was collected by filtration, the filtrate washed with water and hexane then dried to afford 2.4 g (80%) of the desired product as a white solid. 1H NMR (400 MHz, Chloroform-d) δ 7.50-7.40 (m, 6H), 7.33-7.25 (m, 6H), 7.25-7.19 (m, 3H), 2.60 (t, J=6.5 Hz, 2H), 2.33 (t, J=6.5 Hz, 2H), 1.08 (s, 2H). 13C NMR (101 MHz, Chloroform-d) δ 145.01, 129.70, 127.97, 126.75, 66.64, 41.20, 36.47. Mass: C21H21NS[M+H]+ Calculated: 319.1395, Found: 319.1527.

77%	In N,N-dimethyl-formamide at 20℃;
69%
61%	In N,N-dimethyl-formamide at 20℃;	Synthesis of 19: A solution of cysteamine (200mg, 2.59mmol) and trityl chloride (725mg, 2.60mmol) in anhydrous DMF (10mL) was stirred at room temperature overnight. Then, 20mL of water was added, and the mixture was extracted with EtOAc (2x30mL), washed with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with MeOH:CH2Cl2 (4:96) to obtain 17 (505mg, 1.58mmol, 61%) as a yellow oil. 1H NMR (300MHz, CDCl3): δ 7.48-7.41 (m, 6H, Trt); 7.33-7.18 (m, 9H, Trt); 2.58 (t, J=6.7Hz, 2H, CH2-NH2); 2.36 (t, J=6.7Hz, 2H, CH2-STrt); 2.03 (s, 2H, NH2). 13C NMR (75MHz, CDCl3): δ 145.0 (C, Trt); 129.7 (CH, Trt); 128.0 (CH, Trt); 126.8 (CH, Trt); 66.7 (C, Trt); 40.9 (CH2-NH2); 35.8 (CH2-STrt). HRMS (ESI+) m/z: [M+H]+ calcd. For C21H22NS: 320.1467; found: 320.1466.
61%	In N,N-dimethyl-formamide at 20℃;	Synthesis of 19: A solution of cysteamine (200mg, 2.59mmol) and trityl chloride (725mg, 2.60mmol) in anhydrous DMF (10mL) was stirred at room temperature overnight. Then, 20mL of water was added, and the mixture was extracted with EtOAc (2x30mL), washed with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with MeOH:CH2Cl2 (4:96) to obtain 17 (505mg, 1.58mmol, 61%) as a yellow oil. 1H NMR (300MHz, CDCl3): δ 7.48-7.41 (m, 6H, Trt); 7.33-7.18 (m, 9H, Trt); 2.58 (t, J=6.7Hz, 2H, CH2-NH2); 2.36 (t, J=6.7Hz, 2H, CH2-STrt); 2.03 (s, 2H, NH2). 13C NMR (75MHz, CDCl3): δ 145.0 (C, Trt); 129.7 (CH, Trt); 128.0 (CH, Trt); 126.8 (CH, Trt); 66.7 (C, Trt); 40.9 (CH2-NH2); 35.8 (CH2-STrt). HRMS (ESI+) m/z: [M+H]+ calcd. For C21H22NS: 320.1467; found: 320.1466.
58%	With trifluoroacetic acid In dichloromethane at 25℃; for 2h; Inert atmosphere;
17%	In dichloromethane; N,N-dimethyl-formamide at 20℃;	1 Synthesis of MB220. Cysteamine (1.39 g, 18.0 mmol) was dissolved in CH2CI2:DMF (1 :1 , 50 ml_). Trityl chloride (5.10 g, 18.3 mmol) was added, and the solution was stirred o/n at r.t.. Then, the mixture was concentrated in vacuo and subsequently co concentrated with toluene (50 ml_), ethanol (50 ml_), and dichloromethane (50 ml_). The crude product was dissolved in dichloromethane (50 ml_) and washed with saturated aq. NaHCO3(30 ml_). The organic phase was dried, filtered, and concentrated in vacuo. The product was purified by using a Reveleris auto flash system (Buchi FP ID HP Si 24g NP- cartridge, 1 : 4CV at 0% CH3OH in CH2CI2, 2: 8CV from 0-4% CH3OH in CH2CI2, 3CV at 4% CH3OH in CH2CI2, 5CV at 20% CH3OH in CH2CI2, temp.: 25 °C, detection: UV220/254nm) to yield a white pure compound (1009 g, 17 % yield). MALDI-TOF MS ( m/z): Calc mass C21H21NS 319.14; found mass [M+Na]+342.28.1H NMR (400 MHz, CD3OD), d (ppm): 7.51 - 7.19 (m, 15H), 2.51 - 2.45 (m, 2H), 2.43 - 2.36 (m, 2H).
	In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	1.1.1-3.1.1 1) synthesizing a kind of polyethylene glycol polypyrimidine polylactic acid glycolic acid derivative material modified by AptamerAS1411 (1) Weigh 2.04g of β-mercaptoethylamine and 5g of triphenylchloromethane, dissolve in 100mL of tetrahydrofuran, under nitrogen protection, react at room temperature for 3 hours, remove the solvent under reduced pressure, add 2 moles per liter of aqueous sodium hydroxide solution, After the solid is separated out, use pure water and n-hexane to wash several times to obtain a sulfhydryl protected product;

Reference： [1]Current Patent Assignee: GL BIOCHEM SHANGHAI - CN111704566, 2020, A Location in patent: Paragraph 0056; 0058
[2]Xi, Weixian; Pattanayak, Sankha; Wang, Chen; Fairbanks, Benjamin; Gong, Tao; Wagner, Justine; Kloxin, Christopher J.; Bowman, Christopher N. [Angewandte Chemie - International Edition, 2015, vol. 54, # 48, p. 14462 - 14467][Angew. Chem., 2015, vol. 127, # 48, p. 14670 - 14675,6]
[3]Current Patent Assignee: UNIVERSITY OF COLORADO (SYSTEM) - US10508116, 2019, B2 Location in patent: Page/Page column 9; 11
[4]Li, Minfeng; Yamato, Kazuhiro; Ferguson, Joseph S.; Gong, Bing [Journal of the American Chemical Society, 2006, vol. 128, # 39, p. 12628 - 12629]
[5]Cepas, Susana Caveda; North, Michael [Tetrahedron, 1997, vol. 53, # 49, p. 16859 - 16866]
[6]Balado, Miguel; Cisneros-Sureda, Javier; Lemos, Manuel L.; Rey-Varela, Diego; Jiménez, Carlos; Rodríguez, Jaime [Journal of Inorganic Biochemistry, 2022, vol. 230]
[7]Balado, Miguel; Cisneros-Sureda, Javier; Lemos, Manuel L.; Rey-Varela, Diego; Jiménez, Carlos; Rodríguez, Jaime [Journal of Inorganic Biochemistry, 2022, vol. 230]
[8]Togashi, Masataka; Terai, Takuya; Kojima, Hirotatsu; Hanaoka, Kenjiro; Igarashi, Kazuei; Hirata, Yasunobu; Urano, Yasuteru; Nagano, Tetsuo [Chemical Communications, 2014, vol. 50, # 95, p. 14946 - 14948]
[9]Current Patent Assignee: TECHNICAL UNIVERSITY OF DENMARK - WO2020/249745, 2020, A1 Location in patent: Page/Page column 52
[10]Current Patent Assignee: FUDAN UNIVERSITY - CN114053248, 2022, A Location in patent: Paragraph 0037; 0044-0046; 0061-0064; 0079-0080

37
[ 75-07-0 ]
[ 60-23-1 ]
[ 24050-16-6 ]
[ 2346-00-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,1998,vol. 46,p. 224 - 227

38
[ 153493-48-2 ]
[ 60-23-1 ]
7,8-dihydro-6H-2-oxa-5-thia-1,3,4,8,9-pentaaza-cyclopenta[b]naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In acetonitrile at 20℃; for 1h;

Reference： [1]Starchenkov; Andrianov [Chemistry of Heterocyclic Compounds, 1997, vol. 33, # 11, p. 1352 - 1354]

39
[ 24771-25-3 ]
[ 60-23-1 ]
[ 26364-65-8 ]

Reference： [1]Organic Preparations and Procedures International,1991,vol. 23,p. 721 - 728

40
[ 60-23-1 ]
[ 96036-03-2 ]
(4R,5S)-3-((3S,5S)-5-Dimethylcarbamoyl-pyrrolidin-3-ylsulfanyl)-5-[(1R,2R)-2-hydroxy-1-(2-mercapto-ethylcarbamoyl)-propyl]-4-methyl-4,5-dihydro-3H-pyrrole-2-carboxylic acid [ No CAS ]

Reference： [1]Xenobiotica,1994,vol. 24,p. 185 - 198

41
[ 2346-00-1 ]
[ 7647-01-0 ]
[ 60-23-1 ]

Reference： [1]Chemische Berichte,1891,vol. 24,p. 1117

44
[ 60-23-1 ]
[ 241820-93-9 ]
[ 261518-54-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium In ethanol at 20℃; for 12h;
50%	With sodium ethanolate In ethanol at 20℃; for 18h;
50%	With sodium ethanolate In ethanol at 20℃; for 18h;	53 figure 53 shows scheme for synthesis of neomycin isothiocyanate. Reaction conditions: (i) (a) (Boc)2O, DMF, H2O, Et3N, 60 °C, 5 h, 60%; (b) 2,4,6- triisopropylbenzenesulfonyl chloride, pyridine, room temperature, 40 h, 50%; (c) H2NCH2CH2SH, NaOEt/EtOH, room temperature, 18 h, 50%; (ii) l,l'-thiocarbonyldi- 2(lH)pyridone, 4-N,N-dimethylammopyridine and CH2Cl2 (12 h, room temperature, 60%).; 434. Synthesis of neomycin isothiocyanate (Charles, L, et al. Bioorg Med Chem Lett 2002, 12, 1259-62) 3 (Figure 53) was initiated by conversion of the natural product-neomycin to 5"-deoxy-5"-amino neomycin 2 (Figure 53). Reaction of this amine and l,r-thiocarbonyldi- 2(lH)pyridone (TCDP) in the presence of 4-N,iV-dimethylaminopyridine (DMAP) leads to the formation of isothiocyanate, which can be easily followed by IR spectroscopy (Figure 54).

With ethanol; sodium

Reference： [1]Kamphan, Anothai; Gong, Changjun; Maiti, Krishnagopal; Sur, Souvik; Traiphol, Rakchart; Arya, Dev P. [RSC Advances, 2017, vol. 7, # 66, p. 41435 - 41443]
[2]Charles; Arya, Dev P. [Journal of Carbohydrate Chemistry, 2005, vol. 24, # 2, p. 145 - 160]
[3]Current Patent Assignee: CLEMSON UNIVERSITY - WO2007/16455, 2007, A2 Location in patent: Page/Page column 9; 112; sheet 50
[4]Location in patent: scheme or table Xue, Liang; Xi, Hongjuan; Kumar, Sunil; Gray, David; Davis, Erik; Hamilton, Paris; Skriba, Michael; Arya, Dev P. [Biochemistry, 2010, vol. 49, # 26, p. 5540 - 5552]

45
[ 2127-03-9 ]
[ 60-23-1 ]
[ 83578-21-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In methanol at 20℃; Inert atmosphere;
92%	In methanol at 20℃; for 2h; Inert atmosphere;	2 Preparation of N-(2-((2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19- hexaenamido)ethyl)disulfanyl)-2-methylpropyl)nicotinamide (II-3): [00226] A solution containing 1 ,2-di(pyridin-2-yl)disulfane (26 g, 0.227 mmol) in MeOH (200 mL) was added dropwise at room temperature to a solution containing cysteamine (50 g, 0.227 mmol) in MeOH (200 mL). The resulting reaction mixture was stirred at room temperature for 2 hours under an inert atmosphere of nitrogen and then concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (CH2Cl2/MeOH = 10/1) to afford 2-(pyridin-2-yldisulfanyl)ethan-l -amine (39 g, 92% yield). A mixture containing 2-(pyridin-2-yldisulfanyl)ethan- 1 -amine (5 g, 26.8 mmol), DHA (9.2 g, 26.8 mmol), and HATU (10.2 g, 26.8 mmol) were taken up in CH2CI2 (100 mL) and stirred at room temperature. Triethylamine (18 mL, 40.3 mmol) was then added dropwise at room temperature. The resulting reaction mixture was stirred at room temperature for 18 hours, which was then diluted with water and extracted with CH2CI2. The combined organic layers were washed with water (3 x 100 mL), brine (100 mL), dried over anhydrous Na2S04, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (pentanes/EtOAc) to afford (4Z,7Z, 10Z,13Z, 16Z,19Z)-N-(2-(pyridin-2- yldisulfanyl)ethyl)docosa-4,7, 10, 13, 16, 19-hexaenamide (10 g, 75% yield) as a light brown oil. [00227] l-Amino-2-methylpropane-2 -thiol (1.14 g, 8 mmol) was added dropwise at room temperature to a solution containing (4Z,7Z,10Z, 13Z, 16Z, 19Z)-N-(2-(pyridin-2- yldisulfanyl)ethyl)docosa-4,7, 10,13, 16, 19-hexaenamide (4 g, 8 mmol) in a 1 : 1 mixture of MeOH/DMF (10 mL). The resulting reaction mixture was stirred at room temperature for 18 hours, which was then diluted with water and extracted with EtOAc. The combined organic layers were washed with water (2 *50 mL), brine (50 mL), dried over Na2S04, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (pentanes/EtOAc) to afford (4Z,7Z, 10Z,13Z, 16Z,19Z)-N-(2-((l-amino-2- methylpropan-2-yl)disulfanyl)ethyl)docosa-4,7, 10, 13, 16, 19-hexaenamide (3.2 g, 81% yield) as a light brown oil.
92%	In methanol at 20℃; for 2h; Inert atmosphere;

78.2%	With acetic acid In ethanol Inert atmosphere; Darkness;	3 Compound 6 (13.20 g, 60 mmol) and glacial acetic acid (3.43 ml, 60 mmol) were dissolved in 100 mL of absolute ethanol,While compound 7 (2.31 g, 30 mml) of cysteamine was dissolved in 50 mL of absolute ethanol,The compound 7 was added dropwise to the solution of compound 6 under the conditions of N2 under the protection of N2, and the reaction was carried out overnight. TLC was used to detect the cysteamine reaction in the starting point. The reaction solution was distilled off under reduced pressure and the crude product was purified by column chromatography (Mobile phase C Η 2 C12: Μ 0 H = 2 0: 1) to give 4.12 g as a white solid, yield 78.2%
29.4%	With acetic acid In ethanol Inert atmosphere;	2 Example 2 At room temperature under a nitrogen atmosphere,2-Aminoethanethiol (1.0 g, 13 mmol, 1 eq) and 2,2'-dithiodipyridine (5.7 g, 26 mmol, 2 eq)It was dissolved in a mixed solvent of ethanol:acetic acid (20:1, v:v, 30 mL) and stirred overnight.Evaporate the solvent under reduced pressure.The crude product was purified by preparative column chromatography (ethyl acetate: petroleum ether = 1:1, v: v)The morphology was white wax (0.71 g, 29.4%).
356.0 mg	In methanol; chloroform at 20℃; for 3h;
	Stage #1: 2,2'-dipyridyldisulphide; Cysteamine In methanol; acetic acid for 48h; Inert atmosphere; Stage #2: With sodium hydroxide In water for 0.25h;	1.4 4. Preparation of 2-(pyridyldithio)-ethylamine (PDA) 2.288 g (20 mmol) of 2-mercaptoethylamine was dissolved in 17.5 mL of methanol, followed by mixing with 1.6 mL (26.7 mmol) of glacial acetic acid to form a mixture. 8.815 g (40 mmol) of 2,2'-dipyridyldisulfide was dissolved in 17.5 mL of methanol, followed by dropwise addition into the mixture to form a reaction solution. The reaction solution was subjected to reaction under a nitrogen gas environment for 48 hours, followed by evaporation to remove methanol and obtain a yellow grease. The grease was dissolved in 20 mL of methanol, followed by addition of 100 mL of ether. Addition of ether was repeated six times to obtain a precipitate of 1.95 g (8.8 mmol, 44% of yield) of white-powdery crystalline PDA-HCl.
	With acetic acid In methanol
	With acetic acid In methanol
	With acetic acid In methanol for 48.5h;
	Stage #1: 2,2'-dipyridyldisulphide With acetic acid In methanol at 25℃; for 0.166667h; Stage #2: Cysteamine In methanol for 1h;	5.1 General procedure for preparation of compound 7 To a stirred solution of 2-(2-pyridyldisulfanyl)pyridine (10.67 g, 48.41 mmol, 1.1 eq) in MeOH (50 mL) was added AcOH (2.64 g, 44.01 mmol, 2.52 mL, 1 eq). The mixture was stirred for 10 min at 25°C. Then 2-aminoethanethiol (5 g, 44.01 mmol, 1 eq, HCl salt) in MeOH (50 mL) was added dropwise. The reaction mixture was stirred for another lh. TLC (Dichloromethane: Methanol = 10:1) showed the reaction was complete. The mixture was concentrated in vacuum. MeOH (20 mL) and methyl tert-butyl ether (150 mL) was added. Then the mixture was filtered. The filter cake was dried in vacuum. 2-(2-pyridyldisulfanyl)ethanamine (5.4 g, 24.24 mmol, 55.08% yield, HC1 salt) was obtained as yellow solid.

Reference： [1]Gademann, Karl; Shchelik, Inga S. [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 12, p. 1898 - 1904]
[2]Current Patent Assignee: CATABASIS PHARMACEUTICALS, INC. - WO2016/86103, 2016, A1 Location in patent: Paragraph 00226
[3]Vu, Chi B.; Bridges, Robert J.; Pena-Rasgado, Cecilia; Lacerda, Antonio E.; Bordwell, Curtis; Sewell, Abby; Nichols, Andrew J.; Chandran, Sachin; Lonkar, Pallavi; Picarella, Dominic; Ting, Amal; Wensley, Allison; Yeager, Maisy; Liu, Feng [Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 458 - 473]
[4]Current Patent Assignee: NANTONG UNIVERSITY - CN104829671, 2017, B Location in patent: Paragraph 0083; 0088; 0089
[5]Current Patent Assignee: FUDAN UNIVERSITY - CN109985006, 2019, A Location in patent: Paragraph 0078-0081
[6]Cui, Zhiyong; Sun, Lele; Zhang, Biliang [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 927 - 933]
[7]Sugahara; Uragami; Yan; Regen [Journal of the American Chemical Society, 2001, vol. 123, # 32, p. 7939 - 7940]
[8]Current Patent Assignee: NATIONAL YANG MING CHIAO TUNG UNIVERSITY - US2011/92672, 2011, A1 Location in patent: Page/Page column 4
[9]Location in patent: scheme or table Duvall, Craig L.; Convertine, Anthony J.; Benoit, Danielle S.W.; Hoffman, Allan S.; Stayton, Patrick S. [Molecular Pharmaceutics, 2010, vol. 7, # 2, p. 468 - 476]
[10]Vivero-Escoto, Juan L.; Rieter, William J.; Lau, Honam; Huxford-Phillips, Rachel C.; Lin, Wenbin [Small, 2013, vol. 9, # 20, p. 3523 - 3531]
[11]Ghorbani, Marjan; Hamishehkar, Hamed; Hajipour, Hamed; Arsalani, Naser; Entezami, Ali Akbar [New Journal of Chemistry, 2016, vol. 40, # 4, p. 3561 - 3570]
[12]Current Patent Assignee: BICYCLE THERAPEUTICS LIMITED - WO2019/34866, 2019, A1 Location in patent: Paragraph 00422

46
[ 30754-23-5 ]
[ 60-23-1 ]
heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-cyclodextrin [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 6801 - 6809
[2]Chemistry - A European Journal,2008,vol. 14,p. 7202 - 7211

47
[ 4640-67-9 ]
[ 60-23-1 ]
[ 96159-82-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 407 - 409

48
[ 4548-45-2 ]
[ 32673-41-9 ]
[ 584-08-7 ]
[ 38603-70-2 ]
[ 60-23-1 ]
2-{2-[(1H-Imidazol-4-yl)methylthio]ethylamino}-5-nitropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; aqueous HBr; ethanol; chloroform; water; isopropyl alcohol;	EXAMPLE 104 2-{2-[(1H-Imidazol-4-yl)methylthio]ethylamino}-5-nitropyridine 3 g (22 mmol) of <strong>[32673-41-9]4-hydroxymethyl-1H-imidazole hydrochloride</strong> and one molar equivalent of 2-aminoethanethiol (2.2 g) in 45 ml of aqueous HBr (48%) are brought to reflux for 18 h. The dark-red solution is then evaporated to dryness and the 4-[(2-aminoethyl)thiomethyl]-1H-imidazole dihydrobromide solid residue is washed with 30 ml of an absolute ethanol/ether (1/1) mixture (yield=95%), M.p.: 178-179 C. A solution of 5 g (15mmol) of 4-[(2-aminoethyl)thiomethyl]-1H-imidazole dihydrobromide in 5 ml of water is basified to a pH of 11 with 4.3 g (31 mmol) of K2 CO3 in 15 ml of water. Extraction with 2-propanol provides the amine base which is freed of the inorganic material by subsequent washing with 2-propanol. 2 g (12.7 mmol) of the amine and 2 g (12.7 mmol) of 2-chloro-5-nitropyridine in 20 ml of 2-propanol are brought to reflux for 18 h. On leaving to stand, an orange solid settles and the latter is collected and chromatographed on a column of silica gel which is eluted with a mixture of chloroform and methanol (1, 5, 10 and 20%). The combined fractions are concentrated under reduced pressure to dryness and the resulting solid is purified by preparative reverse-phase high performance liquid chromatography. The product is crystallized from absolute ethanol to give pale-yellow crystals, M.p.: 145-147 C.

Reference： [1]Patent: US5559113,1996,A

49
[ 70165-31-0 ]
[ 60-23-1 ]
5-carboxy-2-(4,5-dihydro-2-thiazolyl)-pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; In ethanol; chloroform; water;	EXAMPLE 1 5-Carboxy-2-(4,5-dihydro-2-thiazolyl)-pyridine Sodium (11 mmol) is added to a flask containing 75 ml of ethanol. As soon as the sodium has dissolved, 10 mmol of 5-carboxy-2-cyanopyridine and 11 mmol of 2-amino-ethanethiol are added and the solution is refluxed for 24 h. The solution is then diluted with 25 ml of water, made acidic (pH=5) with 2N HCl and evaporated. The residue is dissolved in 100 ml of hot chloroform, the salts are filtered off and the filtrate on cooling gives crystals of the title compound, m.p. 234-235 C. The starting material is prepared as follows:

Reference： [1]Patent: US4904675,1990,A

50
[ 60-23-1 ]
[ 2682-49-7 ]

Yield	Reaction Conditions	Operation in experiment
	With selenium; CO; oxygen; In tetrahydrofuran;	EXAMPLE 3 14.8 mmoles of 2-mercaptoethylamine and 0.5 mmole of amorphous Se, in 10 ml of THF, were reacted at 60 C. with a CO:O2 mixture in the molar ratio 10:1 at 3.5 atmospheres. After 4 hours the solution was filtered from selenium and the solvent was evaporated. The residue was again crystallized in CS2 (m.p. = 50 C.). 1.4 g of 2-thiazolidinone were obtained, identified through IR and mass spectoscopy. Yield = 93%.

Reference： [1]Patent: US4042595,1977,A

51
[ 10025-83-9 ]
[ 60-23-1 ]
fac(S)-[Ir(2-aminoethanethiolate)3] [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 661 - 670
[2]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 2582 - 2589

52
[ 60-23-1 ]
[ 13623-94-4 ]
2-(nitromethylene)thiazolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	In ethanol for 8h; Reflux;
68%	In ethanol at 78℃;	Intermediates 25-26. General procedure: The synthetic procedures of intermediates25-26 are shown in equation (4). Tobis(methylsulfane) (10 mmol) in ethanol (20 mL) at 78 °Cwas added commercially available reactants 24 (10 mmol)dropwise, respectively, and the mixture was stirred atreflux 78 °C. After the disappearance of the reactant (monitoredby TLC), the reaction mixture was cooled to roomtemperature during which time the product separated outas a solid. The product was filtered and dried to obtaintarget intermediate.28
31%	With triethylamine In ethanol for 3h; Reflux;	19 Synthesis of Intermediate 2-NitiOmethylene-thiazolidine (1-19a):TEA (1.8 mL, 13.20 mmol) was added to a solution of 1 , 1-bis- methylsulfanyl-2-nitro-ethene (M b: 1.45 g, 8.802 mmol) and 2-amino-ethanethiol (1 g, 8.802 mmol) in ethanol (20 mL). The resulting mixture was heated to reflux for 3 hours. The reaction mixture was monitored by TLC (70% ethylacetate in hexane). The reaction mixture was concentrated to afford the crude product. Purification by column chromatography on silica gel (70% ethylacetate in hexane) afforded 0.6 g of the product (31% yield).1HNMR (300MHz, DMSO-D6): δ 9.2-9.1 (br s, 1 H), 7.2-7.1 (br s, 1 H), 4.0- 3.6 (d, 2H), 3.5-3.1 (d, 2H). LCMS purity: 99.93%, m/z = 147 (M+1)

31%	With triethylamine In ethanol for 3h; Reflux;	19 TEA (1.8 mL, 13.20 mmol) was added to a solution of 1,1-bis-methylsulfanyl-2-nitro-ethene (I-1b: 1.45 g, 8.802 mmol) and 2-amino-ethanethiol (1 g, 8.802 mmol) in ethanol (20 mL). The resulting mixture was heated to reflux for 3 hours. The reaction mixture was monitored by TLC (70% ethylacetate in hexane). The reaction mixture was concentrated to afford the crude product. Purification by column chromatography on silica gel (70% ethylacetate in hexane) afforded 0.6 g of the product (31% yield).1HNMR (300 MHz, DMSO-D6): δ 9.2-9.1 (br s, 1H), 7.2-7.1 (br s, 1H), 4.0-3.6 (d, 2H), 3.5-3.1 (d, 2H). LCMS purity: 99.93%, m/z=147 (M+1)
	In ethanol Reflux;

Reference： [1]Fan, Yefeng; Liu, Song; Chen, Nanyang; Shao, Xusheng; Xu, Xiaoyong; Li, Zhong [Synlett, 2015, vol. 26, # 3, p. 393 - 403]
[2]Chen, Yuce; Cao, Xiaofeng; Chen, Xi; Li, Zhong; Xu, Xiaoyong [Journal of Chemical Research, 2021, vol. 45, # 9-10, p. 835 - 844]
[3]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz); DR REDDY'S LABORATORIES LIMITED - WO2011/54828, 2011, A1 Location in patent: Page/Page column 86
[4]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz); DR REDDY'S LABORATORIES LIMITED - US2011/190334, 2011, A1 Location in patent: Page/Page column 32
[5]Yildirim, Muhammet; Çelikel, Derya; Dürüst, Yaşar; Knight, David W.; Kariuki, Benson M. [Tetrahedron, 2014, vol. 70, # 12, p. 2122 - 2128]

53
[ 1362772-43-7 ]
[ 60-23-1 ]
[ 2896-98-2 ]
[ 6265-93-6 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 10690 - 10693

54
[ 60-23-1 ]
[ 68766-96-1 ]
ethyl (R)-2-amino-4-(4,5-dihydrothiazol-2-yl)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: (a) Pyrrolidone (85 mg, 1 mmol), DCM (10 ml) and pyridine (235 mul, 3.0 mmol) are mixed in a dry 25 ml double necked R.B flask under nitrogen atmosphere. The resulting solution is cooled to -65 C and then neat triflic anhydride (229 mul, 1.3 mmol) is added slowly to the solution. After completion of the addition of Tf2O, the reaction mixture is allowed to warm up to -40 C (approx.1.5 h) then gradually cooled to -60 C and added 2-amino ethanethiol (130 mg, 1.7 mmol) followed by addition of another 235 mul (3.0 mmol) of pyridine and warmed the reaction mixture to -30 C and is allowed to stir for another hour at the same temperature and then allowed to stir for 1.5 h at room temperature. After the optimum completion of the reaction (as per TLC), the reaction mixture is then filtered through silica bed (60-120 mesh) and eluted with diethyl ether. The ethereal filtrate is concentrated and purified using Flash chromatography to obtain thiazolinized product (10a') as yellow colored oil. (In a general observation these products are sensitive to aqueous acid and are not stable enough at room temperature therefore protection of free amino terminal as carbamate is performed.)(b) The ethereal filtrate was taken in a 25 ml R.B. flask and added TEA (187 mul, 1.3 mmol) at 0 C, followed by the addition of benzyl chloroformate (186 mul, 1.5 mmol) or di-tert-butyl carbonate (344 mul, 1.5 mmol) and then allowed the reaction mixture to stir at room temperature for 10-14 h. After the completion of reaction in vacuo distillation is carried out a deep yellow colored crude product was obtained. The desired Cbz or Boc protected thiazolinized product was purified with flash chromatography on silica gel as light yellow colored oil in quantitative yield. (10a).

Reference： [1]Tetrahedron,2012,vol. 68,p. 1272 - 1279

55
[ 85363-04-8 ]
[ 60-23-1 ]
[ 1355646-65-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine; In methanol; at 65℃;	Step 1 : Synthesis of 2-(tert-butoxycarbonylamino-methyl)-4,5-dihydro-thiazoleA solution of N-Boc-aminoacetonitrile (2.0 g), 2-aminoethanol (1 .41 g) and triethyl- amine (0.0.37 mL, 0.27 g) in methanol (23 mL) was heated at 65C over night. After all volatiles were removed in vacuum, toluene (70 mL) and water (30 mL) were added and the mixture was stirred vigorously for 1 h. The layers were separated and the aqueous layer was extracted with toluene. The combined organic layers were dried over Na2S04 and concentrated in vacuum to yield the title compound (2.60 g, 82%).Characterization by 1H-NMR (400 MHz, DMSO-d6):delta [delta] = 1.38 (s, 9H), 3.23 (dd, 2H), 3.88 (m, 2H), 4.14 (m, 2H), 7.38 (dd, 1 H) ppm.

Reference： [1]Patent: WO2012/7426,2012,A1 .Location in patent: Page/Page column 252

56
[ 53293-00-8 ]
[ 60-23-1 ]
[ 1270144-32-5 ]

Yield	Reaction Conditions	Operation in experiment
78.5%	Stage #1: hex-5-ynoic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: Cysteamine In N,N-dimethyl-formamide at 25℃; Inert atmosphere;
78.5%	Stage #1: hex-5-ynoic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #3: Cysteamine In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere; Cooling with ice;	7 Example 7 Under a nitrogen atmosphere, 5-hexynoic acid (1.0 g, 8.9 mmol), HBTU (3.41 g, 9.0 mmol) and HOBt (1.22 g, 9.0 mmol) were dissolved in anhydrous DMF (20 mL). The solution was stirred for 5 min in ice bath, DIPEA (1.94 g, 15 mmol) was added. The solution was stirred in ice bath for 5 min, then cysteamine (694.35 mg, 9.0 mmol) was added and the solution was stirred at room temperature overnight for 5 h. Then EtOAc (50 mL) was added and the organic solution was washed with NaHCO3 aq. (satd.) and HCl (1 M) then NaCl aq. The solution was dried (MgSO4) and removed to 15 mL by rotary evaporation. The Comp.1 was obtained by recrystallized from EtOAc in 78.5% yield. 1H NMR (300 MHz, CDCl3, δ in ppm): 1.84 (m, 2 H, CCH2CH2CH2CO), 1.95 (s, 2, CH), 2.22 (m, 2H, CCH2CH2CH2CO), 2.34 (m, 2H, CCH2CH2CH2CO), 2.82 (m, 2 H, SHCH2CH2), 3.55 (m, 2 H, SHCH2CH2), 6.46 (s, 1 H, NH). 13C NMR (75 MHz, CDCl3, δ in ppm): 172.84, 83.48, 69.17, 38.40, 37.72, 34.88, 24.13, 17.87.

Reference： [1]Location in patent: experimental part Luo, Kui; Yang, Jiyuan; Kopeckova, Pavla; Kopecek, Jindrich [Macromolecules, 2011, vol. 44, # 8, p. 2481 - 2488]
[2]Current Patent Assignee: UNIVERSITY OF UTAH - US9289510, 2016, B2 Location in patent: Page/Page column 14

57
[ 60-23-1 ]
[ 194423-15-9 ]
C₁₉H₂₀BrN₅OS [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2251 - 2264

58
[ 6136-93-2 ]
[ 60-23-1 ]
[ 90483-42-4 ]

Reference： [1]Synthetic Communications,2012,vol. 42,p. 2098 - 2109

59
[ 1003-31-2 ]
[ 60-23-1 ]
[ 60705-34-2 ]

Reference： [1]Journal of the Serbian Chemical Society,2012,vol. 77,p. 1181 - 1189,9
[2]E-Journal of Chemistry,2012,vol. 9,p. 1035 - 1041

60
[ 22161-81-5 ]
[ 60-23-1 ]
[ 1345001-47-9 ]

Reference： [1]Medicinal Chemistry Research,2012,vol. 21,p. 2280 - 2291

61
[ 892-48-8 ]
[ 60-23-1 ]
[ 38716-43-7 ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 408 - 412
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 8066 - 8074,9

62
[ 1369959-37-4 ]
[ 60-23-1 ]
[ 2896-98-2 ]
2-(10-hydroxy-3-phenylaminomethyl-3H-benzo[c]xanthen-7-yl)benzoic acid [ No CAS ]

Reference： [1]Organic and biomolecular chemistry,2012,vol. 10,p. 2739 - 2741,3

63
[ 383-63-1 ]
[ 60-23-1 ]
[ 1869-45-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine In methanol at 20℃;
65%	With triethylamine In methanol at 20℃;	Synthesis of compound 1. Cysteamine (8.0 g, 103.69 mmol, 1 equiv.) was dissolved in 100 mL of methanol in the presence oftriethylamine (15.74 g, 155.5 mmol, 1.5 equiv.). After ethyltrifluoroacetate (17.67 g, 124.42 mmol, 1.2equiv.) was added to the above mixture, and the reaction mixture was stirred overnight at RT. The residuewas extracted with 3 × 100 mL of ethyl acetate, and the combined organic layer was dried using anhydrousmagnesium sulfate. The residue was purified by silica gel column chromatography using an eluent gradientfrom hexane to 7/3 hexane/ethyl acetate to obtain the product (11.72 g, 67.65 mmol, 65 % yield). 1H NMR(300 MHz, CDCl3): δ 1.64 (s, 1H, CF3CONHCH2CH2SH); 2.91 (t, 2H, CF3CONHCH2CH2SH); 3.73 (q, 2H,CF3CONHCH2CH2SH); 6.87 (s, 1H, CF3CONHCH2CH2SH)
	With triethylamine In methanol at 20℃; for 5h;	1.1; 1.2; 1.3 1) the mercat ethylamine by adding methanol stirring, configured to concentration is 2mol/L solution, then the and mercat ethylamine mole ratio of 1:1 and mercat ethylamine mole triethylamine and a ratio of 1:1 of trifluoro acetic acid ethyl ester is added in the solution; stirring at room temperature 5h; 2) the 1) of the reaction is completed in the mixed solution with 300 ml of ethyl acetate to hours, 3 times, each time 100 ml for extraction; obtained organic phase of ethyl acetate; organic phase is then added to anhydrous magnesium sulfate until there is no bubble generating, full water removal, filtering to obtain a liquid; 3) will 2) the liquid in the separation and purification by silica gel column chromatography to obtain intermediate product, wherein silica gel column using n-hexane and ethyl acetate as an eluting agent mixture, the volume ratio of 1:4

Reference： [1]Shim, Min Suk; Xia, Younan [Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 6926 - 6929][Angew. Chem., 2013, vol. 125, # 27, p. 7064 - 7067,4]
[2]Wang, Yueqi; Li, Changjian; Du, Libo; Liu, Yang [Chinese Chemical Letters, 2020, vol. 31, # 1, p. 275 - 280]
[3]Current Patent Assignee: TIANJIN UNIVERSITY - CN105523976, 2016, A Location in patent: Paragraph 0028; 0029; 0030; 0031

64
[ 156-57-0 ]
[ 60-23-1 ]
[ 67881-98-5 ]
2'-[3-(2-aminoethylsulfanyl)-2-methylpropionyloxy]ethyl-[2-(trimethylammonio)ethyl]phosphate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 25℃; for 3h; Inert atmosphere;	1-1 Synthesis of 2'-[3-(2-aminoethylsulfanil)-2-methylpropionyloxy]ethyl-[2-(trimethylammonio)ethyl]phosphate hydrochloride (AmPC) Example 1-1 Synthesis of 2'-[3-(2-aminoethylsulfanil)-2-methylpropionyloxy]ethyl-[2-(trimethylammonio)ethyl]phosphate hydrochloride (AmPC) 2.00 g (6.77 mmol) of MPC was placed in a three-neck flask, to which 11.33 g of ethanol was added and stirred into a homogeneous mixture. The mixture was bubbled with nitrogen gas to establish a nitrogen atmosphere in the flask, to which 0.80 g (7.08 mmol) of 2-aminoethanethiol hydrochloride was added, and dissolved into a homogeneous mixture. Then 0.03 g (0.37 mmol) of 2-aminoethanethiol was added, and stirred at room temperature for 3 hours to react. To the obtained reaction solution was added 11.33 g of acetonitrile, and the solvent was removed by azeotropic distillation under reduced pressure, to thereby obtain a white solid product. The obtained white solid product was subjected to 1H-NMR analysis, 13C-NMR analysis, IR analysis, and mass spectrometry. The results are shown in and below. The results demonstrated that the obtained white solid product was the objective compound AmPC represented by formula (1).

Reference： [1]Current Patent Assignee: NOF CORPORATION - US2013/310591, 2013, A1 Location in patent: Paragraph 0050-0059

65
[ 60-23-1 ]
[ 67881-98-5 ]
2'-[3-(2-aminoethylsulfanyl)-2-methylpropionyloxy]ethyl-[2-(trimethylammonio)ethyl]phosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 25℃; for 6h; Inert atmosphere;	1-7 Examples 1-5 to 1-8 A product was obtained through the reaction, analyzed, and measured in the same way as in Example 1-1 except that the charging ratio of the starting materials and the conditions were changed as shown in Table 3. As a catalyst, diisopropylamine and triethylamine were used in Examples 1-5 and 1-6, respectively. The results are shown in Table 3. As a result of the analyses, the main products obtained in Examples 1-7 and 1-8 were both 2′-[3 (2-aminoethylsulfanil)-2-methylpropionyloxy]ethyl-[2-trimethylammonio]ethyl]phosphate.

Reference： [1]Current Patent Assignee: NOF CORPORATION - US2013/310591, 2013, A1 Location in patent: Paragraph 0060

66
[ 625-51-4 ]
[ 60-23-1 ]
[ 95501-85-2 ]

Yield	Reaction Conditions	Operation in experiment
	In trifluoroacetic acid; at 20℃; for 3h;	The mixture of cysteamine (1.15 g) and <strong>[625-51-4]acetamidemethanol</strong> (1 g) weredissolved in TF A ( triflouroacetic acid), and were stirred at room temperature for 3 hours toyield (S-acetamidomethyl) cysteamine 7 with molecular weight of 148 Da; while the found(M+H) ion peak is 149 Da.

Reference： [1]Patent: WO2013/142298,2013,A1 .Location in patent: Page/Page column 41

67
[ 86215-57-8 ]
[ 60-23-1 ]
2-(3-methoxyphenyl)-3-thiomorpholinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		In a 500 mL round-bottomed flask, methyl2-bromo-2-(3-methoxyphenyl)acetate (5.2 g,20.1 mmol), 2-aminoethanethiol (1.55 g, 20.1 mmol) and potassium carbonate (5.55 g, 40.1mmol) were combined with ethanol (150 ml) to give a light yellow suspension. The resultantmixture was stirred at 85 oc (bath temp.) for 2.5 h. No starting material remained. Theintermediate, [2-amino-1-(3-methoxy-phenyl)-ethylsulfanyl]-acetic acid methyl ester, was themajor product with 25% of the cyclized product. The mixture was further heated at reflux for anadditional4.5h. Complete by LCMS. Reaction mixture was allowed to cool to roomtemperature and sit overnight. The reaction mixture was poured into 500 mL H20 and extractedwith EtOAc (3 x 300 mL ). The combined organic layers were washed with brine, dried overMgS04 and concentrated in vacuo. The resulting pale yellow solid was triturated with cold etherand dried under vacuum to afford 2-(3-methoxyphenyl)thiomorpholin-3-one (3.7 g, 83%) as ayellow solid. (M+Ht =224m/e. 1H NMR (400 MHz, CHLOROFORM-d) 8 ppm 2.88 (td,J=5.81, 2.78 Hz, 2 H) 3.67 (td, J=5.81, 3.54 Hz, 2 H) 3.82 (s, 3 H) 4.63 (s, 1 H) 6.42 (br. s., 1 H)6.85 (ddd, J=8.34, 2.53, 0.76 Hz, 1 H) 7.00 (t, J=2.15 Hz, 1 H) 7.01-7.05 (m, 1 H) 7.29 (t,J=7.93, 1 H).

Reference： [1]Patent: WO2014/56958,2014,A1 .Location in patent: Paragraph 0115

68
[ 76-84-6 ]
[ 60-23-1 ]
[ 1095-85-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With trifluoroacetic acid at 20℃;	2-(Tritylthio)ethanamine (4): Triphenylmethyl (3, Trt, 2.29 g, 8.8 mmol) was added to a solution of 2-mercaptoethylamine (1.0 g, 8.8 mmol) in trifluoroacetate (TFA, 10 mL) in room temperature. The mixture was reacted for 1 h and turned to red. Then, it was poured into water (40 mL), extracted with ethyl acetate (EA, 3 × 20 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated. A white precipitate was filtered and recrystallized from EA to produce 4 (white solid, 90% yield, mp 93-95 °C). ESI-MS m/z 320.2 [M + H]+; 1H-NMR (400MHz, CDCl3) δ 7.74 (brs, 2H, -NH2), 7.41 (d, 5H, ArH, J = 7.3 Hz), 7.27 (m, 6H, ArH), 7.22-7.17 (m, 4H,ArH), 2.59 (t, 2H, -CH2CH2S-, J = 6.6 Hz), 2.26-2.19 (m, 2H, NH2CH2CH2-).
90%	With trifluoroacetic acid at 20℃;	2 Example 2: Synthesis of sorafenib mercapto derivatives Synthesize sorafenib mercapto derivatives according to Scheme1: 1) Dissolve 2-aminoethanethiol (1.0g, 8.8mmol) in 10mL trifluoroacetic acid, add trityl alcohol (2.29g, 8.8mmol),Reaction at room temperature, the reaction solution was dark red. After the reaction is complete,Add a small amount of ethyl acetate, rotate and evaporate to semi-dry,Extract with ethyl acetate, rinse with 1N sodium hydroxide solution three times, and rinse with saturated saline three times. A white solid precipitated out,Suction filtration, drying, to obtain compound A (90%, white solid).
86%	With trifluoroacetic acid at 20℃; for 3h; Inert atmosphere;	3 4.3. S-Tritylaminoethanethiol (21) Aminoethanethiol (2.32 g, 30 mmol) was dissolved in 50 mL of TFA. Triphenylcarbinol (7.81 g, 30 mmol) was added to the solution portionwise, under stirring at room temperature, until the solution became clear. The reaction mixture, a dense deeply red liquid, was stirred for 3 h and then distilled to remove the solvent under reduce pressure. The residue was dissolved in a mixture of DCM and 3.0 M NaOH aqueous solution, and then the organic layer was isolated, washed with water and brine, and dried with MgSO4. After filtration and evaporation, the residue was chromatographed on silicagel with DCM/MeOH (15/1) as the eluent, yielding yellowish solid (8.21 g, 86%). Mp 91-93 C,21 1H NMR (400 MHz, CDCl3):d 7.18e7.47 (m, 15H, ArH), 2.58 (t, J 6.4 Hz, 2H, NCH2CH2), 2.32 (t,J 6.4 Hz, 2H, SCH2CH2), 1.08 (brs, 2H, NH2), ESI-MS m/z 320.2[MH].

62.7%	With chloro-trimethyl-silane; acetic acid at 60℃; for 6h;	6.6.3 6.3. Add 100g (1.3mol) of 2-mercaptoethylamine to glacial acetic acid and heat up, then add 423g (1.625mol) of trityl alcohol, then slowly add 155.3g (1.43mol) of trimethylchlorosilane, and heat up under mechanical stirring React at 60°C for 6 hours, then cool to about 5°C, adjust the pH of the system with 20% by mass sodium acetate aqueous solution and stir for crystallization, then filter the system, and rinse the filter cake with water and ether to obtain S-triphenyl Methylcysteamine, dried to obtain 259.7g (62.7%, 1.09mol).
	With trifluoroacetic acid at 20℃; for 3h;	Cysteamine (commercial) (900 mg, 11.67 mmol) was added to a stirred solution of triphenylmethanol (commercial) (3.037 g, 11.67 mmol) in TFA (10 ml) and the mixture stirred at RT for 3 hours. The mixture was then concentrated under reduced pressure and the residue partitioned between DCM (20 mL) and water (20 mL). The mixture was basified by the slow addition of solid K2CO3. The aqueous phase was extracted with DCM (2×20 mL), the combined organic phases passed through a hydrophobic frit and the solvent evaporated under reduced pressure. The material was used without further purification.

Reference： [1]Chen, Ying; Kuerbana, Kudelaidi; Wan, Qi; Wang, Ke; Ye, Li; Yu, Zhihui [Molecules, 2020, vol. 25, # 3]
[2]Current Patent Assignee: FUDAN UNIVERSITY - CN112624967, 2021, A Location in patent: Paragraph 0010; 0022-0223
[3]Yu, Xiaoling; Zhang, Bingbing; Shan, Guangsheng; Wu, Yue; Yang, Feng-Ling; Lei, Xinsheng [Tetrahedron, 2018, vol. 74, # 5, p. 549 - 555]
[4]Current Patent Assignee: GL BIOCHEM SHANGHAI - CN111704566, 2020, A Location in patent: Paragraph 0051; 0053; 0066
[5]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US2014/171417, 2014, A1 Location in patent: Paragraph 1764

69
[ 1229114-49-1 ]
[ 60-23-1 ]
C₂₃H₃₁NO₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	Compound 1 General procedure: First, 50 mg (0.13 mmol) of xyloketal B acid [16] and 22 mg (0.20 mmol) of p-fluoroaniline were dissolved in 10 mL of DMF in a 50 mL-round-bottom flask. Then, 80 mg (0.20 mmol) of BOP and 0.40 mL (2.0 mmol) of DIEA were added and stirred at room temperature overnight. The reaction was quenched with 10 mL saturated solution of ammonium chloride in ice water. The aqueous layer was extracted with ethyl acetate, 3 × 25 mL. The combined organic extracts were washed with saturated ammonium chloride and brine, dried over anhydrous MgSO4 and concentrated in vacuo. Purification by flash chromatography (petroleum ether: ethyl acetate = 5:1~2:1) gave the title compound.

Reference： [1]Liu, Shixin; Luo, Rong; Xiang, Qi; Xu, Xianfang; Qiu, Liqin; Pang, Jiyan [Marine Drugs, 2015, vol. 13, # 2, p. 948 - 973]

70
[ 42872-74-2 ]
[ 60-23-1 ]
C₁₀H₁₀BrNS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 90℃; for 1h;	Step 1 : A solution of <strong>[42872-74-2]3-bromo-4-methylbenzonitrile</strong> (1.96 g, 10 mmol) and 2-aminoethanethiol (1.0 g, 13 mmol) in EtOH (30 mL) was heated to 90C for 1 h. The mixture was chilled, diluted with Et20 (250 mL) and was washed with water. The organic layer was dried and the volatiles were removed under reduced pressure to yield the desired compound of step 1. LC-MS (method 1): m/z: [M+H]+ = 257.1 (MW calc. = 256.16), R, = 3.8 min.

Reference： [1]Patent: WO2015/22073,2015,A1 .Location in patent: Page/Page column 58

71
[ 10602-00-3 ]
[ 60-23-1 ]
4-ethynyl-N-(2-mercaptoethyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 16h;	To a solution of 2 (470 mg,3.22 mmol) in DMF (18.0 mL) were added cysteamine 3 (1.10 g, 9.68 mmol), PyBOP (1.83 g,3.52 mmol), and triethylamine (3.25 g, 32.2 mmol) at 0 C. The reaction mixture was stirred for 16 h at room temperature. The mixture was diluted with Et2O and washed with 1N HCl, sat.NaHCO3, 1N HCl again, and brine, and dried over Na2SO4. Filtration followed by concentrationin vacuo gave 116 mg (18%) of 1 as a yellow solid, which was recrystallized from AcOEt to give 41 mg of 1 as a green crystal: mp 179-181 C; 1H NMR (DMSO-d6, 300 MHz, delta; ppm)8.80 (1H, t, J = 5.5 Hz), 7.90 (2H, d, J = 8.6 Hz), 7.63 (2H, d, J = 8.4 Hz), 4.43 (1H, s), 3.65-3.59 (2H, m), 2.99 (2H, t, J = 6.9 Hz), 1.30 (1H, s); 13C NMR (DMSO-d6, 75 MHz, delta; ppm)165.47, 161.82, 134.30, 131.62, 127.42, 124.43, 82.83, 82.78, 37.02.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2645 - 2649

72
[ 68181-17-9 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
Fmoc-L-Arg(Pbf)-OH [ No CAS ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 109425-51-6 ]
[ 150629-67-7 ]
[ 60-23-1 ]
[ 59-05-2 ]
YPS-[N^ε-(3-[(2-(MTX)ethyl)disulfanyl]propanoyl)K]PDFPGEDAPAEDLARYYSALRHYINLITRPRY [ No CAS ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 804 - 814

73
[ 105-39-5 ]
[ 60-23-1 ]
[ 20196-21-8 ]

Yield	Reaction Conditions	Operation in experiment
18%	With potassium carbonate; In ethanol; at 20 - 75℃; for 26h;	To a solution of 2-aminoehtane-1-thiol (4.5 g, 40 mmol, 1.0 equiv) and K2CO3 (5.5 g, 40 mmol, 1.0 equiv.) in EtOH (80 mL) was added ethyl chloroacetate (40 mmol, 1 equiv). The resulting solution was stirred at room temperature for 2 h and at 75 C for 24 h. After filtration, all volatiles were removed in vacuo. The crude product was purified by flash column chromatography (SiO2, EtOAc) to give thiomorpholin-3-one as white solid in 18% yield.

Reference： [1]Tetrahedron,2015,vol. 71,p. 6349 - 6353

74
[ 571-60-8 ]
[ 60-23-1 ]
[ 33421-62-4 ]

Yield	Reaction Conditions	Operation in experiment
34%	With Trametes villosa laccase; oxygen In methanol at 22℃; for 12h; Enzymatic reaction;	3,4-Dihydro-2H-naphtho[2,3-b][1,4]thiazine-5,10-dione 192.9 mg (2.50 mmol) of cysteamine (8) was added to a 50mL round-bottom flask equipped with a stir bar. 8.5 mL 0.10 M sodium acetate buffer pH 5.0 was added followed by 33.1 μL (50U) of laccase solution and the mixture was stirred. Then, 80.1 mg (0.50 mmol) of 2a was dissolved in 1.5 mL MeOH and added dropwise to the mixture. The reaction mixture was allowed to stirat rt for 12 h. The precipitate was then filtered, washed with deionized water, and left to dry in a fume hood overnight. The product was purified via preparative layer chromatography using silica gel coated on glass plates as the stationary phase and dichloromethane containing 1% MeOH (v:v) as the mobile phase.Yield of 9: 39.3 mg (34%).

Reference： [1]Cannatelli, Mark D.; Ragauskas, Arthur J. [Tetrahedron Letters, 2016, vol. 57, # 33, p. 3749 - 3753]

75
kandelin B-5 [ No CAS ]
[ 60-23-1 ]
4β-(2-aminoethylthio)cinchonain Ib [ No CAS ]
4-β-(2-aminoethylthio)catechin [ No CAS ]
[ 154-23-4 ]

Yield	Reaction Conditions	Operation in experiment
0.9 mg; 0.6 mg; 0.4 mg	With hydrogenchloride; In water; at 80℃; for 2h;	A mixture of compound 1 (8 mg), cysteamine (20 mg), and 1 M aqueous hydrochloric acid (3 mL)was refluxed for 2 h with stirring. After removal of the solvent by evaporation under reduced pressure,the oily residue was applied to a Sephadex LH-20 column (DCM/MeOH, 1:1), and was further purifiedby semi-preparative HPLC (gradient model, MeOH/H2O, 10-90% over 30 min) to afford: 1a (0.9 mg),1b (0.6 mg), and 1c (0.4 mg).4beta-(2-aminoethylthio)-cinchonain Ib (1a): Amorphous powder, [alpha]25D = 41.8 (c = 0.09, MeOH); 1H-NMR(400 MHz, Acetone-d6): delta 6.91 (1H, d, J = 1.9 Hz, H-2'), 6.74 (2H, s, H-5', 6'), 6.71 (2H, m, H-2'', 5''),6.53 (1H, dd, J = 2.0, 8.1 Hz, H-6''), 6.23 (1H, s, H-6), 5.27 (1H, br.s, H-2), 4.45 (1H, m, H-7''), 4.17 (1H,br.s, H-4), 4.12 (1H, br.s, H-3), 3.07 (1H, dd, J = 6.9, 15.9 Hz, H-8''a), 2.90 (1H, br.d, J = 15.9 Hz, H-8''b),3.80-2.80 (4H, m, S-CH2-CH2-N); (-)-ESIMS: m/z 526 [M - H]-.4beta-(2-aminoethylthio)-catechin (1b): Amorphous powder, [alpha]25D = 33.2 (c = 0.06, MeOH); 1H-NMR(400 MHz, Acetone-d6): delta 6.91 (1H, d, J = 1.9 Hz, H-2), 6.75 (1H, d, J = 8.1 Hz, H-5'), 6.70 (1H, dd,J = 1.9, 8.1 Hz, H-6'), 5.91 (2H, s, H-6, 8), 5.31 (1H, d, J = 9.3 Hz, H-2), 4.00 (1H, m, H-3), 3.88 (1H, d,J = 6.6 Hz, H-4), 3.60-2.40 (4H, m, S-CH2-CH2-N).catechin (1c): Amorphous powder; 1H-NMR (400 MHz, Acetone-d6): delta 6.91 (1H, d, J = 1.9 Hz, H-2'),6.81 (1H, d, J = 8.1 Hz, H-5'), 6.77 (1H, dd, J = 1.9, 8.1 Hz, H-6'), 6.04 (1H, d, J = 1.9 Hz, H-8), 5.89 (1H,d, J = 1.9 Hz, H-6), 4.57 (1H, d, J = 7.8 Hz, H-2), 4.00 (1H, m, H-3), 2.93 (1H, dd, J = 5.5, 16.0 Hz, H-4a),2.90 (1H, dd, J = 8.4, 16.0 Hz, H-4b).

Reference： [1]Molecules,2017,vol. 22

76
[ 4813-57-4 ]
[ 60-23-1 ]
C₂₃H₄₇NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 20℃; for 12h; Inert atmosphere;	12 Example 12 Synthesis of AE-AC-SA AC-SA (162 mg, 0.5 mmo 1) was weighed into a 100 mL flask and 15 mL of absolute ethanol was added and dissolved by heating.Weigh AE (116mg, 1.5mmo 1) into the AC-SA solution, extract the reaction system of air, charge N2 protection, room temperature magnetic stirringMix the reaction for 12h. The ethanol was removed by vacuum rotation and the product was recrystallized using distilled water to give the product AE-AC-SA.

Reference： [1]Current Patent Assignee: SHENYANG PHARMACEUTICAL UNIVERSITY - CN106188169, 2016, A Location in patent: Paragraph 0176; 0177; 0178; 0179; 0180

77
[ 120225-54-9 ]
[ 60-23-1 ]
C₂₅H₃₄N₈O₅S [ No CAS ]

Reference： [1]Theranostics,2017,vol. 7,p. 884 - 898

78
C₈₄H₁₃₀N₁₅O₁₅PolS₃ [ No CAS ]
BHQ-2 carboxylic acid [ No CAS ]
[ 75286-49-6 ]
[ 60-23-1 ]
[ 162558-25-0 ]
5-carboxy-2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)benzoate [ No CAS ]
C₁₀₅H₁₄₅N₂₅O₁₇S₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 9455 - 9458

79
[ 407-41-0 ]
[ 60-23-1 ]
[ 2936-69-8 ]

Reference： [1]Chemistry Letters,2017,vol. 46,p. 1789 - 1792

80
[ 5632-15-5 ]
[ 60-23-1 ]
[ 106670-43-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium ethanolate; In ethanol; at 20℃; for 5h;	A mixture of <strong>[5632-15-5]2-(bromomethyl) quinoline</strong>(1.3 g, 7.55 mmol) and2-amino-ethanethiol (581 mg, 7.55 mmol) in dry ethanol (10 mL),was added to a in-situ solution of sodium ethanolate, prepared bymixing sodium (166.42 mg, 7.23 mmol) to dry ethanol (15 mL)under nitrogen. The mixture was stirred for 5 h at roomtemperature. After completion of the reaction as monitored byTLC, the mixture was neutralized and extracted with ethyl acetate.The crude product was isolated byflash chromatography on silicagel using MeOH/DCM (1:9, v/v) to get yellow liquid, assigned as 2with 65% yield (824 mg,). The liquid was characterized by 1H NMR(Figure S-3) (300 MHz, CDCl3): d = 1.521 (2H, s), 2.265 (2H, t), 2.505(2H, t), 3.665 (2H, s), 7.163 (2H, m), 7.361 (2H, m), 7.742 (2H, m). 13CNMR (Figure S-4) (75 MHz, CDCl3): d 158.49, 146.91, 136.51, 129.23,128.89, 128.44, 127.17, 127.10, 127.03, 126.63, 126.56, 126.49, 126.43,125.92, 121.50, 120.76, 39.86, 37.81, 30.44.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2018,vol. 360,p. 26 - 33

81
[ 1353016-71-3 ]
[ 60-23-1 ]
C₂₁H₂₀N₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 20℃; for 4h;	In the same manner, 2-mercaptoethylamine (5.0 mg, 0.07 mmol) and cyclooctyne compound <strong>[1353016-71-3]DBCO-NHS</strong> (35 mg, 0.07 mmol) were dissolved in 200 μL of DMF to give compound 10,5 mL of AuNS 8 (1.0 μM) in an aqueous solution was added dropwise, and the reaction was stirred at room temperature overnight, and the product was purified by dialysis to give AuNS 11 . AuNS 11 (5.0 nmol),The mixture of compound 3 and 3a (1:99 molar ratio, totally 0.03 mmol) was dissolved in 5.0 mL of deionized water, and the reaction was stirred overnight at room temperature, and the product was dialyzed and purified to obtain a nanoprobe Au-AK.

Reference： [1]Patent: CN107837403,2018,A .Location in patent: Paragraph 0018; 0027; 0029

82
[ 60-23-1 ]
[ 26364-65-8 ]
(Z)-N-(thiazolidin-2-ylidene)-4,5-dihydrothiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16 g	With triethylamine; In methanol; at 20℃; for 4h;Inert atmosphere;	Under nitrogen protection, add 25g (0.197mol) HRB-1365-2 to the three-necked bottle.(<strong>[26364-65-8]2-cyanoimino-1,3-thiazolidine</strong> molecular formula: C4H5N3S) compound, adding 300 mL of methanol,With stirring, 23 g of triethylamine was added, and 26 g (0.230 mol) was added.Compound HRB-1365-1 (Cysteamine molecular formula:C2H7NS), stir the reaction at room temperature for four hours,After LC-MS was monitored, the methanol was distilled off under reduced pressure and the solid was filtered.The solid distilled water was washed with 50 ml, and dried to obtain a white solid HRB-1365 (amino thiol thiazoline molecular formula: C6H9N3S2) 16 g,

Reference： [1]Patent: CN103387550,2016,B .Location in patent: Paragraph 0053; 0054; 0061

83
[ 104987-11-3 ]
[ 60-23-1 ]
C₄₆H₇₆N₂O₁₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With 2,2-dimethoxy-2-phenylacetophenone; In methanol; for 0.25h;UV-irradiation;	<strong>[104987-11-3]Tacrolimus</strong> (201.0 mg, 0.25 mmol), Boc-cysteamine (46.0 mg, 0.26 mmol), DPAP (3.2 mg, 12.5 nmol) and 0.4 mL dichloromethane were put in a vials, and stirred 15 minutes under UV light. White solid (246 mg, 98% yield) was obtained after purification by silica gel column chromatography using ethyl acetate as an eluting solvent (Rf=0.5). 1H NMR (300 MHz, CDCl3): 5.33-5.21(d, J=36.8 Hz, 1H), 5.12-5.08 (m, 2H), 4.88-4.40 (m, 1H), 3.94-3.57 (m, 3H), 3.41-3.29 (m, 9H), 3.05-2.95 (m, 2H), 2.78-2.50 (m, 6H), 2.38-1.26 (m, 45H), 1.07-0.82(m, 13H). TOF-HRMS (m/z) found (calcd.) for C51H84N2O14S (M): [M+Na]+, 1003.5583 (1003.5541).

Reference： [1]Patent: US10093929,2018,B2 .Location in patent: Page/Page column 24

84
[ 1214891-99-2 ]
C₈₄H₁₃₁N₁₆O₁₅PolS₃ [ No CAS ]
[ 75286-49-6 ]
[ 60-23-1 ]
[ 162558-25-0 ]
5-carboxy-2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)benzoate [ No CAS ]
C₁₀₃H₁₄₃N₂₇O₁₇S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		50 muetaetaomicronIota of NH2-Fx-r-Fx-r-Fx-r on resin was reacted with Fmoc-Np-Boc-L-2,3- diaminopropionic acid (4 eq, ChemPep Inc.), HBTU (4 eq), and DIPEA (8 eq) in 1 mL N,N- dimethyl formamide (DMF) for 2 hours at room temperature. The peptide was washed (2 x DMF/MeOH/DCM), cleaved from resin using trifluoroacetic acid:triisopropylsilane:water (0132) (95:2.5:2.5) and precipitated in ether at -20°C for 1 hour. The precipitate was purified by RP- HPLC, lyophilized, and reacted with S-trityl-2-mercaptoproprionic acid (4 eq), PyBOP (4 eq), and DIPEA (8 eq) in 0.5 mL DMF. The peptide was re-precipitated in ether and then dried under vacuum for 1 hour. The peptide was deprotected using 0.5 mL trifluoroacetic (0133) acid:triisopropylsilane:DCM (5:3:92, 15 minutes), precipitated in ether, and purified by HPLC. The peptide was dried under vacuum and dissolved in 0.5 mL acetonitrile:water (5: 1). (0134) Cysteamine (20 eq) was added to the reaction mixture followed by iodine (10 eq) and the reaction was stirred for 30 minutes. The reaction mixture was precipitated in ether, and purified by HPLC. The peptide was lyophilized and reacted with BHQ-2 carboxylic acid (2 eq), PyBOP (2 eq), and DIPEA (4 eq) overnight in 0.5 mL DMF. The peptide was precipitated in ether, dried, and deprotected in 1 mL 20percent piperidine in DMF for 20 minutes. The peptide was purified by HPLC, lyophilized, and reacted with 5-Carboxytetramethylrhodamine (2 eq), HBTU (2 eq), and DIPEA (4 eq) in 0.5 ml_ DMF for 2 hours. The peptide was precipitated in ether and purified by HPLC. The peptide was identified by ESI mass spectrometry, expected m/z = 2094.07, found m/z = 2094.07.

Reference： [1]Patent: WO2018/232491,2018,A1 .Location in patent: Paragraph 0075

85
[ 3582-05-6 ]
[ 60-23-1 ]
[ 2682-49-7 ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 10907 - 10912

86
[ 42074-68-0 ]
[ 60-23-1 ]
C₂₁H₂₀ClNS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane;	General procedure: Cysteamine or aminothiols derived from optically active amino acids (1 mol) [34] were dissolvedin the highest possible concentration in dichloromethane (DCM), and diisopropyletheylamine (DIPEA)(2.5 mol) was added. A 1 M solution (with respect to the aminothiol) of trityl chloride (1.2 mol) or4-methoxytrityl chloride (1.2 mol) in DCM was prepared. This was added dropwise to the stirredaminothiol solution. The completion of the reaction was checked by TLC. The DCM was removed byrotary evaporation and diethylether (DEE) was added to the residual oil. The precipitated solid wasfiltered, washed with DEE, and dried in vacuo.

Reference： [1]Molecules,2019,vol. 24

87
[ 60-23-1 ]
[ 67-64-1 ]
[ 22907-30-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride; In water; at 20℃; for 8.0h;	First, add 5.68g (50mmol) of mercaptoethylamine and 7.80g (135mmol) of anhydrous acetone to a 100ml eggplant-shaped bottle, pass saturated hydrogen chloride gas, stir the reaction at room temperature for 8h, and precipitate a white solid product. After filtration, use chloroform Wash twice. The crude product was then dried and recrystallized three times to obtain 4.21 g of product, with a yield of 86%.

Reference： [1]Patent: CN110974806,2020,A .Location in patent: Paragraph 0040-0044

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2-Aminoethanethiol (2R,3R)-2,3-dihydroxysuccinate

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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 60-23-1 ] Synthesis Path-Upstream 1~14

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