[ CAS No. 32047-53-3 ] {[proInfo.proName]}

Name: 32047-53-3|1-Amino-2-methylpropane-2-thiol hydrochloride|98%
Brand: Ambeed
SKU: A158497
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Quality Control of [ 32047-53-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 32047-53-3 ]

Product Details of [ 32047-53-3 ]

CAS No. :	32047-53-3	MDL No. :	MFCD00191744
Formula :	C₄H₁₂ClNS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YZCAFAKJYGDMSY-UHFFFAOYSA-N
M.W :	141.66	Pubchem ID :	13049104
Synonyms :

Calculated chemistry of [ 32047-53-3 ]

Physicochemical Properties

Num. heavy atoms :	7
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 :	38.98
TPSA :	64.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.99
Log Po/w (WLOGP) :	1.46
Log Po/w (MLOGP) :	1.16
Log Po/w (SILICOS-IT) :	0.18
Consensus Log Po/w :	0.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.28
Solubility :	7.5 mg/ml ; 0.053 mol/l
Class :	Very soluble
Log S (Ali) :	-1.94
Solubility :	1.63 mg/ml ; 0.0115 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.79
Solubility :	23.0 mg/ml ; 0.163 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.07

Safety of [ 32047-53-3 ]

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:

Application In Synthesis of [ 32047-53-3 ]

* 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.

Downstream synthetic route of [ 32047-53-3 ]

[ 32047-53-3 ] Synthesis Path-Downstream 1~44

1
[ 32047-53-3 ]
[ 2051-95-8 ]
[ 2952-85-4 ]

Reference： [1]Journal of Organic Chemistry,1965,vol. 30,p. 1506 - 1508

2
[ 32047-53-3 ]
[ 1501-05-9 ]
[ 3037-05-6 ]

Reference： [1]Journal of Organic Chemistry,1965,vol. 30,p. 1506 - 1508

3
[ 32047-53-3 ]
[ 119-67-5 ]
[ 3063-82-9 ]

Reference： [1]Journal of Organic Chemistry,1965,vol. 30,p. 1506 - 1508

4
[ 32047-53-3 ]
2-Methyl-2-(nitrosothio)propylamine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With tert.-butylnitrite; In hexane; dichloromethane; N,N-dimethyl-formamide;	38a. 2-Methyl-2-(nitrosothio)propylamine hydrochloride To <strong>[32047-53-3]1-amino-2-methylpropane-2-thiol hydrochloride</strong> (5.39 g, 38 mmol) in N,N-dimethylformamide (16 mL) in a salt-ice bath (-10 C. to -20 C.) was slowly added tert-butyl nitrite (4.8 mL, 4.16 g, 40.4 mmol) and the resultant solution was stirred in the salt-ice bath for 30 minutes. Dichloromethane (30 mL) was added and then hexane (250 mL) to give crystals. Under argon, the crystals were collected by filtration and washed with dichloromethane. The product was dried in vacuum to give the title compound (1.69 g, 15%). 1H NMR (D2O) delta3.88 (s, 2H), 1.95 (s, 6H). 13C NMR (DMSO-d6) delta54.7, 48.5, 26.5. LRMS (APIMS) m/z 135 (MH+).

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 7019 - 7026
[2]Patent: US2003/203915,2003,A1

5
[ 32047-53-3 ]
[ 108-24-7 ]
N-Acetyl-1-amino-2-methylpropane-2-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water; at 20℃; for 1.83333h;pH 8.0;	To a stirred solution of cysteamine hydrochloride (2.00 g, 14.1 mmol) in 15 mL of water was added acetic anhydride (4.30 g, 42.4 mmol) and aqueous KOH (8 M, to maintain pH=8) dropwise. The mixture was then neutralized by adding 2N HCI and stirred for 1 hour at room temperature. To the solution cooled with an ice bath was added slowly solid KOH (2.80 g, 49.4 mmol) and the mixture was stirred for 50 minutes at room temperature. After saturated with NaCI and neutralized with 6N HCI, the mixture was extracted with CH2CI2 twice. The combined CH2CI2 extracts were dried (Na2S04) and concentrated in vacuo to yield N-(2-mercapto-2-methylpropyl)acetamide as a white solid which was used for next step without further purification.

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 7019 - 7026
[2]Patent: WO2015/155231,2015,A1 .Location in patent: Page/Page column 69

6
[ 32047-53-3 ]
[ 74637-14-2 ]
[ 190251-55-9 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1997,p. 1403 - 1410

7
[ 32047-53-3 ]
[ 190251-44-6 ]
[ 190251-59-3 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1997,p. 1403 - 1410

8
[ 32047-53-3 ]
[ 190251-46-8 ]
[ 190251-63-9 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1997,p. 1403 - 1410

9
[ 7310-95-4 ]
[ 32047-53-3 ]
bis(iminomethyl)-2,6-bis(mercaptoisobutyl)-4-methylphenol [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2001,p. 751 - 754

10
[ 32047-53-3 ]
[ 5659-93-8 ]
[ 354115-65-4 ]

Reference： [1]Synthetic Communications,2001,vol. 31,p. 1323 - 1333

11
[ 2645-22-9 ]
[ 32047-53-3 ]
1-amino-2-methyl-2-propyl 4-pyridyl disulfide dihydrochliride [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 4666 - 4677

12
[ 2127-10-8 ]
[ 32047-53-3 ]
3-amino-2-methyl-2-propyl 5-nitro-2-pyridyl disulfide dihydrochloride [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 4666 - 4677

13
[ 4055-39-4 ]
[ 32047-53-3 ]
7-N,7'-N'-bis-[2-(2-methylpropyl)]mitomycin C disulfide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 4666 - 4677

14
[ 85-44-9 ]
[ 32047-53-3 ]
[ 618112-95-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine; In dichloromethane;	41 a. 2-(N-(2-Methyl-2-sulfanylpropyl)carbamoyl)benzoic acid To a suspension of <strong>[32047-53-3]1-amino-2-methylpropane-2-thiol hydrochloride</strong> (4.00 g, 28.23 mmol) in dichloromethane (50 mL) at 0 C. was added triethylamine (3.14 g, 31.1 mmol) and phthalic anhydride (4.10 g, 27.7 mmol). The reaction mixture was stirred at room temperature for 1 hour and washed with 2 N hydrochloric acid. The organic phase was concentrated and the product was dried in vacuum to give the title compound (6.36 g, 91%). 1H NMR (300 MHz, DMSO-d6) delta10.2 (br s, 11H), 8.44 (t, J=6.2 Hz, 1H), 7.77-7.75 (m, 1H), 7.60-7.47 (m, 2H), 7.44-7.41 (m, 1H), 3.36 (d, J=6.1 Hz, 2H), 2.83 (s, 1H), 1.33 (s, 6H). 13C NMR (75 MHz, DMSO-d6) delta168.9, 167.9, 138.7, 131.2, 130.5, 129.14, 129.10, 127.9, 52.2, 45.0, 29.8. LRMS (APIMS) m/z 254 (MH+).

Reference： [1]Patent: US2003/203915,2003,A1

15
[ 830-79-5 ]
[ 61040-78-6 ]
[ 32047-53-3 ]
[ 618112-43-9 ]

Yield	Reaction Conditions	Operation in experiment
37%	With trifluoroacetic acid; In methanol; hexane; dichloromethane;	20a. 2-Methyl-2((2,4,6-trimethoxyphenyl)methylthio)propylamine. A suspension of 2-mercapto-2-methyl-1-propylamine hydrochloride (5.6 g, 40 mmol) in dichloromethane (200 mL) was cooled to 0 C. (internal temperature) and trifluoroacetic acid (61 mL, 90 g, 0.79 mol) introduced. To this was added a solution of 2,4,6-trimethoxybenzyl alcohol (prepared from 2,4,6-trimethoxybenzaldehyde as described by Munson, et al., J. Org. Chem., 57: 3013-3018, 1992) (7.5 g, 38 mmol) in dichloromethane (50 mL) such that the temperature of the solution did not rise above 5 C. Following the addition, the solution was stirred over ice for an additional 10 minutes. The volatile material was evaporated, and the residue was diluted with ethyl acetate, washed with saturated bicarbonate solution, dried over sodium sulfate, filtered and evaporated. The residue was chromatographed (ethyl acetate:hexane 3:1 then neat ethyl acetate then ethyl acetate:methanol 4:1) to give the title compound (4 g, 37%). 1H NMR (300 MHz, CDCl3) delta6.09 (s, 2H), 3.84 (s, 6H), 3.73 (s, 3H), 3.69 (s, 2H), 2.70 (s, 2H), 1.91 (s, 2H), 1.29 (s, 6H). 13C NMR (75 MHz, CDCl3) delta160.2, 158.6, 106.8, 90.6, 55.7, 55.2, 50.9, 48.1, 26.2, 19.7. HRMS (EI) m/z C14H23NO3S requires 285.1399 found 285.1397.

Reference： [1]Patent: US2003/203915,2003,A1

16
[ 32047-53-3 ]
[ 53715-97-2 ]
4-[N-(2-Methyl-2-sulfanylpropyl)carbamoyl]butanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With triethylamine; In dichloromethane;	13a. 4-[N-(2-Methyl-2-sulfanylpropyl)carbamoyl]butanoic acid To a suspension of <strong>[32047-53-3]1-Amino-2-methylpropane-2-thiol hydrochloride</strong> (1.41 g, 10 mmol) in anhydrous dichloromethane (10 mL) was added triethylamine (1.5 mL) at 0 C. The mixture was stirred at 0 C. for 10 minutes and glutaric anhydride (1.14 g, 10 mmol) in anhydrous dichloromethane (20 mL) was added at 0 C. under argon atmosphere. The reaction mixture was stirred at 0 C. for 10 minutes and then at room temperature for 2 hours. The solvent was evaporated at reduced pressure and the residue was extracted with ethyl acetate and water. The combined ethyl acetate extracts were washed with 1 N HCl, dried over sodium sulfate and solvent was evaporated at reduced pressure to give colorless oil, which upon trituration with ethyl ether/hexane gave 1.57 g of the title compound as a colorless powder in 72% yield, mp 101-104 C.; 1H NMR (CDCl3): delta1.31 (s, 6 H), 1.94 (m, 2 H), 2.22-2.38 (m, 4 H), 3.33 (d, J=6.1 Hz, 2 H), 6.28 (s, 1 H), 9.2 (br s, 1 H; LRMS (APIMS) (m/z) 220 (M+1).
72%	With triethylamine; In dichloromethane;	13a. 4-[N-(2-Methyl-2-sulfanylpropyl)carbamoyl]butanoic Acid To a suspension of <strong>[32047-53-3]1-Amino-2-methylpropane-2-thiol hydrochloride</strong> (1.41 g, 10 mmol) in anhydrous dichloromethane (10 mL) was added triethylamine (1.5 mL) at 0 C. The mixture was stirred at 0 C. for 10 minutes and glutaric anhydride (1.14 g, 10 mmol) in anhydrous dichloromethane (20 mL) was added at 0 C. under argon atmosphere. The reaction mixture was stirred at 0 C. for 10 minutes and then at room temperature for 2 hours. The solvent was evaporated at reduced pressure and the residue was extracted with ethyl acetate and water. The combined ethyl acetate extracts were washed with 1 N HCl, dried over sodium sulfate and solvent was evaporated at reduced pressure to give colorless oil, which upon trituration with ethyl ether/hexane gave 1.57 g of the title compound as a colorless powder in 72% yield, mp 101-104 C.; 1H NMR (CDCl3): delta1.31 (s, 6H), 1.94 (m, 2H), 2.22-2.38 (m, 4H), 3.33 (d, J=6.1 Hz, 2H), 6.28 (s, 1H), 9.2 (br s, 1H; LRMS (APIMS) (m/z) 220 (M+1).
67%	With triethylamine; In hydrogenchloride; dichloromethane; ethyl acetate;	19a. 4-(N-(2-Methyl-2-sulfanylpropyl)carbamoyl)butanoic acid To a suspension of 2-mercapto-2-methyl-1-propylamine hydrochloride (11.3 g, 80 mmol) in dichloromethane (80 mL) at 0 C. was added triethylamine (12 mL, 86 mmol). The reaction mixture was stirred at 0 C. for 10 minutes, then glutaric anhydride (9.0 g, 78 mmol) was added. The reaction mixture was stirred at 0 C. for 10 minutes then at room temperature for 2 hours. The solid was removed by filtration, and the filtrate evaporated. The residue was treated with ethyl acetate and filtered again. The filtrate was washed with IN HCl, brine and dried over sodium sulfate. The residue after filtration and evaporation was triturated with ether/hexane to give the title compound (11.7 g, 67%). Mp 101-104 C. 1H NMR (300 MHz, CDCl3) delta9.35 (br s, 1H), 6.28 (br s, 1H), 3.30 (d, J=6.15 Hz, 2H), 2.28-2.38 (m, 4H), 1.90-2.00 (m,2H), 1.31 (s, 6H). LRMS (EI) m/z 220 (MH+).

Reference： [1]Patent: US2002/143007,2002,A1
[2]Patent: US6469065,2002,B1
[3]Patent: US2003/203915,2003,A1

17
[ 4744-50-7 ]
[ 32047-53-3 ]
[ 618112-39-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With triethylamine; In dichloromethane;	17a. 3-(N-(2-Methyl-2-sulfanylpropyl)carbamoyl)pyrazine-2-carboxylic acid A suspension of 2-mercapto-2-methyl-1-propylamine hydrochloride (1.14 g, 8 mmol) in dichloromethane (15 mL) was cooled to 0 C. and then treated with triethylamine (1.23 mL, 0.9 g, 8.9 mmol) followed by furano(3,4-b)pyrazine-5,7-dione (1.2 g, 8 mmol). The reaction mixture was stirred at 0 C. for 40 minutes then at room temperature for 1 hour. The solvent was removed by evaporation and the residue triturated with hexane/ether to give the title compound (1.2 g, 59%). Mp 141-144 C. 1H NMR (300 MHz, DMSO-d6) delta8.83-8.86 (m, 3H), 3.45 (d, J=6.4 Hz, 2H), 2.87 (s, 1H), 1.33 (s, 6H).

Reference： [1]Patent: US2003/203915,2003,A1

18
[ 4480-83-5 ]
[ 32047-53-3 ]
2-{(N-(2-methyl-2-sulfanylpropyl)carbamoyl)methoxy}acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With hydrogenchloride; triethylamine; In dichloromethane;	2a. 2-{(N-(2-methyl-2-sulfanylpropyl)carbamoyl)methoxy}acetic acid To an ice-cooled suspension of <strong>[32047-53-3]1-amino-2-methyl-2-propanethiol hydrochloride</strong> (4.21 g, 29.72 mmol) in methylene chloride (50 mL) was added triethylamine (4.56 mL, 32.72 mmol) followed by diglycolic anhydride (3.43 g, 29.55 mmol). The solution was stirred at room temperature for 30 min and the reaction concentrated under vacuum. Cold 2N HCl (50 mL) was added to the residue and the mixture was extracted with ethyl acetate. The combined extracts were washed with brine and dried (sodium sulfate). Evaporation and trituration with ether/hexane gave the title compound as a white solid (5.50 g, 84%). mp. 81-82 C. 1H NMR (300 MHz, CDCl3) delta 8.80 (br s, 1H), 7.48 (br s, 1H), 4.24 (s, 2H), 4.20 (s, 2H), 3.41 (d, J=6.4 Hz, 2H), 1.59 (s, 1H), 1.38 (s, 6H). 3C NMR (75 MHz, CDCl3) delta 172.8, 170.4, 70.7,68.3, 51.9, 44.9, 29.8. LRMS (APIMS) m/z 222 (MH+), 239 (M+NH4+).
84.2%	With hydrogenchloride; triethylamine; In dichloromethane;	25a. 2-[N-(2-Methyl-2-sulfanylpropyl)carbamoyl]methoxy}acetic acid To an ice-cooled suspension of <strong>[32047-53-3]1-amino-2-methyl-2-propanethiol hydrochloride</strong> (4.21 g, 29.7 mmol) in CH2Cl2 (50 mL) was added Et3N (4.56 mL, 32.7 mmol) followed by diglycolic anhydride (3.43 g, 29.6 mmol). After stirring at room temperature for 30 minutes the reaction was concentrated under vacuum. Cold 2N HCl (50 mL) was added to the residue. The mixture was extracted with EtOAc (5*30 mL). The combined organic extracts were washed with brine (30 mL) and dried over Na2SO4. Concentration and trituration with Et2O:hexane gave the title compound as a white solid (5.50 g, 84.2%). mp 81-82 C.; 1H NMR (300 MHz, CDCl3) delta 8.80 (br s, 1H), 7.48 (br s, 1H), 4.24 (s, 2H), 4.20 (s, 2H), 3.41 (d, J=6.4 Hz, 2H), 1.59 (s, 1H), 1.38 ((s, 6H); 13C NMR (75 MHz, CDCl3) delta 172.8, 170.4, 70.8, 68.4, 51.9, 44.9, 29.8; mass spectrum (API-TIS) m/z 239 (M+NH4), 222 (M+H).
5.50 g (84%)	With triethylamine; In hydrogenchloride; dichloromethane;	9a. 2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]methoxy}acetic acid To an ice-cooled suspension of <strong>[32047-53-3]1-amino-2-methylpropane-2-thiol hydrochloride</strong> (4.21 g, 29.72 mmol) in methylene chloride (50 mL) was added triethylamine (4.56 mL, 32.72 mmol), followed by diglycolic anhydride (3.43 g, 29.55 mmol). After stirring at room temperature for 30 minutes, the reaction was concentrated in vacuo and cold 2 N HCl (50 mL) was added to the residue. The mixture was extracted with ethyl acetate (5*30 mL). The combined extracts were washed with brine (30 mL) and dried over anhydrous sodium sulfate. Volatiles were evaporated and the residue was triturated with ether/hexane to afford 5.50 g (84%) of the title compound as a white solid. mp 81-82 C.; 1H NMR (CDCl3, 300 MHz): 81.38 (s, 6H), 1.59 (s, 1H), 3.41 (d, 2H, J=6.4 Hz), 4.20 (s, 2H), 4.24 (s, 2H), 7.48 (br s, 1H), 8.80 (br s, 1H); 13C NMR (CDCl3, 75 MHz) delta29.83, 44.91, 51.90, 68.39, 70.77, 170.40, 172.84; LCMS (m/e): 239 (M+H2O), 222 (M+1).

5.50 g (84%)

With triethylamine; In hydrogenchloride; dichloromethane;

9a. 2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]methoxy}acetic Acid To an ice-cooled suspension of <strong>[32047-53-3]1-amino-2-methylpropane-2-thiol hydrochloride</strong> (4.21 g, 29.72 mmol) in methylene chloride (50 mL) was added triethylamine (4.56 mL, 32.72 mmol), followed by diglycolic anhydride (3.43 g, 29.55 mmol). After stirring at room temperature for 30 minutes, the reaction was concentrated in vacuo and cold 2 N HCl (50 mL) was added to the residue. The mixture was extracted with ethyl acetate (5*30 mL). The combined extracts were washed with brine (30 mL) and dried over anhydrous sodium sulfate. Volatiles were evaporated and the residue was triturated with ether/hexane to afford 5.50 g (84%) of the title compound as a white solid. mp 81-82 C.; 1H NMR (CDCl3, 300 MHz): delta1.38 (s, 6H), 1.59 (s, 1H), 3.41 (d, 2H, J=6.4 Hz), 4.20 (s, 2H), 4.24 (s, 2H), 7.48 (br s, 1H), 8.80 (br s, 1H); 13C NMR (CDCl3, 75 MHz) delta29.83, 44.91, 51.90, 68.39, 70.77, 170.40, 172.84; LCMS (m/e): 239 (M+H2O), 222 (M+1).

Reference： [1]Patent: US2002/10146,2002,A1
[2]Patent: US6297260,2001,B1
[3]Patent: US2002/143007,2002,A1
[4]Patent: US6469065,2002,B1

19
[ 20260-53-1 ]
[ 32047-53-3 ]
[ 307492-59-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide;	1a. N-(2-methyl-2-sulfanylpropyl)-3-pyridylcarboxamide <strong>[32047-53-3]1-Amino-2-methylpropane-2-thiol hydrochloride</strong> (1.10 g, 6.18 mmol) was dissolved in DMF and nicotinoyl chloride hydrochloride (1.14 g, 8.03 mmol) was slowly added as a solid. The mixture was cooled to 0 C. and triethylamine (3.0 mL, 21.63 mmol) was slowly added. The mixture was stirred for one half hour at 0 C., allowed to warm to room temperature, and stirred overnight. The reaction mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate, brine, and dried over magnesium sulfate. The volatiles were removed under reduced pressure to give a pink oil. An excess of hydrogen chloride in ether was added to precipitate 831 mg. (55%) of the title compound, mp. 163-165 C. 1H NMR (300 MHz, DMSO) delta9.00 (br s, 1H), 8.71 (dd, 1H, J=2.0, 4.9), 8.20 (dt, 1H, J=2.0, 7.9), 7.51 (dd, 1H, J=4.9, 7.9), 3.44 (d, 2H, J=6.3), 1.32 (s, 6H).

Reference： [1]Patent: US6417207,2002,B1

20
[ 108-30-5 ]
[ 32047-53-3 ]
3-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.4%	With triethylamine; In dichloromethane;	3a. 3-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]propanoic acid To an ice-cooled suspension of 1-amino-2-methylpropan2-thiol hydrochloride (5.06 g, 35.72 mmol) in methylene chloride (100 mL) was added triethylamine (5.0 mL, 35.87 mmol) followed by succinic anhydride (3.50 g, 34.96 mmol). The resulting clear solution was stirred at 0 C. or 10 minutes, then at room temperature for 2 hours. Evaporation of the volatiles under reduced pressure gave a residue which was partitioned between 2 N hydrochloric acid (100 mL) and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (3*100 mL). The combined organic layers were washed with brine (5 mL), dried over sodium sulfate and evaporated to dryness. The residue was triturated with ether-hexane to afford the title compound as a white solid (6.78 g, 94.4%). Mp. 86-87 C.; 1H NMR (300 MHz, CDCl3): delta1.34 (s, 6H), 1.55(s, 1H), 2.59 (t, J=6.6 Hz, H), 2.70 (t, J=6.6 Hz, 2H), 3.32 (d, J=8.0 Hz, 2), 6.58 (br t, J=5.9 Hz, 1H), 10.73 (br s, 1H); 13C NMR (75 MHz, CDCl3): delta29.57, 29.79, 30.79, 172.50, 176.81; LCMS (m/e): 223 (M+H2O), 206 (M+1).

Reference： [1]Patent: US2002/77343,2002,A1

21
[ 6050-13-1 ]
[ 32047-53-3 ]
2-{2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]phenyl}benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.9%	With hydrogenchloride; triethylamine; In dichloromethane;	16a. 2-{2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]phenyl}benzoic acid To an ice-cooled suspension of <strong>[32047-53-3]1-amino-2-methyl-2-propanethiol hydrochloride</strong> (1.08 g, 7.62 mmol) in methylene chloride (20 mL) was added triethylamine (1.2 mL, 8.61 mmol) followed by dibenzo[c,e]oxepin-5,7-dione (1.68 g, 7.42 mmol). After stirring at room temperature for 1 h, cold 2 N HCl (50 mL) was added. After separation, the aqueous layer was extracted with dichloromethane (2*15 mL). The combined organic layers were washed with brine and dried under sodium sulfate. The solvent was removed and the resulting residue was triturated with hexane to give the title compound as white solid (2.44 g, 98.9%). mp 150-153 C.; 1H NMR (CDCl3, 300 MHz): delta1.03 (s, 3H), 1.12 (s, 3H), 1.36 (s, 1H), 3.15 (dd, J=13.7 and 5.7 Hz, 1H), 3.38 (dd, J=13.7 and 6.9 Hz, 1H), 6.92 (t, J=6.1 Hz, 1H), 7.09-7.17 (m 2H), 7.38-7.48 (m, 4H), 7.57-7.61 (m, 1H), 7.80-7.83 (m, 1H); 13C NMR (CDCl3, 75 MHz,): delta29.36, 29.75, 44.66, 53.01, 127.28, 127.96, 128.04, 129.38, 129.93, 130.06, 130.20, 131.19, 132.02, 134.69, 138.90, 140.11, 170.99, 171.24; LCMS (m/e): 330 (M+1).
98.9%	With hydrogenchloride; triethylamine; In dichloromethane;	16a. 2-{2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]phenyl}benzoic Acid To an ice-cooled suspension of <strong>[32047-53-3]1-amino-2-methyl-2-propanethiol hydrochloride</strong> (1.08 g, 7.62 mmol) in methylene chloride (20 mL) was added triethylamine (1.2 mL, 8.61 mmol) followed by dibenzo[c,e]oxepin-5,7-dione (1.68 g, 7.42 mmol). After stirring at room temperature for 1 h, cold 2 N HCl (50 mL) was added. After separation, the aqueous layer was extracted with dichloromethane (2*15 mL). The combined organic layers were washed with brine and dried under sodium sulfate. The solvent was removed and the resulting residue was triturated with hexane to give the title compound as white solid (2.44 g, 98.9%). mp 150-153 C.; 1H NMR (CDCl3, 300 MHz): delta1.03 (s, 3H), 1.12 (s, 3H), 1.36 (s, 1H), 3.15 (dd, J=13.7 and 5.7 Hz, 1H), 3.38 (dd, J=13.7 and 6.9 Hz, 1H), 6.92 (t, J=6.1 Hz, 1H), 7.09-7.17 (m 2H), 7.38-7.48 (m, 4H), 7.57-7.61 (m, 1H), 7.80-7.83 (m, 1H); 13C NMR (CDCl3, 75 MHz,): delta29.36, 29.75, 44.66, 53.01, 127.28, 127.96, 128.04, 129.38, 129.93, 130.06, 130.20, 131.19, 132.02, 134.69, 138.90, 140.11, 170.99, 171.24; LCMS (m/e): 330 (M+1).

Reference： [1]Patent: US2002/143007,2002,A1
[2]Patent: US6469065,2002,B1

22
[ 32047-53-3 ]
[ 123-08-0 ]
[ 364056-23-5 ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium sulfate; potassium carbonate; In methanol; chloroform;	5a. 4-[(2-Methyl-2-sulfanylpropyl)amino]methyl}phenol To a hot solution of 4-hydroxybenzaldehyde (8.90 g, 72.8 mmol) in CHCl3 (250 mL) were added <strong>[32047-53-3]1-amino-2-methyl-2-propanethiol hydrochloride</strong> (10.32 g, 72.8 mmol), K2CO3 (20.2 g, 146 mmol), and MgSO4 (5 g). The mixture was stirred and refluxed under nitrogen atmosphere for 3 hours. After cooling, the mixture was filtered to remove inorganic solid, and the filter cake was washed through with MeOH (2*100 mL). Evaporation of the filtrate afforded the product 5a as a white solid (15 g, 98%). mp 85-87 C.; 1H NMR (CDCl3, 300 MHz) delta 7.38 (d, J=8.5 Hz, 2H), 6.76 (d, J=8.5 Hz, 2H), 5.74 (s, 1H), 3.25 (d, J=12.1 Hz, 1H), 3.01 (d, J=12.1 Hz, 1H), 1.59 (s, 3H), 1.58 (s, 3H).

Reference： [1]Patent: US6297260,2001,B1

23
[ 313273-69-7 ]
[ 32047-53-3 ]
8-(2-amino-1,1-dimethyl-ethylsulfanyl)-3-methyl-7-(3-methyl-but-2-enyl)-3,7-dihydro-purin-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide;	Example 5 8-(2-Amino-1,1-dimethylethylsulfanyl)-3-methyl-7-(3-methylbut-2-enyl)-3,7-dihydropurine-2,6-dione A mixture of 80 mg of 8-bromo-3-methyl-7-(3-methylbut-2-enyl)-3,7-dihydropurine-2,6-dione, 90 mg of <strong>[32047-53-3]1-amino-2-methyl-2-propanethiol hydrochloride</strong>, 2 ml of DMF and 200 mg of cesium carbonate was stirred at 70 C. for 5 hours. After concentration, the oily residue was purified by column chromatography (silica gel, mobile phase: methylene chloride: methanol =9:1). Yield: 85 mg m.p.: oil MS: M+1=338

Reference： [1]Patent: US2007/265284,2007,A1
[2]Patent: WO2006/15691,2006,A1 .Location in patent: Page/Page column 35

24
[ 875877-40-0 ]
[ 32047-53-3 ]
[ 876134-85-9 ]

Reference： [1]Patent: WO2006/15691,2006,A1 .Location in patent: Page/Page column 34

25
bis(tetraethylammonium) di-μ-sulfido-bis[sulfido-bis(benzenethiolato)]molybdate(V) [ No CAS ]
[ 32047-53-3 ]
[ 178447-21-7 ]

Reference： [1]Inorganica Chimica Acta,1996,vol. 243,p. 147 - 160

26
[ 32047-53-3 ]
[ 7733-02-0 ]
copper(II) oxide [ No CAS ]
[ 72244-66-7 ]

Reference： [1]Inorganic Chemistry,1980,vol. 19,p. 543 - 552

27
[ 32047-53-3 ]
[ 7733-02-0 ]
copper(II) oxide [ No CAS ]
[ 72214-16-5 ]

Reference： [1]Inorganic Chemistry,1980,vol. 19,p. 543 - 552

28
[ 14057-91-1 ]
[ 32047-53-3 ]
[ 72244-67-8 ]

Reference： [1]Inorganic Chemistry,1980,vol. 19,p. 543 - 552

29
zinc(II) sulfate heptahydrate [ No CAS ]
cobalt(II) chloride hexahydrate [ No CAS ]
[ 32047-53-3 ]
0.5Co⁽²⁺⁾*0.5Zn⁽²⁺⁾*2{SC(CH₃)2CH₂NH₂}^(1-)=Co_0.5Zn_0.5{SC(CH₃)2CH₂NH₂}2 [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 4072 - 4081

30
bis(acetylacetonato)dioxidomolybdenum(VI) [ No CAS ]
[ 32047-53-3 ]
[ 76757-49-8 ]

Reference： [1]Inorganic Chemistry,1984,vol. 23,p. 3404 - 3412

31
[ 31716-01-5 ]
[ 32047-53-3 ]
[ 133787-61-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrabutylammomium bromide; sodium hydroxide; In tetrahydrofuran; water; at 50℃; for 3h;Inert atmosphere;	To a stirred solution of starting material (196 mg, 0.37 mmol), <strong>[32047-53-3]1-amino-2-methylpropane-2-thiol hydrochloride</strong> (104 mg, 0.74 mmol) and tetra-nbutylammonium bromide (11.9 mg, 0.037 mmol) in THF (1.5 mL) was added iNNaOH (1.5 mL). After 3 h at 50 C, the reaction mixture was extracted with CHC13(1, 2). The combined organic extract was dried over Na2SO4, concentrated in vacuo.The crude product was purified by silica gel column chromatography (hexanes/EtOAc50:50 to CHC13/MeOH 75:25) to give the product (140 mg, 0.30 mmol, 82%): TLC(CHC13/MeOH 90:10) Rf= 0.20; [a]20D +0.335 (c = 1.49, CHC13); JR (thin film) Vmax= 3433 (br), 2928, 2881, 2864, 1726, 1631, 1524, 1457, 1412, 1375, 1281, 1152,1119, 1033, 1010, 980, 954, 938, 916, 816, 754, 683 cm?; ?H NMR (400 MHz,Chloroform-d) 6.48 (dd, J= 17.4, 11.0 Hz, 1H), 5.76 (d, J= 8.4 Hz, 1H), 5.36 (dd, J= 10.9, 1.5 Hz, 1H), 5.21 (dd, J= 17.4, 1.6 Hz, 1H), 3.36 (d, J= 6.5 Hz, 1H), 3.15 (d,J = 2.3 Hz, 2H), 2.63 (s, 2H), 2.38 - 2.30 (m, 1H), 2.32 - 2.14 (m, 2H), 2.13 - 2.03(m, 2H), 1.87 (brs, 2H), 1.77 (dq, J= 14.4, 3.1 Hz, 1H), 1.71 -1.61 (m, 2H), 1.60-1.50 (m, 2H), 1.50 - 1.47 (m, 1H), 1.46 (s, 3H), 1.41 - 1.33 (m, 1H), 1.26 (s, 6H),1.17 (s, 3H), 1.11 (dd, J= 14.0,4.3 Hz, 1H), 0.88 (d, J= 7.0 Hz, 3H), 0.73 (d, J= 6.9Hz, 3H); ?3C NMR (101 MHz, CDC13) 216.94, 169.57, 139.01, 117.30, 74.64,69.52, 58.21, 51.42, 48.22, 45.47, 44.78, 43.95, 41.82, 36.79, 36.03, 34.46, 31.32,30.46, 26.87, 26.34, 26.33, 26.29, 24.87, 16.86, 14.92, 11.50; FIRMS (ESJ+) m/z calcd for C26H44N04S [M + H] 466.2991, found: 466.3016.
82%	With tetrabutylammomium bromide; sodium hydroxide; In tetrahydrofuran; water; at 50℃; for 3h;Inert atmosphere;	To a stirred solution of 10 (196 mg, 0.37 mmol), <strong>[32047-53-3]1-amino-2-methylpropane-2-thiol hydrochloride</strong> (104 mg, 0.74 mmol) and tetra-nbutylammoniumbromide (11.9 mg, 0.037 mmol) in THF (1.5 mL) wasadded 1 N NaOH (1.5 mL). After 3 h at 50 C, the reaction mixture wasextracted with CHCl3. The combined organic extract was dried overNa2SO4, concentrated in vacuo. The crude product was purified by silicagel column chromatography (hexanes/EtOAc 50:50 to CHCl3/MeOH75:25) to give 11 (140 mg, 0.30 mmol, 82%): TLC (CHCl3/MeOH90:10) Rf=0.20; [alpha]20D +0.335 (c=1.49, CHCl3); IR (thin film)numax=3433 (br), 2928, 2881, 2864, 1726, 1631, 1524, 1457, 1412,1375, 1281, 1152, 1119, 1033, 1010, 980, 954, 938, 916, 816, 754,683 cm-1; 1H NMR (400 MHz, Chloroform-d) delta 6.48 (dd, J=17.4,11.0 Hz, 1H), 5.76 (d, J=8.4 Hz, 1H), 5.36 (dd, J=10.9, 1.5 Hz, 1H),5.21 (dd, J=17.4, 1.6 Hz, 1H), 3.36 (d, J=6.5 Hz, 1H), 3.15 (d,J=2.3 Hz, 2H), 2.63 (s, 2H), 2.38-2.30 (m, 1H), 2.32-2.14 (m, 2H),2.13-2.03 (m, 2H), 1.87 (brs, 2H), 1.77 (dq, J=14.4, 3.1 Hz, 1H),1.71-1.61 (m, 2H), 1.60-1.50 (m, 2H), 1.50-1.47 (m, 1H), 1.46 (s, 3H),1.41-1.33 (m, 1H), 1.26 (s, 6H), 1.17 (s, 3H), 1.11 (dd, J=14.0,4.3 Hz, 1H), 0.88 (d, J=7.0 Hz, 3H), 0.73 (d, J=6.9 Hz, 3H); 13CNMR (101 MHz, CDCl3) delta 216.94, 169.57, 139.01, 117.30, 74.64,69.52, 58.21, 51.42, 48.22, 45.47, 44.78, 43.95, 41.82, 36.79, 36.03,34.46, 31.32, 30.46, 26.87, 26.34, 26.33, 26.29, 24.87, 16.86, 14.92,11.50; HRMS (ESI+) m/z calcd for C26H44NO4S [M+H] 466.2991,found: 466.3016.
5.03 g		Metallic sodium (0.69 g, 30 mmol) was cut into small pieces and added portion wise to absolute ethanol (150 mL). After metallic sodium had been dissolved completely at room temperature, the solution was filtered and <strong>[32047-53-3]1-amino-2-methyl-2-propanethiol hydrochloride</strong>(2.12 g, 15 mmol) was added. The mixture was stirred for 0.5 h at room temperature, followed by freezing to 0C and compound 2 (7.99 g, 15 mmol) was added. The mixture was stirred in an ice bath for 2.5 h, evaporated under reduced pressure to 50 mL, extracted with ethyl acetate (100 mL) and washed with water (200 mL). The organic layer was separated and dried with anhydrous Na2SO4 overnight. The organic solvent was evaporated in vacuum and the residue was purified by recrystallization with ethyl acetate or column chromatography (silica gel, ethyl acetate:ethanol 10:1 v/v). the product was obtained (5.03 g, 72%). mp:154-155C; IR (free base, KBr): 3351, 2956, 2864, 1734, 1721, 1634,1456, 1373, 1274, 1209, 1112, 1033, 982, 955, 941, 916 cm1; 1H NMR(400 MHz, CDCl3) d 0.73 (d, 3H, J 7.2 Hz), 0.87 (d, 3H, J 7.2 Hz),1.09-1.16 (m, 1H), 1.23 (s, 6H), 1.30-1.38 (m, 2H), 1.45 (s, 1H), 1.52-1.53 (m, 7H), 1.55-1.60 (m, 1H), 1.63-1.69 (m, 2H), 1.74-1.78(q, 1H,J 0.8 Hz), 2.04-2.10 (q, 2H), 2.18-2.25(m, 2H), 2.32-2.59 (q, 1H,J 6.8 Hz), 3.09 (s, 2H), 3.13-3.17 (t, 2H, J 1.6 Hz), 3.35 (d, 1H,J 6.4 Hz), 5.17-5.22 (q, 1H, J 1.6 Hz), 5.31-5.34 (q, 1H,J 1.2 Hz), 5.74(d, 1H, J 8.4), 6.44-6.51 (q, 1H, J1 11.2 Hz,J2 10.8 Hz); 13C NMR (100 MHz, CDCl3) d 216.9, 169.4, 139.0, 117.1,74.6, 69.3, 58.2, 51.7, 48.5, 45.4, 44.7, 43.9, 41.8, 36.7, 35.9, 34.4, 31.2,30.4, 26.8, 26.3, 26.2, 24.8, 16.8, 14.9, 11.4.

Reference： [1]Journal of Chemical Research,2010,p. 354 - 357
[2]Patent: WO2018/152408,2018,A1 .Location in patent: Page/Page column 50
[3]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 4787 - 4796
[4]Letters in drug design and discovery,2013,vol. 10,p. 219 - 225
[5]European Journal of Medicinal Chemistry,2013,vol. 63,p. 231 - 238

32
rac-2-isopropyl-5,5-dimethyl-1,3-thiazolidine [ No CAS ]
[ 32047-53-3 ]
[ 78-84-2 ]

Yield	Reaction Conditions	Operation in experiment
2.7 kg	With hydrogenchloride; In water;Reflux; Large scale;	Containing 5,5-dimethyl-2-isopropyl thiazolidine water layer, heated up to reflow, atmospheric water and reaction generated Isobutyraldehyde, side distillation-side reaction, the reaction produces dimethyl shown acid salt of ammonia salt, after the end of the water pressure reducing concentrated dry, re-use anhydrous ethanol with two. Adding anhydrous ethanol heating dissolution, dripping acetic acid ethyl ester. Cooling the crystal separation, centrifugal, a dried nickelio deaminatio hydrochloride.Get 2.65 kg dimethyl cysteamine hydrochloride content 99.2%, molar yield of products 73.6%, total mole yield three-step reaction of 57.7%.

Reference： [1]Patent: CN105367467,2016,A .Location in patent: Paragraph 0024; 0027; 0028; 0031; 0032; 0035; 0036

33
[ 32047-53-3 ]
[ 58262-78-5 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sodium hydroxide; In methanol; for 0.25h;	General procedure: 1-Amino-2-propanethiol hydrochloride (1b) was prepared accordingto the procedure described by Fujita et al. [67]. In a three-neckedflask, 1-amino-2-propanethiol hydrochloride (10.0 g, 78.7 mmol) wassuspended in methanol (120 mL) and sodium hydroxide (3.34 g,83.4 mmol) was added. Next, 1,3-dibromo-5,5-dimethylhydantoin(8.66 g, 30.3 mmol) was added, and the mixture was stirred overnight.Sodium hydroxide (13.3 g, 532 mmol) was added to the in situ formeddisulfide and a solution of acryloyl chloride (27.0 mL, 332 mmol) in dichloromethane(66mL)was added dropwise at 0 C. After stirring overnightat room temperature, pH was adjusted to pH = 8 and the whiteprecipitate was filtered off. The reaction mixture was extracted threetimes using dichloromethane and the organic phase was dried usingmagnesium sulfate. The crude product was purified by filtration over aslab of silica followed by recrystallization from boiling ethyl acetate.N,N?-dithiobis(2-methylethyl)bisacrylamide (2b) was obtained as awhite solid (0.980 g, 8.6%).

Reference： [1]Journal of Controlled Release,2016,vol. 244,p. 357 - 365

34
[ 31716-01-5 ]
[ 32047-53-3 ]
C₂₆H₄₃NO₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.1%	With benzyltri(n-butyl)ammonium chloride; sodium hydroxide; In tetrahydrofuran; at 35 - 45℃; for 1h;pH 8.0;	In the is provided with a stirrer of 500 ml three-neck bottle in, adding compound 12 (145.0g, 0 . 27 muM), dimethyl half light amine hydrochloride (38.3g, 0 . 27 muM) and 300 ml tetrahydrofuran, for 35 C under stirring, adding benzyl three-butyl ammonium chloride 7.5g and of 30 ml 10N NaOH solution, adjusting the pH to 8, control the reaction temperature is 40 C, violent stirring; then heating up to 40 C -45 C, reaction 1 hours. After the reaction, adding 450 ml water to dilute the reaction liquid, the reaction liquid-cooled to 10 C, at this temperature the stirring 15 minutes, filter, water and cold tetrahydrofuran (150 ml × 2) washing the filter cake, 55 C drying overnight, shall 116g dimethyl half light amine pleuromutilin crude product, the reaction yield 92.3%, melting point 144.6 C -146.7 C. Ethyl ether dimethyl half light amine pleuromutilin recrystallizing the crude product, obtained 108.2g white solid, namely g dimethyl half light amine pleuromutilin finished product. Product melting point 148.5 C -149.5 C, recrystallized yield 86.1%.

Reference： [1]Patent: CN106432017,2017,A .Location in patent: Paragraph 0061; 0074; 0087; 0100

35
(3R,3aR,4R,5R,7S,8S,9R,9aS,12R)-3,8-dihydroxy-4,7,9,12-tetramethyl-7-vinyldecahydro-4,9a-propanocyclopenta[8]-annulen-5-yl 2-(tosyloxy)acetate [ No CAS ]
[ 32047-53-3 ]
(3R,3aR,4R,5R,7S,8S,9R,9aS,12R)-3,8-dihydroxy-4,7,9,12-tetramethyl-7-vinyldecahydro-4,9a-propanocyclopenta[8]-annulen-5-yl 2-((1-amino-2-methylpropan-2-yl)thio)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With tetrabutylammomium bromide; sodium hydroxide; In tetrahydrofuran; at 50℃; for 4h;Inert atmosphere;	To a stirred solution of starting material (10.5 g, 19.7 mmol), l-amino-2- methylpropane-2-thiol hydrochloride (5.58 g, 39.4 mmol) and tetra-n-butylammonium bromide (0.64 g, 1.97 mmol) in THF (80 mL) was added 1NNaOH (79.2 mL). After4 h at 50 C, the reaction mixture was extracted with CHC13. The combined organic extract was dried over Na2SO4, concentrated in vacuo. The crude product was purified by silica gel column chromatography (hexanes/EtOAc 50:50 to CHC13/MeOH 75:25) to give (8.75 g, 18.7 mmol, 95%): TLC (CHC13/MeOH 90:10) Rf= 0.20; [a]21D -0.062 (c = 0.87, CHC13); JR (thin film) vm, = 3421 (br), 2955, 2876,1721, 1462, 1371, 1283, 1219, 1121, 1020,1005,932, 772cm?; ?H NMR (400 MHz,Chloroform-d) 6.51 (dd, J= 17.4, 11.0 Hz, 1H), 5.60 (d, J= 9.4 Hz, 1H), 5.32 (dd, J= 11.0, 1.7 Hz, 1H), 5.16 (dd, J= 17.4, 1.7 Hz, 1H), 4.55 (t, J= 5.5 Hz, 1H), 3.16 (d,J = 6.4 Hz, 1H), 3.13 (s, 2H), 2.61 (s, 2H), 2.26 - 2.18 (m, 1H), 2.15 (t, J = 6.8 Hz,1H), 2.08 (dd, J= 15.8, 9.3 Hz, 1H), 2.00-1.91 (m, 1H), 1.85 (td, J= 13.7, 4.5 Hz,1H), 1.74- 1.58 (m, 4H), 1.51 (d, J= 5.2 Hz, 1H), 1.48- 1.41 (m, 2H), 1.41 -1.33(m, 1H), 1.24 (s, 6H), 1.23 (s, 3H), 1.14 (s, 3H), 0.80 (d, J= 7.0 Hz, 3H), 0.71 (d, J=7.0 Hz, 3H); ?3C NMR (101 MHz, CDC13) 169.38, 139.56, 116.66, 74.93, 71.25,51.68, 51.01, 48.44, 46.00, 45.20, 44.86, 41.24, 36.62, 35.61, 34.31, 32.63, 31.76,31.33, 27.66, 26.30, 26.25 (2C), 17.64, 17.21, 12.16; HRMS (ESJ+) m/z calcd forC26H46N04S [M + H] 468.3148, found: 468.3181.

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 2869 - 2878
[2]Patent: WO2018/152408,2018,A1 .Location in patent: Page/Page column 30
[3]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 4787 - 4796

36
[ 32047-53-3 ]
[ 407-25-0 ]
2,2,2-trifluoro-N-(2-mercapto-2-methylpropyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With pyridine; In benzene; at 0 - 20℃;	2,2,2-trifluoro-N-(2-mercapto-2-methylpropyl)acetamide (4): l-amino-2-methylpropane-2- thiol hydrochloride (3) (1.0 g, 7 mmol) was mixed with pyridine (2mL) in dried benzene (15mL). At 0 C, trifluoroacetic anhydride ( 1.30 mL, 9.2 mmol) was slowly added to the stirred mixture, and stirring was continued overnight at ambient temperature. Careful addition of 0.5 M NaaCC^/HaO was followed by extraction (EtOAc) of the aqueous layer and removal of volatiles from the combined organic layers under vacuum. Flash chromatography of the residue (30% ethyl acetate/hexane) gave 4 (4.0 g, 88%): NMR (400 MHz, CDCI3) S: 6.85(br, 1H), 3.45 (m, 2H), 1.69 (s, 1H), 1.41 (s, 6H).

Reference： [1]Patent: WO2017/58953,2017,A1 .Location in patent: Paragraph 0900; 0902

37
C₃₀H₄₃NO₇S [ No CAS ]
[ 32047-53-3 ]
C₂₇H₄₆N₂O₄S [ No CAS ]

Reference： [1]Patent: WO2018/152408,2018,A1 .Location in patent: Page/Page column 56

38
[ 23429-44-9 ]
[ 32047-53-3 ]
C₂₄H₂₇NS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium hydrogencarbonate; In water; acetonitrile; at 20℃; for 24h;Inert atmosphere;	[00169] DMCA- HCI (5 mmol, 0.707 g) was dissolved in water (20 mL) in a reaction flask. A solution of 4-methyl trityl chloride (Mtt-CI; 5 mmol, 1 .464 g) in CH3CN (30 mL) was added to the reaction and followed by addition of aqueous NaHCO3 (10 mmol, 0.890 g, 10 mL) solution. The reaction was allowed to stir under an inert (N2) atmosphere for 24 h at RT. The reaction mixture was transferred to a separating funnel to which an excess of EtOAc (100 mL) was added. The organic phase was collected and the remaining aqueous phase was washed with EtOAc (2 x 50 mL). All organic phases were pooled and dried over MgSO4 to remove any residual water. EtOAc was removed in vacuo and the final product was collected as a clear, viscous liquid. The crude product was purified by column chromatography with n-hexane and EtOAc (3:2) as the solvent mixture. Yield (55%, 0.99 g).TLC: Revalue 0.80 (n-hexane: EtOAc=3:2, UV active, illuminates under UV light). HRMS (ESI-TOF): [M-H]+calculated for C24H26NS-, 360.1791 , found 360.1787.1H NMR (500 MHz, CDC ): delta 1 .44 (s, 6H, 2CH3), 1 .69 (s, H, SH), 2.18 (s, 3H, CH3), 2.33 (s, 2H, CH2), 7.12 (d, J= 8.10 Hz, 2H, Mtt), 7.20 (t, J= 7.35 Hz, 2H, Mtt), 7.29 (t, J=7.90 Hz, 4H, Mtt), 7.42 (d, J= 8.25 Hz, 2H, Mtt), 7.54 (d, J=7.40 Hz, 4H, Mtt);13C NMR (500 MHz, CDCb): 21 .1 , 31 .1 , 45.8, 56.9, 70.3, 126.3, 127.4, 128.1 , 128.7, 129.4, 135.9, 143.26, 146.4 ppm.

Reference： [1]Patent: WO2019/18892,2019,A1 .Location in patent: Paragraph 00169

39
[ 24424-99-5 ]
[ 32047-53-3 ]
[ 134362-01-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydrogencarbonate; In water; acetonitrile; at 20℃; for 24h;Inert atmosphere;	[00167] Dimethylcysteamine hydrochloride (DMCA- HCI) (5 mmol, 0.707 g) was dissolved in water (20 imL) in a reaction flask. A solution of di-te/t-butyl dicarbonate (10 mmol, 2.180 g) in CH3CN (30 imL) was added to the reaction mixture and followed by addition of aqueous NaHCO3 (10 mmol, 0.890 g in 10 mL) solution. The reaction was allowed to stir under an inert (N2) atmosphere at RT for 24 h. The reaction mixture was transferred into a separating funnel and added with an excess of EtOAc (100 mL). The organic phase was collected separately and the remaining aqueous phase washed with EtOAc (2 x 20 mL). All organic phases were pooled and dried over MgSO4 to remove any residual water. EtOAc was removed in vacuo and the final product was collected as a viscous liquid and vacuum dried overnight to remove any traces of EtOAc. Yield (82%, 0.84 g). TLC: Re value 0.85 (n- hexane: EtOAc = 3:2, UV inactive, stained with KMnO4 produces yellow spot upon drying). HRMS (ESI-TOF): [M-H]+calculated for C9H19NO2S-, 204.1063, found 204.1021 ;1H NMR (500 MHz, CDC ): delta 1 .33 (s, 6H, 2CH3), 1 .44 (s, 9H, 3CH3-B0C), 1 .62 (s, H, SH), 3.19 (d, J=6.10 Hz, 2H, CH2), 4.98 (s, 1 H, NHCO);13C NMR (500 MHz, CDCb): delta 25.4, 28.5, 48.3, 80.4, 156.1 ppm.

Reference： [1]Patent: WO2019/18892,2019,A1 .Location in patent: Paragraph 00167

40
[ 82911-69-1 ]
[ 32047-53-3 ]
Fmoc-DMCA [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium hydrogencarbonate; In water; acetonitrile; at 20℃; for 18h;Inert atmosphere;	[00168] DMCA- HCI (5 mmol, 0.707 g) was dissolved in water (20 mL) within a reaction flask. Separately, Fmoc-N-hydroxysuccinimide ester (5 mmol, 1 .685 g) was dissolved in CH3CN (30 mL) and added to the reaction followed by addition of aqueous NaHCO3 (10 mmol, 0.890 g, 10 mL) solution. The reaction was allowed to stir under an inert atmosphere (N2) at RT for 18 h, after which it was transferred into a separating funnel and excess of EtOAc (100 mL) was added. The organic phase was collected and the remaining aqueous phase was washed with EtOAc (2 x 20 mL). The organic phases were pooled and dried over MgSO4 to remove residual water. EtOAc was removed in vacuo and the resultant white solid product was collected and dried under vacuum. Further, the final yellowish white coloured solid product was purified by column chromatography with solvent mixture of n-hexane and EtOAc (3:2). Yield (67%, 1 .09 g). TLC: Rf = 0.78 (n-hexane: EtOAc = 3:2, UV active, illuminates under UV light). HRMS (ESI-TOF): [M+Na]+calculated for C19H21 NNaO2S+, 350.1 191 , found 350.1573. 1 H NMR (500 MHz, CDCb): delta 1 .35 (s, 6H, 2CH3), 1 .63 (s, H, SH), 3.28 (d, J=6.50 Hz, 2H, CH2), 4.24 (t, J=6.78 Hz 1 H, CH- Fmoc), 4.44 (d, J=6.90 Hz, 2H, CH2-Fmoc), 5.23 (s, 1 H, NHCO), 7.30-7.33 (td, J=7.46 Hz 2H, Fmoc), 7.40 (t, J=7.46 Hz, 2H, Fmoc), 7.61 (d, J= 7.45 Hz, 2H, Fmoc), 7.77 (d, J=7.46 Hz, 2H, Fmoc);13C NMR (500 MHz, CDCb): delta 29.8, 45.6, 47.4, 54.3, 66.8, 120.1 , 125.1 , 127.2, 127.8, 141 .4, 144.0, 156.7 ppm

Reference： [1]Patent: WO2019/18892,2019,A1 .Location in patent: Paragraph 00168

41
[ 126049-37-4 ]
[ 32047-53-3 ]
C₁₁H₁₇NOS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In water; acetonitrile; at 20℃; for 18h;	A solution of Compound No. 1 (506 mg, 2.03 mmol) and <strong>[32047-53-3]dimethylcysteamine hydrochloride</strong> (375 mg, 2.65 mmol) in acetonitrile/water (6 mL/6 mL) was stirred at room temperature for 18 hours. LC/MS showed the disappearance of Compound No. 1. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with a saturated NaHCO3 aqueous solution (100 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate/MeOH/triethylamine, v/v, 1/0/0 to 100/10/3) to give Compound No. 2 (460 mg, 93% yield) as a light yellow solid. LC-MS: 244 [M+1]+.

Reference： [1]Patent: US2019/151462,2019,A1 .Location in patent: Paragraph 0533; 0535

42
[ 2949-92-0 ]
[ 32047-53-3 ]
[ 959751-65-6 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium phosphate buffer; In methanol; at 25℃;pH 7.4;	l-amino-2-methylpropane-2-thiol hydrochloride (2.5 g, 17.65 mmol) was suspended in MeOH (7.5 mL) and potassium phosphate buffer pH 7.4 (7.50 mL). Methylmethane- thiolsulfonate (2.499 mL, 26.5 mmol) was added and the reaction was stirred at rt overnight. The reaction mixture was diluted with EtOAc and was washed with brine. The organic layer was dried over Na2S04, filtered and concentrated. The crude product was purified by silica gel chromatography (DCM/MeOH) to yield compound 12 as a white solid (1.34 g, 50% yield). 1H NMR (400 MHz, DMSO /6): d 1.34 (s, 6H), 2.45 (s, 3H), 2.94 (s, 2H), 8.13 (s, 2H).
50%	In methanol; aq. phosphate buffer; at 20℃;pH 7.4;	<strong>[32047-53-3]1-amino-2-methylpropane-2-thiol hydrochloride</strong> (2.5 g, 17.65 mmol) was suspended in methanol(7.5 mL) and potassium phosphate buffer pH 7.4 (7.50 mL). Methylmethane-thiolsulfonate (2.499mL, 26.5 mmol) was added and the reaction was stirred at room temperature overnight. Thereaction mixture was diluted with ethyl acetate and was washed with brine. The organic layer wasdried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gelchromatography (dichloromethane/methanol) to yield 2-methyl-2-methyldithiopropan-1-amine asa white solid (1.34 g, 50% yield). 1H NMR (400 MHz, DMSO-d6): delta 1.34 (s, 6H), 2.45 (s, 3H),2.94 (s, 2H), 8.13 (s, 2H).

Reference： [1]Patent: WO2019/133652,2019,A1 .Location in patent: Page/Page column 138; 139; 143
[2]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2455 - 2458

43
[ 2127-03-9 ]
[ 32047-53-3 ]
2-methyl-2-(pyridin-2-yldisulfanyl)propan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		Dimethylcysteamine· HC1, 18 (500 mg, 3.53 mmol) was dissolved in MeOH (11.765 mL). Aldrithiol, 19 (1.17 g, 5.29 mmol) was added and the reaction mixture was stirred at rt overnight. TEA (0.492 mL, 3.53 mmol) was added and the reaction was stirred at rt for 5 min and then concentrated. The crude residue was purified by silica gel chromatography (0% to 5% to 10% MeOH/DCM) to obtain compound 20 as an off white sticky solid (700 mg, 3.27 mmol, 93% yield). LCMS = 2.874 min (8 min method). Mass observed (ESI+): 214.95 (M+H). 1H NMR (400 MHz, CDCl3): d 1.49 (s, 6H), 2.95 (s, 2H), 7.17 (ddd, 7 = 7.4, 5.0, 1.0 Hz, 1H), 7.42 (dt, 7 = 8.0, 1.0 Hz, 1H), 7.54 - 7.64 (m, 1H), 8.65 (ddd, 7 = 4.9, 1.9, 0.9 Hz, 1H).

Reference： [1]Patent: WO2019/133652,2019,A1 .Location in patent: Page/Page column 138; 139; 145; 146

44
[ 221462-58-4 ]
[ 32047-53-3 ]

Yield	Reaction Conditions	Operation in experiment
31.6 g	With hydrogenchloride; In water; at 115℃; for 40h;	Directly add 10 molar equivalents of concentrated hydrochloric acid to the above 5,5-dimethyl-2-(2-pyridyl)thiazolidine mother liquor, warm to 115C for 40 hours, and distill the low-boiling matter at atmospheric pressure while reacting. After dehydration, the crude product was crystallized to obtain 31.6 g of dimethylcysteamine hydrochloride, and its content was still as high as 98.0% after testing.

Reference： [1]Patent: CN110981828,2020,A .Location in patent: Paragraph 0034; 0036

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Precautionary Statements-General
Code	Phrase
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P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P232	Protect from moisture.
P233	Keep container tightly closed.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
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P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
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P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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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[ 32047-53-3 ] Synthesis Path-Downstream 1~44

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