6846-35-1

Basic information

• Product Name: 5-Amino-3H-1,2,4-dithiazole-3-thione
• Synonyms: 3-AMINO-1,2,4-DTHIAZOLE-5-THIONE;5-AMINO-[1,2,4]DITHIAZOLE-3-THIONE;XANTHANE HYDRIDE;4-dithiazole-3-thione,5-amino-2;Nsc65248;3-AMino-1;4-dithiazole-5-thione;3-Amino-3H-1,2,4-dithiazole-5-thione, 5-Amino-3-thioxo-3H-1,2,4-dithiazole
• CAS NO: 6846-35-1
• Molecular Formula: C₂H₂N₂S₃
• Molecular Weight: 150.25
• EINECS: 229-933-3
• Product Categories: AMINEPRIMARY
• Mol File: 6846-35-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 201-203°C
• Boiling Point: 2.00 °C
• Flash Point: 124 °C
• Appearance: /solid
• Density: 2.00
• Vapor Pressure: 0.00344mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: 2-8°C(protect from light)
• PKA: -1.03±0.20(Predicted)
• CAS DataBase Reference: 5-Amino-3H-1,2,4-dithiazole-3-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-3H-1,2,4-dithiazole-3-thione(6846-35-1)
• EPA Substance Registry System: 5-Amino-3H-1,2,4-dithiazole-3-thione(6846-35-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: JO6500000
• Hazardous Substances Data: 6846-35-1(Hazardous Substances Data)

Usage

Uses

3-Imino-3H-1,2,4-dithiazole-5-thiol is used in preparation of amino dithiazole thione.

InChI:InChI=1/C2H2N2S3/c3-1-4-2(5)7-6-1/h(H2,3,4,5)

Synthetic route

S,S-dimethyl dithiocarbonate + thiourea (17356-08-0) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1)

Conditions	Yield
Stage #1: S,S-dimethyl dithiocarbonate; thiourea With toluene-4-sulfonic acid In ethanol for 6h; Reflux; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In ethanol at 30 - 50℃; for 14h; Concentration;	95.4%

thiocyanic acid (463-56-9) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1)

Conditions	Yield
With water
With water

ammonium thiocyanate (1147550-11-5) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1)

Conditions	Yield
With hydrogenchloride In water for 6h;	35%
With hydrogenchloride; water Reinigung ueber das Bariumsalz der Persulfocyansaeure;
With sulfuric acid

3,5-di(3,4,4-trifluoro-3-butenylthio)-1,2,4-thiadiazole + bis-potassium salt of 3,5 dimercapto 1,2,4-thiadiazole → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 3-(4-nitrophenylmethylthio)-5-(3,4,4-trifluoro-3-butenylthio)-1,2,4-thiadiazole

Conditions	Yield
In water

thiocyanic acid (463-56-9) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + cyano-dithiocarbamic acid (108-04-3)

Conditions	Yield
With water
With mineral acid

potassium-salt of/the/ trithioallophanic acid → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1)

Conditions	Yield
With acid aqueous solution; iron(III) chloride

trithioallophanic acid (74237-96-0) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1)

Conditions	Yield
With sulfuric acid

potassium thioacyanate (333-20-0) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1)

Conditions	Yield
With sulfuric acid; water

isothiocyanic acid (3129-90-6) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + hydrogen cyanide (74-90-8)

thiocyanic acid (463-56-9) + water (7732-18-5) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + cyano-dithiocarbamic acid (108-04-3) + hydrogen cyanide (74-90-8)

thiocyanic acid (463-56-9) + water (7732-18-5) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + hydrogen cyanide (74-90-8)

[1,2,4]thiadiazolidine-3,5-dithione (20939-17-7) + water (7732-18-5) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1)

Conditions	Yield
wird durch SO2, H2S und <1.3.4>Thiadiazolidin-2.5-dithion in wss. HCl katalysiert;

thiocyanic acid (463-56-9) + concentrated mineral acid → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + cyano-dithiocarbamic acid (108-04-3) + hydrogen cyanide (74-90-8)

trithioallophanic acid (74237-96-0) + sulfuric acid (7664-93-9) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + hydrogen sulfide (7783-06-4)

ethanol (64-17-5) + phosphorus tri-isothiocyanate (1858-23-7) + benzene (71-43-2) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + thiocyanic acid (463-56-9)

acetyl isothiocyanate (13250-46-9) + diluted acid → carbon disulfide (75-15-0) + 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + thiocyanic acid (463-56-9) + acetic acid (64-19-7)

Conditions	Yield
Produkt 5: Kohlenoxysulfid;

phosphoryl-isothiocyanate (1858-25-9) + water (7732-18-5) → 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + thiocyanic acid (463-56-9) + phosphoric acid (86119-84-8, 7664-38-2)

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 4-nitro-aniline (100-01-6) → 1-(4-nitrophenyl)dithiobiuret

Conditions	Yield
Stage #1: 5-amino-3H-1,2,4-dithiazole-3-thione With triphenylphosphine In acetonitrile at 30℃; for 0.0833333h; Stage #2: 4-nitro-aniline In acetonitrile for 15h; Further stages.;	97%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 2-amino-phenol (95-55-6) → 2-thioureidobenzoxazole

Conditions	Yield
In ethanol Heating;	96%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 1,2-diamino-benzene (95-54-5) → 2-thioureidobenzimidazole (62530-07-8)

Conditions	Yield
In ethanol for 22h; Heating;	92%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 2-amino-4-(trifluoromethyl)phenol (454-81-9) → 1-(5-(trifluoromethyl)benzo[d]oxazol-2-yl)thiourea

Conditions	Yield
In ethanol at 100℃; for 36h;	88%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → ((N,N-dimethylamino-methylidene)amino)-3H-1,2,4-dithiazoline-3-thione (1192027-04-5)

Conditions	Yield
In N,N-dimethyl-formamide at 20 - 25℃; for 5.5h;	84.5%
In N,N-dimethyl-formamide at 20℃; for 5h;	84.5%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 2-{benzyl [(4-methoxyphenyl)sulfonyl]amino}acetic acid (195052-28-9) → 2-{Benzyl[(4-methoxyphenyl)sulfonyl]amino}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl) acetoamide (500573-56-8)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 6h;	32%

2-{4-[(4-fluorobenzyl)oxy]phenyl}acetic acid (115882-26-3) + 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) → 2-{4-[(4-Fluorobenzyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (500573-60-4)

Conditions	Yield
With sodium hydride; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 4.5h;	29%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 2-{3,5-bis[(4-fluorobenzyl)oxy]phenyl}acetic acid

Conditions	Yield
With sodium hydride; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 8.5h;	22%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 2-(4-(octyloxy)phenyl)acetic acid (29148-14-9) → 2-[4-(Octyloxy)phenyl]-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (500573-61-5)

Conditions	Yield
With sodium hydride; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0℃; for 4.5h;	21%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 2,2-bis{4-[(4-fluorobenzyl)oxy]phenyl}acetic acid (500573-83-1) → 2,2-Bis{4-[(4-fluorobenzyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (500573-66-0)

Conditions	Yield
With sodium hydride; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 18.5h;	20%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy] phenyl}acetic acid → 2-{4-[(3,7-Dimethyl-2,6-octadienyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl) acetoamide

Conditions	Yield
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 3h;	18%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + formaldehyd (50-00-0) + benzylamine (100-46-9) → 6-benzyl-6,7-dihydro-5H-[1,2,4]dithiazolo[4,3-a]-[1,3,5]triazine-3-thione

Conditions	Yield
In ethanol; water; N,N-dimethyl-formamide for 0.05h; Reflux;	18%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + C17H17FO3 (1314762-05-4) → 2-{4-[(4-Fluorobenzyl)oxy]phenyl]-2-methyl-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl) propanamide (500573-68-2)

Conditions	Yield
With sodium hydride; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 17.5h;	17%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 2-{4-[(4-fluorobenzyl)oxy]phenyl}-3-methylbutanoic acid (500573-86-4) → 2-{4-[(4-Fluorobenzyl)oxy]phenyl}-3-methyl-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl) butanamide (500573-67-1)

Conditions	Yield
With sodium hydride; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 22.5h;	13%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + 3-{4-[(4-fluorobenzyl) oxy]phenyl} acrylic acid → 3-{4-[(4-fluorobenzyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acrylamide

Conditions	Yield
With sodium hydride; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 3.5h;	9%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + formaldehyd (50-00-0) + aniline (62-53-3) → 6-phenyl-6,7-dihydro-5H-[1,2,4]dithiazolo[4,3-a]-[1,3,5]triazine-3-thione

Conditions	Yield
With triethylamine In water; isopropyl alcohol for 0.05h; Reflux;	9%

2-{3-[(4-fluorobenzyl) oxy]phenyl}acetic acid (125721-49-5) + 5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) → 2-{3-[(4-Fluorobenzyl)oxy]phenyl}-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (500573-63-7)

Conditions	Yield
With sodium hydride; 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 14.5h;	6%

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + para-butoxyaniline (4344-55-2) → 1-(4-Butoxy-phenyl)-dithiobiuret

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + N-propylaniline (622-80-0) → 1-Phenyl-1-propyl-dithiobiuret

5-amino-3H-1,2,4-dithiazole-3-thione (6846-35-1) + N-(n-butyl)aniline (1126-78-9) → 1-Butyl-1-phenyl-dithiobiuret

Upstream product

• 333-20-0 potassium thioacyanate 
• 1147550-11-5 ammonium thiocyanate 
• 64-17-5 ethanol 
• 1858-23-7 phosphorus tri-isothiocyanate 
• 71-43-2 benzene 
• 13250-46-9 acetyl isothiocyanate 
• 1858-25-9 phosphoryl-isothiocyanate 
• 7732-18-5 water 
• 74237-96-0 trithioallophanic acid 
• 7664-93-9 sulfuric acid 
• 3129-90-6 isothiocyanic acid 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 17356-08-0 thiourea 
• 463-56-9 thiocyanic acid 

Downstream Products

• 7664-93-9 sulfuric acid 
• 7664-41-7 ammonia 
• 15719-64-9 methylammonium carbonate 
• 75-15-0 carbon disulfide 
• 7783-06-4 hydrogen sulfide 
• 17356-08-0 thiourea 
• 463-56-9 thiocyanic acid 
• 1147550-11-5 ammonium thiocyanate 
• 463-58-1 carbon oxide sulfide 
• 74-90-8 hydrogen cyanide 
• 124-38-9 carbon dioxide 
• 62530-07-8 2-thioureidobenzimidazole 
• 3878-45-3 triphenylphosphine sulfide 
• 1290605-38-7 2-[3-[[4-(Benzyloxy)benzyl]oxy]-5-methoxy-2-propylphenyl]-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide 

Relevant articles and documents

Design, synthesis andin silicoscreening of benzoxazole-thiazolidinone hybrids as potential inhibitors of SARS-CoV-2 proteases

Hybrid molecules in the recent years have gained significant importance in drug research as promising therapeutic agents. We report a novel combination of two such bioactive scaffolds (benzoxazole and 4-thiazolidinone B-T hybrids) as inhibitors of SARS-CoV-2. The study uses anin silicoapproach to identify the potential of B-T hybrids as possible inhibitors of the SARS-CoV-2 proteases. Molecular docking was employed to identify the interactions of B-T hybrids with the two proteases - 3CLp (the 3-chymotrypsin-like protease) and PLp (the papain-like protease). Docking results of the screened 81 hybrids indicated thatBT10andBT14interacted with the catalytic dyad residue of 3CLp (Cys145) with the best binding energy. MD simulations revealed thatBT10formed stable interactionsvia4 hydrogen bonds with the catalytic site residues of 3CLp. In the case of PLp,BT27andMBT9interacted with the catalytic triad residue of PLp (His272) with high binding energy. MD simulations demonstrated that the reference drug Tipranavir relocated to the thumb region of the protease whereasBT27remained in the active site of PLp stabilized by 2 hydrogen bonds, whileMBT9relocated to the BL2 loop of the palm region. The MM-PBSA and interaction entropy (IE) analysis indicated thatBT14exhibited the best ΔG(of ?6.83 kcal mol?1) with 3CLp, whileBT27exhibited the best ΔG(of ?7.76 kcal mol?1) with PLp. A four-step synthetic procedure was employed to synthesize the B-T hybrids starting from ammonium thiocyanate. The short-listed compounds in the case of 3CLp were synthesized and characterized using IR, NMR, and HRMS spectroscopic techniques.

Synthesis method of 5-amnio-1,2,4-dithiazole-3-thione

The invention belongs to the field of organic chemosynthesis, and particularly relates to a synthesis method of 5-amnio-1,2,4-dithiazole-3-thione. The invention aims at solving the technical problems that a synthesis method of the 5-amnio-1,2,4-dithiazole-3-thione is low in yield, poisonous gas can be generated to harm personal safety in a reaction process and plentiful strong acids used in a reaction needed to be subjected to waste disposal to consequently bring huge environmental protection pressure in the prior art. According to the scheme, for solving the technical problems, of the synthesis method, a condensation reaction is carried out by adopting S,S'-dimethyl dithiocarbonate and thiocarbamide as raw materials; afterwards, a reaction product is enabled to react with 2,3-dichloro-5,6-dicyanobenzoquinone, so that the 5-amnio-1,2,4-dithiazole-3-thione can be obtained. The synthesis method of the 5-amnio-1,2,4-dithiazole-3-thione, which is provided by the invention, is high in the yield, does not generate the poisonous gas, and does not generate a waste strong acid after the reaction.