3179-31-5

Basic information

• Product Name: 1H-1,2,4-Triazole-3-thiol
• Synonyms: 4-triazole,3-mercapto-1h-2;4-triazole-3-thione,1,2-dihydro-3h-2;ent61291;1,2,4-triazole-3(5)-thiol;1,2,4-TRIAZOLE-3-THIOL;1H-1,2,4-TRIAZOLE-3-MERCAPTAN;1H-1,2,4-TRIAZOLE-3-THIOL;1H-1,2,4-TRIAZOLO-3-MERCAPTAN
• CAS NO: 3179-31-5
• Molecular Formula: C₂H₃N₃S
• Molecular Weight: 101.13
• EINECS: 221-656-6
• Mol File: 3179-31-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: 221-224 °C(lit.)
• Boiling Point: 132.6 °C at 760 mmHg
• Flash Point: 34 °C
• Appearance: /solid
• Density: 1.385 (estimate)
• Vapor Pressure: 2.78mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: soluble50g/L
• PKA: 9.24±0.20(Predicted)
• Water Solubility: Soluble in hot water.
• BRN: 107731
• CAS DataBase Reference: 1H-1,2,4-Triazole-3-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1,2,4-Triazole-3-thiol(3179-31-5)
• EPA Substance Registry System: 1H-1,2,4-Triazole-3-thiol(3179-31-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36-36/37/38
• Safety Statements: 26-33-39-7/8-37/39
• WGK Germany: 1
• RTECS: XZ5267500
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 3179-31-5(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO SLIGHTLY YELLOW FINE CRYSTALLINE POWDER

Uses

1H-1,2,4-Triazole-3-thiol was used in a study to design a surface enhanced Raman scattering based probe for fast and accurate detection of DNA markers.

General Description

1H-1,2,4-Triazole-3-thiol is a mercapto-substituted 1,2,4-triazole ligand and exhibits tautomerism in solution. 1H-1,2,4-Triazole-3-thiol forms novel luminescent polymers with cadmium(II) salts. 1H-1,2,4-Triazole-3-thiol undergoes regioselective S-alkylation to form a series of S-substituted derivatives.

InChI:InChI=1/C2H3N3S/c6-2-3-1-4-5-2/h1-2,6H

Synthetic route

formic acid (64-18-6) + thiosemicarbazide (79-19-6) → 1H-[1,2,4]triazole-3-thiol (3179-31-5)

Conditions	Yield
Stage #1: formic acid; thiosemicarbazide In water at 100℃; for 1h; Stage #2: With potassium carbonate In water at 110℃; for 3h;	65%
Stage #1: formic acid; thiosemicarbazide In water at -10 - 105℃; Stage #2: With sodium carbonate In water at 100℃; for 4h;	55%

2-amino-5-mercapto-s-triazole (955942-82-2) → 1H-[1,2,4]triazole-3-thiol (3179-31-5)

Conditions	Yield
H14[NaP5W30O110] In acetic acid for 24h; Heating;	57%

thiosemicarbazide (79-19-6) + N-Methyl-thioformimidic acid benzyl ester; hydrochloride → 1H-[1,2,4]triazole-3-thiol (3179-31-5)

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Heating;	55%

1-formylthiosemicarbazide (2302-84-3) → 1H-[1,2,4]triazole-3-thiol (3179-31-5)

Conditions	Yield
With sodium carbonate In water at 20 - 100℃; for 4h;	55%

3,4,4-trimethyl-Δ2-oxazolinium iodide (30093-97-1) + thiosemicarbazide (79-19-6) → 1H-[1,2,4]triazole-3-thiol (3179-31-5)

Conditions	Yield
In acetonitrile for 75h; Heating;	50%

thiosemicarbazide (79-19-6) + Δ2-thiazolinium bromide (90965-27-8) → 1H-[1,2,4]triazole-3-thiol (3179-31-5)

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Heating;	50%

1-ethoxymethylene thiosemicarbazide (41030-51-7) + aqueous sodium carbonate → 1H-[1,2,4]triazole-3-thiol (3179-31-5)

1-formyl-3-thiosemicarbazide → 1H-[1,2,4]triazole-3-thiol (3179-31-5)

Conditions	Yield
Stage #1: 1-formyl-3-thiosemicarbazide With potassium carbonate In water at 100℃; for 4h; Stage #2: With hydrogenchloride In water at -10℃; pH=4 - 5;	5.6 g

3-[(3-chloropropyl)oxy]benzonitrile (111952-57-9) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → 3-{[3-(1H-1,2,4-triazol-3-ylthio)propyl]oxy}benzonitrile (935760-05-7)

Conditions	Yield
With triethylamine In ethanol at 80℃; for 15h;	100%

3-[(4-chlorobutyl)oxy]benzonitrile (928257-12-9) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → 3-{[4-(1H-1,2,4-triazol-3-ylthio)butyl]oxy}benzonitrile (935760-08-0)

Conditions	Yield
With triethylamine In ethanol at 80℃; for 15h;	100%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + p-methoxybenzyl chloride (824-94-2) → 3-((4-methoxybenzyl)thio)-1H-1,2,4-triazole

Conditions	Yield
In ethanol at 20℃; for 3h;	100%

C20H36Au4N4O12S4 + potassium carbonate (584-08-7) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) + potassium hydroxide → C7H9AuN4O3S2(1-)*K(1+)

Conditions	Yield
In water at 60℃;	100%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + 3-[(2-chloroethyl)oxy]benzonitrile (97315-37-2) → 3-{[2-(1H-1,2,4-triazol-3-ylthio)ethyl]oxy}benzonitrile (935760-03-5)

Conditions	Yield
With triethylamine In ethanol at 80℃; for 15h;	98%
With triethylamine In ethanol at 80℃; for 15h;	98%

(E)-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (1242147-88-1) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → N-(3-(1H-1,2,4-triazol-5-ylthio)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (881943-78-8)

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h;	96.5%

methanesulfonic acid cyclopentylmethyl ester (73017-76-2) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → cyclopentylmethyl 1,2,4-triazol-3-yl sulfide

Conditions	Yield
With potassium hydroxide In methanol	96%

1H-[1,2,4]triazole-3-thiol (3179-31-5) → 3-(1H-1,2,4-triazol-3-yldisulfanyl)-1H-1,2,4-triazole (14804-01-4)

Conditions	Yield
With pyridine; benzenesulfonyl chloride In dichloromethane at 0 - 25℃; for 20h;	95.2%
With pyridine; p-toluenesulfonyl chloride In dichloromethane at 0 - 25℃; for 20h;	95.2%
With pyridine; benzenesulfonyl chloride In dichloromethane at 0 - 25℃; for 20h;	95.2%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + benzenesulfenyl chloride (931-59-9) → 3-(phenyldisulfanyl)-1H-1,2,4-triazole

Conditions	Yield
In diethyl ether at 20℃; for 5h;	94%
With triethylamine In tetrahydrofuran at 20℃; for 2.5h; Cooling with ice;	45%
With water; triethylamine In tetrahydrofuran at 20℃;

C18H23BrN2O4 + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → Boc-Phe-ΔCys(S-triazole)-OMe

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	94%

C11H17BrN2O4 + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → Boc-Gly-ΔCys(S-triazole)-OMe

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	93%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + 3-iodopropyltrimethoxysilane (14867-28-8) → 3-[3-(trimethoxysilyl)propylthio]-1H-1,2,4-triazole

Conditions	Yield
Stage #1: 1H-[1,2,4]triazole-3-thiol With sodium methylate In methanol at 10 - 20℃; for 0.5h; Stage #2: 3-iodopropyltrimethoxysilane In methanol at 27 - 30℃; for 3.66667h;	92.3%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + 3-methylbenzene-1,2-diol (488-17-5) → 5-(1H-1,2,4-triazol-3-ylthio)-3-methylbenzen-1,2-diol

Conditions	Yield
In acetate buffer; acetonitrile Electrochemical reaction;	92%

3-methocycatechol (934-00-9) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → 5-(1H-1,2,4-triazol-3-ylthio)-3-methoxybenzen-1,2-diol

Conditions	Yield
In acetate buffer; acetonitrile Electrochemical reaction;	91%

N-[4-(4-piperidinomethyl-pyridin-2-yloxy)-cis-2-butenyl]-2-chloroacetamide + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → N-[4-(4-Piperidinomethyl-pyridin-2-yloxy)-cis-2-butenyl]-2-(1,2,4-triazol-3-ylthio)acetamide

Conditions	Yield
	91%

2-Iodobenzoic acid (88-67-5) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → 1,2,4-Triazolo<5,1-b><1,3>benzothiazin-9-one (122604-23-3)

Conditions	Yield
With potassium carbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 80℃; for 24h; Sealed tube; Schlenk technique;	91%

3-chloromethylpyridinium chloride (6959-48-4) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → 3-(3-pyridylmethylsulfanyl)-1H-1,2,4-triazole

Conditions	Yield
Stage #1: 1H-[1,2,4]triazole-3-thiol With sodium In methanol; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 3-chloromethylpyridinium chloride In methanol; N,N-dimethyl-formamide at 20℃;	90%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + (4-nitrophenyl) 2,3-dibromopropyl sulfone → 6-(4-nitrophenylsulfonylmethyl)-5,6-dihydro[1,3]thiazolo[3,2-c][1,2,4]triazole

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 8h;	90%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + dimethylamino sulfonyl chloride (13360-57-1) → 3-{[1-(dimethylsulfamoyl)-1H-1,2,4-triazol-3-yl]disulfanyl}-N,N-dimethyl-1H-1,2,4-triazole-1-sulfonamide (247236-09-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 28 - 32℃; for 8h;	90%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + para-bromophenacyl bromide (99-73-0) → 2-(1H-1,2,4-triazol-3-ylthio)-1-(4-bromophenyl) ethanone (37664-32-7)

Conditions	Yield
In ethanol at 20℃; for 14h; Reflux;	89%

2-iodoyl-5-methylbenzoic acid (52548-14-8) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → 7-methyl-9H-[1,2,4]triazolo[5,1-b][1,3]benzothiazin-9-one

Conditions	Yield
With potassium carbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 80℃; for 24h; Sealed tube; Schlenk technique;	89%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + 1-Chloromethylnaphthalene (86-52-2) → 3-(1-naphthylmethylsulfanyl)-1H-1,2,4-triazole

Conditions	Yield
Stage #1: 1H-[1,2,4]triazole-3-thiol With sodium In methanol; N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 1-Chloromethylnaphthalene In methanol; N,N-dimethyl-formamide at 20℃;	88%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + tert-butyl alcohol (75-65-0) → 3-tert-butylsulfanyl-1,2,4-triazole (1380786-15-1)

Conditions	Yield
Stage #1: 1H-[1,2,4]triazole-3-thiol; tert-butyl alcohol With perchloric acid In water at 20℃; for 3h; Stage #2: With sodium hydroxide In water pH=6 - 7; regioselective reaction;	87%

1H-[1,2,4]triazole-3-thiol (3179-31-5) + 2,4,6-trimethylaniline (88-05-1) → 3-(2,4,6-trimethylphenyl)thio-1H-1,2,4-triazole (158091-64-6)

Conditions	Yield
Stage #1: 2,4,6-trimethylaniline With hydrogenchloride; sodium nitrite In water at 10℃; for 0.00277778h; Flow reactor; Stage #2: 1H-[1,2,4]triazole-3-thiol With sodium hydroxide In methanol; n-heptane; water at 25℃; under 7498.84 Torr; for 0.0111111h; Flow reactor;	86%
Stage #1: 2,4,6-trimethylaniline With hydrogenchloride; sodium nitrite In water at -5 - -2℃; for 0.5h; Large scale; Stage #2: 1H-[1,2,4]triazole-3-thiol With sodium hydroxide In methanol; water at 20 - 30℃; for 1.16667h; Temperature; Solvent; Large scale;	60%
Stage #1: 2,4,6-trimethylaniline With hydrogenchloride; sodium nitrite In methanol; water for 0.5h; Cooling with ice/sodium chloride; Stage #2: 1H-[1,2,4]triazole-3-thiol With potassium hydroxide In methanol; water at 20℃; for 1.5h; Cooling with ice/sodium chloride;

1H-[1,2,4]triazole-3-thiol (3179-31-5) + 4-Methylbenzyl chloride (104-82-5) → 3-((4-methylbenzyl)thio)-1H-1,2,4-triazole

Conditions	Yield
With sodium hydroxide In ethanol at 75℃; for 0.333333h;	86%
With sodium hydroxide In ethanol; water for 0.333333h; Reflux;

2-naphthyl 2,3-dibromopropyl sulfone (807342-38-7) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → 6-(2-naphthylsulfonylmethyl)-5,6-dihydro[1,3]thiazolo[3,2-c][1,2,4]triazole

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 8h;	85%

Na2[Fe2(μ2-thiosulfate)2(nitrosyl)4]*2H2O + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → bis(μ2-1,2,4-triazole-3-thiolate)(tetranitrosyl)diironmonohydrate

Conditions	Yield
With Na2S2O3*5H2O; NaOH In water addn. of an alkaline soln. of ligand to an aq. soln. of iron complex, storage at 6-8°C for 6 d; recrystn. (methanol); elem. anal.;	85%

Na2[Fe2(μ2-S2O3)2(NO)4] + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → bis(μ2-1,2,4-triazole-3-thiolate)(tetranitrosyl)diironmonohydrate

Conditions	Yield
With Na2S2O3*5H2O In water 5 equiv. of thiole was dissolved in aq. alkali and added to an aq. mixt.of Fe-compd. and 2 equiv. of Na2S2O3; soln. was filtered and storaged at 6-8 °C for a few days, recrystn. from abs. MeOH, drying in vac. over CaCl2, elem. anal.;	85%

1-(12-bromododec-5(Z)-enyl)-3-n-pentylurea (1402547-89-0) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → C20H37N5OS (1402547-56-1)

Conditions	Yield
Stage #1: 1H-[1,2,4]triazole-3-thiol With sodium methylate In methanol; N,N-dimethyl-formamide for 0.166667h; Stage #2: 1-(12-bromododec-5(Z)-enyl)-3-n-pentylurea In methanol; N,N-dimethyl-formamide	85%
Stage #1: 1H-[1,2,4]triazole-3-thiol With sodium methylate In N,N-dimethyl-formamide for 0.166667h; Stage #2: 1-(12-bromododec-5(Z)-enyl)-3-n-pentylurea In N,N-dimethyl-formamide	85%

2-(4-(bromomethyl)phenyl)propanoic acid (111128-12-2) + 1H-[1,2,4]triazole-3-thiol (3179-31-5) → 2-(4-(((1H-1,2,4-triazol-3-yl)thio)methyl)phenyl)propanoic acid

Conditions	Yield
In acetone at 40℃; for 12h; Reflux;	85%

Upstream product

• 290-87-9 1,3,5-Triazine 
• 79-19-6 thiosemicarbazide 
• 2302-84-3 1-formylthiosemicarbazide 
• 288-88-0 1,2,4-Triazole 
• 90965-28-9 4,4-dimethyl-Δ²-oxazolinium chloride 
• 90965-27-8 Δ²-thiazolinium bromide 
• 30093-97-1 3,4,4-trimethyl-Δ²-oxazolinium iodide 
• 537698-46-7 2-cyanoethyl-1,2,4-triazole-3(2H)-thione 
• 64-18-6 formic acid 
• 955942-82-2 2-amino-5-mercapto-s-triazole 
• 41030-51-7 1-ethoxymethylene thiosemicarbazide 
• 4005-51-0 [1,3,4]Thiadiazol-2-ylamin 
• 67-56-1 methanol 
• 74-89-5 methylamine 

Downstream Products

• 288-88-0 1,2,4-Triazole 
• 73768-81-7 (Nitro-5 pyridyl-2) (triazolyl-3) thioaether 
• 73768-81-7 5-Nitro-2-(4H-[1,2,4]triazol-3-ylsulfanyl)-pyridine 
• 73768-80-6 (3-nitro-2-pyridyl)-3-thio-1,2,4-triazole 
• 83749-83-1 5-imino-7-phenyl-1,2,4-triazolo<3,2-b>-1,3-thiazine 
• 83749-85-3 2-(1-phenyl-2-cyanovinylene)-3-<(1-phenyl-2-cyanovinylene)thiol>-1,2,4-triazole 
• 24127-59-1 (1,2,4-triazol-5-ylthio)acetic acid methyl ester 
• 186787-42-8 2-(4-Methanesulfonyl-phenyl)-1-phenyl-2-(4H-[1,2,4]triazol-3-ylsulfanyl)-ethanone 
• 186787-43-9 1-(4-Methanesulfonyl-phenyl)-2-phenyl-2-(4H-[1,2,4]triazol-3-ylsulfanyl)-ethanone 

Relevant articles and documents

Deamination of some N-amino nitrogen heterocycles using Preyssler's anion

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Discovery of a new fungicide by screening triazole sulfonylhydrazone derivatives and its downy mildew inhibition in cucumber

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