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3179-31-5

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Basic Information
CAS No.: 3179-31-5
Name: 1H-1,2,4-Triazole-3-thiol
Molecular Structure:
Molecular Structure of 3179-31-5 (1H-1,2,4-Triazole-3-thiol)
Formula: C2H3N3S
Molecular Weight: 101.14
Synonyms: 4H-1,2,4-Triazole-3-thiol;4H-1,2, 4-Triazole-3-thiol;3-Mercapto-4H-1,2,4-triazole;1H-[1,2,4]-Triazole-3-thiol;3H-1,2, 4-Triazole-3-thione, 1,2-dihydro-;S-Triazole-3-thiol;5-Mercapto-1,3,4-triazole;3-Mercapto-1,2,4-triazole;1H-1,2, 4-Triazole-3-thiol;1,2, 4-Triazole-5-thiol;1,2,4-Triazole-3-thiol;3(5)-Mercapto-1,2, 4-triazole;2-Mercapto-1, 3,4-triazole;2-Mercapto-1,3,5-triazole;3-Mercapto-1H-1,2, 4-triazole;1,3, 4-Triazole-2-thiol;1,3,4-Triazine-2-thiol;1H-1,2,4-Triazole, 3-mercapto-;1,2-dihydro-1,2,4-triazole-3-thione;3-Mercapto-1,2,4-tiazole;3-Mercapto--1,2,4-triazole;3-mercapto-1h-1,2,4-triazole;1H-1,2,4-triazol-3-yl hydrosulfide;1H-1,2,4-triazol-3-yl hydrosulfide (IM OCS);
EINECS: 221-656-6
Density: 1.73 g/cm3
Melting Point: 221-224 °C(lit.)
Boiling Point: 132.6 °C at 760 mmHg
Flash Point: 34 °C
Solubility: Soluble in hot water.
Appearance: White to slightly yellow fine crystalline powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36-36/37/38
Safety: 26-33-39-7/8-37/39
Transport Information:
PSA: 80.37000
LogP: 0.09340
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Synthetic route
64-18-6

formic acid

79-19-6

thiosemicarbazide

3179-31-5

1H-[1,2,4]triazole-3-thiol

Conditions
ConditionsYield
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%
955942-82-2

2-amino-5-mercapto-s-triazole

3179-31-5

1H-[1,2,4]triazole-3-thiol

Conditions
ConditionsYield
H14[NaP5W30O110] In acetic acid for 24h; Heating;57%
79-19-6

thiosemicarbazide

N-Methyl-thioformimidic acid benzyl ester; hydrochloride

3179-31-5

1H-[1,2,4]triazole-3-thiol

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 3h; Heating;55%
2302-84-3

1-formylthiosemicarbazide

3179-31-5

1H-[1,2,4]triazole-3-thiol

Conditions
ConditionsYield
With sodium carbonate In water at 20 - 100℃; for 4h;55%
30093-97-1

3,4,4-trimethyl-Δ2-oxazolinium iodide

79-19-6

thiosemicarbazide

3179-31-5

1H-[1,2,4]triazole-3-thiol

Conditions
ConditionsYield
In acetonitrile for 75h; Heating;50%
79-19-6

thiosemicarbazide

90965-27-8

Δ2-thiazolinium bromide

3179-31-5

1H-[1,2,4]triazole-3-thiol

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 3h; Heating;50%
41030-51-7

1-ethoxymethylene thiosemicarbazide

aqueous sodium carbonate

aqueous sodium carbonate

3179-31-5

1H-[1,2,4]triazole-3-thiol

1-formyl-3-thiosemicarbazide

3179-31-5

1H-[1,2,4]triazole-3-thiol

Conditions
ConditionsYield
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
111952-57-9

3-[(3-chloropropyl)oxy]benzonitrile

3179-31-5

1H-[1,2,4]triazole-3-thiol

935760-05-7

3-{[3-(1H-1,2,4-triazol-3-ylthio)propyl]oxy}benzonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 80℃; for 15h;100%
928257-12-9

3-[(4-chlorobutyl)oxy]benzonitrile

3179-31-5

1H-[1,2,4]triazole-3-thiol

935760-08-0

3-{[4-(1H-1,2,4-triazol-3-ylthio)butyl]oxy}benzonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 80℃; for 15h;100%
3179-31-5

1H-[1,2,4]triazole-3-thiol

824-94-2

p-methoxybenzyl chloride

3-((4-methoxybenzyl)thio)-1H-1,2,4-triazole

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

C20H36Au4N4O12S4

584-08-7

potassium carbonate

3179-31-5

1H-[1,2,4]triazole-3-thiol

potassium hydroxide

C7H9AuN4O3S2(1-)*K(1+)

Conditions
ConditionsYield
In water at 60℃;100%
...Expand
3179-31-5

1H-[1,2,4]triazole-3-thiol

97315-37-2

3-[(2-chloroethyl)oxy]benzonitrile

935760-03-5

3-{[2-(1H-1,2,4-triazol-3-ylthio)ethyl]oxy}benzonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 80℃; for 15h;98%
With triethylamine In ethanol at 80℃; for 15h;98%
1242147-88-1

(E)-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide

3179-31-5

1H-[1,2,4]triazole-3-thiol

881943-78-8

N-(3-(1H-1,2,4-triazol-5-ylthio)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2h;96.5%
73017-76-2

methanesulfonic acid cyclopentylmethyl ester

3179-31-5

1H-[1,2,4]triazole-3-thiol

cyclopentylmethyl 1,2,4-triazol-3-yl sulfide

Conditions
ConditionsYield
With potassium hydroxide In methanol96%
3179-31-5

1H-[1,2,4]triazole-3-thiol

14804-01-4

3-(1H-1,2,4-triazol-3-yldisulfanyl)-1H-1,2,4-triazole

Conditions
ConditionsYield
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%
3179-31-5

1H-[1,2,4]triazole-3-thiol

931-59-9

benzenesulfenyl chloride

3-(phenyldisulfanyl)-1H-1,2,4-triazole

Conditions
ConditionsYield
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

3179-31-5

1H-[1,2,4]triazole-3-thiol

Boc-Phe-ΔCys(S-triazole)-OMe

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

C11H17BrN2O4

3179-31-5

1H-[1,2,4]triazole-3-thiol

Boc-Gly-ΔCys(S-triazole)-OMe

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃;93%
3179-31-5

1H-[1,2,4]triazole-3-thiol

14867-28-8

3-iodopropyltrimethoxysilane

3-[3-(trimethoxysilyl)propylthio]-1H-1,2,4-triazole

Conditions
ConditionsYield
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%
3179-31-5

1H-[1,2,4]triazole-3-thiol

488-17-5

3-methylbenzene-1,2-diol

5-(1H-1,2,4-triazol-3-ylthio)-3-methylbenzen-1,2-diol

Conditions
ConditionsYield
In acetate buffer; acetonitrile Electrochemical reaction;92%
934-00-9

3-methocycatechol

3179-31-5

1H-[1,2,4]triazole-3-thiol

5-(1H-1,2,4-triazol-3-ylthio)-3-methoxybenzen-1,2-diol

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

N-[4-(4-piperidinomethyl-pyridin-2-yloxy)-cis-2-butenyl]-2-chloroacetamide

3179-31-5

1H-[1,2,4]triazole-3-thiol

N-[4-(4-Piperidinomethyl-pyridin-2-yloxy)-cis-2-butenyl]-2-(1,2,4-triazol-3-ylthio)acetamide

Conditions
ConditionsYield
91%
88-67-5

2-Iodobenzoic acid

3179-31-5

1H-[1,2,4]triazole-3-thiol

122604-23-3

1,2,4-Triazolo<5,1-b><1,3>benzothiazin-9-one

Conditions
ConditionsYield
With potassium carbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 80℃; for 24h; Sealed tube; Schlenk technique;91%
6959-48-4

3-chloromethylpyridinium chloride

3179-31-5

1H-[1,2,4]triazole-3-thiol

3-(3-pyridylmethylsulfanyl)-1H-1,2,4-triazole

Conditions
ConditionsYield
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%
3179-31-5

1H-[1,2,4]triazole-3-thiol

(4-nitrophenyl) 2,3-dibromopropyl sulfone

6-(4-nitrophenylsulfonylmethyl)-5,6-dihydro[1,3]thiazolo[3,2-c][1,2,4]triazole

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 8h;90%
3179-31-5

1H-[1,2,4]triazole-3-thiol

13360-57-1

dimethylamino sulfonyl chloride

247236-09-5

3-{[1-(dimethylsulfamoyl)-1H-1,2,4-triazol-3-yl]disulfanyl}-N,N-dimethyl-1H-1,2,4-triazole-1-sulfonamide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 28 - 32℃; for 8h;90%
3179-31-5

1H-[1,2,4]triazole-3-thiol

99-73-0

para-bromophenacyl bromide

37664-32-7

2-(1H-1,2,4-triazol-3-ylthio)-1-(4-bromophenyl) ethanone

Conditions
ConditionsYield
In ethanol at 20℃; for 14h; Reflux;89%
52548-14-8

2-iodoyl-5-methylbenzoic acid

3179-31-5

1H-[1,2,4]triazole-3-thiol

7-methyl-9H-[1,2,4]triazolo[5,1-b][1,3]benzothiazin-9-one

Conditions
ConditionsYield
With potassium carbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 80℃; for 24h; Sealed tube; Schlenk technique;89%
3179-31-5

1H-[1,2,4]triazole-3-thiol

86-52-2

1-Chloromethylnaphthalene

3-(1-naphthylmethylsulfanyl)-1H-1,2,4-triazole

Conditions
ConditionsYield
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%
3179-31-5

1H-[1,2,4]triazole-3-thiol

75-65-0

tert-butyl alcohol

1380786-15-1

3-tert-butylsulfanyl-1,2,4-triazole

Conditions
ConditionsYield
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%
3179-31-5

1H-[1,2,4]triazole-3-thiol

88-05-1

2,4,6-trimethylaniline

158091-64-6

3-(2,4,6-trimethylphenyl)thio-1H-1,2,4-triazole

Conditions
ConditionsYield
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;
3179-31-5

1H-[1,2,4]triazole-3-thiol

104-82-5

4-Methylbenzyl chloride

3-((4-methylbenzyl)thio)-1H-1,2,4-triazole

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 75℃; for 0.333333h;86%
With sodium hydroxide In ethanol; water for 0.333333h; Reflux;
807342-38-7

2-naphthyl 2,3-dibromopropyl sulfone

3179-31-5

1H-[1,2,4]triazole-3-thiol

6-(2-naphthylsulfonylmethyl)-5,6-dihydro[1,3]thiazolo[3,2-c][1,2,4]triazole

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

Na2[Fe2(μ2-thiosulfate)2(nitrosyl)4]*2H2O

3179-31-5

1H-[1,2,4]triazole-3-thiol

bis(μ2-1,2,4-triazole-3-thiolate)(tetranitrosyl)diironmonohydrate

Conditions
ConditionsYield
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]

3179-31-5

1H-[1,2,4]triazole-3-thiol

bis(μ2-1,2,4-triazole-3-thiolate)(tetranitrosyl)diironmonohydrate

Conditions
ConditionsYield
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%
1402547-89-0

1-(12-bromododec-5(Z)-enyl)-3-n-pentylurea

3179-31-5

1H-[1,2,4]triazole-3-thiol

1402547-56-1

C20H37N5OS

Conditions
ConditionsYield
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%
111128-12-2

2-(4-(bromomethyl)phenyl)propanoic acid

3179-31-5

1H-[1,2,4]triazole-3-thiol

2-(4-(((1H-1,2,4-triazol-3-yl)thio)methyl)phenyl)propanoic acid

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

Molecular structure of 1H-1,2,4-Triazole-3-thiol (CAS NO.3179-31-5) is:

Product Name: 1H-1,2,4-Triazole-3-thiol
CAS Registry Number: 3179-31-5
IUPAC Name: 1,2-dihydro-1,2,4-triazole-3-thione
Molecular Weight: 101.13032 [g/mol]
Molecular Formula: C2H3N3S
XLogP3-AA: -0.2
H-Bond Donor: 2
H-Bond Acceptor: 1 
EINECS: 221-656-6
Melting Point: 221-224 °C(lit.)
Surface Tension: 63.4 dyne/cm
Density: 1.73 g/cm3
Flash Point: 52.3 °C
Enthalpy of Vaporization: 38.29 kJ/mol
Boiling Point: 162.8 °C at 760 mmHg
Vapour Pressure: 2.78 mmHg at 25°C

Uses

 1H-1,2,4-Triazole-3-thiol (CAS NO.3179-31-5) is used as a pharmaceutical intermediate.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1400mg/kg (1400mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 284, 1971.
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03630,

Safety Profile

Hazard Codes: HarmfulXn,Xi
Risk Statements: 22-36-36/37/38 
R22:Harmful if swallowed. 
R36:Irritating to eyes. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-33-39-7/8-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S33:Take precautionary measures against static discharges. 
S39:Wear eye / face protection. 
S7:Keep container tightly closed and dry. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 1
RTECS: XZ5267500
F: 10-23
Hazard Note: Irritant
HS Code: 29339990

Specification

 1H-1,2,4-Triazole-3-thiol , its cas register number is 3179-31-5. It also can be called 1,2,4-Triazole-3(5)-thiol ; 3-Mercapto-1H-1,2,4-triazole ; 1,2,4-Triazole-3-thiol ; 1,2-Dihydro-3H-1,2,4-triazole-3-thione ; 1H-1,2,4-Triazole-3-thiol ; 3H-1,2,4-Triazole-3-thione, 1,2-dihydro- ; delta2-1,2,4-Triazoline-5-thione (8CI) .It is a white solid with a stench.It very soluble in water.