Product Name

  • Name

    5-Mercapto-1-methyltetrazole

  • EINECS 236-132-2
  • CAS No. 13183-79-4
  • Article Data25
  • CAS DataBase
  • Density 1.69 g/cm3
  • Solubility
  • Melting Point 125-128 °C(lit.)
  • Formula C2H4N4S
  • Boiling Point 111.6 °C at 760 mmHg
  • Molecular Weight 116.147
  • Flash Point 21.3 °C
  • Transport Information
  • Appearance white crystalline powder
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 13183-79-4 (5-Mercapto-1-methyltetrazole)
  • Hazard Symbols IrritantXi
  • Synonyms 1,2,3,4-Tetrazole-5-thiol,1-methyl- (4CI);1H-Tetrazole-5-thiol, 1-methyl- (7CI,8CI);1,2-Dihydro-1-methyl-5H-tetrazole-5-thione;1-Methyl-1,2,3,4-tetrazoline-5-thione;1-Methyl-5-mercapto-1,2,3,4-tetrazole;1-Methyl-5-mercapto-1H-tetrazole;1-Methyl-5-tetrazolethione;1-Methyl-5-thiotetrazole;5-Mercapto-1-methyl-1,2,3,4-tetrazole;[1-Methyl-1H-1H-tetrazol-5-yl]thiol;5H-Tetrazole-5-thione,1,2-dihydro-1-methyl-;
  • PSA 82.40000
  • LogP -0.50120

Synthetic route

methyl thioisocyanate
556-61-6

methyl thioisocyanate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

Conditions
ConditionsYield
With sodium azide In ethanol; water at 30 - 70℃; for 2h; Temperature; Microwave irradiation;97%
With sodium azide In ethanol at 70℃; for 3h; Cyclization;
With sodium azide for 6h; Reflux;
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

Conditions
ConditionsYield
With sodium azide; sodium hydroxide In water at 95℃; for 14h; Temperature;93.6%
C4H6Cl2N2S2

C4H6Cl2N2S2

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

Conditions
ConditionsYield
With sodium azide In ethanol; water at 20 - 50℃; for 2.5h;93.1%
bis (1-methyl-(1H)-tetrazol-5-yl)-disulfide
62671-38-9

bis (1-methyl-(1H)-tetrazol-5-yl)-disulfide

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

Conditions
ConditionsYield
With hydrazine In dichloromethane for 0.25h; Ambient temperature; further reagents;93%
4-methylthiosemicarbazide
6610-29-3

4-methylthiosemicarbazide

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

Conditions
ConditionsYield
Stage #1: 4-methylthiosemicarbazide With triethylamine In N,N-dimethyl-formamide; acetonitrile at 5℃; for 0.5h; Cooling with ice;
Stage #2: With n-Butyl nitrite In N,N-dimethyl-formamide; acetonitrile at 60 - 65℃; for 1h;		63%
bis (1-methyl-(1H)-tetrazol-5-yl)-disulfide
62671-38-9

bis (1-methyl-(1H)-tetrazol-5-yl)-disulfide

diluted NaOH-solution

diluted NaOH-solution

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

2-pivaloyloxymethylfuran

2-pivaloyloxymethylfuran

5-(furan-2-ylmethylthio)-1-methyl-1H-tetrazole

5-(furan-2-ylmethylthio)-1-methyl-1H-tetrazole

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 80℃; for 0.5h;100%
thiophen-2-ylmethyl pivalate

thiophen-2-ylmethyl pivalate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

1-methyl-5-(thiophen-2-ylmethylthio)-1H-tetrazole

1-methyl-5-(thiophen-2-ylmethylthio)-1H-tetrazole

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 80℃; for 0.5h;100%
C20H36Au4N4O12S4

C20H36Au4N4O12S4

potassium carbonate
584-08-7

potassium carbonate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

potassium hydroxide

potassium hydroxide

C7H10AuN5O3S2(1-)*K(1+)

C7H10AuN5O3S2(1-)*K(1+)

Conditions
ConditionsYield
In water at 20 - 80℃; for 3h;100%
...Expand
1-iodo-3-phenylpropan
4119-41-9

1-iodo-3-phenylpropan

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

C11H14N4S

C11H14N4S

Conditions
ConditionsYield
In 1,4-dioxane at 110℃; for 0.25h;99%
1-naphthylmethyl 2,2-dimethylpropanoate
72681-59-5

1-naphthylmethyl 2,2-dimethylpropanoate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

1-methyl-5-(naphthalen-1-ylmethylthio)-1H-tetrazole

1-methyl-5-(naphthalen-1-ylmethylthio)-1H-tetrazole

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 80℃; for 0.5h;99%
(E)-3-(4-methoxyphenyl)allyl pivalate
1014394-72-9

(E)-3-(4-methoxyphenyl)allyl pivalate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

(E)-5-(3-(4-methoxyphenyl)allylthio)-1-methyl-1H-tetrazole

(E)-5-(3-(4-methoxyphenyl)allylthio)-1-methyl-1H-tetrazole

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 80℃; for 0.5h;99%
C18H20O2

C18H20O2

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

(E)-1-methyl-5-(3-(naphthalen-1-yl)allylthio)-1H-tetrazole

(E)-1-methyl-5-(3-(naphthalen-1-yl)allylthio)-1H-tetrazole

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 80℃; for 1h;99%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

1-methyl-4-(tetrahydrofuran-2-yl)-1H-tetrazole-5(4H)-thione

1-methyl-4-(tetrahydrofuran-2-yl)-1H-tetrazole-5(4H)-thione

Conditions
ConditionsYield
In tetrahydrofuran at 65℃; for 2h;99%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

1-benzhydryl-4-methyl-1,4-dihydro-5H-tetrazole-5-thione

1-benzhydryl-4-methyl-1,4-dihydro-5H-tetrazole-5-thione

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane at 85℃; Sealed tube; chemoselective reaction;99%
1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

7-Aminocephalosporanic acid
957-68-6

7-Aminocephalosporanic acid

(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid
24209-38-9

(6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: 1-methyl-5-mercaptotetrazole With boron trifluoride dimethyl carbonate complex; carbonic acid dimethyl ester at 10 - 12℃; for 0.166667h;
Stage #2: 7-Aminocephalosporanic acid at 25℃; for 0.75h;
Stage #3: With chloroacetyl chloride In N,N-dimethyl-formamide at 0℃; for 0.75h;		98%
With pyridine; tetrabutoxytitanium; titanium tetrachloride In acetonitrile at 5 - 30℃; for 3h; Reagent/catalyst;98%
With boron trifluoride In acetonitrile at 30℃; for 1.5h;94.7%
iodobenzene
591-50-4

iodobenzene

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

1-methyl-5-phenylthio-1,2,3,4-tetrazole

1-methyl-5-phenylthio-1,2,3,4-tetrazole

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 10h;98%
With potassium phosphate; copper In dimethyl sulfoxide at 100℃; for 24h;84%
1-methyl-3-ethylimidazolium hydrogen carbonate

1-methyl-3-ethylimidazolium hydrogen carbonate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

1-methyl-5-mercapto-1,2,3,4-tetrazole 1-methyl-3-ethylimidazolium salt

1-methyl-5-mercapto-1,2,3,4-tetrazole 1-methyl-3-ethylimidazolium salt

Conditions
ConditionsYield
In methanol for 3h;98%
1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

edaravone
89-25-8

edaravone

3-methyl-4-((1-methyl-1H-tetrazol-5-yl)thio)-1-phenyl-1H-pyrazol-5-ol

3-methyl-4-((1-methyl-1H-tetrazol-5-yl)thio)-1-phenyl-1H-pyrazol-5-ol

Conditions
ConditionsYield
With 5-ethyl-1,3,7,8-tetramethylalloxazinium triflate; iodine In acetonitrile at 25℃; under 760.051 Torr; for 24h; Green chemistry; chemoselective reaction;98%
With iodine In dimethyl sulfoxide at 80℃; for 1.5h; Green chemistry;88%
1-ethenyl-4-methylbenzene
622-97-9

1-ethenyl-4-methylbenzene

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

1-methyl-5-((1-(p-tolyl)ethyl)thio)-1H-tetrazole

1-methyl-5-((1-(p-tolyl)ethyl)thio)-1H-tetrazole

Conditions
ConditionsYield
With palladium diacetate; copper(II) bis(trifluoromethanesulfonate) In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 4h; Inert atmosphere;97%
(E)-4-(4-fluorophenyl)but-3-en-2-ol
1092986-09-8

(E)-4-(4-fluorophenyl)but-3-en-2-ol

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

(E)-1-(4-(4-fluorophenyl)but-3-en-2-yl)-4-methyl-1,4-dihydro-5H-tetrazole-5-thione

(E)-1-(4-(4-fluorophenyl)but-3-en-2-yl)-4-methyl-1,4-dihydro-5H-tetrazole-5-thione

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane at 85℃; Sealed tube; chemoselective reaction;97%
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

1-naphthaldehyde
66-77-3

1-naphthaldehyde

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

1-methyl-4-(naphthalen-1-yl(2,4,6-trimethoxyphenyl)methyl)-1,4-dihydro-5H-tetrazole-5-thione

1-methyl-4-(naphthalen-1-yl(2,4,6-trimethoxyphenyl)methyl)-1,4-dihydro-5H-tetrazole-5-thione

Conditions
ConditionsYield
With 2,2,2-trifluoroethanol; iodine at 20℃; for 3h; chemoselective reaction;97%
...Expand
(E)-2-methyl-3-phenylallyl pivalate

(E)-2-methyl-3-phenylallyl pivalate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

(E)-1-methyl-5-((2-methyl-3-phenylallyl)thio)-1H-tetrazole

(E)-1-methyl-5-((2-methyl-3-phenylallyl)thio)-1H-tetrazole

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 80℃; for 1h;96%
(E)-3,7-dimethylocta-2,6-dien-1-yl pivalate
85796-37-8

(E)-3,7-dimethylocta-2,6-dien-1-yl pivalate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

(E)-5-(3,7-dimethylocta-2,6-dienylthio)-1-methyl-1H-tetrazole

(E)-5-(3,7-dimethylocta-2,6-dienylthio)-1-methyl-1H-tetrazole

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 80℃; for 2h;96%
acetophenone
98-86-2

acetophenone

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

2-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]-1-phenylethanone
80087-27-0

2-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]-1-phenylethanone

Conditions
ConditionsYield
With hydrogen iodide In water; dimethyl sulfoxide at 80℃; for 4h; Reagent/catalyst; Green chemistry; regioselective reaction;96%
With dipotassium peroxodisulfate; potassium iodide In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique;85%
With dipotassium peroxodisulfate; potassium iodide In dimethyl sulfoxide at 20℃; for 24h;85%
p-methoxybenzyl 7β-(2-phenylacetamido)-3-chloromethyl-3-cephem-4-carboxylate
104146-10-3

p-methoxybenzyl 7β-(2-phenylacetamido)-3-chloromethyl-3-cephem-4-carboxylate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

7-phenylacetylamino-3-[[(1-methyl-1H-5-tetrazolyl)thio]methyl]cephalosporanic acid p-methoxybenzyl ester

7-phenylacetylamino-3-[[(1-methyl-1H-5-tetrazolyl)thio]methyl]cephalosporanic acid p-methoxybenzyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 10h;96%
2-(4-bromobutyl)isoindoline-1,3-dione
5394-18-3

2-(4-bromobutyl)isoindoline-1,3-dione

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

2-(4-((1-methyl-1H-tetrazol-5-yl)thio)butyl)isoindoline-1,3-dione

2-(4-((1-methyl-1H-tetrazol-5-yl)thio)butyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;96%
(E)-1-(2-methylphenyl)-1-heptene-3-one

(E)-1-(2-methylphenyl)-1-heptene-3-one

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

(E)-4-((1-methyl-1H-tetrazol-5-yl)thio)-1-(o-tolyl)hept-1-en-3-one

(E)-4-((1-methyl-1H-tetrazol-5-yl)thio)-1-(o-tolyl)hept-1-en-3-one

Conditions
ConditionsYield
With deuterium iodide; dimethyl sulfoxide In water at 80℃; for 2.5h; regioselective reaction;96%
7β-(D-5-carboxy-5-phthalimidovaleramido)-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid

7β-(D-5-carboxy-5-phthalimidovaleramido)-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

7β-(D-5-carboxy-5-phthalimidovaleramido)-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]ceph-3-em-4-carboxylic acid

7β-(D-5-carboxy-5-phthalimidovaleramido)-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]ceph-3-em-4-carboxylic acid

Conditions
ConditionsYield
With sodium bicarbonate; sodium chloride In ethyl acetate (100 ml)-water; water; toluene95.5%
1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

7-Aminocephalosporanic acid
957-68-6

7-Aminocephalosporanic acid

C10H14N6O3S2

C10H14N6O3S2

Conditions
ConditionsYield
Stage #1: 1-methyl-5-mercaptotetrazole; 7-Aminocephalosporanic acid With boron trifluoride In acetonitrile at 35 - 39℃;
Stage #2: With hydrogenchloride In water; acetonitrile at 10 - 32℃; for 0.666667h; Reagent/catalyst;		95.1%
Stage #1: 1-methyl-5-mercaptotetrazole With acetonitrile boron trifluoride complex at 30℃; for 0.5h;
Stage #2: 7-Aminocephalosporanic acid at 30℃; for 1h;
(3R,4R)-4-{(1S)-3-chloro-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one
90244-30-7

(3R,4R)-4-{(1S)-3-chloro-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

(3R,4R)-4-{(1S)-3-(1-methyl-1H-tetrazole-5-yl)thio-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)-azetidin-2-one
90211-61-3

(3R,4R)-4-{(1S)-3-(1-methyl-1H-tetrazole-5-yl)thio-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)-azetidin-2-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 1h; Ambient temperature;95%
tetramethyl ammoniumhydroxide
75-59-2

tetramethyl ammoniumhydroxide

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

5-mercapto-1-methyltetrazole N-tetramethylammonium salt
1358553-81-7

5-mercapto-1-methyltetrazole N-tetramethylammonium salt

Conditions
ConditionsYield
In methanol at 20℃; for 12h; Inert atmosphere;95%

5-Mercapto-1-methyltetrazole Consensus Reports

Reported in EPA TSCA Inventory.

5-Mercapto-1-methyltetrazole Specification

1. Introduction of 5-Mercapto-1-methyltetrazole
5-Mercapto-1-methyltetrazole is one kind of white crystalline powder. 1-Methyl-1h-tetrazole-5-thiol has the IUPAC name of 1-methyl-2H-tetrazole-5-thione. For being sensitive to air, its product categories are including Tetrazoles; Phenoles and thiophenoles; Cephalosporins; Building Blocks; Heterocyclic Building Blocks. Solubility of 5-mercapto-1-methyltetrazole in pure solvents from (283 to 329) Kwere accurately correlated by a modified Apelblat equation.
It is a air sensitive product. It belongs to Tetrazoles;Phenoles and thiophenoles;Cephalosporins;Building Blocks;Heterocyclic Building Blocks;Heterocycles;Sulfur & Selenium Compounds;chemical additive;pharmaceutical intermediates. It should be stored at Room temperature and closed, a cool air drying.

2. Properties of 5-Mercapto-1-methyltetrazole
Physical properties about 5-Mercapto-1-methyltetrazole are:
(1)ACD/LogP: -1.10; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.09; (4)ACD/LogD (pH 7.4): -1.09; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 6.05; (8)ACD/KOC (pH 7.4): 6.05; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 63.29; (13)Index of Refraction: 1.807; (14)Molar Refractivity: 29.46 cm3; (15)Molar Volume: 68.4 cm3; (16)Polarizability: 11.68 ×10-24 cm3; (17)Surface Tension: 61 dyne/cm; (18)Density: 1.69 g/cm3; (19)Flash Point: 21.3 °C; (20)Enthalpy of Vaporization: 35.02 kJ/mol; (21)Boiling Point: 111.6 °C at 760 mmHg; (22)Vapour Pressure: 22.5 mmHg at 25°C; (23)Exact Mass: 116.015667; (24)MonoIsotopic Mass: 116.015667; (25)Topological Polar Surface Area: 72.1; (26)Heavy Atom Count: 7; (27)Complexity: 119.

4. Structure Descriptors of 5-Mercapto-1-methyltetrazole
(1)Canonical SMILES: CN1C(=S)N=NN1
(2)InChI: InChI=1S/C2H4N4S/c1-6-2(7)3-4-5-6/h1H3,(H,3,5,7)
(3)InChIKey: XOHZHMUQBFJTNH-UHFFFAOYSA-N

5. Safety Information of 5-Mercapto-1-methyltetrazole
When you are dealing with this chemical, you should be careful. For being a kind of harmful chemical, it may cause damage to health, and it is also irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
Hazard Symbols: XiXi
Risk Codes: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin.
Safety Description: 26-37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
37/39: Wear suitable gloves and eye/face protection.

6. Uses of 5-Mercapto-1-methyltetrazole
As to its usage, it is widely applied in pharmaceutics. It could be used as the intermediate of Cephems antibiotic, such as Cefamandole, cefoperazone, cefamandole, cefmetazole sodium, cefotetan and cefotetan. It is an impurity of cefoperazone. It is pharmaceutical intermediates. It can be used as intermediate for cefoperazone cefmenoxime etc.
 

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