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13183-79-4

Basic Information
CAS No.: 13183-79-4
Name: 5-Mercapto-1-methyltetrazole
Molecular Structure:
Molecular Structure of 13183-79-4 (5-Mercapto-1-methyltetrazole)
Formula: C2H4N4S
Molecular Weight: 116.15 .
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-;
EINECS: 236-132-2
Density: 1.69 g/cm3
Melting Point: 125-128 °C(lit.)
Boiling Point: 111.6 °C at 760 mmHg
Flash Point: 21.3 °C
Solubility:
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 82.40000
LogP: -0.50120
Synthetic route
556-61-6

methyl thioisocyanate

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;
137-42-8

sodium N-methyldithiocarbamate

13183-79-4

1-methyl-5-mercaptotetrazole

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

C4H6Cl2N2S2

13183-79-4

1-methyl-5-mercaptotetrazole

Conditions
ConditionsYield
With sodium azide In ethanol; water at 20 - 50℃; for 2.5h;93.1%
62671-38-9

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

13183-79-4

1-methyl-5-mercaptotetrazole

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

4-methylthiosemicarbazide

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%
62671-38-9

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

diluted NaOH-solution

diluted NaOH-solution

13183-79-4

1-methyl-5-mercaptotetrazole

13183-79-4

1-methyl-5-mercaptotetrazole

2-pivaloyloxymethylfuran

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

13183-79-4

1-methyl-5-mercaptotetrazole

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

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

C20H36Au4N4O12S4

584-08-7

potassium carbonate

13183-79-4

1-methyl-5-mercaptotetrazole

potassium hydroxide

C7H10AuN5O3S2(1-)*K(1+)

Conditions
ConditionsYield
In water at 20 - 80℃; for 3h;100%
4119-41-9

1-iodo-3-phenylpropan

13183-79-4

1-methyl-5-mercaptotetrazole

C11H14N4S

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

1-naphthylmethyl 2,2-dimethylpropanoate

13183-79-4

1-methyl-5-mercaptotetrazole

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

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 80℃; for 0.5h;99%
1014394-72-9

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

13183-79-4

1-methyl-5-mercaptotetrazole

(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

13183-79-4

1-methyl-5-mercaptotetrazole

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

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 80℃; for 1h;99%
1191-99-7

2,3-dihydro-2H-furan

13183-79-4

1-methyl-5-mercaptotetrazole

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

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

1,1-Diphenylmethanol

13183-79-4

1-methyl-5-mercaptotetrazole

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%
13183-79-4

1-methyl-5-mercaptotetrazole

957-68-6

7-Aminocephalosporanic 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%
591-50-4

iodobenzene

13183-79-4

1-methyl-5-mercaptotetrazole

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

13183-79-4

1-methyl-5-mercaptotetrazole

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

Conditions
ConditionsYield
In methanol for 3h;98%
13183-79-4

1-methyl-5-mercaptotetrazole

89-25-8

edaravone

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%
622-97-9

1-ethenyl-4-methylbenzene

13183-79-4

1-methyl-5-mercaptotetrazole

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%
1092986-09-8

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

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

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

1,2,3-trimethoxybenzene

66-77-3

1-naphthaldehyde

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

Conditions
ConditionsYield
With 2,2,2-trifluoroethanol; iodine at 20℃; for 3h; chemoselective reaction;97%

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

13183-79-4

1-methyl-5-mercaptotetrazole

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

Conditions
ConditionsYield
With iron(III) chloride In acetonitrile at 80℃; for 1h;96%
85796-37-8

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

13183-79-4

1-methyl-5-mercaptotetrazole

(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%
98-86-2

acetophenone

13183-79-4

1-methyl-5-mercaptotetrazole

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%
104146-10-3

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

13183-79-4

1-methyl-5-mercaptotetrazole

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%
5394-18-3

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

13183-79-4

1-methyl-5-mercaptotetrazole

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

13183-79-4

1-methyl-5-mercaptotetrazole

(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

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

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

1-methyl-5-mercaptotetrazole

957-68-6

7-Aminocephalosporanic acid

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;
90244-30-7

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

13183-79-4

1-methyl-5-mercaptotetrazole

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%
75-59-2

tetramethyl ammoniumhydroxide

13183-79-4

1-methyl-5-mercaptotetrazole

1358553-81-7

5-mercapto-1-methyltetrazole N-tetramethylammonium salt

Conditions
ConditionsYield
In methanol at 20℃; for 12h; Inert atmosphere;95%
Downstream Products
24209-38-9
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    5-Mercapto-1-methyltetrazole 13183-79-4 5-Mercapto-1-methyltetrazole Basic information Product Name: 5-Mercapto-1-methyltetrazole Synonyms: 1,2-dihydro-1-methyl-5h-tetrazole-5-thion;1-

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    5-Mercapto-1-methyltetrazole

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Consensus Reports

Reported in EPA TSCA Inventory.

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.