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58909-39-0

Basic Information
CAS No.: 58909-39-0
Name: Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione
Article Data: 7
Molecular Structure:
Molecular Structure of 58909-39-0 (Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione)
Formula: C4H5N3O2S
Molecular Weight: 159.169
Synonyms: 2,5-Dihydro-6-Hydroxy-3-Mercapto-2-Methyl-5-oxo-1,2,4-Triazine ( TTZ , Thiotriazinone );2-Methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazine-3-thiol;
EINECS: 261-490-1
Density: 1.62 g/cm3
Melting Point: 168-171 °C(lit.)
Boiling Point: 272.3 °C at 760 mmHg
Flash Point: 118.5 °C
Appearance: white powder
Hazard Symbols: Xi
Risk Codes: 20/21/22
Safety: 36
PSA: 102.74000
LogP: -0.86880
Synthetic route
6938-68-7

2-methyl-thiosemicarbazide

95-92-1

oxalic acid diethyl ester

58909-39-0

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

Conditions
ConditionsYield
With dmap; N,N,N,N,-tetramethylethylenediamine; sodium methylate In methanol; ethanol at 15 - 55℃; for 4h; Temperature; Solvent; Reagent/catalyst;92.7%
With sodium methylate In methanol; dimethyl sulfoxide at 0 - 45℃; Solvent;91.6%
553-90-2

Dimethyl oxalate

ammonium thiocyanate

60-34-4

methylhydrazine

58909-39-0

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

Conditions
ConditionsYield
Stage #1: ammonium thiocyanate; methylhydrazine In water at 95 - 100℃;
Stage #2: Dimethyl oxalate With sodium methylate In methanol at 65 - 75℃; for 6h; Temperature;
75%

sodium salt of ceftriaxone

A

58909-39-0

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

B

(6R,7S)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-[1,2,4]triazin-3-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid anion

C

153470-19-0

C14H13N5O6S2(2-)

Conditions
ConditionsYield
With Carbonate buffer at 37℃; Rate constant; H/D-isotopic effect were studied too;

(6R,7S)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-(6-hydroxy-2-methyl-5-oxo-2,5-dihydro-[1,2,4]triazin-3-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid anion

A

58909-39-0

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

B

sodium salt of ceftriaxone

C

C14H13N5O6S2(2-)

Conditions
ConditionsYield
With Carbonate buffer at 37℃; Rate constant; H/D-isotopic effect were studied too;
58909-39-0

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

94088-75-2

2-(2-amino-1,3-thiazol-4-yl)-1-(1,3-benzothiazol-2-ylsulfanyl)-2-(methoxyimino)ethan-1-one

957-68-6

7-Aminocephalosporanic acid

ceftriaxone sodium

Conditions
ConditionsYield
Stage #1: 2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine; 7-Aminocephalosporanic acid With carbonic acid dimethyl ester at 35℃; for 1h;
Stage #2: 2-(2-amino-1,3-thiazol-4-yl)-1-(1,3-benzothiazol-2-ylsulfanyl)-2-(methoxyimino)ethan-1-one for 0.166667h;
Stage #3: With triethylamine at 10℃; for 4h; Concentration; Temperature;
99.5%
58909-39-0

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

957-68-6

7-Aminocephalosporanic acid

58909-56-1

7-aminoceftrizine

Conditions
ConditionsYield
With boron trifluoride dimethyl carbonate complex; methanesulfonic acid at 10 - 12℃; for 0.383333h; Reagent/catalyst;95.1%
With boron trifluoride dimethyl carbonate complex; edetate disodium at 30℃; for 0.833333h; Time;90%
With boron trifluoride In acetonitrile at 10 - 30℃; for 0.5h;85.71%
58909-39-0

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

957-68-6

7-Aminocephalosporanic acid

58909-56-1

7-amino-3-[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazine-3-mercapto)methyl]-3 cephalosporin-4-carboxylic acid

Conditions
ConditionsYield
With aluminum (III) chloride; boron trifluoride; carbonic acid dimethyl ester at 5 - 30℃; for 1h;92%
With aluminum (III) chloride; boron trifluoride; carbonic acid dimethyl ester at 5 - 30℃; for 1h; Reagent/catalyst;90%
58909-39-0

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

143731-84-4

7α-methoxy-8-oxo-2-(pyrrolidinocarbonyl)-3-(chloromethyl)-5-thia-1-azabicyclo<4.2.0>oct-2-ene 5,5-dioxide

119742-06-2

L-659,286

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone for 16h; Ambient temperature;85%
58909-39-0

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

7585-39-9

fipronilβ-cyclodextrin

C4H5N3O2S*C42H70O35

Conditions
ConditionsYield
In water at 30℃; for 24.5h;83%
58909-39-0

2-methyl-3-mercapto-5-oxo-6-hydroxy-2,5-dihydro-1,2,4-triazine

95672-05-2

1,1-dimethylethyl 3-(chloromethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide

116536-09-5

1,1-dimethylethyl 7α-methoxy-3-{[(1,2,5,6-tetrahydro-5,6-dioxo-2-methyl-as-triazin-3-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 5,5-dioxide

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone80%
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Chemistry

The Molecular Structure of Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione (CAS NO.58909-39-0):

Empirical Formula: C4H5N3O2S
Molecular Weight: 159.1664 
IUPAC: 2-methyl-3-sulfanylidene-1,2,4-triazinane-5,6-dione
Product Categories: Building Blocks;Heterocyclic Building Blocks;Triazines
Nominal Mass: 159 Da
Average Mass: 159.1664 Da
Monoisotopic Mass: 159.010246 Da 
Index of Refraction: 1.678
Molar Refractivity: 37.04 cm3
Molar Volume: 98.1 cm3
Surface Tension: 87.6 dyne/cm
Density: 1.62 g/cm3
Flash Point: 118.5 °C
Enthalpy of Vaporization: 59.28 kJ/mol
Boiling Point: 272.3 °C at 760 mmHg
Vapour Pressure: 0.000795 mmHg at 25°C 
InChI
InChI=1/C4H5N3O2S/c1-7-4(10)5-2(8)3(9)6-7/h1H3,(H,6,9)(H,5,8,10)
Smiles
[nH]1c(n(C)[nH]c(c1=O)=O)=S

Uses

 Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione (CAS NO.58909-39-0) can be used as intermediates of ceftriaxone, ceftriaxone sodium, etc. drugs.

Safety Profile

Risk Statements: 20/21/22 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 36 
S36:Wear suitable protective clothing
WGK Germany: 3

Specification

 Tetrahydro-2-methyl-3-thioxo-1,2,4-triazine-5,6-dione (CAS NO.58909-39-0) is also called as EINECS 261-490-1 .