Product Name

  • Name

    Sodium omadine

  • EINECS 223-296-5
  • CAS No. 3811-73-2
  • Article Data6
  • CAS DataBase
  • Density 1.22 g/cm3
  • Solubility 54.7 g/100 mL
  • Melting Point -25 °C
  • Formula C5H4NNaOS
  • Boiling Point 253.8 °C at 760 mmHg
  • Molecular Weight 149.149
  • Flash Point 107.3 °C
  • Transport Information
  • Appearance clear solution
  • Safety 26-36-24/25-37/39
  • Risk Codes 22-36/37/38-36/38
  • Molecular Structure Molecular Structure of 3811-73-2 (Sodium omadine)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms 2-Pyridinethiol, 1-oxide, sodium salt (8CI,9CI);Sodium, (2-pyridylthio)-, N-oxide (7CI);1-Oxo-2-pyridinethiol sodium salt;2-Mercaptopyridine N-oxide sodium salt;2-Pyridylthiol-N-oxide sodium salt;Sodium 2-mercaptopyridine 1-oxide;Sodium pyridine-1-oxide-2-thiolate;Sodium pyrithione;Thione (reagent);2-Pyridinethiol,1-oxide, sodium salt (1:1);
  • PSA 25.46000
  • LogP 1.02090

Synthetic route

pyridine N-oxide
694-59-7

pyridine N-oxide

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

Conditions
ConditionsYield
Stage #1: pyridine N-oxide With sodium sulfide; 1,3-diisopropylbenzene; sulfur; calcium hydroxide In water at 200℃; for 3.5h; Inert atmosphere;
Stage #2: With sodium hydroxide In water pH=8; Temperature; Time; Reagent/catalyst;
Stage #1: pyridine N-oxide With sodium sulfide; sodium hexadecyl diphenyl oxide disulfonate; sulfur; calcium hydroxide at 200℃; Autoclave; Inert atmosphere; Reflux;
Stage #2: With hydrogenchloride In water pH=3;
Stage #3: With sodium hydroxide In water pH=9; Reagent/catalyst; Temperature;
2-chloropyridine
109-09-1

2-chloropyridine

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dihydrogen peroxide / water / 1 h / 65 - 80 °C
2: sodium hydrogen sulfide; sodium hydroxide / water / 2.5 h / 60 - 65 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1: dihydrogen peroxide / water / 2 h / 65 - 80 °C / Molecular sieve; Green chemistry
2: sodium hydrogen sulfide; sodium hydroxide / 2 h / 65 - 80 °C / Green chemistry
View Scheme
Multi-step reaction with 2 steps
1: dihydrogen peroxide / water / 7 h / 90 °C
2: sodium hydrogen sulfide; sodium hydroxide / 3 h / 80 °C
View Scheme
2-chloropyridine-N-oxide
2402-95-1

2-chloropyridine-N-oxide

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

Conditions
ConditionsYield
With sodium hydrogen sulfide; sodium hydroxide In water at 60 - 65℃; for 2.5h; Large scale;1218 g
With sodium hydrogen sulfide; sodium hydroxide at 65 - 80℃; for 2h; Green chemistry;544 g
With sodium hydrogen sulfide; sodium hydroxide at 80℃; for 3h;
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

N-Butyl-cyclohexanecarboximidoyl chloride

N-Butyl-cyclohexanecarboximidoyl chloride

1-<(N-Butylcyclohexanecarboximidyl)oxy>-2(1H)-pyridinethione

1-<(N-Butylcyclohexanecarboximidyl)oxy>-2(1H)-pyridinethione

Conditions
ConditionsYield
In diethyl ether100%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

13-bromo-12-methoxypodocarpa-8,11,13-trien-19-oyl chloride
352233-40-0

13-bromo-12-methoxypodocarpa-8,11,13-trien-19-oyl chloride

13-bromo-12-methoxy-4α-(2'-pyridylthio)-18-norpodocarpa-8,11,13-triene
352233-41-1

13-bromo-12-methoxy-4α-(2'-pyridylthio)-18-norpodocarpa-8,11,13-triene

Conditions
ConditionsYield
With dmap In benzene for 1.75h; Heating;100%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

zinc(II) chloride
7646-85-7

zinc(II) chloride

zinc pyrithione
13463-41-7

zinc pyrithione

Conditions
ConditionsYield
In water at 70℃; for 1.16667h; Product distribution / selectivity;99.1%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

copper dichloride

copper dichloride

copper pyrithione

copper pyrithione

Conditions
ConditionsYield
In water at 70℃; for 2h; Product distribution / selectivity;98.8%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

[η2-C5H4SN(O)]PtCl(DMSO)

[η2-C5H4SN(O)]PtCl(DMSO)

Conditions
ConditionsYield
Stage #1: potassium tetrachloroplatinate(II); 2-mercaptopyridine-1-oxide sodium salt In water; N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: dimethyl sulfoxide In water; N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere;		98%
...Expand
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

tin(ll) chloride

tin(ll) chloride

(2-mercaptopyridine-N-oxide)2Sn

(2-mercaptopyridine-N-oxide)2Sn

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Schlenk technique;97%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

benzyl bromide
100-39-0

benzyl bromide

2-(benzylsulfanyl)pyridine 1-oxide
3915-60-4

2-(benzylsulfanyl)pyridine 1-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 2h;96%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

tin(ll) chloride

tin(ll) chloride

(2-mercaptopyridine-N-oxide)SnCl

(2-mercaptopyridine-N-oxide)SnCl

Conditions
ConditionsYield
In tetrahydrofuran for 24h; Inert atmosphere; Schlenk technique;96%
chloroxoacetic acid (4-nitrophenyl)methyl ester
81779-73-9

chloroxoacetic acid (4-nitrophenyl)methyl ester

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

2-[(4-nitrobenzyl)sulfanyl]pyridine
104742-05-4

2-[(4-nitrobenzyl)sulfanyl]pyridine

Conditions
ConditionsYield
With PVS In benzene for 1h; Heating;95%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

PtCl(DMSO)[η2-C5H4SN(O)]

PtCl(DMSO)[η2-C5H4SN(O)]

Conditions
ConditionsYield
Stage #1: potassium tetrachloroplatinate(II); 2-mercaptopyridine-1-oxide sodium salt In water; N,N-dimethyl-formamide for 1h;
Stage #2: dimethyl sulfoxide In water; N,N-dimethyl-formamide for 72h;		94%
...Expand
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

manganese(III) triacetate dihydrate
19513-05-4

manganese(III) triacetate dihydrate

tris(1-hydroxy-2-pyridinethionato)manganese(III)

tris(1-hydroxy-2-pyridinethionato)manganese(III)

Conditions
ConditionsYield
In methanol addn. of Mn-compd. to soln. of org. compd. in MeOH with stirring, stirring (15 min); filtration, washing (MeOH and small amt. of H2O), drying (vac., P4O10); elem. anal.;93%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

n-pentadecyl-2'-pyridylsulphide
89025-53-6

n-pentadecyl-2'-pyridylsulphide

Conditions
ConditionsYield
dmap In cyclohexane at 81℃; for 2h;92%
In cyclohexene at 81℃; for 2h; Product distribution; in various solvents, with or without irradiation;
12-methoxypodocarpa-8,11,13-trien-19-oyl chloride
22376-00-7

12-methoxypodocarpa-8,11,13-trien-19-oyl chloride

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

12-methoxy-4α-(2'-pyridylthio)-18-norpodocarpa-8,11,13-triene
135521-17-4

12-methoxy-4α-(2'-pyridylthio)-18-norpodocarpa-8,11,13-triene

Conditions
ConditionsYield
With dmap In benzene for 1.5h; Heating;91%
With dmap In toluene Heating;5.42 g
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

C15H26ClNO
104525-90-8

C15H26ClNO

Cyclohexyl-(1,5-dimethyl-hex-4-enyl)-carbamic acid 2-thioxo-2H-pyridin-1-yl ester
104525-91-9

Cyclohexyl-(1,5-dimethyl-hex-4-enyl)-carbamic acid 2-thioxo-2H-pyridin-1-yl ester

Conditions
ConditionsYield
90%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

ethyl 2-methylene-3-t-butylthiopropanoate
92822-43-0

ethyl 2-methylene-3-t-butylthiopropanoate

A

2-(2-tert-butyldisulfanyl)pyridine
24367-44-0

2-(2-tert-butyldisulfanyl)pyridine

B

ethyl 3α-acetoxy-12-oxo-5βH-cholest-25-en-27-oate
108055-30-7

ethyl 3α-acetoxy-12-oxo-5βH-cholest-25-en-27-oate

Conditions
ConditionsYield
With reagent 20 In chlorobenzene at 133℃; for 1.5h;A 90%
B 76%
...Expand
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

2,2-Dimethyl-tetradecanoyl chloride
85216-68-8

2,2-Dimethyl-tetradecanoyl chloride

N-(2,2-dimethyltetradecanoyloxy)-2-pyridinethione
173776-78-8

N-(2,2-dimethyltetradecanoyloxy)-2-pyridinethione

Conditions
ConditionsYield
In dichloromethane90%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

Stearoyl chloride
112-76-5

Stearoyl chloride

N-octadecanoyloxy-2-pyridinethione
89025-66-1

N-octadecanoyloxy-2-pyridinethione

Conditions
ConditionsYield
In dichloromethane90%
5-hexenoyl chloride
36394-07-7

5-hexenoyl chloride

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

hex-5-enoic acid 2-thioxo-2H-pyridin-1-yl ester
197148-70-2

hex-5-enoic acid 2-thioxo-2H-pyridin-1-yl ester

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;90%
bismuth(III) chloride

bismuth(III) chloride

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

[BiIII(mpo)3]

[BiIII(mpo)3]

Conditions
ConditionsYield
In methanol for 20h; Reflux;90%
N-Acetyl-N-methylcarbamoyl chloride
21777-48-0

N-Acetyl-N-methylcarbamoyl chloride

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

1-<(N-Acetyl-N-methylcarbamoyl)oxy>-2(1H)-pyridinethione
144809-63-2

1-<(N-Acetyl-N-methylcarbamoyl)oxy>-2(1H)-pyridinethione

Conditions
ConditionsYield
In dichloromethane for 4h;89%
In benzene for 1.5h;
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

propyl bromide
106-94-5

propyl bromide

2-(n-propylthio)pyridine N-oxide
122333-44-2

2-(n-propylthio)pyridine N-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 2h;89%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

2-((1R,2S)-2-Phenyl-cyclobutyl)-propionic acid

2-((1R,2S)-2-Phenyl-cyclobutyl)-propionic acid

2-(cis-2-phenylcyclobutyl)propanoic acid 2-thioxo-2H-pyridin-1-yl ester

2-(cis-2-phenylcyclobutyl)propanoic acid 2-thioxo-2H-pyridin-1-yl ester

Conditions
ConditionsYield
Stage #1: 2-((1R,2S)-2-Phenyl-cyclobutyl)-propionic acid With N,N-dimethyl-formamide In benzene for 1h; Chlorination;
Stage #2: 2-mercaptopyridine-1-oxide sodium salt With dmap In benzene for 1h; Acylation;		89%
2-benzyl-3-phenyl-propionyl chloride
49802-75-7

2-benzyl-3-phenyl-propionyl chloride

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

1,3-diphenyl-2-(2'-pyridylthio)-propane
102720-53-6

1,3-diphenyl-2-(2'-pyridylthio)-propane

Conditions
ConditionsYield
dmap In chlorobenzene at 133℃; for 2.5h;88%
valproyl chloride
2936-08-5

valproyl chloride

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

N-(1-propylbutanoyloxy)-2-pyridinethione
173776-81-3

N-(1-propylbutanoyloxy)-2-pyridinethione

Conditions
ConditionsYield
In dichloromethane88%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

dimethyltin dichloride
753-73-1

dimethyltin dichloride

[Me2SnCl(2-pyridinethiolato-N-oxide)]

[Me2SnCl(2-pyridinethiolato-N-oxide)]

Conditions
ConditionsYield
In benzene under N2; Na-contg. compd. (1.0 mmol) was added to a soln. of benzene ina Schlenk flask and stirred; then Sn-contg. compd. (1.0 mmol) was added ; the mixt. was stirred for 12 h at 40°C and then was filtered; the filtrate was removed by evapn. under vac.; the solid was recrystd. from CH2Cl2-hexane; elem. anal.;88%
1-bromo-butane
109-65-9

1-bromo-butane

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

2-(n-butylthio)pyridine N-oxide
122333-47-5

2-(n-butylthio)pyridine N-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 2h;87%
2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

16α,17α-(R)-butylidenedioxy-6α,9α-difluoro-11β-hydroxy-3-oxoandrosta-4-ene-17β-carboxylic acid diethyl phosphoric anhydride
184374-72-9

16α,17α-(R)-butylidenedioxy-6α,9α-difluoro-11β-hydroxy-3-oxoandrosta-4-ene-17β-carboxylic acid diethyl phosphoric anhydride

16α,17α-(R)-butylidenedioxy-6α,9α-difluoro-11β-hydroxy-3-oxoandrosta-4-ene-17β-carboxylic acid 2-thioxo-2H-pyridin-1-yl ester
184374-74-1

16α,17α-(R)-butylidenedioxy-6α,9α-difluoro-11β-hydroxy-3-oxoandrosta-4-ene-17β-carboxylic acid 2-thioxo-2H-pyridin-1-yl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;87%
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

bis(2-mercaptopyridine N-oxide) nickel(II)

bis(2-mercaptopyridine N-oxide) nickel(II)

Conditions
ConditionsYield
In methanol; acetonitrile stirred for 15 h, filtered; recrystn. (DMF), storage of the filtrate at 5°C yields further crystals;87%
[Pt(κ2-C,N-2-phenylpyridine)(dimethyl sulfoxide)Cl]

[Pt(κ2-C,N-2-phenylpyridine)(dimethyl sulfoxide)Cl]

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

C16H12N2OPtS

C16H12N2OPtS

Conditions
ConditionsYield
In ethanol at 20℃; for 2h; Inert atmosphere;87%
4-chloro-3,5-dinitrobenzotrifluoride
393-75-9

4-chloro-3,5-dinitrobenzotrifluoride

2-mercaptopyridine-1-oxide sodium salt
3811-73-2

2-mercaptopyridine-1-oxide sodium salt

2-<2,6-dinitro-4-trifluoromethylphenylthio>pyridine N-oxide

2-<2,6-dinitro-4-trifluoromethylphenylthio>pyridine N-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 25 - 30℃; for 72h;86%

2-Pyridinethiol-1-oxide sodium salt Chemical Properties

IUPAC Name: sodium 1-oxidopyridine-2-thione 
Empirical Formula: C5H4NNaOS
Molecular Weight: 149.1461g/mol
EINECS: 223-296-5 
Structure of 2-Pyridinethiol,1-oxide, sodium salt (1:1) (CAS NO.3811-73-2):

Melting Point: -25 °C
Flash Point: 107.3 °C
Enthalpy of Vaporization: 57.06 kJ/mol
Boiling Point: 253.8 °C at 760 mmHg
Vapour Pressure: 0.00275 mmHg at 25°C 
Density: 1.22
Solubility: H2O: 0.1 M at 20 °C, clear, faintly yellow
Water Solubility: 54.7 g/100 mL
Sensitive: Hygroscopic 
Product Categories: Pyridines derivates;Heterocyclic Compounds;Classes of Metal Compounds;Na (Sodium) Compounds (excluding simple sodium salts);Typical Metal Compounds;C5;Heterocyclic Building Blocks;Pyridines 
Canonical SMILES: C1=CC(=S)N(C=C1)[O-].[Na+]
InChI: InChI=1S/C5H4NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4H;/q-1;+1
InChIKey: XNRNJIIJLOFJEK-UHFFFAOYSA-N

2-Pyridinethiol-1-oxide sodium salt Toxicity Data With Reference

1.    

orl-mus LD50:870 mg/kg

     OYYAA2    Oyo Yakuri. Pharmacometrics. 4 (1970),883.
2.    

ipr-mus LD50:370 mg/kg

     OYYAA2    Oyo Yakuri. Pharmacometrics. 4 (1970),883.
3.    

scu-mus LD50:428 mg/kg

     OYYAA2    Oyo Yakuri. Pharmacometrics. 4 (1970),883.
4.    

ivn-mus LD50:320 mg/kg

     CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#04703 .
5.    

par-mus LDLo:800 mg/kg

     CBCCT*    “Summary Tables of Biological Tests“ National Research Council Chemical-Biological Coordination Center. 7 (1955),693.

2-Pyridinethiol-1-oxide sodium salt Consensus Reports

Reported in EPA TSCA Inventory.

2-Pyridinethiol-1-oxide sodium salt Safety Profile

Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion, subcutaneous and parenteral routes. Used in preservation of cosmetics. When heated to decomposition it emits very toxic fumes of Na2O, NOx, and SOx. See also MERCAPTANS.
Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38-36/38 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R36/38:Irritating to eyes and skin.
Safety Statements: 26-36-24/25-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S24/25:Avoid contact with skin and eyes. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: UT9000000
F: 3-13  

2-Pyridinethiol-1-oxide sodium salt Standards and Recommendations

DFG MAK: 1 mg/m3

2-Pyridinethiol-1-oxide sodium salt Specification

  2-Pyridinethiol,1-oxide, sodium salt (1:1) , its cas register number is 3811-73-2. It also can be called Hydroxy-2-pyridinethione), sodium salt, tech. ; 1-Oxo-2-pyridinethiol sodium salt ; 2-Mercaptopyridine 1-oxide sodium salt ; 2-Mercaptopyridine-N-oxide sodium salt ; 2-Pyridinethiol N-oxide sodium salt ; 2-Pyridinethiol-1-oxide sodium salt ; Omadine sodium ; Sodium 2-pyridinethiolate 1-oxide ; Sodium pyrithione ; Sodium, (2-pyridinylthio)-, N-oxide ; Thione (reagent) . 2-Pyridinethiol,1-oxide, sodium salt (1:1) (CAS NO.3811-73-2) is a clear solution.

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