3811-73-2

Basic information

• Product Name: Sodium omadine
• Synonyms: SODIUM-2-PYRIDINETHIOL-1-OXIDE;SODIUM PYRIDINE-2-THIOLATE 1-OXIDE HYDRATE;SODIUM PYRITHIONE;SODIUM OMADINE;PYRITHIONE SODIUM;PYRITHIONE SODIUM SALT;N-Hydroxy-2-pyridinethione sodium salt;N-HYDROXYPYRIDINETHIONE SODIUM SALT
• CAS NO: 3811-73-2
• Molecular Formula: C₅H₄NNaOS
• Molecular Weight: 149.15
• EINECS: 223-296-5
• 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;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;personal care;intermediates
• Mol File: 3811-73-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: -25 °C
• Boiling Point: 109 °C
• Flash Point: 107.3 °C
• Appearance: very deep brown/Solution
• Density: 1.22
• Vapor Pressure: 0-0Pa at 25℃
• Refractive Index: 1.4825
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: H2O: 0.1 M at 20 °C, clear, faintly yellow
• Water Solubility: 54.7 g/100 mL
• Sensitive: Hygroscopic
• Merck: 14,7994
• BRN: 4026050
• CAS DataBase Reference: Sodium omadine(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium omadine(3811-73-2)
• EPA Substance Registry System: Sodium omadine(3811-73-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-36/38
• Safety Statements: 26-36-24/25-37/39
• RIDADR: UN 3334
• WGK Germany: 3
• RTECS: UT9000000
• F: 3-13
• TSCA: Yes
• Hazardous Substances Data: 3811-73-2(Hazardous Substances Data)

Usage

Description

Sodium pyrithione is mainly used for anti-mildew and antibacterial products in the fields of daily chemicals (shampoo and hair care products), architectural coatings, adhesives, sealants, pesticides, textiles, leather products, metal working fluids, etc. It can also be formulated for disinfection agents, detergents and medical broad-spectrum antifungal dermatological products. At the same time, it is also an effective fungicide and an excellent common disinfectant for fruit trees, peanuts, wheat, vegetables and other crops. Its derivative product, zinc pyrithione, is also a commonly used fungicide for daily chemicals.

Chemical Properties

sodium pyrithione belongs to pyridine derivatives fungicide, appearance is yellow full light dumpling transparent liquid, melting point 250 ℃, slightly characteristic odor. Soluble in water and ethanol and other organic solvents, solubility (by mass fraction): water 53%, ethanol 19%, polyethylene glycol (PECG400) 12%. Best use pH range 7 to 10, mass fraction of 2% aqueous solution pH 8.0. Unstable to light, oxidizing agents and strong reducing agents. Non-ionic surfactants will deactivate it somewhat, and it can chelate with heavy metals.

Uses

Different sources of media describe the Uses of 3811-73-2 differently. You can refer to the following data:
1. sodium pyrithione is a preservative that is not commonly used because of some level of toxicity. It is prohibited in Canada, and it is on the eu Annex II list of substances that must not form part of a cosmetic product composition.
2. Sodium omadine is a bactericide for use in cooling fluids and short-term in-can preservation of vinyl acetate latex, paints, and synthetic-fiber lubricants; preservative for cosmetic rinse-off products.

Definition

Apparently exists in equilibrium with the -SH form. Forms chelates with iron, manganese, zinc, etc.

Application

2-Mercaptopyridine N-oxide sodium salt is one of the active components in paint, sealants, shampoo, adhesive and aerosol due to its anti-microbial activity. In biochemistry studies, it is utilized to transport zinc into cells. Further, it is used to form bidentate oxothiolane chelates with transition metals. It acts as a stabilizer and viscosity building provider in weak basic or neutral medium.

Brand name

Sodium Omadine (Olin).

General Description

2-Mercaptopyridine N-oxide acts as labelling agent during indium-111 labelling of human platelets. It acts as bioactive ligand and forms palladium and platinum complexes, which were tested as potential antitrypanosomal agents.

Biochem/physiol Actions

2-Mercaptopyridine N-oxide is a zinc ionophore that transports zinc into cells.

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.

Purification Methods

When recrystallised from water, it assayed as 98.7% based on AgNO3 titration [Krivis et al. Anal Chem 35 966 1963; see also Krivis et al. Anal Chem 48 1001 1976, and Barton & Crich J Chem Soc, Perkin Trans 1 1603, 1613 1986]. [Beilstein 21/7 V 151.]

Mode of action

Pyrithione Sodium is the sodium salt form of pyrithione, a fungistatic and antimicrobial derivative of aspergillic acid. Although the exact mechanism of action remains to be fully elucidated, pyrithione sodium appears to interfere with membrane transport ultimately leading to a loss of metabolic control.

InChI:InChI=1/C5H5NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4,8H;/q;+1

Synthetic route

pyridine N-oxide (694-59-7) → 2-mercaptopyridine-1-oxide sodium salt (3811-73-2)

Conditions	Yield
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-mercaptopyridine-1-oxide sodium salt (3811-73-2)

Conditions	Yield
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-mercaptopyridine-1-oxide sodium salt (3811-73-2)

Conditions	Yield
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) + N-Butyl-cyclohexanecarboximidoyl chloride → 1-<(N-Butylcyclohexanecarboximidyl)oxy>-2(1H)-pyridinethione

Conditions	Yield
In diethyl ether	100%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + 13-bromo-12-methoxypodocarpa-8,11,13-trien-19-oyl chloride (352233-40-0) → 13-bromo-12-methoxy-4α-(2'-pyridylthio)-18-norpodocarpa-8,11,13-triene (352233-41-1)

Conditions	Yield
With dmap In benzene for 1.75h; Heating;	100%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + zinc(II) chloride (7646-85-7) → zinc pyrithione (13463-41-7)

Conditions	Yield
In water at 70℃; for 1.16667h; Product distribution / selectivity;	99.1%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + copper dichloride → copper pyrithione

Conditions	Yield
In water at 70℃; for 2h; Product distribution / selectivity;	98.8%

potassium tetrachloroplatinate(II) (10025-99-7) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + dimethyl sulfoxide (67-68-5) → [η2-C5H4SN(O)]PtCl(DMSO)

Conditions	Yield
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%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + tin(ll) chloride → (2-mercaptopyridine-N-oxide)2Sn

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Schlenk technique;	97%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + benzyl bromide (100-39-0) → 2-(benzylsulfanyl)pyridine 1-oxide (3915-60-4)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 2h;	96%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + tin(ll) chloride → (2-mercaptopyridine-N-oxide)SnCl

Conditions	Yield
In tetrahydrofuran for 24h; Inert atmosphere; Schlenk technique;	96%

chloroxoacetic acid (4-nitrophenyl)methyl ester (81779-73-9) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → 2-[(4-nitrobenzyl)sulfanyl]pyridine (104742-05-4)

Conditions	Yield
With PVS In benzene for 1h; Heating;	95%

potassium tetrachloroplatinate(II) (10025-99-7) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + dimethyl sulfoxide (67-68-5) → PtCl(DMSO)[η2-C5H4SN(O)]

Conditions	Yield
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%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + manganese(III) triacetate dihydrate (19513-05-4) → tris(1-hydroxy-2-pyridinethionato)manganese(III)

Conditions	Yield
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) + n-hexadecanoyl chloride (112-67-4) → n-pentadecyl-2'-pyridylsulphide (89025-53-6)

Conditions	Yield
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) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → 12-methoxy-4α-(2'-pyridylthio)-18-norpodocarpa-8,11,13-triene (135521-17-4)

Conditions	Yield
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) + C15H26ClNO (104525-90-8) → Cyclohexyl-(1,5-dimethyl-hex-4-enyl)-carbamic acid 2-thioxo-2H-pyridin-1-yl ester (104525-91-9)

Conditions	Yield
	90%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + ethyl 2-methylene-3-t-butylthiopropanoate (92822-43-0) → 2-(2-tert-butyldisulfanyl)pyridine (24367-44-0) + ethyl 3α-acetoxy-12-oxo-5βH-cholest-25-en-27-oate (108055-30-7)

Conditions	Yield
With reagent 20 In chlorobenzene at 133℃; for 1.5h;	A 90% B 76%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + 2,2-Dimethyl-tetradecanoyl chloride (85216-68-8) → N-(2,2-dimethyltetradecanoyloxy)-2-pyridinethione (173776-78-8)

Conditions	Yield
In dichloromethane	90%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + Stearoyl chloride (112-76-5) → N-octadecanoyloxy-2-pyridinethione (89025-66-1)

Conditions	Yield
In dichloromethane	90%

5-hexenoyl chloride (36394-07-7) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → hex-5-enoic acid 2-thioxo-2H-pyridin-1-yl ester (197148-70-2)

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	90%

bismuth(III) chloride + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → [BiIII(mpo)3]

Conditions	Yield
In methanol for 20h; Reflux;	90%

N-Acetyl-N-methylcarbamoyl chloride (21777-48-0) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → 1-<(N-Acetyl-N-methylcarbamoyl)oxy>-2(1H)-pyridinethione (144809-63-2)

Conditions	Yield
In dichloromethane for 4h;	89%
In benzene for 1.5h;

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + propyl bromide (106-94-5) → 2-(n-propylthio)pyridine N-oxide (122333-44-2)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 2h;	89%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + 2-((1R,2S)-2-Phenyl-cyclobutyl)-propionic acid → 2-(cis-2-phenylcyclobutyl)propanoic acid 2-thioxo-2H-pyridin-1-yl ester

Conditions	Yield
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-mercaptopyridine-1-oxide sodium salt (3811-73-2) → 1,3-diphenyl-2-(2'-pyridylthio)-propane (102720-53-6)

Conditions	Yield
dmap In chlorobenzene at 133℃; for 2.5h;	88%

valproyl chloride (2936-08-5) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → N-(1-propylbutanoyloxy)-2-pyridinethione (173776-81-3)

Conditions	Yield
In dichloromethane	88%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + dimethyltin dichloride (753-73-1) → [Me2SnCl(2-pyridinethiolato-N-oxide)]

Conditions	Yield
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) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → 2-(n-butylthio)pyridine N-oxide (122333-47-5)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 2h;	87%

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + 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 2-thioxo-2H-pyridin-1-yl ester (184374-74-1)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	87%

nickel(II) chloride hexahydrate + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → bis(2-mercaptopyridine N-oxide) nickel(II)

Conditions	Yield
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] + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → C16H12N2OPtS

Conditions	Yield
In ethanol at 20℃; for 2h; Inert atmosphere;	87%

4-chloro-3,5-dinitrobenzotrifluoride (393-75-9) + 2-mercaptopyridine-1-oxide sodium salt (3811-73-2) → 2-<2,6-dinitro-4-trifluoromethylphenylthio>pyridine N-oxide

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

Upstream product

• 381173-14-4 N,N-dibenzyl-5-(3-methoxyphenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 381172-65-2 2-{[1-(4-ethoxyphenyl)-4-(4-methoxybenzylidene)-5-oxo-4,5-dihydro-1H-imidazol-2-yl]sulfanyl}-N-isopropyl-N-phenylacetamide 
• 381172-02-7 6-{3-ethoxy-4-[2-(3-methylphenoxy)ethoxy]benzylidene}-5-imino-2-isopropyl-5,6-dihydro-7H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-one 
• 381171-73-9 methyl 2-{[1-(ethoxycarbonyl)-2,2,2-trifluoro-1-(pentanoylamino)ethyl]amino}-4-ethyl-5-methyl-3-thiophenecarboxylate 
• 381171-69-3 N-phenyl-N-(4-phenyl-3-(3-pyridinylmethyl)-1,3-thiazol-2(3H)-ylidene)amine 
• 381171-66-0 2-[(1H-benzimidazol-2-ylmethyl)sulfanyl]-5,6-dimethyl-3-phenylthieno[2,3-d]pyrimidin-4(3H)-one 
• 381171-44-4 1-{[2-(4-chlorophenyl)-2-oxoethyl]sulfanyl}-4-(2-methylphenyl)-6,7,8,9-tetrahydro[1]benzothieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-one 
• 381171-24-0 5-imino-2-isopropyl-6-{3-methoxy-4-[2-(4-methylphenoxy)ethoxy]benzylidene}-5,6-dihydro-7H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-one 
• 381171-05-7 N-(2-hydroxyphenyl)-N'-(2-thienylcarbonyl)thiourea 
• 3811-71-0 DIANIL BROWN 3GN 
• 381170-97-4 2-(4-chlorophenyl)-3-[3-(4-iodophenoxy)propyl]-4(3H)-quinazolinone 
• 381170-85-0 2-(4-nitrobenzamido)-N-((tetrahydrofuran-2-yl)methyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 381170-57-6 2-(2,4-dichlorophenyl)-3-(1-naphthyl)-4(3H)-quinazolinone 
• 381170-43-0 2-(2,4-dichlorophenyl)-2-oxoethyl 2-pyrazinecarboxylate 

Downstream Products

• 381173-25-7 2-(2-(2,6-dimethylphenoxy)acetamido)-N-((tetrahydrofuran-2-yl)methyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 
• 381173-68-8 ethyl 2-(2,5-dichloroanilino)-3,3,3-trifluoro-2-[(phenylsulfonyl)amino]propanoate 
• 381173-86-0 3-(2-methoxyphenyl)-2-(4-methoxyphenyl)-4(3H)-quinazolinone 
• 381174-43-2 6-(5-bromo-2-hydroxybenzylidene)-5-imino-2-isopropyl-5,6-dihydro-7H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-one 
• 381174-81-8 2-[2-(2,6-dichlorobenzylidene)hydrazino]-4-(methoxymethyl)-6-methylnicotinonitrile 
• 38117-49-6 4-(METHOXYCARBONYL)-1-METHYLPYRIDINIUM 
• 381174-96-5 6-(9-anthrylmethylene)-5-imino-3-phenyl-5,6-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidin-7-one 
• 381174-99-8 methyl 2-(benzoylamino)-3,3,3-trifluoro-2-(pyridin-2-ylamino)propanoate 
• 381175-08-2 5-FURAN-2-YL-7-TRIFLUOROMETHYL-4,5,6,7-TETRAHYDRO-PYRAZOLO[1,5-A]PYRIMIDINE-2-CARBOXYLIC ACID 
• 381175-11-7 6-{3-ethoxy-4-[(4-fluorobenzyl)oxy]benzylidene}-5-imino-2-isopropyl-5,6-dihydro-7H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-one 
• 3811-75-4 HEXAMIDINE 
• 38117-54-3 CYCLOPENTADIENYLIRON DICARBONYL DIMER 
• 381175-94-6 2-(4-chlorobenzoyl)-N,N-diethylbenzamide 
• 381176-20-1 6-{3-ethoxy-4-[(2-fluorobenzyl)oxy]benzylidene}-5-imino-3-phenyl-5,6-dihydro-7H-[1,3]thiazolo[3,2-a]pyrimidin-7-one 

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