547-32-0

Basic information

• Product Name: Sodium sulfadiazine
• Synonyms: (n(sup1)-2-pyrimidinylsulfanilamido)-sodiu;2-sulfanilamidopyrimidinesodiumsalt;4-amino-n-2-pyrimidinyl-benzenesulfonamidmonosodiumsalt;monosodium2-sulfanilamidopyrimidine;n(sup1)-2-pyrimidinylsulfanilamidemonosodiumsalt;n(sup1)-2-pyrimidinyl-sulfanilamidmonosodiumsalt;n(sup1)-2-pyrimidinyl-sulfanilamidn(sup1)-sodiumderiv;sodiumsulfapyrimidine
• CAS NO: 547-32-0
• Molecular Formula: C₁₀H₉N₄O₂S*Na
• Molecular Weight: 272.26
• EINECS: 208-919-0
• Product Categories: API;pharmaceutical
• Mol File: 547-32-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 512.6oC at 760 mmHg
• Flash Point: 263.8oC
• Appearance: /
• Density: 1.496g/cm3
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• BRN: 4068213
• CAS DataBase Reference: Sodium sulfadiazine(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium sulfadiazine(547-32-0)
• EPA Substance Registry System: Sodium sulfadiazine(547-32-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-42/43
• Safety Statements: 22-26-36/37-45
• RIDADR: 3249
• WGK Germany: 3
• RTECS: WP2000000
• F: 10-21
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 547-32-0(Hazardous Substances Data)

Usage

Chemical Properties

White to yellow crystalline powder

Uses

Different sources of media describe the Uses of 547-32-0 differently. You can refer to the following data:
1. Sulfadiazine Sodium Salt can be used as reactant/reagent in preparation and crystal structure of aminophenyl sulfonamide tetrahalides, hydrochloride and hydrobromide cocrystals with iodine.
2. Sulfadiazine may be used as an internal standard for the determination of sulfapyridine in biological samples using high-performance liquid chromatography technique.

General Description

Soluble sulfadiazine is an anhydrous, white, colorless, crystallinepowder soluble in water (1:2) and slightly soluble inalcohol. Its water solutions are alkaline (pH 9–10) and absorbcarbon dioxide from the air, with precipitation of sulfadiazine.It is administered as a 5% solution in sterile waterintravenously for patients requiring an immediately highblood level of the sulfonamide.

InChI:InChI=1/C10H10N4O2S.Na/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10;/h1-7H,11H2,(H,12,13,14);/q;+1

Synthetic route

sulfadiazine (68-35-9) → poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0)

Conditions	Yield
With sodium hydroxide In ethanol; water Heating;

dichloro(1,5-cyclooctadiene)platinum(ll) (12080-32-9) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) + sodium N-methyl-N-phenyldithiocarbamate (39234-21-4) → [Pt(SD)(me-DTC)]

Conditions	Yield
Stage #1: dichloro(1,5-cyclooctadiene)platinum(ll); poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] In water for 1h; Reflux; Stage #2: sodium N-methyl-N-phenyldithiocarbamate In water for 3h; Reflux;	97%

silver (7440-22-4) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → silver sulfadiazine (22199-08-2)

Conditions	Yield
With sodium nitrate; nitric acid In water for 0.1h; Electrochemical reaction; Green chemistry;	97%

dichloro(1,5-cyclooctadiene)platinum(ll) (12080-32-9) + (N-ethyl-N'-phenyl-dithiocarbamato) sodium (13074-29-8) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → [Pt(SD)(et-DTC)]

Conditions	Yield
Stage #1: dichloro(1,5-cyclooctadiene)platinum(ll); poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] In water for 1h; Reflux; Stage #2: (N-ethyl-N'-phenyl-dithiocarbamato) sodium In water for 3h; Reflux;	92%

6-methoxy quinoline (5263-87-6) + cobalt(II) sulphate heptahydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Co(sulfadiazine)2(6-methoxyquinoline)2

Conditions	Yield
In methanol for 4h; Reflux;	89.1%

triphenyltetrazolium chloride (298-96-4) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → C19H15N4(1+)*C10H9N4O2S(1-)

Conditions	Yield
In methanol; water at 20℃; for 2h;	88%

zinc(II) chloride hexahydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Zn(sulfadiazine)2(H2O)2 (1096051-46-5)

Conditions	Yield
In water aq. Zn salt added to aq. Na salt of sulfadiazine; soln. stirred at 40°C for 3 h; cooled to room temp.; filtered under vac., washed with water; dried over CaCl2; elem. anal.;	87%

zinc(II) acetate tetrahydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Zn(sulfadiazine)2(H2O)2 (1096051-46-5)

Conditions	Yield
In water aq. Zn salt added to aq. Na salt of sulfadiazine; soln. stirred at 40°C for 3 h; cooled to room temp.; filtered under vac., washed with water; dried over CaCl2;	87%

dichloro bis(acetonitrile) palladium(II) (21264-30-2, 90243-59-7, 14592-56-4) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) + sodium N-methyl-N-phenyldithiocarbamate (39234-21-4) → [Pd(SD)(me-DTC)]

Conditions	Yield
Stage #1: dichloro bis(acetonitrile) palladium(II); poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] In water for 1h; Reflux; Stage #2: sodium N-methyl-N-phenyldithiocarbamate In water for 3h; Reflux;	85%

[Fe(N-(2-hydroxybenzyl)-N-(2-pyridylmethyl)(3-chloro)(2-hydroxy)propylamine)Cl2]*H2O + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → [(Cl)(sulfadiazine)Fe(III)(μ-N-(2-hydroxybenzyl)-N-(2-pyridylmethyl)(3-chloro)(2-hydroxy)propylamine)2Fe(III)(sulfadiazine)(Cl)]*2H2O

Conditions	Yield
In methanol; water Reflux;	85%

dichloro bis(acetonitrile) palladium(II) (21264-30-2, 90243-59-7, 14592-56-4) + (N-ethyl-N'-phenyl-dithiocarbamato) sodium (13074-29-8) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → [Pd(SD)(et-DTC)]

Conditions	Yield
Stage #1: dichloro bis(acetonitrile) palladium(II); poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] In water for 1h; Reflux; Stage #2: (N-ethyl-N'-phenyl-dithiocarbamato) sodium In water for 3h; Reflux;	84%

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → C30H32N8O4RuS2

Conditions	Yield
In methanol for 3h;	84%

[2,2]bipyridinyl (366-18-7) + cobalt(II) chloride hexahydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Co(sulfadiazine)22,2′-bipyridine

Conditions	Yield
In ethanol at 25℃; for 1h;	81.4%

copper(II) choride dihydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Cu(sulfadiazine)2(H2O)2 (1096051-43-2)

Conditions	Yield
In methanol to soln. of Na salt of sulfadiazine, Cu salt added dropwise; soln. stirred continuously at 40°C for 3 h; cooled to room temp.; filtered under vac.; washed with water or methanol; elem. anal.;	80%
In water to soln. of Na salt of sulfadiazine, Cu salt added dropwise; soln. stirred continuously at 40°C for 3 h; cooled to room temp.; filtered under vac.; washed with water or methanol;	80%

copper(II) acetate dihydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Cu(sulfadiazine)2(H2O)2 (1096051-43-2)

Conditions	Yield
In methanol to soln. of Na salt of sulfadiazine, Cu salt added dropwise; soln. stirred continuously at 40°C for 3 h; cooled to room temp.; filtered under vac.; washed with water or methanol;	80%
In water to soln. of Na salt of sulfadiazine, Cu salt added dropwise; soln. stirred continuously at 40°C for 3 h; cooled to room temp.; filtered under vac.; washed with water or methanol;	80%

copper(ll) sulfate pentahydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Cu(sulfadiazine)2(H2O)2 (1096051-43-2)

Conditions	Yield
In methanol to soln. of Na salt of sulfadiazine, Cu salt added dropwise; soln. stirred continuously at 40°C for 3 h; cooled to room temp.; filtered under vac.; washed with water or methanol;	80%
In water to soln. of Na salt of sulfadiazine, Cu salt added dropwise; soln. stirred continuously at 40°C for 3 h; cooled to room temp.; filtered under vac.; washed with water or methanol;	80%

ammonium hydroxide + cadmium(II) acetate (543-90-8) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Cd(sulfadiazinato)2*2(NH3)

Conditions	Yield
In water Cd(II) acetate in distd. water added dropwise with stirring; stirred (18 h, room temp.); filtered off; air dried; crystd. (NH4OH-H2O, 1:1); elem. anal.;	80%

nickel(II) chloride hexahydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Ni(sulfadiazine)2(H2O)2*2H2O

Conditions	Yield
In water to aq. NiCl2*6H2O, aq. Na salt of sulfadiazine added; stirred at 40°C for 3 h; filtered under vac., washed with water; dried over CaCl2; elem. anal.;	78%

vanadyl(IV) sulphate pentahydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → VO(sulfadiazine)2(H2O)*H2O

Conditions	Yield
In water Pt compd. dissolved in water; then aq. soln. of Na salt of sulfadiazine added; mixt. stirred at 40°C for 3 h; filtered under vac., washed with water, dried over CaCl2; elem. anal.;	68%

manganese(II) chloride tetrahydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Mn(sulfadiazine)2(H2O)2 (1096051-49-8)

Conditions	Yield
In water to aq. Na salt of sulfadiazine added aq. MnCl2*4H2O; mixt. stirred for 3h at 40°C; cooled to room temp.; filtered under vac.; washed with water; dried over CaCl2; elem. anal.;	64%

methanol (67-56-1) + potassium tetrachloropalladate(II) (10025-98-6) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Pd(sulfadiazine)(CH3OH)Cl (1096051-55-6)

Conditions	Yield
In methanol; water Pd compd. dissolved in water; then MeOH soln. of Na salt of sulfadiazineadded; mixt. stirred at 40°C for 3 h; filtered under vac., washed with water, dried over CaCl2; elem. anal.;	56%

potassium tetrachloroplatinate(II) (10025-99-7) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → Pt(sulfadiazine)(H2O)Cl (1096051-58-9)

Conditions	Yield
In methanol; water Pt compd. dissolved in water; then MeOH soln. of Na salt of sulfadiazineadded; mixt. stirred at 40°C for 3 h; filtered under vac., washed with water, dried over CaCl2; elem. anal.;	53%

[{(η5-C5Me5)RhCl(acetone)}2](CF3SO3) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → C30H33N8O4RhS2

Conditions	Yield
In methanol; dichloromethane at 55℃; for 4h;	44%

[Zinc(II)(2-hydroxybenzyl-(2-pyridylmethyl)amine)Cl2] (760147-40-8) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → C46H44N12O6S2Zn2*4H2O

Conditions	Yield
In methanol; water	38%

water (7732-18-5) + nickel diacetate (373-02-4, 14998-37-9, 33025-09-1, 94044-50-5, 98268-31-6) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → C20H22N8NiO6S2 (1096252-90-2)

Conditions	Yield
In methanol for 3h; Reflux;	35%

chloromethyl benzoate (5335-05-7) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → 4-amino-N-benzoyloxymethyl-N-(2-pyrimidinyl)benzenesulfonamide

Conditions	Yield
In tetrahydrofuran Substitution;	30%

zinc(II) chloride dihydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → C20H21ClN8O5S2Zn

Conditions	Yield
In methanol; water	18%

mercury(II) diacetate (1600-27-7) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → [mercury(II)(sulfadiazine(-H))2(dimethylformamide)2]

Conditions	Yield
With NH3 In methanol Na-salt of organic ligand dissolved in hot CH3OH; 2 equiv. of CH3OH soln. of Hg(CH3COO)2 added with constant stirring; stirred for 6 h; filtered; dried over silica gel in desiccator; dissolved in DMF; few drops of NH3 added; stirred for 30 min; filtered; left crystallized for a few days; elem. anal.;

poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → sulfadiazine hydrochloride (24540-82-7)

Conditions	Yield
With hydrogenchloride In ethanol; water at 20℃; for 72h;

zinc(II) chloride hexahydrate + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) + ethylenediamine (107-15-3) → 2C10H9N4O2S(1-)*C6H24N6Zn(2+)*H2O

Conditions	Yield
Stage #1: zinc(II) chloride hexahydrate; poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] In ethanol Stage #2: ethylenediamine In ethanol

Upstream product

• 68-35-9 sulfadiazine 

Downstream Products

• 1096051-49-8 Mn(sulfadiazine)2(H₂O)2 
• 22199-08-2 silver sulfadiazine 
• 1096252-90-2 C₂₀H₂₂N₈NiO₆S₂ 

Relevant articles and documents

Salt forms of sulfadiazine with alkali metal and organic cations

The structures of four salt forms of sulfadiazine (SDH) with alkali metal cations are presented. Three contain the deprotonated SD anion (C10H9N4O2S). These are the discrete complex diaqua{4-[(pyrimidin-2-ylazan

Characterization of silver sulfadiazine and related compounds.

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