Product Name

  • Name

    Sulfadiazine

  • EINECS 200-685-8
  • CAS No. 68-35-9
  • Article Data29
  • CAS DataBase
  • Density 1.496 g/cm3
  • Solubility Very slightly soluble in cold water
  • Melting Point 254 °C
  • Formula C10H10N4O2S
  • Boiling Point 512.6 °C at 760 mmHg
  • Molecular Weight 250.281
  • Flash Point 263.8 °C
  • Transport Information
  • Appearance White to slightly yellow crystalline powder
  • Safety 26-36
  • Risk Codes 22-36/37/38-42/43
  • Molecular Structure Molecular Structure of 68-35-9 (Sulfadiazine)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms Sulfanilamide,N1-2(1H)-pyrimidinylidene- (6CI);Sulfanilamide, N1-2-pyrimidinyl- (8CI);2-(4-Aminobenzenesulfonylamino)pyrimidine;2-(p-Aminobenzenesulfonamido)pyrimidin;4-Amino-N-(2-pyrimidinyl)benzenesulfonamide;4-[[(Pyrimidin-2-yl)amino]sulfonyl]aniline;Adiazine;Cremodiazine;Debenal;Deltazina;Di-Azo-Mul;Diazin;Diazovit;Diazyl;Lipo-Levazine;Liquadiazine;N1-2-Pyrimidylsulfanilamide;Neazine;Pirimal;Pyrimal;RP 2616;Spofadrizine;Sterazine;Sulfadiazine;Sulfapirimidin;Sulfazin (Russian pharmaceutical);Sulfazine;Sulfolex;Sulphadiazine E;Sulfadiazine (SD);
  • PSA 106.35000
  • LogP 2.59460

Synthetic route

2-aminopyrimidine
109-12-6

2-aminopyrimidine

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
Stage #1: 2-aminopyrimidine; p-acetylaminobenzenesulfonyl chloride With calcium carbonate In toluene at 20 - 65℃;
Stage #2: With water; sodium hydroxide In toluene at 100 - 115℃;
Stage #3: With acetic acid pH=5 - 5.5; Reagent/catalyst;
98.5%
Stage #1: 2-aminopyrimidine; p-acetylaminobenzenesulfonyl chloride With pyridine In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;
Stage #2: With sodium hydroxide for 2h; Inert atmosphere; Reflux;
65%
Stage #1: 2-aminopyrimidine; p-acetylaminobenzenesulfonyl chloride With pyridine In tetrahydrofuran at 20℃; for 6h;
Stage #2: With sodium hydroxide for 2h; Reflux;
N-benzylidene-sulfanilic acid pyrimidin-2-ylamide
77218-33-8

N-benzylidene-sulfanilic acid pyrimidin-2-ylamide

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With water In acetone at 20℃; for 0.666667h; Irradiation;98%
4-amino-N-(diaminomethylene) benzenesulfonamide
57-67-0

4-amino-N-(diaminomethylene) benzenesulfonamide

3-ethoxyacrolein
19060-08-3

3-ethoxyacrolein

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
In ethanol at 100℃; for 4h; Green chemistry;91%
3-butoxyacrolein
4652-39-5

3-butoxyacrolein

4-amino-N-(diaminomethylene) benzenesulfonamide
57-67-0

4-amino-N-(diaminomethylene) benzenesulfonamide

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
In butan-1-ol at 100℃; for 4h; Green chemistry;90.8%
Malondialdehyde
542-78-9

Malondialdehyde

1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene
57-67-0

1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With sodium methylate In methanol at 65℃; for 2h; Temperature;89%
3-methoxyacrolein
4652-35-1

3-methoxyacrolein

4-amino-N-(diaminomethylene) benzenesulfonamide
57-67-0

4-amino-N-(diaminomethylene) benzenesulfonamide

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
In methanol at 100℃; for 4h; Temperature; Green chemistry;87%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

3-(4-acetylamino-benzenesulfonyl)-2-benzenesulfonylimino-2,3-dihydro-thiazole
101570-35-8

3-(4-acetylamino-benzenesulfonyl)-2-benzenesulfonylimino-2,3-dihydro-thiazole

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
und anschliessenden Erhitzen mit wss. NaOH;
2-aminopyrimidine
109-12-6

2-aminopyrimidine

phenyl-methanesulfonic acid-[3-(N-acetyl-sulfanilyl)-3H-thiazol-2-ylidenamide]

phenyl-methanesulfonic acid-[3-(N-acetyl-sulfanilyl)-3H-thiazol-2-ylidenamide]

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
und anschliessenden Erhitzen mit wss. NaOH;
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

sulfanilamide
63-74-1

sulfanilamide

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With potassium carbonate
2-phenoxypyrimidine
18213-90-6

2-phenoxypyrimidine

sulfanilamide
63-74-1

sulfanilamide

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With potassium carbonate
4-nitro-N-pyrimidin-2-ylbenzenesulfonamide
24265-24-5

4-nitro-N-pyrimidin-2-ylbenzenesulfonamide

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With hydrogenchloride; iron
With palladium 10% on activated carbon In tetrahydrofuran; methanol; ethyl acetate at 50℃; under 37503.8 Torr;
With hydrogenchloride; iron
4'-(pyrimidin-2-ylsulfamoyl)acetanilide
127-74-2

4'-(pyrimidin-2-ylsulfamoyl)acetanilide

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With calcium hydroxide
With hydrogenchloride
With sodium hydroxide
With sodium hydroxide In methanol; 1,2-dimethoxyethane at 120℃; for 16h;
With sodium hydroxide
<35S>sulfanilic acid pyrimidin-2-ylamide

<35S>sulfanilic acid pyrimidin-2-ylamide

sulfadiazine
68-35-9

sulfadiazine

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: aq. NaOH solution
View Scheme
Multi-step reaction with 2 steps
1: pyridine / acetonitrile / 3.08 h / 60 °C
2: sodium hydroxide / methanol; 1,2-dimethoxyethane / 16 h / 120 °C
View Scheme
AgC10H9N4O2S*2(1-(3-hydroxy-phenyl)-2-methylamino-ethanol)

AgC10H9N4O2S*2(1-(3-hydroxy-phenyl)-2-methylamino-ethanol)

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With mineral acids byproducts: amin-salt; dild. acids;
With mineral acids byproducts: Ag-salt; concd. acids;
With mineral acids byproducts: Ag-salt; concd. acids;
With mineral acids byproducts: amin-salt; dild. acids;
AgC10H9N4O2S*2ethylamine

AgC10H9N4O2S*2ethylamine

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With mineral acids byproducts: Ag-salt; concd. acids;
With mineral acids byproducts: Ag-salt; concd. acids;
Multi-step reaction with 3 steps
1: mineral acids
3: mineral acids
View Scheme
AgC10H9N4O2S*2benzylamine

AgC10H9N4O2S*2benzylamine

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With mineral acids byproducts: Ag-salt; concd. acids;
With mineral acids byproducts: Ag-salt; concd. acids;
Multi-step reaction with 3 steps
1: mineral acids
3: mineral acids
View Scheme
AgC10H9N4O2S*2morpholine

AgC10H9N4O2S*2morpholine

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With mineral acids byproducts: Ag-salt; dild. acids;
With mineral acids byproducts: Ag-salt; concd. acids;
With mineral acids byproducts: Ag-salt; concd. acids;
AgC10H9N4O2S*2ethylenediamine

AgC10H9N4O2S*2ethylenediamine

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With mineral acids byproducts: Ag-salt; concd. acids;
With mineral acids byproducts: Ag-salt; concd. acids;
Multi-step reaction with 3 steps
1: mineral acids
3: mineral acids
View Scheme
Ag(1+)*C10H9N4O2S(1-)*2NH3=AgC10H9N4O2S*2NH3

Ag(1+)*C10H9N4O2S(1-)*2NH3=AgC10H9N4O2S*2NH3

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
With mineral acids byproducts: Ag-salt; concd. acids;
With mineral acids byproducts: Ag-salt; concd. acids;
Multi-step reaction with 3 steps
1: mineral acids
3: mineral acids
View Scheme
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 100 °C
2: palladium 10% on activated carbon / methanol; ethyl acetate; tetrahydrofuran / 50 °C / 37503.8 Torr
View Scheme
silver sulfadiazine
22199-08-2

silver sulfadiazine

sulfadiazine
68-35-9

sulfadiazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: mineral acids
View Scheme
Multi-step reaction with 2 steps
2: mineral acids
View Scheme
Multi-step reaction with 2 steps
2: mineral acids
View Scheme
sulfadiazine
68-35-9

sulfadiazine

Methacryloyl chloride
920-46-7

Methacryloyl chloride

methacrylate sulfadiazine
52205-02-4

methacrylate sulfadiazine

Conditions
ConditionsYield
With sodium hydroxide In water; acetone for 3h; Darkness;97%
sulfadiazine
68-35-9

sulfadiazine

2-hydroxynaphthalene-1-carbaldehyde
708-06-5

2-hydroxynaphthalene-1-carbaldehyde

(E)-4-(((2-hydroxynaphthalen-1-yl)methylene)amino)-N-(pyrimidin-2-yl)benzenesulfonamide

(E)-4-(((2-hydroxynaphthalen-1-yl)methylene)amino)-N-(pyrimidin-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With acetic acid In ethanol for 4h; Reflux;96.3%
In ethanol for 2.5h; Schiff Reaction; Reflux;62%
sulfadiazine
68-35-9

sulfadiazine

water
7732-18-5

water

cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

[cobalt(II)(sulfadiazine(-1H))2(H2O)2]
905593-88-6

[cobalt(II)(sulfadiazine(-1H))2(H2O)2]

Conditions
ConditionsYield
In water byproducts: Na acetate; Na salt of ligand dissolved in H2O; Co salt in H2O added dropwise with stirring at 40°C for 1 h; filtered; ppt. washed with H2O, MeOH and Et2O successively; dried under vac.; elem. anal.;96%
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

sulfadiazine
68-35-9

sulfadiazine

water
7732-18-5

water

[cobalt(II)(sulfadiazine(-1H))2(H2O)2]
905593-88-6

[cobalt(II)(sulfadiazine(-1H))2(H2O)2]

Conditions
ConditionsYield
In water byproducts: NaCl; Na salt of ligand dissolved in H2O; Co salt in H2O added dropwise with stirring at 40°C for 1 h; filtered; ppt. washed with H2O, MeOH and Et2O successively; dried under vac.; elem. anal.;96%
sulfadiazine
68-35-9

sulfadiazine

ethyl acetoacetate
141-97-9

ethyl acetoacetate

3-oxo-N-{4-[(pyrimidin-2-ylamino)sulphonyl]phenyl}butanamide
134477-88-6

3-oxo-N-{4-[(pyrimidin-2-ylamino)sulphonyl]phenyl}butanamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 3h;95%
at 140℃; for 0.25h;75%
methanol
67-56-1

methanol

sulfadiazine
68-35-9

sulfadiazine

cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

[cobalt(II)(sulfadiazine(-1H))2(methanol)2]
905593-87-5

[cobalt(II)(sulfadiazine(-1H))2(methanol)2]

Conditions
ConditionsYield
In methanol byproducts: Na acetate; Na salt of ligand dissolved in MeOH; Co salt in MeOH added dropwise withstirring at 40°C for 1 h; filtered; ppt. washed with H2O, MeOH and Et2O successively; dried under vac.; elem. anal.;95%
methanol
67-56-1

methanol

cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

sulfadiazine
68-35-9

sulfadiazine

[cobalt(II)(sulfadiazine(-1H))2(methanol)2]
905593-87-5

[cobalt(II)(sulfadiazine(-1H))2(methanol)2]

Conditions
ConditionsYield
In methanol byproducts: NaCl; Na salt of ligand dissolved in MeOH; Co salt in MeOH added dropwise withstirring at 40°C for 1 h; filtered; ppt. washed with H2O, MeOH and Et2O successively; dried under vac.; elem. anal.;95%
1-oxa-4-aza-spiro[4.4]nonane
176-29-4

1-oxa-4-aza-spiro[4.4]nonane

formaldehyd
50-00-0

formaldehyd

sulfadiazine
68-35-9

sulfadiazine

C18H23N5O3S
1208127-45-0

C18H23N5O3S

Conditions
ConditionsYield
In ethanol; water for 4h; Reflux;95%
sulfadiazine
68-35-9

sulfadiazine

1-n-butyl-3-methylimidazolim bromide
85100-77-2

1-n-butyl-3-methylimidazolim bromide

C8H15N2(1+)*C10H9N4O2S(1-)
1676076-90-6

C8H15N2(1+)*C10H9N4O2S(1-)

Conditions
ConditionsYield
Stage #1: 1-n-butyl-3-methylimidazolim bromide With Merck ion exchange resin III In water
Stage #2: sulfadiazine In water at 20℃; for 2h;
95%
sulfadiazine
68-35-9

sulfadiazine

3β-acetoxy-5α-androstan-17-one
1239-31-2

3β-acetoxy-5α-androstan-17-one

C31H40N4O4S
1346667-31-9

C31H40N4O4S

Conditions
ConditionsYield
With acetic acid at 120℃; for 0.166667h;94%
sulfadiazine
68-35-9

sulfadiazine

(E)-N-[(2-chloroquinolin-3-yl)methylene]-4-phenylthiazol-2-amine

(E)-N-[(2-chloroquinolin-3-yl)methylene]-4-phenylthiazol-2-amine

4-[{(Z)-(2-chloroquinolin-3-yl)(4-phenylthiazol-2-ylimino)methyl}diazenyl]-N-(pyrimidin-2-yl)benzenesulfonamide

4-[{(Z)-(2-chloroquinolin-3-yl)(4-phenylthiazol-2-ylimino)methyl}diazenyl]-N-(pyrimidin-2-yl)benzenesulfonamide

Conditions
ConditionsYield
Stage #1: sulfadiazine With sulfuric acid; sodium nitrite In water at 0 - 5℃; for 0.25h;
Stage #2: (E)-N-[(2-chloroquinolin-3-yl)methylene]-4-phenylthiazol-2-amine With sodium hydroxide In ethanol; water for 1h; pH=5 - 6; Cooling with ice;
93%
sulfadiazine
68-35-9

sulfadiazine

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

N-palmitoyl-sulfanilic acid pyrimidin-2-ylamide
103350-72-7

N-palmitoyl-sulfanilic acid pyrimidin-2-ylamide

Conditions
ConditionsYield
With pyridine for 48h; Ambient temperature;92%
sulfadiazine
68-35-9

sulfadiazine

2-Mercaptobenzothiazole
149-30-4

2-Mercaptobenzothiazole

C17H12N6O2S3

C17H12N6O2S3

Conditions
ConditionsYield
Stage #1: sulfadiazine With hydrogenchloride; sodium nitrite In ethanol at 0 - 5℃;
Stage #2: 2-Mercaptobenzothiazole With sodium hydroxide In ethanol at 5 - 20℃; for 6h;
92%
N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine
444731-74-2

N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine

sulfadiazine
68-35-9

sulfadiazine

4-((4-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-2-yl)amino)-N-(pyrimidin-2-yl)benzenesulfonamide
1572439-08-7

4-((4-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-2-yl)amino)-N-(pyrimidin-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 85℃;92%
sulfadiazine
68-35-9

sulfadiazine

1-octyl-3-methyl-imidazolium bromide

1-octyl-3-methyl-imidazolium bromide

C12H23N2(1+)*C10H9N4O2S(1-)
1676076-97-3

C12H23N2(1+)*C10H9N4O2S(1-)

Conditions
ConditionsYield
Stage #1: 1-octyl-3-methyl-imidazolium bromide With Merck ion exchange resin III In water
Stage #2: sulfadiazine In water at 20℃; for 2h;
92%
3-(4-bromophenyl)acrylic acid
1200-07-3

3-(4-bromophenyl)acrylic acid

sulfadiazine
68-35-9

sulfadiazine

N-[4-(pyrimidin-2-yl-sulfamoyl)phenyl]4-bromocinnamamide

N-[4-(pyrimidin-2-yl-sulfamoyl)phenyl]4-bromocinnamamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux;91%
sulfadiazine
68-35-9

sulfadiazine

O,O‐diethyl 2-iodoethoxymethylphosphonate

O,O‐diethyl 2-iodoethoxymethylphosphonate

diethyl (2-(4-(N-pyrimidin-2-ylsulfamoyl)phenylamino)ethoxy)methylphosphonate

diethyl (2-(4-(N-pyrimidin-2-ylsulfamoyl)phenylamino)ethoxy)methylphosphonate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 10 - 50℃; for 3h;91%
trans-chloroaquabis(dimethylglyoximato(1-))cobalt(III)

trans-chloroaquabis(dimethylglyoximato(1-))cobalt(III)

sulfadiazine
68-35-9

sulfadiazine

trans-chlorobis(dimethylglyoximato)(2-sulfanilamidopyrimidine)cobalt(III) monohydrate

trans-chlorobis(dimethylglyoximato)(2-sulfanilamidopyrimidine)cobalt(III) monohydrate

Conditions
ConditionsYield
With water In acetone react. at 75°C for 1 h; ppt.; elem. anal.;90%
With water In methanol react. at 75°C for 1 h; ppt.; elem. anal.;90%
trans-{Co(ONC(CH3)C(CH3)NOH)2(I)(H2O)}

trans-{Co(ONC(CH3)C(CH3)NOH)2(I)(H2O)}

sulfadiazine
68-35-9

sulfadiazine

trans-iodobis(dimethylglyoximato)(2-sulfanilamidopyrimidine)cobalt(III) trihydrate

trans-iodobis(dimethylglyoximato)(2-sulfanilamidopyrimidine)cobalt(III) trihydrate

Conditions
ConditionsYield
With water In methanol react. at 60°C; pptn. after several hours; filtration (glass filter); washing of the ppt. with MeOH, H2O, EtOH and ether; elem. anal.;90%
sulfadiazine
68-35-9

sulfadiazine

sulfamerazina
127-79-7

sulfamerazina

ammonia
7664-41-7

ammonia

copper(II) ion

copper(II) ion

[Cu(sulfadiazine(1-))1.34(sulfamerazine)0.66(H2O)(NH3)]

[Cu(sulfadiazine(1-))1.34(sulfamerazine)0.66(H2O)(NH3)]

Conditions
ConditionsYield
In methanol; water mixt. Cu(2+) salt and ligand was dissolved in MeOH, concd. ammonia soln.was added dropwise and stirred for 10 min; slow evapn. at room temp.; elem. anal.;90%
sulfadiazine
68-35-9

sulfadiazine

ammonia
7664-41-7

ammonia

copper(II) ion

copper(II) ion

[Cu(sulfadiazine(1-))2(H2O)(NH3)]

[Cu(sulfadiazine(1-))2(H2O)(NH3)]

Conditions
ConditionsYield
In methanol; water mixt. Cu(2+) salt and ligand was dissolved in MeOH, concd. ammonia soln.was added dropwise and stirred for 10 min; slow evapn. at room temp.; elem. anal.;90%
4-fluorocinnamic acid
459-32-5, 14290-66-5, 14290-86-9

4-fluorocinnamic acid

sulfadiazine
68-35-9

sulfadiazine

N-[4-(pyrimidin-2-yl-sulfamoyl)phenyl]4-fluorocinnamamide

N-[4-(pyrimidin-2-yl-sulfamoyl)phenyl]4-fluorocinnamamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux;90%
sulfadiazine
68-35-9

sulfadiazine

acetylacetone
123-54-6

acetylacetone

4-{2-[2,4-dioxopentan-3-ylidene]hydrazinyl}-N-(pyrimidin-2-yl)benzenesulfonamide
41095-18-5

4-{2-[2,4-dioxopentan-3-ylidene]hydrazinyl}-N-(pyrimidin-2-yl)benzenesulfonamide

Conditions
ConditionsYield
Stage #1: sulfadiazine With hydrogenchloride; sodium nitrite In water; acetic acid at 0 - 5℃;
Stage #2: acetylacetone With sodium acetate In ethanol; water; acetic acid at 0 - 20℃; for 2h;
90%
sulfadiazine
68-35-9

sulfadiazine

3-methyl-1-tosyl-1H-pyrazol-5(4H)-one
74467-58-6

3-methyl-1-tosyl-1H-pyrazol-5(4H)-one

4-(2-(3-methyl-5-oxo-1-tosyl-1H-pyrazol-4(5H)- ylidene)hydrazinyl)-N-(pyrimidin-2-yl)benzenesulfonamide

4-(2-(3-methyl-5-oxo-1-tosyl-1H-pyrazol-4(5H)- ylidene)hydrazinyl)-N-(pyrimidin-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate; sodium nitrite In ethanol; water at 0 - 5℃; for 1h;90%
1H-benzimidazol-2-acetonitrile
4414-88-4

1H-benzimidazol-2-acetonitrile

sulfadiazine
68-35-9

sulfadiazine

N-(4-(N-(pyrimidin-2-yl)sulfamoyl)phenyl)-1H-benzo[d]imidazole-2-carbohydrazonoyl cyanide

N-(4-(N-(pyrimidin-2-yl)sulfamoyl)phenyl)-1H-benzo[d]imidazole-2-carbohydrazonoyl cyanide

Conditions
ConditionsYield
Stage #1: sulfadiazine With hydrogenchloride; sodium nitrite In water at 0 - 70℃; for 0.0833333h;
Stage #2: 1H-benzimidazol-2-acetonitrile With sodium acetate In ethanol at 0 - 5℃;
90%
2-aminopyrimidine
109-12-6

2-aminopyrimidine

sulfadiazine
68-35-9

sulfadiazine

4-amino-N-(pyrimidine-2-yl)-3-(pyrimidine-2-yldiazenyl)benzene sulfonamide

4-amino-N-(pyrimidine-2-yl)-3-(pyrimidine-2-yldiazenyl)benzene sulfonamide

Conditions
ConditionsYield
Stage #1: 2-aminopyrimidine With hydrogenchloride; sodium nitrite In water at 0 - 5℃;
Stage #2: sulfadiazine With sodium hydroxide In water at 0 - 5℃; pH=7;
89.5%

Sulfadiazine Consensus Reports

Reported in EPA TSCA Inventory.

Sulfadiazine Specification

The Sulfadiazine, with the CAS registry number 68-35-9, is also known as Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-. It belongs to the product categories of Antibiotics for Research and Experimental Use; Biochemistry; Sulfonamides (Antibiotics for Research and Experimental Use). Its EINECS registry number is 200-685-8. This chemical's molecular formula is C10H10N4O2S and molecular weight is 250.277. Its IUPAC name is called 4-amino-N-pyrimidin-2-ylbenzenesulfonamide. Side effects reported for sulfadiazine include: nausea, upset stomach, loss of appetite, and dizziness. This chemical's classification codes are Anti-infective Agents; Antibacterial; Antiparasitic Agents; Antiprotozoal agents; Coccidiostats; Drug / Therapeutic Agent; Human Data; Reproductive Effect.

Physical properties of Sulfadiazine: (1)ACD/LogP: -0.12; (2)ACD/LogD (pH 5.5): -0.13; (3)ACD/LogD (pH 7.4): -0.66; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 19.93; (7)ACD/KOC (pH 7.4): 5.87; (8)#H bond acceptors: 6; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.679; (12)Molar Refractivity: 63.14 cm3; (13)Molar Volume: 167.2 cm3; (14)Surface Tension: 82.6 dyne/cm; (15)Density: 1.496 g/cm3; (16)Flash Point: 263.8 °C; (17)Enthalpy of Vaporization: 78.38 kJ/mol; (18)Boiling Point: 512.6 °C at 760 mmHg; (19)Vapour Pressure: 1.28E-10 mmHg at 25°C.

Preparation of Sulfadiazine: this chemical can be prepared by chaff iodate and nitro metformin. This reaction will need reagents acetyl groups benzene sulfo-chloride and pyridine.

Uses of Sulfadiazine: It eliminates bacteria that cause infections by stopping the production of folic acid inside the bacterial cell, and is commonly used to treat urinary tract infections (UTIs). In combination, sulfadiazine and pyrimethamine, can be used to treat toxoplasmosis, a disease caused by Toxoplasma gondii.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N
(2)InChI: InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,; (3)16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
(4)InChIKey: SEEPANYCNGTZFQ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 1800mg/kg/5D- (1800mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: HEMATURIA

ENDOCRINE: HYPOGLYCEMIA
Postgraduate Medical Journal. Vol. 53, Pg. 103, 1977.
child TDLo unreported 138mg/kg (138mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

KIDNEY, URETER, AND BLADDER: HEMATURIA

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
Postgraduate Medical Journal. Vol. 53, Pg. 103, 1977.
dog LD oral > 5gm/kg (5000mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 79, Pg. 354, 1943.
man TDLo oral 229mg/kg/8D-I (229mg/kg) GASTROINTESTINAL: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
Israel Journal of Medical Sciences. Vol. 6, Pg. 561, 1970.
mouse LD50 intraperitoneal 750mg/kg (750mg/kg)   "Handbook of Analytical Toxicology," Sunshine, I., ed., Cleveland, OH, Chemical Rubber Co., 1969Vol. -, Pg. 109, 1969.
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03347,
mouse LD50 oral 1500mg/kg (1500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 571, 1971.
mouse LD50 subcutaneous 1600mg/kg (1600mg/kg)   Drugs in Japan Vol. 6, Pg. 386, 1982.
rat LD50 intravenous 880mg/kg (880mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 211, Pg. 367, 1950.
rat LDLo intraperitoneal 446mg/kg (446mg/kg)   Klinische Wochenscrift. Vol. 27, Pg. 449, 1949

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