Product Name

  • Name

    Sulfamonomethoxine

  • EINECS 624-483-8
  • CAS No. 1220-83-3
  • Article Data7
  • CAS DataBase
  • Density 1.465 g/cm3
  • Solubility Soluble in water at 10mg/ml with warming. Also soluble in ethanol or methanol
  • Melting Point 203-206 °C
  • Formula C11H12N4O3S
  • Boiling Point 513.2 °C at 760 mmHg
  • Molecular Weight 280.307
  • Flash Point 264.2 °C
  • Transport Information
  • Appearance white to off-white crystalline powder
  • Safety 26-36
  • Risk Codes 36/37/38-43
  • Molecular Structure Molecular Structure of 1220-83-3 (Sulfamonomethoxine)
  • Hazard Symbols IrritantXi
  • Synonyms Sulfanilamide,N1-(6-methoxy-4-pyrimidinyl)- (6CI,8CI);4-Methoxy-6-sulfanilamidopyrimidine;4-Sulfanilamido-6-methoxypyrimidine;6-Methoxy-4-sulfanilamidopyrimidine;6-Sulfanilamido-4-methoxypyrimidine;DJ 1550;DS 36;Daimeton;ICI 32525;N1-(6-Methoxy-4-pyrimidinyl)sulfanilamide;Ro 4-3476;
  • PSA 115.58000
  • LogP 2.60320

Synthetic route

4-Nitrobenzenesulfonamido-6-methoxypyrimidine
1748-50-1

4-Nitrobenzenesulfonamido-6-methoxypyrimidine

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

Conditions
ConditionsYield
With iron; ammonium chloride In water for 10h; Heating; Yield given;
4-nitrobenzenediazonium chloride
100-05-0

4-nitrobenzenediazonium chloride

benzo<b>thiophen-3-yl-glyoxal phenylhydrazone

benzo<b>thiophen-3-yl-glyoxal phenylhydrazone

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SO2 / CuSO4 / acetic acid / 6 - 20 °C
2: 92 percent / pyridine / 2 h / 56 - 58 °C
3: Fe, NH4Cl / H2O / 10 h / Heating
View Scheme
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

(+-)-2-amino-5-butyl-thiazol-4-one

(+-)-2-amino-5-butyl-thiazol-4-one

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / pyridine / 2 h / 56 - 58 °C
2: Fe, NH4Cl / H2O / 10 h / Heating
View Scheme
2,4,6-trimethylpyrylium chlorate(VII)
940-93-2

2,4,6-trimethylpyrylium chlorate(VII)

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

1-[4-(6-Methoxy-pyrimidin-4-ylsulfamoyl)-phenyl]-2,4,6-trimethyl-pyridinium; perchlorate

1-[4-(6-Methoxy-pyrimidin-4-ylsulfamoyl)-phenyl]-2,4,6-trimethyl-pyridinium; perchlorate

Conditions
ConditionsYield
In acetic acid for 2h; Heating;97%
sulfamonomethoxine
1220-83-3

sulfamonomethoxine

glycyrrhyzic acid

glycyrrhyzic acid

C75H92N12O22S3

C75H92N12O22S3

Conditions
ConditionsYield
pyridine; dicyclohexyl-carbodiimide In 1,4-dioxane at 20 - 22℃; for 24h; Condensation;90.4%
(E)-3-(4-methoxyphenyl)propenoyl chloride
34446-64-5, 42996-84-9

(E)-3-(4-methoxyphenyl)propenoyl chloride

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

p-methoxycinnamoyl sulfamonomethoxine

p-methoxycinnamoyl sulfamonomethoxine

Conditions
ConditionsYield
With pyridine In tetrahydrofuran for 25.5h; Cooling with ice;85%
sulfamonomethoxine
1220-83-3

sulfamonomethoxine

1,3-bis(N1-4-amino-6-methoxypyrimidinebenzenesulfonamide)-2,2,2,4,4,4-hexa-chlorocyclodiphosph(V)azane

1,3-bis(N1-4-amino-6-methoxypyrimidinebenzenesulfonamide)-2,2,2,4,4,4-hexa-chlorocyclodiphosph(V)azane

Conditions
ConditionsYield
With phosphorus pentachloride In benzene at 15℃; for 0.5h;81%
2,6-dimethyl-4-oxo-5-phenyl-1,3-oxazinium perchlorate
63673-58-5

2,6-dimethyl-4-oxo-5-phenyl-1,3-oxazinium perchlorate

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

4-(2,6-dimethyl-4-oxo-5-phenyl-4H-pyrimidin-1-yl)-N-(6-methoxy-pyrimidin-4-yl)-benzenesulfonamide; compound with perchloric acid

4-(2,6-dimethyl-4-oxo-5-phenyl-4H-pyrimidin-1-yl)-N-(6-methoxy-pyrimidin-4-yl)-benzenesulfonamide; compound with perchloric acid

Conditions
ConditionsYield
In acetic acid for 48h; Ambient temperature;65%
sulfamonomethoxine
1220-83-3

sulfamonomethoxine

(3R,5aS,6R,9R,10S,12R,12aR)-10-(3-bromopropoxy)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene
165068-34-8

(3R,5aS,6R,9R,10S,12R,12aR)-10-(3-bromopropoxy)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene

4-amino-N-(6-methoxypyrimidin-4-yl)-N-(3-((3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)propyl)benzenesulfonamide

4-amino-N-(6-methoxypyrimidin-4-yl)-N-(3-((3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)propyl)benzenesulfonamide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;56%
3-(o-methoxyphenyl)-2,6-dimethyl-4-oxo-1,3-oxazinium perchlorate

3-(o-methoxyphenyl)-2,6-dimethyl-4-oxo-1,3-oxazinium perchlorate

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

4-[5-(2-methoxy-phenyl)-2,6-dimethyl-4-oxo-4H-pyrimidin-1-yl]-N-(6-methoxy-pyrimidin-4-yl)-benzenesulfonamide; compound with perchloric acid

4-[5-(2-methoxy-phenyl)-2,6-dimethyl-4-oxo-4H-pyrimidin-1-yl]-N-(6-methoxy-pyrimidin-4-yl)-benzenesulfonamide; compound with perchloric acid

Conditions
ConditionsYield
In acetic acid for 48h; Ambient temperature;35%
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
80756-85-0

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)-N-(4-(N-(6-methoxypyrimidin-4-yl)sulfamoyl)phenyl)acetamide

(Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)-N-(4-(N-(6-methoxypyrimidin-4-yl)sulfamoyl)phenyl)acetamide

Conditions
ConditionsYield
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere;32.7%
sulfamonomethoxine
1220-83-3

sulfamonomethoxine

4-amino-N-(6-hydroxy-4-pyrimidinyl)benzenesulfonamide
14762-26-6

4-amino-N-(6-hydroxy-4-pyrimidinyl)benzenesulfonamide

Conditions
ConditionsYield
With sodium hydroxide for 14h; Heating;16%
With sodium hydroxide at 80 - 90℃; for 50h; Yield given;
2,2'-dithiodibenzoic acid dichloride
19602-82-5

2,2'-dithiodibenzoic acid dichloride

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

C36H30N8O8S4

C36H30N8O8S4

Conditions
ConditionsYield
With pyridine In 1,4-dioxane Ambient temperature;
tropaeolin O

tropaeolin O

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

C23H18N7O8S2(1-)*Na(1+)
1312665-65-8

C23H18N7O8S2(1-)*Na(1+)

Conditions
ConditionsYield
Stage #1: sulfamonomethoxine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h;
Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;
4-acetoxyferuloyl chloride
55882-65-0, 108608-07-7, 50906-12-2

4-acetoxyferuloyl chloride

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

C23H22N4O7S

C23H22N4O7S

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 0 - 20℃; for 6h;
4-acetoxyferuloyl chloride
55882-65-0, 108608-07-7, 50906-12-2

4-acetoxyferuloyl chloride

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

N1-feruloylsulfamonomethoxine

N1-feruloylsulfamonomethoxine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / tetrahydrofuran / 6 h / 0 - 20 °C
2: hydrogenchloride / tetrahydrofuran / 1 h / 60 °C
View Scheme
p-acetoxycinnamoyl chloride
53901-95-4, 108608-06-6, 58523-18-5

p-acetoxycinnamoyl chloride

sulfamonomethoxine
1220-83-3

sulfamonomethoxine

4-acetoxycinnamoyl sulfamonomethoxine

4-acetoxycinnamoyl sulfamonomethoxine

Conditions
ConditionsYield
With pyridine In tetrahydrofuran for 25.5h; Cooling with ice;

Sulfamonomethoxine Chemical Properties

Molecular Structure of Sulfamonomethoxine (CAS NO.1220-83-3):

IUPAC Name: 4-Amino-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide 
Molecular Formula: C11H12N4O3S
Molecular Weight: 280.302980 g/mol
XLogP3: 0.8
H-Bond Donor: 2
H-Bond Acceptor: 7
Canonical SMILES: COC1=NC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI: InChI=1S/C11H12N4O3S/c1-18-11-6-10(13-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,14,15)
InChIKey: WMPXPUYPYQKQCX-UHFFFAOYSA-N
Index of Refraction: 1.646
Molar Refractivity: 69.51 cm3
Molar Volume: 191.2 cm3
Surface Tension: 75 dyne/cm
Density: 1.465 g/cm3
Flash Point: 264.2 °C
Enthalpy of Vaporization: 78.46 kJ/mol
Boiling Point: 513.2 °C at 760 mmHg
Vapour Pressure: 1.2E-10 mmHg at 25 °C
Water Solubility: 4029 mg/L at 25 °C
BRN: 0621128

Sulfamonomethoxine Toxicity Data With Reference

1.    

orl-mus LD50:4680 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),391.
2.    

ivn-mus LD50:1010 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),391.

Sulfamonomethoxine Safety Profile

Safety Information of Sulfamonomethoxine (CAS NO.1220-83-3):
Hazard Symbols: Xi Irritant
Risk Codes: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Description: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36:Wear suitable protective clothing
Moderately toxic by intravenous route. Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.

Sulfamonomethoxine Specification

  Sulfamonomethoxine with CAS registry number of 1220-83-3 is also known as 5-25-12-00493 (Beilstein Handbook Reference) ; DJ-1550 ; DS-36 ; Daimeton ; ICI 32525 ; N(sup 1)-(6-Methoxy-4-pyrimidinyl)sulfanilamide ; N1-(6-Methoxy-4-pyrimidinyl)sulfanilamide ; Ro 4-3476 ; Sulfamonomethoxin ; Sulfamonomethoxinum ; Sulfamonomethoxinum [INN-Latin] ; Sulfamonometoxina ; Sulfamonometoxina [INN-Spanish] ; Sulfamonomethoxine [USAN:INN:BAN:JAN] ; Sulfanilamide, N(sup 1)-(6-methoxy-4-pyrimidinyl)- ; UNII-U700P169W2 ; Benzenesulfonamide, 4-amino-N-(6-methoxy-4-pyrimidinyl)- . It is a sulfonamide for the treatment of infections caused by hemolytic streptococcus, pneumococcal, meningococcal.

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