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Basic Information
CAS No.: 122-11-2
Name: Sulfadimethoxine
Molecular Structure:
Molecular Structure of 122-11-2 (Sulfadimethoxine)
Formula: C12H14N4O4S
Molecular Weight: 310.334
Synonyms: Sulfanilamide,N1-(2,6-dimethoxy-4-pyrimidinyl)- (6CI,8CI);2,4-Dimethoxy-6-sulfanilamido-1,3-diazine;2,4-Dimethoxy-6-sulfanilamido-1,3-pyrimidine;2,4-Dimethoxy-6-sulfanilamidopyrimidine;2,6-Dimethoxy-4-sulfanilamidopyrimidine;4-Sulfa-2,6-dimethoxypyrimidine;4-Sulfanilamido-2,6-dimethoxypyrimidine;6-Sulfanilamido-2,4-dimethoxy-1,3-diazine;Abcid;Agribon;Albon;Arnosulfan;Bactrovet;Deposul;Diasulfa;Dimethoxysulfadiazine;Dinosol;Dorisul;Fuxal;Lasibon;Madribon;Madrigid;Madriqid;Madroxin;Madroxine;Maxulvet;Mecozine;Metoxidon;N-(2,6-Dimethoxypyrimidin-4-yl)-4-aminobenzenesulfonamide;N1-(2,6-Dimethoxy-4-pyrimidinyl)sulfanilamide;NSC 683544;Neostreptal;Omnibon;Persulfen;Redifal;
EINECS: 204-523-7
Density: 1.441 g/cm3
Melting Point: 200 °C
Boiling Point: 548.5 °C at 760 mmHg
Flash Point: 285.5 °C
Solubility: 46.3mg/L(37 oC)
Appearance: yellow to straw yellow powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38-43
Safety: 26-36/37-24/25-23
PSA: 124.81000
LogP: 2.61180
Synthetic route
555-25-9

4-p-acetamidobenzenesulfonamido-2,6-dimethoxypyrimidine

122-11-2

sulfadimethoxine

Conditions
ConditionsYield
With methanol; sodium hydroxide at 85℃; for 6h; Temperature; Large scale;96%
With sodium hydroxide
37063-70-0

N-(2,6-dimethoxy-pyrimidin-4-yl)-4-nitro-benzenesulfonamide

122-11-2

sulfadimethoxine

Conditions
ConditionsYield
With iron; ammonium chloride In water for 10h; Heating;81.3%
77767-96-5

Trimethyl-4-(2,6-dimethoxypyrimidinyl)ammoniumchlorid

sodium-salt of sulfanilamide

sodium-salt of sulfanilamide

122-11-2

sulfadimethoxine

Conditions
ConditionsYield
With acetamide
100-05-0

4-nitrobenzenediazonium chloride

benzothiophen-3-yl-glyoxal phenylhydrazone

benzothiophen-3-yl-glyoxal phenylhydrazone

122-11-2

sulfadimethoxine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SO2 / CuSO4 / acetic acid / 6 - 20 °C
2: 84.2 percent / pyridine / 2 h / 56 - 58 °C
3: 81.3 percent / Fe, NH4Cl / H2O / 10 h / Heating
View Scheme
98-74-8

4-Nitrobenzenesulfonyl chloride

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

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

122-11-2

sulfadimethoxine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84.2 percent / pyridine / 2 h / 56 - 58 °C
2: 81.3 percent / Fe, NH4Cl / H2O / 10 h / Heating
View Scheme
3289-50-7

2,6-dimethoxypyrimidin-4-amine

122-11-2

sulfadimethoxine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: aqueous NaOH
View Scheme
121-60-8

p-acetylaminobenzenesulfonyl chloride

122-11-2

sulfadimethoxine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: aqueous NaOH
View Scheme
122-11-2

sulfadimethoxine

15186-48-8

2,3-isopropylidene-glyceraldehyde

N-(2,6-dimethoxypyrimidin-4-yl)-4-({[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}amino)benzenesulfonamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dimethyl sulfoxide; toluene Condensation;100%
122-11-2

sulfadimethoxine

920-46-7

Methacryloyl chloride

sulfadimethoxine methacrylamide

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 20℃; for 1.5h; Cooling with ice;97%
With sodium hydroxide In acetone at 20℃; for 12h;96.2%
With sodium hydroxide In water; acetone at 0℃;85%
With sodium hydroxide In acetone at 0℃;
122-11-2

sulfadimethoxine

1571-08-0

methyl 4-formylbenzoate

446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

methyl 4-(cyclohexyl((4-(N-(2,6-dimethoxypyrimidin-4-yl)sulfamoyl)phenyl)amino)methyl)benzoate

Conditions
ConditionsYield
With sodium hydrogen sulfate; Ir(dF(CF3)ppy)2(bpy)PF6 In 1,4-dioxane at 24℃; for 24h; Petasis Reaction; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;97%
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Chemistry

1.IUPAC Name:   4-Amino-N-(2,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
2.Synonyms: 2,4-Dimethoxy-6-sulfanilamido-1,3-diazine ; 2,6-Dimethoxy-4-(p-aminobenzenesulfonamido)pyrimidine ; 2,6-Dimethoxy-4-sulfanilamidopyrimidine ; 4-Amino-n-(2,6-dimethoxy-4-pyrimidinyl)-benzenesulfonamid ; Abcid ; Agribon ; Albon ; Arnosulfan
3.The Molecular Formula of  6-Sulfanilamido-2,4-dimethoxy-pyrimidine (122-11-2) :C12H14N4O4S
4.The Molecular Weight of   6-Sulfanilamido-2,4-dimethoxy-pyrimidine (122-11-2) :310.329 g/mol
5.The Molecular Structure of   6-Sulfanilamido-2,4-dimethoxy-pyrimidine (122-11-2):
6.Index of Refraction: 1.622
7.Molar Refractivity: 75.87 cm3
8.Molar Volume: 215.2 cm3
9.Polarizability: 10-24cm3
10.Surface Tension: 69.5 dyne/cm
11.Density: 1.441 g/cm3
12.Flash Point: 285.5 °C
13.Enthalpy of Vaporization: 82.81 kJ/mol
14.Boiling Point: 548.5 °C at 760 mmHg
15.Vapour Pressure: 4.41E-12 mmHg at 25°C 

Uses

      6-Sulfanilamido-2,4-dimethoxy-pyrimidine (122-11-2) can be used as anti-infective agent.

Toxicity Data With Reference

1.    

ipr-mus LD50:866 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),386.
2.    

scu-mus LD50:791 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),386.
3.    

ivn-mus LD50:844 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),386.
4.    

ivn-rbt LD50:1000 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),386.

Safety Profile

Moderately toxic by intraperitoneal, intravenous, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.
Hazard Codes: Xi
Risk Statements: 36/37/38-43
R36/37/38:  Irritating to eyes, respiratory system and skin
R43:  May cause sensitization by skin contact 
Safety Statements: 26-36/37-24/25-23
S26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37:  Wear suitable protective clothing and gloves
S24/25:  Avoid contact with skin and eyes
S23:  Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
WGK Germany: 3

 

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