Conditions | Yield |
---|---|
With hydrogen In methanol; ethyl acetate under 760.051 Torr; for 4h; Heating; Flow reactor; Green chemistry; | 99% |
With maghemite-palladium nanocomposite; hydrogen In ethanol; ethyl acetate at 30℃; for 0.0125h; | 98% |
With sodium tetrahydroborate In water at 20℃; for 0.5h; Green chemistry; | 98% |
4-azidobenzenesulfonamide
sulfanilamide
Conditions | Yield |
---|---|
With D-glucose; potassium hydroxide In water at 85℃; for 0.0833333h; Green chemistry; chemoselective reaction; | 99% |
(p-aminobenzene)sulfonyl azide
sulfanilamide
Conditions | Yield |
---|---|
With C24H21CuN3O3; sodium L-ascorbate In water; tert-butyl alcohol at 80℃; for 6h; Inert atmosphere; | 98% |
With C27H34ClN2ORu(1+)*Cl(1-); sodium formate In aq. phosphate buffer at 37℃; for 24h; pH=7.4; |
Conditions | Yield |
---|---|
Stage #1: chlorobenzene With chlorosulfonic acid; ammonium chloride In 1,2-dichloro-ethane at 55℃; for 4h; Stage #2: With ammonia In water; 1,2-dichloro-ethane at 15 - 40℃; for 2h; Stage #3: With copper(l) iodide In water; 1,2-dichloro-ethane at 160℃; for 12h; Reagent/catalyst; Temperature; | 97.5% |
1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene
A
bis(4-aminophenyl)disulfide
B
sulfanilamide
C
aniline
D
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
In methanol for 76h; Product distribution; Mechanism; Irradiation; λ=254 nm; | A n/a B 4.4% C 95.1% D 2.7% |
tert-butyl (4-sulfamoylphenyl)carbamate
sulfanilamide
Conditions | Yield |
---|---|
With H-β zeolite In dichloromethane for 10h; Heating; | 91% |
Conditions | Yield |
---|---|
Stage #1: Acetanilid With chlorosulfonic acid; thionyl chloride; phosphorus pentoxide In tetrachloromethane at 60 - 90℃; Stage #2: With ammonia In tetrachloromethane at 50℃; for 3h; | 86.98% |
Multi-step reaction with 3 steps 1.1: chlorosulfonic acid / 55 h / 40 °C 1.2: 3 h / 65 °C 2.1: ammonium hydroxide / 1,2-dichloro-ethane / 2.5 h / 15 - 40 °C / Large scale 3.1: sodium hydroxide / 3 h / 90 °C / Large scale View Scheme |
Conditions | Yield |
---|---|
With ammonia; dihydrogen peroxide In water; tert-butyl alcohol at 75℃; for 2h; Reagent/catalyst; Temperature; Molecular sieve; | 82.3% |
5-chloro-2,6-dimethyl-pyrimidin-4-ylamine
p-acetylaminobenzenesulfonyl chloride
A
N-[4-(dimethylamino-4-ylsulfonyl)phenyl]acetamide
B
sulfanilamide
C
Sulfaclomid
D
C22H22ClN5O6S2
E
4-(4'-Acetylaminobenzensulfonyl)amino-5-chlor-2,6-dimethylpyrimidin
Conditions | Yield |
---|---|
With trimethylamine In dichloromethane at 33 - 40℃; for 10h; Mechanism; Product distribution; further amines; | A n/a B n/a C n/a D 70% E n/a |
Conditions | Yield |
---|---|
With hydrogenchloride; water In ethanol for 1h; Reflux; | 68% |
With hydrogenchloride | |
With sodium hydroxide |
Conditions | Yield |
---|---|
With hydrogenchloride In water at 5℃; for 0.583333h; Reflux; | 60% |
sulphapyridine
A
2-aminopyridine
B
bis(4-aminophenyl)disulfide
C
p-nitrobenzenesulfonamide
D
sulfanilamide
E
aniline
F
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
In methanol for 48h; Product distribution; Mechanism; Irradiation; λ=254 nm; | A 15.6% B n/a C n/a D 6.1% E 29.1% F 20.1% |
Conditions | Yield |
---|---|
With ammonium hydroxide; copper; copper(II) sulfate at 150℃; under 44130.5 Torr; | |
With copper(I) oxide; ammonium hydroxide at 160℃; | |
With ammonium chloride; copper at 160℃; |
N-formyl-sulfanilyl chloride
sulfanilamide
Conditions | Yield |
---|---|
With ammonium hydroxide | |
Multi-step reaction with 2 steps 1: aqueous ammonia 2: aq. NaOH solution View Scheme |
Conditions | Yield |
---|---|
With sulfuric acid at 150℃; | |
With sodium hydroxide at 100℃; |
Conditions | Yield |
---|---|
With water | |
With ammonium hydroxide | |
With sulfuric acid | |
With sodium hydroxide | |
Multi-step reaction with 2 steps 2: ethanolic NaOH-solution View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
With alkaline aqueous sodium hypochlorite |
(E)-4-(phenyldiazenyl)benzenesulfonamide
sulfanilamide
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
(E)-4-(phenyldiazenyl)benzenesulfonamide
A
4-(N'-phenyl-hydrazino)-benzenesulfonic acid amide
B
sulfanilamide
Conditions | Yield |
---|---|
With sodium hydroxide; sodium dithionite |
Conditions | Yield |
---|---|
With Britton-Robinson buffer Rate constant; controlled potential electrolysis; |
p-<(8-hydroxy-5-quinolyl)azo>benzenesulphonamide
A
5-amino-8-hydroxyquinoline
B
sulfanilamide
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide for 1.5h; electrolysis at dropping mercury electrode; |
4-(2,4-dihydroxy-phenylazo)-benzenesulfonic acid amide
A
4-aminoresorcinol
B
sulfanilamide
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 2.25 to 10.12); |
4-(5-bromo-2-hydroxy-phenylazo)-benzenesulfonic acid amide
A
2-amino-4-bromo-phenol
B
sulfanilamide
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 3.22 to 10.00); |
4-(5-Formyl-2-hydroxy-phenylazo)-benzenesulfonamide
A
sulfanilamide
B
3-amino-4-hydroxybenzaldehyde
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 3.10 to 10.34); |
4-(2-Hydroxy-5-methoxy-phenylazo)-benzenesulfonamide
A
2-amino-4-methoxyphenol
B
sulfanilamide
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 2.03 to 10.00); |
4-(4-Dimethylamino-2-hydroxy-phenylazo)-benzenesulfonamide
A
2-amino-5-(dimethylamino)phenol
B
sulfanilamide
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 2.03 to 10.00); |
Conditions | Yield |
---|---|
at 20℃; for 1h; | 100% |
In ethanol at 20 - 70℃; for 0.0166667h; other time tested; |
sulfanilamide
4-azidobenzenesulfonamide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium azide; sodium nitrite In water at 0 - 5℃; for 1h; | 100% |
With hydrogenchloride; sodium azide; sodium nitrite In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 25℃; | 93% |
Stage #1: sulfanilamide With hydrogenchloride; sodium nitrite In tetrahydrofuran; water; N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With sodium azide In tetrahydrofuran; water; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 90.6% |
3-pyridinecarboxaldehyde
sulfanilamide
N4-(3-pyridylidene) sulfanilamide
Conditions | Yield |
---|---|
at 150 - 155℃; for 0.0833333h; | 100% |
In ethanol for 3h; Heating; |
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 0.5h; | 100% |
In 1,4-dioxane | 100% |
In 1,4-dioxane | 97% |
Conditions | Yield |
---|---|
In dichloromethane for 0.5h; Heating; | 100% |
methyl 2-chloroquinazoline-7-carboxylate
sulfanilamide
Conditions | Yield |
---|---|
In isopropyl alcohol at 90℃; for 2h; | 100% |
methyl 2-chloroquinazolin-6-carboxylate
sulfanilamide
Methyl 2-(4-sulfamoylphenylamino)quinazolin-6-carboxylate
Conditions | Yield |
---|---|
at 90℃; for 2h; | 100% |
di-tert-butyl dicarbonate
sulfanilamide
tert-butyl (4-sulfamoylphenyl)carbamate
Conditions | Yield |
---|---|
In 1,4-dioxane Reflux; | 100% |
With potassium hydroxide In tetrahydrofuran; water |
Conditions | Yield |
---|---|
With acetic acid In dichloromethane | 100% |
m-phenylenediamine
sulfanilamide
(E)-4-(2-(4-sulfonamido)diazenyl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Stage #1: sulfanilamide With hydrogenchloride; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: m-phenylenediamine With hydrogenchloride In water at 0℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 3,6-dichlorpyridazine; sulfanilamide In dimethyl sulfoxide at 100℃; under 2250.23 Torr; for 10h; Stage #2: With sodium In water at 60℃; for 8h; Solvent; Reagent/catalyst; | 99.5% |
2,5-hexanedione
sulfanilamide
4-(2,5-dimethyl-1H-pyrrol-1-yl)benzenesulfonamide
Conditions | Yield |
---|---|
With iodine at 20℃; for 2h; Paal-Knorr Pyrrole Synthesis; | 99% |
With acetic acid at 120℃; for 3h; | 86% |
at 180℃; for 0.25h; Paal-Knorr pyrrole synthesis; Microwave irradiation; | 75% |
With ethanol; acetic acid |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 15h; | 99% |
With triethylamine In acetonitrile at 0 - 5℃; | 35% |
With pyridine |
sulfanilamide
N-triethylgermylsulfanilamide
Conditions | Yield |
---|---|
In chloroform-d1 org. compd. addn. to Ge-compd. soln. in NMR tube; complete conversion after 24 h at 20°C ((1)H-NMR monitoring); | 99% |
Conditions | Yield |
---|---|
In acetonitrile for 24h; Inert atmosphere; Reflux; | 99% |
Conditions | Yield |
---|---|
With (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane; hydrogen In tetrahydrofuran at 100℃; under 15201 Torr; for 6h; Sealed tube; Molecular sieve; Autoclave; Green chemistry; | 99% |
With triethylsilane; palladium on carbon; TPGS-750-M In water at 45℃; for 12h; | 78% |
Multi-step reaction with 2 steps 1: chloroform; methanol / 18 h / Reflux 2: sodium tetrahydroborate / methanol / 4 h View Scheme | |
Multi-step reaction with 2 steps 1: formic acid / methanol / Reflux 2: sodium tetrahydroborate / methanol / 25 h / 0 - 25 °C View Scheme |
sulfanilamide
4-{[4-(4-hydroxyphenyl)pyrimidin-2-yl]amino}benzenesulfonamide
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 160℃; for 2h; Microwave irradiation; | 99% |
With hydrogenchloride In ethanol Microwave irradiation; | 99% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 1,4-dioxane; water Reflux; | 99% |
potassium thioacyanate
sulfanilamide
3-chloropentane-2,4-dione
5-Acetyl-4-methyl-2-<(p-sulphamylphenyl)amino>thiazole
Conditions | Yield |
---|---|
With silica sulfuric acid In neat (no solvent) at 20℃; for 0.416667h; Milling; Green chemistry; | 99% |
salicylaldehyde
sulfanilamide
4-[(2-hydroxybenzylidene)amino]benzenesulfonamide
Conditions | Yield |
---|---|
In ethanol for 0.333333h; Reflux; | 98.57% |
In ethanol at 60℃; Microwave irradiation; | 88% |
With formic acid In methanol Reflux; | 85% |
2,3-Dichloro-1,4-naphthoquinone
sulfanilamide
4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide
Conditions | Yield |
---|---|
In water for 3h; Reflux; | 98% |
In ethanol at 115℃; for 72h; | 38.9% |
With acetic acid; N,N-diethylaniline | |
In ethanol Reflux; |
N,N-dimethyl-formamide dimethyl acetal
sulfanilamide
4-amino-N-[(dimethylamino)methylidene]benzenesulfonamide
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; under 760.051 Torr; for 0.25h; Green chemistry; chemoselective reaction; | 98% |
sulfanilamide
chloroacetyl chloride
2-chloro-N-(4-sulfamoylphenyl)acetamide
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 0℃; | 98% |
With potassium carbonate In acetone at 0 - 20℃; | 95% |
In acetone at 20 - 95℃; for 1h; | 89% |
sulfanilamide
triphenylphosphine
N-<(p-aminophenyl)sulfonyl>triphenylphospha-λ5-azene
Conditions | Yield |
---|---|
With diethylazodicarboxylate In tetrahydrofuran at 0 - 25℃; for 12h; | 98% |
With diethylazodicarboxylate In tetrahydrofuran at 0℃; | 79% |
Conditions | Yield |
---|---|
In ethanol Substitution; Heating; | 98% |
tetrachlorophthalic anhydride
sulfanilamide
4-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)benzenesulfonamide
Conditions | Yield |
---|---|
With acetic acid at 130℃; for 2h; | 98% |
With acetic acid for 24h; Reflux; |
sulfanilamide
4-(bromoacetyl)toluene
4-((2-oxo-2-(p-tolyl)ethyl)amino)benzenesulfonamide
Conditions | Yield |
---|---|
In methanol for 4h; Reflux; | 98% |
The IUPAC name of Sulfanilamide is 4-aminobenzenesulfonamide. With the CAS registry number 63-74-1 and EINECS 200-563-4, it is also named as Benzenesulfonamide, p-amino-. The product's categories are Sulfonamides (Antibiotics for Research and Experimental Use); Antibiotics for Research and Experimental Use; Biochemistry. It is white to almost white crystalline powder which is alightly soluble in cold water, ethanol, methanol, ether and acetone, soluble in boiling water, glycerol, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene or petroleum ether. As an antibiotic, this chemical functions by competitively inhibiting (ie, by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA). Additionally, it should be sealed in the container and stored in the cool and dry place.
The other characteristics of Sulfanilamide can be summarized as:
(1)ACD/LogP: -0.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.72; (4)ACD/LogD (pH 7.4): -0.72; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 9.66; (8)ACD/KOC (pH 7.4): 9.66; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 49 Å2; (13)Index of Refraction: 1.627; (14)Molar Refractivity: 42.8 cm3; (15)Molar Volume: 120.6 cm3; (16)Surface Tension: 63.7 dyne/cm; (17)Enthalpy of Vaporization: 65.13 kJ/mol; (18)Vapour Pressure: 1.27E-06 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 172.030648; (21)MonoIsotopic Mass: 172.030648; (22)Topological Polar Surface Area: 94.6; (23)Heavy Atom Count: 11; (24)Complexity: 211.
Preparation of Sulfanilamide:
It can be obtained by chlorosulfonation, amination, hydrolysis and neutralization of acetanilide.
Uses of Sulfanilamide:
It is not only used as reagent in the determination of nitrite, but also used in the pharmaceutical industry. It is also the major raw material in the production of sulfonamides drug. What's more, it is used in organic synthesis. For example, it can react with furfural to get 4-(2-formyl-pyrrol-1-yl)-benzenesulfonic acid amide. This reaction needs reagent 2N-HCl and solvent ethanol by heating. The reaction time is 5 hours. The yield is 41%.
When you are using Sulfanilamide, please be cautious about it as the following:
It has limited evidence of a carcinogenic effect. So people should not breathe dust and avoid contact with skin and eyes. If you want to contact this product, you must wear suitable protective clothing.
People can use the following data to convert to the molecule structure.
1. SMILES:O=S(=O)(c1ccc(N)cc1)N
2. InChI:InChI=1/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
3. InChIKey:FDDDEECHVMSUSB-UHFFFAOYAI
The following are the toxicity data of Sulfanilamide:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | 2gm/kg (2000mg/kg) | Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 1079, 1966. | |
guinea pig | LD50 | oral | 3130mg/kg (3130mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 82, Pg. 86, 1944. | |
mouse | LD50 | intraperitoneal | 5mg/kg (5mg/kg) | Antibiotics Annual. Vol. 5, Pg. 886, 1957/1958. | |
mouse | LD50 | intravenous | 500mg/kg (500mg/kg) | Antibiotics Annual. Vol. 5, Pg. 972, 1957/1958. | |
mouse | LD50 | oral | 3gm/kg (3000mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 48, Pg. 336, 1952. | |
mouse | LD50 | subcutaneous | 2900mg/kg (2900mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955. | |
rabbit | LD50 | oral | 1300mg/kg (1300mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 31(3), Pg. 11, 1966. | |
rat | LD50 | intravenous | 1400mg/kg (1400mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 211, Pg. 367, 1950. | |
rat | LD50 | oral | 3900mg/kg (3900mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1072, 1986. |
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