Product Name

  • Name

    Sulfanilamide

  • EINECS 200-563-4
  • CAS No. 63-74-1
  • Article Data103
  • CAS DataBase
  • Density 1.427 g/cm3
  • Solubility 7.5 g/L at 25 °C
  • Melting Point 164-167 °C
  • Formula C6H8N2O2S
  • Boiling Point 400.5 °C at 760 mmHg
  • Molecular Weight 172.208
  • Flash Point 196 °C
  • Transport Information
  • Appearance White to almost white crystalline powder
  • Safety 24/25-36-22
  • Risk Codes 40
  • Molecular Structure Molecular Structure of 63-74-1 (Sulfanilamide)
  • Hazard Symbols HarmfulXn
  • Synonyms Sulfanilamide (SN);Sulfanilamide(8CI);(4-(Aminosulfonyl)phenyl)amine;4-(Aminosulfonyl)aniline;4-Aminobenzenesulfonamide;4-Aminophenylsulfonamide;A-349;Albosal;Ambeside;Antistrept;Astreptine;Bactesid;Deseptyl;Dipron;Ergaseptine;Erysipan;Fourneau 1162;Gombardol;Infepan;NSC 7618;Neococcyl;Orgaseptine;PABS;Prontosil white;PronzinAlbum;Proseptine;Proseptol;Pysococcine;Ro 1-3354;Rubiazol A;Sanamid;Septamide Album;Septanilam;Septinal;Septoplex;Septoplix;Stramid;Strepamide;Strepsan;Streptasol;Streptocid;Streptocid album;Streptocide (white);Streptoclase;Strepton;Streptopan;Streptosil;Sulfamidyl;Sulfana;Sulfanalone;Sulfanidyl;Sulfanil;Sulfanilamide Vaginal Cream;Sulfonamide;Sulfonylamide;Sulphanilamide;Tolder;Whitestreptocide;p-Aminophenylsulfonamide;p-Anilinesulfonamide;p-Sulfamoylaniline;Sulfanilamide;
  • PSA 94.56000
  • LogP 2.27850

Synthetic route

p-nitrobenzenesulfonamide
6325-93-5

p-nitrobenzenesulfonamide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
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
36326-86-0

4-azidobenzenesulfonamide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
With D-glucose; potassium hydroxide In water at 85℃; for 0.0833333h; Green chemistry; chemoselective reaction;99%
(p-aminobenzene)sulfonyl azide
14860-69-6

(p-aminobenzene)sulfonyl azide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
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;
chlorobenzene
108-90-7

chlorobenzene

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
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
57-67-0

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

A

bis(4-aminophenyl)disulfide
722-27-0

bis(4-aminophenyl)disulfide

B

sulfanilamide
63-74-1

sulfanilamide

C

aniline
62-53-3

aniline

D

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
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
352542-64-4

tert-butyl (4-sulfamoylphenyl)carbamate

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
With H-β zeolite In dichloromethane for 10h; Heating;91%
Acetanilid
103-84-4

Acetanilid

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
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
benzenesulfonamide
98-10-2

benzenesulfonamide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
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
2858-20-0

5-chloro-2,6-dimethyl-pyrimidin-4-ylamine

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

A

N-[4-(dimethylamino-4-ylsulfonyl)phenyl]acetamide
54951-54-1

N-[4-(dimethylamino-4-ylsulfonyl)phenyl]acetamide

B

sulfanilamide
63-74-1

sulfanilamide

C

Sulfaclomid
4015-18-3

Sulfaclomid

D

C22H22ClN5O6S2
84729-42-0

C22H22ClN5O6S2

E

4-(4'-Acetylaminobenzensulfonyl)amino-5-chlor-2,6-dimethylpyrimidin
4049-04-1

4-(4'-Acetylaminobenzensulfonyl)amino-5-chlor-2,6-dimethylpyrimidin

Conditions
ConditionsYield
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
p-acetylaminobenzenesulfonamide
121-61-9

p-acetylaminobenzenesulfonamide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol for 1h; Reflux;68%
With hydrogenchloride
With sodium hydroxide
4-acetamidobenzenesulfonyl azide
2158-14-7

4-acetamidobenzenesulfonyl azide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
With hydrogenchloride In water at 5℃; for 0.583333h; Reflux;60%
sulphapyridine
144-83-2

sulphapyridine

A

2-aminopyridine
504-29-0

2-aminopyridine

B

bis(4-aminophenyl)disulfide
722-27-0

bis(4-aminophenyl)disulfide

C

p-nitrobenzenesulfonamide
6325-93-5

p-nitrobenzenesulfonamide

D

sulfanilamide
63-74-1

sulfanilamide

E

aniline
62-53-3

aniline

F

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
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%
4-Chlorobenzenesulfonamide
98-64-6

4-Chlorobenzenesulfonamide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
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
34894-11-6

N-formyl-sulfanilyl chloride

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
With ammonium hydroxide
Multi-step reaction with 2 steps
1: aqueous ammonia
2: aq. NaOH solution
View Scheme
4,4'-(carbonylbis(azanediyl))dibenzenesulfonamide
1773-43-9

4,4'-(carbonylbis(azanediyl))dibenzenesulfonamide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
With sulfuric acid at 150℃;
With sodium hydroxide at 100℃;
N-formyl-sulfanilic acid amide
829-72-1

N-formyl-sulfanilic acid amide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
With water
With ammonium hydroxide
With sulfuric acid
With sodium hydroxide
Multi-step reaction with 2 steps
2: ethanolic NaOH-solution
View Scheme
N-formyl-sulfanilic acid acetylamide
781-00-0

N-formyl-sulfanilic acid acetylamide

A

sulfanilamide
63-74-1

sulfanilamide

B

sulphaacetamide
144-80-9

sulphaacetamide

Conditions
ConditionsYield
With sodium hydroxide
4-amidobenzylsulfonamide
6306-24-7

4-amidobenzylsulfonamide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
With alkaline aqueous sodium hypochlorite
(E)-4-(phenyldiazenyl)benzenesulfonamide
102840-86-8

(E)-4-(phenyldiazenyl)benzenesulfonamide

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
With hydrogenchloride; tin
(E)-4-(phenyldiazenyl)benzenesulfonamide
102840-86-8

(E)-4-(phenyldiazenyl)benzenesulfonamide

A

4-(N'-phenyl-hydrazino)-benzenesulfonic acid amide
521972-91-8

4-(N'-phenyl-hydrazino)-benzenesulfonic acid amide

B

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
With sodium hydroxide; sodium dithionite
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

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

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

sulfanilamide
63-74-1

sulfanilamide

hidrazobenzene-4,4'-disulfonamide
4392-55-6

hidrazobenzene-4,4'-disulfonamide

A

sulfanilamide
63-74-1

sulfanilamide

B

C6H7N2O2S(1-)

C6H7N2O2S(1-)

Conditions
ConditionsYield
With Britton-Robinson buffer Rate constant; controlled potential electrolysis;
p-<(8-hydroxy-5-quinolyl)azo>benzenesulphonamide
16588-39-9

p-<(8-hydroxy-5-quinolyl)azo>benzenesulphonamide

A

5-amino-8-hydroxyquinoline
13207-66-4

5-amino-8-hydroxyquinoline

B

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide for 1.5h; electrolysis at dropping mercury electrode;
4-(2,4-dihydroxy-phenylazo)-benzenesulfonic acid amide
140648-35-7

4-(2,4-dihydroxy-phenylazo)-benzenesulfonic acid amide

A

4-aminoresorcinol
13066-95-0

4-aminoresorcinol

B

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
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
140648-38-0

4-(5-bromo-2-hydroxy-phenylazo)-benzenesulfonic acid amide

A

2-amino-4-bromo-phenol
40925-68-6

2-amino-4-bromo-phenol

B

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
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
140648-40-4

4-(5-Formyl-2-hydroxy-phenylazo)-benzenesulfonamide

A

sulfanilamide
63-74-1

sulfanilamide

B

3-amino-4-hydroxybenzaldehyde
163036-58-6

3-amino-4-hydroxybenzaldehyde

Conditions
ConditionsYield
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
140648-36-8

4-(2-Hydroxy-5-methoxy-phenylazo)-benzenesulfonamide

A

2-amino-4-methoxyphenol
20734-76-3

2-amino-4-methoxyphenol

B

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
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
140648-37-9

4-(4-Dimethylamino-2-hydroxy-phenylazo)-benzenesulfonamide

A

2-amino-5-(dimethylamino)phenol
15103-39-6

2-amino-5-(dimethylamino)phenol

B

sulfanilamide
63-74-1

sulfanilamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide Rate constant; Thermodynamic data; electrochemical reduction (HMDE electrode), various pHs (from 2.03 to 10.00);
acetic anhydride
108-24-7

acetic anhydride

sulfanilamide
63-74-1

sulfanilamide

p-acetylaminobenzenesulfonamide
121-61-9

p-acetylaminobenzenesulfonamide

Conditions
ConditionsYield
at 20℃; for 1h;100%
In ethanol at 20 - 70℃; for 0.0166667h; other time tested;
sulfanilamide
63-74-1

sulfanilamide

4-azidobenzenesulfonamide
36326-86-0

4-azidobenzenesulfonamide

Conditions
ConditionsYield
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
500-22-1

3-pyridinecarboxaldehyde

sulfanilamide
63-74-1

sulfanilamide

N4-(3-pyridylidene) sulfanilamide
74028-05-0

N4-(3-pyridylidene) sulfanilamide

Conditions
ConditionsYield
at 150 - 155℃; for 0.0833333h;100%
In ethanol for 3h; Heating;
trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

sulfanilamide
63-74-1

sulfanilamide

4-(Trifluoromethyl-azo)-benzenesulfonamide

4-(Trifluoromethyl-azo)-benzenesulfonamide

Conditions
ConditionsYield
In methanol at 20℃; for 24h;100%
sulfanilamide
63-74-1

sulfanilamide

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

2,2,2-trifluoro-N-(4-sulfamoylphenyl)acetamide

2,2,2-trifluoro-N-(4-sulfamoylphenyl)acetamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 0.5h;100%
In 1,4-dioxane100%
In 1,4-dioxane97%
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

sulfanilamide
63-74-1

sulfanilamide

4-Amino-N-dimethylaminomethylenebenzenesulfonamide

4-Amino-N-dimethylaminomethylenebenzenesulfonamide

Conditions
ConditionsYield
In dichloromethane for 0.5h; Heating;100%
methyl 2-chloroquinazoline-7-carboxylate
953039-79-7

methyl 2-chloroquinazoline-7-carboxylate

sulfanilamide
63-74-1

sulfanilamide

methyl 2-(4-sulfamoyl-phenylamino)quinazoline-7-carboxylate

methyl 2-(4-sulfamoyl-phenylamino)quinazoline-7-carboxylate

Conditions
ConditionsYield
In isopropyl alcohol at 90℃; for 2h;100%
methyl 2-chloroquinazolin-6-carboxylate
1036755-96-0

methyl 2-chloroquinazolin-6-carboxylate

sulfanilamide
63-74-1

sulfanilamide

Methyl 2-(4-sulfamoylphenylamino)quinazolin-6-carboxylate
1036743-15-3

Methyl 2-(4-sulfamoylphenylamino)quinazolin-6-carboxylate

Conditions
ConditionsYield
at 90℃; for 2h;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

sulfanilamide
63-74-1

sulfanilamide

tert-butyl (4-sulfamoylphenyl)carbamate
352542-64-4

tert-butyl (4-sulfamoylphenyl)carbamate

Conditions
ConditionsYield
In 1,4-dioxane Reflux;100%
With potassium hydroxide In tetrahydrofuran; water
4-nitrosobenzoic acid ethyl ester
7476-79-1

4-nitrosobenzoic acid ethyl ester

sulfanilamide
63-74-1

sulfanilamide

(E)-ethyl 4-((4-sulfamoylphenyl)diazenyl)benzoate

(E)-ethyl 4-((4-sulfamoylphenyl)diazenyl)benzoate

Conditions
ConditionsYield
With acetic acid In dichloromethane100%
m-phenylenediamine
108-45-2

m-phenylenediamine

sulfanilamide
63-74-1

sulfanilamide

(E)-4-(2-(4-sulfonamido)diazenyl)benzene-1,3-diamine
103-12-8

(E)-4-(2-(4-sulfonamido)diazenyl)benzene-1,3-diamine

Conditions
ConditionsYield
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%
3,6-dichlorpyridazine
141-30-0

3,6-dichlorpyridazine

sulfanilamide
63-74-1

sulfanilamide

sulfachloropyridazine sodium

sulfachloropyridazine sodium

Conditions
ConditionsYield
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
110-13-4

2,5-hexanedione

sulfanilamide
63-74-1

sulfanilamide

4-(2,5-dimethyl-1H-pyrrol-1-yl)benzenesulfonamide
26165-69-5

4-(2,5-dimethyl-1H-pyrrol-1-yl)benzenesulfonamide

Conditions
ConditionsYield
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
sulfanilamide
63-74-1

sulfanilamide

phenylacetyl chloride
103-80-0

phenylacetyl chloride

N-[4-(aminosulfonyl)phenyl]-2-phenylacetamide

N-[4-(aminosulfonyl)phenyl]-2-phenylacetamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 15h;99%
With triethylamine In acetonitrile at 0 - 5℃;35%
With pyridine
N,N'-bis(triethylgermyl)sulfanilamide

N,N'-bis(triethylgermyl)sulfanilamide

sulfanilamide
63-74-1

sulfanilamide

N-triethylgermylsulfanilamide
566174-01-4

N-triethylgermylsulfanilamide

Conditions
ConditionsYield
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%
3-(triethoxypropyl) isocyanate
24801-88-5

3-(triethoxypropyl) isocyanate

sulfanilamide
63-74-1

sulfanilamide

C26H50N4O10SSi2
1311165-68-0

C26H50N4O10SSi2

Conditions
ConditionsYield
In acetonitrile for 24h; Inert atmosphere; Reflux;99%
benzaldehyde
100-52-7

benzaldehyde

sulfanilamide
63-74-1

sulfanilamide

benzylsulfamide
104-22-3

benzylsulfamide

Conditions
ConditionsYield
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
63-74-1

sulfanilamide

2-chloro-4-(p-hydroxyphenyl)pyrimidine

2-chloro-4-(p-hydroxyphenyl)pyrimidine

4-{[4-(4-hydroxyphenyl)pyrimidin-2-yl]amino}benzenesulfonamide
882875-01-6

4-{[4-(4-hydroxyphenyl)pyrimidin-2-yl]amino}benzenesulfonamide

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 160℃; for 2h; Microwave irradiation;99%
With hydrogenchloride In ethanol Microwave irradiation;99%
5-amino-4,6-dichloropyridimine
5413-85-4

5-amino-4,6-dichloropyridimine

sulfanilamide
63-74-1

sulfanilamide

4-((5-amino-6-chloropyrimidin-4-yl)amino)benzenesulfonamide

4-((5-amino-6-chloropyrimidin-4-yl)amino)benzenesulfonamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane; water Reflux;99%
potassium thioacyanate
333-20-0

potassium thioacyanate

sulfanilamide
63-74-1

sulfanilamide

3-chloropentane-2,4-dione
1694-29-7

3-chloropentane-2,4-dione

5-Acetyl-4-methyl-2-<(p-sulphamylphenyl)amino>thiazole
88323-93-7

5-Acetyl-4-methyl-2-<(p-sulphamylphenyl)amino>thiazole

Conditions
ConditionsYield
With silica sulfuric acid In neat (no solvent) at 20℃; for 0.416667h; Milling; Green chemistry;99%
salicylaldehyde
90-02-8

salicylaldehyde

sulfanilamide
63-74-1

sulfanilamide

4-[(2-hydroxybenzylidene)amino]benzenesulfonamide
2067-06-3

4-[(2-hydroxybenzylidene)amino]benzenesulfonamide

Conditions
ConditionsYield
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
117-80-6

2,3-Dichloro-1,4-naphthoquinone

sulfanilamide
63-74-1

sulfanilamide

4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide
6949-34-4

4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)benzenesulfonamide

Conditions
ConditionsYield
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
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

sulfanilamide
63-74-1

sulfanilamide

4-amino-N-[(dimethylamino)methylidene]benzenesulfonamide
6912-49-8

4-amino-N-[(dimethylamino)methylidene]benzenesulfonamide

Conditions
ConditionsYield
In neat (no solvent) at 20℃; under 760.051 Torr; for 0.25h; Green chemistry; chemoselective reaction;98%
sulfanilamide
63-74-1

sulfanilamide

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-chloro-N-(4-sulfamoylphenyl)acetamide
14949-01-0

2-chloro-N-(4-sulfamoylphenyl)acetamide

Conditions
ConditionsYield
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
63-74-1

sulfanilamide

triphenylphosphine
603-35-0

triphenylphosphine

N-<(p-aminophenyl)sulfonyl>triphenylphospha-λ5-azene
95978-84-0

N-<(p-aminophenyl)sulfonyl>triphenylphospha-λ5-azene

Conditions
ConditionsYield
With diethylazodicarboxylate In tetrahydrofuran at 0 - 25℃; for 12h;98%
With diethylazodicarboxylate In tetrahydrofuran at 0℃;79%
sulfanilamide
63-74-1

sulfanilamide

3,4-diethoxy-3-cyclobuten-1,2-dione
5231-87-8

3,4-diethoxy-3-cyclobuten-1,2-dione

4-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-benzenesulfonamide

4-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-benzenesulfonamide

Conditions
ConditionsYield
In ethanol Substitution; Heating;98%
tetrachlorophthalic anhydride
117-08-8

tetrachlorophthalic anhydride

sulfanilamide
63-74-1

sulfanilamide

4-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)benzenesulfonamide
88062-88-8

4-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With acetic acid at 130℃; for 2h;98%
With acetic acid for 24h; Reflux;
sulfanilamide
63-74-1

sulfanilamide

4-(bromoacetyl)toluene
619-41-0

4-(bromoacetyl)toluene

4-((2-oxo-2-(p-tolyl)ethyl)amino)benzenesulfonamide
1595285-57-6

4-((2-oxo-2-(p-tolyl)ethyl)amino)benzenesulfonamide

Conditions
ConditionsYield
In methanol for 4h; Reflux;98%

Sulfanilamide Consensus Reports

SULFANILAMIDE's reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Sulfanilamide Specification

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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