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Mafenide hydrochloride
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Name

Mafenide hydrochloride

 EINECS 205-325-3
CAS No. 138-37-4 Density N/A
PSA 94.56000 LogP 3.07610
Solubility N/A Melting Point 261-263 °C(lit.)
Formula C7H10N2O2S.HCl Boiling Point 382 °C at 760 mmHg
Molecular Weight 222.696 Flash Point 184.8 °C
Transport Information N/A Appearance N/A
Safety 22-36/37-45 Risk Codes 42/43
Molecular Structure Molecular Structure of 138-37-4 (Mafenide hydrochloride) Hazard Symbols HarmfulXn
Synonyms

Benzenesulfonamide,4-(aminomethyl)-, monohydrochloride (9CI);p-Toluenesulfonamide, a-amino-, hydrochloride (6CI);p-Toluenesulfonamide, a-amino-, monohydrochloride (8CI);4-(Aminomethyl)benzene sulfonamidemonohydrochloride;4-Aminosulfonylbenzylamine hydrochloride;4-Homosulfanilamide hydrochloride;Homosulfamine;Homosulfamine hydrochloride;Homosulfanilamide hydrochloride;Marfanil;Sulfamylonhydrochloride;p-(Aminomethyl)benzenesulfonamide hydrochloride;p-(Aminomethyl)benzenesulfonamide monohydrochloride;p-Aminomethylphenylsulfonamide hydrochloride;a-Amino-p-toluenesulfonamide hydrochloride;

 

Mafenide hydrochloride Synthetic route

1226869-60-8

tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate

138-37-4

mafenide hydrochloride

1228647-88-8

tert-butyl 2,2′-(2,2′-(4-sulfamoylbenzylazanediyl)bis(methylene)-bis(1H-imidazole-2,1-diyl))diacetate

Conditions
ConditionsYield
Stage #1: tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate; mafenide hydrochloride With acetic acid In 1,2-dichloro-ethane at 75℃; for 0.5h; Inert atmosphere;
Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 0 - 20℃; Inert atmosphere;		99%
138-37-4

mafenide hydrochloride

sodium 3,5-bis(bis((ethoxycarbonyl)methyl)aminomethyl)benzoate

662165-89-1

{[3-[(bis-ethoxycarbonylmethyl-amino)-methyl]-5-(4-sulfamoyl-benzylcarbamoyl)-benzyl]-ethoxycarbonylmethyl-amino}-acetic acid ethyl ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In chloroform; N,N-dimethyl-formamide at 20℃; for 12h;98%
1036738-13-2

2,6-dichloropyrido[3,2-d]pyrimidin-4-ol

138-37-4

mafenide hydrochloride

1036738-14-3

4-[(6-chloro-4-hydroxy-pyrido[3,2-d]pyrimidin-2-ylamino)-methyl]-benzenesulfonamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 110 - 120℃; for 3h;97%
35444-44-1

methyl adipoyl chloride

138-37-4

mafenide hydrochloride

928211-28-3

5-(4-Sulfamoyl-benzylcarbamoyl)-pentanoic acid methyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 7h;95%
463-71-8

thiophosgene

138-37-4

mafenide hydrochloride

51929-73-8

4-(isothiocyanatomethyl)benzenesulfonamide

Conditions
ConditionsYield
With concentrated hydrochloric acid In water95%
173459-80-8

benzyl [2‑(1H‑benzo[d][1,2,3]triazol‑1‑yl)‑2‑oxoethyl]carbamate

138-37-4

mafenide hydrochloride

benzyl (2-oxo-2-((4-sulfamoylbenzyl)amino)ethyl)carbamate

Conditions
ConditionsYield
In tetrahydrofuran at 70℃; for 0.5h; Microwave irradiation;95%

C21H23N5O4S

138-37-4

mafenide hydrochloride

benzyl (S)-(4-(methylthio)-1-oxo-1-((2-oxo-2-((4-sulfamoylbenzyl)amino)ethyl)amino)butan-2-yl)carbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 70℃; for 0.5h; Microwave irradiation;95%

tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate

138-37-4

mafenide hydrochloride

tert-butyl (R)-(1-oxo-3-phenyl-1-((4-sulphamoylbenzyl)amino)propan-2-yl)carbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 70℃; for 0.5h; Microwave irradiation;95%
138-37-4

mafenide hydrochloride

6806-56-0, 13639-50-4, 51898-27-2, 62860-10-0, 63783-77-7, 92217-67-9, 92217-68-0, 130796-15-5

O2,O3,O4,O6,S-Pentaacetyl-1-thio-β-D-glucopyranose

1219708-35-6

C21H28N2O11S2

Conditions
ConditionsYield
Stage #1: O2,O3,O4,O6,S-Pentaacetyl-1-thio-β-D-glucopyranose With Diethyl 2-bromomalonate In methanol at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: mafenide hydrochloride With N-ethyl-N,N-diisopropylamine In methanol at 20℃; Inert atmosphere;		94%
632-79-1

Tetrabromophthalic anhydride

138-37-4

mafenide hydrochloride

4-((4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)methyl)benzenesulfonamide hydrochloride

Conditions
ConditionsYield
With acetic acid at 130℃; for 1.5h; Inert atmosphere;94%

Mafenide hydrochloride Chemical Properties


IUPAC Name: 4-(Aminomethyl)benzenesulfonamide hydrochloride
Canonical SMILES: C1=CC(=CC=C1CN)S(=O)(=O)N.Cl
InChI: InChI=1S/C7H10N2O2S.ClH/c8-5-6-1-3-7(4-2-6)12(9,10)11;/h1-4H,5,8H2,(H2,9,10,11);1H
InChIKey: SIACJRVYIPXFKS-UHFFFAOYSA-N
Molecular Weight: 222.69244 [g/mol]
Molecular Formula: C7H11ClN2O2S
H-Bond Donor: 3
H-Bond Acceptor: 4
Rotatable Bond Count: 2
Exact Mass: 222.022976
MonoIsotopic Mass: 222.022976
Topological Polar Surface Area: 86.2
Heavy Atom Count: 13
Complexity: 224
EINECS: 205-325-3 
Flash Point: 184.8 °C
Enthalpy of Vaporization: 63.04 kJ/mol
Boiling Point: 382 °C at 760 mmHg
Vapour Pressure: 4.86E-06 mmHg at 25 °C
Melting Point of Mafenide hydrochloride (CAS NO.138-37-4): 261-263 °C(lit.)

Mafenide hydrochloride Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 900mg/kg (900mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Life Sciences. Vol. 5, Pg. 2279, 1966.
mouse LD50 oral 8gm/kg (8000mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 49, Pg. 11, 1953.
mouse LD50 subcutaneous 3500mg/kg (3500mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 49, Pg. 11, 1953.
mouse LDLo intramuscular 3500mg/kg (3500mg/kg)   Lancet. Vol. 2, Pg. 523, 1944.
mouse LDLo intraperitoneal 2500mg/kg (2500mg/kg)   Lancet. Vol. 2, Pg. 523, 1944.
rat LD50 intravenous 1170mg/kg (1170mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Life Sciences. Vol. 5, Pg. 2279, 1966.

Mafenide hydrochloride Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 42/43 
R42/43:May cause sensitization by inhalation and skin contact.
Safety Statements: 22-36/37-45 
S22:Do not breathe dust. 
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 2
RTECS of Mafenide hydrochloride (CAS NO.138-37-4): XT5425000

Mafenide hydrochloride Specification

 Mafenide hydrochloride (CAS NO.138-37-4), its Synonyms are 4-Aminomethylbenzenesulfonamide hydrochloride ; 4-Homosulfanilamide hydrochloride ; Ambamide hydrochloride ; Emilene hydrochloride ; Homosulfamine ; Homosulfamine hydrochloride ; Homosulfanilamide hydrochloride ; Mafenide HCl ; Neofamid hydrochloride ; Sulfamylon hydrochloride ; Sulfbenzamine hydrochloride ; alpha-Amino-p-toluenesulfonamide hydrochloride ; p-(Aminomethyl)benzenesulfonamide hydrochloride ; p-(Aminomethyl)benzenesulfonamide monohydrochloride ; p-Aminomethylphenylsulfonamide hydrochloride ; p-Toluenesulfonamide, alpha-amino-, hydrochloride .

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