| Identification | More | [Name]
4-Hydrazinobenzene-1-sulfonamide hydrochloride | [CAS]
17852-52-7 | [Synonyms]
BENZENESULFONAMIDE
BENZENESULFONYLAMIDE
BENZENESULPHONAMIDE
4-HYDRAZINOBENZENE-1-SULFONAMIDE HCL
p-Sulfonamidophenylhydrazine HCl
4-Aminosulfonylphenylhydrazine hydrochloride
4-Hydrazinobenzene-1-sulfonamide hydrochloride
4-Sulfonamidophenylhydrazine hydrochloride
4-SPH | [EINECS(EC#)]
202-637-1 | [Molecular Formula]
C6H10ClN3O2S | [MDL Number]
MFCD00007930 | [Molecular Weight]
223.68 | [MOL File]
17852-52-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
149-152 °C(lit.)
| [density ]
1.644[at 20℃] | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Methanol (Slightly, Heated), Water (Slightly) | [form ]
powder to crystal | [color ]
White to Light yellow to Light orange | [Water Solubility ]
Soluble in water. | [Sensitive ]
Hygroscopic | [InChI]
InChI=1S/C6H9N3O2S.ClH/c7-9-5-1-3-6(4-2-5)12(8,10)11;/h1-4,9H,7H2,(H2,8,10,11);1H | [InChIKey]
IKEURONJLPUALY-UHFFFAOYSA-N | [SMILES]
C1(S(=O)(=O)N)C=CC(NN)=CC=1.Cl | [LogP]
-0.99 at 20℃ | [CAS DataBase Reference]
17852-52-7(CAS DataBase Reference) | [EPA Substance Registry System]
Benzenesulfonamide, 4-hydrazinyl-, hydrochloride (1:1) (17852-52-7) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
DA9380000
| [Hazard Note ]
Irritant | [HS Code ]
29350090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
Intermediate in the production of Celebrex. | [Flammability and Explosibility]
Nonflammable | [Synthesis]
The general procedure for the synthesis of p-hydrazinylbenzenesulfonamide hydrochloride from crystalline sulfanilamide was as follows: firstly, 4'-methylacetophenone was reacted with succinic anhydride in the presence of diisopropanolamine (LDA) and tetrahydrofuran (THF) for 1 hr at -78 °C to afford p-tolyl-4,6-dioxohexanoic acid in 66% yield and the product was a white solid. Subsequently, the sulfonamide was reacted with sodium nitrite (NaNO2) and concentrated hydrochloric acid for 30 min at 0-4 °C, followed by the addition of tin(II) chloride (SnCl2), and the reaction was continued for 4 h at 0 °C to produce 4-sulfonylaminophenylhydrazine hydrochloride in 55% yield, the product being a pale yellow solid. Finally, p-tolyl-4,6-dioxohexanoic acid was reacted with 4-sulfonylaminophenylhydrazine hydrochloride in a methanolic solution of triethanolamine (TEA) at room temperature for 16 h to give compound 30c, 3-[1-{p-(p-(sulfonylamino)phenyl}-5-p-tolyl-1H-pyrazol-3-yl]propanoic acid in 76% yield and the product was a yellow solid. | [References]
[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 18, p. 4444 - 4452
[2] Organic Letters, 2012, vol. 14, # 19, p. 5030 - 5033,4
[3] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 4, p. 913 - 922
[4] Patent: US2007/292352, 2007, A1. Location in patent: Page/Page column 45-46
[5] Patent: US2003/236294, 2003, A1. Location in patent: Page 9 |
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