설파닐아미드
술파닐아미드 · P-아미노벤젠술폰아마이드 · 설파닐아미드 · 설프아닐아마이드 · 술프아닐아마이드 · 술프아닐아미드 · P-아미노벤젠술폰아미드 · P-아미노페닐술폰아미드
식별자 및 물리적 특성
| CAS No. | 63-74-1 |
|---|---|
| 분자식 | C6H8N2O2S |
| 평균 분자량 | 172.21 g/mol |
| 단동위원소 질량 | 172.03064868 g/mol |
| SMILES | Nc1ccc(S(N)(=O)=O)cc1 |
| InChIKey | FDDDEECHVMSUSB-UHFFFAOYSA-N |
| PubChem CID | 5333 |
| ChEMBL | CHEMBL21 |
| ChEBI | CHEBI:45373 |
| EC No. | 200-563-4 |
| DTXSID | DTXSID4023622 |
| 현지명 | 설파닐아미드 |
화학 및 물리적 성질
| XLogP | -0.6 |
|---|---|
| 극성 표면적 | 94.6 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 211 |
| pH | NEUTRAL TO LITMUSPH OF 0.5% AQ SOLN: 5.8-6.15.8-6.1 (5g/l, H2O, 20℃) |
| LogP(분배 계수) | -0.62log Kow = -0.62-0.8 |
| LogS | -1.36 |
| 밀도 | 1.08 at 68 °F (NTP, 1992) - Denser than waterwill sink1.08 @ 25 °C1.08 @25 °C |
| Color/Form | LEAFLETS FROM AQ ALCOHOLCRYSTALS |
| 용해도 | 0.1 to 1.0 mg/mL at 72 °F (NTP, 1992)7500IN WATER: 7.5 G/L AT 25 °C & 477 G/L AT 100 °C1 G DISSOLVES IN ABOUT 37 ML OF ALC & ABOUT 5 ML ACETONEINSOL IN CHLOROFORM, ETHER, BENZENE & PETROLEUM ETHERSOL IN GLYCEROL, PROPYLENE GLYCOL, HYDROCHLORIC ACID, SOLN OF POTASSIUM AND SODIUM HYDROXIDESOL IN ETHANOL5.37g/L |
| 녹는점 | 329 to 331 °F (NTP, 1992)165.5165.5 °C164-166 °C(lit.) |
| 증기압 | 0.0000073 [mmHg]0.00001 hPa (70 °C) |
| Physical Description | Sulfanilamide is a white powder. pH of 0.5% aqueous solution: 5.8-6.1. (NTP, 1992)Solid[Merck Index] |
| Stability/Shelf Life | SENSITIVE TO LIGHT |
| Ionization Efficiency | Positive2.76Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Dissociation Constants | 10.6 (at 20 °C)pKa = 10.43, pKb = 11.63pKa = 10.58 |
| 끓는 점 | 400.5±47.0 °C(Predicted) |
| 굴절률 | 1.6490 (estimate) |
| 저장 조건 | 2-8°C |
| pKa(산도 계수) | pKa 10.65(H2O t = 25.0±0.5 I = 0.2) (Uncertain) |
| 물리적 상태 | 가루 |
| 색상 | 흰색에서 희미한 베이지색 |
| 냄새 | 냄새 없는 |
| 용해도 | 25&C에서 7.5g/L |
| Merck | 14,8925 |
| BRN | 511852 |
| 헨리 상수 | 6.6×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10) |
| InChIKey | FDDDEECHVMSUSB-UHFFFAOYSA-N |
| SMILES | Nc1ccc(cc1)S(N)(=O)=O |
| LogP(분배 계수) | -0.620 |
| NIST | Benzenesulfonamide, 4-amino-(63-74-1) |
| EPA | Sulfanilamide (63-74-1) |
화학적 성질
White granules or powder crystals, odorless. Taste slightly bitter. Slightly soluble in cold water, ethanol, methanol, ether and acetone, easily soluble in boiling water, glycerin, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene and petroleum ether.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 41.6% (121 of 291) of reports.WarningH315 (58.4%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (58.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (57%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 291 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 121 of 291 reports by companies.There are 12 notifications provided by 170 of 291 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 규제 정보 | Chemical: Benzenesulfonamide, 4-amino-Regulation (EC) No 1107/2009 (amended)Status: Active Update: 11-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24237Sulphanilamide: Does not have an individual approval but may be used under an appropriate group standard |
| 운송 라벨(DOT) | Corrosive |
| 화재 위험 | Flash point data for this chemical are not available but it is probably combustible. (NTP, 1992) |
| 건강 유해성 | SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes, nausea, vomiting, fever, diarrhea, jaundice, headache, crystalluria, acidosis, ataxia, convulsions, cyanosis, dizziness, dermatitis, paralysis and respiratory failure. It has been implicated in aplastic anemia.ACUTE/CHRONIC HAZARDS: This material may cause irritation of the skin on contact. (NTP, 1992) |
| 유해성 요약 | Photoallergic contact dermatitis reported |
용도
용도
현대에서는 항생제가 이 화합물을 대체하여 사용량이 줄어들었고 현재는 질의 칸디다증 치료에 사용된다. 궤장성 대장염 혹은 류마티즈성 관절염에도 사용된다.
개요
Sulfanilamide is an organic sulfur compound structurally similar to p-aminobenzoic acid (PABA) with antibacterial property. Sulfanilamide competes with PABA for the bacterial enzyme dihydropteroate synthase, thereby preventing the incorporation of PABA into dihydrofolic acid, the immediate precursor of folic acid. This leads to an inhibition of bacterial folic acid synthesis and de novo synthesis of purines and pyrimidines, ultimately resulting in cell growth arrest and cell death.
용도
Sulfanilamide is an antibacterial agent and antimicrobial agent of sulfonamide type (topical and vaginal).
일반 설명
White powder. pH of 0.5% aqueous solution: 5.8-6.1.
제조 및 합성 방법
제조 방법
Sulfonamide is synthesized from acetanilide by chlorosulfonation, amination, hydrolysis, and neutralization:Acetanilide is reacted with chlorosulfonic acid at 40～50℃, then cooled, slowly added to water for acid decomposition, precipitated at the same time, dried and filtered to obtain p-acetamidobenzenesulfonyl chloride, and then subjected to ammoniation, and the amination temperature is controlled at 40～ 45 ℃, and then hydrolyzed, acidified to obtain sulfonamide.