4-アセトアミドベンゼンスルホニルクロリド
4-アセトアミドベンゼンスルホニルクロリド · p-アセチルアミノベンゼンスルホニルクロリド · 4-アセチルアミノベンゼンスルホン酸クロリド · N-アセチルスルファニリルクロリド · 4-(アセチルアミノ)ベンゼンスルホニルクロリド · 4-(アセチルアミノ)ベンゼンスルホン酸クロリド · 4‐（アセチルアミノ）ベンゼンスルホン酸クロリド · 4-アセトアミドフェニルスルホニルクロリド
識別子と物理属性
| CAS No. | 121-60-8 |
|---|---|
| 分子式 | C8H8ClNO3S |
| 平均分子量 | 233.67 g/mol |
| 単同位体質量 | 232.9913418 g/mol |
| SMILES | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1 |
| InChIKey | GRDXCFKBQWDAJH-UHFFFAOYSA-N |
| PubChem CID | 8481 |
| ChEMBL | CHEMBL3185390 |
| EC No. | 204-485-1 |
| DTXSID | DTXSID8026981 |
| 現地名 | 4-アセトアミドベンゼンスルホニルクロリド |
化学・物理的性質
| XLogP | 1.4 |
|---|---|
| 極性表面積 | 71.6 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 2 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 301 |
| 物質分類 | Nitrogen Compounds -> Aminobenzenesulfonic Acids |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 臭い | SLIGHT ODOR OF ACETIC ACID |
| Color/Form | NEEDLES FROM BENZENEPRISMS FROM BENZENE-CHLOROFORMTHICK, LIGHT TAN PRISMS FROM BENZENELIGHT TAN TO BROWNISH POWDER OR FINE CRYSTALS |
| 溶解度 | VERY SOL IN ETHER, ALCOHOLSOL IN HOT CHLOROFORMSOLUBLE IN HOT BENZENEAcetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)わずかに溶ける |
| 融点 | 149 °C142-145 °C (dec.)(lit.) |
| Physical Description | Dry PowderLight tan solid[Merck Index] Off-white powder[MSDSonline] |
| Other Experimental Properties | DECOMP IN WATER |
| 沸点 | 426.8±28.0 °C(Predicted) |
| 密度 | 1.2977 (rough estimate) |
| 蒸気圧 | 0Pa at 25℃ |
| 屈折率 | 1.6300 (estimate) |
| 貯蔵条件 | Sealed in dry,2-8°C |
| pKa（酸解離定数） | 13.75±0.70(Predicted) |
| 外観・状態 | 粒状の結晶性粉末または結晶 |
| 色 | ホワイトからクリームベージュ |
| Merck | 14,103 |
| BRN | 746676 |
| InChI | 1S/C8H8ClNO3S/c1-6(11)10-7-2-4-8(5-3-7)14(9,12)13/h2-5H,1H3,(H,10,11) |
| InChIKey | GRDXCFKBQWDAJH-UHFFFAOYSA-N |
| SMILES | CC(=O)Nc1ccc(cc1)S(Cl)(=O)=O |
| LogP（分配係数） | 2.05 at 25℃ |
| CAS データベース | 121-60-8(CAS DataBase Reference) |
| NISTの化学物質情報 | P-acetamidobenzene sulfonyl chloride(121-60-8) |
| EPAの化学物質情報 | Benzenesulfonyl chloride, 4-(acetylamino)- (121-60-8) |
化学的特性
OFF-WHITE TO SLIGHTLY GREY GRANULAR CRYST. POWDER
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 0.5% (1 of 207) of reports.DangerH314 (47.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P261, P264, P271, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 207 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Benzenesulfonyl chloride, 4-(acetylamino)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonyl chloride, 4-(acetylamino)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 30-06-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/56984-Acetamidobenzenesulphonyl chloride: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | A skin, eye, and mucous membrane irritant[Merck Index] Causes weakness and ataxia in lethal dose studies[RTECS] Reacts with waterA corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitisExposure may cause convulsions[MSDSonline] |
| Hazard Classes and Categories | Skin Corr. 1B (47.8%) |
| Skin, Eye, and Respiratory Irritations | IRRITANT TO SKIN, EYES, & MUCOUS MEMBRANES OF NOSE & THROAT. |
| 有害作用 | Neurotoxin - Other CNS neurotoxin |
| Human Toxicity Excerpts | IRRITANT TO SKIN, EYES, AND MUCOUS MEMBRANES OF NOSE AND THROAT. |
| F | 9-21 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | DB8837500 |
| 輸送番号（UN） | UN 3261 8/PG 2 |
| 毒性 | LD50 oral in rat: > 3200mg/kg |
| 税関コード | 29242995 |
| 危険文句（R） | 22-34-37 |
| 化審法 | (3)-1988 |
| 危険表示 | C |
| 安全措置（S） | 26-36/37/39-45-28B |
| 危険等級 | 8Skin Corr. 1BSTOT SE 3 |
| 包装等級 | II |
| 貯蔵分類 | 8A - Combustible corrosive hazardous materials |
| 有害物質データ | 121-60-8(Hazardous Substances Data) |
用途
使用
N-Acetylsulfanilyl chloride is usedin the preparation of sulfanilamide and its derivatives which are intermediates to produce sulfa drugs. They are used in the prevention and treatment of bacterial infections, diabetes mellitus, edema, hypertension, and gout. It is also used as a Pharma raw material. N-Acetylsulfanilyl chloride widely used in the fields of dye, medicine, mainly used for preparation of Sulfanilamide, Sulfanilylureal, Sulfatolamide, Sulphathiourea , Sulfaguanidine and Sulfacetamide and etc.
一般的な説明
L-hydroxyproline has been derivatized with N-acetylsulfanilyl chloride and 5-chlorovaleric acid during the synthesis of the haptens HP1 and HP2.
製法・合成法
調製方法
Acetanilide is introduced into stirred chlorosulfuric acid solution at 20 ℃. The solution is then heated to 55 ℃ and kept at this temperature for 1.5 h. The solution is cooled to 20 ℃ and introduced as a thin jet into water, the temperature of which is kept at 0 – 5 ℃ by external cooling. The precipitated sulfochloride is filtered and washed with cold water until neutral to Congo Red. Yield is 80 – 82%. The crude product contains about 60% water; the dried product melts at 144 – 147 ℃. About 1 – 2% of bis(acetylaminophenyl) sulfone is obtained as a byproduct. If thionyl chloride is added, less chlorosulfuric acid is needed because it can be replaced partly byoleum. The product is stable for several days if kept in a cool place. It is generally used directly in the moist state. 4-(Acetylamino)benzenesulfonyl chloride is an important intermediate in the manufacture of sulfonamides and in the synthesis of parabase ester.
純化方法
Crystallise the chloride from toluene, CHCl3, or ethylene dichloride. [Beilstein 14 IV 2703.]