p-トルエンスルホニルクロリド
p-トルエンスルホニルクロリド · トシルクロリド · (4-メチルフェニルスルホニル)クロリド · 4-メチルフェニルクロロスルホン · 4-トルエンスルホン酸クロリド · 4-メチルベンゼンスルホン酸クロリド · 4-メチルベンゼンスルホニルクロリド · p-トルエンスルホン酸クロリド
識別子と物理属性
| CAS No. | 98-59-9 |
|---|---|
| 分子式 | C7H7ClO2S |
| 平均分子量 | 190.65 g/mol |
| 単同位体質量 | 189.98552814 g/mol |
| SMILES | Cc1ccc(S(=O)(=O)Cl)cc1 |
| InChIKey | YYROPELSRYBVMQ-UHFFFAOYSA-N |
| PubChem CID | 7397 |
| EC No. | 202-684-8 |
| DTXSID | DTXSID1052660 |
| 現地名 | p-トルエンスルホニルクロリド |
化学・物理的性質
| XLogP | 3 |
|---|---|
| 極性表面積 | 42.5 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 209 |
| 物質分類 | Toxic Gases & Vapors -> Acid Halides |
| SpringerMaterials Properties | Schoenflies notation |
| LogP（分配係数） | 3.49 |
| 密度 | 1.3 g/cm³1.33 @25 °C1,006 g/cm3 |
| Color/Form | CRYSTALSTRICLINIC CRYSTALS FROM ETHER OR PETROLEUM ETHER |
| 溶解度 | INSOL IN WATERFREELY SOL IN ALCOHOL, BENZENE, ETHERSolubility in water: reaction塩化メチレン: 0.2 g/mL、透明加水分解 |
| 引火点 | 128 °C c.c. |
| 沸点 | 146 °C @ 15 MM HG134 °C10 mm Hg(lit.) |
| 融点 | 69-71 °C65-69 °C(lit.) |
| 蒸気密度 | Relative vapor density (air = 1): 6.6 |
| 蒸気圧 | Vapor pressure, Pa at 25 °C: 0.161 [mm Hg] @88 °C1 mm Hg ( 88 °C) |
| Physical Description | P-toluene sulfonylchloride appears as a white to gray powdered solid with a distinctive odor. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption. Used to make other chemicals.A white to gray solid[CAMEO] Hygroscopic[eChemPortal: SIDSUNEP] White or light yellow crystalline solid[MSDSonline]COLOURLESS-TO-YELLOW HYGROSCOPIC CRYSTALS WITH PUNGENT ODOUR. |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 結晶性粉末 |
| 色 | 白い |
| Merck | 14,9534 |
| BRN | 607898 |
| ヘンリー定数 | 1.0×100 mol/(m3Pa) at 25℃, Zhang et al. (2010) |
| 安定性 | 安定。避けるべき物質には、強塩基、強酸化剤、および水が含まれます。湿気に敏感。 |
| InChI | 1S/C7H7ClO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3 |
| InChIKey | YYROPELSRYBVMQ-UHFFFAOYSA-N |
| SMILES | Cc1ccc(cc1)S(Cl)(=O)=O |
| CAS データベース | 98-59-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzenesulfonyl chloride, 4-methyl-(98-59-9) |
| EPAの化学物質情報 | p-Toluenesulfonyl chloride (98-59-9) |
化学的特性
White to yellow solid.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 5.7% (53 of 926) of reports.DangerH290 (20%): May be corrosive to metals [Warning Corrosive to Metals]P234, P260, P261, P264, P264+P265, P271, P272, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P332+P317, P333+P317, P362+P364, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 926 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Benzenesulfonyl chloride, 4-methyl-Status: Active Update: 12-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/132424-Toluenesulphonyl chloride: Does not have an individual approval but may be used under an appropriate group standard |
| 輸送ラベル（DOT） | Corrosive |
| 火災危険 | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 健康有害性 | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| 有害性の概要 | A skin, eye, and respiratory tract irritant[HSDB] Reacts violently with water evolving hydrochloric acidA corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitis[MSDSonline] Slowly hydrolyzes to strong acids (HCl and p-toluenesulfonic acid)Severely irritating to skin and eyes in animal testing[AIHA] Contact dermatitis documented in a chemist[Kanerva, p. 1841] |
| 反応性グループ | Acyl Halides, Sulfonyl Halides, and Chloroformates |
| UN 分類 | UN Hazard Class: 8UN Pack Group: II |
| Chemical Dangers | Decomposes on heating. This produces toxic and corrosive fumes including sulfur oxides and hydrogen chloride. Reacts with water and moist air. This produces hydrogen chloride (see ICSC 0163). |
| Packaging and Labelling | Unbreakable packaging. Put breakable packaging into closed unbreakable container. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Met. Corr. 1 (20%) |
| 消火 | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:Use dry powder, carbon dioxide. NO water. NO foam. |
| 応急処置措置 | Fresh air, rest.Remove contaminated clothes. Rinse skin with plenty of water or shower.Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention . |
| 応急処置 | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| 安全保管 | Dry. Well closed. Store in an area without drain or sewer access. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| 漏出処分 | Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into containers. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Eye Prevention | Wear safety goggles or eye protection in combination with breathing protection if powder. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered. |
| Skin Prevention | Protective gloves. |
| Exposure Prevention | PREVENT DISPERSION OF DUST! |
| 有害作用 | Dermatotoxin - Skin burns. |
| Signs and Symptoms | Cough.Redness. Pain.Sore throat. |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Human Toxicity Excerpts | ...PRODUCE SEVERE PRIMARY IRRITATION OF EYES, SKIN, OR RESP TRACT. DELAYED VESICATION IS NOT UNCOMMON. SENSITIZATION MAY ALSO OCCUR... /ACID HALIDES/STRONG IRRITANT & VESICANT. /FROM TABLE/WHILE CUMULATIVE TOXIC EFFECTS ARE THEORETICALLY POSSIBLE IF ORIGINAL ORG ACID IS ALSO KNOWN TO BE CUMULATIVE IN ACTION...IRRITANT PROPERTIES OF THE HALIDE PREVENT VOLUNTARY EXPOSURE TO SIGNIFICANT AMOUNTS... /ACID HALIDES/ |
| Non-Human Toxicity Excerpts | REMSEN FAHLBERG SACCHARIN & ITS CONTAMINANTS (O-TOLUENE SULFONAMIDE (OTS), P-TOLUENE SULFONAMIDE (PTS), O-SULFAMOYL BENZOIC ACID, P-SULFAMOYL BENZOIC ACID) WERE TESTED FOR MUTAGENICITY. CONTAMINANTS OTS & ITS ISOMER PTS WERE MUTAGENIC IN AMES TEST & BASC TEST IN DROSOPHILA. |
| F | 9-21 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| 輸送番号（UN） | UN 3261 8/PG 2 |
| 毒性 | LD50 orally in Rabbit: 4680 mg/kg |
| 税関コード | 29049020 |
| 危険文句（R） | 34-29-41-38 |
| 化審法 | (3)-1936 |
| 危険表示 | C,Xi |
| hazard_note | Corrosive |
| 安全措置（S） | 26-36/37/39-45-27-39 |
| 危険等級 | 8Eye Dam. 1Met. Corr. 1Skin Irrit. 2Skin Sens. 1 |
| 包装等級 | II |
| 貯蔵分類 | 8A - Combustible corrosive hazardous materials |
| 有害物質データ | 98-59-9(Hazardous Substances Data) |
用途
用途
塩化パラトルエンスルホニルは塩基の存在下にアルコールなどのヒドロキシ基をスルホニル化する。塩基としてはピリジン、N,N-ジメチル-4-アミノピリジン (DMAP)、水酸化ナトリウムなどが用いられ、概ね収率は良好である。
一般的な説明
Tosyl chloride is a white to gray powdered solid with a distinctive odor. It can be used in organic synthesis, to make nitriles, isocyanides and diimides.
製法・合成法
製造方法
Tosyl chloride is a by-product from the production of ortho-toluenesulfonyl chloride (a precursor for the synthesis of the common food additive and catalyst saccharin), via the chlorosulfonation of toluene:CH3C6H5+ SO2Cl2→ CH3C6H4SO2Cl + HCl
純化方法
Material that has been standing for a long time contains tosic acid and HCl and has m ca 65-68o. It is purified by dissolving (10g) in the minimum volume of CHCl3 (ca 25mL) filtered, and diluted with five volumes (i.e. 125mL) of pet ether (b 30-60o) to precipitate impurities. The solution is filtered, clarified with charcoal and concentrated to 40mL by evaporation. Further evaporation to a very small volume gives 7g of white crystals which are analytically pure, m 67.5-68.5o. (The insoluble material is largely tosic acid and has m 101-104o.) [Pelletier Chem Ind (London) 1034 1953.] It also crystallises from toluene/pet ether in the cold, from pet ether (b 40-60o) or *benzene. Its solution in diethyl ether has been washed with aqueous 10% NaOH until colourless, then dried (Na2SO4) and crystallised by cooling in powdered Dry-ice. It has also been purified by dissolving in *benzene, washing with aqueous 5% NaOH , then dried with K2CO3 or MgSO4, and distilled under reduced pressure and can be sublimed at high vacuum [Ebel Chem Ber 60 20861927]. [Beilstein 11 IV 375.]