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Methanesulfonyl chloride
メタンスルホニルクロリド · 塩化メタンスルホニル · メタンスルフォニルクロライド · 塩化メチルスルホニル · メタンスルホン酸クロライド · 化メタンスルホニル · メシルクロリド · メチルスルホニルクロリド
識別子と物理属性
| CAS No. | 124-63-0 |
|---|---|
| 分子式 | CH3ClO2S |
| 平均分子量 | 114.55 g/mol |
| 単同位体質量 | 113.95422802 g/mol |
| SMILES | CS(=O)(=O)Cl |
| InChIKey | QARBMVPHQWIHKH-UHFFFAOYSA-N |
| PubChem CID | 31297 |
| EC No. | 204-706-1 |
| DTXSID | DTXSID1021615 |
| 現地名 | メタンスルホニルクロリド |
化学・物理的性質
| XLogP | 0.4 |
|---|---|
| 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 | 0 |
| 重原子数 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 95.3 |
| 物質分類 | Toxic Gases & Vapors -> Acid Halides |
| SpringerMaterials Properties | Schoenflies notation |
| 臭い | Unpleasant odor |
| 密度 | 1.4805 at 18 °C/4 °CRelative density (water = 1): 1.51.4805 @ 18°C1.48 g/mL at 25 °C (lit.) |
| Viscosity | 1.33 centistokes at 25 °C |
| Color/Form | Pale yellow liquid |
| 溶解度 | Soluble in most organic solventsPractically insoluble in watersoluble in alcohol, etherSolubility in water: reactionクロロホルム、ヘキサンアルコール、エーテル、有機溶剤と混和します。水と混和しない。 |
| 引火点 | >110 °C>230 °F |
| 沸点 | 62 °C at 18 mm Hg161 °C at 730 mm Hgat 97.3kPa: 161 °C60 °C/21 mmHg (lit.) |
| Decomposition | When heated to decompositionit emits toxic vapors of /sulfur oxides and hydrogen chloride/. |
| 融点 | Freezing point: -32 °C-33°C |
| 蒸気密度 | 3.9 (Air = 1)Relative vapor density (air = 1): 4.0 |
| 蒸気圧 | 3.001-8.9hPa at 20-25℃ |
| 屈折率 | n20/D 1.452(lit.) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 液体 |
| 色 | クリア |
| Merck | 14,5955 |
| BRN | 506297 |
| ヘンリー定数 | 2.2×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 湿気に敏感 |
| InChI | 1S/CH3ClO2S/c1-5(2,3)4/h1H3 |
| InChIKey | QARBMVPHQWIHKH-UHFFFAOYSA-N |
| SMILES | CS(Cl)(=O)=O |
| LogP（分配係数） | -0.78-1.27 at 25℃ |
| 表面張力 | 72.5mN/m at 1.1g/L and 21℃ |
| CAS データベース | 124-63-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Methanesulfonyl chloride(124-63-0) |
| EPAの化学物質情報 | Methanesulfonyl chloride (124-63-0) |
化学的特性
Colorless to yellow liquid
化学性质
刺激臭のある色の液体．沸点60℃（21 mmHg）
安全性と法規制
| GHS 分類 | DangerH290 (47.5%): May be corrosive to metals [Warning Corrosive to Metals]P234, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P333+P317, P361+P364, P362+P364, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 314 reports by companies from 27 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301: Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Hazards Identification | Toxic/poison by inhalation (TIH/PIH) |
| 規制情報 | Chemical: Methanesulfonyl chlorideMethanesulfonyl chloride is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanesulfonyl chloride 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)SP - indicates a substance that is identified in a proposed Significant New Use Rule.Status: Active Update: 10-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13541Methanesulphonyl chloride: HSNO Approval: HSR004556 Approved with controls |
| 輸送ラベル（DOT） | Poison Inhalation Hazard Corrosive |
| 火災危険 | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 健康有害性 | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:· TOXIC and/or CORROSIVEinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. |
| 有害性の概要 | Highly corrosive to skin[Quick CPC] It is tear drawing and corrosive to the skin and respiratory tract[ICSC] May form hydrogen chloride gas on contact with water or moisture, although experiments at Argonne National Laboratory have shown essentially no reaction with waterHighly toxic by ingestion, inhalation, and skin absorption[CAMEO] Slowly hydrolyzed by water forming hydrochloric acidA lachrymatorCorrosive to tissue[EPA OHM/TADS] Hydrolyzed by water evolving acidic gasCauses burnsInhalation may cause corrosive injuries to upper respiratory tract and lungs[Aldrich MSDS] |
| 輸送番号・ガイド（DOT） | 3246 156 |
| 反応性グループ | Acyl Halides, Sulfonyl Halides, and Chloroformates |
| UN 分類 | UN Hazard Class: 6.1UN Subsidiary Risks: 8UN Pack Group: I |
| Special Reports | European Chemicals BureauIUCLID Dataset, Methanesulphonyl chloride (CAS # 124-63-0) describes toxicological information and use patterns supplied to the European Union by industry as of 2000. |
| TSCA 要件 | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Methanesulfonyl chloride is included on this list. |
| Reactivity Alerts | Water-Reactive |
| 消火 | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:Use water spray, powder, foam, carbon dioxide. |
| 応急処置措置 | Fresh air, rest. Refer immediately for medical attention.Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention.Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention. |
| 漏出応急措置 | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| 応急処置 | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:General First Aid: |
| 安全保管 | Separated from food and feedstuffs and incompatible materials. Dry. Well closed. Keep in a well-ventilated room. Store in an area without drain or sewer access. |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA).TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016]. |
| 消火手順 | If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible Use "alcohol" foam, dry chemical or carbon dioxide. |
| 清掃方法 | Environmental considerations- land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.Environmental considerations- water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.Environmental considerations- air spill: Apply water spray or mist to knock down vapors. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: |
| 処分方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| 漏出処分 | Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable dry containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. |
| Preventive Measures | If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment Wash away any material which may have contacted the body with copious amounts of water or soap and water.SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| 生態毒性値 | LC50 Menidia beryllina (inland silverside, length 40-100 mm) 15 mg/L/96 hrstatic, 20 °C, pH 7.6-7.9, hardness 55 mg/L CaCO3LC50 Menidia beryllina (inland silverside) 15 mg/L/96 hrstatic bioassay in synthetic seawater at 23 °C, mild aeration applied after 24 hr.LC50 Lepomis macrochirus (bluegill sunfish) 11 mg/L/96 hrstatic bioassay in freshwater at 23 °C, mild aeration applied after 24 hrLC50 Lepomis macrochirus (bluegill, length 33-75 mm) 11 mg/L/96 hrstatic, 23 °C, pH 7.6-7.9, hardness 55 mg/L CaCO3 |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6.1(SRC), determined from a structure estimation method(2), indicates that methanesulfonyl chloride is expected to have very high mobility in soil(SRC). Volatilization of methanesulfonyl chloride from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.4X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Methanesulfonyl chloride is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.1 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2007).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6.1(SRC), determined from a structure estimation method(2), indicates that methanesulfonyl chloride is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.4X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 15 hours and 11 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 1.9(SRC), from an estimated log Kow of 1.3(SRC) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Methanesulfonyl chloride hydrolyzes slowly in water(7). Biodegradation data were not available(SRC, 2007).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methanesulfonyl chloride, which has an estimated vapor pressure of 3.1 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methanesulfonyl chloride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 150 days(SRC), calculated from its rate constant of 1.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Methanesulfonyl chloride does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4). |
| 有害作用 | Dermatotoxin - Skin burns. |
| 暴露経路 | The substance can be absorbed into the body by inhalation, by ingestion and through the skin. |
| Signs and Symptoms | Cough. Sore throat. Burning sensation. Laboured breathing. Shortness of breath.Redness. Pain. Blisters.Redness. Pain. Severe burns.See Inhalation. |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of methanesulfonyl chloride can be estimated to be 6.1(SRC). According to a classification scheme(2), this estimated Koc value suggests that methanesulfonyl chloride is expected to have very high mobility in soil. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Methanesulfonyl chloride is corrosive to eyes, skin, and mucous membranes. |
| Artificial Pollution Sources | Methanesulfonyl chloride's production and use in flame-resistant products, as a stabilizer for liquid sulfur trioxide, as a biological chemical, as a chemical intermediate(1) in the photographic, fiber dye, agricultural, and pharmaceutical industries, a catalyst, curing agent, and chlorinating agent(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Bioconcentration | An estimated BCF of 1.9 was calculated for methanesulfonyl chloride(SRC), using an estimated log Kow of 1.3(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for methanesulfonyl chloride is estimated as 4.4X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methanesulfonyl chloride is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 15 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 11 days(SRC). Methanesulfonyl chloride's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Methanesulfonyl chloride is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.1 mm Hg(SRC), determined from a fragment constant method(3). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ The 1-hr and 4-hr inhalation LC50 values in rats were approximately 200 ppm and 25 ppm, respectively. Clinical signs during exposure included salivation and marked eye and respiratory tract irritation. Effects noted postexposure included lethargy, persistent disturbances in respiratory pattern, decreases in body weight and food and water intake, lung congestion, and damage to the corneal surface of the eyes.[Bingham, E.Cohrssen, B.Powell, C.H.Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 7:747]/LABORATORY ANIMALS: Acute Exposure/ In rabbits, irrigation of the eye 20 to 30 sec after instillation reduced the response, but corneal opacity and congestion of the iris with no pupillary light reaction were still noted.[Bingham, E./LABORATORY ANIMALS: Acute Exposure/ A single dermal application of 2000 mg/kg to rabbits killed all animals within 24 hr. No deaths occurred following a dermal application of 200 mg/kg.[Bingham, E./LABORATORY ANIMALS: Acute Exposure/ The oral LD50 in rats was 255 mg/kg and there were clinical signs of hypertonia, general distress, and stomach irritation.[Bingham, E.For more Non-Human Toxicity Excerpts (Complete) data for METHANESULFONYL CHLORIDE (6 total), please visit the HSDB record page. |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | PB2790000 |
| 輸送番号（UN） | UN 3246 |
| 税関コード | 29049095 |
| 危険文句（R） | 24/25-26-34-37-35-22-41 |
| 化審法 | (2)-1583 |
| 消防法 | 危-4-3-III |
| 危険表示 | T+,T,C |
| hazard_note | Toxic/Corrosive |
| 安全措置（S） | 26-28-36/37/39-45-25-28A |
| 危険等級 | 6.1Acute Tox. 2 InhalationAcute Tox. 3 OralAcute Tox. 4 DermalEye Dam. 1Met. Corr. 1Skin Corr. 1BSkin Sens. 1STOT SE 3 |
| 包装等級 | I |
| 毒劇物取締法 | 毒物 |
| 自然発火温度 | 435°C |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 有害物質データ | 124-63-0(Hazardous Substances Data) |
用途
用途
主要な用途は、難燃化剤、写真関連、線維染料、農業用化学製品、製薬における合成中間体であり、安定化剤、触媒、硬化剤、塩素化剤として使用される。
使用
Methanesulfonyl chloride is used as a reagent for conversion of alcohols to mesylate esters such as methanesulfonate, which is an intermediate in substitution reactions, elimination reactions, reductions, and rearrangement reactions viz. Beckmann rearrangement. It is an electrophile and acts as a source of CH3SO2+ group. It is also used to prepare beta-chloro sulfones, methanesulfonamide and heterocyclic compounds containing five membered sultones.
一般的な説明
A pale yellow corrosive liquid. More dense than water and insoluble in water. Very toxic by ingestion, inhalation, or skin absorption.
製法・合成法
合成方法
メタンスルホン酸と塩化チオニルとの反応または水存在下メタンチオールと塩素との反応
純化方法
Distil the sulfonyl chloride from P2O5 under vacuum. It is a strong IRRITANT.[Beilstein 4 IV 27.]