Methanesulfonyl chloride

HCID 31297CAS 124-63-0

基本情報

標準SMILES
CS(=O)(=O)Cl
InChIKey
QARBMVPHQWIHKH-UHFFFAOYSA-N
分子式
CH3ClO2S
平均分子量
114.55 g/mol
単同位体質量
113.95422802

概要

Methanesulfonyl chloride appears as a pale yellow corrosive liquid. More dense than water and insoluble in water. Very toxic by ingestion, inhalation, or skin absorption.

名称と識別子

優先名称
Methanesulfonyl chloride
IUPAC
methanesulfonyl chloride
現地名
メタンスルホニルクロリド
英語名
Methanesulfonyl chloride
分子式
CH3ClO2S
分子量
114.55

名称と別名

Methanesulfonyl chloride124-63-0Mesyl chlorideMethanesulphonyl chlorideMethyl sulfochlorideMETHYLSULFONYL CHLORIDEChloro methyl sulfoneMethanesulfonic acid chlorideMethanesulfuryl chlorideMethyl sulfonyl chlorideChloromethyl sulfoneDTXSID1021615
名称をさらに表示
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MSCIメチルスルホクロリドメタンスルホン酸クロリドメタンスルホニルクロライド塩化メシルメタンスルホニル クロリドメシルクロライドMSCLMSCMSCICH3SO2ClmethanesulfonylJJHXLMethane sufonyl chloride
METHANE SULFONYL CHLORIDEB17EWY1R7QNSC-15039DTXCID601615RefChem:156944204-706-1MesylchlorideNSC 15039

データベース識別子

CAS
124-63-0
PubChem CID
31297
DTXSID
DTXSID1021615
UNII
B17EWY1R7Q
EC Number
204-706-1
Nikkaji
J2.507K

物性

構造計算による物性

XLogP
0.4
極性表面積
42.5 Ų
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

実験および物理化学的性質

Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesSchoenflies notation
OdorUnpleasant odor
Density · 3 件

1.4805 at 18 °C/4 °C

Relative density (water = 1): 1.5

1.4805 @ 18°C

Viscosity1.33 centistokes at 25 °C
Color/FormPale yellow liquid

物理化学的性質

融点
-33 °C · -33°C
沸点
60 °C/21 · 60 °C/21 mmHg (lit.)
比重(密度)
1.48 g/mL · 1.48 g/mL at 25 °C (lit.)
蒸気圧
3.001 · 3.001-8.9hPa at 20-25℃
屈折率
20 · n20/D 1.452(lit.)
闪点
230 °F · >230 °F

化学的性質

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)

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H290 (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.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

危険有害性情報

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 5 件

Chemical: Methanesulfonyl chloride

Methanesulfonyl 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/13541

Methanesulphonyl chloride: HSNO Approval: HSR004556 Approved with controls

DOT LabelPoison Inhalation Hazard Corrosive
Fire Hazards · 3 件

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.

Health Hazards · 2 件

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards Summary · 1 件

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 water; Highly toxic by ingestion, inhalation, and skin absorption; [CAMEO] Slowly hydrolyzed by water forming hydrochloric acid; A lachrymator; Corrosive to tissue; [EPA OHM/TADS] Hydrolyzed by water evolving acidic gas; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Highly toxic by ingestion, inhalation, and skin absorption; [Aldrich MSDS]

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 件

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.

Accidental Release Measures · 2 件

· 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.

First Aid · 2 件

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

General First Aid:

Safe StorageSeparated 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.
Exposure Control and Personal Protection · 2 件

· 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].

毒性情報

Ecotoxicity Values · 4 件

LC50 Menidia beryllina (inland silverside, length 40-100 mm) 15 mg/L/96 hr; static, 20 °C, pH 7.6-7.9, hardness 55 mg/L CaCO3

LC50 Menidia beryllina (inland silverside) 15 mg/L/96 hr; static bioassay in synthetic seawater at 23 °C, mild aeration applied after 24 hr.

LC50 Lepomis macrochirus (bluegill sunfish) 11 mg/L/96 hr; static bioassay in freshwater at 23 °C, mild aeration applied after 24 hr

LC50 Lepomis macrochirus (bluegill, length 33-75 mm) 11 mg/L/96 hr; static, 23 °C, pH 7.6-7.9, hardness 55 mg/L CaCO3

Environmental Fate · 3 件

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).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation, by ingestion and through the skin.
Signs and Symptoms · 4 件

Cough. Sore throat. Burning sensation. Laboured breathing. Shortness of breath.

Redness. Pain. Blisters.

Redness. Pain. Severe burns.

See Inhalation.

ICSC Environmental DataThe substance is harmful to aquatic organisms.

法規制情報

TSCA Requirements · 2 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.

安全データ

wgk
2
tsca
TSCA listed
rtecs
PB2790000
ridadr
UN 3246
hs_code
29049095
risk_code
24/25-26-34-37-35-22-41

化学と産業

用途と製造

Uses · 6 件

Used as an intermediate in the production of drugs, flame retardants, and other chemicals; Also used as a stabilizer, catalyst, curing agent, and chlorinating agent; Has been detected in air samples at a pulp mill that used chlorine-containing bleaching agents; [HSDB]

Pulp and Paper Processing [Category: Industry]

Intermediate; flame-resistant products; stabilizer for liquid sulfur trioxide; biological chemicals.

Chemical intermediate for busulfan (human antineoplastic agent)

Chemical intermediate for glucocorticoids used in human medicine

Chemical intermediate for antiinflammatory agents in human medicine

U.S. Production · 5 件

2023: 500,000 - <1,000,000 lb

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5456]

Industry UsesIntermediate
Methods of Manufacturing · 2 件

Made commercially by ... the sulfochlorination of methane.

Prepared from sulfur trioxide and methane

Formulations/PreparationsGrade: 98%, 99%+
General Manufacturing Information · 2 件

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Methanesulfonyl chloride: ACTIVE

応用分野 · 3 件

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.

調製方法

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.]

上流・下流製品情報

下流製品

ニメスリド9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione21-phosphate piperazine saltアズトレオナム2-N-(メタンスルホンアミド)フェニルボロン酸アムサクリンラロキシフェンプロパンスルトン5-アミノサリチル酸1-(Tetrahydro-2H-pyran-4-yl)hydrazineブスルファン(4S)-4-hydroxy-3-methyl-2-prop-2-ynyl-cyclopent-2-en-1-one5,5'-アゾビスサリチル酸

関連反応

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