4-Toluenesulfonyl chloride (HCID 7397)

概要

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.

名称と識別子

優先名称: 4-Toluenesulfonyl chloride
IUPAC: 4-methylbenzenesulfonyl chloride
現地名: p-トルエンスルホニルクロリド
英語名: Tosyl chloride
分子式: C7H7ClO2S
分子量: 190.65

名称と別名

4-Toluenesulfonyl chlorideRefChem:169391P-TOLUENESULFONYL CHLORIDE98-59-9Tosyl chloride4-Methylbenzenesulfonyl chloridep-Tosyl chloride4-methylbenzene-1-sulfonyl chloridep-Toluenesulphonyl chloridep-Tolylsulfonyl chloridep-Toluenesulfochloridetosylchloride

名称をさらに表示

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p-トルエンスルホンクロリドpトルエンスルホニルクロライドP-トルエンスルホニルクロライド塩化物塩化P-トルエンスルホニル塩化トシルパラトルエンスルホクロリド塩化 p-トルエンスルホニルp-トルエンスルホクロリド塩化4‐トルエンスルホニル4-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p-トルエンスルホニル=クロリド, 98%TsClTOS-CLPTSCPARA TOLUENE SULFONYL CHLORIDEp-toluenesulfonyl

p-Toluenesulfonic acid chloridep-Methylbenzenesulfonyl chloridepara-Toluenesulfonyl chloride4-Tosyl chlorideBenzenesulfonyl chloride, 4-methyl-4-toluene sulfonyl chloridep-Toluene sulphonyl chlorideToluenesulfonyl chloride

データベース識別子

CAS: 98-59-9
PubChem CID: 7397
DTXSID: DTXSID1052660
UNII: 027KYN78B4
EC Number: 202-684-8
Nikkaji: J3.580G

物性

構造計算による物性

XLogP: 3
極性表面積: 42.5 Å²
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

実験および物理化学的性質

Chemical ClassesToxic Gases & Vapors -> Acid Halides

SpringerMaterials PropertiesSchoenflies notation

LogP3.49

Density · 2 件

1.3 g/cm³

1.33 @25 °C

Color/Form · 2 件

CRYSTALS

TRICLINIC CRYSTALS FROM ETHER OR PETROLEUM ETHER

Solubility · 2 件

INSOL IN WATER; FREELY SOL IN ALCOHOL, BENZENE, ETHER

Solubility in water: reaction

物理化学的性質

融点: 65 · 65-69 °C(lit.)
沸点: 134 °C10 · 134 °C10 mm Hg(lit.)
比重(密度): 1 · 1,006 g/cm3
蒸気圧: 1 mm · 1 mm Hg ( 88 °C)
闪点: 128 °C · 128 °C
貯蔵温度: 30 °C · Store below +30°C.
溶解性: 0.2 g/mL、透明 · 塩化メチレン: 0.2 g/mL、透明
外見: 結晶性粉末
色: 白い
水溶解度: 加水分解
Merck: 14 · 14,9534
BRN: 607898 · 607898
Henry's Law Constant: 1 · 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 · 98-59-9(CAS DataBase Reference)
NISTの化学物質情報: 4 · Benzenesulfonyl chloride, 4-methyl-(98-59-9)
EPAの化学物質情報: p-Toluenesulfonyl chloride (98-59-9)

化学的性質

化学的特性White to yellow solid.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 5.7% (53 of 926) of reports.

Danger

H290 (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.

危険有害性情報

Regulatory Information · 3 件

Chemical: Benzenesulfonyl chloride, 4-methyl-

Status: Active Update: 12-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13242

4-Toluenesulphonyl chloride: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelCorrosive

Fire Hazards · 2 件

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Hazards Summary · 1 件

A skin, eye, and respiratory tract irritant; [HSDB] Reacts violently with water evolving hydrochloric acid; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation 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]

Reactive GroupAcyl Halides, Sulfonyl Halides, and Chloroformates

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Use dry powder, carbon dioxide. NO water. NO foam.

First Aid Measures · 4 件

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 .

First AidExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Safe StorageDry. Well closed. Store in an area without drain or sewer access.

Nonfire Spill ResponseExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Spillage Disposal · 1 件

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.

毒性情報

Adverse EffectsDermatotoxin - Skin burns.

Signs and Symptoms · 4 件

Cough.

Redness. Pain.

Sore throat.

ICSC Environmental DataThe substance is harmful to aquatic organisms.

Human Toxicity Excerpts · 3 件

...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 · 1 件

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.

安全データ

F: 9-21
wgk: 1
tsca: TSCA listed
ridadr: UN 3261 8/PG 2
毒性: LD50 orally in Rabbit: 4680 mg/kg
hs_code: 29049020
risk_code: 34-29-41-38
化審法: (3)-1936
hazard_code: C,Xi
hazard_note: Corrosive
safety_code: 26-36/37/39-45-27-39
hazard_class: 8
packing_group: II
Hazard Classifications: Eye Dam. 1Met. Corr. 1Skin Irrit. 2Skin Sens. 1
ストレージクラス: 8A - Combustible corrosive hazardous materials
有毒物質データの: 98-59-9(Hazardous Substances Data)

化学と産業

用途と製造

Uses · 2 件

Used to make other organic chemicals; [Hawley] Used to make food additives, foaming agents for plastics and rubber, riboflavin, antithrombotic drugs, and dye condensing agents; [eChemPortal: SIDSUNEP]

ORGANIC SYNTHESIS

Methods of ManufacturingMADE BY TREATING TOLUENE WITH CHLOROSULFONIC ACID.

General Manufacturing Information · 2 件

Benzenesulfonyl chloride, 4-methyl-: ACTIVE

10 OF 16 MERCURATED SULFONAMIDES TESTED AS BACTERICIDES & FUNGICIDES AGAINST E COLI, RHIZOCTONIA SOLANI, S AUREUS, A NIGER, & CHETOMIUM GLOBOSSUM WERE MORE TOXIC THAN ZINEB. SULFONAMIDES PREPD BY CONDENSING ANILINE BASE WITH P-TOLUENESULFONYL CHLORIDE IN PRESENCE OF PYRIDINE + BENZENE.

応用分野

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.

調製方法 · 2 件

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.]

上流・下流製品情報

上流原料

o-トルエンスルホニルクロリドトルエンクロロスルホン酸ベンゼンスルホニルクロリド

下流製品

アシッドレッド114 4'-[[4,5-ジヒドロ-3-メチル-5-オキソ-1-(4-スルホフェニル)-1H-ピラゾール-4-イル]アゾ]-4-[[4-[[(4-メチルフェニル)スルホニル]オキシ]フェニル]アゾ]-1,1'-ビフェニル-3-スルホン酸二ナトリウム 4-メチルベンゼンスルホン酸2-クロロエチル N1-(2,4-ジメチルフェニル)-N2-メチルホルムアミジン·塩酸塩 3-(2-フェノキシ-5-クロロフェニルアゾ)-4-ヒドロキシ-5-(トシルアミノ)ナフタレン-2,7-ビス(スルホン酸ナトリウム)p-トルエンスルホン酸ドデシル (4S)-4-hydroxy-3-methyl-2-prop-2-ynyl-cyclopent-2-en-1-one 3-アミノ-4-フェニルチオフェン-2-カルボン酸メチル N,N'-BIS(ETHYLENE)-P-TOLUENESULFONAMIDE Tracid Brilliant Red 10b イソキノリン-1-カルボニトリル 1-[(4-メチルフェニル)スルホニル]-1H-インドール-3-カルバルデヒド

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p-トルエンスルホニルクロリド

基本情報

概要