p-トルエンスルホニルクロリド
4-Toluenesulfonyl chloride
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基本情報
- CAS
98-59-9- 標準SMILES
Cc1ccc(S(=O)(=O)Cl)cc1- InChIKey
YYROPELSRYBVMQ-UHFFFAOYSA-N- 分子式
- C7H7ClO2S
- 平均分子量
- 190.65 g/mol
- 単同位体質量
- 189.9855283
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-Toluenesulfochloridep-Toluenesulfonic acid chloride
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
tosylchloridep-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補完中
- XLogP
- 3
- 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
- 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
LogP
3.49
3.25
Density
1.3 g/cm³
1.33 @25 °C
Color/Form
CRYSTALS
TRICLINIC CRYSTALS FROM ETHER OR PETROLEUM ETHER
Solubility
INSOL IN WATER; FREELY SOL IN ALCOHOL, BENZENE, ETHER
Solubility in water: reaction
Flash Point128 °C c.c.
Boiling Point146 °C @ 15 MM HG
Melting Point
69-71 °C
69-71 °C
Vapor DensityRelative vapor density (air = 1): 6.6
Vapor Pressure
Vapor pressure, Pa at 25 °C: 0.16
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
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
Chemical: Benzenesulfonyl chloride, 4-methyl-
REACH registered substance: Tosyl chloride (EC: 202-684-8)
4-Toluenesulphonyl chloride: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelCorrosive
Fire Hazards
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
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]
化学と産業
用途と製造
Uses
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
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
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.]
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