トリフルオロメタンスルホン酸

Trifluoromethanesulfonic acid

HCID 62406CAS 1493-13-6

基本情報

標準SMILES
O=S(=O)(O)C(F)(F)F
InChIKey
ITMCEJHCFYSIIV-UHFFFAOYSA-N
分子式
CHF3O3S
平均分子量
150.08 g/mol

概要

Triflic acid is a one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines. It is a perfluoroalkanesulfonic acid and a one-carbon compound. It is a conjugate acid of a triflate.

名称と識別子

優先名称
Trifluoromethanesulfonic acid
IUPAC
trifluoromethanesulfonic acid
現地名
トリフルオロメタンスルホン酸
英語名
Trifluoromethanesulfonic acid
分子式
CHF3O3S
分子量
150.08

名称と別名

Trifluoromethanesulfonic acid1493-13-6Triflic acidPerfluoromethanesulfonic acidTrifluoromethanesulphonic acidtfmsaTrifluoromethane sulfonic acidTfOHDTXSID2044397HOTfJE2SY203E8Trifluormethansulfonsaeure
名称をさらに表示
トリフルオロメタンスルホン酸フルオラードFC-24三フッ化メタンスルホン酸ペルフルオロメタンスルホン酸トリフラートトリフル酸トリメシラートトリフルオロメタンスルホン酸, 99+%Triflatetrifluorormethanesulfonic acidTFMStrifluoromethanesulfonictriflic
DTXCID0024397CHEBI:485111,1,1-trifluoromethanesulfonic acidAgOTf cpdCu(OTf)2Eu(OTf)3TFMSA cpdRefChem:191595

データベース識別子

CAS
1493-13-6
PubChem CID
62406
DTXSID
DTXSID2044397
ChEMBL
CHEMBL1236265
ChEBI
CHEBI:48511
UNII
JE2SY203E8
EC Number
216-087-5
Nikkaji
J12.301C

物性

構造計算による物性

XLogP
0.3
極性表面積
62.8 Ų
水素結合供与体数
1
水素結合受容体数
6
回転可能結合数
0
重原子数
8

実験および物理化学的性質

Chemical Classes · 3 件

Other Classes -> Organic Acids

Ionic Liquids -> Fluorinated Ionic Liquids

Ionic Liquids

PFAS · 5 件

PFAS -> Perfluorosulfonic acids

PFAS -> Ultra Short Chain PFsulfonic acids

PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008

PFAS -> Suspected persistent, mobile, toxic (PMT) PFAS or PFAS-like compounds

PFAS -> PFAS with analytical method available

SpringerMaterials PropertiesSchoenflies notation
Food AdditivesUse unspecified -> FDA Substance added to food
Density1.696 @25 °C
Boiling Point162 °C @760 [mm Hg]

物理化学的性質

融点
-40 °C · -40 °C
沸点
162 °C · 162 °C (lit.)
比重(密度)
1.696 g/mL · 1.696 g/mL at 25 °C (lit.)
蒸気密度
5.2 · 5.2 (vs air)
蒸気圧
8 mm · 8 mm Hg ( 25 °C)
屈折率
20 · n20/D 1.327(lit.)

化学的性質

化学性质強酸(pK 約~14)

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H290 (92.8%): May be corrosive to metals [Warning Corrosive to Metals]

P234, P260, P261, P264, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P330, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2365 reports by companies from 34 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

危険有害性情報

Regulatory Information · 4 件

Chemical: Methanesulfonic acid, trifluoro-

Methanesulfonic acid, 1,1,1-trifluoro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanesulfonic acid, 1,1,1-trifluoro- 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)

Status: Active Update: 03-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5311

Trifluoromethanesulphonic acid: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

Highly corrosive to skin; [Quick CPC] One of the strongest acids known. May cause burns; [Merck Index] Oral LD50 (rat) is between 500 and 2,000 mg/kg; An acute dermal toxicity study of rats at 2,000 mg/kg produced extensive and severe local skin effects considered to be life threatening; 50 mg/kg doses were tolerated and showed no significant adverse effects at necropsy; No evidence of skin sensitization in guinea pigs; No evidence of mutagenicity; [EPA TSCA] Causes burns; Inhalation of high concentration can cause chemical pneumonitis; [Alfa Aesar MSDS]

Hazard Classes and Categories · 2 件

Met. Corr. 1 (92.8%)

Serious eye damage/eye irritation - Category 2A-2B

安全と保護具

Protective Action Criteria (PAC) · 3 件

4.8 [mg/m3]

53 [mg/m3]

320 [mg/m3]

毒性情報

Health Effects · 1 件

Silver itself is not toxic to humans, but most silver salts are. In large doses, silver and compounds containing it can be absorbed into the circulatory system and become deposited in various body tissues, leading to argyria, which results in a blue-grayish pigmentation of the skin, eyes, and mucous membranes. Argyria is rare, and although, so far as known, this condition does not otherwise harm a person's health, it is disfiguring and usually permanent. Mild forms of argyria are sometimes mistaken for cyanosis. (L809)

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesOral (L808) ; inhalation (L808) ; dermal (L808)
Toxicity Summary · 1 件

Metallic silver is oxidized and may deposit in the tissues, causing arygria. The silver ion is known to inhibit glutathione peroxidase and NA+,K+-ATPase activity, disrupting selenium-catalyzed sulfhydryl oxidation-reduction reactions and intracellular ion concentrations, respectively. Silver nanoparticles are believed to disrupt the mitochondrial respiratory chain, causing oxidative stress, reduced ATP synthesis, and DNA damage. (L808, A243, A244, A245, A246)

Signs and Symptoms · 1 件

Exposure to high levels of silver for a long period of time may result in a condition called arygria, a blue-gray discoloration of the skin and other body tissues. Argyria is a permanent effect but does not appear to be harmful to health. Exposure to high levels of silver in the air has resulted in breathing problems, lung and throat irritation, and stomach pains. Skin contact with silver can cause mild allergic reactions such as rash, swelling, and inflammation in some people. (L808)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

F
3-10
wgk
2
tsca
TSCA listed
ridadr
UN 3265 8/PG 2
毒性
LD50 orally in Rabbit: 1605 mg/kg LD50 dermal Rat > 2000 mg/kg
hs_code
29049020

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Silver and its compounds can be absorbed via inhalation, while silver compounds can also be absorbed orally and dermally. It distributes throughout the body in the blood, particularily to the liver. Insoluble silver salts are transformed into soluble silver sulfide albuminates, bind to amino or carboxyl groups in RNA, DNA, and proteins, or are reduced to metallic silver by ascorbic acid or catecholamines. Metallic silver is oxidized and may deposit in the tissues, causing arygria. Silver is eliminated primarily in the faeces. (L808)

用途と製造

Uses · 2 件

Used as a catalyst, solvent for ESR, acid titrant, and with trifluoroacetic acid in peptide synthesis; [Merck Index]

Silver trifluoromethanesulfonate is used in inorganic and organometallic chemistry to replace halide anions or ligands. (L833)

U.S. Production2023: 26,136 lb
Industry UsesNot Known or Reasonably Ascertainable
Use ClassificationPFAS -> Ultra Short Chain PFsulfonic acids
General Manufacturing Information · 2 件

Not Known or Reasonably Ascertainable

Methanesulfonic acid, 1,1,1-trifluoro-: ACTIVE

応用分野 · 5 件

解説トリフルオロメタンスルホン酸,トリフルオロメタンスルホンサン,CHF3O3S(150.07).CF3SO3H.略称TFSA.メタンスルホニルクロリドの電解フッ素化によって得られるトリフルオロメタンスルホニルフルオリドの加水分解で合成される.無色の液体.融点-34 ℃,沸点162 ℃.d251.698.空気中で白煙を生じ,一水和物結晶になる.水,有機溶媒に可溶.硫酸より強い超強酸の一種で,有機合成反応触媒として用いられる.皮膚や眼をはげしく刺激する.

用途有機合成原料(重合触媒、スルホン化剤、脱水剤)、溶媒(たん白質、ポリマー)。

用途試薬,触媒,医薬,農薬原料

使用A cost-effective process for synthesizing daidzein was developed by Hai Cao and colleagues[1]. A two-step synthesis of daidzein (Friedel–Crafts acylation and [5+1] cyclization) was developed via the employment of trifluoromethanesulfonic acid (TfOH) as an effective promoting reagent. Due to the facilitating effect of TfOH, the Friedel–Crafts acylation was completed within 10 min at 90 °C and the [5+1] cyclization was completed within 180 min at 25 °C.

一般的な説明Trifluoromethanesulfonic acid is a strong organic acid. It can be prepared by reacting bis(trifluoromethylthio)mercury with H2O2. On mixing with HNO3, it affords a nitrating reagent (a nitronium salt). This reagent is useful for the nitration of aromatic compounds. Its dissociation in various organic solvents has been studied.

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補足説明 · 1 件

定義ChEBI: Trifluoromethanesulfonic acid is a one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines. It is a one-carbon compound and a perfluoroalkanesulfonic acid. It is a conjugate acid of a triflate.

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