트리플루오로메탄술폰산

Trifluoromethanesulfonic acid

HCID 62406CAS 1493-13-6

기본 정보

표준 SMILES
O=S(=O)(O)C(F)(F)F
InChIKey
ITMCEJHCFYSIIV-UHFFFAOYSA-N
분자식
CHF3O3S
평균 분자량
150.08 g/mol

개요

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acid is a one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.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.

이름 및 식별자

우선 이름
Trifluoromethanesulfonic acid
IUPAC
trifluoromethanesulfonic acid
현지명
트리플루오로메탄술폰산
영어명
Trifluoromethanesulfonic acid
분자식
CHF3O3S
분자량
150.08

이름 및 동의어

Trifluoromethanesulfonic acid1493-13-6Triflic acidPerfluoromethanesulfonic acidTrifluoromethanesulphonic acidtfmsaTrifluoromethane sulfonic acidTfOHDTXSID2044397HOTfJE2SY203E8Trifluormethansulfonsaeure
이름 더 보기
트라이플루오로메탄설폰산트리플루오로메탄술폰산트리플릭산퍼플루오로메탄술폰산Triflatetrifluorormethanesulfonic acidTFMStrifluoromethanesulfonictriflic
DTXCID0024397CHEBI:485111,1,1-trifluoromethanesulfonic acidAgOTf cpdCu(OTf)2Eu(OTf)3TFMSA cpdRefChem:191595

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
0.3
극성 표면적
62.8 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
6
회전 가능 결합 수
0
무거운 원자 수
8

실험 및 물리화학적 성질

Chemical Classes · 3건

Other Classes -> Organic Acids

Ionic Liquids -> Fluorinated Ionic Liquids

Ionic Liquids

PFAS · 5건

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]

물리화학적 성질

녹는점
-40 °C · -40 °C
끓는 점
162 °C · 162 °C (lit.)
밀도
1.696 g/mL · 1.696 g/mL at 25 °C (lit.)
증기 밀도
5.2 · 5.2 (vs air)
증기압
8 mm · 8 mm Hg ( 25 °C)
굴절률
20 · n20/D 1.327(lit.)
화학적 성질 · 1건

트리플루오로메탄술폰산(TfOH)의 밀도는 1.696 g/cm³이다. TfOH는 다양한 유기 화합물을 잘 용해시키며, 많은 극성 유기 용매와 혼합 가능하다. 이는 다른 초산(예: 플루오로설폰산(FSO₃H, H₀ = –15) 또는 불화수소-안티모니플루오라이드(HF–SbF₅, H₀는 최저 –20))과는 다릅니다. TfOH는 물과 가수분해 반응을 일으키지 않으며, 대신 녹는점이 34°C인 일수화물을 형성한다. 이 화합물은 –40°C(녹는점)에서 162°C(끓는점)에 이르는 넓은 온도 범위에서 사용할 수 있다[1].

안전 및 규제

GHS 분류

GHS Classification · 6건

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]

유해성 정보

Regulatory Information · 4건

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 · 1건

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 · 2건

Met. Corr. 1 (92.8%)

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

안전 및 보호

Protective Action Criteria (PAC) · 3건

4.8 [mg/m3]

53 [mg/m3]

320 [mg/m3]

독성 정보

Health Effects · 1건

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 · 1건

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 · 1건

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).

안전 데이터

wgk
2
tsca
TSCA listed
ridadr
UN 3265 8/PG 2
독성
LD50 orally in Rabbit: 1605 mg/kg LD50 dermal Rat > 2000 mg/kg
HS 번호
29049020
risk_code
21/22-35-10

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

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)

용도 및 제조

Uses · 2건

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 · 2건

Not Known or Reasonably Ascertainable

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

응용 분야 · 3건

용도트리플루오로메탄술폰산은 펩티드 보호기를 제거하고 이성질체화와 중합을 촉매하기 위해 중합체에 대한 용매로 사용된다. 그 에스테르는 우수한 알킬화제이다. 무수물 (F3C-SO2)2O는 무색, 흡습성, 독성 액체이고(끓는점 84℃), 트리플루오로메탄술포닐기(triflate기)를 도입하기 위해 제조 화학에서 사용된다.

용도A 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.

일반 설명Trifluoromethanesulfonic 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.

공급사50 곳

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INTATRADE GmbH+49 3493/605464 · [email protected]
추가 설명 · 1건

정의ChEBI: 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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