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Trifluoromethanesulfonic Anhydride

Trifluoromethanesulfonic Anhydride

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Trifluoromethanesulfonic anhydride Cov ntaub ntawv yooj yim
Khoom npe: Trifluoromethanesulfonic anhydride
Synonyms: Trifluoromethanesulfonic anhydlladium(0);Trifluoromethanesulfonic anhydride purum, >{{0}}.0% (T); Trifluoromethanesulfonic anhydride tov 1 M hauv methylene chloride; Triflic anhydride tov; 7561347, DT: 23.1 1.2016) RE-EXPORT; TRIFLUOROMETHANE SULFONIC ANHYDRID (ORIG INAL IMPORT VIDE BE.NO; Trifluoromethanesulfonic anhydride kua; Methanesulfonic acid, trifluoro-, anhydride
CAS: 358-23-6
MF: C2F6O5S2
MW: 282.14
EINECS: 206-616-8
Khoom Categories: organofluorine compounds; Pharmaceutical intermediates; Pharmacetical; Organic Fluorides; 358-23-6; bc0001
Mol File: 358-23-6.mol
Trifluoromethanesulfonic anhydride Structure
 
Trifluoromethanesulfonic anhydride Chemical Properties
Melting point -80 degree
Boiling point 81-83 degree (lit.)
ceev 1.677 g / mL ntawm 25 degree (lit.)
vapor ceev 5.2 (vs huab cua)
vapor siab 8 hli Hg (20 degree)
Refractive Index n20 / D 1.321 (lit.)
RTECS PB 2772000
Fp 81-83 degree
cia temp. Khaws hauv qab +30 degree .
solubility Miscible nrog dichloromethane. Immiscible nrog hydrocarbons.
daim ntawv Ua kua
Specific Gravity 1.677
xim Ntshiab xim tsis muaj xim rau lub teeb xim av
Dej Solubility reacts hnyav nrog dej
rhiab heev Moisture Sensitive
BRN 1813600
Kev ruaj ntseg: Hygroscopic, Moisture Sensitive
InChIKey WJKHJLXJJJATHN-UHFFFAOYSA-N
LogP 0.3 ntawm 25 degree
CAS DataBase Reference 358-23-6(CAS DataBase Reference)
NIST Chemistry Reference Trifluoromethanesulfonic anhydride (358-23-6)
EPA Tshuaj Registry System Methanesulfonic acid, trifluoro-, anhydride (358-23-6)
 
Cov ntaub ntawv kev nyab xeeb
Hazard Codes C
Risk Statements 14-21/22-34-35-22-40
Cov lus hais txog kev nyab xeeb 26-36/37/39-43-45-8
RIDADR UN 3265 8/PG 2
WGK Germany 3
F 10-21
Ceeb toom Corrosive
TSCA Yog lawm
HazardClass 8
PackingGroup I
HS Code 29049020
Toxicity LD50 qhov ncauj hauv Luav: 1012 mg / kg
 
MSDS Cov Ntaub Ntawv
Tus kws kho mob Lus
Trifluoromethanesulfonic anhydride Lus Askiv
ACROS Lus Askiv
SigmaAldrich Lus Askiv
ALFA Lus Askiv
 
Trifluoromethanesulfonic anhydride Kev siv thiab kev sib xyaw
Kev piav qhia Trifluoromethanesulfonic anhydride, tseem hu ua triflic anhydride, tau ua pov thawj los ua ib qho reagent txawv tshaj plaw rau ntau yam kev hloov pauv. Raws li kev lag luam thiab yooj yim muaj reagent, Nws tau dav siv nyob rau hauv hluavtaws chemistry vim nws siab electrophilicity. Muab nws txoj kev sib raug zoo siab rau O-nucleophiles, cov tshuaj tiv thaiv nrog cawv, carbonyls, sulfur phosphorus- thiab iodine oxides ntawm kev tsim cov triflates sib raug zoo heev. Raws li ib qho ntawm cov thawj coj tawm hauv pawg hauv cov organic chemistry, cov triflates tsim tawm tom qab ntawd qhib qhov rooj rau ntau qhov kev hloov pauv hauv qab, suav nrog (tab sis tsis txwv rau) kev hloov pauv, cov txheej txheem sib txuas, cov tshuaj tiv thaiv redox, thiab kev kho dua tshiab[1-2] .
Chemical Properties clear colorless mus rau lub teeb xim av kua
Siv Trifluoromethanesulfonic Anhydride yog ib qho khoom siv hluav taws xob muaj zog siv hauv cov tshuaj synthesis los qhia txog pawg triflyl.
Siv Trifluoromethanesulfonic anhydride yog siv los hloov phenols thiab imine rau hauv triflic ester thiab NTf pawg. Nws yog ib qho muaj zog electrophile siv rau kev qhia txog triflyl pawg hauv tshuaj synthesis. Nws ua hauj lwm raws li ib tug reagent nyob rau hauv kev npaj ntawm alkyl thiab vinyl triflates, thiab rau stereoselective synthesis ntawm mannosazide methyl uronate pub. Nws ua raws li lub zog rau glycosylation nrog anomeric hydroxy qab zib los npaj polysaccharides.
Txhais ChEBI: Triflic anhydride yog organosulfonic anhydride. Nws muaj feem cuam tshuam nrog triflic acid.
Reactivity Profile Electrophilic activation ntawm tertiary thiab theem nrab amides nrog triflic anhydride (Tf2O; rifluoromethanesulfonic anhydride) nyob rau hauv cov mob me ua rau nce mus rau iminium thiab imino triflates, raws li, uas yuav siv tau raws li ntau yam reagents los teb nrog ntau yam C-, N-, O- thiab S -nucleophiles rau kev hloov pauv ntawm amide muaj nuj nqi rau hauv cov khoom sib txawv. Lwm cov nucleophiles uas muaj cov pa oxygen, xws li sulfoxides thiab phosphorus oxides, kuj tuaj yeem raug kev tawm tsam nucleophilic nrog Tf2O los tsim thionium triflate, electrophilic P-hom, thiab phosphonium triflate. Cov hom nquag nquag nquag no tuaj yeem nkag mus rau qhov kev hloov pauv nucleophilic rau kev hloov pauv ntxiv. Tsis tas li ntawd, vim muaj cov khoom siv hluav taws xob muaj zog, Tf2O yog qhov ua rau muaj kev cuam tshuam nrog cov nucleophiles uas tsis muaj zog xws li nitrile pawg lossis qee cov tshuaj heterocyclic uas muaj nitrogen. Tsis tas li ntawd, Tf2O kuj tau siv los ua ib qho radical trifluoromethylation thiab trifluorometh ylthiolation reagent los ntawm kev tso tawm SO2 los yog deoxygenation txheej txheem rau cov synthesis ntawm trifluoromethylated thiab trifluoromethylthiolated compounds [2].
Hazard Tej zaum yuav corrosive rau hlau. Ua phem yog nqos. Ua rau tawv nqaij kub hnyiab thiab qhov muag puas.
Flammability thiab Explosibility Tsis cais
Synthesis Lub synthesis ntawm Trifluoromethanesulfonic anhydride yog raws li nram no:
Ib qho qhuav, {{0}}ml., round-bottomed flask yog them nrog 36.3 g. (0.242 mole) ntawm trifluoromethanesulfonic acid (Note 1) thiab 27.3 g. (0.192 mole) ntawm phosphorus pentoxide (Note 2). Lub hwj yog nres thiab tso cai rau sawv ntsug ntawm chav sov li 3 teev. Thaum lub sij hawm no cov tshuaj tiv thaiv sib tov hloov los ntawm ib tug slurry mus rau ib tug khoom loj. Lub raj mis haum nrog lub taub hau luv-txoj kev distilling thiab ua kom sov ua ntej nrog cov kwj ntawm cov cua kub los ntawm rab phom kub thiab tom qab ntawd nrog cov nplaim taws los ntawm lub qhov cub me me.

Lub hwj yog rhuab kom txog thaum tsis muaj ntxiv trifluoromethanesulfonic anhydride distills, bp 82-115 degree, yielding 28.4-31.2 g. (83-91%) ntawm anhydride, kua tsis muaj xim. Txawm hais tias cov khoom no yog cov ntshiab txaus rau kev siv hauv cov kauj ruam tom ntej, cov kua qaub ntxiv tuaj yeem raug tshem tawm los ntawm anhydride los ntawm cov txheej txheem hauv qab no. 3.2 g ntawm slurry. phosphorus pentoxide nyob rau hauv 31.2 g. ntawm crude anhydride yog stirred nyob rau hauv chav tsev kub nyob rau hauv ib tug stoppered hwj rau 18 teev. Tom qab cov tshuaj tiv thaiv lub raj mis tau haum nrog lub taub hau luv-txoj kev distilling, nws yog rhuab nrog roj da dej, yielding 0.7 g. ntawm forerun, bp 74-81 degree, ua raws li 27.9 g. ntawm cov ntshiab trifluoromethanesulfonic acid anhydride, bp 81-84 degree.
synthesis of Trifluoromethanesulfonic anhydride.png
khaws cia Khaws rau hauv qhov chaw txias, qhuav, zoo cua txias. Moisture rhiab heev.
Txoj Kev Purification Nws tuaj yeem npaj tau tshiab los ntawm cov kua qaub anhydrous (11.5g) thiab P2O5 (11.5g, lossis ib nrab qhov hnyav) los ntawm qhov chaw sov so rau 1 teev, distilling tawm cov khoom uas tsis muaj zog ces distil nws los ntawm ib tug luv luv Vigreux kem. Nws tau yooj yim hydrolysed los ntawm H2O thiab decomposes appreciably tom qab ob peb hnub kom tso tawm SO2 thiab tsim cov kua nplaum. Khaws nws qhuav ntawm qhov kub thiab txias. [Burdon et al. J Chem Soc 2574 1957, Beard et al. J Org Chem 38 373 1973, Beilstein 3 IV 35.]
Cov ntaub ntawv [1] Haoqi Zhang. "Trifluoromethanesulfonic Anhydride nyob rau hauv Amide Activation: Lub Tuam Txhab Muaj Zog rau Forge Heterocyclic Cores." TCIMAIL (2021).
[2] Dr. Qixue Qin, Prof. Dr. Ning Jiao, Zengrui Cheng. "Kev siv tsis ntev los no ntawm Trifluoromethanesulfonic Anhydride hauv Organic Synthesis." Angewandte Chemie 135 10 (2022).
 
Trifluoromethanesulfonic anhydride Kev npaj cov khoom thiab cov ntaub ntawv raw
Cov khoom nyoos Phosphorus pentoxide-->Trifluoromethanesulfonic acid-->Benzenesulfonic acid, 4-methyl-, anhydride with trifluoromethanesulfonic acid (9CI)-->bromine trifluoromethanesulfonate-->FLUOROTRIBROMOMETHANE-->TRIFLUOROMETHANESULFONIC ACID TRIFLUOROMETHYL ESTER
Cov khoom npaj (S)-(-)-7,7'-BIS[DI(3,5-DIMETHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE-->(R)-7,7'-BIS(DIPHENYLPHOSPHINO)-1,1'-SPIROBIINDANE-->(R)-(+)-7,7'-BIS(DIPHENYLPHOSPHINO)-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE-->(R)-(+)-7,7'-BIS[DI(4-METHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE-->(S)-7,7'-Bis[di(p-methylphenyl)phosphino]-1,1'-spirobiindane ,97%-->1-FLUORO-4-(TRIFLUOROMETHYLTHIO)BENZENE-->(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL-->(R)-(+)-TolBINAP-->1-(3-AMINO-PYRIDIN-2-YL)-ETHANONE-->(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl-->N-Phenyl-bis(trifluoromethanesulfonimide)-->5-AMINO-1,2,3-THIADIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER-->3,5-DIMETHYLISOXAZOL-4-YL ISOCYANATE-->2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE-->Troglitazone

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