CAS 358-23-6 Trifluoromethanesulfonic anhydride (HCID 67749)

Overview

Triflic anhydride is an organosulfonic anhydride. It is functionally related to a triflic acid.

Names & identifiers

Preferred name: Trifluoromethanesulfonic anhydride
IUPAC: trifluoromethylsulfonyl trifluoromethanesulfonate
English name: Trifluoromethanesulfonic anhydride
Molecular formula: C2F6O5S2
Molecular weight: 282.14

Names & synonyms

Trifluoromethanesulfonic anhydride358-23-6Triflic anhydrideTrifluoromethanesulphonic anhydride8W034LHG1UTRIFLATE ANHYDRIDEMethanesulfonic acid, 1,1,1-trifluoro-, 1,1'-anhydrideCHEBI:48509DTXSID501014629RefChem:191596DTXCID101437174206-616-8

Show more names

Trifluoromethylsulfonic anhydrideTFO2(trifluoroMethane)sulfonyl trifluoroMethanesulfonateTRIFLUOROMETHANESULFONYL ANHYDRIDE

trifluoromethanesulfonic acid anhydridetrifluoromethylsulfonyl trifluoromethanesulfonateMethanesulfonic acid, trifluoro-, anhydridetrifluoromethanesulphonic acid anhydrideTF2Otrifluoromethanesulfonyl trifluoromethanesulfonateC2F6O5S2triflic acid anhydride

Database identifiers

CAS: 358-23-6
PubChem CID: 67749
DTXSID: DTXSID501014629
ChEBI: CHEBI:48509
UNII: 8W034LHG1U
EC Number: 206-616-8
Nikkaji: J39F

Properties

Computed structural properties

XLogP: 1.6
Topological polar surface area: 94.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 11
Rotatable bonds: 2
Heavy atoms: 15
Formal charge: 0
Complexity: 370

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Acid Anhydrides, Other

PFAS · 2 items

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

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

SpringerMaterials PropertiesSchoenflies notation

Density1.677 @25 °C

Vapor Pressure · 2 items

8.0 [mmHg]

8 [mm Hg] @20 °C

Physical DescriptionColorless hygroscopic liquid; [Merck Index] Clear colorless liquid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point: -80 °C · -80°C
Boiling point: 81 · 81-83 °C (lit.)
Density: 1.677 g/mL · 1.677 g/mL at 25 °C (lit.)
vapor density: 5.2 · 5.2 (vs air)
vapor pressure: 8 mm · 8 mm Hg ( 20 °C)
refractive index: 20 · n20/D 1.321(lit.)
RTECS: 2772000 · PB2772000
Flash point: 81 · 81-83°C
storage temp.: 30 °C · Store below +30°C.
solubility: Miscible with dichloromethane. Immiscible with hydrocarbons.
form: Liquid
Specific Gravity: 1.677 · 1.677
color: Clear colorless to light brown
Water Solubility: reacts violently with water
Sensitive: Moisture Sensitive
BRN: 1813600 · 1813600
Stability: Hygroscopic, Moisture Sensitive
InChI: 1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8
InChIKey: WJKHJLXJJJATHN-UHFFFAOYSA-N
SMILES: FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F
LogP: 0.3 at · 0.3 at 25℃
CAS DataBase Reference: 358 · 358-23-6(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 8 W034LHG1U · 8W034LHG1U
NIST Chemistry Reference: Trifluoromethanesulfonic anhydride(358-23-6)
EPA Substance Registry System: Methanesulfonic acid, trifluoro-, anhydride (358-23-6)
UNSPSC Code: 12352106 · 12352106
NACRES: 22 · NA.22
Symbol(GHS): 3 · GHS03,GHS05,GHS07
Signal word: Danger
Hazard statements: 272 · H272-H302-H314-H335
Precautionary statements: 210 · P210-P220-P280-P301+P312-P303+P361+P353-P305+P351+P338
target organs: Respiratory system
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes: C
Risk Statements: 14 · 14-21/22-34-35-22-40
Safety Statements: 26 · 26-36/37/39-43-45-8
RIDADR: 3265 · UN 3265 8/PG 2
WGK Germany: 3 · 3
F: 10 · 10-21
Hazard Note: Corrosive
TSCA: TSCA listed
HazardClass: 8 · 8
PackingGroup: I
HS Code: 29049020 · 29049020
Storage Class: 5.1 B · 5.1B - Oxidizing hazardous materials
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Dam. 1Ox. Liq. 2Skin Corr. 1BSTOT SE 3
Toxicity: 50 orally · LD50 orally in Rabbit: 1012 mg/kg
REACH Registrations: Active
Limited Quantities: 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H272 (51.1%): May intensify fire; oxidizer [Danger Oxidizing liquids; Oxidizing solids]

P210, P220, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 227 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Methanesulfonic acid, trifluoro-, anhydride

Status: Active Update: 03-04-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/22478

Trifluoromethanesulphonic anhydride: HSNO Approval: HSR004747 Approved with controls

Hazards Summary · 1 item

Reacts violently with water; Corrosive; [Merck Index] Reacts violently with water; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion; [Sigma-Aldrich MSDS] See Trifluoromethanesulfonic acid.

Hazard Classes and CategoriesOx. Liq. 2 (51.1%)

CSL Reaction Information · 6 items

CSL00005

TETRAHYDROFURAN + Triflic anhydride

Can polymerize, large exotherm. Avoid combination on larger scale.

User-Reported

6/29/18

10/2/17

Safety & protection

Protective Action Criteria (PAC) · 3 items

3.0 [mg/m3]

33 [mg/m3]

200 [mg/m3]

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

Safety data

F: 10-21
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: UN 3265 8/PG 2
hs_code: 29049020
Toxicity: LD50 orally in Rabbit: 1012 mg/kg
risk_code: 14-21/22-34-35-22-40
Signal word: Danger
Symbol(GHS): GHS03,GHS05,GHS07
hazard_code: C
hazard_note: Corrosive
safety_code: 26-36/37/39-43-45-8
hazard_class: 8
Storage Class: 5.1B - Oxidizing hazardous materials
packing_group: I
target organs: Respiratory system
Hazard statements: H272-H302-H314-H335
Limited Quantities: 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralEye Dam. 1Ox. Liq. 2Skin Corr. 1BSTOT SE 3
Precautionary statements: P210-P220-P280-P301+P312-P303+P361+P353-P305+P351+P338

Chemistry & industry

Uses & manufacturing

UsesUsed as a reagent in synthetic organic chemistry; [Merck Index]

General Manufacturing InformationMethanesulfonic acid, 1,1,1-trifluoro-, 1,1'-anhydride: ACTIVE

Applications · 3 items

DescriptionTrifluoromethanesulfonic anhydride, also known as triflic anhydride, has proven to be an extraordinary reagent for a broad range of transformations. As a commercially and readily available reagent, It has been widely used in synthetic chemistry due to its high electrophilicity. Given its high affinity towards O-nucleophiles, reaction with alcohols, carbonyls, sulfur phosphorus- and iodine oxides towards the formation of the corresponding triflates is strongly favored. As one of the premier leaving groups in organic chemistry, the generated triflates then open the door to various downstream transformations, including (but not limited to) substitution reactions, cross-coupling processes, redox reactions, and rearrangements[1-2].

UsesTrifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group.

UsesTrifluoromethanesulfonic anhydride is used to convert phenols and imine into triflic ester and NTf group. It is a strong electrophile used for the introduction of triflyl group in chemical synthesis. It serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors. It acts as a catalyst for glycosylation with anomeric hydroxy sugars to prepare polysaccharides.

Upstream & downstream products

Upstream raw materials

Downstream products

5-Amino-1,2,3-thiadiazole-4-carboxylic acid ethyl ester (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl Troglitazone 1-Fluoro-4-(trifluoromethylthio)benzene (S)-(-)-7,7'-Bis[di(3,5-dimethylphenyl)phosphino]-2,2',3,3'-tetrahydro-1,1'-spirobiindane (S)-7,7'-Bis[di(p-methylphenyl)phosphino]-1,1'-spirobiindane ,97%(R)-(+)-7,7'-Bis[di(4-methylphenyl)phosphino]-2,2',3,3'-tetrahydro-1,1'-spirobiindane (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl 3,5-Dimethylisoxazol-4-yl isocyanate (R)-(+)-7,7'-Bis(diphenylphosphino)-2,2',3,3'-tetrahydro-1,1'-spirobiindane N-Phenyl-bis(trifluoromethanesulfonimide)2-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

中船（邯郸）派瑞特种气体股份有限公司021-53930372 13917175395

山东骄阳化工有限公司198 1918 9303/18265196555 18265196555

Additional notes

DefinitionChEBI: Triflic anhydride is an organosulfonic anhydride. It is functionally related to a triflic acid.

Related reactions

2,071 records

New reaction record

HRID 6479As reactantuspto-grants-1993_09

HRID 6486As reactantuspto-grants-1993_09

HRID 7222As reactantuspto-grants-2006_08

HRID 8216As reactantuspto-grants-2006_08

HRID 9117As reactantuspto-grants-2006_08

HRID 14467As reactantuspto-grants-2010_06

HRID 15351As reactantuspto-grants-2010_06

HRID 17265As reactantuspto-grants-2010_06

Compound notes

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Basic information