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Copper(II) triflate

HCID 3260416
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Basic information

CAS
34946-82-2
Standard SMILES
O=S(=O)(O)C(F)(F)F.[Cu]
InChIKey
GZWXEFRPSWBAGC-UHFFFAOYSA-N
Molecular formula
CHCuF3O3S
Average molar mass
213.63 g/mol
Monoisotopic mass
212.889447

Overview

Copper(II) triflate is a chemical compound of copper. Copper is a chemical element with the symbol Cu and atomic number 29. Copper is an essential elements in plants and animals as it is required for the normal functioning of more than 30 enzymes. It occurs naturally throughout the environment in rocks, soil, water, and air. (L277, L278)

Names & identifiers

Preferred name
Copper(II) triflate
IUPAC
copper;trifluoromethanesulfonic acid
English name
Copper(II) trifluoromethanesulfonate
Molecular formula
C2CuF6O6S2
Molecular weight
361.68

Names & synonyms

RefChem:919023(TRIFLUOROMETHANESULFONYLOXY)CUPRIO TRIFLUOROMETHANESULFONATE34946-82-2Copper(II) triflate(Trifluoromethylsulfonyloxy) copper(I)SCHEMBL1448055AKOS015902570DB-344973CS-0158302Cu(OTf)2CuOTfOTF2
Show more names
copper(II) bis(trifluoromethanesulfonate)COPPER TRIFLATECUPRIC TRIFLUOROMETHANESULFONATECOPPER(II) TRIFLUOROMETHANESULPHONATECopper (Ii) TrifluoromeCOPPER TRIFLUOROMETHANESULFONATE

Database identifiers

CAS
34946-82-2
PubChem CID
3260416

Properties

Computed structural properties

Topological polar surface area
62.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
6
Rotatable bonds
0
Heavy atoms
9
Formal charge
0
Complexity
162

Experimental & physicochemical properties

Chemical ClassesMetals -> Organic Acids, Metal Salts
Physical DescriptionPowder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
300 °C · ≥300 °C
storage temp.
Inert atmosphere,Room Temperature
solubility
Water (Slightly)
form
Powder
color
White to slightly blue or light gray
Water Solubility
Soluble in water.
Sensitive
Hygroscopic
Hydrolytic Sensitivity
6 · 6: forms irreversible hydrate
BRN
4028198 · 4028198
Exposure limits
1 mg/m3NIOSH: · ACGIH: TWA 1 mg/m3NIOSH: IDLH 100 mg/m3; TWA 1 mg/m3
Stability
hygroscopic
InChI
InChI=1S/2CHF3O3S.Cu/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Hazards SummaryCauses burns; Inhalation may cause corrosive injuries to upper respiratory tract; [Sigma-Aldrich MSDS]

Safety & protection

Exposure Control and Personal Protection0.01 [mg/m3], respirable fraction (Cu, inorganic cmpnds)[German Research Foundation (DFG)]
Minimum Risk LevelAcute Oral: 0.01 mg/kg/day (L134) Intermediate Oral: 0.01 mg/kg/day (L134)
Threshold Limit Values (TLV)1.0 [mg/m3], as Cu
Permissible Exposure Limit (PEL)1.0 [mg/m3], as Cu
Immediately Dangerous to Life or Health (IDLH)100.0 [mg/m3], as Cu

Toxicology

Health Effects · 1 item

People must absorb small amounts of copper every day because copper is essential for good health, however, high levels of copper can be harmful. Very-high doses of copper can cause damage to your liver and kidneys, and can even cause death. Copper may induce allergic responses in sensitive individuals. (L278, L279)

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesOral (L277) ; inhalation (L277) ; dermal (L277)
Toxicity Summary · 1 item

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Copper is mainly absorbed through the gastrointestinal tract, but it can also be inhalated and absorbed dermally. It passes through the basolateral membrane, possibly via regulatory copper transporters, and is transported to the liver and kidney bound to serum albumin. The liver is the critical organ for copper homoeostasis. In the liver and other tissues, copper is stored bound to metallothionein, amino acids, and in association with copper-dependent enzymes, then partitioned for excretion through the bile or incorporation into intra- and extracellular proteins. The transport of copper to the peripheral tissues is accomplished through the plasma attached to serum albumin, ceruloplasmin or low-molecular-weight complexes. Copper may induce the production of metallothionein and ceruloplasmin. The membrane-bound copper transporting adenosine triphosphatase (Cu-ATPase) transports copper ions into and out of cells. Physiologically normal levels of copper in the body are held constant by alterations in the rate and amount of copper absorption, compartmental distribution, and excretion. (L277, L279)

Applications · 1 item

UsesCopper(II) trifluoromethanesulfonate is a mild lewis acid. It is used as catalyst which promotes dehydration of alcohols and diols to alkenes at ambient temperatures. It is widely used to generate carbenoid species from -diazo esters and ketones, via in situ reduction to the Cu(I) species. It is also promotes the reaction between diazo esters and imines to give aziridines. It catalyzes syn-selective aldol condensation of (Z)-silyl enol ethers with aldehydes, Friedel-Crafts alkylation, acylation reactions of aromatics and addition of trimethylsilyl cyanide to carbonyl compounds.

Preparation methods

PreparationCopper(II) trifluoromethanesulfonate is prepared from copper(II) carbonate and triflic acid (Trifluoromethanesulfonic Acid) in MeCN.

Upstream & downstream products

Upstream raw materials

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
InChIKey
SBTSVTLGWRLWOD-UHFFFAOYSA-L
SMILES
S(=O)(=O)(O[Cu]OS(=O)(=O)C(F)(F)F)C(F)(F)F
CAS DataBase Reference
34946 · 34946-82-2(CAS DataBase Reference)
UNSPSC Code
12161600 · 12161600
NACRES
22 · NA.22
Symbol(GHS)
5 · GHS05
Signal word
Danger
Hazard statements
318 · H318-H314
Precautionary statements
280 · P280-P305+P351+P338-P310-P260-P264-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501-P260h-P301+P330+P331-P303+P361+P353-P501a
PPE
3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
C,Xi
Risk Statements
34 · 34
Safety Statements
26 · 26-36/37/39-45-27
RIDADR
3261 · UN 3261 8/PG 2
WGK Germany
3 · 3
F
3 · 3-10
Hazard Note
Irritant/Hygroscopic
TSCA
No
HazardClass
8 · 8
PackingGroup
III
HS Code
29049085 · 29049085
Storage Class
11 · 11 - Combustible Solids
Limited Quantities
1 Kg · 1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Excess copper is sequestered within hepatocyte lysosomes, where it is complexed with metallothionein. Copper hepatotoxicity is believed to occur when the lysosomes become saturated and copper accumulates in the nucleus, causing nuclear damage. This damage is possibly a result of oxidative damage, including lipid peroxidation. Copper inhibits the sulfhydryl group enzymes such as glucose-6-phosphate 1-dehydrogenase, glutathione reductase, and paraoxonases, which protect the cell from free oxygen radicals. It also influences gene expression and is a co-factor for oxidative enzymes such as cytochrome C oxidase and lysyl oxidase. In addition, the oxidative stress induced by copper is thought to activate acid sphingomyelinase, which lead to the production of ceramide, an apoptotic signal, as well as cause hemolytic anemia. Copper-induced emesis results from stimulation of the vagus nerve. (L277, T49, A174, L280)

Signs and SymptomsBreathing high levels of copper can cause irritation of the nose and throat. Ingesting high levels of copper can cause nausea, vomiting, diarrhea, headache, dizziness, and respiratory difficulty. (L278, L279)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

F
3-10
PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
No
ridadr
UN 3261 8/PG 2
hs_code
29049085
risk_code
34
Signal word
Danger
Symbol(GHS)
GHS05
hazard_code
C,Xi
hazard_note
Irritant/Hygroscopic
safety_code
26-36/37/39-45-27
hazard_class
8
Storage Class
11 - Combustible Solids
packing_group
III
Hazard statements
H318-H314
Limited Quantities
1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Precautionary statements
P280-P305+P351+P338-P310-P260-P264-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501-P260h-P301+P330+P331-P303+P361+P353-P501a
Cupric oxideTrifluoromethanesulfonic acidSilver trifluoromethanesulfonateCupric hydroxide