13257-51-7

Basic information

• Product Name: Mercuric trifluoroacetate
• Synonyms: TRIFLUOROACETIC ACID MERCURY(II) SALT;BIS(TRIFLUOROACETOXY)MERCURY;MERCURIC TRIFLUOROACETATE;MERCURY BISTRIFLUOROACETATE;MERCURY(II) TRIFLUOROACETATE;Mercuric trifluoroacetate~Trifluoroacetic acid mercury(II) salt;TRIFLUOROACETIC ACID MERCURY II;MERCURY(II) TRIFLUOROACETATE 98+%
• CAS NO: 13257-51-7
• Molecular Formula: C₄F₆HgO₄
• Molecular Weight: 426.62
• EINECS: 236-250-4
• Mol File: 13257-51-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 171-173 °C(lit.)
• Boiling Point: 72.2 °C at 760 mmHg
• Appearance: White/Crystalline
• Vapor Pressure: 96.2mmHg at 25°C
• Storage Temp.: Store below +30°C.
• Water Solubility: soluble
• Sensitive: Hygroscopic
• BRN: 3633860
• CAS DataBase Reference: Mercuric trifluoroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Mercuric trifluoroacetate(13257-51-7)
• EPA Substance Registry System: Mercuric trifluoroacetate(13257-51-7)

Safety Data

• Hazard Codes: T+,N,T
• Statements: 26/27/28-33-50/53-50-28
• Safety Statements: 13-28-36-45-60-61-28A-26-22-20
• RIDADR: UN 2025 6.1/PG 2
• WGK Germany: 3
• F: 3-21
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 13257-51-7(Hazardous Substances Data)

Usage

Chemical Properties

almost white to light beige crystalline powder

Uses

Mercuric Trifluoroacetate can be used to prepare shrinkage-?reducing polycarboxylic acid water reducer for concrete.

Purification Methods

Recrystallise it from trifluoroacetic anhydride/trifluoroacetic acid [Lan & Kochi J Am Chem Soc 108 6720 1986]. [Beilstein 2 IV 458.] It is very TOXIC and hygroscopic.

InChI:InChI=1/C2HF3O2.Hg/c3-2(4,5)1(6)7;/h(H,6,7);

Synthetic route

trifluoroacetic acid (76-05-1) + mercury(II) oxide → mercury(II) trifluoroacetate (13257-51-7)

Conditions	Yield
at 80℃; for 0.5h;	100%
In neat (no solvent) HgO and CF3COOH were heated under reflux, CF3COOH was distilled off at 150°C;

trifluoroacetyl hypobromite (431-45-8) + C2F3O2(1-)*Br(1-)*Hg(2+) → mercury(II) trifluoroacetate (13257-51-7)

Conditions	Yield
In trifluoroacetic acid at 25℃; Equilibrium constant;

Trifluoracetylhypoiodit (359-47-7) + C2F3O2(1-)*Hg(2+)*I(1-) → mercury(II) trifluoroacetate (13257-51-7)

Conditions	Yield
In trifluoroacetic acid at 25℃; Equilibrium constant;

mercury(I) trifluoroacetate → mercury(II) trifluoroacetate (13257-51-7) + mercury(I) chloride

Conditions	Yield
With HCl In trifluoroacetic acid
With HCl In trifluoroacetic acid

mercury(II) trifluoroacetate (13257-51-7) + 2-methyl-4,4,5,5-tetramethyl-1,3-dioxolanium perchlorate → 2,3-dimethyl-2,3-butane diol (76-09-5) + C4H2ClF3Hg2O8

Conditions	Yield
In ethanol for 0.25h; Heating; Yields of byproduct given;	A n/a B 99%

1-[2-(4-bromo-phenyl)-2-oxo-ethyl]-pyridinium betaine (17282-45-0) + mercury(II) trifluoroacetate (13257-51-7) → 1-(2-oxo-2-(4-bromophenyl)-1-trifluoroacetoxymercurioethyl)pyridinium trifluoroacetate (255737-12-3)

Conditions	Yield
In water Hg-compd. addn. to soln. of ylide, after 5 min solvent removing (reducedpressure); residue washing (hexane), drying; elem. anal.;	99%

CH2C5H4NCH2C(O)C6H5 (255737-19-0) + mercury(II) trifluoroacetate (13257-51-7) → 2-methyl-1-[2-(4-nitrophenyl)-2-oxo-1-trifluoroacetoxymercurioethyl]-2-methylpyridinium trifluoroacetate (255737-29-2)

Conditions	Yield
In ethanol Hg-compd. addn. to soln. of ylide; after 10 min solvent removing (reduced pressure), residue washing (diethyl ether, hexane), drying; elem. anal.;	99%

N-4-Nitrophenacyl-pyridinium-ylid (25357-54-4) + mercury(II) trifluoroacetate (13257-51-7) → 1-(2-oxo-2-(4-nitrophenyl)-1-trifluoroacetoxymercurioethyl)pyridinium trifluoroacetate (255737-14-5)

Conditions	Yield
In water Hg-compd. addn. to soln. of ylide, after 0.2 h min solvent removing (reduced pressure); residue washing (hexane), drying; elem. anal.;	99%

CH2C5H4NCH2C(O)C6H4Br (255737-20-3) + mercury(II) trifluoroacetate (13257-51-7) → 4-methyl-1-[2-(4-nitrophenyl)-2-oxo-1-trifluoroacetoxymercurioethyl]-2-methylpyridinium trifluoroacetate (255737-31-6)

Conditions	Yield
In ethanol Hg-compd. addn. to soln. of ylide; after 0.2 h solvent removing (reduced pressure), residue washing, hexane), drying; elem. anal.;	99%

4-nitrophenacylpyridinium bromide (25407-30-1) + mercury(II) trifluoroacetate (13257-51-7) → 1-(2-oxo-2-(4-nitrophenyl)-1-trifluoroacetoxymercurioethyl)pyridinium bromide (255737-10-1)

Conditions	Yield
In ethanol byproducts: CF3COOH; refluxing (1 h); solvent removing (reduced pressure, room temperature), residue washing (diethyl ether, hexane), drying; elem. anal.;	99%

mercury(II) trifluoroacetate (13257-51-7) + (4'-nitrophenacyl)triphenylphosphonium bromide (17730-93-7) → [(4-NO2C6H4C(O))(trifluoroacetatomercurio)methyl]triphenylphosphonium bromide

Conditions	Yield
In ethanol adding equimol. amt. of mercury(II) trifluoroacetate to a soln. of organic bromide in anhyd. ethanol, refluxing for 1 h; addn. of diethyl ether, pptn. at 5-6°C over 15 h, filtration, washing the ppt. with hexane, drying; elem. anal.;	99%

mercury(II) trifluoroacetate (13257-51-7) + (2-oxo-2-p-bromophenylethyl)triphenylphosphonium bromide (2928-58-7) → [(4-BrC6H4C(O))(trifluoroacetatomercurio)methyl]triphenylphosphonium bromide (765314-94-1)

Conditions	Yield
In ethanol adding equimol. amt. of mercury(II) trifluoroacetate to a soln. of organic bromide in anhyd. ethanol, refluxing for 1 h; addn. of diethyl ether, pptn. at 5-6°C over 15 h, filtration, washing the ppt. with hexane, drying; elem. anal.;	99%

mercury(II) trifluoroacetate (13257-51-7) + 4-hydroxy-3-(3-methyl-3-butenyl)-2H-1-benzopyran-2-one (104416-40-2) → 2-(chloromercurymethyl)-2-methyl-3,4-dihydro-2H,5H-pyrano<3,2-c><1>benzopyran-5-one (108375-45-7)

Conditions	Yield
With potassium chloride In tetrahydrofuran stirring of coumarin derivative and Hg compd. in THF at room temp. for10 min, addn. of KCl in H2O, 5 min stirred; TLC; extn.(CH2Cl2), dried, evapn. (reduced pressure), addn. (benzene), evapn. (reduced pressure), crystn. (EtOAc);	98%

(CH3(CH2)5)5C6H (219957-94-5) + mercury(II) trifluoroacetate (13257-51-7) → (2,3,4,5,6-pentahexylphenyl)(trifluoroacetato-O)mercury (219957-91-2)

Conditions	Yield
	98%

1-(p-bromophenacyl)pyridinium bromide (17282-37-0) + mercury(II) trifluoroacetate (13257-51-7) → 1-(2-oxo-2-(4-bromophenyl)-1-trifluoroacetoxymercurioethyl)pyridinium bromide (255737-09-8)

Conditions	Yield
In ethanol byproducts: CF3COOH; refluxing (1 h); solvent removing (reduced pressure, room temperature), residue washing (diethyl ether, hexane), drying; elem. anal.;	98%

N,N-dimethylaminomethylferrocene + mercury(II) trifluoroacetate (13257-51-7) → ((CH3)2NCH2C5(HgOCOCF3)4)Fe(C5(HgOCOCF3)5)

Conditions	Yield
In diethyl ether; ethanol addn. of ferrocene deriv. in 1:1 Et2O-EtOH to soln. of Hg(OCOCF3)2 in the same solvent, stirring at room temp. for 90 min; removal of solvent under reduced pressure, washing with water and acetone, drying; elem. anal.;	97%

(2R,3S)-2-{Allyl-[4-(4-fluoro-benzyloxy)-benzenesulfonyl]-amino}-3-hydroxy-butyric acid methyl ester (259132-82-6) + triethyl borane (97-94-9) + mercury(II) trifluoroacetate (13257-51-7) → (2S,3R,6S)-4-[4-(4-Fluoro-benzyloxy)-phenylsulfanyl]-2,6-dimethyl-morpholine-3-carboxylic Acid Methyl Ester

Conditions	Yield
With sodium borohydrid; potassium carbonate In tetrahydrofuran; water	96%

2,2':6,2''-terpyridine (1148-79-4) + mercury(II) trifluoroacetate (13257-51-7) → mercuric trifluoroacetato-2,2':6',2''-terpyridine (140191-74-8)

Conditions	Yield
In ethanol; water addn. of ethanolic soln. of org. ligand to aq. soln. of Hg-salt; pptd. crystals left to stand overnight, filtration off, washing (cold water), drying; elem. anal.;	96%

η,η(5)-fulvalenedimanganesehexacarbonyl + mercury(II) trifluoroacetate (13257-51-7) → octa(trifluoroacetoxymercurio)bicymantrenyl

Conditions	Yield
In dichloromethane inert atmosphere; Hg-compd. addn. to soln. of Mn-compd., stirring (2 h),leaving (overnight); elem. anal.;	96%

1,4-di-tert-butylbenzene (1012-72-2) + mercury(II) trifluoroacetate (13257-51-7) → 1,4-bis[(trifluoroacetoxy)mercurio]-2,5-di-tert-butylbenzene

Conditions	Yield
In melt Ar-atmosphere; stirring (180 - 190°C), alkylbenzene addn., 210°C (20 min); washing (H2O, MeOH), drying (vac.); elem. anal.;	95%

mercury(II) trifluoroacetate (13257-51-7) + (2R,3S)-1-fluoro-3-<(4-methylphenyl)sulphenyl>-6-hepten-2-ol (126887-79-4) → (2R,3S,6R)-6-chloromercuriomethyl-2-fluoromethyl-3{(R)-(4-methylphenyl)sulphenyl}-3,4,5,6-tetrahydro-2H-pyran

Conditions	Yield
With chloride cyclization of corresponding alcohol by Hg(CF3CO2)2 followed by exchange at the acetoxy anion by chloride;	95%

bis(η5-trimethylsilylcyclopentadienyl)bis(trimethylsilylethynyl)-titanium (128247-54-1) + mercury(II) trifluoroacetate (13257-51-7) → (C5H4Si(CH3)3)2Ti(O2CCF3)2 (287934-32-1) + mercury

Conditions	Yield
In tetrahydrofuran byproducts: (CH3)3SiCCCCSi(CH3)3; under N2; addn. of Hg(O2CCF3)2 in THF to Ti complex in THF at 0°C, stirring for 30 min at this temp.; filtration through Celite; removal of volatiles in vac. of oil pump, washing residue with cold n-pentane; elem. anal.;	A 95% B n/a

fc-CH(piperidino)-PO(OC2H5)2 + mercury(II) trifluoroacetate (13257-51-7) → ((C2H5O)2P(O)CH(N(CH2)5)C5(HgOCOCF3)4)Fe(C5(HgOCOCF3)5)

Conditions	Yield
In diethyl ether; ethanol addn. of ferrocene deriv. in 1:1 Et2O-EtOH to soln. of Hg(OCOCF3)2 in the same solvent, stirring at room temp. for 60 min; removal of solvent under reduced pressure, washing with water and acetone, drying; elem. anal.;	95%

sodium perchlorate + mercury(II) trifluoroacetate (13257-51-7) + 1-phenyl-4-(trifluoroacetoxycadmiomethyl)quinolinium trifluoroacetate → 4-(trifluoroacetoxymercuriomethyl)-1-phenylquinolinium perchlorate

Conditions	Yield
In ethanol byproducts: NaOCOCF3; the mixt. of the salts in ethanol was refluxed for 30 min, satd. aq. NaClO4 was added, allowed to stand overnight at 5-6°C; ppt. was filtered off, washed with cold water, dried;	95%

1-trimethylamine-1-carba-closo-dodecaborane (92468-34-3) + mercury(II) trifluoroacetate (13257-51-7) → (CH3)3NCB11(HgOOCCF3)11

Conditions	Yield
With acetic acid In acetonitrile to a soln. of the boron compound in acetonitrile was added a soln. of the Hg salt and CH3COOH in acetonitrile; filtered, washed with water and acetonitrile, dried in air; elem. anal.;	94%

bis(trimethylsilyl)acetylenetitanocene + mercury(II) trifluoroacetate (13257-51-7) → titanocene bis(trifluoroacetate) + mercury

Conditions	Yield
In tetrahydrofuran under Ar atm. soln. Hg(CF3COO)2 in THF was added to soln. Ti complex in THF and stirred at 20°C; soln. was decanted and evapd. to dryness at 20°C, residue was recrystd. from toluene, washed with hexane, and dried in vacuo; elem. anal.;	A 93% B 90%

trimethylphenylammonium closo-dodecaborate + mercury(II) trifluoroacetate (13257-51-7) → 2(CH3)3NC6H5(1+)*B12(HgCF3COO)12(2-)=((CH3)3NC6H5)2B12(HgCF3COO)12 + 2(CH3)3NC6H5(1+)*B12H3(11-)*9Hg(2+)*9CF3COO(1-)=((CH3)3NC6H5)2B12H3(HgCF3COO)9

Conditions	Yield
In water; trifluoroacetic acid addn. of Hg salt soln. to B compd. soln. (mole ratio B12H12(2-):Hg(CF3CO2)2 = 1:12); immediate pptn.; filtration; washing (H2O); drying (air); dissoln. in trifluoroacetic acid; filtration; evapn. of filtrate to dryness; elem. anal.;	A 93% B 5%

[N(PPh3)2]2[Os10C(CO)24] + mercury(II) trifluoroacetate (13257-51-7) → (PPN)2{Os18Hg3C2(CO)42} + (C36H30P2N)(1+)*Os(2+)*3CO*3F3CCO2(1-)=C45H30P2NO9OsF9

Conditions	Yield
In dichloromethane under Ar, exclusion of light, 1.6 equiv. of Hg(O2CCF3)2, 1 h stirring, standing at room temp. for 7 days, at -25°C overnight; ppt. isolated by removal of the liquor, remaining soln. evapd. to dryness, residue extd. twice with CH3OH, recrystd. from CH2Cl2-Et2O to yield a further quantity; elem. anal.;	A 93% B n/a

(η-C5H5)Fe[η-9-(Me2S)-7,8-C2B9H10] + mercury(II) trifluoroacetate (13257-51-7) + sodium chloride (7647-14-5) → 3-(η5-Cp)-4-SMe2-7,8-(CF3COO)2-12-HgCl-3,1,2-FeC2B9H7 + 3-(η5-Cp)-4-SMe2-7,8-(CF3COO)2-9,12-(HgCl)2-3,1,2-FeC2B9H6

Conditions	Yield
In dichloromethane (inert gas); for 2 h at 20°C using 12 equiv. Hg compd.; solvent-removed (vac.), chromd. (SiO2, CH2Cl2/C3H6O) to give 2 fractionswhich were processed separately: stirred with NaCl soln. in H2O, ppt. i solated, washed (H2O), dried (vac.), chromd. (SiO2); elem. anal.;	A 4% B 93%

P-(1,1-dimethylethyl)-P-phenylphosphinoselenoic acid Se-methyl ester (113502-18-4) + mercury(II) trifluoroacetate (13257-51-7) → t-butyl phenyl phosphinic trifluoroacetate (169783-28-2)

Conditions	Yield
In acetonitrile	92%

Upstream product

• 76-05-1 trifluoroacetic acid 
• 12653-71-3 mercury(II) oxide 
• 359-47-7 Trifluoracetylhypoiodit 
• 431-45-8 trifluoroacetyl hypobromite 

Downstream Products

• 104124-51-8 methyl 2-chloromercurio-3-acetoxy-2,3-diphenylcyclopropane-1-carboxylate 
• 104124-50-7 2-chloromercuri-3-trifluoroacetoxy-2,3-diphenylcyclopropane-1-carboxylic methyl ester 
• 41049-47-2 trans-1-iodo-2-trifluoroacetoxycyclohexane 
• 69662-38-0 4-(7-ethoxy-3,7-dimethyl-2-octenyloxy)nitrobenzene 
• 103621-81-4 2,4,6-trineopentylphenylmercury(II) trifluoroacetate 
• 125813-04-9 bis(bis(2,4-dinitrophenyl)selenide) Hg(II)(trifluoroacetate)2 
• 111823-11-1 2-methoxy-2-phenylethylmercury trifluoroacetate 
• 127971-28-2 (Z)-1-(chloromercurio)-2-ethoxy-1,2-diphenylethene 
• 127971-29-3 (Z)-PhC(HgCl)=C(OMe)Ph 
• 96529-95-2 1-chloromercuro-1,3-diphenyl-2-carbomethoxy-3-methoxycyclopropane 
• 102651-41-2 (CO)3Co(HgO₂CCF₃)3*0.5C₆H₅CH₃ 
• 86802-02-0 (C₂H₅)5C₅Mn(CO)2P(C₆H₅)3(Hg(CF₃COO)2) 

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