546-89-4

Basic information

• Product Name: Lithium acetate
• Synonyms: LITHIUM ACETATE;LITHIUM ACETATE PHIX(R) BUFFER;ACETIC ACID LITHIUM SALT;Lithiumacetat;lithiumethanate;Lithiumethanoat;lithiumethanoate;quilone
• CAS NO: 546-89-4
• Molecular Formula: C₂H₃LiO₂
• Molecular Weight: 65.99
• EINECS: 208-914-3
• Product Categories: Organic-metal salt;LITHIUM COMPOUNDS;Classes of Metal Compounds;Li (Lithium) Compounds;Typical Metal Compounds;LithiumMicro/Nanoelectronics;Inorganic Salts;Lithium;Solution Deposition Precursors;Synthetic Reagents
• Mol File: 546-89-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 283-285 °C(lit.)
• Boiling Point: 117.1 °C at 760 mmHg
• Flash Point: 40 °C
• Appearance: White to yellow/Powder or Crystals
• Density: 1.3[at 20℃]
• Vapor Pressure: 13.9mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: H2O: 5 M at 20 °C, clear, colorless
• Water Solubility: 40.8 g/100 mL (20 ºC)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,5521
• CAS DataBase Reference: Lithium acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Lithium acetate(546-89-4)
• EPA Substance Registry System: Lithium acetate(546-89-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 23-24/25-39-26-22
• WGK Germany: 1
• RTECS: AI5450000
• TSCA: Yes
• Hazardous Substances Data: 546-89-4(Hazardous Substances Data)

Usage

Description

Lithium acetate (CH3COOLi) is a salt of lithium and acetic acid.

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 546-89-4 differently. You can refer to the following data:
1. Lithium acetate is used in the laboratory as buffer for gel electrophoresis of DNA and RNA. It has a lower electrical conductivity and can be run at higher speeds than can gels made from TAE buffer (5-30V/cm as compared to 5 - 10 V / cm). Lithium boric acid or sodium boric acid are usually preferable to lithium acetate or TAE when analyzing smaller fragments of DNA (less than 500 bp) due to the higher resolution of borate-based buffers in this size range as compared to acetate buffers. Lithium acetate is also used to permeabilize the cell wall of yeast for use in DNA transformation. It is believed that the beneficial effect of LiAc is caused by its chaotropic effect denaturing both DNA, RNA and proteins.
2. Lithium acetate hydrate is used in the laboratory as buffer for gel electrophoresis of DNA and RNA. It is also used to permeabilize the cell wall of yeast for use in DNA transformation. It is a metal acetate for proteomics research.
3. Lithium acetate (LiOAc) is a lithium source and a doping salt which can be used in the preparation of plasticized polymer electrolytes for lithium-ion batteries. It can be used as a monovalent cation, which improves the transformation efficiency of Saccharomyces cerevisiae.

Definition

ChEBI: An acetate salt comprising equal numbers of acetate and lithium ions.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALUMINUM and LITHIUM COMPOUNDS.

InChI:InChI=1/C2H4O2.Li/c1-2(3)4;/h1H3,(H,3,4);/q;+1/p-1

Synthetic route

lithium pentafluorobenzenesulfinate (36649-96-4) + mercury(II) diacetate (1600-27-7) → C6F5HgO(O)CCH3 (17314-19-1) + lithium acetate (546-89-4)

Conditions	Yield
In water in aq. suspension at 25°C, molar ratio of LiOS(O)C6F5 and Hg comp. = 1.0:2.1, immediately react.;	A 55% B n/a
In water in aq. suspension at 25°C, molar ratio of LiOS(O)C6F5 and Hg comp. = 1.0:2.1, immediately react.;	A 55% B n/a

lithium tert-butyl hydroperoxide (14680-31-0) + acetone (67-64-1) → formaldehyd (50-00-0) + lithium formate (556-63-8) + lithium acetate (546-89-4) + tert-butyl alcohol (75-65-0)

Conditions	Yield
lithium tert-butoxide In n-heptane at 40℃; Rate constant; Kinetics; other solvents and inhibitors investigated; Energy of activation, A-factor;;

lithium tert-butyl hydroperoxide (14680-31-0) → lithium formate (556-63-8) + lithium acetate (546-89-4) + lithium tert-butoxide (1907-33-1) + tert-butyl alcohol (75-65-0) + LiOH

Conditions	Yield
In various solvent(s) at 80℃; for 8h; Yield given. Yields of byproduct given;
In toluene; cyclohexene at 85℃; for 5h; Kinetics; Product distribution; other solvent, other temperature, other time;
In toluene; cyclohexene at 85℃; for 5h; Yield given. Yields of byproduct given;

n-butyllithium (109-72-8, 29786-93-4) + [bis(acetoxy)iodo]benzene (3240-34-4) → 1-iodo-butane (542-69-8) + iodobenzene (591-50-4) + octane (111-65-9) + n-hexan-2-one (591-78-6) + lithium acetate (546-89-4) + benzene (71-43-2) + LiI

Conditions	Yield
In tetrahydrofuran at -5℃; for 0.0833333h; Product distribution; Mechanism; various amounts of nBuLi, other iodine compounds, various organolithium reagents;

...Expand

2C4H9O2(1-)*C4H9O(1-)*3Li(1+) → lithium formate (556-63-8) + lithium acetate (546-89-4) + lithium tert-butoxide (1907-33-1) + tert-butyl alcohol (75-65-0) + LiOH

Conditions	Yield
1-amino-naphthalene In n-heptane at 80℃; Thermodynamic data; Rate constant; other temperature, other solvent, reaction energy, activation entropy, activation enthalpy, gibbs function;

lithium nitrate + silver(I) acetate (563-63-3) → lithium acetate (546-89-4) + silver nitrate

Conditions	Yield
In acetic acid equilibrium in glacial acetic acid;;

lithium acetate dihydrate (6108-17-4, 61013-21-6, 61013-23-8, 67299-15-4, 116277-84-0) → lithium acetate (546-89-4)

Conditions	Yield
In solid heating at 50-195°C;
In neat (no solvent, solid phase) 110-180°C; XRD;

lithium (7439-93-2) + acetic acid (64-19-7) → lithium acetate (546-89-4)

Conditions	Yield
In neat (no solvent) Ar;

Li(UO2Acet3)*2H2O → uranyl diacetate (17442-23-8, 541-09-3) + lithium acetate (546-89-4)

Conditions	Yield
In neat (no solvent) thermolysis in the absence of O2;

4-nitrophenol acetate (830-03-5) → 4-nitro-phenol (100-02-7) + lithium acetate (546-89-4)

Conditions	Yield
With perchloric acid; water; lithium perchlorate; 2-amino-2-hydroxymethyl-1,3-propanediol pH=7.3 - 8.9; Activation energy; Kinetics; Mechanism; Temperature;

1,2-propylene cyclic carbonate (108-32-7) → lithium propylene-dicarbonate + lithium formate (556-63-8) + lithium acetate (546-89-4)

Conditions	Yield
With lithium hexafluorophosphate; oxygen Electrochemical reaction;

lithium nitrate + acetic acid (64-19-7) → lithium acetate (546-89-4)

Conditions	Yield
In N,N-dimethyl-formamide at 125℃; for 120h; Inert atmosphere;	5.2 g

lithium acetate (546-89-4) + 3,3-dimethyl-allyl chloride (503-60-6) → 3-methylbut-2-enyl acetate (1191-16-8)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In water at 55℃; for 6h; Temperature;	94.15%

scandium(III) nitrate hydrate + hudrochloranilic acid (38689-22-4) + tetraethylammonium bromide (71-91-0) + lithium acetate (546-89-4) + acetone (67-64-1) → (Me4N)[ScIIIcan2].(CH3)2CO

Conditions	Yield
In water	94%

4‐bromobutylferrocene (129826-46-6) + lithium acetate (546-89-4) → 4-ferrocenylbutyl acetate

Conditions	Yield
With bis[2-(2-methoxyethoxy)ethyl] 4-oxo-4H-pyran-2,6-dicarboxylate In acetonitrile at 80℃; for 24h; Reagent/catalyst;	94%

9,10-Dihydrobenzopyrene (66788-01-0) + lithium acetate (546-89-4) → (+/-)-trans-9-acetoxy-10-bromo-9,10,11,12-tetrahydrobenzopyrene (120624-77-3, 120708-42-1)

Conditions	Yield
With N-bromoacetamide In acetic acid for 1.5h; Ambient temperature;	92%

tetra-μ-formiato-diruthenium(II,II) + lithium acetate (546-89-4) → tetra-μ-acetato-diruthenium(II,II)-bis(tetrahydrofuran) (95012-61-6)

Conditions	Yield
In methanol Ru-salt was heated under reflux for 20 min in MeOH contg. Li(O2CMe) under Ar; the soln. was cooled to ambient temp., filtered off, recrystd. from THF at -20°C;	92%

lithium acetate (546-89-4) + cyclohexa-1,3-diene (1165952-91-9) → cis-1-acetoxy-4-chlorocyclohex-2-ene (82736-39-8)

Conditions	Yield
With p-benzoquinone; lithium chloride; palladium diacetate In water; acetic acid Ambient temperature;	89%
With palladium diacetate; p-benzoquinone; lithium chloride In acetic acid at 20℃; for 5h; diastereoselective reaction;	18.7 g

lithium acetate (546-89-4) + 1,4-but-2-ynoic acid benzyl ester (59040-31-2) → benzyl 3-acetoxy-2(Z)-2-d-butenoate

Conditions	Yield
With acetic acid-d; palladium diacetate for 14h; Ambient temperature;	87%

dibenzo-18-crown-6 (14187-32-7) + lithium acetate (546-89-4) → 1,1'-(6,7,9,10,17,18,20,21-octahydrodibenzo[b,k]-[1,4,7,10,13,16]hexaoxacyclooctadecine-2,13-diyl)diethanone (67722-66-1)

Conditions	Yield
With PPA at 68 - 72℃; for 2h;	86%

1,2-Dihydroacridine (16880-79-8) + lithium acetate (546-89-4) → trans-4-Acetoxy-3-bromo-1,2,3,4-tetrahydroacridine

Conditions	Yield
With N-bromoacetamide In acetic acid for 4h; Ambient temperature;	85%

lithium acetate (546-89-4) + 5,6-dihydro-naphthalene-2-carboxylic acid (151623-58-4) → 8-Acetyl-7-bromo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (1026061-78-8)

Conditions	Yield
With N-bromoacetamide In acetic acid for 3h; Ambient temperature;	85%

lithium acetate (546-89-4) + O6-<2-(4-nitrophenyl)ethyl>-9-<3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-O-<(trifluoromethyl)sulfonyl>-β-D-ribofuranosyl>guanine (158604-47-8) → 9-<2'-O-acetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl>-O6-<2-(4-nitrophenyl)ethyl>guanine

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide In N,N-dimethyl-formamide Ambient temperature;	85%

lithium acetate (546-89-4) + cyclohexa-1,3-diene (1165952-91-9) → trans-(±)-4-(acetoxy)cyclohex-2-en-1-yl acetate (78776-44-0, 20117-77-5, 78776-45-1, 135615-69-9)

Conditions	Yield
With oxygen; palladium diacetate; iron(II) phthalocyanine; 2-(phenylsulfinyl)-1,4-benzoquinone In acetic acid under 760 Torr; for 5.5h; Mechanism; Ambient temperature; or 1,4-hydroquinone/DMSO , other benzoquinones, time course of the reaction, stereoselectivity, other diene;	85%
With oxygen; palladium diacetate; iron(II) phthalocyanine; 2-(phenylsulfinyl)-1,4-benzoquinone In acetic acid under 760 Torr; for 5.5h; Ambient temperature;	85%
With manganese(IV) oxide; palladium diacetate; acetic acid; p-benzoquinone In pentane at 25℃; for 72h;	79%

4‐chlorobutylferrocene (141719-29-1) + lithium acetate (546-89-4) → 4-ferrocenylbutyl acetate

Conditions	Yield
With bis[2-(2-methoxyethoxy)ethyl] 4-oxo-4H-pyran-2,6-dicarboxylate In acetonitrile at 80℃; for 24h; Reagent/catalyst;	85%

cyclohepta-3,5-dien-1-ol (1121-63-7) + lithium acetate (546-89-4) → meso-(1R,4R,6R)-3,6-Diacetoxy-4-cyclohepten-1-ol (134780-02-2)

Conditions	Yield
With manganese(IV) oxide; palladium diacetate; p-benzoquinone In acetic acid at 25℃; for 64h;	84%
With manganese(IV) oxide; p-benzoquinone; palladium diacetate In acetic acid for 41h; Ambient temperature;	75%

methyl 2-heptynoate (18937-78-5) + lithium acetate (546-89-4) → methyl 3-acetoxy-2-heptenoate (145733-72-8)

Conditions	Yield
palladium diacetate In acetic acid for 20h; Ambient temperature;	83%
palladium diacetate In acetic acid Product distribution; or sodium, various times; other 2-alkynoic acid derivatives;

lithium acetate (546-89-4) + 7,8-Dihydronaphthalene-2-carboxylic acid (151623-57-3) → 5-Acetyl-6-bromo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (1026640-91-4)

Conditions	Yield
With N-bromoacetamide In acetic acid for 3h; Ambient temperature;	83%

lithium acetate (546-89-4) + phenylpropynoic acid methyl ester (4891-38-7) → (Z)-3-Acetoxy-3-phenyl-acrylic acid methyl ester (145733-73-9)

Conditions	Yield
palladium diacetate In acetic acid for 22h; Ambient temperature;	83%

lithium acetate (546-89-4) + Methyl 2-butynoate (23326-27-4) → β-acetoxy-crotonic acid methyl ester (4525-27-3)

Conditions	Yield
palladium diacetate In acetic acid for 15h; Ambient temperature;	83%

lithium acetate (546-89-4) + 1-Benzyl-3-(2-cyclohexa-2,4-dienyl-ethyl)-urea (125974-32-5) → Acetic acid (3aS,7aS)-1-(toluene-4-sulfonyl)-2,3,3a,4,5,7a-hexahydro-1H-indol-5-yl ester (125974-36-9, 125974-37-0)

Conditions	Yield
With palladium diacetate; p-benzoquinone In acetic acid; acetone for 16h; Ambient temperature;	82%

lithium acetate (546-89-4) + 3,4-Dihydroacridine (37624-10-5) → trans-1-Acetoxy-2-bromo-1,2,3,4-tetrahydroacridine

Conditions	Yield
With N-bromoacetamide In acetic acid for 4h; Ambient temperature;	81%

lithium acetate (546-89-4) + triphenylantimony (603-36-1) → triphenylantimony(V) diacetate (1538-62-1, 34716-94-4)

Conditions	Yield
In acetonitrile Electrolysis; N2 atmosphere, ambient temp.; constant current electrolysis (Pt plate and wire electrodes); extraction (ether), washing of extracts (water, brine), drying (MgSO4),solvent removal, recrystn. (ethanol);	81%

strontium nitrate + plutonium(VI) nitrate + lithium acetate (546-89-4) + water (7732-18-5) → Sr(2+)*PuO2(CH3COO)3(2-)*3H2O=SrPuO2(CH3COO)3*3H2O

Conditions	Yield
With N2H4 In water to Pu-compd. in H2O added with stirring CH3COOLi, N2H4 and Sr(NO3)2 in H2O, coagulated for ca. 30 min; filtered in vac., washed with cold H2O, dried in an air flow for 3 h, elem. anal.;	80%

lithium acetate (546-89-4) + cyclohexa-1,3-diene (1165952-91-9) → cis-2-cyclohexenyl-1,4-diacetate (78776-45-1)

Conditions	Yield
With manganese(IV) oxide; palladium diacetate; acetic acid; p-benzoquinone; lithium chloride In pentane at 25℃; for 72h;	79%
With palladium diacetate; acetic acid In pentane

lithium acetate (546-89-4) + 1,4-but-2-ynoic acid benzyl ester (59040-31-2) → (Z)-3-Acetoxy-but-2-enoic acid benzyl ester (145733-71-7)

Conditions	Yield
palladium diacetate In acetic acid for 8.5h; Ambient temperature;	78%

3-((ethoxycarbonothioyl)thio)pentyl (tert-butoxycarbonyl)(ethyl)sulfamate + lithium acetate (546-89-4) → 3-((ethoxycarbonothioyl)thio)pentyl acetate

Conditions	Yield
In dimethyl sulfoxide at 40℃; for 18h; Inert atmosphere; Sealed tube;	78%

lithium acetate (546-89-4) + 6-(benzyloxy)-1,3-cycloheptadiene (115522-58-2) → 1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene (115522-57-1, 150338-86-6)

Conditions	Yield
With p-benzoquinone; lithium chloride; palladium diacetate In acetic acid	77%

C16H15N7O10S + lithium acetate (546-89-4) → 9-(2-O-acetyl-β-D-arabinofuranosyl)adenine (65174-95-0)

Conditions	Yield
With (1,4,7,10-tetraoxacyclododecane) In dimethyl sulfoxide for 10h; Reagent/catalyst; Reflux;	77%

methyl 2-heptynoate (18937-78-5) + lithium acetate (546-89-4) → methyl 3-oxoheptanoate (39815-78-6)

Conditions	Yield
palladium diacetate In trifluoroacetic acid for 5h; Ambient temperature;	76%

2-Adamantanone (700-58-3) + lithium acetate (546-89-4) → 2-hydroxy-2-(carboxymethyl)adamantane

Conditions	Yield
Stage #1: lithium acetate With bromobenzene; lithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran at 20℃; Stage #2: 2-Adamantanone In tetrahydrofuran at 20℃; for 2h; Reflux; Stage #3: With sulfuric acid In tetrahydrofuran; water Cooling;	76%

Upstream product

• 14680-31-0 lithium tert-butyl hydroperoxide 
• 109-72-8 n-butyllithium 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 6108-17-4 lithium acetate dihydrate 
• 830-03-5 4-nitrophenol acetate 
• 64-19-7 acetic acid 
• 36649-96-4 lithium pentafluorobenzenesulfinate 
• 1600-27-7 mercury(II) diacetate 
• 7439-93-2 lithium 
• 563-63-3 silver(I) acetate 
• 67-64-1 acetone 
• 108-32-7 1,2-propylene cyclic carbonate 

Downstream Products

• 292638-85-8 acrylic acid methyl ester 
• 4525-27-3 β-acetoxy-crotonic acid methyl ester 
• 74-89-5 methylamine 
• 74-84-0 ethane 
• 74-85-1 ethene 
• 108-24-7 acetic anhydride 
• 67-64-1 acetone 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 55943-38-9 2-acetoxyethyl L-3-(3,4-dihydroxyphenyl)2-methylalaninate 
• 12003-67-7 lithium aluminate 
• 554-13-2 lithium carbonate 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 78776-45-1 cis-2-cyclohexenyl-1,4-diacetate 

Relevant articles and documents

The influence of temperature (20-1000 °C) on binary mixtures of solid solutions of CH3COOLi·2H2O-MgHPO4·3H2O

Thermally induced phase transitions (20-1000 °C) in the substrates and binary mixtures of CH3COOLi·2H2O(1)-MgHPO4·3H2O(11) have been analysed. Changes taking place on dehydration and thermal dissociation of bina

Reactions in the rechargeable lithium-O2 battery with alkyl carbonate electrolytes

The nonaqueous rechargeable lithium-O2 battery containing an alkyl carbonate electrolyte discharges by formation of C3H 6(OCO2Li)2, Li2CO3, HCO2Li, CH3CO2Li, CO2, and H 2O at the cathode, due to electrolyte decomposition. Charging involves oxidation of C3H6(OCO2Li)2, Li2CO3, HCO2Li, CH3CO2Li accompanied by CO2 and H2O evolution. Mechanisms are proposed for the reactions on discharge and charge. The different pathways for discharge and charge are consistent with the widely observed voltage gap in Li-O2 cells. Oxidation of C3H6(OCO 2Li)2 involves terminal carbonate groups leaving behind the OC3H6O moiety that reacts to form a thick gel on the Li anode. Li2CO3, HCO2Li, CH3CO 2Li, and C3H6(OCO2Li)2 accumulate in the cathode on cycling correlating with capacity fading and cell failure. The latter is compounded by continuous consumption of the electrolyte on each discharge.

Solvent effects on ester linkage of 4-nitrophenyl acetate in aqueous and ethanol solutions with imidazole and hydroxide ion as nucleophiles

The reaction of 4-nitrophenyl acetate in aqueous and ethanol solutions with imidazole as a nucleophile has been monitored spectrophotometrically. The second order rate constants of these reactions are 10 times higher in water than in alcoholic solutions. This is attributed to better solvation of the initial state and less solvation of the excited state in the alcohol medium. The entropy of activation in water is more negative indicating the greater structuredness of the excited state in water. In addition to the above, the base hydrolysis reaction of the ester using OH- as a nucleophile in buffered aqueous solutions has been followed spectrophotometrically as a function of pH The observed pseudo first order rate constant obeys the relationship k obs=ko+kOH [OH-] where ko represents the water reactions and the buffer dependent rate constant, and kOH is the rate constant for the OH- catalyzed (specific base) reaction. For both cases, a mechanism involving a tetrahedral intermediate and in which the nucleophile attacks at the electrophillic carbon of the ester C=O is proposed.