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865-33-8

Basic Information
CAS No.: 865-33-8
Name: Potassium methylate
Molecular Structure:
Molecular Structure of 865-33-8 (Potassium methylate)
Formula: CH3KO
Molecular Weight: 70.13
Synonyms: Methanol,potassium salt (8CI,9CI);Potassium methoxide (6CI,7CI);Feldalat KM;Methoxypotassium;
EINECS: 212-736-1
Density: 0.95 g/mL at 20 °C
Melting Point: -20 °C
Boiling Point: 48.1 °C at 760 mmHg
Flash Point: 11.1 °C
Solubility: may decompose in water
Appearance: solid
Hazard Symbols: FlammableF, ToxicT, CorrosiveC
Risk Codes: 11-14-34-67-65-63-48/20-39/23/24/25-38
Safety: 8-16-26-43-45-62-46-36/37/39-33-29-25
Transport Information: UN 3274 3/PG 2
PSA: 23.06000
LogP: 0.04670
Synthetic route
67-56-1

methanol

100-67-4

potassium phenolate

A

865-33-8

potassium methanolate

B

108-95-2

phenol

Conditions
ConditionsYield
With 1-chloro-2,4-dinitro-benzene at 40℃; Equilibrium constant; Thermodynamic data; further temperatures, ΔH(activ.), ΔG(activ.), ΔS(activ.);
67-56-1

methanol

36294-21-0

potassium 2-naphthoxide

A

865-33-8

potassium methanolate

B

135-19-3

β-naphthol

Conditions
ConditionsYield
With 1-chloro-2,4-dinitro-benzene at 40℃; Equilibrium constant; Thermodynamic data; further temperatures, ΔH(activ.), ΔG(activ.), ΔS(activ.);
67-56-1

methanol

19402-71-2

potassium 1-naphtholate

A

90-15-3

α-naphthol

B

865-33-8

potassium methanolate

Conditions
ConditionsYield
With 1-chloro-2,4-dinitro-benzene at 40℃; Equilibrium constant; Thermodynamic data; further temperatures, ΔH(activ.), ΔG(activ.), ΔS(activ.);

C13H14N3O5(1-)*K(1+)

A

39139-79-2

1-dimethylamino-2,4-dinitronaphthalene

B

865-33-8

potassium methanolate

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant; var. temperatures;

C13H14N3O5(1-)*K(1+)

A

39139-79-2

1-dimethylamino-2,4-dinitronaphthalene

B

865-33-8

potassium methanolate

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant; var. temperatures;

C15H18N3O5(1-)*K(1+)

A

865-33-8

potassium methanolate

B

Diethyl-(3-methoxy-2,4-dinitro-naphthalen-1-yl)-amine

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant;

C15H18N3O5(1-)*K(1+)

A

865-33-8

potassium methanolate

B

Diethyl-(3-methoxy-2,4-dinitro-naphthalen-1-yl)-amine

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant;

C16H20N3O5(1-)*K(1+)

A

865-33-8

potassium methanolate

B

Butyl-(3-methoxy-2,4-dinitro-naphthalen-1-yl)-methyl-amine

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant;

C16H18N3O5(1-)*K(1+)

A

865-33-8

potassium methanolate

B

1-(3-Methoxy-2,4-dinitro-naphthalen-1-yl)-piperidine

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant;

C16H20N3O5(1-)*K(1+)

A

865-33-8

potassium methanolate

B

Butyl-(3-methoxy-2,4-dinitro-naphthalen-1-yl)-methyl-amine

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant;

C16H18N3O5(1-)*K(1+)

A

865-33-8

potassium methanolate

B

1-(3-Methoxy-2,4-dinitro-naphthalen-1-yl)-piperidine

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; Equilibrium constant; Rate constant;

Kalium-4-cyan-2,6-dinitro-1,1-dimethoxy-cyclohexadienid

A

19018-96-3

2,6-dinitro-4-cyanoanisole

B

865-33-8

potassium methanolate

Conditions
ConditionsYield
In methanol at 25℃; Equilibrium constant;

C10H11N2O8(1-)*K(1+)

A

38102-00-0

2-methoxy-3,5-dinitro-benzoic acid methyl ester

B

865-33-8

potassium methanolate

Conditions
ConditionsYield
With (decomposition) In methanol at 25℃; Rate constant; Equilibrium constant;
67-56-1

methanol

865-33-8

potassium methanolate

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; Equilibrium constant; var. of temp., amount of water;
With potassium In Petroleum ether at 60℃; Microwave irradiation; Inert atmosphere;
67-56-1

methanol

K2CO3

K2CO3

865-33-8

potassium methanolate

Conditions
ConditionsYield
at 20℃;
124-41-4

sodium methylate

K2CO3

K2CO3

865-33-8

potassium methanolate

Conditions
ConditionsYield
With methanol at 20℃;
K2CO3

K2CO3

calcium methylate

calcium methylate

865-33-8

potassium methanolate

Conditions
ConditionsYield
With methanol at 20℃;
503-30-0

trimethylene oxide

bis(15-crown-5)potassium potasside

A

74-85-1

ethene

B

865-33-8

potassium methanolate

C

16872-93-8

potassium propylate

D

potassium tetra(ethylene glycoxide) vinyl ether

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; Product distribution; Further Variations:; Temperatures; Decomposition;
67-56-1

methanol

7440-09-7

potassium

865-33-8

potassium methanolate

Conditions
ConditionsYield
In methanol byproducts: H; dissolving of K in CH3OH, violent reactn.;;
In methanol byproducts: H; dissolving of K in CH3OH, violent reactn.;;
In tetrahydrofuran Inert atmosphere; Schlenk technique; Glovebox;
67-56-1

methanol

3K(1+)*H(1+)*MnO(O2)3(4-)=K3H{MnO(O2)3}

A

2K(1+)*2H(1+)*MnO(O2)3(4-)=K2H2{MnO(O2)3}

B

865-33-8

potassium methanolate

Conditions
ConditionsYield
at -20°C;

(2,3-dihydro-2-methyl-1-(trimethylsilyl)-1H-1,3,2-diazaborolyl)potassium

A

129920-28-1

2,3-dihydro-2-methyl-1-(trimethylsilyl)-1H-1,3,2-diazaborole

B

865-33-8

potassium methanolate

Conditions
ConditionsYield
With CH3OH In diethyl ether under N2, -78°C, warmed to room temp.; solvent pumped off, distn.;A 18-23
B n/a
865-33-8

potassium methanolate

350-46-9

4-Fluoronitrobenzene

100-17-4

para-methoxynitrobenzene

Conditions
ConditionsYield
In various solvent(s) at 125℃; for 0.0583333h; microwave irradiation;100%

[Cp2Nb2](η(10),μ-C10H8)(μ-Cl)(μ-H)

865-33-8

potassium methanolate

(C5H4)2Nb2(C5H5)2(H)(OCH3)

Conditions
ConditionsYield
In toluene equimolar amts. of Nb complex and CH3OK heated in toluene at 100°C in standard Schlenk-type app. for 5 h; evapd. in vacuo, extd. (hot hexane), crystd. from hexane;100%
In toluene (evacuated system); mixt. heated at 100°C for 1 h; evapd. solvent; extd. (hexane); elem. anal.;90%
In toluene inert atmosphere; 100°C, 5 h; solvent removal, extn. (ether), evapn.; elem. anal.;>99
146948-51-8

3-fluoro-2-methyl-6-nitro-benzoic acid

865-33-8

potassium methanolate

881415-49-2

3-Methoxy-2-methyl-6-nitro-benzoic acid

Conditions
ConditionsYield
Stage #1: 3-fluoro-2-methyl-6-nitro-benzoic acid; potassium methanolate In tetrahydrofuran; methanol at 100℃; for 2h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; methanol
100%
67-56-1

methanol

1067892-75-4

2-methylthio-4-(morpholin-4-yl)-6-phenylethynyl-pyrimidine-5-carbaldehyde

865-33-8

potassium methanolate

1067892-94-7

(7Z)-7-benzylidene-5-methoxy-2-methylthio-4-(morpholin-4-yl)-5,7-dihydrofuro[3,4-d]pyrimidine

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 0.0833333h; Microwave irradiation; regioselective reaction;100%
456-47-3

3-fluoro-benzenemethanol

865-33-8

potassium methanolate

455-68-5

methyl 3-fluorobenzoate

Conditions
ConditionsYield
With tellurium; bismuth (III) nitrate pentahydrate; 5%-palladium/activated carbon; oxygen In methanol at 60℃; under 760.051 Torr; for 8h;100%
865-33-8

potassium methanolate

73183-34-3

bis(pinacol)diborane

C13H27B2O5(1-)*K(1+)

Conditions
ConditionsYield
In methanol Schlenk technique;100%
67-56-1

methanol

50-00-0

formaldehyd

865-33-8

potassium methanolate

122555-91-3

1,4,7-tris-tert-butoxycarbonylmethyl-1,4,7,10-tetraazacyclododecane

tri-tert-butyl ester 10-methoxymethyl-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid

Conditions
ConditionsYield
at 20℃; for 80h; Product distribution / selectivity;99.6%
1843-42-1

2-(β-hydroxyethylthio)1,3,2-oxathiastibolane

865-33-8

potassium methanolate

130429-33-3

2-(β-hydroxyethylthio)1,3,2-oxathiastibolane(K)

Conditions
ConditionsYield
In methanol A soln. of KOMe is added to a suspn. of the Sb-compd., mixt. is refluxed for about 1 h.; Excess CH3OH is removed under vac., product is washed with CH2Cl2, elem. anal.;99.56%

{HO(CH2)2S(CH2)2O}Sb{O(CH2)2S(CH2)2O}

865-33-8

potassium methanolate

K(1+)*Sb{O(CH2)2S(CH2)2O}2(1-)=KSb{O(CH2)2S(CH2)2O}2

Conditions
ConditionsYield
In methanol anhydrous conditions; molar ratio 1 : 1, refluxing (1 h); solvent removal (reduced pressure, pptn.), recrystn. (DMSO/benzene); elem. anal.;99%
860393-33-5

H{Sb(OC(CH3)2C(CH3)2O)2}

865-33-8

potassium methanolate

K(1+)*Sb(OC(CH3)2C(CH3)2O)2(1-) = K{Sb(OC(CH3)2C(CH3)2O)2}

Conditions
ConditionsYield
In methanol anhyd. conditions, molar ratio 1:1, refluxed 1 h; solvent removed in vac., recrystd. (DMSO/dichlorometane); elem. anal., mol.wt. detn.;99%

Cl2Sn{Nb(OC3H7)6}2

865-33-8

potassium methanolate

(CH3O)2Sn{Nb(OC3H7)6}2

Conditions
ConditionsYield
In benzene byproducts: KCl; rigorously anhydrous conditions; stoichiometric amounts;; elem. anal.;;99%

N1,N4-bis-(Z-Trp)benzene-1,4-diamine

865-33-8

potassium methanolate

C32H32N6O6

Conditions
ConditionsYield
In methanol at 15℃; for 0.0833333h;99%

5-bromo-6-fluoro-N,N-dimethylpyridin-2-amine

865-33-8

potassium methanolate

5-bromo-6-methoxy-N,N-dimethylpyridin-2-amine

Conditions
ConditionsYield
In methanol at 71℃; for 2.16667h; Large scale;99%
In methanol for 2.5h; Reflux;95%
865-33-8

potassium methanolate

1-methyl-2-(3-(trifluoromethyl)but-3-en-1-yn-1-yl)benzene

1-methyl-2-(3-(trimethoxymethyl)but-3-en-1-yn-1-yl)benzene

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 18h; Inert atmosphere; Schlenk technique; chemoselective reaction;99%
865-33-8

potassium methanolate

1,2-dimethyl-3-(3-(trifluoromethyl)but-3-en-1-yn-1-yl)benzene

1,2-dimethyl-3-(3-(trimethoxymethyl)but-3-en-1-yn-1-yl)benzene

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 18h; Inert atmosphere; Schlenk technique; chemoselective reaction;99%
865-33-8

potassium methanolate

(3-(trifluoromethyl)but-3-en-1-yn-1-yl)benzene

(4,4-dimethoxy-3-(methoxymethyl)but-3-en-1-yn-1-yl)benzene

Conditions
ConditionsYield
Stage #1: potassium methanolate In 1,2-dimethoxyethane at -10℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: (3-(trifluoromethyl)but-3-en-1-yn-1-yl)benzene In 1,2-dimethoxyethane at -10℃; for 22h; Inert atmosphere; Schlenk technique;
99%
865-33-8

potassium methanolate

1-chloro-2-(3-(trifluoromethyl)but-3-en-1-yn-1-yl)benzene

1-chloro-2-(3-(trimethoxymethyl)but-3-en-1-yn-1-yl)benzene

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 18h; Inert atmosphere; Schlenk technique; chemoselective reaction;99%
865-33-8

potassium methanolate

C12H9F3O

1-methoxy-2-(3-(trimethoxymethyl)but-3-en-1-yn-1-yl)benzene

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 18h; Inert atmosphere; Schlenk technique; chemoselective reaction;99%
1589544-77-3

1-methoxy-4-(3-(trifluoromethyl)but-3-en-1-yn-1-yl)benzene

865-33-8

potassium methanolate

1-methoxy-4-(3-(trimethoxymethyl)but-3-en-1-yn-1-yl)benzene

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 18h; Inert atmosphere; Schlenk technique; chemoselective reaction;99%
1589544-78-4

1-chloro-4-(3-(trifluoromethyl)but-3-en-1-yn-1-yl)benzene

865-33-8

potassium methanolate

1-chloro-4-(3-(trimethoxymethyl)but-3-en-1-yn-1-yl)benzene

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 18h; Inert atmosphere; Schlenk technique; chemoselective reaction;99%
865-33-8

potassium methanolate

4-(3-(trifluoromethyl)but-3-en-1-yn-1-yl)-1,1'-biphenyl

4-(3-(trimethoxymethyl)but-3-en-1-yn-1-yl)-1,1'-biphenyl

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 18h; Inert atmosphere; Schlenk technique; chemoselective reaction;99%
1589544-87-5

1-(3-(trifluoromethyl)but-3-en-1-yn-1-yl)naphthalene

865-33-8

potassium methanolate

1-(3-(trimethoxymethyl)but-3-en-1-yn-1-yl)naphthalene

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 18h; Inert atmosphere; Schlenk technique; chemoselective reaction;99%
865-33-8

potassium methanolate

126248-77-9

bis(2,2-dimethylpropanoic) selenoanhydride

127678-35-7

potassium 1,1-dimethylethanecarboselenoate

Conditions
ConditionsYield
In diethyl ether; hexane at 0℃; for 3h;98%

{HO(CH2)2O(CH2)2O}Sb{O(CH2)2O(CH2)2O}

865-33-8

potassium methanolate

K(1+)*Sb{O(CH2)2O(CH2)2O}2(1-)=KSb{O(CH2)2O(CH2)2O}2

Conditions
ConditionsYield
In methanol anhydrous conditions; molar ratio 1 : 1, refluxing (1 h); solvent removal (reduced pressure, pptn.), recrystn. (DMSO/benzene); elem. anal.;98%

H(1+)*(CH3COCHCOCH3)2Al(OC(CH3)2C(CH3)2O)(1-)=H[(CH3COCHCOCH3)2Al(OC(CH3)2C(CH3)2O)]

865-33-8

potassium methanolate

CH3OHK(1+)*(CH3COCHCOCH3)2Al(OC(CH3)2C(CH3)2O)(1-)=CH3OHK[(CH3COCHCOCH3)2Al(OC(CH3)2C(CH3)2O)]

Conditions
ConditionsYield
In methanol Al-compd.:alkali-compd. molar ratio was 1:1, alcoholate-compd. in MeOH was added to MeOH suspn. of Al-compd., reflux for 1.5 h; MeOH was removed in vac., recrystn. from DMSO:CH2Cl2 (6:1), elem. anal.;98%

H(1+)*(CH3COCHCOCH3)2Al(OC(CH3)2CH2CH(CH3)O)(1-)=H[(CH3COCHCOCH3)2Al(OC(CH3)2CH2CH(CH3)O)]

865-33-8

potassium methanolate

CH3OHK(1+)*(CH3COCHCOCH3)2Al(OC(CH3)2C(CH3)2O)(1-)=CH3OHK[(CH3COCHCOCH3)2Al(OC(CH3)2C(CH3)2O)]

Conditions
ConditionsYield
In methanol Al-compd.:alkali-compd. molar ratio was 1:1, alcoholate-compd. in MeOH was added to MeOH suspn. of Al-compd., reflux for 1.5 h; MeOH was removed in vac., recrystn. from DMSO:CH2Cl2 (6:1), elem. anal.;98%

C40H89CeClO13Si3

865-33-8

potassium methanolate

C45H100CeO15Si3

Conditions
ConditionsYield
In diethyl ether at 20℃;98%
865-33-8

potassium methanolate

(3-(trifluoromethyl)but-3-en-1-yn-1-yl)benzene

(3-(trimethoxymethyl)but-3-en-1-yn-1-yl)benzene

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 18h; Temperature; Inert atmosphere; Schlenk technique; chemoselective reaction;98%
21505-24-8

hexachlorotropone

865-33-8

potassium methanolate

51877-62-4

Pentachlorbenzoesaeure-methylester

Conditions
ConditionsYield
In toluene at 0℃; for 2h;97%
865-33-8

potassium methanolate

germanium dioxide

120-80-9

benzene-1,2-diol

112712-64-8

tris(1,2-benzenediolato-O,O′)germanate

Conditions
ConditionsYield
With 2,3-butanediol In methanol (N2); added a soln. of CH3OK and than a soln. of catechol and 2,3-butanediol to suspn. of GeO2; refluxed for 2 h; evapd.; washed with ether; dried in vacuo; IR;97%
In methanol soln. of MeOK is added to suspension of GeO2 under N2, soln. of catechol is added at room temp., mixt. is stirred and heated under reflux for 72 h; evapn., washing (ether);95%
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Chemistry

IUPAC Name: Potassium methanolate
Synonyms of Potassium methylate (CAS NO.865-33-8): Methanol, potassium salt ; Methanol, potassium salt (1:1) ; Potassium methanolate
CAS NO: 865-33-8
Molecular Formula: CH3KO
Molecular Weight : 70.1322
Molecular Structure:
EINECS: 212-736-1
H bond acceptors: 1
H bond donors: 1
Density: 0.95 g/mL at 20 °C
Freely Rotating Bonds: 0
Polar Surface Area: 20.23 Å2
Flash Point: 11.1 °C
Enthalpy of Vaporization: 35.21 kJ/mol
Boiling Point: 48.1 °C at 760 mmHg
Vapour Pressure: 265 mmHg at 25°C
Melting Point: -20°C
Storage temp: Flammables area
Water Solubility: may decompose
Sensitive: Moisture Sensitive
Form: Potassium methylate (CAS NO.865-33-8) is solid.
Stability: Stable. Reacts violently with water. Moisture sensitive. Absorbs carbon dioxide from the air. Incompatible with acids, strong oxidizing agents, acid chlorides, acid anhydrides, alkali metals.

Uses

 Potassium methylate (CAS NO.865-33-8) is used as a condensing agent, a catalyst for production of Methyl formate, alkaline catalyst for Dimethyl formamide.It can also be used as pharmaceutical raw material.

Safety Profile

Hazard Codes: FlammableF,ToxicT,CorrosiveC
Risk Statements: 11-14-34-67-65-63-48/20-39/23/24/25-38
R11: Highly flammable. 
R14 : Reacts violently with water.
R34: Causes burns.
R38: Irritating to skin.
R63: Possible risk of harm to the unborn child. 
R65: Harmful: may cause lung damage if swallowed. 
R67: Vapours may cause drowsiness and dizziness.
R39/23/24/25: Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed 
R48/20: Harmful: danger of serious damage to health by prolonged exposure through inhalation
Safety Statements: 8-16-26-43-45-62-46-36/37/39-33-29-25
S8: eep container dry. 
S16: Keep away from sources of ignition. 
S25: Avoid contact with eyes. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S29: Do not empty into drains. 
S33: Take precautionary measures against static discharges. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.  
S43: In case of fire use ... (there follows the type of fire-fighting equipment to be used.) 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S46: If swallowed, seek medical advice immediately and show this container or label. 
S62: If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label.
RIDADR: UN 3274 3/PG 2
WGK Germany: 1
F: 3-10-23
TSCA: Yes
HazardClass: 4.2
PackingGroup: II
HS Code: 29051900
Ignites in moist air. When heated to decomposition it emits toxic fumes of K2O.