77-98-5

Basic information

• Product Name: Tetraethylammonium hydroxide
• Synonyms: Ammonium,tetraethyl-, hydroxide (8CI);Ethanaminium, N,N,N-triethyl-, hydroxide (9CI);Tetraethylammonium hydroxide (6CI);Ethanaminium,N,N,N-triethyl-, hydroxide (1:1)
• CAS NO: 77-98-5
• Molecular Formula: C₈H₂₁NO
• Molecular Weight: 147.25844
• EINECS: 201-073-3
• Mol File: 77-98-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 110 °C
• Flash Point: 11 °C
• Appearance: colourless liquid
• Density: 1.023 g/mL at 25 °C
• Water Solubility: SOLUBLE
• CAS DataBase Reference: Tetraethylammonium hydroxide(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraethylammonium hydroxide(77-98-5)
• EPA Substance Registry System: Tetraethylammonium hydroxide(77-98-5)

Safety Data

• Hazard Codes: F:Flammable;;
• Statements: R11:; R23/24/25:; R34:; R39/23/24/25:; R51:
• Safety Statements: S16:; S26:; S36/37/39:; S45:; S61:; S7:
• PackingGroup: II
• Hazardous Substances Data: 77-98-5(Hazardous Substances Data)

Usage

Chemical Description

Tetraethylammonium hydroxide is a strong base used to deprotect the tert-butyl ester group in the synthesis of aza-glycinyl dipeptides.

InChI:InChI=1/C8H20N.H2O/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H2/q+1;/p-1

Synthetic route

diethyl sulfate (64-67-5) + ethanol (64-17-5) + triethylamine (121-44-8) → tetraethylammonium hydroxide (77-98-5)

Conditions	Yield
Stage #1: diethyl sulfate; ethanol; triethylamine In water at 140℃; under 7500.75 Torr; for 4h; Stage #2: With sodium hydroxide In ethanol; water at 45℃; for 4h;	95.7%

tetraethylammonium bromide (71-91-0) → tetraethylammonium hydroxide (77-98-5)

Conditions	Yield
With potassium hydroxide In dichloromethane at 20℃; for 10h;	78%
With potassium hydroxide In ethanol at 20℃; for 10h;
With ion-exchange column Amberlyst A26(OH) In methanol
With Amberlite IRA-400-OH ion-exchange column In methanol

tetraethylammonium chloride (56-34-8) → tetraethylammonium hydroxide (77-98-5)

Conditions	Yield
With methanol; potassium hydroxide durch Zusatz von Wasser und Konzentration unterhalb 50grad unter vermindertem Druck;
With Anion-exchange resin (201 × 7(OH))
With potassium hydroxide In methanol at 20℃; for 2h;

ethyl iodide (75-03-6) + triethylamine (121-44-8) → tetraethylammonium hydroxide (77-98-5)

Conditions	Yield
With water; silver(l) oxide

tetraethylammonium iodide (68-05-3) → tetraethylammonium hydroxide (77-98-5)

Conditions	Yield
With silver(l) oxide In water

Diethyl carbonate (105-58-8) → tetraethylammonium hydroxide (77-98-5) + tetraethylammonium bicarbonate (17351-61-0)

Conditions	Yield
With triethylamine In water

tetraethylammonium hydroxide (77-98-5) + N-(hydroxy)-5-(p-methoxyphenyl)-4-methylthiazole-2(3H)-thione (529477-58-5) → N-(hydroxy)-5-(p-methoxyphenyl)-4-(methyl)thiazole-2(3H)-thione tetraethylammonium salt

Conditions	Yield
In methanol	100%
In methanol at 20℃;

benzene-1,3,5-tricarboxylic acid (554-95-0) + guanidine hydrogen carbonate (124-46-9, 20734-13-8, 100224-74-6, 593-85-1) + tetraethylammonium hydroxide (77-98-5) → C9H3O6(3-)*2C8H20N(1+)*CH5N3*H(1+)

Conditions	Yield
In water for 0.0833333h; Heating;	100%

guanidine hydrogen carbonate (124-46-9, 20734-13-8, 100224-74-6, 593-85-1) + oxalic acid (144-62-7) + tetraethylammonium hydroxide (77-98-5) → 4C8H20N(1+)*3C2O4(2-)*8CH5N3*3CO3(2-)*8H(1+)

Conditions	Yield
In water for 0.0833333h;	100%

diethyl 3,3'-{1,2-phenylenebis[imino(2-methyl-4-oxobutane-4,2-diyl)sulfonyl]}dipropanoate (1015689-87-8) + tetraethylammonium hydroxide (77-98-5) → bis(N,N,N-triethylethanaminium) 4,4'-[1,2-phenylenedi(imino)]bis(2-methyl-4-oxobutane-2-sulfinate)

Conditions	Yield
In methanol; acetonitrile for 0.166667h; retro-Michael reaction;	100%

diethyl 3,3'-{1,2-phenylenebis[imino(2-methyl-4-oxobutane-4,2-diyl)sulfonyl]}dipropanoate (1015689-87-8) + tetraethylammonium hydroxide (77-98-5) → N,N,N-triethylethanaminium 4-{[2-({3-[(3-ethoxy-3-oxopropyl)sulfonyl]-3-methylbutanoyl}amino)phenyl]amino}-2-methyl-4-oxobutane-2-sulfinate

Conditions	Yield
In methanol; acetonitrile for 0.166667h; retro-Michael reaction;	100%

ethyl 3-[(3-{[2-({3-[(3-ethoxy-3-oxopropyl)sulfinyl]-3-methylbutanoyl}amino)phenyl]amino}-1,1-dimethyl-3-oxopropyl)sulfonyl]propanoate (1015689-85-6) + tetraethylammonium hydroxide (77-98-5) → N,N,N-triethylethanaminium 4-{[2-({3-[(3-ethoxy-3-oxopropyl)sulfinyl]-3-methylbutanoyl}amino)phenyl]amino}-2-methyl-4-oxobutane-2-sulfinate

Conditions	Yield
In methanol; acetonitrile for 0.166667h; retro-Michael reaction;	100%

phthalimide (136918-14-4) + tetraethylammonium hydroxide (77-98-5) → tetraethylammonium 2-(carbamoyl)benzoate (1174574-34-5)

Conditions	Yield
In water for 4h; Reflux;	100%
In water for 4h; Reflux;	100%

tetraethylammonium hydroxide (77-98-5) + carbonic acid dimethyl ester (616-38-6) → tetraethylammonium methyl carbonate

Conditions	Yield
In methanol at 20℃; for 15h; Inert atmosphere;	100%

ethanesulfonic acid (594-45-6) + tetraethylammonium hydroxide (77-98-5) → C8H20N(1+)*C2H5O3S(1-)

Conditions	Yield
In methanol Inert atmosphere;	100%

hydrogen hexacyanoferrate(II) + tetraethylammonium hydroxide (77-98-5) → (tetraethylammonium)4 hexacyanoferrate(II)

Conditions	Yield
In water	100%
In water	100%

ibuprofen (15687-27-1) + tetraethylammonium hydroxide (77-98-5) → tetraethylammonium 2-(4-isobutylphenyl)propanoate

Conditions	Yield
In methanol for 1h;	100%

tetraethylammonium hydroxide (77-98-5) + 1-dodecylthiol (112-55-0) → Dodecane-1-thiolatetetraethyl-ammonium; (33081-80-0)

Conditions	Yield
In benzene at 6 - 10℃; for 1h;	99%

1-Amino-2-methoxy-cyclobut-1-ene-3,4-dione (5231-88-9) + tetraethylammonium hydroxide (77-98-5) → tetraethylammonium aminosquarate (212248-45-8)

Conditions	Yield
In water pH < 6.0;	99%

sodium dodecyl-sulfate (151-21-3) + tetraethylammonium hydroxide (77-98-5) → tetraethylammonium dodecyl sulfate (17262-37-2)

Conditions	Yield
In water using a strong cation-exchange resin;	99%
Stage #1: tetraethylammonium hydroxide With Dowex-50 W-X4 (H(+) form) In water Stage #2: sodium dodecyl-sulfate In methanol Further stages.;

tetraethylammonium hydroxide (77-98-5) + pentafluoroethylphosphonic acid (103305-01-7) → bis(tetraethylammonium)pentafluoroethylphosphonate

Conditions	Yield
In water at 20℃;	99%

Benzofuran-2-carboxylic acid (496-41-3) + tetraethylammonium hydroxide (77-98-5) → tetraethylammonium benzofuran-2-carboxylate

Conditions	Yield
In methanol; water at 20℃;	99%

benzo[b]thiophene-2-carboxylic acid (6314-28-9) + tetraethylammonium hydroxide (77-98-5) → tetraethylammonium benzothiophene-2-carboxylate

Conditions	Yield
In methanol; water at 20℃;	99%

C9H9F3N2O3S2*C5H5N + tetraethylammonium hydroxide (77-98-5) → C9H8F3N2O3S2(1-)*C8H20N(1+)

Conditions	Yield
In water Inert atmosphere;	99%

tris(pentafluoroethyl)difluorophosphorane (91543-32-7) + tetraethylammonium hydroxide (77-98-5) → C2HF4O3P(2-)*4C8H20N(1+)*2F(1-) + 1,1,1,2,2-pentafluoroethane (354-33-6)

Conditions	Yield
In water at 20 - 80℃; for 1.5h; Product distribution / selectivity;	A n/a B 98.8%

Octanethiol (111-88-6) + tetraethylammonium hydroxide (77-98-5) → Octane-1-thiolatetetraethyl-ammonium; (138555-15-4)

Conditions	Yield
In benzene at 6 - 10℃; for 1h;	98%

tetraethylammonium hydroxide (77-98-5) + potassium (2-phenylethynyl)trifluoroborate → tetraethylammonium (phenylethynyl)trifluoroborate

Conditions	Yield
In dichloromethane; water for 0.5h;	98%

tetraethylammonium hydroxide (77-98-5) + 3-isobutylamino-1-propanesulfonic acid (1119-70-6) → tetraethylammonium isobutylaminopropanesulfonate

Conditions	Yield
In water for 0.5h;	98%

3-isopropylamino-1-propanesulfonic acid + tetraethylammonium hydroxide (77-98-5) → tetraethylammonium N-isopropyl-N-(3-sulfopropyl)amine (946830-15-5)

Conditions	Yield
In water for 0.5h;	98%

dimethyl(4-sulfonatobutyl)ammonium (89585-26-2) + tetraethylammonium hydroxide (77-98-5) → tetraethylammonium dimethylaminobutanesulfonate

Conditions	Yield
In water for 0.5h;	98%

3-butylamino-propane-1-sulfonic acid (1119-24-0) + tetraethylammonium hydroxide (77-98-5) → tetraethylammonium n-butylaminopropanesulfonate

Conditions	Yield
In water for 0.5h;	98%

C48H47B2Br2N6O9Zn2(1-)*C8H20N(1+) + 3-pyridylboronic acid hydrate + tetraethylammonium hydroxide (77-98-5) → C8H20N(1+)*C58H55B2N8O9Zn2(1-)

Conditions	Yield
Stage #1: C48H47B2Br2N6O9Zn2(1-)*C8H20N(1+); 3-pyridylboronic acid hydrate With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris(dibenzylideneacetone)dipalladium (0) In toluene; butan-1-ol at 120℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; Stage #2: tetraethylammonium hydroxide In methanol; acetonitrile	98%

diethyl ether (60-29-7) + 2,5-diamino-3,6-dibromo-1,4-benzoquinone (27344-26-9) + 3C6Cl2O4(2-)*2Zn(2+)*2C2H7N*2H(1+) + tetraethylammonium hydroxide (77-98-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 1.3C6Cl2O4(2-)*2Zn(2+)*1.7C6H2Br2N2O2(2-)*2C8H20N(1+)*0.57C3H7NO*0.14C4H10O

Conditions	Yield
Stage #1: 3,6-diamino-2,5-dibromo-1,4-benzoquinone; 3C6Cl2O4(2-)*2Zn(2+)*2C2H7N*2H(1+); tetraethylammonium hydroxide; N,N-dimethyl-formamide In water at 75℃; for 48h; Stage #2: diethyl ether	98%

iron(II) triflate + 2,6-diformyl-4-tert-butylphenol dioxime (303994-61-8) + tetraethylammonium hydroxide (77-98-5) + 4-pyridylboronic acid (1692-15-5) → C46H47B2Fe2N8O9(1-)*C8H20N(1+)

Conditions	Yield
Stage #1: iron(II) triflate; 2,6-diformyl-4-tert-butylphenol dioxime; 4-pyridylboronic acid In methanol at 50℃; for 1h; Glovebox; Stage #2: tetraethylammonium hydroxide In methanol; ethanol at 20℃; for 1h;	97%

C9H9F3N2O4S*C5H5N + tetraethylammonium hydroxide (77-98-5) → C9H8F3N2O4S(1-)*C8H20N(1+)

Conditions	Yield
In water Inert atmosphere;	97%

2,5-diamino-3,6-dibromo-1,4-benzoquinone (27344-26-9) + 3C6Cl2O4(2-)*2Mn(2+)*2C2H7N*2H(1+) + tetraethylammonium hydroxide (77-98-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 1.8C6Cl2O4(2-)*2Mn(2+)*1.2C6H2Br2N2O2(2-)*2C8H20N(1+)*0.65C3H7NO

Conditions	Yield
In water at 75℃; for 48h;	97%

Upstream product

• 75-03-6 ethyl iodide 
• 121-44-8 triethylamine 
• 71-91-0 tetraethylammonium bromide 
• 105-58-8 Diethyl carbonate 
• 64-67-5 diethyl sulfate 
• 64-17-5 ethanol 
• 68-05-3 tetraethylammonium iodide 
• 56-34-8 tetraethylammonium chloride 

Downstream Products

• 32580-88-4 tetraethylammonium 2,4-dinitrophenolate 
• 131588-80-2 Tetraethylammonium-1,2,3,4,5-pentakis(phenylthio)cyclopentadienid 
• 131588-82-4 Tetraethylammonium-1,2,3,4,5-pentakis(4-methylphenylthio)cyclopentadienid 
• 3774-76-3 Tentraethylammonium 4-nitrophenoxide 
• 10408-33-0 Tetraethylammonium hydrogen sulfide 
• 64-18-6 formic acid 
• 74-85-1 ethene 
• 121-44-8 triethylamine 
• 1174574-34-5 tetraethylammonium 2-(carbamoyl)benzoate 
• 103533-58-0 [Rh(5,10,15,20-tetraphenylporphyrinato)(ethyl)] 

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