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75-59-2

Basic Information
CAS No.: 75-59-2
Name: Tetramethylammonium hydroxide
Molecular Structure:
Molecular Structure of 75-59-2 (Tetramethylammonium hydroxide)
Formula: C4H13NO
Molecular Weight: 91.18
Synonyms: OPD5262;TMAH;TMAH 25;Tokuso SD 20;Ammonium,tetramethyl-, hydroxide (8CI);Methanaminium, N,N,N-trimethyl-, hydroxide(9CI);Tetramethylammonium hydroxide (6CI);AR 300-49;AZ 300MIF;AZ 726;AZ726MIF;AZ-MIF 300;CD 26;LDD 26;LDD 26W;MF 24A;MF 321;MF-CD 26;MIF 726;Megaposit CD 14;Megaposit MF 24A;Microposit CD 26;Microposit MF 321;Microposit MF-CD 26;NMD 3;NMW-W;OCG 934;OCG 945;OCG-OPD 262;OPD 262;Tetramethyl ammonium hydroxide 75-59-2;
EINECS: 200-882-9
Density: 0.866 g/mL at 25 °C
Melting Point: °C
Boiling Point: 110 °C
Flash Point: 80 °F
Solubility: Soluble in water.
Appearance: colourless to yellow liquid
Hazard Symbols: CorrosiveC,FlammableF,ToxicT
Risk Codes: 24/25-34-20/21/22-39/23/24/25-23/24/25-10-21/22-25-21-11-67-36
Safety: 45-36/37/39-26-16-36/37
Transport Information: UN 3286 3/PG 2
PSA: 23.06000
LogP: 0.14560
Synthetic route
67-56-1

methanol

616-38-6

carbonic acid dimethyl ester

75-50-3

trimethylamine

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
Stage #1: methanol; carbonic acid dimethyl ester; trimethylamine In water at 140℃; under 11251.1 Torr; for 4h;
Stage #2: With calcium hydroxide In methanol; water Heating / reflux;
95.2%
64-20-0

tetramethylammonium bromide

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With potassium hydroxide In dichloromethane at 20℃; for 10h;68%
With water; silver(l) oxide die Salze entstehen; und Eindunsten des Filtrats Vakuum ueber Schwefelsaeure;
With potassium hydroxide In ethanol at 20℃; for 12h;
67-56-1

methanol

598-58-3

methyl nitrate

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With ammonia die Salze entstehen;
75-58-1

tertamethylammonium iodide

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With water Herstellung einer wss. Loesung mit Hilfe eines Anionenaustauschers;
75-57-0

tetramethlyammonium chloride

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With methanol; potassium hydroxide man filtriert vom ausgescheidenen Kaliumchlorid ab und engt unter Zuatz von Wasser im Vakuum bei 35grad ein;
With potassium hydroxide In methanol at 25℃; for 2h;
With sodium hydroxide In ethanol for 4h;
74-83-9

methyl bromide

124-40-3

dimethyl amine

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With methanol at 100℃; die Salze entstehen;
598-58-3

methyl nitrate

124-40-3

dimethyl amine

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With methanol at 100℃; die Salze entstehen;
124-40-3

dimethyl amine

74-88-4

methyl iodide

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With methanol at 100℃; die Salze entstehen;
77-78-1

dimethyl sulfate

75-50-3

trimethylamine

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
Kochen des erhaltenen Methylsulfats mit verd.H2SO4 und anschliessende Umsetzung mit Ba(OH)2;
74-83-9

methyl bromide

74-89-5

methylamine

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With methanol at 100℃; die Salze entstehen;
598-58-3

methyl nitrate

74-89-5

methylamine

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With methanol at 100℃; die Salze entstehen;
74-89-5

methylamine

74-88-4

methyl iodide

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With methanol at 100℃; die Salze entstehen;
74-86-2

acetylene

75-50-3

trimethylamine

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With water at 105℃; unter Druck;
74-83-9

methyl bromide

75-50-3

trimethylamine

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
die Salze entstehen;
74-87-3

methylene chloride

75-50-3

trimethylamine

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
die Salze entstehen;
13448-18-5

trimethyl-vinylammonium cation

75-50-3

trimethylamine

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With water at 110 - 120℃;
74-88-4

methyl iodide

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With ammonia; water die Salze entstehen;
With ethanol; ammonia die Salze entstehen;
58345-96-3

Tetramethylammonium hydrogen carbonate

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With water for 12h; electrolysis (20V);626 g
With hydrogenchloride; formic acid; sulfuric acid In water electrolysis;
tetramethyl-triphenylmethyl-ammonium

tetramethyl-triphenylmethyl-ammonium

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With water
trimethylacetonylammonium bromide

trimethylacetonylammonium bromide

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
at 195 - 200℃; die Salze entstehen;
74-88-4

methyl iodide

trimethylazonium iodide

trimethylazonium iodide

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With methanol at 125 - 130℃; die Salze entstehen;
598-58-3

methyl nitrate

A

75-59-2

tetramethyl ammoniumhydroxide

B

7732-18-5

water

Conditions
ConditionsYield
With ammonia die Salze entstehen; bei laengerem Stehen;
With ammonia die Salze entstehen; beim Erhitzen;
67-56-1

methanol

A

75-59-2

tetramethyl ammoniumhydroxide

B

hydrochloride of trimethylamine

hydrochloride of trimethylamine

Conditions
ConditionsYield
With ammonium chloride at 285℃; die Salze entstehen;

tetramethylammonium sulfate

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With ambersep 900 OH In water Product distribution / selectivity; Alkaline conditions;
In sulfuric acid; water for 6h; Product distribution / selectivity; Electrolysis;

tris(tetramethylammonium) phosphate

75-59-2

tetramethyl ammoniumhydroxide

Conditions
ConditionsYield
With basic anion exchanger In water Product distribution / selectivity;
1569-69-3

Cyclohexanethiol

75-59-2

tetramethyl ammoniumhydroxide

138555-12-1

Cyclohexanethiolatetetramethyl-ammonium;

Conditions
ConditionsYield
In benzene at 6 - 10℃; for 1h;100%
1030850-30-6

bis-p-phenylene-34-crown-10-12,152-dicarboxylic acid

75-59-2

tetramethyl ammoniumhydroxide

bis(tetramethylammonium) bis-p-phenylene-34-crown-10-12,152-dicarboxylate

Conditions
ConditionsYield
In methanol for 2h;100%
3687-18-1

Homotaurin

75-59-2

tetramethyl ammoniumhydroxide

108-24-7

acetic anhydride

1131569-67-9

tetramethylammonium N-acetylhomotaurinate

Conditions
ConditionsYield
Stage #1: Homotaurin; tetramethyl ammoniumhydroxide In water at 20℃; for 1h;
Stage #2: acetic anhydride In water at 40℃;
100%
Stage #1: Homotaurin; tetramethyl ammoniumhydroxide In water at 20℃; for 1h;
Stage #2: acetic anhydride In water at 40℃;
100%
Stage #1: Homotaurin; tetramethyl ammoniumhydroxide In water at 20℃; for 1h;
Stage #2: acetic anhydride In water at 40℃;
100%
1160694-10-9

C29H28N2O7S

75-59-2

tetramethyl ammoniumhydroxide

C4H12N(1+)*C29H27N2O7S(1-)

Conditions
ConditionsYield
In methanol; dichloromethane at -78℃;100%
75-59-2

tetramethyl ammoniumhydroxide

65-85-0

benzoic acid

25255-90-7

tetramethylammonium benzoate

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
In methanol at 45℃; for 4h;75%
In methanol
75-59-2

tetramethyl ammoniumhydroxide

593-85-1

diguanidine carbonate

cis,cis-1,3,5-trimethylcyclohexane-1,3,5-tricarboxylic acid

[(CH3)4N(+)]*2[C(NH2)3(+)]*[KTA(3-)]

Conditions
ConditionsYield
In water at 40℃;100%
78-10-4

tetraethoxy orthosilicate

75-59-2

tetramethyl ammoniumhydroxide

octakis(tetramethylammonium)silsesquioxane

Conditions
ConditionsYield
In methanol; water at 20℃; Cooling with ice; Inert atmosphere;100%
In methanol; water at 20℃; for 24h; Inert atmosphere;97%
In methanol; water at 20℃; for 24h; Cooling with ice;97%
1305346-38-6

C30H24O12

75-59-2

tetramethyl ammoniumhydroxide

107-15-3

ethylenediamine

6C4H12N(1+)*C66H54N6O18(6-)

Conditions
ConditionsYield
With [D]-sodium hydroxide; sodium acetate In water-d2 for 2h; pD >11;100%
2634-33-5

1,2-benzisothiazolin-3-one

75-59-2

tetramethyl ammoniumhydroxide

400089-65-8

tetramethylammonium 1,2-benzisothiazol-3-one

Conditions
ConditionsYield
In water pH=9.58;100%
In water pH=9.0;
75-59-2

tetramethyl ammoniumhydroxide

108-95-2

phenol

36439-44-8

tetramethylammonium phenoxide

Conditions
ConditionsYield
Stage #1: tetramethyl ammoniumhydroxide; phenol In water for 0.0166667h;
Stage #2: at 70℃; for 72h;
100%
In water at 25℃; for 0.166667h;96%
In ethanol; water at 20℃; for 24h; Inert atmosphere;
75-59-2

tetramethyl ammoniumhydroxide

619-84-1

p-N,N-dimethylaminobenzoic acid

70697-58-4

tetramethylammonium 4-(dimethylamino)benzoate

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
In ethanol; water for 1h;
917-71-5

deuterated formic acid

75-59-2

tetramethyl ammoniumhydroxide

C3H6(2)HNO2

Conditions
ConditionsYield
In methanol at 0 - 20℃; for 2h;100%
75-59-2

tetramethyl ammoniumhydroxide

616-38-6

carbonic acid dimethyl ester

tetramethylammonium methyl carbonate

Conditions
ConditionsYield
In methanol at 20℃; for 15h; Inert atmosphere;100%
In methanol for 16h; Inert atmosphere;99%
75-59-2

tetramethyl ammoniumhydroxide

385-00-2

2,6-difluorobenzoic acid

C7H3F2O2(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
632-46-2

2,6-dimethylbenzoic acid

75-59-2

tetramethyl ammoniumhydroxide

C9H9O2(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
1466-76-8

2-6-dimethoxybenzoic acid

75-59-2

tetramethyl ammoniumhydroxide

C9H9O4(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
602-94-8

Pentafluorobenzoic acid

75-59-2

tetramethyl ammoniumhydroxide

C7F5O2(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
455-24-3

4-trifluoromethylbenzoic acid

75-59-2

tetramethyl ammoniumhydroxide

C8H4F3O2(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
50685-26-2

4-(cyanomethyl)benzoic acid

75-59-2

tetramethyl ammoniumhydroxide

C9H6NO2(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
1079-02-3

benzoic acid-2,3,4,5,6-d5

75-59-2

tetramethyl ammoniumhydroxide

C7(2)H5O2(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
456-22-4

4-Fluorobenzoic acid

75-59-2

tetramethyl ammoniumhydroxide

tetramethylammonium 4-fluorobenzoate

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
In methanol at 20℃; for 16h; Inert atmosphere; Glovebox;82%
75-59-2

tetramethyl ammoniumhydroxide

99-94-5

p-Toluic acid

tetramethyl-ammonium; 4-methyl-benzoate

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
75-59-2

tetramethyl ammoniumhydroxide

330-12-1

4-trifluoromethoxybenzoic acid

C8H4F3O3(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
619-86-3

4-(ethoxy)benzoic acid

75-59-2

tetramethyl ammoniumhydroxide

C9H9O3(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
75-59-2

tetramethyl ammoniumhydroxide

100-09-4

4-methoxybenzoic acid

111536-98-2

tetramethylammonium 4-methoxybenzoate

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
2215-77-2

4-Phenoxybenzoic acid

75-59-2

tetramethyl ammoniumhydroxide

C13H9O3(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
75-59-2

tetramethyl ammoniumhydroxide

98-73-7

4-(1,1-dimethylethyl)benzoic acid

C11H13O2(1-)*C4H12N(1+)

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
142-08-5

2-hydroxypyridin

75-59-2

tetramethyl ammoniumhydroxide

C5H4NO(1-)*C4H12N(1+)

Conditions
ConditionsYield
In ethanol; water at 20℃; for 24h;100%
75-59-2

tetramethyl ammoniumhydroxide

1605-65-8

N,N,N',N'-Tetramethylphosphorodiamidic chloride

A

93048-79-4

tetramethylammonium bis(dimethylamino)phosphate

B

75-57-0

tetramethlyammonium chloride

Conditions
ConditionsYield
In water for 3h;A 99.5%
B n/a
75-59-2

tetramethyl ammoniumhydroxide

108-29-2

5-methyl-dihydro-furan-2-one

1211890-38-8

tetramethylammonium 4-hydroxyvalerate

Conditions
ConditionsYield
In water for 1h;99.5%
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    Tetramethylammonium hydroxide CAS: 75-59-2

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    Appearance: Colorless liquid CAS NO.: 75-59-2 Formula: C4H13NO M.W.: 91.15 Application: Widely used in electronic industry , especially as positive resister developer ,silicon wafer wet etchant and super clean solution for CMP process. A

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Specification

Tetramethylammonium hydroxide, with the CAS registry number 75-59-2, is also known as TMAH. It belongs to the product categories of Quarternary Ammonium Bases; Ammonium Hydroxides (Quaternary); Ion Pair Reagents; Ion Pair Reagents - Anionic Concentrate. Its EINECS number is 200-882-9. This chemical's molecular formula is C4H13NO and molecular weight is 91.15. Its IUPAC name is called tetramethylammonium hydroxide.It is a colourless to yellow liquid with a strong ammonia-like odor which is stable,flammable,incompatible with strong oxidizing agents,strong acids.

Properties of Tetramethylammonium hydroxide:
(1)H-Bond Donor: 1; (2)H-Bond Acceptor: 1; (3)Rotatable Bond Count: 0; (4)Exact Mass: 91.099714; (5)MonoIsotopic Mass: 91.099714; (6)Topological Polar Surface Area: 1; (7)Heavy Atom Count: 6; (8)Formal Charge: 0; (9)Complexity: 19.1; (10)Isotope Atom Count: 0; (11)Defined Atom StereoCenter Count: 0; (12)Undefined Atom StereoCenter Count: 0; (13)Defined Bond StereoCenter Count: 0; (14)Undefined Bond StereoCenter Count: 0; (15)Covalently-Bonded Unit Count: 2.

Structure Descriptors of
Tetramethylammonium hydroxide:
(1)Canonical SMILES: C[N+](C)(C)C.[OH-]
(2)InChI: InChI=1S/C4H12N.H2O/c1-5(2,3)4;/h1-4H3;1H2/q+1;/p-1
(3)InChIKey: WGTYBPLFGIVFAS-UHFFFAOYSA-M

Toxicity of Tetramethylammonium hydroxide is as follows :

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo parenteral 5mg/kg (5mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 688, 1948.
frog LDLo unreported 1515ug/kg (1.515mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 681, 1948.
guinea pig LD50 skin 25mg/kg (25mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" National Technical Information Service. Vol. OTS0570994,
mouse LDLo subcutaneous 19mg/kg (19mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 28, Pg. 367, 1926.
rabbit LDLo intravenous 1mg/kg (1mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 688, 1948.

Use of Tetramethylammonium hydroxide
Tetramethylammonium hydroxide can be used to produce tetramethyl-ammonium; azide. This reaction will need reagent HN3•H2O and solvents CHCl3, H2O. The yield is about 60%.

Tetramethylammonium hydroxide can be used to produce tetramethyl-ammonium; azide
Tetramethylammonium hydroxide is used as an anisotropic etchant of silicon. It is also used as a basic solvent in the development of acidic photoresist in the photolithography process. Since it is a phase transfer catalyst, it is highly effective in stripping photoresist. It is also used as a surfactant in the synthesis of ferrofluid, to prevent agglomeration.

Safety information of Tetramethylammonium hydroxide:
When you are using Tetramethylammonium hydroxide, please be cautious about it as the following:Tetramethylammonium hydroxide may destroy living tissue on contact and may cause burns. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).