Tetramethylammonium hydroxide supplier

Name
Tetramethylammonium hydroxide
EINECS 200-882-9
CAS No. 75-59-2
Article Data27
CAS DataBase
Density 0.866 g/mL at 25 °C
Solubility Soluble in water.
Melting Point °C
Formula C₄H₁₃NO
Boiling Point 110 °C
Molecular Weight 91.1533
Flash Point 80 °F
Transport Information UN 3286 3/PG 2
Appearance colourless to yellow liquid
Safety 45-36/37/39-26-16-36/37
Risk Codes 24/25-34-20/21/22-39/23/24/25-23/24/25-10-21/22-25-21-11-67-36
Molecular Structure
Hazard Symbols C,F,T
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;
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

Conditions	Yield
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%

...Expand

: 64-20-0
tetramethylammonium bromide

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
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

Conditions	Yield
With ammonia die Salze entstehen;

: 75-58-1
tertamethylammonium iodide

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
With water Herstellung einer wss. Loesung mit Hilfe eines Anionenaustauschers;

: 75-57-0
tetramethlyammonium chloride

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
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

Conditions	Yield
With methanol at 100℃; die Salze entstehen;

: 598-58-3
methyl nitrate

: 124-40-3
dimethyl amine

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
With methanol at 100℃; die Salze entstehen;

: 124-40-3
dimethyl amine

: 74-88-4
methyl iodide

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
With methanol at 100℃; die Salze entstehen;

: 77-78-1
dimethyl sulfate

: 75-50-3
trimethylamine

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
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

Conditions	Yield
With methanol at 100℃; die Salze entstehen;

: 598-58-3
methyl nitrate

: 74-89-5
methylamine

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
With methanol at 100℃; die Salze entstehen;

: 74-89-5
methylamine

: 74-88-4
methyl iodide

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
With methanol at 100℃; die Salze entstehen;

: 74-86-2
acetylene

: 75-50-3
trimethylamine

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
With water at 105℃; unter Druck;

: 74-83-9
methyl bromide

: 75-50-3
trimethylamine

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
die Salze entstehen;

: 74-87-3
methylene chloride

: 75-50-3
trimethylamine

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
die Salze entstehen;

: 13448-18-5
trimethyl-vinylammonium cation

: 75-50-3
trimethylamine

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
With water at 110 - 120℃;

: 74-88-4
methyl iodide

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
With ammonia; water die Salze entstehen;
With ethanol; ammonia die Salze entstehen;

: 58345-96-3
Tetramethylammonium hydrogen carbonate

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
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

Conditions	Yield
With water

trimethylacetonylammonium bromide: trimethylacetonylammonium bromide

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
at 195 - 200℃; die Salze entstehen;

: 74-88-4
methyl iodide

trimethylazonium iodide: trimethylazonium iodide

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

: tetramethylammonium sulfate

: 75-59-2
tetramethyl ammoniumhydroxide

Conditions

Conditions	Yield
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

Conditions	Yield
With basic anion exchanger In water Product distribution / selectivity;

: 1569-69-3
Cyclohexanethiol

: 75-59-2
tetramethyl ammoniumhydroxide

: 138555-12-1
Cyclohexanethiolatetetramethyl-ammonium;

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 1160694-10-9
C29H28N2O7S

: 75-59-2
tetramethyl ammoniumhydroxide

: C4H12N(1+)*C29H27N2O7S(1-)

Conditions

Conditions	Yield
In methanol; dichloromethane at -78℃;	100%

: 75-59-2
tetramethyl ammoniumhydroxide

: 65-85-0
benzoic acid

: 25255-90-7
tetramethylammonium benzoate

Conditions

Conditions	Yield
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

Conditions	Yield
In water at 40℃;	100%

...Expand

: 78-10-4
tetraethoxy orthosilicate

: 75-59-2
tetramethyl ammoniumhydroxide

: octakis(tetramethylammonium)silsesquioxane

Conditions

Conditions	Yield
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

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

...Expand

: 2634-33-5
1,2-benzisothiazolin-3-one

: 75-59-2
tetramethyl ammoniumhydroxide

: 400089-65-8
tetramethylammonium 1,2-benzisothiazol-3-one

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In methanol at 0 - 20℃; for 2h;	100%

: 75-59-2
tetramethyl ammoniumhydroxide

: 616-38-6
carbonic acid dimethyl ester

: tetramethylammonium methyl carbonate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In water for 3h;	A 99.5% B n/a

...Expand

: 75-59-2
tetramethyl ammoniumhydroxide

: 108-29-2
5-methyl-dihydro-furan-2-one

: 1211890-38-8
tetramethylammonium 4-hydroxyvalerate

Conditions

Conditions	Yield
In water for 1h;	99.5%

Tetramethylammonium hydroxide Consensus Reports

Reported in EPA TSCA Inventory.

Tetramethylammonium hydroxide 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 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).

Product Name

Tetramethylammonium hydroxide

Synthetic route

Tetramethylammonium hydroxide Consensus Reports

Tetramethylammonium hydroxide Specification

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