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Cas Database |
| Name |
Tetramethylammonium hydroxide |
EINECS | 200-882-9 |
| CAS No. | 75-59-2 | Density | 0.866 g/mL at 25 °C |
| PSA | 23.06000 | LogP | 0.14560 |
| 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; |
Article Data | 27 |
Tetramethylammonium hydroxide Synthetic route
- 67-56-1
methanol
- 616-38-6
carbonic acid dimethyl ester
- 75-50-3
trimethylamine
- 75-59-2
tetramethyl ammoniumhydroxide
| 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% |
| 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; |
| Conditions | Yield |
|---|---|
| With ammonia die Salze entstehen; |
| Conditions | Yield |
|---|---|
| With water Herstellung einer wss. Loesung mit Hilfe eines Anionenaustauschers; |
| 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; |
| Conditions | Yield |
|---|---|
| With methanol at 100℃; die Salze entstehen; |
| Conditions | Yield |
|---|---|
| With methanol at 100℃; die Salze entstehen; |
| Conditions | Yield |
|---|---|
| With methanol at 100℃; die Salze entstehen; |
| Conditions | Yield |
|---|---|
| Kochen des erhaltenen Methylsulfats mit verd.H2SO4 und anschliessende Umsetzung mit Ba(OH)2; |
| Conditions | Yield |
|---|---|
| With methanol at 100℃; die Salze entstehen; |
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).
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