Tetramethylammonium hydroxide

HCID 60966CAS 75-59-2

Basic information

Standard SMILES
C[N+](C)(C)C.[OH-]
InChIKey
WGTYBPLFGIVFAS-UHFFFAOYSA-M
Molecular formula
C4H12N.HO
Average molar mass
91.15 g/mol
Monoisotopic mass
91.09971404

Overview

Tetramethylammonium hydroxide is a solid in the hydrated form or a colorless liquid with a strong ammonia-like odor. It is soluble in water. It is corrosive to metals and tissue.

Names & identifiers

Preferred name
Tetramethylammonium hydroxide
IUPAC
tetramethylazanium hydroxide
English name
Tetramethylammonium hydroxide
Molecular formula
C4H13NO
Molecular weight
91.15

Names & synonyms

TETRAMETHYLAMMONIUM HYDROXIDE75-59-2TMAHNMW-WHydroxyde de tetramethylammoniumAmmonium, tetramethyl-, hydroxideNMD 3Tetramethyl ammonium hydroxideDTXSID3029108Methanaminium, N,N,N-trimethyl-, hydroxide5GKP7317Q2DTXCID309108
Show more names
TetramethyLDeveloperTetramethylammonium hydroxide, 10% in waterTMNOHN,N,N-TRIMETHYLMETHANAMINIUM HYDROXIDETetramethylammonium hydroxide, 25% w/w in methanolTETRAMETHYLAMMONIUM HYDROXIDE SOL., 6% IN PROPYLENEGLYCOLnmd3
Methanaminium, N,N,N-trimethyl-, hydroxide (1:1)RefChem:6296200-882-9TMAOHtetramethylazanium;hydroxideMFCD00008280C4H13NOTetramethylammonium hydroxide solution

Database identifiers

CAS
75-59-2
PubChem CID
60966
DTXSID
DTXSID3029108
ChEMBL
CHEMBL3187523
UNII
5GKP7317Q2
EC Number
200-882-9

Properties

Computed structural properties

Topological polar surface area
1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
6

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Bases

Corrosives

OdorStrong ammonia-like
Density · 2 items

Specific gravity of solution approximately 1.00 at 24 °C/4 °C

1 @25 °C

Color/Form · 2 items

The free base is known only in solution or as a solid pentahydrate, forming colorless, deliquescent needles

Liquid

CorrosivityCorrosive
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides and ammonia/.

Physicochemical properties

Melting point
°C
Boiling point
110 °C · 110 °C
Density
0.866 g/mL · 0.866 g/mL at 25 °C
vapor pressure
17.5 mm · 17.5 mm Hg ( 20 °C)
refractive index
20 · n20/D 1.384
Flash point
80 °F · 80 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H300+H310 (36%): Fatal if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

P260, P262, P264, P264+P265, P270, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P308+P316, P316, P317, P319, P321, P330, P361+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 559 reports by companies from 44 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

Hazard information

Regulatory Information · 5 items

Chemical: Methanaminium, N,N,N-trimethyl-, hydroxide

Methanaminium, N,N,N-trimethyl-, hydroxide (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methanaminium, N,N,N-trimethyl-, hydroxide (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 17-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14295

Tetramethylammonium hydroxide: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Tetramethylammonium hydroxide and its pentahydrate: Human health tier II assessment
DOT LabelCorrosive
Fire Hazards · 3 items

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

· Combustible material: may burn but does not ignite readily.

Fire PotentialNot flammable or combustible. /Tetramethylammonium hydroxide pentahydrate/
Health Hazards · 3 items

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Safety & protection

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Accidental Release Measures · 4 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 items

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

General First Aid:

General First Aid:

Exposure Control and Personal Protection · 2 items

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

Fire Fighting Procedures · 3 items

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flodding quantities as fog. Cool all affected containers with flooding quantities of water. Applyy water from as far a distance as possible. Solid streams of water may be ineffective. Use "alcohol" foam, dry chemical or carbon dioxide.

Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for firefighters; Wear self contained breathing apparatus for fire fighting if necessary. /Tetramethylammonium hydroxide pentahydrate/

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Store under inert gas. Air sensitive. hygroscopic. /Tetramethylammonium hydroxide pentahydrate/

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8(SRC), determined from a structure estimation method(2), indicates that tetramethylammonium hydroxide is expected to have very high mobility in soil(SRC). Volatilization of tetramethylammonium hydroxide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.6X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Tetramethylammonium hydroxide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). A 96% of theoretical BOD using activated sludge in the Japanese MITI test(4) suggests that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8(SRC), determined from a structure estimation method(2), indicates that tetramethylammonium hydroxide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.6X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -2.47(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 96% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetramethylammonium hydroxide, which has an estimated vapor pressure of 1.2X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tetramethylammonium hydroxide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 days(SRC), calculated from its rate constant of 5.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase tetramethylammonium hydroxide may be removed from the air by wet and dry deposition(SRC). Tetramethylammonium hydroxide does not contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of tetramethylammonium hydroxide can be estimated to be 8(SRC). According to a classification scheme(2), this estimated Koc value suggests that tetramethylammonium hydroxide is expected to have very high mobility in soil.

Human Toxicity Excerpts · 4 items

/SIGNS AND SYMPTOMS/ Extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema.

/CASE REPORTS/ Tetramethylammonium hydroxide (TMAH) is widely used as a developer or etchant in semiconductor and photoelectric industries. In addition to alkalinity-related chemical burn, dermal exposure to TMAH may also result in respiratory failure and/or sudden death. The latter toxic effect has been of great concern in Taiwan after the occurrence of three fatalities in recent years. To better understand the toxicity following dermal exposure to TMAH, we analyzed all cases with TMAH exposure reported to the Taiwan Poison Control Center (PCC-Taiwan). In total, there were 13 cases of such exposure, including three patients who died after being exposed to 25% TMAH. A worker also developed severe effects manifesting muscle weakness, dyspnea, hyperglycemia, and chemical burn (28% of total body surface area) shortly after an accidental exposure to 2.38% TMAH. He received endotracheal intubation with assisted ventilation for 2 days and survived. Skin corrosive injury related to the alkalinity of TMAH and the ganglionic toxicity of tetramethylammonium ion might contribute to the clinical manifestations that occurred after dermal TMAH exposure. Thorough skin decontamination followed by prompt respiratory support should be the mainstay in the management of dermal TMAH exposure. Preventive strategies are warranted as well to decrease future occupational TMAH exposures.

/CASE REPORTS/ The purpose of this study was to examine the cause of an accidental death from acute poisoning resulting from exposure to a cleaner containing tetramethylammonium hydroxide (TMAH) and to consider measures to prevent future cases. ... The victim was a 39-year-old male researcher with 7 years of work experience employed by a surfactant production company. The accident occurred when he was conducting a field test of a newly developed cleaner, containing 8.75% TMAH solution. The researcher spilled the cleaner on his work clothes in the area of both the hands/arms and legs. He was unconscious when discovered. An autopsy found no damage or injury that could have resulted in death other than burns to 12% of his body, and the cause of death was found to be acute poisoning by TMAH. TMAH is widely used in the electronics industry as a developer or cleaner. It is a dangerous material, causing neurotoxicity leading to respiratory failure by ganglion block that occurs through skin absorption, and no antidote has been developed yet. For this reason, it is best to completely prevent exposure by wearing proper personal protective equipment. Despite this fatal toxicity of TMAH, it is not classified in Korea as a "chemical requiring legal control". For this reason, it is urgent to raise awareness of the toxic properties of TMAH to prevent additional cases of TMAH poisoning.

/CASE REPORTS/ A 22 year old male engineer was accidentally drenched with concentrated tetramethylammonium hydroxide solution (TMAH) (25%, pH13.5) while conducting routine examination of the pipe system in a plant manufacturing thin film transistor liquid crystal displays (TFT0LCDs). He was wearing a clean room suit with plastic goggles, but not a mask. As TMAH sprayed over his head, he closed the valve and took a shower at the nearby emergency shower facility immediately for decontamination. When he was found by a co-worker about 15 minutes later, he suffered from general weakness and moderate salivation but was still conscious enough to describe the accident. the paramedical team arrived about 30 minutes after the accident and found the patient losing his consciousness with a Glasgow coma scale of 6 (E1V2M3). His pulse was weak and noted as 8-10 times per minute, and miosis was also noted. he lost vital signs about half an hour later on the way to the hospital. He was diagnosed as dead on arrival at the hospital, as neither pulse nor breath was found; no electroactivity was shown by the electrocardiogram, and miosis without reaction to light was noted. Multiple glossy and erythematous erosive wounds were noted over his perineum, all four limbs, and face except for the nares and mouth. After cardiopulmonary resuscitation with 2 mg epinephrine bolus injection and 500 mL normal saline challenge intravenously, his heart beats and blood pressure were restored, but he still needed invasive mechanical ventilation. Laboratory tests on the day of the accident revealed leukocytosis, hyperglycemia, and metabolic acidosis, but levels of aspartate aminotransferase (AS), alanine aminotransferase (ALT), blood urea nitrogen (BUN), creatinine, and electrolytes were all within normal limits. The results of chest X-ray examinations on admission and during follow-up excluded the diagnoses of inflammation airway and aspiration pneumonia. According to his family, he did not have any systemic diseases before this accident. Because he had second-degree chemical burns on 24% of the total body surface area (TBSA) and third-degree burns on 5% of the TBSA, he was admitted to the burn center for further management. He never regained consciousness and suffered from hypothermia, seizure, and electrolyte imbalance. He passed away eight days later.

Artificial Pollution Sources · 1 item

Tetramethylammonium hydroxide's production and use as an etchant in circuit board production(1) and as a buffering agent, titrant, chemical reagent, and in digestion of biological samples(2) may result in its release to the environment through various waste streams(SRC).

Environmental BiodegradationAEROBIC: Tetramethylammonium hydroxide, present at 100 mg/L, reached 96% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1).

Safety data

F
4.4-10-34
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
PA0875000
ridadr
UN 3423 6.1/PG I (TETRAMETHYLAMMONIUM HYDROXIDE, SOLID)

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

Agents that mimic neural transmission by stimulation of the nicotinic receptors on postganglionic autonomic neurons. Drugs that indirectly augment ganglionic transmission by increasing the release or slowing the breakdown of acetylcholine or by non-nicotinic effects on postganglionic neurons are not included here nor are the nonspecific cholinergic agonists.

Uses & manufacturing

Uses · 6 items

In semiconductor manufacturing, TMAH is used to develop the pattern in the photoresists; [CHS, p. 44]

Semiconductor Manufacturing [Category: Industry]

Buffer; titrant; ion pair reagent; anisotropic etchant for silicon; in digestion of biological samples.

In electronics - surfactant/buffering agent in a developing solution for producing printed circuit boards ... surface active agent in formulation for polishing semiconductor wafers.

Chemical analysis basic medium

In lithography for development

U.S. Production · 5 items

2023: 50,000,000 - <100,000,000 lb

Methanaminium, N,N,N-trimethyl-, hydroxide is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#8127]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Methanaminium, N,N,N-trimethyl-, hydroxide. Aggregated National Production Volume: 10 to < 50 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Methanaminium, N,N,N-trimethyl-, hydroxide. National Production Volume: Withheld.

Consumer UsesAdhesion/cohesion promoter
Industry UsesLaboratory chemicals
Formulations/PreparationsAvailable in 10% solution.
General Manufacturing Information · 4 items

Plastics Material and Resin Manufacturing

Methanaminium, N,N,N-trimethyl-, hydroxide (1:1): ACTIVE

A strong base available in 10% solution

Commercial product sold as a 25% solution in water or methanol

Applications · 4 items

DescriptionTetramethylammonium hydroxide is a solid in the hydrated form or a colorless liquid with a strong ammonia-like odor. It is soluble in water, and corrosive to metals and tissue.

Uses▼▲ Industry Application Role/benefit Organic silicon Production of dimethyl silicone oil, organic silicon resin, silicon rubber, etc. Catalyst/removed easily; no pollution to the products Chemical analysis Polarography experiment Polarographic reagent Thermochemolysis to study fungal degradation of wood Analytical reagent Chemical purification Removal of metal elements Ash free alkali/source of base; make the metal elements precipitated Electron Production of computer silicon chip Brightening agent; anisotropic etching agent; cleaning agent; photoresist developer Printing of circuit board Cleaning agent Semiconductor manufacturing Chemical stripper Others Synthesis of ferrofluid Surfactant/ inhibit nanoparticle aggregation Synthesis of zeolite Structure directing agent

UsesTetramethylammonium hydroxide is used to produce tetramethyl-ammonium azide. It is used as an anisotropic etchant of silicon, basic solvent in the development of acidic photoresist in photolithography process, as surfactant in the synthesis of ferrofluid and as a polarographic reagent. It finds application in the production of organic silicon, where it is used for computer silicon wafer surface brightener and cleaning agent. It is also involved in the purification of some metallic elements.Tetramethylammonium hydroxide solution (25 wt.% solution in water) may be used as a base for pH adjustment to obtain hexagonal mesoporous aluminophosphate (TAP).

General DescriptionTetramethylammonium hydroxide is a quaternary ammonium salt generally used as an anisotropic etchant for silicon due to its high silicon etching rate.

Preparation methods · 1 item

PreparationThere are many methods for preparing tetramethylammonium hydroxide, the most common being the silver oxide method, which involves the reaction of tetramethylammonium chloride with silver oxide. However, this method is complex, uses expensive silver oxide as a raw material, and produces a product with high levels of impurity ions, such as halide ions and alkali metal ions. When used in the catalytic polymerization of organosilicon monomers, this severely affects the properties of the organosilicon products and fails to meet the cleaning and corrosion requirements of the electronics industry. Since the 1970s, foreign countries have adopted a new electrolytic process for preparing tetramethylammonium hydroxide, gradually replacing the silver oxide method. The electrolytic method produces a product of better quality and lower cost, meeting the needs of organosilicon production and entering the electronics industry.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
广州纳珑化工有限公司13192879270; 13192879270 · [email protected]
湖北鑫杰成化工科技有限公司13554075426 · [email protected]

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