75-57-0

Basic information

• Product Name: Tetramethylammonium chloride
• Synonyms: Ammonium, tetramethyl-, chloride;Methanaminium, N,N,N-trimethyl-, chloride;Methanaminium,N,N,N-trimethyl-,chloride;n,n,n-trimethyl-methanaminiuchloride;tetramethyl-ammoniuchloride;tetraminechloride;USAF AN-8;usafan-8
• CAS NO: 75-57-0
• Molecular Formula: C₄H₁₂N*Cl
• Molecular Weight: 109.6
• EINECS: 200-880-8
• Product Categories: quarternary ammonium salts;Ammonium Chlorides (Quaternary);Quaternary Ammonium Compounds;Ammonium SaltsNucleic Acid Detection and Hybridization;Greener Alternatives: Catalysis;Hybridization Kits and Reagents;Phase Transfer Catalysts;Reagents for Hybridization;Quaternary ammonium salt;Pharmaceutical intermediates;fine chemical
• Mol File: 75-57-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 165.26°C (rough estimate)
• Appearance: White to ivory/Hygroscopic Crystalline Powder
• Density: 1,17 g/cm3
• Vapor Pressure: 3965.255mmHg at 25°C
• Refractive Index: 1.5320 (estimate)
• Storage Temp.: Store at RT.
• Solubility: methanol: 0.1 g/mL, clear, colorless
• Water Solubility: >60 g/100 mL (20 ºC)
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents, water. Hygroscopic.
• BRN: 2496575
• CAS DataBase Reference: Tetramethylammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Tetramethylammonium chloride(75-57-0)
• EPA Substance Registry System: Tetramethylammonium chloride(75-57-0)

Safety Data

• Hazard Codes: T,Xn
• Statements: 21-25-36/37/38-20/21/22
• Safety Statements: 26-36/37-45-37/39-28A-28-36
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 1
• RTECS: BS7700000
• F: 3-10
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 75-57-0(Hazardous Substances Data)

Usage

Catalyst of Organic synthesis

Tetramethylammonium chloride is the phase transfer catalyst in organic synthesis phase with its catalytic activity being stronger than triphenylphosphine and triethylamine. At room temperature, it is a white crystalline powder, and is volatile, irritant, and easy to absorb moisture. It is easily soluble in methanol, soluble in water and hot ethanol but insoluble in ether and chloroform. Being heated to above 230 °C causes its decomposition into trimethylamine and methyl chloride. Median lethal dose (mice, intraperitoneal) is around 25mg/kg. It is also used for the synthesis of liquid crystal epoxy compound, and Pope and polarographic analysis, as well as electronic industry. The above information is edited by the lookchem of Dai Xiongfeng.

Electrolytic preparation of tetramethylammonium hydroxide

Tetramethylammonium hydroxide is a kind of organic base, and has a broad range of application in the field of both industry and scientific research. In our own country, it is mainly used as the catalyst in the synthesis of organic silicon products, such as synthetic silicone oil, silicone rubber, and silicone resin. Although it has a low usage amount, but it can significantly affect both the yield and quality of the product. In abroad, it is mainly used for polyester-based polymers, textiles, plastics, food, leather, wood processing, electroplating, and some kinds of microorganisms. Now tetramethylammonium hydroxide has entered the advanced technology areas. For example, in the field of manufacturing industry of electronic circuit and microscopic sheets production, it can be used as the cleaning agent of integrated circuit board as well as the anisotropic corrosive agents of the Si-SiO2 interface in semiconductor microfabrication technique. With the development of science and technology, the requirements of this type of chemicals are also increasing, posing higher requirements for both the quality and the quantity of the tetramethylammonium hydroxide. The basic principle of using electrolytic method for preparation of tetramethylammonium hydroxide is that the aqueous solution of tetramethylammonium chloride in the anode compartment of the electrolytic bath, under the action of the electric force, has its chloride ions migrate to the direction of anode until discharge of anode occurs to generate chlorine. Meanwhile, because of the selective permeability of the ion-exchange membrane, chloride can’t penetrate through the ion-exchange membrane through diffusion. Instead, only tetramethylammonium ions can selectively penetrate into the cathode compartment through, and be enriched over there. The water molecule in the electrolyzer cathode chamber is decomposed into hydrogen and hydroxyl ions. The latter one exactly binds to the tetramethylammonium ions migrated from the anode chamber to generate tetramethylammonium hydroxide. With the increase of electricity, tetramethylammonium hydroxide concentration continues to improve, finally achieving the desired final concentration of crude. The anodic electrochemical reaction is: (CH3) 4NCl → (CH3) 4N ++ Clˉ2Clˉ-2e → Cl2 ↑ The cathodic electrochemical reaction is: H2O → H + + OHˉ (CH3) 4N ++ OHˉ → (CH3) 4NOH 2H ++ 2e → H2 ↑ The total reaction is: 2 (CH3) 4NCl + 2H2O → 2 (CH3) 4NOH + H2 ↑ + Cl2 ↑ The hydrogen generated during electrolysis is vented with the resulting chlorine absorbed by alkaline solution to generate sodium hypochlorite which is major raw materials for producing bleach. Therefore, this method of producing tetramethylammonium hydroxide is simple with high purity and causing no environmental pollution.

The preparation of PHBHQ type thermoset Liquid crystalline epoxy resin (LCER)

Use toluene as the solvent, concentrated sulfuric acid and boric acid as the catalyst, add into the three-necked flask of equal amount of hydroxybenzoic acid and 1,4-hydroquinone, have reaction at 120~130 °C for 6 h; after cooling, repeatedly wash with distilled water, and obtain the p-hydroxybenzoic acid p-hydroquinone ester after vacuum dry (white solid, yield 87.5%). Dissolve the above product in an excess amount of epichlorohydrin, further add tetramethylammonium chloride and have reaction at 60~70 °C for 10 h; add drop wise of excess amount of aqueous 45% NaOH solution (the addition takes 6 h). Excess amount epichlorohydrin was distilled off under reduced pressure; wash the reaction mixture with acetone-methanol mixed solution for crystallization; it is further subject to vacuum drying to obtain a white PHBHQ-type thermosetting liquid crystalline epoxy resin (with the yield being 37.5%). Mix PHBHQ and hardener stoichiometrically for heating and melting, casting with the curing process being 90 ℃ × 1h; 120 ℃ × 2h; 150 ℃ × 2h; 180 ℃ × 2h.

Uses

Different sources of media describe the Uses of 75-57-0 differently. You can refer to the following data:
1. 1. It can be used as polarographic analysis reagents which is widely used in the electronics industry. 2. Tetramethylammonium chloride is the phase transfer catalyst in organic synthesis with its catalytic activity being stronger than triphenylphosphine and triethylamine. At room temperature, it is a white crystalline powder, and is volatile, irritant, and easy to absorb moisture. It is easily soluble in methanol, soluble in water and hot ethanol but insoluble in ether and chloroform. Being heated to above 230 °C causes its decomposition into trimethylamine and methyl chloride. Median lethal dose (mice, intraperitoneal) is around 25mg/kg. It is also used for the synthesis of liquid crystal epoxy compound, and Pope and polarographic analysis, as well as electronic industry.
2. Chemical intermediate, catalyst, inhibitor.
3. Tetramethylammonium chloride along with N-hydroxyphthalimide and xanthone may be used as an efficient chloride catalytic system for the aerobic oxidation of hydrocarbons to form the corresponding oxygenated compounds. It may also be used as a phase transfer catalyst for the synthesis of aryl fluorides via selective chloride/fluoride exchange reaction of activated aryl chlorides with potassium fluoride in solid-liquid phase.
4. TMAC may be used in ion-exchange procedures to show the increase of pH in understanding the chemical behaviour of catalyst [CTA]Si-MCM-41 using Knoevenagel condensation model.

Chemical Properties

white crystals

General Description

Tetramethylammonium chloride is a quaternary ammonium salt commonly used as a catalyst due to its thermal stability and also tolerance towards strong aqueous bases or nucleophiles.

Safety Profile

Poison by ingestion, intraperitoneal, and subcutaneous routes. When heated to decomposition it emits very toxic fumes of NOx, NH3, and Cl-. See also CHLORIDES.

Purification Methods

Crystallise the chloride from EtOH, EtOH/CHCl3, EtOH/diethyl ether, acetone/EtOH (1:1), isopropanol or water. Traces of the free amine can be removed by washing with CHCl3. [Beilstein 4 IV 145.]

InChI:InChI=1/C4H12N.ClH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1

Synthetic route

tetramethyl ammoniumhydroxide (75-59-2) + N,N,N',N'-Tetramethylphosphorodiamidic chloride (1605-65-8) → tetramethylammonium bis(dimethylamino)phosphate (93048-79-4) + tetramethlyammonium chloride (75-57-0)

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

trimethylamine hydrochloride (593-81-7) + carbonic acid dimethyl ester (616-38-6) → tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With 1-ethyl-3-methylimidazolium bromide at 169.84℃; for 8h;	99%
With 1-ethyl-3-methylimidazolium bromide at 169.84℃; for 8h;

carbonic acid dimethyl ester (616-38-6) → tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With ammonium chloride at 169.84℃; for 8h;	96%
With ammonium chloride at 169.84℃; for 8h;	96%

benzoyl chloride (98-88-4) + dimethyl-amidophosphoric acid monomethyl ester; tetramethylammonium salt (63581-76-0) → tetramethlyammonium chloride (75-57-0) + C10H14NO4P (106997-48-2)

Conditions	Yield
In acetonitrile for 3h; Ambient temperature;	A n/a B 93%

Hg((2-phenylazo)phenyl)2 + bis(tetramethylammonium) {TlCl5} → tetramethylammonium trichloro(2-phenylazophenyl)thallate(III) + 2N(CH3)4(1+)*Hg2Cl6(2-)=[N(CH3)4]2[Hg2Cl6] + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
In ethanol refluxing (6 h), solvent evapn. to dryness; residue recrystn. from dichloromethane/diethyl ether; elem. anal.;	A 85% B n/a C n/a

(Me4N)2{Mo3(μ3-S)(μ2-S2)3Cl6} → (PPh3)3Mo3(μ3-S)(μ2-S)3Cl4 + tetramethlyammonium chloride (75-57-0) + triphenylphosphine sulfide (3878-45-3)

Conditions	Yield
With P(C6H5)3 In methanol Stirring of a suspn. of Mo-compd. and PPh3 (MeOH, 1 h).; Filtn. of pptd. green solid, washing with hot MeOH and benzene, drying (vac.), elem. anal.;	A 82% B n/a C >99

Hg(2-dimethylaminomethylphenyl-C'N)2 + bis(tetramethylammonium) {TlCl5} → tetramethylammonium trichloro(2-dimethylaminomethylphenyl-C'N)thallate(III) + 2N(CH3)4(1+)*Hg2Cl6(2-)=[N(CH3)4]2[Hg2Cl6] + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
In ethanol refluxing (6 h), solvent evapn. to dryness; residue recrystn. from dichloromethane/diethyl ether; elem. anal.;	A 77% B n/a C n/a

nido-B10H12CNMe3 (31117-16-5) + sodium hydride (7646-69-7) → tetramethlyammonium chloride (75-57-0)

Conditions	Yield
In tetrahydrofuran at 25°C;	60%

(Me4N)2{Mo3(μ3-S)(μ2-S2)3Cl6} → Mo3(μ3-S)(μ2-S)3(dppe)3Cl4 + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With C2H4(P2(C6H5)4) In methanol byproducts: (dppe)S2; Boiling of Mo-compd. with dppe (MeOH, 1 h).; Recrystn. of bright green ppt. from a CH2Cl2/hexane mixt., elem. anal.;	A 51% B n/a

methylene chloride (74-87-3) + Neopentyl N,N,N',N'-tetramethylphosphorodiamidite (105334-48-3) → tetramethlyammonium chloride (75-57-0) + Neopentyl N,N-dimethylphosphoramidochloridite + bisdimethylamino(methyl)neopentyloxyphosphonium chloride

Conditions	Yield
Ambient temperature;	A 10.4% B 17 % Spectr. C 30.1%

[platinum(II)dichloride(1,2-bis(diphenylphosphino)ethane)] (83095-83-4, 14647-25-7) + tetramethylammonium octahydrotriborate (12386-10-6) → (C2H5)3NB3H7 + 1-{1,2-bis(diphenylphosphino-κP)ethane}-1-platina-arachno-tetraborane(7) + triethylamine-borane (1722-26-5) + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With triethylamine In acetonitrile under inert atm., 5 h stirring, pptn. of NMe4Cl, solvent removed in vacuo; chromy., eluating of by-products with hexane and main product with toluene;	A n/a B 25% C n/a D n/a

N,N-dimethoxyamine (88470-26-2) + trimethylamine (75-50-3) → trimethylamine hydrochloride (593-81-7) + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With tert-butylhypochlorite In diethyl ether 1) -78 deg C, 0.5 h, 2) -8 deg C, 24 h;	A 15.7% B 22.8%

tetramethylammonium octahydrotriborate (12386-10-6) + (1,4-bis(diphenylphosphanyl)butane)dichloridoplatinum(II) (65097-96-3) → (C2H5)3NB3H7 + 1-{1,4-bis(diphenylphosphino-κP)butane}-1-platina-arachno-tetraborane(7) + triethylamine-borane (1722-26-5) + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With triethylamine In acetonitrile under inert atm., 5 h stirring, pptd. of NMe4Cl, solvent removed in vacuo; chromy., eluating of by-products with hexane, the main product with toluene;	A n/a B 20% C n/a D n/a

[1,3-bis(diphenylphosphino)propane]dichloroplatinum(II) (59329-00-9) + tetramethylammonium octahydrotriborate (12386-10-6) → cis-PtHCl(1,3-bis(diphenylphosphino)propane) (136813-66-6) + (dppp)PtB3H7 + (PtH(dppp)2)Cl (136813-67-7) + (Pt2H3((C6H5)2PCH2CH2CH2P(C6H5)2)2(1+))*Cl(1-)=(Pt2H3((C6H5)2PCH2CH2CH2P(C6H5)2)2)Cl + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With triethylamine In acetonitrile under inert atm., 5 h stirring, pptd. of NMe4Cl, solvent removed in vacuo, summarized yields of PtH(Cl)(dppp) and (PtH(dppp)2)Cl < 1%, further products; chromy., eluating of by-products with hexane, the main product with toluene, the (Pt2H3(dppp)2)Cl, PtH(Cl)(dppp) and (PtH(dppp)2)Cl with methanol, the PtH(Cl)(dppp) and (PtH(dppp)2)Cl were not isolated;	A n/a B 20% C n/a D 2% E n/a

[1,1'-bis(diphenylphosphino)ferrocene]platinum(II) chloride (104413-90-3) + tetramethylammonium octahydrotriborate (12386-10-6) → (C2H5)3NB3H7 + (((C6H5)2PC5H4)2Fe)PtB3H7 + triethylamine-borane (1722-26-5) + Pt2H3(((C6H5)2PC5H4)2Fe)2(1+)*Cl(1-)=Pt2H3(((C6H5)2PC5H4)2Fe)2Cl + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With triethylamine In acetonitrile under inert gas; stirring for 5 h;; evapn., washing, recrystn.;;	A n/a B 2% C n/a D 10% E n/a

methanol (67-56-1) → tetramethlyammonium chloride (75-57-0) + trimethylamine (75-50-3)

Conditions	Yield
With ammonium chloride at 285℃;

trimethylvinyl ammonium chloride (6018-82-2) → N,N-dimethylvinylamine (5763-87-1) + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
bei der trocknen Destillation im Stickstoffstrom;

methylene chloride (74-87-3) + dimethyl amine (124-40-3) → N,N-dimethylammonium chloride (506-59-2) + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
unter Druck;

diethyl ether (60-29-7) + benzenesulfonyl chloride (98-09-9) + trimethylamine (75-50-3) → N,N-dimethylbenzenesulfonamide (14417-01-7) + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
at 0℃;
at -80℃;

benzenesulfonyl chloride (98-09-9) + trimethylamine (75-50-3) → tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With diethyl ether at 0℃;

dimethyl sulfate (77-78-1) → tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With sodium hydroxide; ammonium chloride

methylene chloride (74-87-3) + methylamine (74-89-5) → methylamine hydrochloride (593-51-1) + tetramethlyammonium chloride (75-57-0)

Chloromethyltrimethylsilane (2344-80-1) + trimethylamine (75-50-3) → tetramethlyammonium chloride (75-57-0)

Conditions	Yield
at 210℃;

methylene chloride (74-87-3) + trimethylamine (75-50-3) → tetramethlyammonium chloride (75-57-0)

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → tetramethlyammonium chloride (75-57-0)

Conditions	Yield
With hydrogenchloride

(3-carboxypropyl)trimethylammonium chloride methyl ester (13254-33-6) → 4-butanolide (96-48-0) + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
at 0 - 250℃; Mechanism; Heating; pyrolysis of various carpronium chloride derivatives, labelled derivatives;

tetramethylammonium dimethyl phosphate (756-77-4) + benzoyl chloride (98-88-4) → benzoyl dimethyl phosphate (91489-49-5) + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
In acetonitrile for 3h; Ambient temperature;

tetramethylammonium bis(dimethylamino)phosphate (93048-79-4) + benzoyl chloride (98-88-4) → benzoic acid-(tetramethyl-diamidophosphoric acid )-anhydride (106997-52-8) + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
In acetonitrile for 3h; Ambient temperature; Title compound not separated from byproducts;

benzoyl chloride (98-88-4) + dimethyl-amidophosphoric acid monomethyl ester; tetramethylammonium salt (63581-76-0) → tetramethlyammonium chloride (75-57-0) + N,N-dimethylbenzamide (611-74-5)

Conditions	Yield
In acetonitrile for 4h; Heating;

benzoyl chloride (98-88-4) + C4H12N(1+)*C4H9NO4P(1-) (91489-48-4) → N-acetyl-N-acetylbenzamide (7449-76-5) + tetramethlyammonium chloride (75-57-0)

Conditions	Yield
In acetonitrile for 4h; Heating;

(2,11-(CH3)2-2,11-C2B9H9)2Ni + tetramethlyammonium chloride (75-57-0) → {N(CH3)4}{(1.2-C2B9H9(CH3)2)2Ni} (12556-57-9)

Conditions	Yield
With NaBH4 In ethanol redn. with 2-fold excess of NaBH4 in C2H5OH at room temp. (15 min), addn. of H2O, addn. of (N(CH3)4)Cl;; pptn.;;	100%
With NaBH4 In ethanol redn. with 2-fold excess of NaBH4 in C2H5OH at room temp. (15 min), addn. of H2O, addn. of (N(CH3)4)Cl;; pptn.;;	100%

(7,8-(CH3)2-7,8-C2B9H9)Ni(2,11-(CH3)2-2,11-C2B9H9) (33009-91-5) + tetramethlyammonium chloride (75-57-0) → {N(CH3)4}{(1.2-C2B9H9(CH3)2)2Ni} (12556-59-1)

Conditions	Yield
With NaBH4 In ethanol redn. with 2-fold excess of NaBH4 in C2H5OH at room temp. (15 min), addn. of H2O, addn. of (N(CH3)4)Cl;; pptn.;;	100%
With NaBH4 In ethanol redn. with 2-fold excess of NaBH4 in C2H5OH at room temp. (15 min), addn. of H2O, addn. of (N(CH3)4)Cl;; pptn.;;	100%

hydrogen tetrachloroaurate(III) tetrahydrate + tetramethlyammonium chloride (75-57-0) → tetramethyl-ammonium; tetrachloroaurate (III)

Conditions	Yield
In water under N2, light excluded; to aq. soln. of HAuCl4*4H2O (4.85 mmol) excess(Me4N)Cl added, stirred for 30 min; filtered, ppt. washed (H2O, EtOH, Et2O), vacuum-dried;	100%

tetramethlyammonium chloride (75-57-0) + nickel dichloride → 2{N(CH3)4}(1+)*{NiCl4}(2-)={N(CH3)4}2{NiCl4}

Conditions	Yield
In methanol under N2 or Ar; soln. of 3 equiv. of Me4NCl in MeOH heated to reflux; slurry of NiCl2 in MeOH added to boiling soln.; heated under reflux for 24h; filtered; solvent removed from filtrate under vac.;	99%
In ethanol 8:1 mixture; heating pptn. in i-pentanol;; pptn. washed with petroleum and dried at 60°C in vacuum;;
In ethanol 8:1 mixture; heating pptn. in i-pentanol;; pptn. washed with petroleum and dried at 60°C in vacuum;;
heating at 130-150°C for several hours; Evapn. of soln. of nitromethane in a vac. desiccator (CaSO4) yields to crystals.;

potassium tetrachloroplatinate(II) (10025-99-7) + tetramethlyammonium chloride (75-57-0) → tetramethylammonium tetrachloroplatinate(II)

Conditions	Yield
In water	99%

pentaborane(9) (19624-22-7) + tetramethlyammonium chloride (75-57-0) + potassium hydride → {(CH3)4N}(1+)*{B11H14}(1-)={(CH3)4N}{B11H14}

Conditions	Yield
In 1,2-dimethoxyethane byproducts: H2, KCl; condensing 20.9mmol B5H9 into the vessel containing 8.88mmol KH and 9.17mmol ammonium salt at -196°C, warming to ambient temp., heating to 85°C for 2h, filtation;; removal of volatile material in high vac. (<10E-3 mm Hg), heating to 90°C for 24h in vac.; NMR:;	99%

(HNMe3)(7-SPh-8-Me-7,8-C2B9H10) + water-d2 (7789-20-0) + tetramethlyammonium chloride (75-57-0) → (NMe4)(10-D-7-SPh-8-Me-7,8-C2B9H9)

Conditions	Yield
In tetrahydrofuran; water-d2 soln. Na2(7-SPh-8-Me-7,8-C2B9H9) in THF was prepared from (NHMe3)(7-SPh-8-Me-7,8-C2B9H10) (J.Am.Chem.So., 1968, V.90, P.862; P.879) and then treated with D2O and stirred under N2 for 15 min., THF was evapd. and Me4NCl in D2O was added; ppt. was filtered, washed with D2O and recrystd. from acetone/D2O; elem. anal.;	99%

trichlorotris(tetrahydrofuran)chromium(III) (10170-68-0, 16997-54-9) + nitrido{bis-N,N'-(salicylaldehyde)ethylenediiminato}manganese(V) (142021-25-8) + water (7732-18-5) + tetramethlyammonium chloride (75-57-0) + acetonitrile (75-05-8) → N,N'-ethylenebis(salicylideneiminato)manganese(III) chloride*acetonitrile (105241-53-0) + [Cr(N)Cl4](2-)*2N(CH3)4(1+)*H2O=[N(CH3)4]2[Cr(N)Cl4]*H2O

Conditions	Yield
In acetonitrile (N2); dissolving of CrCl3(THF)3 in CH3CN, addn. of Mn(N)(salen), stirring for 1 h, filtration, addn. of soln. of Me4NCl in CH3CN/C2H5OH/H2O (15:14:1) to filtrate; pptn., filtration, washing with CH3CN, drying, elem. anal.;	A 99% B 71%

Rh2(((C6H5)2PC2H4NCH3)2C6H4)(((C6H5)2PC2H4S)2C6H4)(2+)*2BF4(1-)=Rh2(((C6H5)2PC2H4NCH3)2C6H4)((C6H5)4P2C10H12S2)(BF4)2 + carbon monoxide (201230-82-2) + tetramethlyammonium chloride (75-57-0) → Rh2(((C6H5)2PC2H4NCH3)2C6H4)(((C6H5)2PC2H4S)2C6H4)(CO)2Cl2 (827609-97-2)

Conditions	Yield
In dichloromethane 1 atm. of CO, 2 equiv of (CH3)4NCl, CH2Cl2, room temp.;	99%

K[arachno-B9H14] + tetramethlyammonium chloride (75-57-0) → (CH3)4N(1+)*[B9H14](1-)=[(CH3)4N][B9H14]

Conditions	Yield
In further solvent(s) all manipulations in vacuum line or under inert atm.; arachno-borane andMe4NCl placed in flask fitted with Solv-Seal adapter, evacuated, glyme condensed into system, warmed to room temp., stirred for 1 h; ppt. filtered off, solvent removed in vac.;	99%

Rh2(((C6H5)2PC2H4S)2C6(CH3)4)(((C6H5)2PC2H4S)2C6H4)(2+)*2BF4(1-)=Rh2(((C6H5)2PC2H4S)2C6(CH3)4)((C6H5)4P2C10H12S2)(BF4)2 + carbon monoxide (201230-82-2) + tetramethlyammonium chloride (75-57-0) → Rh2(((C6H5)2PC2H4S)2C6(CH3)4)(((C6H5)2PC2H4S)2C6H4)(CO)2Cl2 (827609-96-1)

Conditions	Yield
In dichloromethane 1 atm. of CO, 2 equiv of (CH3)4NCl, CH2Cl2, room temp.;	99%

Rh2(((C6H5)2PC2H4O)2C14H8)(((C6H5)2PC2H4S)2C6H4)(2+)*2BF4(1-)=Rh2(((C6H5)2PC2H4O)2C14H8)((C6H5)4P2C10H12S2)(BF4)2 + carbon monoxide (201230-82-2) + tetramethlyammonium chloride (75-57-0) → Rh2(((C6H5)2PC2H4O)2C14H8)(((C6H5)2PC2H4S)2C6H4)(CO)2Cl2 (827609-98-3)

Conditions	Yield
In dichloromethane 1 atm. of CO, 2 equiv of (CH3)4NCl, CH2Cl2, room temp.;	99%

12-(4-methoxypyridinium)-closo-1-monocarbadodecaborate + tetramethlyammonium chloride (75-57-0) → C6H15B11NO(1-)*C4H12N(1+)

Conditions	Yield
Stage #1: 12-(4-methoxypyridinium)-closo-1-monocarbadodecaborate With lithium chloride In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere; Stage #2: tetramethlyammonium chloride for 2h; Inert atmosphere;	99%

[(η5-4,7-Me2C9H5)Mo(CO)2(6,6'-dimethyl-2,2'-bipyridine)][BF4] + tetramethlyammonium chloride (75-57-0) → [(η3-4,7-Me2C9H5)Mo(CO)2(6,6'-dimethyl-2,2'-bipyridine)Cl]

Conditions	Yield
In acetone for 48h; Inert atmosphere; Schlenk technique;	99%

tetramethlyammonium chloride (75-57-0) → tetramethylammonium dichloroiodate(I) (1838-41-1)

Conditions	Yield
With hydrogenchloride; sodium hypochlorite; sodium iodide at 20℃; for 0.5h;	98%
With hydrogenchloride; dihydrogen peroxide; iodine In water; acetonitrile at 20℃; Cooling with ice;	97%
With hydrogenchloride; potassium iodate
With water
With Iodine monochloride; acetic acid

1-methyl-2-methylthiolato-1,2-dicarba-closo-dodecaborane (17526-08-8) + tetramethlyammonium chloride (75-57-0) → tetramethylammonium 7-methyl-8-methylthiolato-S-7,8-dicarba-nido-undecaborate

Conditions	Yield
With KOH In ethanol refluxing of the starting dicarbaborane and KOH in ethanol for 2 h under N2, eliminating of ethanol, dissolving of residue in water, addn. of Me4NCl; filtn., rechrystn. (EtOH-H2O), elem. anal.;	98%

1-methyl-2-methylthiolato-1,2-dicarba-closo-dodecaborane (17526-08-8) + tetramethlyammonium chloride (75-57-0) → (SCH3)(CH3)C2B9H10(1-)*N(CH3)4(1+)

Conditions	Yield
With KOH In ethanol KOH is added to flask contg. deoxygenated ethanol, stirred for 1 h, carborane is added, mixt. is refluxed for 2 h, solvent is evapd., water is added, filtn., N2 is bubbled through soln., NMe4Cl in water is added, pptn.; filtn., washing (water), recrystd. (ethanol/water); elem. anal.;	98%

La2Na3(μ4-4-methylphenoxy)3(μ-4-methylphenoxy)6(THF)5 + tetramethlyammonium chloride (75-57-0) → {Me4N}{La2Na2(μ4-4-methylphenoxy)(μ3-4-methylphenoxy)2(μ-4-methylphenoxy)4(4-methylphenoxy)2(THF)5}(THF)

Conditions	Yield
In tetrahydrofuran (with exclusion of air and water) Me4NCl was added to a soln. of complex in THF, stirred for 24 h; centrifuged, evapd. to dryness; elem. anal.;	98%

(HNMe3)(7-SPh-8-Ph-7,8-C2B9H10) + water-d2 (7789-20-0) + tetramethlyammonium chloride (75-57-0) → (NMe4)(10-D-7-SPh-8-Ph-7,8-C2B9H9)

Conditions	Yield
In tetrahydrofuran; water-d2 soln. Na2(7-SPh-8-Ph-7,8-C2B9H9) in THF was prepared from (NHMe3)(7-SPh-8-Ph-7,8-C2B9H10) (J.Am.Chem.So., 1968, V.90, P.862; P.879) and then treated with D2O and stirred under N2 for 15 min., THF was evapd. and Me4NCl in D2O was added; ppt. was filtered, washed with D2O and recrystd. from acetone/D2O; elem. anal.;	98%

triisopropylsilyl chloride (13154-24-0) + trimethylammonium 12-iodocarba-closo-dodecaborane + tetramethlyammonium chloride (75-57-0) → tetramethylammonium 1-triisopropylsilyl-12-iodocarba-closo-dodecaborane

Conditions	Yield
With n-butyllithium In tetrahydrofuran byproducts: LiCl; n-butyllitium was added dropwise to a soln. of carborane in THF at 0°C, stirred for 30 min at room temp., cooled to 0°C, silyl-compound was added dropwise, stirred at room temp. for 3 h, the procedure was repeated; H2O was added, rotary evapd., H2O was added, (CH3)4NCl was added, ppt. was dried at 80°C overnight;	98%

1-(2-pyridyl)-1,2-dicarba-closo-dodecaborane(12) (153984-80-6) + tetramethlyammonium chloride (75-57-0) → 7-(2'-pyridyl)-7,8-nido-dicarbaundecaborate tetramethylammonium

Conditions	Yield
With KOH In ethanol in Schlenk flask; soln. of KOH in EtOH was added to borate cluster, mixt. was refluxed for 3 h, cooled to room temp.; mixt. was evapd., residue was dissolved in water and treated with Me4NCl, solid was filtered off, washed with water and Et2O; elem. anal.;	98%

tetramethlyammonium chloride (75-57-0) + 4-hydroxypropiophenone (70-70-2) → 4-Methoxypropiophenone (121-97-1)

Conditions	Yield
With potassium carbonate In 1,2-dimethoxyethane at 145℃; for 0.416667h; Microwave irradiation; Inert atmosphere; Sealed vessel;	98%
With potassium carbonate at 150 - 160℃; for 4h;	81%

tetramethlyammonium chloride (75-57-0) + sodium 2-ethylhexanoic acid → tetramethylammonium 2-ethylhexanoate

Conditions	Yield
In water at 40℃; Flow reactor;	98%

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] (12354-84-6, 12354-85-7) + C20H20FeN3OS(1+)*BF4(1-) + tetramethlyammonium chloride (75-57-0) → C30H34Cl2FeIrN3OS

Conditions	Yield
Stage #1: C20H20FeN3OS(1+)*BF4(1-); tetramethlyammonium chloride With silver(l) oxide In dichloromethane; acetonitrile Molecular sieve; Inert atmosphere; Schlenk technique; Darkness; Stage #2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; Schlenk technique;	98%

dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer + C20H20FeN3OS(1+)*BF4(1-) + tetramethlyammonium chloride (75-57-0) → C30H34Cl2FeN3ORhS

Conditions	Yield
Stage #1: C20H20FeN3OS(1+)*BF4(1-); tetramethlyammonium chloride With silver(l) oxide In dichloromethane; acetonitrile Molecular sieve; Inert atmosphere; Schlenk technique; Darkness; Stage #2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; Schlenk technique;	98%

sodium thiophenolate (930-69-8) + tetramethlyammonium chloride (75-57-0) → methyl-phenyl-thioether (100-68-5)

Conditions	Yield
In methanol at 65℃; for 10h;	97.2%

1,2-dicarba-closo-dodecaborane(12) (16872-09-6) + tetramethlyammonium chloride (75-57-0) → [N(CH3)4][7,10-C2B10H13]

Conditions	Yield
With 1,1-Dibromoethane; magnesium; iodine In tetrahydrofuran to suspn. Mg, I2, and dibromoethane in THF at 0°C soln. o-carborane in THF was added, left at room temp. for 30 min and refluxed for 9 h,mixt. was evapd. to dryness in vacuo, water was added, soln. was filter ed, excess aq. Me4NCl was added; solid was washed with water and Et2O;	97%

propan-1-ol (71-23-8) + tetramethlyammonium chloride (75-57-0) + β-n-butoxycarbonylethyltin trichloride (61470-34-6) → (CH3)4N(1+)*C3H7OCOCH2CH2SnCl4(1-) (78192-82-2)

Conditions	Yield
In methanol; propan-1-ol 1). BuOCOC2H4SnCl3, excess refluxing n-propanol for 4 h; 2). 1 mol Me4NCl in MeOH was added;; solvent was removed; elem. anal.;;	97%

Upstream product

• 67-56-1 methanol 
• 6018-82-2 trimethylvinyl ammonium chloride 
• 74-87-3 methylene chloride 
• 124-40-3 dimethyl amine 
• 60-29-7 diethyl ether 
• 98-09-9 benzenesulfonyl chloride 
• 75-50-3 trimethylamine 
• 77-78-1 dimethyl sulfate 
• 2344-80-1 Chloromethyltrimethylsilane 
• 75-59-2 tetramethyl ammoniumhydroxide 
• 1605-65-8 N,N,N',N'-Tetramethylphosphorodiamidic chloride 
• 122-04-3 4-nitro-benzoyl chloride 
• 63581-76-0 dimethyl-amidophosphoric acid monomethyl ester; tetramethylammonium salt 
• 109-67-1 1-penten 

Downstream Products

• 53663-17-5 tetramethylammonium pentacyanopropenide 
• 75-59-2 tetramethyl ammoniumhydroxide 
• 74-87-3 methylene chloride 
• 75-50-3 trimethylamine 
• 24273-19-6 2,4-dinitrophenyl butanoate 
• 83154-97-6 2,4-Dinitrophenyl monochloroacetateacetate 
• 609-08-5 Diethyl methylmalonate 
• 96750-81-1 2-<4-Chlor-phenylsulfonyl>-1,2-dicyan-aethenol-(1)-at-Tetramethylammonium-Salz 
• 373-68-2 tetramethylammonium fluoride 
• 432-03-1 perfluorotrimethylamine 
• 815-28-1 perfluoro(dimethylethylamine) 
• 73551-02-7 Heptafluorotrimethylamine 
• 73563-15-2 1,1-Difluor-N,N-bis(trifluormethyl)methanamin 
• 574-16-3 (Z)-benzilmonooxime 

Relevant articles and documents

Hydrogen bonded calixarene capsules kinetically stable in DMSO

Half-life times up to 4 days in DMSO at room temperature are observed for the decomposition of dimeric capsules of urea substituted calix[4]arenes held together by a combination of hydrogen bonds, mechanical entanglement and cation-π interactions.

Synthesis and properties of tetraalkylammonium chlorides peroxosolvates (CH3)4NCI·H2O2 and (C 2H5)4NCl·H2O2

Tetraalkylammonium chlorides peroxosolvates (CH3) 4NCl·H2O2 and (C2H 5)4NCl·H2O2 were synthesized. The composition of the solvates was proved by chemical analysis; their X-ray patterns, IR spectra, and thermograms were obtained. The solubility of the solvates in water and their stability in aqueous solutions were investigated.

Pyrolysis Reaction of Carpronium Chloride and its Structurally Realated Compounds. 2-A Mass Spectrometric Study of The Lactonization Mechanism

The mechanism of the pyrolysis reaction of carpronium chloride +-(CH2)3-COOCH3Cl-> leading to γ-butyrolactone and tetramethylammonium chloride was investigated by means of thermal analysis, pyrolysis gas chromatography mass spectrometry and field desorption mass spectrometry, using deuterium labelling.The results indicated that carpronium chloride pyrolysed to yield equimolar amounts of γ-butyrolactone and tetramethylammonium chloride, methyl transfer occured between N and O during the pyrolysis process.The mechanism is discussed on the basis of the experimental results, and with the aid of the theoretical results calculated by the CNDO/2 method.The mechanism presented is as follows. γ-Butyrolactone is formed by the intramolecular migration of the ?-orbital of C=O to the carbon adjacent to + via a 5-membered ring transition state, accompained by a bimolecular reaction between + and the CH3 of O-CH3, resulting in the formation of tetramethylammonium chloride in an amount equimolar with γ-butyrolactone.

Alkylation of ammonium salts catalyzed by imidazolium-based ionic liquid catalysts

Quaternary ammonium salts were synthesized from ammonium salts and dialkyl carbonates over imidazolium ionic liquid catalysts. The reaction gave almost stoichiometric amounts of the quaternary ammonium salts for halides and nitrates. It was found that the electron-donating property of the alkyl moieties of ammonium cations, the electrophilic nature of the alkyl group of the carbonate, the acidity of the acid that the anion of the ammonium salt corresponds to, and the steric hindrance of the ammonium salts and the dialkyl carbonates are the key factors that influence the yields of quaternary ammonium salts. Strong electron-donating alkyl groups on the nitrogen atom of the ammonium salt, electron-withdrawing groups on the methylene carbon of dialkyl carbonate, and weaker steric hindrance of the starting ammonium salts and dialkyl carbonates favor the alkylation reaction of ammonium salts.

Method of hybridizing genes

Provided are a method of hybridizing genes, including applying to a gene microarray a hybridization solution in which a compound represented by formula (1) is added: where each of R1, R2, and R3 is independently a straight or branched C1-C5 alkyl; and X?is an anion of an organic acid; and a method of using a compound represented by formula (1) as an additive to a hybridization solution.

The synthesis of quaternary ammonium salts from ammonium salts and dialkyl carbonate

Quaternary ammonium salts were synthesized from ammonium salts and dialkyl carbonates over an ionic liquid catalyst 1-ethyl-3-methylimidazolium bromide. The Royal Society of Chemistry 2006.

Quinolinium dyes and borates in photopolymerizable compositions

Dye compounds of the formula wherein X is for example CH, C-CH3 or +NOR L-; R is inter alia C1-C6alkyl; R1 is for example C1-C8alkoxy or C1-C12alkyl; s is 0 to 4; R2 is for example hydrogen; Ar is for example a group Y inter alia is C1-C6alkyl or C1-C6alkoxy; r in the formula (A) is 0 to 5, in the formulae (B) and (E) is 0 to 9 and in the formula (D) is 0 to 7; and L is an anion; in combination with an electron donor compound, especially a borate compound, are suitable as photoinitiators for the photopolymerization of radically polymerizable compositions.

Lipopolyamines as transfection agents and pharamaceutical uses thereof

PCT No. PCT/FR95/01595 Sec. 371 Date Jun. 4, 1997 Sec. 102(e) Date Jun. 4, 1997 PCT Filed Dec. 4, 1995 PCT Pub. No. WO96/17823 PCT Pub. Date Jun. 13, 1996Cationic lipids of general formula (I), wherein m is an integer from 2 to 6 inclusive; n is an integer from 1 to 9 inclusive, preferably 1-5, where, when n is 2-9, a single R grouping other than hydrogen is present in the general formula, and m has variable or identical values within the groupings (a) or -(CH2)m; R is a hydrogen atom or a radical of general formula (II), wherein X or X1, which are the same or different, are an oxygen atom, a methylene grouping -(CH2)q- where q is 0, 1, 2 or 3, or an amino grouping -NH- or NR1-, where R is a C1-4 alkyl grouping; Y and Y1, which are the same or different, are a hydrogen atom or an optionally substituted C1-4 alkyl radical, and p is 0-5; and R6 is a cholesterol derivative or an alkylamino grouping -NR1R2, where R1 and R2 are, independently of each other, a straight or branched, saturated or unsaturated C12-22 aliphatic radical. Pharmaceutical compositions containing said lipids, and their uses for transfecting nucleic acids whether in vitro or in vivo in cells, are also disclosed.

Competition between Triborane as a Ligand and a Hybride Donor at Platinum Centres containing Chelating Phosphines: Molecular Structures of PtB3H7>, PtB3H7> and 2>Cl

The reaction of 5-C5H4PPh2)2> with the octahydrotriborate(1-) anion, -, leads to both in which the borane unit acts as a pseudo-bidentate ligand and Cl which results from the borane anion functioning as a hydride donor.For each of the complexes containing a bis(diphenylphosphino)alkane ligand the major product is PtB3H7>, whereas for the reaction of - with 5-C5H4PPh2)2>, 2>Cl is the predominant species formed.Three productshave been structurally characterised: PtB3H7> 1, space group P21/c, a = 16.049(4), b = 15.395(4), c = 21.075(5) Angstroem, β = 90.53(2) deg, Z = 8, R = 0.039; PtB3H7> 3, space group P21, a = 8.8826(18), b = 17.7329(32), c = 9.5520(17) Angstroem, β = 114.115(15) deg, Z = 2, R = 0.032; 2>Cl*3CH2Cl2 6, space group P21/c, a = 12.862(2), b = 38.732(6), c = 14.271(2) Angstroem, β = 99.027(15) deg, Z = 4, R = 0.067.The structure of the cation of 6 resembles that of 2>+ rather than that of t2P(CH2)3PBut2>2>+ thereby indicating that it is the steric bulk of the phosphorus substituents rather than the P-Pt-P bite angle that controls the geometry of the framework and thus the hydride locations.Fenske-Hall molecular orbital calculations have been used to probe the mode of bonding of the hydride ligands to the diplatinum centre.

SYNTHESIS OF ARYLTHALLIUM COMPLEXES USING ORGANOMERCURY COMPOUNDS. CRYSTAL AND MOLEULAR STRUCTURES OF AND

The reaction of or with 2 (1:2) affords or respectively.These two anionic complexes react with NaClO4 to give the neutral compounds and .The crystal structure of shows a distorted trigonal bipyramidal geometry around the thallium atom, if the rather weak interaction between thallium and the farther N atom is included.The nitrogen and carbon atoms occupy axial and equatorial sites, respectively, and a five-memberd TlC2N2 ring is observed.The The Tl-Cl distances are normal, with Tl-Clax longer than Tl-Cleq . the crystal structure of consists of a dimer with two asymmetric chlorine bridges .The chelkating ligand again gives rise to a five-membered ring, here TlC3N.Each thallium atom has a distorted trigonal bipyramidal environment in which the axial positions are occupied by the nitrogen atom of the aryl ligand and the weakly bonded bridging chlorine.The equatorial sites are occupied by the carbon atom of the aryl ligand , the other bridging chlorine, and a terminal chlorine .