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Tetramethyl ammonium chloride
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Name

Tetramethyl ammonium chloride

 EINECS 200-880-8
CAS No. 75-57-0 Density 1.17 g/cm3
PSA 0.00000 LogP -2.67360
Solubility >60 g/100 mL (20 °C ) in water Melting Point >300 °C(lit.)
Formula C4H12NCl Boiling Point 165.26°C (rough estimate)
Molecular Weight 109.599 Flash Point N/A
Transport Information UN 2811 6.1/PG 2 Appearance white crystals
Safety 26-36/37-45-37/39-28A-28-36 Risk Codes 21-25-36/37/38-20/21/22
Molecular Structure Molecular Structure of 75-57-0 (Tetramethylammonium chloride) Hazard Symbols ToxicT, HarmfulXn
Synonyms

Ammonium,tetramethyl-, chloride (8CI);Methanaminium, N,N,N-trimethyl-, chloride (9CI);Tetramethylammonium chloride (6CI);Tetramine chloride;

Article Data 57

Tetramethyl ammonium chloride Synthetic route

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
593-81-7

trimethylamine hydrochloride

616-38-6

carbonic acid dimethyl ester

75-57-0

tetramethlyammonium chloride

Conditions
ConditionsYield
With 1-ethyl-3-methylimidazolium bromide at 169.84℃; for 8h;99%
With 1-ethyl-3-methylimidazolium bromide at 169.84℃; for 8h;
616-38-6

carbonic acid dimethyl ester

75-57-0

tetramethlyammonium chloride

Conditions
ConditionsYield
With ammonium chloride at 169.84℃; for 8h;96%
With ammonium chloride at 169.84℃; for 8h;96%
98-88-4

benzoyl chloride

63581-76-0

dimethyl-amidophosphoric acid monomethyl ester; tetramethylammonium salt

A

75-57-0

tetramethlyammonium chloride

B

106997-48-2

C10H14NO4P

Conditions
ConditionsYield
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)

B

2N(CH3)4(1+)*Hg2Cl6(2-)=[N(CH3)4]2[Hg2Cl6]

C

75-57-0

tetramethlyammonium chloride

Conditions
ConditionsYield
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}

A

(PPh3)3Mo3(μ3-S)(μ2-S)3Cl4

B

75-57-0

tetramethlyammonium chloride

C

3878-45-3

triphenylphosphine sulfide

Conditions
ConditionsYield
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}

A

tetramethylammonium trichloro(2-dimethylaminomethylphenyl-C'N)thallate(III)

B

2N(CH3)4(1+)*Hg2Cl6(2-)=[N(CH3)4]2[Hg2Cl6]

C

75-57-0

tetramethlyammonium chloride

Conditions
ConditionsYield
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
31117-16-5

nido-B10H12CNMe3

7646-69-7

sodium hydride

75-57-0

tetramethlyammonium chloride

Conditions
ConditionsYield
In tetrahydrofuran at 25°C;60%

(Me4N)2{Mo3(μ3-S)(μ2-S2)3Cl6}

A

Mo3(μ3-S)(μ2-S)3(dppe)3Cl4

B

75-57-0

tetramethlyammonium chloride

Conditions
ConditionsYield
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
74-87-3

methylene chloride

105334-48-3

Neopentyl N,N,N',N'-tetramethylphosphorodiamidite

A

75-57-0

tetramethlyammonium chloride

B

Neopentyl N,N-dimethylphosphoramidochloridite

C

bisdimethylamino(methyl)neopentyloxyphosphonium chloride

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

Tetramethyl ammonium chloride Consensus Reports

Reported in EPA TSCA Inventory.

Tetramethyl ammonium chloride Specification

Tetramethyl ammonium chloride, with CAS number of 75-57-0, can be called methanaminium, N,N,N-trimethyl-, chloride (1:1); N,N,N-Trimethylmethanaminium chloride; TMAC. The chemical formula (CH3)4N+Cl- is often abbreviated further as Me4N+Cl-. It is a white crystal. It is a very hygroscopic colourless solid that is soluble in water and polar organic solvents.

Preparation of Tetramethyl ammonium chloride: Tetramethylammonium chloride can be synthesized by the alkylation of ammonium chloride with dimethyl carbonate, in the presence of 1-ethyl-3-methyl imidazolium bromide ([EMIM]+Br-) as an ionic liquid catalyst. The overall reaction is:
NH4+Cl- + 2 (CH3O)2CO → N(CH3)4+Cl- + 2 H2O + 2 CO2

Uses of Tetramethyl ammonium chloride: Tetramethyl ammonium chloride (CAS NO.75-57-0) is used as a phase transfer catalyst for anionic reactants. In small concentrations, also has been shown to enhance yield 5-10 fold at 3M by stabilizing the AT base pairs. Besidea used with polymerase chain reactions to increase yield and specificity.

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing and gloves;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
4. Wear suitable gloves and eye/face protection;
5. After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer);

You can still convert the following datas into molecular structure:
(1)InChI=1S/C4H12N.ClH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1;
(2)InChIKey=OKIZCWYLBDKLSU-UHFFFAOYSA-M;
(3)Smiles[N+](C)(C)(C)C.[ClH-];

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo subcutaneous 2gm/kg (2000mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

CARDIAC: OTHER CHANGES		 Skandinavisches Archiv fuer Physiologie. Vol. 10, Pg. 201, 1900.
guinea pig LDLo unreported 20mg/kg (20mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 7, Pg. 183, 1900.
mouse LD50 intraperitoneal 10mg/kg (10mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) National Technical Information Service. Vol. OTS0536975,
mouse LD50 subcutaneous 40mg/kg (40mg/kg)   National Technical Information Service. Vol. ORNL-5576,
mouse LDLo oral 125mg/kg (125mg/kg)   Journal of Pharmaceutical Sciences. Vol. 69, Pg. 327, 1980.
 
mouse LDLo unreported 20mg/kg (20mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 7, Pg. 183, 1900.
rabbit LDLo subcutaneous 6mg/kg (6mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 7, Pg. 183, 1900.
rat LD50 intraperitoneal 10mg/kg (10mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 National Technical Information Service. Vol. OTS0536975,
rat LD50 oral 50mg/kg (50mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 National Technical Information Service. Vol. OTS0536975,

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