56-93-9

Basic information

• Product Name: Benzyltrimethylammonium chloride
• Synonyms: Benzenemethanaminium,N,N,N-trimethyl-,chloride;benzyltrimethyl-ammoniuchloride;Benzyltrimethylammoniumchlori;n,n,n-trimethyl-benzenemethanaminiuchloride;BTM;N,N,N-Trimethylbenzenemethanaminium chloride;TMBAC;(+)-Benzotetramisole
• CAS NO: 56-93-9
• Molecular Formula: C₁₀H₁₆N*Cl
• Molecular Weight: 185.69
• EINECS: 200-300-3
• Product Categories: Organics;Phenyls & Phenyl-Het;Ammonium Chlorides (Quaternary);Quaternary Ammonium Compounds;Asymmetric Synthesis;Synthetic Organic Chemistry;Phenyls & Phenyl-Het;Ammonium Salts;Greener Alternatives: Catalysis;Phase Transfer Catalysts;Quaternary ammonium salt;intermediates;Pharmaceutical Intermediates
• Mol File: 56-93-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 239 °C (dec.)(lit.)
• Boiling Point: 305.52°C (rough estimate)
• Appearance: White to ivory/Crystalline Powder or Chunks
• Density: 1.08 g/mL at 25 °C
• Vapor Pressure: <0.0001 hPa (20 °C)
• Refractive Index: n20/D 1.479
• Storage Temp.: Store below +30°C.
• Solubility: 800g/l
• Water Solubility: 800 g/L
• Sensitive: Hygroscopic
• Stability: Stable. Hygroscopic. Incompatible with strong oxidizing agents.
• BRN: 3917255
• CAS DataBase Reference: Benzyltrimethylammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyltrimethylammonium chloride(56-93-9)
• EPA Substance Registry System: Benzyltrimethylammonium chloride(56-93-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/38-36
• Safety Statements: 26-37/39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: BO8400000
• F: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 56-93-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 56-93-9 differently. You can refer to the following data:
1. Solvent for cellulose, gelling inhibitor in polyester resins, intermediate.
2. Benzyltrimethylammonium chloride are Ccommercially important catalyst. Used in antistatic agent, detergent Sanitisers, softner for textiles and paper products, phase transfer catalyst.

General Description

Light yellow liquid with a mild almond odor. May float or sink in water.

Air & Water Reactions

Water soluble.

Reactivity Profile

Benzyltrimethylammonium chloride can react with oxidizing materials . Toxic oxides of nitrogen and hydrochloric acid fumes may form in fire [USCG, 1999].

Health Hazard

Ingestion causes gastrointestinal disturbances. Contact with liquid irritates eyes and may irritate skin.

Fire Hazard

Special Hazards of Combustion Products: Toxic oxides of nitrogen and hydrochloric acid fumes may form in fire.

Safety Profile

Poison by ingestion. Combustible.When heated to decomposition it emits very toxic fumesof NH3, NOx, and Cl??.

Purification Methods

A 60% aqueous solution of the salt is evaporated to dryness under a vacuum on a steam bath, and then left in a vacuum desiccator containing a suitable drying agent. The solid residue is dissolved in a small volume of boiling absolute EtOH and precipitated by adding an equal volume of diethyl ether with cooling. After washing, the precipitate is dried under a vacuum [Karusch J Am Chem Soc 73 1246 1951]. [Beilstein 12 IV 2162.]

InChI:InChI=1/C10H16N.ClH/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H/q+1;/p-1

Synthetic route

benzyl bromide (100-39-0) + trimethylamine (75-50-3) → benzyltrimethylammonium chloride (56-93-9)

Conditions	Yield
In ethanol; acetone Alkylation;	95%

benzyl chloride (100-44-7) + trimethylamine (75-50-3) → benzyltrimethylammonium chloride (56-93-9)

Conditions	Yield
In diethyl ether; water Ambient temperature;	94%
With methanol
With ethanol

benzyltrismethylammonium methoxide (122-08-7) → benzyltrimethylammonium chloride (56-93-9)

Conditions	Yield
With hydrogenchloride In methanol at 0℃; for 0.5h;	73%

DBC (3459-92-5) + trimethylamine hydrochloride (593-81-7) → benzyltrimethylammonium chloride (56-93-9)

Conditions	Yield
With 1-ethyl-3-methylimidazolium bromide at 169.84℃; for 8h;	71.3%

C29H38N6O4*C10H16N(1+)*Cl(1-) → benzyltrimethylammonium chloride (56-93-9) + Trp-Aib-Gly-Leu-NHPh (232279-44-6)

Conditions	Yield
In chloroform-d1 at 24.84℃; Equilibrium constant; complex formation;

C31H42N6O4*C10H16N(1+)*Cl(1-) → benzyltrimethylammonium chloride (56-93-9) + Trp-Aib-Gly-Leu-NH-C6H3(3,5-Me2) (271770-12-8)

Conditions	Yield
In chloroform-d1 at 24.84℃; Equilibrium constant; complex formation;

trimethylbenzylammonium diiodochloride → benzyltrimethylammonium chloride (56-93-9)

Conditions	Yield
In chloroform Equilibrium constant;

benzylamine (100-46-9) + methyl iodide (74-88-4) → benzyltrimethylammonium chloride (56-93-9) + benzyl-methyl-amine (103-67-3)

Conditions	Yield
Stage #1: benzylamine; methyl iodide With 1,1,1,3',3',3'-hexafluoro-propanol In d(4)-methanol at 20℃; for 1h; Stage #2: With hydrogenchloride In water for 1h; Reagent/catalyst; Time;

benzyl bromide (100-39-0) → benzyltrimethylammonium chloride (56-93-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile / 12 h / 50 °C 2: Dowex 22 chloride form / acetonitrile View Scheme

trimethylbenzylammonium bromide (5350-41-4) → benzyltrimethylammonium chloride (56-93-9)

Conditions	Yield
With Dowex 22 chloride form In acetonitrile	108 mg

tributylphosphine (998-40-3) + benzyltrimethylammonium chloride (56-93-9) → tributylbenzylphosphonium chloride (1224-56-2)

Conditions	Yield
at 100℃; for 0.166667h; Irradiation;	100%

silver tetrafluoroborate (14104-20-2) + iron(II) octaethyltetraazaporphyrin (169697-22-7) + benzyltrimethylammonium chloride (56-93-9) → chloroiron(III) 2,3,7,8,12,13,17,18-octaethyl-5,10,15,20-tetraazaporphyrinate (141045-99-0)

Conditions	Yield
In dichloromethane; toluene byproducts: Ag; inert atmosphere; addn. of AgBF4 to the Fe-complex in toluene; stirred for 30 min; filtration off of Ag (Celite), evapn. (vac.), dissoln. in CH2Cl2, addn. of PhCH2N(CH3)3Cl, stirring (15 min);; filtration (Celite), partial evapn. (vac.), crystn. (hexane/C6H6, slow evapn.);;	100%

Mo(allyl)(carbonyl)2(acetonitrile)2(bromide) + Na2[7,8-Ph2-7,8-nido-C2B9H9] + benzyltrimethylammonium chloride (56-93-9) → C6H5CH2N(CH3)3(1+)*(CO)2(C3H5)MoC2B9H9(C6H5)2(1-)=[C6H5CH2N(CH3)3][(CO)2(C3H5)MoC2B9H9(C6H5)2] (189502-86-1)

Conditions	Yield
In tetrahydrofuran refluxing equimolar amts. of carborane and No-complex, solvent removal (vac.), dissoln. in CH2Cl2, addn. of BzNMe3Cl; trituration with pentane;	99%

benzyltrimethylammonium chloride (56-93-9) + rac-Potassium mandelate (84864-61-9) → benzyltrimethylammonium mandelate

Conditions	Yield
In water at 60℃; for 6h;	99%

2-(2,4,6-trichloro-phenoxy)-ethanol (6161-87-1) + benzyltrimethylammonium chloride (56-93-9) → 2-(2,4,6-trichlorophenoxy)-ethyl chloride (13001-29-1)

Conditions	Yield
With thionyl chloride In tetrachloromethane; water	98%

sodium tungstate (VI) dihydrate (10213-10-2) + 2-nitrophenylphenyl sulfide + benzyltrimethylammonium chloride (56-93-9) → 2-nitrophenylphenyl sulfone

Conditions	Yield
With sulfuric acid; dihydrogen peroxide In toluene	97.6%

Methyl formate (107-31-3) + benzyltrimethylammonium chloride (56-93-9) + 4-Methylbenzyl chloride (104-82-5) → 4-methylbenzyl formate

Conditions	Yield
With sodium formate	97%

benzyltrimethylammonium chloride (56-93-9) → N,N,N-trimethylbenzenemethanaminium dichloroiodate (114971-52-7)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; iodine In water; acetonitrile at 20℃; Cooling with ice;	96%
With Iodine monochloride In dichloromethane; water for 0.5h; Ambient temperature;	86%
With Iodine monochloride In dichloromethane; water for 0.5h; Ambient temperature;	86%
With Iodine monochloride In dichloromethane; water at 20℃; for 0.666667h;

benzyltrimethylammonium chloride (56-93-9) → benzyltrimethylazanium tetrachloro-λ3-iodanuide (121309-88-4)

Conditions	Yield
With iodine trichloride In dichloromethane for 0.5h; Ambient temperature;	96%

iron pentacarbonyl (13463-40-6) + potassium tellurite monohydrate + benzyltrimethylammonium chloride (56-93-9) → 2C6H5CH2N(CH3)3(1+)*Te6Fe8(CO)24(2-)=(C6H5CH2N(CH3)3)2[Te6Fe8(CO)24]

Conditions	Yield
With KOH In methanol; water N2-atmosphere; addn. of Te-salt in water to Fe(CO)5 in 50 % KOH (aq.) and MeOH; stirring (2 h, room temp.); filtration; dropwise addn. of ammonium salt in water (pptn.); filtration; washing (water); drying (vac.); recrystn. (CH2Cl2); elem. anal.;	96%

potassium 1,2-cyclobutane-3,4-dithiolate (52427-61-9) + indium(III) chloride (10025-82-8) + benzyltrimethylammonium chloride (56-93-9) → tris(benzyltrimethylammonium) [tris(1,2-dithioquadratato-S,S')indate(III)]

Conditions	Yield
In water 3-3 equiv. of K-salt and N-compd. were dissolved in H2O, 1 equiv. of InCl3 was slowly added in H2O; ppt. was filtered off, dried in an exsiccator, elem. anal.;	96%

BF4(1-)*C26H21MnO2P(1+)*0.25CH2Cl2 + benzyltrimethylammonium chloride (56-93-9) → C26H33ClMnO2P

Conditions	Yield
In dichloromethane Inert atmosphere; Schlenk technique;	96%

benzyltrimethylammonium chloride (56-93-9) → benzyltrimethylazanium tribroman-2-uide

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; potassium bromide; molybdic acid In water at 0 - 20℃; for 0.916667h;	95.25%
With sodium bromate; hydrogen bromide In dichloromethane; water for 0.25h;	85%
With sodium bromate; hydrogen bromide In water Ambient temperature;	78%

benzyltrimethylammonium chloride (56-93-9) → benzyltrimethylammonium tribromide

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; potassium bromide; molybdic acid In water at 0 - 20℃; for 0.916667h; Product distribution / selectivity;	95.25%

benzyltrimethylammonium chloride (56-93-9) + triphenylphosphine (603-35-0) → benzyltriphenylphosphonium chloride (1100-88-5)

Conditions	Yield
at 250℃; for 0.166667h; Irradiation;	95%

benzyltrimethylammonium chloride (56-93-9) + bis<3-<3-(3-hydroxypropyl)-1,1,3,3-tetramethyldisiloxanyl>propyl> sulfosuccinate sodium salt (70857-63-5) → bis<3-<3-(3-hydroxypropyl)-1,1,3,3-tetramethyldisiloxanyl>propyl> sulfosuccinate trimethylbenzylammonium salt (82803-88-1)

Conditions	Yield
In ethanol at 80℃; for 6h;	94.8%

potassium selenite + iron pentacarbonyl (13463-40-6) + benzyltrimethylammonium chloride (56-93-9) → 2C6H5CH2N(CH3)3(1+)*Se6Fe6(CO)12(2-)=[C6H5CH2N(CH3)3]2[Se6Fe6(CO)12]

Conditions	Yield
With KOH In methanol N2-atmosphere; addn. of 1 equiv. of solid K2SeO3 to equimolar amt. Fe(CO)5 in MeOH (contg. excess KOH), prolonged stirring (observation of intermediates), filtration, dropwise addn. of excess aq. PhCH2NMe3Cl to filtrate (pptn.); collection (filtration), washing (water), drying (vac.), recrystn. (THF/ether); elem. anal.;	94%
With KOH In methanol; water N2-atmosphere; addn. of 1 equiv. aq. K2SeO3 to equimolar amt. Fe(CO)5 in MeOH (contg. excess KOH), stirring for 5 h (room temp.), filtration, dropwise addn. of excess aq. PhCH2NMe3Cl to filtrate (pptn.); collection (filtration), washing (water), drying (vac.), recrystn. (THF/ether); elem. anal.;	94%

benzyltrimethylammonium chloride (56-93-9) + sodium di(1,1,3-trihydrotetrafluoropropyl) sulfosuccinate (62635-69-2) → trimethylbenzylammonium salt of di(1,1,3-trihydrotetrafluoropropyl) sulfosuccinate

Conditions	Yield
In ethanol at 75 - 80℃; for 2h;	92.8%

1,4-dihydroxybut-2-yne (110-65-6) + benzyltrimethylammonium chloride (56-93-9) + 3-chloroprop-1-ene (107-05-1) → 1,4-bis(allyloxy)-2-butyne (90925-51-2)

Conditions	Yield
With sodium hydroxide In water	92%

Methyl formate (107-31-3) + 1,4-bis(chloromethyl)-2,5-dichlorobenzene (50987-90-1) + benzyltrimethylammonium chloride (56-93-9) → 2,5-dichlorobenzene-1,4-dimethanol (2800-99-9)

Conditions	Yield
With sodium formate In methanol; sodium methylate	92%

benzyltrimethylammonium chloride (56-93-9) + 3-nitro-5-trifluoromethylpyridin-2-ol (33252-64-1) → 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (72587-15-6)

Conditions	Yield
With trichlorophosphate In acetonitrile for 3h; Heating;	92%

benzyltrimethylammonium chloride (56-93-9) → benzyltrimethylammonium dibromoiodate(I) (1413396-80-1)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; iodine In water; acetonitrile at 20℃; Cooling with ice;	92%

4-methoxyphenylboronic acid (5720-07-0) + benzyltrimethylammonium chloride (56-93-9) → p-benzylanizole (834-14-0)

Conditions	Yield
With potassium phosphate; (NC5H3(N2C7H4(CH2)3CH3)2)NiBr(1+)*Br(1-)=Ni(NC5H3(N2C7H4(CH2)3CH3)2)Br2; triphenylphosphine In 1,4-dioxane at 80℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique;	92%
With potassium phosphate; palladium diacetate; XPhos In tetrahydrofuran at 50℃; for 14h; Sealed tube; Inert atmosphere;	80%

iron pentacarbonyl (13463-40-6) + benzyltrimethylammonium chloride (56-93-9) + sulfur (7704-34-9) + iron(II) chloride → (BTMA)2[Fe4S4Cl4]

Conditions	Yield
In acetonitrile for 72h; Inert atmosphere; Schlenk technique; Reflux;	91%

benzyltrimethylammonium chloride (56-93-9) + sodium bis(2,2,3,3,4,4,5,5-octafluoro-1-pentyl) sulfosuccinate (62607-32-3) → 1,2-Bis-(2,2,3,3,4,4,5,5-octafluoro-pentyloxycarbonyl)-ethanesulfonatebenzyl-trimethyl-ammonium; (80556-00-9)

Conditions	Yield
In ethanol at 75 - 80℃;	90%
In ethanol at 78℃; for 2h;

Trifluoromethanesulfonamide (421-85-2) + 2-(1-naphthyloxy)-1-ethanol (711-82-0) + benzyltrimethylammonium chloride (56-93-9) → C13H11F3NO6S2(1-)*C10H16N(1+)

Conditions	Yield
Stage #1: Trifluoromethanesulfonamide With pyridine; sulfuryl dichloride In acetonitrile at 20℃; for 1.5h; Cooling with ice; Stage #2: 2-(1-naphthyloxy)-1-ethanol With dmap In acetonitrile at 50 - 80℃; for 24h; Cooling with ice; Stage #3: benzyltrimethylammonium chloride In methanol; water; acetonitrile for 0.5h;	90%

benzyltrimethylammonium chloride (56-93-9) + Diphenylphosphine oxide (4559-70-0) → benzyldiphenylphosphine oxide (2959-74-2)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate at 60℃; for 3h; Schlenk technique; Inert atmosphere;	90%
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; caesium carbonate In acetonitrile at 100℃; for 18h; Schlenk technique; Inert atmosphere;	67%

6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonyl-3,3,5,8-tetramethylthiochroman-4-one-1,1-dioxide + n-propanesulfonyl chloride (10147-36-1) + benzyltrimethylammonium chloride (56-93-9) → 6-(1-Ethyl-5-n-propanesulfonyloxypyrazol-4-yl)carbonyl-3,3,5,8-tetramethylthiochroman-4-one-1,1-dioxide (189206-85-7)

Conditions	Yield
With potassium carbonate In dichloromethane; water	89%

Upstream product

• 100-44-7 benzyl chloride 
• 75-50-3 trimethylamine 
• 5350-41-4 trimethylbenzylammonium bromide 
• 100-39-0 benzyl bromide 
• 3459-92-5 DBC 
• 593-81-7 trimethylamine hydrochloride 
• 122-08-7 benzyltrismethylammonium methoxide 
• 100-46-9 benzylamine 
• 74-88-4 methyl iodide 

Downstream Products

• 162401-70-9 4-(difluoromethoxy)-3-methoxybenzaldehyde 
• 40591-14-8 benzyl-(1-methyl-prop-2-ynyl)-amine; hydrochloride 
• 138383-16-1 (3R,4S-cis)-1,3,4,5-tetrahydro-6-(trifluoromethyl)-3-hydroxy-1-<2-(dimethylamino)ethyl>-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one monohydrochloride 
• 78107-85-4 4,6-Dichloro-3-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride 
• 141060-78-8 6-benzenesulfonyl-2H-pyridazin-3-one 
• 99686-44-9 2[(CH₃)3CH₂C₆H₅N]⁽¹⁺⁾*Na⁽¹⁺⁾*[Cu₃(S₂C₂H₄)3]^(3-)*CH₃OH=[(CH₃)3CH₂C₆H₅N]2Na[Cu₃(S₂C₂H₄)3]*CH₃OH 
• 13463-40-6 iron pentacarbonyl 

Relevant articles and documents

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