56-37-1

Basic information

• Product Name: Benzyltriethylammonium chloride
• Synonyms: BENZYLTRIETYLAMMONIUM CHLORIDE;BENZYL TRIMETHYL AMMONIUM CHLORIDE (BTMAC50) SURFACTANT;BENZYL TRIMETHYL AMMONIUM CHLORIDE (BTMAC60) SURFACTANT;BENZYLTRIETHYLAMMONIUM CHLORIDE;BTMAC;BTEAC;N,N,N'-TRIETHYLBENZENEMETHANAMINIUM CHLORIDE;N,N,N-TRIETHYL-BENZENEMETHANAMINIUM CHLORIDE
• CAS NO: 56-37-1
• Molecular Formula: C₁₃H₂₂N*Cl
• Molecular Weight: 227.77
• EINECS: 200-300-3
• Product Categories: Pharmaceutical Intermediates;Ammonium Chlorides (Quaternary);Quaternary Ammonium Compounds;Ammonium Salts;Greener Alternatives: Catalysis;Phase Transfer Catalysts;Quaternary ammonium salt;Resin additives
• Mol File: 56-37-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 239 °C (dec.)(lit.)
• Boiling Point: 366.11°C (rough estimate)
• Flash Point: >100°C
• Appearance: White to beige/Liquid
• Density: 1.08 g/mL at 25 °C
• Refractive Index: n20/D 1.479
• Storage Temp.: Store below +30°C.
• Solubility: H2O: 0.1 g/mL, clear
• Water Solubility: 700 g/L (20 ºC)
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 3574984
• CAS DataBase Reference: Benzyltriethylammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyltriethylammonium chloride(56-37-1)
• EPA Substance Registry System: Benzyltriethylammonium chloride(56-37-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39-26 37/39-36/37/39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: BO8400000
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 56-37-1(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder. soluble in water, aqueous solutions conduct electricity. It is hydrochloride salt of benzyltriethylammonium which acts as a phase-transfer catalyst in chemical reactions.

Uses

Benzyltriethylammonium chloride is used as a catalyst in the preparation of 2-phenylbutyronitrile from phenyl acetonitrile. It is involved in the Knoevenagel condensation of carbonyl compounds with active methylene compounds to give olefinic products. It acts as a phase transfer catalyst used in the alkylation reaction. It reacts with 1H-Pyridine-2-thione to get 2-Benzylsulfanyl-pyridine.

Application

Benzyltriethylammonium chloride is a lipophilic phase-transfer catalyst that can be used in phase-transfer catalysis (PTC) to catalyze polycondensation reactions to form high molecular weight polymers under bi-phasic conditions.It can also be used:To activate hydroxyapatite and natural phosphate for use as a solid support for Knoevenagel condensation and Claisen-Schmidt condensation, respectively at room temperature and in the absence of a solvent.To increase the efficiency of mCPBA oxidation of sulfonimine generated from arenesulfonamide and diethyl acetal of an aromatic aldehyde to form 2-sulfonyloxaziridines.In combination with antimony(V) chloride to form a catalytic system for the Friedel-Crafts acylation reactions of arenes with acyl and sulfonyl chlorides.

Preparation

Benzyltriethylammonium chloride synthesis: Add benzyl chloride, triethylamine and acetone into the reaction pot, and reflux at 63-64°C for 8 hours. Slowly lowered to 15°C, filtered, and the filter cake was washed with acetone and dried to obtain benzyltriethylammonium chloride. Yield 68.9%.

Safety Profile

Poison by intravenous route.When heated to decomposition it emits toxic vapors ofNOx and Cl.

InChI:InChI=1/C13H22N.ClH/c1-4-14(5-2,6-3)12-13-10-8-7-9-11-13;/h7-11H,4-6,12H2,1-3H3;1H/q+1;/p-1

Synthetic route

benzyl chloride (100-44-7) + triethylamine (121-44-8) → N-benzyl-N,N,N-triethylammonium chloride (56-37-1)

Conditions	Yield
at 20℃;	100%
In acetonitrile for 1h; Reflux;	95%
	75%

DBC (3459-92-5) + triethylamine hydrochloride (554-68-7) → N-benzyl-N,N,N-triethylammonium chloride (56-37-1)

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

benzyl chloride (100-44-7) → N-benzyl-N,N,N-triethylammonium chloride (56-37-1)

Conditions	Yield
In polydimethylsiloxane	76.3%

benzyl chloride (100-44-7) + triethylamine (121-44-8) → N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7)

Conditions	Yield
2 In acetonitrile for 24h; Product distribution; Irradiation; 1-bromopentane as other substrate; various photocatalysts;	A 70% B 22%

triethylbenzylammonium 2,4-dinitrophenolate (138554-42-4) → N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + 1,2,3,4,6-Pentachloro-5-(2,4-dinitro-phenoxy)-[1,3,5,2,4,6]triazatriphosphinane

Conditions	Yield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In chloroform at 24.9℃; Rate constant; var. solvents;

triethylbenzylammonium 2,4-dinitrophenolate (138554-42-4) → N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + 1,2,3,4,5,6,8-Heptachloro-7-(2,4-dinitro-phenoxy)-[1,3,5,7,2,4,6,8]tetrazatetraphosphocane

Conditions	Yield
With octachlorocyclotetraphosphazene In chloroform at 24.9℃; Rate constant; var. solvents;

triethylbenzylammonium 2,4-dinitrophenolate (138554-42-4) → N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + 2,2,4,4,6-Pentachloro-6-(2,4-dinitro-phenoxy)-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinine (157033-41-5)

Conditions	Yield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; 4-nitro-phenol; buffer pH 9.18 In chlorobenzene at 24.9℃; Rate constant; Equilibrium constant; Mechanism; other proton donors, var. pH;

4-Nitro-phenolatebenzyl-triethyl-ammonium; (138554-40-2) → N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + 1,2,3,4,6-Pentachloro-5-(4-nitro-phenoxy)-[1,3,5,2,4,6]triazatriphosphinane

Conditions	Yield
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine In chloroform at 24.9℃; Rate constant; Mechanism; var. solvents, other phenols and cyclophosphazenes;

triethylbenzylammonium diiodochloride → N-benzyl-N,N,N-triethylammonium chloride (56-37-1)

Conditions	Yield
In chloroform Equilibrium constant;

dichloro(bis(2-isopropylamino-4-methoxyphenyl)amine(-3H))tantalum(V) (1133239-24-3) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → C20H26Cl3N3O2Ta(1-)*C13H22N(1+)

Conditions	Yield
In tetrahydrofuran for 12h; Inert atmosphere;	99%

C18H20Cl2F2N3Ta*0.5C7H8 + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → C18H20Cl3F2N3Ta(1-)*C13H22N(1+)

Conditions	Yield
In tetrahydrofuran for 12h; Inert atmosphere;	99%

C18H22Cl2N3Ta + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → C18H22Cl3N3Ta(1-)*C13H22N(1+)

Conditions	Yield
In tetrahydrofuran for 12h; Inert atmosphere;	99%

C20H26Cl2N3Ta + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → C20H26Cl3N3Ta(1-)*C13H22N(1+)

Conditions	Yield
In tetrahydrofuran for 12h; Inert atmosphere;	99%

C26H38Cl2N3Ta + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → C26H38Cl3N3Ta(1-)*C13H22N(1+)

Conditions	Yield
In tetrahydrofuran for 12h; Inert atmosphere;	99%

octadecane-1,18-dicarboxylic acid (2424-92-2) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + epichlorohydrin (106-89-8) → octadecane-1,18-dicarboxylic acid glycidyl ester + octadecane-1,18-dicarboxylic acid diglycidyl ester

Conditions	Yield
With sodium hydroxide	A 98.4% B n/a

tris(pentafluoroethyl)difluorophosphorane (91543-32-7) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → benzyltriethylammonium tris(pentafluoroethyl)difluorochlorophosphate (1042169-47-0)

Conditions	Yield
In acetonitrile at 20℃; for 1h;	98.2%

N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → benzyltriethylammonium borohydride

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 1.5h;	98%

phenyl(1H-pyrrol-2-yl)methanone (7697-46-3) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → (1-benzyl-1H-pyrrol-2-yl)(phenyl)methanone

Conditions	Yield
With sodium hydroxide In water; toluene for 2h; Reflux; chemoselective reaction;	98%

acetylacetonatodicarbonylrhodium(l) + triphenyl-arsane (603-32-7) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → 3(C6H5CH2N(C2H5)3)(1+)*(Rh10As(CO)22)(3-)*OC4H8=(C6H5CH2N(C2H5)3)3(Rh10As(CO)22)*OC4H8 (75802-04-9)

Conditions	Yield
With cesium benzoate trihydrate; cesium borohydride; carbon monoxide In isopropyl alcohol; acetone High Pressure; to Rh(CO)2acac, PhCOOCs*3H2O, AsPh3 and CsBH4 mixed in tetraglyme and soln. stirred under 6000 psi CO-H2 at 150°C for 2 h, mixt. filtered, toluene added, oil dissolved in acetone, (PhCH2NEt3)Cl in 2-propanoladded; ppt. filtered, washed with 2-propanol and vac.-dried; elem. anal.;	97.8%

N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → benzyltriethylammonium chloride aluminium chloride

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 5 - 20℃; for 12.5h; Inert atmosphere;	97%

germanium(II) chloride dioxane + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → benzyltriethylammonium trichlorogermanate(II) (208348-62-3)

Conditions	Yield
In tetralin byproducts: dioxane; (N2); stirring (70°C, 15 min); removal of volatiles (vac., room temp., 12 h), filtration at -20°C, washing (pentane), drying (vac.); elem. anal.;	96.7%

dichloromethane (75-09-2) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + 7-O-sec-butyl-6-hydroxy-2,2-dimethyl-4-chromanone (125627-85-2) → 7-O-sec-butyl-6-methoxy-2,2-dimethyl-4-chromanone (125627-93-2)

Conditions	Yield
In sodium hydroxide; water	96%

N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + tungsten(IV) chloride (13470-13-8) → C6H5CH2N(C2H5)3(1+)*WCl6(1-)=C6H5CH2N(C2H5)3WCl6 (215669-98-0) + 2C6H5CH2N(C2H5)3(1+)*W2Cl9(2-)=[C6H5CH2N(C2H5)3]2W2Cl9

Conditions	Yield
In dichloromethane react. for several days at 25°C, filtration, washing (CH2Cl2), drying (vac.), cooling of supenatant and crystn. of WCl6-salt; elem. anal.;	A 37% B 96%

3,5-bis(2-methoxyphenyl)-1H-pyrazole (1159937-12-8) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + potassium carbonate (584-08-7) + potassium hydroxide → bis(3,5-bis(2-methoxyphenyl)-1H-pyrazol-1-yl)methane (1227401-55-9)

Conditions	Yield
In dichloromethane for 12h; Reflux;	96%

[(cyclopentadienyl)Ru(η6-naphthalene)]BF4 (100506-76-1) + tert-butylisonitrile (119072-55-8, 7188-38-7) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → C15H23ClN2Ru

Conditions	Yield
In dichloromethane for 12h; Inert atmosphere;	96%

N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + sodium di(1,1,3-trihydrotetrafluoropropyl) sulfosuccinate (62635-69-2) → 1,2-Bis-(2,2,3,3-tetrafluoro-propoxycarbonyl)-ethanesulfonatebenzyl-triethyl-ammonium; (80563-71-9)

Conditions	Yield
In ethanol at 75 - 80℃;	95.1%
In ethanol at 78℃; for 2h;

N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + sodium ethanolate (141-52-6) → triethylbenzylammonium ethanolate (95903-96-1)

Conditions	Yield
at 5℃; for 12h;	95%
In ethanol Ambient temperature;

N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → phenylacetic acid (103-82-2)

Conditions	Yield
With sodium hydroxide; Co(CO)8; methyl iodide In benzene Mechanism; Ambient temperature; other quaternaryammonium salts;	95%

N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → triethylbenzylammonium iodide (5400-94-2)

Conditions	Yield
With trimethylsilyl iodide In acetonitrile for 0.5h; Heating;	95%

closo-3-I-2,4-C2B5H6 (98821-58-0) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → 3-Cl-closo-2,4-C2B5H6 (28347-93-5)

Conditions	Yield
With trimethylamine In dichloromethane-d2 allowing to stand at room temp., 43d; monitoring by 11B NMR;	95%
In dichloromethane allowing to stand at room temp., 9d; monitoring by 11B NMR;	78%

(2-methylallyl)palladium-chloride dimer + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → (C2H5)3N(CH2C6H5)(1+)*PdCl2(C3H4CH3)(1-)=(C2H5)3N(CH2C6H5)[PdCl2(C3H4CH3)] (76096-87-2)

Conditions	Yield
In dichloromethane soln. of Pd complex treated with anhydrous NEt3(CH2Ph)Cl; concd., added to excess Et2O, crystd. on stirring, recrystd. from CH2Cl2-Et2O; elem. anal.;	95%

dichloromethane (75-09-2) + (BnEt3N)[W2(μ-Cl)3Cl6] (215669-96-8) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → 2C6H5CH2N(C2H5)3(1+)*W2Cl10(2-)*CH2Cl2=[C6H5CH2N(C2H5)3]2W2Cl10*CH2Cl2

Conditions	Yield
In dichloromethane at -30°C for 1 day, filtration, washing, drying; elem. anal.;	95%

[(C4Et4)Rh(p-xylene)]+PF6 + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → C12H20ClRh

Conditions	Yield
In dichloromethane for 24h; Inert atmosphere;	95%

7-hydroxy-2,2-dimethyl-chroman-4-one (17771-33-4) + dichloromethane (75-09-2) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → 7-methoxy-2,2-dimethyl-4-chromanone (20321-73-7)

Conditions	Yield
In sodium hydroxide; water	94.6%

C6H5CH2N(C2H5)3(1+)*WCl6(1-)=C6H5CH2N(C2H5)3WCl6 (215669-98-0) + 2C6H5CH2N(C2H5)3(1+)*W2Cl9(2-)=[C6H5CH2N(C2H5)3]2W2Cl9 + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → 2C6H5CH2N(C2H5)3(1+)*WCl6(2-)=[C6H5CH2N(C2H5)3]2WCl6

Conditions	Yield
In not given	94%

thionyl chloride (7719-09-7) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + hafnium tetrachloride (13499-05-3) + titanium(III) chloride (7705-07-9) → di[triethylbenzylammonium] decachloridohafnatetitanate

Conditions	Yield
In neat (no solvent) (Ar), HfCl4, TiCl3, (Et3NBz)Cl (1:1:2) treated dropwise under stirring with SOCl2, refluxed for 1 h, cooled to room temp., stirred for 2 h; concd.(vac.), pptd.(pentane), filtered, washed (pentane), dried (vac.) for 2 h, elem. anal.;	94%

thionyl chloride (7719-09-7) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + hafnium tetrachloride (13499-05-3) → di[triethylbenzylammonium] decachloridodihafnate

Conditions	Yield
In neat (no solvent) (Ar), HfCl4 and (Et3NBz)Cl(1:1) treated dropwise under stirring with SOCl2, heated to 65°C for 1 h, cooled to room temp., stirred for 1 h; pptd.(pentane), filtered, washed (pentane), dried (vac.) overnight, elem. anal.;	94%

Upstream product

• 100-44-7 benzyl chloride 
• 121-44-8 triethylamine 
• 3459-92-5 DBC 
• 554-68-7 triethylamine hydrochloride 
• 138554-40-2 4-Nitro-phenolatebenzyl-triethyl-ammonium; 
• 138554-42-4 triethylbenzylammonium 2,4-dinitrophenoxide 

Downstream Products

• 1836-42-6 benzyltriethylammonium hydroxide 
• 100-44-7 benzyl chloride 
• 121-44-8 triethylamine 
• 63348-55-0 benzyl N-methyl-2-imidazolyl sulfide 
• 716-79-0 2-phenyl-1H-benzoimidazole 
• 18670-23-0 β,β-dimethyl-α-phenylacrylonitrile 
• 1689-71-0 2,3-diphenyloxirane 
• 14289-44-2 (RS)-2-naphthylglycolic acid 
• 65148-70-1 3-methylmandelic acid 
• 16273-37-3 3-chloromandelic acid 
• 103317-61-9 4-chloro-α-(2-chloro-4-nitrophenyl)-α-methyl-3-(trifluoromethyl)benzeneacetonitrile 
• 12244-83-6 (C₅H₅)Mo(CO)3CH₂Cl 
• 77933-22-3 C₆H₅CH₂N(C₂H₅)3⁽¹⁺⁾*C₅H₅Mo(CO)3^(1-) 
• 82124-96-7 N-benzyl-N,N-diethylethanaminium hexafluorophosphate(V) 

Relevant articles and documents

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Thermal stability of quaternary ammonium hexafluorophosphates and halides

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Distribution of the products of benzhydryl bromide heterolysis in the presence of triphenylverdazyl in aprotic solvents

The distribution of products of benzhydryl bromide heterolysis in the presence of triphenylverdazyl in anhydrous nitrobenzene and propylene carbonate, as well as in anhydrous acetonitrile in the presence of benzyltriethylammonium chloride was studied. In kinetic experiments the contribution of verdazyl alkylation was always minor, and verdazyl was mostly consumed in the reaction with HBr evolved during solvolysis. Thus, triphenylverdazyl is not an indicator of the solvent-separated ion pair of benzhydryl bromide. Pleiades Publishing, Inc., 2006.