554-68-7

Basic information

• Product Name: Triethylamine hydrochloride
• Synonyms: Tolzaoline bydrochloride;TriethylamineHydrochloride,>99%;Triethylaminehydrochloride,98%;Triethylammoniumchlorid;Et3·HCl;Triethylamine hydroc;TriethylaMine hydrochloride, 99+% 1KG;TriethylaMine hydrochloride, 99+% 250GR
• CAS NO: 554-68-7
• Molecular Formula: C₆H₁₆N*Cl
• Molecular Weight: 137.65
• EINECS: 209-067-2
• Product Categories: HPLC;HPLC Buffer;HPLC Buffers;HPLC Buffers - SolutionChromatography/CE Reagents;Solution
• Mol File: 554-68-7.mol
• Article Data: 351

Chemical Properties

• Melting Point: 261 °C (dec.)(lit.)
• Boiling Point: 223.18°C (rough estimate)
• Flash Point: 39 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.07
• Vapor Pressure: 56.1mmHg at 25°C
• Refractive Index: 1.4530 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 1440 g/L (20°C)
• Water Solubility: 1440 g/L (20 ºC)
• Sensitive: Hygroscopic
• Merck: 14,9666
• BRN: 3906409
• CAS DataBase Reference: Triethylamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Triethylamine hydrochloride(554-68-7)
• EPA Substance Registry System: Triethylamine hydrochloride(554-68-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22
• WGK Germany: 1
• RTECS: YE2111500
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 554-68-7(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white crystalline powder

Uses

Triethylamine Hydrochloride is a hydrochloride salt of triethyllamine (T775740). Triethylamine is used as a competing base for the separation of acidic basic and neutral drugs by reverse-phased high-performance liquid chromatography (HPLC). Triethylamine induces visual disturbances (such as foggy vision) in humans, and is also used in industry as a quenching agent in the ozonolysis of alkenes (e.g. (E)-2-Pentene [P227315]). Triethylamine is used in the purification of drugs which are pharmacologically or chemically similar through separation in reverse-phase HPLC (2).Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA). Environmental contaminants; Food contaminants.

Safety Profile

Moderately toxic by subcutaneousroute. When heated to decomposition it emits toxicvapors of NOx, HCl, and Clí.

Purification Methods

Purify it like the bromide above. [Beilstein 4 IV 327.]

InChI:InChI=1/C6H15N.ClH/c1-4-7(5-2)6-3;/h4-6H2,1-3H3;1H

Synthetic route

(R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (109431-87-0) + methanesulfonyl chloride (124-63-0) + triethylamine (121-44-8) → triethylamine hydrochloride (554-68-7) + tert-butyl (3R)-3-methylsulfonyloxypyrrolidine-1-carboxylate (127423-61-4)

Conditions	Yield
In toluene at 3 - 14℃; Product distribution / selectivity;	A n/a B 100%

triethylamine (121-44-8) → triethylamine hydrochloride (554-68-7)

Conditions	Yield
With hydrogenchloride In water for 1h; Cooling;	99%
With hydrogenchloride In water at 0℃; for 1h;	73%
With tetrachloromethane In benzene for 164h; Irradiation;	0.5%

4-Nitrophenyl chloroformate (7693-46-1) + polyethylene glycol → PEG(NPC)2 + triethylamine hydrochloride (554-68-7)

Conditions	Yield
With triethylamine In acetonitrile at 80℃; for 8h; Heating / reflux;	A 99% B n/a

triethylamine N-oxide (2687-45-8) + 1-chloro-2,4-dinitro-benzene (97-00-7) → 2,4-Dinitrophenol (51-28-5) + triethylamine hydrochloride (554-68-7)

Conditions	Yield
In N,N-dimethyl-formamide for 24h;	A 98% B 98.5%
In N,N-dimethyl-formamide for 24h; Ambient temperature;	A 98% B 98.5%

2,6-(C2H5)2C6H3NH2*BCl3 → 2,6-xylidine + ClB{NHC6H3-2,6-(C2H5)2}2 (5801-32-1) + triethylamine hydrochloride (554-68-7)

Conditions	Yield
With triethylamine extn. with petroleum ether;	A n/a B 98% C n/a

triethylamine (121-44-8) + p-toluenesulfonyl chloride (98-59-9) + 1-butyn-4-ol (927-74-2) → 3-butyn-1-yl p-toluenesulfonate (23418-85-1) + triethylamine hydrochloride (554-68-7)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 21h;	A 97% B n/a

N,N'-ethylenethiourea (96-45-7) → triethylamine hydrochloride (554-68-7)

Conditions	Yield
With triethylamine In tetrahydrofuran	97%

methyl-5-formyl-2-hydroxybenzoate (41489-76-3) + triethylamine (121-44-8) + acetyl chloride (75-36-5) → methyl 2-acetoxy-5-formylbenzoate + triethylamine hydrochloride (554-68-7)

Conditions	Yield
Stage #1: methyl-5-formyl-2-hydroxybenzoate; triethylamine In tetrahydrofuran for 0.0333333h; Stage #2: acetyl chloride at 25℃; for 2h;	A 97% B n/a

chloramphenicol (56-75-7) + Dichlorophenylphosphine (644-97-3) → triethylamine hydrochloride (554-68-7)

Conditions	Yield
With triethylamine In tetrahydrofuran	96%

B,B',B''-trichloroborazine (933-18-6) + triethylamine (121-44-8) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → B,B',B''-tris{bis(trimethylsilyl)amino}borazine (113665-33-1) + triethylamine hydrochloride (554-68-7)

Conditions	Yield
In benzene Addn. of mixt. of org. materials to a stirred soln. of B-compd. (C6H6) at room temp., stirring (room temp., 115 h).; Filtn. gives 96% of NEt3*HCl and 90% of borazine (obtained from filtrate). Purifn. by crystn. from hexane results in 71% pure material. Elem. anal.;	A 71% B 96%

ethyl 3-(chloroformyl)propionate (14794-31-1) + 4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl (14691-88-4) → triethylamine hydrochloride (554-68-7) + C15H27N2O4 (82032-23-3)

Conditions	Yield
With triethylamine In benzene 1.) 0 degC, 2.) R.T. 12 h;	A n/a B 95%

N,N-bis(trimethylsilyl)aminopropylmethyldichlorosilane (794569-27-0) + ethanol (64-17-5) → N,N-(bis-trimethylsilyl)-3-aminopropylmethyldiethoxysilane + triethylamine hydrochloride (554-68-7)

Conditions	Yield
With triethylamine In toluene at 20 - 30℃; for 3h;	A 95% B n/a

W(6+)*3Cl(1-)*CC(CH3)3(3-)*CH3OC2H4OCH3 = {Cl3(CH3OC2H4OCH3)WCC(CH3)3} + 2,4,6-Triisopropylthiophenol (22693-41-0) → {tungsten(C-t-Bu)(2,4,6-triisopropylbenzenethiolate)3Cl}{HNEt3} (111975-83-8) + triethylamine hydrochloride (554-68-7)

Conditions	Yield
With triethylamine In dichloromethane byproducts: 1,2-dimethoxyethane; Slow addn. of solid W(C-t-Bu)Cl3(dme) to a stirred and cooled (-40°C) soln. of TIPTH and Et3N, soln. turns fisrt green, then red, warming (room temp.), stirring overnight.; Addn. of pentane, Et3NHCl pptd., filtn. through Celite, evapn. in vac. to dryness, elem. anal.;	A 95% B n/a

2-furancarbonyl chloride (527-69-5) + triethylamine (121-44-8) + phenol (108-95-2) → furan-2-carboxylic acid phenyl ester (2948-14-3) + triethylamine hydrochloride (554-68-7)

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.00416667h; Flow reactor; Green chemistry;	A 95% B n/a

ethyl α-chloro-α-nitro-β-hydroxypropionate (84115-18-4) + triethylamine (121-44-8) → triethylamine hydrochloride (554-68-7)

Conditions	Yield
In ethanol; water at 29℃; for 0.3h; Product distribution;	94%

methanol (67-56-1) + N,N-bis(trimethylsilyl)aminopropylmethyldichlorosilane (794569-27-0) → bis(trimethylsilyl)aminopropylmethyldimethoxysilane + triethylamine hydrochloride (554-68-7)

Conditions	Yield
With triethylamine In toluene at 20 - 30℃; for 3h;	A 94% B n/a

mesitylthiol (1541-10-2) + W(6+)*3Cl(1-)*CC(CH3)3(3-)*CH3OC2H4OCH3 = {Cl3(CH3OC2H4OCH3)WCC(CH3)3} → {tungsten(C-t-Bu)(2,4,6-trimethylbenzenethiolate)3Cl}{HNEt3} (111997-40-1) + triethylamine hydrochloride (554-68-7)

Conditions	Yield
With triethylamine In diethyl ether byproducts: 1,2-dimethoxyethane; Slow addn. of solid W(C-t-Bu)Cl3(dme) to a stirred and cooled (-30°C) soln. of TMTH and Et3N, soln. first turns green, then yellow, warming (room temp.), stirring (90 min).; Addn. of pentane, filtn. through Celite, evapn. to dryness in vac., elem. anal.;	A 94% B n/a

methanol (67-56-1) + N,N-bis(trimethylsilyl)aminopropylmethyldichlorosilane (794569-27-0) → 3-[N,N-bis(trimethylsilyl)amino]propyldimethylmethoxysilane + triethylamine hydrochloride (554-68-7)

Conditions	Yield
With triethylamine In toluene at 20 - 30℃; for 3h;	A 92% B n/a

N-cyano-N'-methyl-N"-(2-mercaptoethyl)-guanidine (61085-25-4, 76181-72-1) + methyl vinyl ketone (78-94-4) → N-cyano-N'-methyl-N"-(2-(2-chloro-3-oxobutylthio)ethyl)guanidine + triethylamine hydrochloride (554-68-7)

Conditions	Yield
With nitrogen; chlorine; triethylamine In chloroform	A 91% B n/a
With nitrogen; chlorine; triethylamine In chloroform	A 91% B n/a

diethylacetamide (685-91-6) → triethylamine hydrochloride (554-68-7)

Conditions	Yield
Stage #1: diethylacetamide With bis(cyclopentadienyl)dihydrozirconium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; under 760.051 Torr; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether Inert atmosphere;	91%
Stage #1: diethylacetamide With [κ2-{Ph2P(Se)NC9H6N}Al(Me)2]; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; for 12h; Schlenk technique; Glovebox; Stage #2: With hydrogenchloride In water chemoselective reaction;	90%

trans-4-isopropyl cyclohexylcarboxylic acid + D-phenylalanine methyl ester hydrochloride (13033-84-6) → N-(trans-4-isopropylcyclohexyl-1-carbonyl)-d-phenylalanine methyl ester + triethylamine hydrochloride (554-68-7)

Conditions	Yield
Stage #1: trans-4-isopropylcyclohexanecarboxylic acid; triethylamine With pivaloyl chloride In acetone at 5 - 20℃; for 3.5h; Stage #2: D-phenylalanine methyl ester hydrochloride In acetone at 20℃; Product distribution / selectivity;	A 90.07% B n/a
Stage #1: trans-4-isopropylcyclohexanecarboxylic acid; triethylamine With chloroformic acid ethyl ester In acetone at 0 - 20℃; for 3.5h; Heating / reflux; Stage #2: D-phenylalanine methyl ester hydrochloride In acetone at 25℃; Product distribution / selectivity;	A 78.42% B n/a

2-(morpholin-4-yl)ethanol (622-40-2) + 2-chloronicotinic acid (2942-59-8) → 2-chloronicotinic acid 1(2-morpholinoethyl)ester + triethylamine hydrochloride (554-68-7)

Conditions	Yield
With thionyl chloride; triethylamine In toluene	A 90% B n/a

benzoyl chloride (98-88-4) + triethylamine (121-44-8) + phenol (108-95-2) → benzoic acid phenyl ester (93-99-2) + triethylamine hydrochloride (554-68-7)

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.00694444h; Flow reactor; Green chemistry;	A 90% B n/a

carbonochloridic acid 1-chloro-ethyl ester (50893-53-3) + triethylamine (121-44-8) + ethanethiol (75-08-1) → triethylamine hydrochloride (554-68-7) + O-(1-chloroethyl) S-ethyl carbonothioate (101506-43-8)

Conditions	Yield
In diethyl ether at 0 - 20℃; for 5h;	A n/a B 89%

2-(2,4-dimethoxyphenyl)-3-(2-nitrobenzenesulfenyl)-4(S)-phenyl-5(R)-oxazolidinecarboxylic acid sodium salt + triethylamine hydrochloride (554-68-7) → triethylammonium 2-(2,4-dimethoxyphenyl)-3-(2-nitrobenzenesulfenyl)-4-phenyl-5-oxazolidinecarboxylate

Conditions	Yield
In methanol for 3h;	100%

closo-[tetraphenylphosphonium]2[B8H8] + triethylamine hydrochloride (554-68-7) → closo-[tetraphenylphosphonium][B8H9]

Conditions	Yield
In acetonitrile (Ar); MeCN added to B compd. and N(C2H5)3HCl, stirred for 15 min; Et2O added carefully, crystd. for 5 d, dried (vac., overnight), H2O added, stirred for 15 min, sepd., washed (H2O), dried (vac.);	100%

triethylamine hydrochloride (554-68-7) + copper(l) chloride → C6H15N*ClH*CuCl

Conditions	Yield
at 60℃; for 4h; Inert atmosphere; Sealed tube;	100%

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%

triethylamine hydrochloride (554-68-7) + carbonic acid dimethyl ester (616-38-6) → triethylmethylammonium chloride (10052-47-8)

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;

(Bu4N)2[Fe4S4(1,3,5-tris-((4,6-dimethyl-3-mercaptophenyl)thio)-2,4,6-tris-(p-tolylthio)benzenate(3-))(SC2H5)] (137003-15-7) + triethylamine hydrochloride (554-68-7) → (Bu4N)2[Fe4S4(1,3,5-tris-((4,6-dimethyl-3-mercaptophenyl)thio)-2,4,6-tris-(p-tolylthio)benzenate(3-))Cl]

Conditions	Yield
In acetonitrile byproducts: Et3N, EtSH; N2-atmosphere; stirring equimolar amts. for 12 h (periodic removal of Et3N and EtSH by evacuation); filtration, solvent removal (vac.);	99%

(Bu4N)2[Fe4Se4(1,3,5-tris-((4,6-dimethyl-3-mercaptophenyl)thio)-2,4,6-tris-(p-tolylthio)benzenate(3-))(SC2H5)] + triethylamine hydrochloride (554-68-7) → (Bu4N)2[Fe4Se4(1,3,5-tris-((4,6-dimethyl-3-mercaptophenyl)thio)-2,4,6-tris-(p-tolylthio)benzenate(3-))Cl]

Conditions	Yield
In acetonitrile byproducts: Et3N, EtSH; N2-atmosphere; stirring equimolar amts. for 12 h (periodic removal of Et3N and EtSH by evacuation); filtration, solvent removal (vac.);	99%

[(1,3-C6H3(CH2P(CF3)2)2)Ir(H)Cl(η2-C2H4)] (1266146-97-7) + triethylamine hydrochloride (554-68-7) → [(1,3-C6H3(CH2P(CF3)2)2)Ir(H)Cl2][HNEt3] (1268160-20-8)

Conditions	Yield
In benzene (N2); glovebox technique; mixt. of Ir complex (1 equiv.) and Et3NHCl (1 equiv.) in C6H6 was agitated at 20°C for 20 min;	99%

2-Iodobenzoyl chloride (609-67-6) + triethylamine hydrochloride (554-68-7) → benodanil (15310-01-7)

Conditions	Yield
With triethylamine; aniline In water; benzene	98%

triethylamine hydrochloride (554-68-7) + chloroacetyl chloride (79-04-9) + 3,3-dimethyl-7-nitrobenzisoselenazoline (173026-14-7) → N-(chloroacetyl)-3,3-dimethyl-7-nitrobenzisoselenazoline (204272-78-6)

Conditions	Yield
With sodium chloride In tetrahydrofuran; water; ethyl acetate	97%

Upstream product

• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 59-49-4 2-Benzoxazolinone 
• 2623-45-2 2-chloro-1-(2,4-dimethyl-phenyl)-ethanone 
• 65610-02-8 2-chloro-1-(3-chloro-4-methylphenyl)ethan-1-one 
• 60988-75-2 2-chloro-1-(4-chloro-2-methylphenyl)ethan-1-one 
• 99-81-0 4-Nitrophenacyl bromide 
• 2382-96-9 benzo[d]oxazole-2-(3H)-thione 
• 532-27-4 1-chloroacetophenone 
• 937-20-2 p-chlorophenacyl chloride 
• 19932-84-4 6-chlorobenzo[d]oxazol-2(3H)-one 
• 19932-85-5 6-bromobenzo[d]oxazol-2(3H)-one 
• 116-16-5 1,1,1,3,3,3-hexachloro-propan-2-one 
• 1809-21-8 di-n-propyl phosphonate 
• 121-44-8 triethylamine 

Downstream Products

• 34124-78-2 2,5-diphenyl-3-ethoxyfuran 
• 55-18-5 N-Nitrosodiethylamine 
• 156222-03-6 2-butyl-4,5-dihydro-4-oxo-3-[2'-(tetrazol-5-yl)-biphenyl-4-ylmethyl]-5-(o-ethoxycarbonyl-benzyl)-3H-imidazo[4,5-c]-pyridine 
• 57536-91-1 1-naphthalen-2-yl-piperazine 
• 152120-05-3 2-<2-<3-<5-(benzyloxy)-2-ethyl-4-(4-fluorophenyl)phenoxy>propoxy>phenyl>-1-(1H-tetrazol-5-yl)ethane 
• 5187-94-0 ampicillin trihydrate 
• 39950-67-9 1,1,3-trichloro-3-phenyl-propane-1-phosphonic dichloride 
• 15310-01-7 benodanil 
• 1333-74-0 hydrogen 
• 1722-26-5 triethylamine-borane 
• 41086-64-0 (Et₃NH)2(hexachlorostannate) 
• 75-77-4 chloro-trimethyl-silane 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 378784-00-0 rhodium 

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