138-24-9

Basic information

• Product Name: Trimethylphenylammonium chloride
• Synonyms: Ammonium, phenyltrimethyl-, chloride;Ammonium, trimethylphenyl-, chloride;Ammonyx 200;ammonyx200;Benzenaminium, N,N,N-trimethyl-, chloride;Benzenaminium,N,N,N-trimethyl-,chloride;n,n,n-trimethyl-benzenaminiuchloride;n,n,n-trimethylbenzenaminiumchloride
• CAS NO: 138-24-9
• Molecular Formula: C₉H₁₄N*Cl
• Molecular Weight: 171.67
• EINECS: 205-319-0
• Product Categories: Ammonium Chlorides (Quaternary);Quaternary Ammonium Compounds
• Mol File: 138-24-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 246-248 °C (dec.)(lit.)
• Boiling Point: 283.2°C (rough estimate)
• Appearance: White or greyish-blue crystalline powder
• Density: 1.0683 (rough estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.6224 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: H2O: 0.1 g/mL, clear
• Explosive Limit: 1-6%(V)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• BRN: 3572527
• CAS DataBase Reference: Trimethylphenylammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethylphenylammonium chloride(138-24-9)
• EPA Substance Registry System: Trimethylphenylammonium chloride(138-24-9)

Safety Data

• Hazard Codes: T
• Statements: 24/25
• Safety Statements: 53-25-39-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 1
• RTECS: BT2190000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 138-24-9(Hazardous Substances Data)

Usage

Chemical Properties

White or greyish-bleu crystalline powder

Uses

Phenyltrimethylammonium chloride is an effective phase transfer catalyst, methylating agent, also useful for alkaline depolymerizations, corrosion inhibitor for low carbon steel.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C9H13N.ClH/c1-6-4-5-9(10)8(3)7(6)2;/h4-5H,10H2,1-3H3;1H

Synthetic route

bis(chloromethyl)mercury (5293-94-7) + N,N-dimethyl-aniline (121-69-7) → phenyltrimethylammonium chloride (138-24-9) + 4,4'-methylene-bis(N,N-dimethylaniline) (101-61-1)

Conditions	Yield
In dibutyl ether at 100℃; for 48h;	A n/a B 96%

phenyltrimethylammonium iodide (98-04-4) → phenyltrimethylammonium chloride (138-24-9)

Conditions	Yield
With silver(I) chloride

methylene chloride (74-87-3) + N,N-dimethyl-aniline (121-69-7) → phenyltrimethylammonium chloride (138-24-9)

Conditions	Yield
trichlorophosphate

4-trimethylammoniumbenzene diazonium tetrafluoroborate chloride → phenyltrimethylammonium chloride (138-24-9)

Conditions	Yield
With pyrene In acetonitrile Irradiation; CIDNP effects of the photochemical dediazonation; reaction in the absence of pyrene in dioxane;

C29H38N6O4*C9H14N(1+)*Cl(1-) → phenyltrimethylammonium chloride (138-24-9) + Trp-Aib-Gly-Leu-NHPh (232279-44-6)

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

C31H42N6O4*C9H14N(1+)*Cl(1-) → phenyltrimethylammonium chloride (138-24-9) + Trp-Aib-Gly-Leu-NH-C6H3(3,5-Me2) (271770-12-8)

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

N-methylaniline (100-61-8) + platinum → phenyltrimethylammonium chloride (138-24-9) + sarpagyne

Conditions	Yield
Multi-step reaction with 2 steps 1: 42 percent / tetrahydrofuran / 36 h / 20 °C 2: dibutyl ether / 48 h / 100 °C View Scheme

aniline (62-53-3) + methyl trifluoromethanesulfonate (333-27-7) → N-methylaniline hydrochloride (2739-12-0) + phenyltrimethylammonium chloride (138-24-9) + aniline hydrochloride (142-04-1) + N,N-dimethylaniline hydrochloride (5882-44-0)

Conditions	Yield
Stage #1: aniline; methyl trifluoromethanesulfonate 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;

phenyltrimethylammonium chloride (138-24-9) + MORPHIN (57-27-2) → codeine phosphate (52-28-8)

Conditions	Yield
Stage #1: phenyltrimethylammonium chloride; MORPHIN With potassium phosphate In acetone at 50 - 60℃; for 25h; Heating / reflux; Stage #2: With phosphoric acid In water; acetone at 20℃; for 0.5h; Product distribution / selectivity;	100%
Stage #1: phenyltrimethylammonium chloride; MORPHIN With potassium hydrogencarbonate In toluene at 50 - 115℃; for 8 - 28h; Heating / reflux; Stage #2: With phosphoric acid In ethanol; water; toluene at 20℃; for 0.5h; Product distribution / selectivity;	90%
Stage #1: phenyltrimethylammonium chloride; MORPHIN With potassium phosphate In toluene at 70 - 115℃; for 2h; Heating / reflux; Stage #2: With phosphoric acid In ethanol; water; toluene at 20 - 30℃; for 0.75h; Product distribution / selectivity;	82%

morphine (57-27-2, 143-70-4, 6912-73-8, 16206-77-2, 27067-73-8, 65165-99-3, 70982-47-7) + phenyltrimethylammonium chloride (138-24-9) → codeine phosphate (52-28-8, 4478-25-5, 17682-64-3, 56050-09-0, 76034-17-8)

Conditions	Yield
Stage #1: morphine; phenyltrimethylammonium chloride With potassium hydrogencarbonate In toluene at 50 - 115℃; for 29h; Heating / reflux; Stage #2: In toluene at 20℃; activated carbon (charcoal); Stage #3: With phosphoric acid In ethanol; water at 20℃; for 0.5h;	99.6%
Stage #1: morphine; phenyltrimethylammonium chloride With potassium hydrogencarbonate In toluene at 50 - 115℃; for 9h; Heating / reflux; Stage #2: In toluene at 20℃; activated carbon (charcoal); Stage #3: With phosphoric acid In ethanol; water at 20℃; for 0.5h;	99.8%

phenyltrimethylammonium chloride (138-24-9) + MORPHIN (57-27-2) → codeine (76-57-3)

Conditions	Yield
With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene	99%
With potassium carbonate In toluene	99%
With potassium carbonate In toluene	98%

phenyltrimethylammonium chloride (138-24-9) + 4-methoxyphenylzinc chloride (93296-09-4) → 4-methoxylbiphenyl (613-37-6)

Conditions	Yield
With C27H22Cl2N3NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one for 12h; Inert atmosphere; Schlenk technique; Heating;	95%
With C38H34Br2N4Ni2P2; potassium iodide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 65℃; for 12h; Inert atmosphere; Schlenk technique;	90%
With C32H26ClN2NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 85℃; for 12h; Inert atmosphere;	74%

N-formyl-2-hydroxy-3-methoxy-6-oxomorphinan (15172-46-0, 17479-85-5) + phenyltrimethylammonium chloride (138-24-9) → N-formyl-2,3-dimethoxy-6-oxomorphinan

Conditions	Yield
With sodium methylate In 1,4-dioxane; N,N-dimethyl-formamide at 80℃; for 12h;	93%

para-tert-butylphenol (98-54-4) + phenyltrimethylammonium chloride (138-24-9) → 1-(tert-butyl)-4-methoxybenzene (5396-38-3) + N,N-dimethyl-aniline (121-69-7)

Conditions	Yield
With caesium carbonate In toluene for 27h; Heating;	A 92% B n/a

phenyltrimethylammonium chloride (138-24-9) + 14-benzyloxy-17-cyclopropylmethyl-4-hydroxymorphinan-6-one (220556-53-6) → 14-benzyloxy-17-cyclopropylmethyl-4-hydroxymorphinan-6-one hydrochloride

Conditions	Yield
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide for 7h;	92%

tris(trifluoromethanesulfonyl)methide potassium salt (114395-69-6) + phenyltrimethylammonium chloride (138-24-9) → C4F9O6S3(1-)*C9H14N(1+) (1345491-96-4)

Conditions	Yield
In ethyl acetate at 20℃; for 1h;	90.2%

phenyltrimethylammonium chloride (138-24-9) + (4-(dimethylamino)phenyl)zinc(II) chloride (93296-10-7) → N,N-dimethyl-4-biphenylamine (1137-79-7)

Conditions	Yield
With bis(tricyclohexylphosphine)nickel(II) dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 90℃; for 8h; Negishi coupling reaction; Inert atmosphere;	90%

phenyltrimethylammonium chloride (138-24-9) + β-naphthol (135-19-3) → 2-Methoxynaphthalene (93-04-9) + N,N-dimethyl-aniline (121-69-7)

Conditions	Yield
With caesium carbonate In toluene for 2h; Heating;	A 89% B n/a

4-nitro-phenol (100-02-7) + phenyltrimethylammonium chloride (138-24-9) → para-methoxynitrobenzene (100-17-4) + N,N-dimethyl-aniline (121-69-7)

Conditions	Yield
With caesium carbonate In toluene for 48h; Heating;	A 88% B n/a

α-naphthol (90-15-3) + phenyltrimethylammonium chloride (138-24-9) → N,N-dimethyl-aniline (121-69-7) + 1-Methoxynaphthalene (2216-69-5)

Conditions	Yield
With caesium carbonate In toluene for 21h; Heating;	A n/a B 87%

phenyltrimethylammonium chloride (138-24-9) + boldine (476-70-0) → glaucine (475-81-0)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 16h;	87%

thymol (89-83-8) + phenyltrimethylammonium chloride (138-24-9) → Thymol methyl ether (1076-56-8)

Conditions	Yield
With diethylene glycol dimethyl ether; potassium carbonate at 150 - 155℃; for 0.5h;	86%

phenyltrimethylammonium chloride (138-24-9) + (-)-3,14-dimethoxy-4-hydroxy-N-methylmorphinan-6-one (78072-08-9) → (-)-3,4,14-trimethoxy-N-methylmorphinan-6-one (92055-62-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 5h;	85%

phenyltrimethylammonium chloride (138-24-9) + 4-chloro-phenol (106-48-9) → 4-chloromethoxybenzene (623-12-1) + N,N-dimethyl-aniline (121-69-7)

Conditions	Yield
With caesium carbonate In toluene for 6h; Heating;	A 85% B n/a

phenyltrimethylammonium chloride (138-24-9) + 5,6-didehydro-4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6-carbonitrile (342622-12-2) → 5,6-didehydro-14β-hydroxy-3,4-dimethoxy-17-methylmorphinan-6-carbonitrile

Conditions	Yield
With nitrogen; potassium carbonate In N,N-dimethyl-formamide for 5h; Heating;	85%

phenyltrimethylammonium chloride (138-24-9) + 3-(benzyloxy)-14-ethoxy-4-hydroxy-N-methylmorphinan-6-one (165673-73-4) → 3-(benzyloxy)-14-ethoxy-4-methoxy-N-methylmorphinan-6-one (165673-74-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 3h;	84%

morphine (57-27-2, 143-70-4, 6912-73-8, 16206-77-2, 27067-73-8, 65165-99-3, 70982-47-7) + phenyltrimethylammonium chloride (138-24-9) → 4,5α-epoxy-3-methoxy-17-methyl-morphin-7-en-6α-ol (76-57-3, 509-64-8, 7235-41-8, 16206-70-5, 27067-72-7, 64520-25-8, 70982-46-6)

Conditions	Yield
With sodium hydrogencarbonate In toluene at 50 - 115℃; for 49h; Heating / reflux;	84%
Stage #1: morphine; phenyltrimethylammonium chloride With potassium dihydrogenphosphate In toluene at 50 - 115℃; for 7.5h; Heating / reflux; Stage #2: With sodium hydroxide In Isopropyl acetate; water; acetic acid at 20℃; pH=14; activated carbon (charcoal);	82%
Stage #1: morphine; phenyltrimethylammonium chloride With potassium dihydrogenphosphate In toluene at 50 - 115℃; for 3.5h; Heating / reflux; Stage #2: In water; acetic acid at 20℃; activated carbon (charcoal); Stage #3: With sodium hydroxide In water pH=12;

copper(II) choride dihydrate + phenyltrimethylammonium chloride (138-24-9) → bis(trimethylphenylammonium)tetrachloridocuprate(II)

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol for 0.5h; Reflux;	83%

phenyltrimethylammonium chloride (138-24-9) + C27H27NO4 → C28H29NO4

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;	82%

allopseudomorphine + phenyltrimethylammonium chloride (138-24-9) → allopseudocodeine (466-96-6, 509-55-7, 16206-67-0, 16206-74-9, 49751-24-8)

Conditions	Yield
With sodium ethanolate In toluene Reflux;	80%

8-bromo-6-methoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinolin-7-ol (1426260-31-2) + phenyltrimethylammonium chloride (138-24-9) → 8-bromo-6,7-dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline (1426260-91-4)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 70℃; for 8h; Inert atmosphere;	79%
With potassium tert-butylate In N,N-dimethyl-formamide at 60 - 70℃; for 8h; Inert atmosphere;	79%

phenyltrimethylammonium chloride (138-24-9) + 4,14-dihydroxy-N-methylmorphinan-6-one (81165-09-5) → (-)-4-methoxy-14-hydroxy-6-keto-N-methylmorphinan (81182-02-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	77%

phenyltrimethylammonium chloride (138-24-9) + 5-methyldihydrothebainone → (-)-3,4-dimethoxy-5,17-dimethylmorphinan-6-one hydrobromide

Conditions	Yield
With hydrogen bromide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;	76%

phenyltrimethylammonium chloride (138-24-9) + (+/-)-2,4-dihydroxy-N-formylmorphinan-6-one (76786-95-3) → 2,4-dimethoxy-N-formylmorphinan-6-one

Conditions	Yield
With sodium methylate In 1,4-dioxane; N,N-dimethyl-formamide at 80℃; for 16h;	74%

(-)-4-hydroxy-14-methoxy-N-methylmorphinan-6-one (92055-58-8) + phenyltrimethylammonium chloride (138-24-9) → (-)-4,14-dimethoxy-N-methylmorphinan-6-one (92055-59-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 2h;	73%

phenyltrimethylammonium chloride (138-24-9) + C18H23NO3 → (-)-3,4-dimethoxy-N-methyl-6-oxomorphinan

Conditions	Yield
With sodium methylate In 1,4-dioxane for 24h; Heating;	73%

phenyltrimethylammonium chloride (138-24-9) + (-)-4,14β-dihydroxy-5β,17-dimethyl-3-methoxymorphinan-6-one → (-)-3,4-dimethoxy-N-5-dimethylmorphinan-6-one hydrobromide

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 3h;	73%

Upstream product

• 5293-94-7 bis(chloromethyl)mercury 
• 121-69-7 N,N-dimethyl-aniline 
• 62-53-3 aniline 
• 333-27-7 methyl trifluoromethanesulfonate 
• 100-61-8 N-methylaniline 
• 74-87-3 methylene chloride 
• 98-04-4 phenyltrimethylammonium iodide 

Downstream Products

• 121-69-7 N,N-dimethyl-aniline 
• 110-82-7 cyclohexane 
• 74-87-3 methylene chloride 
• 75-50-3 trimethylamine 
• 165673-74-5 3-(benzyloxy)-14-ethoxy-4-methoxy-N-methylmorphinan-6-one 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 2216-69-5 1-Methoxynaphthalene 
• 5396-38-3 1-(tert-butyl)-4-methoxybenzene 
• 20883-98-1 methyl 2-coumarate 
• 61982-91-0 1,2,3,4-tetrahydro-5-methoxynaphthalen-1-ol 
• 623-12-1 4-chloromethoxybenzene 
• 150-78-7 1,4-dimethoxybezene 
• 4358-87-6 (RS)-methyl mandelate 
• 93-04-9 2-Methoxynaphthalene 

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This work presents the studies of the nucleation processes and surface morphology of aluminium electrodeposits obtained on tungsten (W) and aluminium (Al) electrodes from 2:1 molar ratio aluminium chloride (AlCl 3 )–trimethylphenylammonium chloride (TMPAC) ionic liquids. The deposition ...detailed

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