Product Name

  • Name

    Trimethylphenylammonium chloride

  • EINECS 205-319-0
  • CAS No. 138-24-9
  • Article Data6
  • CAS DataBase
  • Density 1.0683 (rough estimate)
  • Solubility soluble in water
  • Melting Point 246-248 °C (dec.)(lit.)
  • Formula C9H14N.Cl
  • Boiling Point 283.2°C (rough estimate)
  • Molecular Weight 171.67
  • Flash Point
  • Transport Information UN 2811 6.1/PG 3
  • Appearance White or greyish-blue crystalline powder
  • Safety 53-25-39-45
  • Risk Codes 24/25
  • Molecular Structure Molecular Structure of 138-24-9 (Trimethylphenylammonium chloride)
  • Hazard Symbols ToxicT
  • Synonyms Ammonium,trimethylphenyl-, chloride (8CI);Benzenaminium, N,N,N-trimethyl-, chloride(9CI);Trimethylphenylammonium chloride (6CI,7CI);Ammonyx 200;N,N,N-Trimethylanilinium chloride;Trimethylanilinium chloride;
  • PSA 0.00000
  • LogP -1.11270

Synthetic route

bis(chloromethyl)mercury
5293-94-7

bis(chloromethyl)mercury

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

A

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

B

4,4'-methylene-bis(N,N-dimethylaniline)
101-61-1

4,4'-methylene-bis(N,N-dimethylaniline)

Conditions
ConditionsYield
In dibutyl ether at 100℃; for 48h;A n/a
B 96%
phenyltrimethylammonium iodide
98-04-4

phenyltrimethylammonium iodide

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

Conditions
ConditionsYield
With silver(I) chloride
methylene chloride
74-87-3

methylene chloride

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

Conditions
ConditionsYield
trichlorophosphate
4-trimethylammoniumbenzene diazonium tetrafluoroborate chloride

4-trimethylammoniumbenzene diazonium tetrafluoroborate chloride

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

Conditions
ConditionsYield
With pyrene In acetonitrile Irradiation; CIDNP effects of the photochemical dediazonation; reaction in the absence of pyrene in dioxane;
C29H38N6O4*C9H14N(1+)*Cl(1-)

C29H38N6O4*C9H14N(1+)*Cl(1-)

A

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

B

Trp-Aib-Gly-Leu-NHPh
232279-44-6

Trp-Aib-Gly-Leu-NHPh

Conditions
ConditionsYield
In chloroform-d1 at 24.84℃; Equilibrium constant; complex formation;
C31H42N6O4*C9H14N(1+)*Cl(1-)

C31H42N6O4*C9H14N(1+)*Cl(1-)

A

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

B

Trp-Aib-Gly-Leu-NH-C6H3(3,5-Me2)
271770-12-8

Trp-Aib-Gly-Leu-NH-C6H3(3,5-Me2)

Conditions
ConditionsYield
In chloroform-d1 at 24.84℃; Equilibrium constant; complex formation;
N-methylaniline
100-61-8

N-methylaniline

platinum

platinum

A

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

B

sarpagyne

sarpagyne

Conditions
ConditionsYield
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

aniline

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

A

N-methylaniline hydrochloride
2739-12-0

N-methylaniline hydrochloride

B

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

C

aniline hydrochloride
142-04-1

aniline hydrochloride

D

N,N-dimethylaniline hydrochloride
5882-44-0

N,N-dimethylaniline hydrochloride

Conditions
ConditionsYield
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

phenyltrimethylammonium chloride

MORPHIN
57-27-2

MORPHIN

codeine phosphate
52-28-8

codeine phosphate

Conditions
ConditionsYield
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%
Conditions
ConditionsYield
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

phenyltrimethylammonium chloride

MORPHIN
57-27-2

MORPHIN

codeine
76-57-3

codeine

Conditions
ConditionsYield
With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene99%
With potassium carbonate In toluene99%
With potassium carbonate In toluene98%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

4-methoxyphenylzinc chloride
93296-09-4

4-methoxyphenylzinc chloride

4-methoxylbiphenyl
613-37-6

4-methoxylbiphenyl

Conditions
ConditionsYield
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

N-formyl-2-hydroxy-3-methoxy-6-oxomorphinan

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

N-formyl-2,3-dimethoxy-6-oxomorphinan

N-formyl-2,3-dimethoxy-6-oxomorphinan

Conditions
ConditionsYield
With sodium methylate In 1,4-dioxane; N,N-dimethyl-formamide at 80℃; for 12h;93%
para-tert-butylphenol
98-54-4

para-tert-butylphenol

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

A

1-(tert-butyl)-4-methoxybenzene
5396-38-3

1-(tert-butyl)-4-methoxybenzene

B

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With caesium carbonate In toluene for 27h; Heating;A 92%
B n/a
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

14-benzyloxy-17-cyclopropylmethyl-4-hydroxymorphinan-6-one
220556-53-6

14-benzyloxy-17-cyclopropylmethyl-4-hydroxymorphinan-6-one

14-benzyloxy-17-cyclopropylmethyl-4-hydroxymorphinan-6-one hydrochloride

14-benzyloxy-17-cyclopropylmethyl-4-hydroxymorphinan-6-one hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; potassium carbonate In N,N-dimethyl-formamide for 7h;92%
tris(trifluoromethanesulfonyl)methide potassium salt
114395-69-6

tris(trifluoromethanesulfonyl)methide potassium salt

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

C4F9O6S3(1-)*C9H14N(1+)
1345491-96-4

C4F9O6S3(1-)*C9H14N(1+)

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 1h;90.2%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

(4-(dimethylamino)phenyl)zinc(II) chloride
93296-10-7

(4-(dimethylamino)phenyl)zinc(II) chloride

N,N-dimethyl-4-biphenylamine
1137-79-7

N,N-dimethyl-4-biphenylamine

Conditions
ConditionsYield
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

phenyltrimethylammonium chloride

β-naphthol
135-19-3

β-naphthol

A

2-Methoxynaphthalene
93-04-9

2-Methoxynaphthalene

B

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With caesium carbonate In toluene for 2h; Heating;A 89%
B n/a
4-nitro-phenol
100-02-7

4-nitro-phenol

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

A

para-methoxynitrobenzene
100-17-4

para-methoxynitrobenzene

B

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With caesium carbonate In toluene for 48h; Heating;A 88%
B n/a
α-naphthol
90-15-3

α-naphthol

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

A

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

B

1-Methoxynaphthalene
2216-69-5

1-Methoxynaphthalene

Conditions
ConditionsYield
With caesium carbonate In toluene for 21h; Heating;A n/a
B 87%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

boldine
476-70-0

boldine

glaucine
475-81-0

glaucine

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 16h;87%
thymol
89-83-8

thymol

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

Thymol methyl ether
1076-56-8

Thymol methyl ether

Conditions
ConditionsYield
With diethylene glycol dimethyl ether; potassium carbonate at 150 - 155℃; for 0.5h;86%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

(-)-3,14-dimethoxy-4-hydroxy-N-methylmorphinan-6-one
78072-08-9

(-)-3,14-dimethoxy-4-hydroxy-N-methylmorphinan-6-one

(-)-3,4,14-trimethoxy-N-methylmorphinan-6-one
92055-62-4

(-)-3,4,14-trimethoxy-N-methylmorphinan-6-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 5h;85%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

4-chloro-phenol
106-48-9

4-chloro-phenol

A

4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

B

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

Conditions
ConditionsYield
With caesium carbonate In toluene for 6h; Heating;A 85%
B n/a
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

5,6-didehydro-4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6-carbonitrile
342622-12-2

5,6-didehydro-4,14β-dihydroxy-3-methoxy-17-methylmorphinan-6-carbonitrile

5,6-didehydro-14β-hydroxy-3,4-dimethoxy-17-methylmorphinan-6-carbonitrile

5,6-didehydro-14β-hydroxy-3,4-dimethoxy-17-methylmorphinan-6-carbonitrile

Conditions
ConditionsYield
With nitrogen; potassium carbonate In N,N-dimethyl-formamide for 5h; Heating;85%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

3-(benzyloxy)-14-ethoxy-4-hydroxy-N-methylmorphinan-6-one
165673-73-4

3-(benzyloxy)-14-ethoxy-4-hydroxy-N-methylmorphinan-6-one

3-(benzyloxy)-14-ethoxy-4-methoxy-N-methylmorphinan-6-one
165673-74-5

3-(benzyloxy)-14-ethoxy-4-methoxy-N-methylmorphinan-6-one

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

copper(II) choride dihydrate

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

bis(trimethylphenylammonium)tetrachloridocuprate(II)

bis(trimethylphenylammonium)tetrachloridocuprate(II)

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol for 0.5h; Reflux;83%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

C27H27NO4

C27H27NO4

C28H29NO4

C28H29NO4

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

allopseudomorphine

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

Conditions
ConditionsYield
With sodium ethanolate In toluene Reflux;80%
8-bromo-6-methoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinolin-7-ol
1426260-31-2

8-bromo-6-methoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinolin-7-ol

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

8-bromo-6,7-dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline
1426260-91-4

8-bromo-6,7-dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline

Conditions
ConditionsYield
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

phenyltrimethylammonium chloride

4,14-dihydroxy-N-methylmorphinan-6-one
81165-09-5

4,14-dihydroxy-N-methylmorphinan-6-one

(-)-4-methoxy-14-hydroxy-6-keto-N-methylmorphinan
81182-02-7

(-)-4-methoxy-14-hydroxy-6-keto-N-methylmorphinan

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide77%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

5-methyldihydrothebainone

5-methyldihydrothebainone

(-)-3,4-dimethoxy-5,17-dimethylmorphinan-6-one hydrobromide

(-)-3,4-dimethoxy-5,17-dimethylmorphinan-6-one hydrobromide

Conditions
ConditionsYield
With hydrogen bromide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;76%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

(+/-)-2,4-dihydroxy-N-formylmorphinan-6-one
76786-95-3

(+/-)-2,4-dihydroxy-N-formylmorphinan-6-one

2,4-dimethoxy-N-formylmorphinan-6-one

2,4-dimethoxy-N-formylmorphinan-6-one

Conditions
ConditionsYield
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

(-)-4-hydroxy-14-methoxy-N-methylmorphinan-6-one

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

(-)-4,14-dimethoxy-N-methylmorphinan-6-one
92055-59-9

(-)-4,14-dimethoxy-N-methylmorphinan-6-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 2h;73%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

C18H23NO3

C18H23NO3

(-)-3,4-dimethoxy-N-methyl-6-oxomorphinan

(-)-3,4-dimethoxy-N-methyl-6-oxomorphinan

Conditions
ConditionsYield
With sodium methylate In 1,4-dioxane for 24h; Heating;73%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

(-)-4,14β-dihydroxy-5β,17-dimethyl-3-methoxymorphinan-6-one

(-)-4,14β-dihydroxy-5β,17-dimethyl-3-methoxymorphinan-6-one

(-)-3,4-dimethoxy-N-5-dimethylmorphinan-6-one hydrobromide

(-)-3,4-dimethoxy-N-5-dimethylmorphinan-6-one hydrobromide

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

Phenyltrimethylammonium chloride Chemical Properties

IUPAC Name: Benzenaminium, N,N,N-trimethyl-, chloride
The MF of Benzenaminium, N,N,N-trimethyl-, chloride (138-24-9) is C9H14ClN.

                                      
The MW of Benzenaminium, N,N,N-trimethyl-, chloride (138-24-9) is 171.67.
Synonyms of Benzenaminium, N,N,N-trimethyl-, chloride (138-24-9): Ammonium, phenyltrimethyl-, chloride ; Benzenaminium, N,N,N-trimethyl-, chloride ; N,N,N-Trimethylanilinium chloride ; N,N,N-Trimethylbenzenaminium chloride ;  Phenyltrimethylammonium chloride 
Product Categories: Ammonium Chlorides (Quaternary);Quaternary Ammonium Compounds
Form: White or greyish-bleu crystalline powder
Melting Point: 246-248 °C (dec.)(lit.)
Water Solubility: soluble
Sensitive: Hygroscopic
EINECS: 205-319-0
BRN: 3572527

Phenyltrimethylammonium chloride Uses

  Benzenaminium, N,N,N-trimethyl-, chloride (138-24-9) is used as pharmaceutical Intermediates.

Phenyltrimethylammonium chloride Toxicity Data With Reference

1.    

orl-mus LDLo:200 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 43 (1931),413.
2.    

ivn-mus LDLo:15 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 43 (1931),413.

Phenyltrimethylammonium chloride Consensus Reports

Reported in EPA TSCA Inventory.

Phenyltrimethylammonium chloride Safety Profile

Poison by ingestion and intravenous routes. When heated to decomposition it emits very toxic fumes of NOx, NH3, and Cl.
Safety information of Benzenaminium, N,N,N-trimethyl-, chloride (138-24-9):
Hazard Codes  T
Risk Statements 
24/25  Toxic in contact with skin and if swallowed
Safety Statements 
53  Avoid exposure - obtain special instruction before use
25  Avoid contact with eyes
39  Wear eye/face protection
45  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR  UN 2811 6.1/PG 3
WGK Germany  1
RTECS  BT2190000
HazardClass  6.1
PackingGroup  III
HS Code  29239000

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