16056-11-4

Basic information

• Product Name: Phenyltrimethylammonium bromide
• Synonyms: TRIMETHYLPHENYLAMMONIUM BROMIDE;n,n,n-trimethylanilinium bromide;PHENYLTRIMETHYLAMMONIUM BROMIDE;n,n,n-trimethyl-benzenaminiubromide;n,n-trimethyl-benzenaminiumbromide;phenyltrimethyl-ammoniubromide;ro2-2979;N-Phenyl-N,N,N-trimethylammonium bromide
• CAS NO: 16056-11-4
• Molecular Formula: Br*C₉H₁₄N
• Molecular Weight: 216.12
• EINECS: 240-202-8
• Product Categories: Ammonium Bromides (Quaternary);Quaternary Ammonium Compounds
• Mol File: 16056-11-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 215 °C (dec.)(lit.)
• Appearance: white to blue crystalline powder or chunks
• Density: 1.2
• Refractive Index: 1.5870 (estimate)
• Storage Temp.: Refrigerator
• Water Solubility: almost transparency in Water
• Sensitive: Hygroscopic
• BRN: 3917006
• CAS DataBase Reference: Phenyltrimethylammonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyltrimethylammonium bromide(16056-11-4)
• EPA Substance Registry System: Phenyltrimethylammonium bromide(16056-11-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: 2811
• WGK Germany: 3
• RTECS: BT2100000
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 16056-11-4(Hazardous Substances Data)

Usage

Chemical Properties

white to blue crystalline powder or chunks

InChI:InChI=1/C9H14N.BrH/c1-10(2,3)9-7-5-4-6-8-9;/h4-8H,1-3H3;1H/q+1;/p-1

Synthetic route

methanol (67-56-1) + N,N-dimethyl-aniline (121-69-7) → N,N,N-trimethylanilinium bromide (16056-11-4)

Conditions	Yield
at 120 - 130℃; beim Erhitzen von feuchtem bromwasserstoffsauren Dimethylanilin im Druckrohr;

methyl bromide (74-83-9) + N,N-dimethyl-aniline (121-69-7) → N,N,N-trimethylanilinium bromide (16056-11-4)

bromocyane (506-68-3) + N,N-dimethyl-aniline (121-69-7) → methyl(phenyl)cyanamide (18773-77-8) + N,N,N-trimethylanilinium bromide (16056-11-4)

Acetyl bromide (506-96-7) + N,N-dimethyl-aniline (121-69-7) → N-acetyl-N-methylaniline (579-10-2) + N,N,N-trimethylanilinium bromide (16056-11-4)

N,N-dimethyl-aniline (121-69-7) + α-bromoacetophenone (70-11-1) → N-methyl-N-phenacylaniline (32119-53-2) + N,N,N-trimethylanilinium bromide (16056-11-4)

N,N-dimethyl-aniline (121-69-7) + i-pentyl bromide (107-82-4) → N-isopentyl-N-methylaniline (91935-09-0) + N,N,N-trimethylanilinium bromide (16056-11-4)

Conditions	Yield
at 150 - 160℃;

N,N-dimethyl-aniline (121-69-7) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → 2-(methyl-phenyl-amino)-propionic acid ethyl ester (214709-69-0) + N,N,N-trimethylanilinium bromide (16056-11-4)

Conditions	Yield
at 125 - 130℃;

N,N-dimethyl-aniline (121-69-7) + cyanomethyl bromide (590-17-0) → N,N,N-trimethylanilinium bromide (16056-11-4)

methanol (67-56-1) + aniline (62-53-3) → N,N,N-trimethylanilinium bromide (16056-11-4) + N,N-dimethyl-aniline (121-69-7)

Conditions	Yield
at 120 - 130℃; beim Erhitzen von bromwasserstoffsaurem Anilin;

phenyltrimethylammonium tribromide (4207-56-1) + acetone (67-64-1) → N,N,N-trimethylanilinium bromide (16056-11-4)

Conditions	Yield
beim gelinden Erwaermen;

tri-N-methyl-anilinium; dibromo iodate(I) (52045-06-4) + acetone (67-64-1) → N,N,N-trimethylanilinium bromide (16056-11-4)

tri-N-methyl-anilinium; bromochloro iodate(I) + acetone (67-64-1) → N,N,N-trimethylanilinium bromide (16056-11-4)

N,N-dimethyl-aniline (121-69-7) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → N,N,N-trimethylanilinium bromide (16056-11-4)

Conditions	Yield
at 25℃;

N-methyl-N-phenacylaniline (32119-53-2) + N,N-dimethyl-aniline (121-69-7) + α-bromoacetophenone (70-11-1) → N,N,N-trimethylanilinium bromide (16056-11-4) + diphenylacyl-aniline

N,N-dimethyl-aniline (121-69-7) → N,N,N-trimethylanilinium bromide (16056-11-4) + hydrobromide of monomethylaniline

Conditions	Yield
at 150℃; beim Erhitzen von bromwasserstoffsaurem Dimethylanilin;

N,N-dimethyl-aniline (121-69-7) + α-bromoacetophenone (70-11-1) → N,N,N-trimethylanilinium bromide (16056-11-4) + N-methyl-N-phenacyl-aniline

N,N-dimethyl-aniline (121-69-7) + α-bromoacetophenone (70-11-1) → N,N-diphenacylaniline (41120-12-1) + N,N,N-trimethylanilinium bromide (16056-11-4) + N-methyl-N-phenacyl-aniline

water (7732-18-5) + phenyltrimethylammonium tribromide (4207-56-1) → N,N,N-trimethylanilinium bromide (16056-11-4)

Conditions	Yield
beim Kochen;

methanol (67-56-1) + hydrobromide of dimethylaniline → N,N,N-trimethylanilinium bromide (16056-11-4)

N,N-dimethyl-aniline (121-69-7) + α-bromoacetophenone (70-11-1) → N,N,N-trimethylanilinium bromide (16056-11-4) + methyl-phenacyl-aniline; diphenacyl-aniline

N,N,N-trimethylanilinium bromide (16056-11-4) + (4-(dimethylamino)phenyl)zinc(II) chloride (93296-10-7) → N,N-dimethyl-4-biphenylamine (1137-79-7)

Conditions	Yield
With C27H22Cl2N3NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one for 12h; Inert atmosphere; Schlenk technique; Heating;	98%
With bis(tricyclohexylphosphine)nickel(II) dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 90℃; for 8h; Negishi coupling reaction; Inert atmosphere;	84%

N,N,N-trimethylanilinium bromide (16056-11-4) + 4-methoxyphenylzinc chloride (93296-09-4) → 4-methoxylbiphenyl (613-37-6)

Conditions	Yield
With C27H22Cl2N3NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one for 12h; Solvent; Inert atmosphere; Schlenk technique; Heating;	98%
With C38H34Br2N4Ni2P2 In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 65℃; for 12h; Inert atmosphere; Schlenk technique;	94%
With C32H26ClN2NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 85℃; for 12h; Inert atmosphere;	74%

N,N,N-trimethylanilinium bromide (16056-11-4) + p-tolylzinc(II) chloride (90252-89-4) → 4-Methylbiphenyl (644-08-6)

Conditions	Yield
With C27H22Cl2N3NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one for 12h; Inert atmosphere; Heating; Schlenk technique;	90%

N-(2-methylbenzoyl)-8-aminoquinoline (1182669-71-1) + N,N,N-trimethylanilinium bromide (16056-11-4) → 2,6-dimethyl-N-(quinolin-8-yl)benzamide (1609401-42-4)

Conditions	Yield
With nickel(II) triflate; sodium carbonate; triphenylphosphine In toluene at 160℃; for 14h;	90%

N,N,N-trimethylanilinium bromide (16056-11-4) → 2C9H14N(1+)*Br6Te2(2-)

Conditions	Yield
With tellurium; bromine In acetonitrile for 24h; Heating;	88%

N,N,N-trimethylanilinium bromide (16056-11-4) → phenyltrimethylammonium hexabromoselenate

Conditions	Yield
With selenium; bromine In acetonitrile Heating;	87%

N,N,N-trimethylanilinium bromide (16056-11-4) + phenyltrimetylammonium selenocyanate → phenyltrimethylammonium hexabromoselenate

Conditions	Yield
With bromine In acetonitrile Ambient temperature;	86%

N,N,N-trimethylanilinium bromide (16056-11-4) + bis(pinacol)diborane (73183-34-3) + 2-mercaptopyridine sodium salt (13327-62-3) → 2-methylsulfanyl-pyridine (18438-38-5) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + N,N-dimethyl-aniline (121-69-7) + phenol (108-95-2)

Conditions	Yield
In acetonitrile at 30 - 35℃; for 24h; Irradiation; Inert atmosphere;	A 64% B 22% C 81% D 6%

N,N,N-trimethylanilinium bromide (16056-11-4) + bis(pinacol)diborane (73183-34-3) → 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6)

Conditions	Yield
With 10H-phenothiazine; caesium carbonate In acetonitrile for 18h; Irradiation; Sealed tube; Inert atmosphere;	76%

N,N,N-trimethylanilinium bromide (16056-11-4) + 4-n-methylphenylacetylene (766-97-2) → 4-(phenylethynyl)toluene (3287-02-3)

Conditions	Yield
With SIPr-PdCl2-Py; sodium t-butanolate In tetrahydrofuran at 45℃; for 4h; Sonogashira Cross-Coupling; Inert atmosphere;	60%

disodium closo-dodecaborate + tetrabutylammomium bromide (1643-19-2) + N,N,N-trimethylanilinium bromide (16056-11-4) + 4-nitro-benzoyl chloride (122-04-3) → [N(C4H9)4]2 (hydroxo)undecahydro-closo-dodecaborane + 2(CH3)3(C6H5)N(1+)*B12H11COC6H4NO2(2-) = [(CH3)3(C6H5)N]2(B12H11COC6H4NO2)

Conditions	Yield
In acetone byproducts: NaCl; stirring (-20°C, 30 min and 20°C, 20 h); pptn., drying; elem. anal.;	A 1% B 58%

N,N,N-trimethylanilinium bromide (16056-11-4) + 2-mercaptopyridine sodium salt (13327-62-3) → 2-methylsulfanyl-pyridine (18438-38-5) + 2-phenylsulfanylpyridine (3111-54-4) + N,N-dimethyl-aniline (121-69-7) + phenol (108-95-2)

Conditions	Yield
In acetonitrile at 30 - 35℃; for 24h; Irradiation; Inert atmosphere;	A 49% B 22% C 37% D 15%

N,N,N-trimethylanilinium bromide (16056-11-4) + 2-methylphenylzinc chloride (84109-17-1) → 2-methylbiphenyl (643-58-3)

Conditions	Yield
With C27H22Cl2N3NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one for 12h; Inert atmosphere; Heating; Schlenk technique;	46%

5-Acetyl-2-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamide (439145-80-9) + N,N,N-trimethylanilinium bromide (16056-11-4) → 2-Benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)phenyl]benzamide (439145-82-1)

Conditions	Yield
In tetrahydrofuran	42.7%

N,N,N-trimethylanilinium bromide (16056-11-4) → benzyltrimethylammonium hexafluorophosphate (6427-70-9)

Conditions	Yield
With ammonium hexafluorophosphate In water; acetone for 4h; Inert atmosphere; Schlenk technique;	40%

N,N,N-trimethylanilinium bromide (16056-11-4) + 4-methoxyphenyl magnesium bromide (13139-86-1) → 4-methoxylbiphenyl (613-37-6)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;	12%

N,N,N-trimethylanilinium bromide (16056-11-4) → 3,4-dibromo-tri-N-methyl-anilinium; bromide

Conditions	Yield
With bromine; iron at 100 - 120℃;

N,N,N-trimethylanilinium bromide (16056-11-4) → tri-N-methyl-anilinium; bromide, compound with bromine

Conditions	Yield
With bromine; acetic acid

N,N,N-trimethylanilinium bromide (16056-11-4) → 3-bromo-tri-N-methyl-anilinium; bromide

Conditions	Yield
With bromine; iron at 70℃;

N,N,N-trimethylanilinium bromide (16056-11-4) → phenyltrimethylammonium tribromide (4207-56-1)

Conditions	Yield
With bromine

N,N,N-trimethylanilinium bromide (16056-11-4) → tri-N-methyl-anilinium; dibromo iodate(I) (52045-06-4)

Conditions	Yield
With iodine(I) bromide; acetic acid

N,N,N-trimethylanilinium bromide (16056-11-4) → phenyltrimethylammonium dichloroiodate

Conditions	Yield
With Iodine monochloride; acetic acid
With iodine trichloride; acetic acid

N,N,N-trimethylanilinium bromide (16056-11-4) → tri-N-methyl-anilinium; bromochloro iodate(I)

Conditions	Yield
With Iodine monochloride; acetic acid

N,N,N-trimethylanilinium bromide (16056-11-4) → tri-N-methyl-anilinium; dichloro bromate(I) (16091-28-4)

Conditions	Yield
With chlorine; acetic acid at 60℃;

N,N,N-trimethylanilinium bromide (16056-11-4) → tri-N-methyl-anilinium; bromide, compound with iodine

Conditions	Yield
With iodine; acetic acid at 100℃;

N,N,N-trimethylanilinium bromide (16056-11-4) → methyl bromide (74-83-9) + N,N-dimethyl-aniline (121-69-7)

Conditions	Yield
at 240℃;
In dimethylsulfoxide-d6 at 120℃; for 0.333333h;

Upstream product

• 67-56-1 methanol 
• 121-69-7 N,N-dimethyl-aniline 
• 74-83-9 methyl bromide 
• 506-68-3 bromocyane 
• 506-96-7 Acetyl bromide 
• 32119-53-2 N-methyl-N-phenacylaniline 
• 70-11-1 α-bromoacetophenone 
• 7732-18-5 water 
• 4207-56-1 phenyltrimethylammonium tribromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 67-64-1 acetone 
• 52045-06-4 tri-N-methyl-anilinium; dibromo iodate(I) 
• 62-53-3 aniline 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 4207-56-1 phenyltrimethylammonium tribromide 
• 52045-06-4 tri-N-methyl-anilinium; dibromo iodate(I) 
• 16091-28-4 tri-N-methyl-anilinium; dichloro bromate(I) 
• 74-83-9 methyl bromide 
• 121-69-7 N,N-dimethyl-aniline 
• 7237-16-3 diisopropyl phenylphosphonate 
• 18438-38-5 2-methylsulfanyl-pyridine 
• 3111-54-4 2-phenylsulfanylpyridine 
• 108-95-2 phenol 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 71-43-2 benzene 
• 5396-38-3 1-(tert-butyl)-4-methoxybenzene 
• 6427-70-9 benzyltrimethylammonium hexafluorophosphate 
• 3287-02-3 4-(phenylethynyl)toluene 

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