89996-00-9

Basic information

• Product Name: Phosphonium, (2-aminoethyl)triphenyl-, bromide
• CAS NO: 89996-00-9
• Molecular Formula: C20H21NP.Br
• Molecular Weight: 467.183
• Mol File: 89996-00-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Phosphonium, (2-aminoethyl)triphenyl-, bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonium, (2-aminoethyl)triphenyl-, bromide(89996-00-9)
• EPA Substance Registry System: Phosphonium, (2-aminoethyl)triphenyl-, bromide(89996-00-9)

Safety Data

• Hazardous Substances Data: 89996-00-9(Hazardous Substances Data)

Usage

General Description

Phosphonium, (2-aminoethyl)triphenyl-, bromide is a chemical compound with the molecular formula C20H24BrN. It is a phosphonium salt that contains a central phosphorus atom bonded to three phenyl groups and a bromide ion. The compound also features an aminoethyl group, which contains both an amine and an ethyl functional group. It is commonly used in organic synthesis and as a reactant in the preparation of various organic compounds. Phosphonium, (2-aminoethyl)triphenyl-, bromide has applications in the pharmaceutical and chemical industries, where it is used in the synthesis of various drugs and other organic compounds.

Synthetic route

2-bromoethylamine (107-09-5) + triphenylphosphine (603-35-0) → (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9)

Conditions	Yield
In acetonitrile for 24h; Reflux;	88%

2-bromoethylamine hydrobromide (2576-47-8) + triphenylphosphine (603-35-0) → (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9)

Conditions	Yield
In acetonitrile for 18h; Reflux;	68%
In acetonitrile for 15h; Reflux; Inert atmosphere;	40%
In acetonitrile for 15h; Heating;	19%

satraplatin + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C41H64Cl2N4O5PPt(1+)*Cl(1-)

Conditions	Yield
Stage #1: satraplatin With HATU In N,N-dimethyl-formamide for 0.333333h; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #3: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5.5h;	94%

5-amino-1-naphthalenesulfonyl chloride + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C30H28N2O2PS(1+)

Conditions	Yield
Stage #1: (2-aminoethyl)triphenylphosphonium bromide salt With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: 5-amino-1-naphthalenesulfonyl chloride In dichloromethane	94%

cyclohexa-2,4-dien-1-ylmethyl (2,5-dioxopyrrolidin-1-yl) carbonate + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → (2-(((cyclohexa-2,4-dien-1-ylmethoxy)carbonyl)amino)ethyl)triphenylphosphonium bromide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 4h;	91%

2,5-dioxopyrrolidin-1-yl ((1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)methyl) carbonate + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → (2-((((1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)methoxy)carbonyl)amino)ethyl)triphenylphosphonium bromide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 4h;	87%

(4R*,5R*)-5-diisopropyloxyphosphoryl-5-methyl-4-(succinimidyloxycarbonyloxymethyl)-1-pyrroline N-oxide + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → (4R*,5R*)-5-(diisopropyloxyphosphoryl)-5-methyl-4-[({[2-(triphenylphosphonio)ethyl]carbamoyl}oxy)methyl]pyrroline N-oxide bromide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;	86%

hex-5-ynoic acid (53293-00-8) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → (2-(hex-5-ynamido)ethyl)triphenylphosphonium bromide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 24h;	84%

((2-(2-(fluoro-18F)ethoxy)ethyl)sulfonyl)ethane + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C26H32(18)FNO3PS(1+)*Br(1-)

Conditions	Yield
at 45 - 65℃; pH=8.5;	81%

Boc-Glu(OBzl)-OH (13574-13-5) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C37H42N2O5P(1+)*Br(1-)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	76%

C20H16N2O3S (1443663-75-9) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C40H35N3O2PS(1+) (1443663-69-1)

Conditions	Yield
Stage #1: C20H16N2O3S With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran for 10h; Inert atmosphere;	70%

(2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) + 2-carboxy-4,5,6-trihydrothiopheno<3,2-d><1>benzazepine → (2-(5,6-dihydro-4H-benzo[b]thieno[2,3-d]azepine-2-carboxamido)ethyl)triphenylphosphonium bromide

Conditions	Yield
Stage #1: 2-carboxy-4,5,6-trihydrothiopheno<3,2-d><1>benzazepine With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.5h; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt In N,N-dimethyl-formamide at 20℃;	70%

(2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → 4-MitoDEPMPO

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	69%

5-diethoxyphosphoryl-4-succinimidyloxycarbonyloxymethyl-5-methyl-1-pyrroline-N-oxide + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C31H39N2O6P2(1+)*Br(1-)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	69%

(Z)-5-[{5-(2,6-dichlorobenzylsulfonyl)-2-oxoindolin-3-ylidene}methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (477574-82-6) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → (Z)-(2-(5-((5-(2,6-dichlorobenzylsulfonyl)-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)ethyl)triphenylphosphonium bromide

Conditions	Yield
Stage #1: (Z)-5-[{5-(2,6-dichlorobenzylsulfonyl)-2-oxoindolin-3-ylidene}methyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 0.5h; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt In N,N-dimethyl-formamide at 25℃;	68%

cyanoacetic acid (372-09-8) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → Br(1-)*C23H22N2OP(1+)

Conditions	Yield
Stage #1: cyanoacetic acid; (2-aminoethyl)triphenylphosphonium bromide salt With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane for 0.333333h; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12.3333h;	68%

C29H29N3O7 + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C49H48N4O6P(1+)*Br(1-)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Inert atmosphere;	65%

7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid (779-27-1) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C30H25NO4P(1+)*Br(1-)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	64.47%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	64.47%

C14H13NO3 (1290638-60-6) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → Br(1-)*C34H32N2O2P(1+)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane for 16h; Inert atmosphere;	64%

C14H13NO3 (1290638-60-6) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C34H32N2O2P(1+)

Conditions	Yield
Stage #1: C14H13NO3 With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt In dichloromethane for 16h;	64%

benzothiazole-6-carboxylic acid (3622-35-3) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C28H24N2OPS(1+)*Br(1-) (1609946-43-1)

Conditions	Yield
Stage #1: benzothiazole-6-carboxylic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt In dichloromethane at 20℃; for 16h; Inert atmosphere;	63%

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid (84358-13-4) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → Br(1-)*C31H38N2O3P(1+)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; ethyl cyanoglyoxylate-2-oxime In N,N-dimethyl-formamide at 20℃; for 11h;	63%

3-(triethoxypropyl) isocyanate (24801-88-5) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C30H42N2O4PSi(1+)*Br(1-)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane Inert atmosphere;	62.1%

4-(3-hydroxy-4-oxo-4H-benzo[g]chromen-2-yl)benzoic acid + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → (2-(4-(3-hydroxy-4-oxo-4H-benzo[g]chromen-2-yl)benzamido)ethyl)triphenylphosphonium bromide

Conditions	Yield
Stage #1: 4-(3-hydroxy-4-oxo-4H-benzo[g]chromen-2-yl)benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 2h; Darkness; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt In N,N-dimethyl-formamide at 20℃; for 24h; Darkness;	60%
Stage #1: 4-(3-hydroxy-4-oxo-4H-benzo[g]chromen-2-yl)benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h; Darkness; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt In N,N-dimethyl-formamide at 20℃; for 24h;

(2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) + 7-(diethylamino)coumarin-3-carboxylic acid (50995-74-9) → C34H34N2O3P(1+)*Br(1-)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	60%

1-(5-carboxypentyl)-2,3,3-trimethylindoleninium bromide + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C37H43N2OP(2+)*2Br(1-)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 20h;	54%

C29H28N2O4 + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C49H47N3O3P(1+)

Conditions	Yield
Stage #1: C29H28N2O4 With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt In N,N-dimethyl-formamide at 20℃; for 12h;	53.5%

3-(bis(2-((2-(ethylthio)ethyl)thio)ethyl)amino)-10-(4-(2-carboxmethoxy)-2,6-dimethylphenyl)-5,5-difluoro-7-methoxy-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide (1309582-38-4) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → ((C6H5)3PCH2CH2NHCOCH2OC6H2(CH3)2C(C4H2N(N(CH2CH2SCH2CH2SCH2CH3)2))(C4H2NOCH3))BF2(1+) (1309582-39-5)

Conditions

Yield

With CH3CH2N(CH(CH3)2)2; [C5H3N4OC(N(CH3)2)2]PF6 In dichloromethane (N2); dissolving boron compd. and HATU in anhyd. CH2Cl2, purging with N2for 5 min, keeping for 20 min, addn. of phosphonium deriv., stirring fo r 20 min, addn. of amine deriv., stirring at room temp. overnight; evapn., chromy. (silica, 0.25% ethyl acetate and 0.25% methanol in CH2Cl2), chromy. (silica, 0.5% ethyl acetate and 0.5% methanol in CH2Cl2), chromy. (silica, 0.25% ethyl acetate and 0.25% methanol in CH2Cl2 to 1% methanol in CH2Cl2), NMR and MS;

48%

[4'-(2,4-dinitrobenzenesulfonyloxy)-2,2':6',2''-terpyridine-6,6''-diyl]bis(methylenenitrilo)tetrakis(acetic acid) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C51H46N8O14PS(1+)*Br(1-)

Conditions	Yield
Stage #1: [4'-(2,4-dinitrobenzenesulfonyloxy)-2,2':6',2''-terpyridine-6,6''-diyl]bis(methylenenitrilo)tetrakis(acetic acid) With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt In N,N-dimethyl-formamide for 2h;	46.5%

[4'-(p-nitrophenylthio)methylene-2,2':6',2''-terpyridine-6,6''-diyl]bis(methylenenitrilo)tetrakis(acetic acid) + (2-aminoethyl)triphenylphosphonium bromide salt (89996-00-9) → C52H49N7O9PS(1+)*Br(1-)

Conditions	Yield
Stage #1: [4'-(p-nitrophenylthio)methylene-2,2':6',2''-terpyridine-6,6''-diyl]bis(methylenenitrilo)tetrakis(acetic acid) With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: (2-aminoethyl)triphenylphosphonium bromide salt With triethylamine In N,N-dimethyl-formamide for 2h;	45.9%

Upstream product

• 107-09-5 2-bromoethylamine 
• 603-35-0 triphenylphosphine 
• 2576-47-8 2-bromoethylamine hydrobromide 

Downstream Products

• 1443663-69-1 C₄₀H₃₅N₃O₂PS⁽¹⁺⁾ 
• 1254044-36-4 mito-apocynin acetate 
• 4335-60-8 (E)-cinnamylamine 
• 4226-59-9 (Z)-3-phenylprop-2-en-1-amine 
• 4360-51-4 cinnamylamine 

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