25611-78-3

Basic information

• Product Name: 1,2-DIPHENYLETHYLAMINE
• Synonyms: 1,2-DIPHENYLETHAN-1-AMINE;1,2-DIPHENYLETHYLAMI;1-Amino-1,2-diphenylethane alpha-Benzylbenzylamine;1,2-Diphenylethylamine 97%;1,2-Diphenylethanamine;alpha,beta-diphenylethylamine;alpha-phenylbenzeneethanamine;alpha-phenyl-phenethylamin
• CAS NO: 25611-78-3
• Molecular Formula: C₁₄H₁₅N
• Molecular Weight: 197.28
• EINECS: 247-126-4
• Product Categories: Amines;C11 to C38;Nitrogen Compounds
• Mol File: 25611-78-3.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 310-311 °C750 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.02 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000575mmHg at 25°C
• Refractive Index: n20/D 1.58(lit.)
• PKA: 8.78±0.10(Predicted)
• CAS DataBase Reference: 1,2-DIPHENYLETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIPHENYLETHYLAMINE(25611-78-3)
• EPA Substance Registry System: 1,2-DIPHENYLETHYLAMINE(25611-78-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: SI2299000
• Hazardous Substances Data: 25611-78-3(Hazardous Substances Data)

Usage

Uses

1,2-Diphenylethylamine (cas# 25611-78-3) is used in the preparation of GDP-triazoles for inhibition of human α-1,3-fucosyltransferases.

General Description

(S)- and (R)-enantiomers of 1,2-diphenylethylamine are the precursors for synthesis of (S)- and (R)-1-(1,2-diphenylethyl)piperidine.

InChI:InChI=1/C14H15N/c15-14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-10,14H,11,15H2/p+1/t14-/m1/s1

Synthetic route

(1,2-diphenyl-ethyl)-carbamic acid tert-butyl ester (695231-57-3) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With water; sodium t-butanolate In tetrahydrofuran Heating;	100%

(E)-1,2-diphenyl-ethene (103-30-0) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With 10-phenyl-9-(2,4,6-trimethylphenyl)acridinium tetrafluoroborate; ammonium carbonate; 2-amino-benzenethiol In dichloromethane; chlorobenzene at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;	98%
Multi-step reaction with 2 steps 1: PrPPTNO / acetonitrile / 16 h / 30 °C / Irradiation 2: hydrogen; palladium on activated charcoal / ethyl acetate / 3 h / 50 °C View Scheme

phenyl benzyl ketone (451-40-1) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With ammonia; hydrogen In water at 130℃; for 24h; Autoclave;	93%
With ammonium formate; C25H29ClIrN2O3P at 50℃; for 18h; Leukardt-Wallach Amination; Sealed tube;	69%
With formic acid; ammonium carbonate
Stage #1: phenyl benzyl ketone With ammonium formate at 160℃; Stage #2: With hydrogenchloride In methanol
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / 6 h / 60 °C 2: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; water View Scheme

cis-stilben (645-49-8) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With 10-phenyl-9-(2,4,6-trimethylphenyl)acridinium tetrafluoroborate; ammonium carbonate; 2-amino-benzenethiol In dichloromethane; chlorobenzene at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;	93%

benzaldehyde (100-52-7) + toluene (108-88-3) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With sodium hexamethyldisilazane; caesium carbonate at 110℃; for 12h; Catalytic behavior; Reagent/catalyst; Sealed tube; Inert atmosphere; chemoselective reaction;	90%

stilbene (588-59-0) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With terephthalonitrile; ammonia In water; acetonitrile; benzene for 31h; Ambient temperature; Irradiation;	88%
With terephthalonitrile; ammonia In water; acetonitrile for 20h; Mechanism; Ambient temperature; Irradiation; other solvent; regiochemistry on photoamination of other 1,2-diarylethene via electron transfer;	46%

N-(1,2-diphenylethyl)-2-(4-methoxyphenyl)propan-2-amine → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With trifluoroacetic acid at 50℃; for 12.5h;	88%

N-(1,2-diphenyl-ethyl)-N-benzylamine (33542-84-6) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With palladium on activated charcoal; hydrogen In ethyl acetate at 50℃; for 3h;	84%

α-benzylideneamino-α-phenylacetamide (1086209-16-6) + benzyl bromide (100-39-0) → 2-oxo-2-phenylacetamide (7505-92-2) + (R,S)-1,2-diphenylethylamine (25611-78-3) + 2-Amino-2,3-diphenyl-propionamide (145143-11-9)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane Ambient temperature; phase-transfer conditions; Yields of byproduct given;	A n/a B n/a C 79%

phenylmagnesium bromide (1589-82-8) + benzonitrile (100-47-0) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
Stage #1: phenylmagnesium bromide; benzonitrile In tetrahydrofuran; diethyl ether at 100℃; for 0.166667h; Microwave irradiation; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol; diethyl ether for 0.0833333h;	76%

N-benzylidene-1,1,1-trimethylsilanamine (17599-61-0) + benzyl bromide (100-39-0) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With lithium In diethyl ether at 60℃; Barbier reaction; sonication;	73%

N-benzylidene-1,1,1-trimethylsilanamine (17599-61-0) + phenylmagnesium bromide (1589-82-8) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
In diethyl ether at 20℃; for 0.5h; Addition;	57%

benzyl bromide (100-39-0) + N-benzylidene-D,L-alanineamide (138228-58-7, 144125-68-8, 145143-06-2) → (R,S)-1,2-diphenylethylamine (25611-78-3) + α-methyl phenylalanine amide (117466-13-4) + pyruvamide (631-66-3)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane Ambient temperature; phase-transfer conditions; Yields of byproduct given;	A n/a B 55% C n/a

N-(diisobutylaluminum)benzaldehyde imine (127258-28-0) + benzylmagnesium chloride (6921-34-2) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
In tetrahydrofuran; diethyl ether -78 deg C -> room temp., 48h;	46%

benzyl bromide (100-39-0) + N-Benzylidene-methioninamide (108888-98-8, 138228-60-1, 138258-76-1, 145143-09-5) → (R,S)-1,2-diphenylethylamine (25611-78-3) + 4-Methylsulfanyl-2-oxo-butyramide + 2-Amino-2-benzyl-4-methylsulfanyl-butyramide (145174-86-3)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane Ambient temperature; phase-transfer conditions; Yields of byproduct given;	A n/a B n/a C 45%

phenyl benzyl ketone (451-40-1) + ammonium formate (540-69-2) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
at 220 - 230℃; im Druckrohr und Kochen des Reaktionsprodukts mit alkoh. Kali;
at 220 - 230℃; Verseifung des entstandenen Formylderivates durch 2-3-stdg. Kochen mit alkoh. Kali;

deoxybenzoin oxime (952-06-7) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With sodium amalgam; ethanol at 75 - 80℃; unter Abstumpfung des Alkalis mit Eisessig;
With ethanol; sodium
With sodium acetate; acetic acid; sodium sulfate elektrochemische Reduktion an einer Quecksilber-Kathode;

(1E,2E)-1,2-diphenylethane-1,2-dione bis(phenylhydrazone) (572-18-9) → (R,S)-1,2-diphenylethylamine (25611-78-3) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7)

Conditions	Yield
With acetic acid; zinc

phenylacetonitrile (140-29-4) + phenylmagnesium bromide → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With diethyl ether und Erhitzen des Reaktionsprodukts mit LiAlH4 in THF;

benzylmagnesium chloride + hydrobenzamide (92-29-5) → (R,S)-1,2-diphenylethylamine (25611-78-3) + bis(α-benzylbenzyl)amine (137406-99-6)

hydrobenzamide (92-29-5) + benzylmagnesium chloride (6921-34-2) → (R,S)-1,2-diphenylethylamine (25611-78-3) + bis(α-benzylbenzyl)amine (137406-99-6)

Conditions	Yield
With diethyl ether

benzyl bromide (100-39-0) + N-benzylidene benzylamine (780-25-6) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate 1.) CH3CN, room temp., 48 h; 2.) benzene, reflux, 3 h; Yield given. Multistep reaction;

N-benzylidene benzylamine (780-25-6) + benzyl chloride (100-44-7) → (R,S)-1,2-diphenylethylamine (25611-78-3) + 1-Benzyl-1,2-diphenylethylamine

Conditions	Yield
With hydrogenchloride; sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate 1.) CH3CN, room temp., 15 h; 2.) benzene, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

2-(1,2-Diphenylethylimino)-1,3-dithiolan (54985-68-1) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With dihydrogen peroxide; toluene-4-sulfonic acid 1) formic acid, 2h, 0-5 deg C, 2) 5h, 20 deg C; Yield given. Multistep reaction;

Benzaldoxime (932-90-1) → (R,S)-1,2-diphenylethylamine (25611-78-3) + dibenzylamine (103-49-1)

Conditions	Yield
With samarium diiodide In tetrahydrofuran; methanol for 24h; Product distribution; Ambient temperature; other compounds with nitrogen functional groups, olefines and carbonyl compounds, var. times;	A 75 % Chromat. B 25 % Chromat.

N-(diphenylmethylidene)-1,2-diphenylethylamine (27962-33-0) → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With hydrogenchloride

deoxybenzoin oxime (952-06-7) + ethanol (64-17-5) + acetic acid (64-19-7) + sodium amalgam → (R,S)-1,2-diphenylethylamine (25611-78-3)

α-nitro-dibenzyl → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With hydrogenchloride; tin

(+-)-2.3-diphenyl-propionamide → (R,S)-1,2-diphenylethylamine (25611-78-3)

Conditions	Yield
With sodium hypochlorite

(R,S)-1,2-diphenylethylamine (25611-78-3) + acetyl chloride (75-36-5) → N-(1,2-diphenylethyl)acetamide (21511-90-0)

Conditions	Yield
With sodium hydroxide In water at 0℃; for 1h;	99%
With sodium hydroxide at 0℃; for 2h;

(R,S)-1,2-diphenylethylamine (25611-78-3) + 4-bromo-2-fluoronitrobenzene (321-23-3) → 5-bromo-N-(1,2-diphenylethyl)-2-nitroaniline

Conditions	Yield
With potassium carbonate In acetonitrile at 70℃;	99%

(R,S)-1,2-diphenylethylamine (25611-78-3) + benzoyl chloride (98-88-4) → N-(1,2-diphenylethyl)benzamide (66730-28-7)

Conditions	Yield
With sodium hydroxide In water at 0℃; for 1h;	98%
With diethyl ether

maleic anhydride (108-31-6) + (R,S)-1,2-diphenylethylamine (25611-78-3) → (E)-3-(1,2-Diphenyl-ethylcarbamoyl)-acrylic acid (4812-56-0)

Conditions	Yield
In diethyl ether at 20℃; for 1h;	97%

(R,S)-1,2-diphenylethylamine (25611-78-3) + formic acid ethyl ester (109-94-4) → N-(1,2-diphenylethyl)formamide (93172-46-4)

Conditions	Yield
for 24h; Heating;	94%

(R,S)-1,2-diphenylethylamine (25611-78-3) + methyl 9H-pyrido[3,4-b]indole-1-carboxylate (3464-66-2) → N-(1,2-diphenylethyl)-9H-pyrido[3,4-b]indole-1-carboxamide

Conditions	Yield
With 2-hydroxypyridin In 1,4-dioxane at 120℃; for 17h;	92%

(R,S)-1,2-diphenylethylamine (25611-78-3) + 3-oxo-4-aza-5α-androstane-17β-carboxylic acid (103335-55-3) → N-(1,2-diphenylethyl)-3-oxo-4-aza-5α-androstane-17β-carboxamide

Conditions	Yield
With phosphorocyanidate; triethylamine In dichloromethane for 24h; Ambient temperature;	91%

(R,S)-1,2-diphenylethylamine (25611-78-3) + 2-[(3,4-dichlorophenyl)amino]-1,3-thiazole-4-carboxylic acid (952182-44-4) → N-(1,2-diphenylethyl) 2-(3,4-dichlorophenylamino)thiazole-4-carboxamide

Conditions	Yield
Stage #1: 2-[(3,4-dichlorophenyl)amino]-1,3-thiazole-4-carboxylic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: (R,S)-1,2-diphenylethylamine In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere;	91%

(R,S)-1,2-diphenylethylamine (25611-78-3) + 4-methoxy-benzoyl chloride (100-07-2) → N-(1,2-diphenylethyl)-p-methoxy benzamide (77198-89-1)

Conditions	Yield
With sodium hydroxide In water at 0℃; for 1h;	90%

(R,S)-1,2-diphenylethylamine (25611-78-3) + (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (26250-84-0) → C25H32N2O3

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	90%

(R,S)-1,2-diphenylethylamine (25611-78-3) + (R)-α-<1-(9-Anthryl)-2,2,2-trifluoroethoxy>acetic acid (161905-71-1) → N-(1,2-Diphenylethyl)-α-<1-(9-anthryl)-2,2,2-trifluoroethoxy>acetamide (77507-25-6)

Conditions	Yield
With N-(Ethoxycarbonyl)-2-ethoxy-1,2-dihydroquinone In chloroform	85%

carbon monoxide (201230-82-2) + (R,S)-1,2-diphenylethylamine (25611-78-3) + 2-Iodobenzyl bromide (40400-13-3) → 2-(1,2-diphenyl-ethyl)-2,3-dihydro-isoindol-1-one

Conditions	Yield
With bi(8F-5acetoxy-5H-10oxa-4b-aza-5Pd-indeno[2,1-a]inden-5-yl); potassium carbonate In N,N-dimethyl-formamide at 80℃; under 760 Torr; for 12h;	85%

2,6-dichloro-9-(4-thio-β-D-ribofuranosyl)purine (900810-23-3) + (R,S)-1,2-diphenylethylamine (25611-78-3) → 2-chloro-6-(1,2-diphenylethyl)amino-9-(4-thio-β-D-ribofuranosyl)purine

Conditions	Yield
With triethylamine In ethanol at 20℃;	85%

pyridine-2-carbaldehyde (1121-60-4) + (R,S)-1,2-diphenylethylamine (25611-78-3) → (E)-N-(1,2-diphenylethyl)-1-(pyridin-2-yl)methanimine

Conditions	Yield
In dichloromethane at 20℃; for 12h; Molecular sieve;	83%

(R,S)-1,2-diphenylethylamine (25611-78-3) + phenylacetyl chloride (103-80-0) → N-<(1,2-diphenylethyl)phenyl>acetamide (77414-35-8)

Conditions	Yield
With sodium hydroxide In water at 0℃; for 1h;	82%

1-(furan-2-yl)-2,2-dimethylpropan-1-one (4208-54-2) + (R,S)-1,2-diphenylethylamine (25611-78-3) → (1,2-diphenylethyl)(1-furan-2-yl-2,2-dimethyl-propylidene)amine

Conditions	Yield
With titanium tetrachloride; triethylamine In water; 1,2-dichloro-ethane at 0℃; for 15h; Inert atmosphere; Reflux;	81%

4-(4-piperidinomethyl-pyridin-2-yloxy)-cis-2-butenylamine (103922-89-0) + (R,S)-1,2-diphenylethylamine (25611-78-3) → N-(1,2-Diphenylethyl)-N'-[4-(4-piperidinomethyl-pyridin-2-yloxy)-cis-2-butenyl]urea

Conditions	Yield
	80%

methyl-3-pyridylketone (350-03-8) + (R,S)-1,2-diphenylethylamine (25611-78-3) → 1,2-diphenyl-N-(1-(pyridin-3-yl)ethylidene)ethanamine

Conditions	Yield
With titanium(IV) tetraethanolate In water; 1,2-dichloro-ethane for 8h; Reflux; Inert atmosphere;	80%

Succinimide (123-56-8) + (R,S)-1,2-diphenylethylamine (25611-78-3) + copper (12775-96-1, 15158-11-9, 15721-63-8, 16941-75-6, 17493-86-6, 19498-52-3, 20499-83-6, 20499-84-7, 20499-85-8, 20499-86-9, 20573-10-8, 20573-11-9, 21595-51-7, 21595-52-8, 22206-52-6, 26445-28-3, 28959-95-7, 37362-93-9, 39417-05-5, 54603-16-6, 54603-23-5, 54603-32-6, 54603-40-6, 54603-48-4, 54603-81-5, 54603-89-3, 56316-56-4, 95985-91-4, 122297-32-9, 7440-50-8) → trans-[Cu(succinimidate)2(R-1,2-diphenylethylamine)(S-1,2-diphenylethylamine)]

Conditions	Yield
In ethanol mixt. stirred for 2 h at 50°C; filtered; dried overnight; elem.anal.;	75.8%

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 540-69-2 ammonium formate 
• 92-29-5 hydrobenzamide 
• 6921-34-2 benzylmagnesium chloride 
• 588-59-0 stilbene 
• 780-25-6 N-benzylidene benzylamine 
• 100-44-7 benzyl chloride 
• 932-90-1 Benzaldoxime 
• 127258-28-0 N-(diisobutylaluminum)benzaldehyde imine 
• 93172-46-4 N-(1,2-diphenylethyl)formamide 
• 100-52-7 benzaldehyde 
• 98-88-4 benzoyl chloride 
• 1589-82-8 phenylmagnesium bromide 
• 100-47-0 benzonitrile 

Downstream Products

• 553-06-0 N-(1,2-diphenyl-ethyl)-nicotinamide 
• 3847-48-1 N,N-diethyl-N'-bibenzyl-α-yl-ethylenediamine 
• 71056-06-9 1,2-Diphenylethylisothiocyanate 
• 33542-84-6 N-(1,2-diphenyl-ethyl)-N-benzylamine 
• 99765-20-5 N-(1,2-Diphenylethyl)-2-benzothiazolamin 
• 77414-38-1 N-(1,2-diphenethyl)-3,4-dimethoxyphenacetamide 
• 74619-81-1 N-benzylidene-(-)-1,2-diphenylethylamine 
• 72624-40-9 4,6,7-triphenyl-1,2,5-thiadiazolo<3,4-c>pyridine 
• 28057-75-2 (1-isocyanatoethane-1,2-diyl)dibenzene 
• 21735-62-6 N-(1,2-Diphenyl-ethyl)-2,2,2-trifluoro-acetamide 
• 77988-84-2 N-(1,2-diphenethyl)acetimidoyl chloride 
• 77988-83-1 N-(1,2-diphenylethyl)benzimidoyl chloride 
• 102453-48-5 N,N-diethyl-β-alanine bibenzyl-α-ylamide 

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