rac-1,2-diphenylethylene-1,2-diamine
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Stage #1: rac-1,2-diphenylethylene-1,2-diamine With di-μ-Cl-bis{(SCRN)2-[1(N-i-PrNH)Et]Ph-C,N}diPd(II) In methanol for 1h; Substitution; Stage #2: With hydrogenchloride In dichloromethane for 0.0833333h; Decomposition; | 85% |
60% | |
With L-(+)-tartaric acid Inert atmosphere; | 38% |
benzylidenamine
A
(S,S)-1,2-diphenyl-1,2-diaminoethane
B
(R,R)-1,2-diphenylethylenediamine
Conditions | Yield |
---|---|
Stage #1: benzylidenamine With (5R,5'R)-4,4,4',4'-tetrakis(2,5-dimethylphenyl)-5,5'-diphenyl-2,2'-bi(1,3,2-dioxaborolane) In tetrahydrofuran; methanol at 20 - 30℃; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In methanol; water pH=Ca. 3; Catalytic behavior; Reagent/catalyst; Solvent; | A n/a B 80% |
Stage #1: benzylidenamine With (5R,5'R)-5,5'-diphenyl-4,4,4',4'-tetra-o-tolyl-2,2'-bi(1,3,2-dioxaborolane) In tetrahydrofuran; methanol at 20℃; for 24h; Stage #2: With hydrogenchloride In methanol Reagent/catalyst; enantioselective reaction; | A n/a B n/a |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; water at 0 - 5℃; | 66% |
1,2-Diphenyl-N,N'-bis-[1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylidene]-ethane-1,2-diamine
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
With hydroxylamine acetate In ethanol for 24h; Heating; | 50% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid | 49% |
(+)-(1S,2S)-N-[(R)-α-acetoxyphenylacetyl]-N'-benzoyl-1,2-diamino-1,2-diphenylethane
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid for 26h; Heating; | 34% |
(+)-(1S,2S)-1,2-diphenylethane-1,2-diazide
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethyl acetate under 38000 Torr; Yield given; | |
With lithium aluminium tetrahydride In diethyl ether |
(S,S)-1,2-diphenyl-1,2-diaminoethane
(S,S)-1,2-diphenyl-1,2-diaminoethane
benzildioxime
A
(S,S)-1,2-diphenyl-1,2-diaminoethane
B
meso-1,2-diphenyl-1,2-diaminoethane
C
(R,R)-1,2-diphenylethylenediamine
Conditions | Yield |
---|---|
With sodium In ethanol for 0.166667h; Heating; Yield given. Yields of byproduct given; |
1,2-Diphenylethylenediamine
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
via co-crystalization with N*-chiral dimeric ortho-palladated matrix SCRN-L>PdCl>2 L=2-<1-(N-isopropylamino)ethyl>phenyl-CN; |
A
(S,S)-1,2-diphenyl-1,2-diaminoethane
1,2-diphenylethane-1,2-diamine
Conditions | Yield |
---|---|
With water Durch fraktionierte Krystallisation; |
(-)-(4S,5S)-4,5-dihydro-2,4,5-triphenyl-1H-imidazole
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: NaOAc 1.2: 95 percent / HCl / H2O 2.1: 49 percent / HBr; AcOH View Scheme |
isoamarine
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: NaOAc 1.2: 95 percent / HCl / H2O 2.1: 49 percent / HBr; AcOH View Scheme | |
Multi-step reaction with 3 steps 1: 68 percent / dicyclohexylcarbodiimide / CH2Cl2 / -20 - 20 °C 2: 92 percent / HCl / H2O; tetrahydrofuran / 2 h / Heating 3: 34 percent / aq. HBr / acetic acid / 26 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 1) Ac2O, 2) dil. HCl, 3) aq. HBr / 3) AcOH, reflux 2: 60 percent View Scheme |
(-)-(4S,5S)-1-[(R)-α-acetoxyphenylacetyl]-4,5-dihydro-2,4,5-triphenyl-1H-imidazole
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / HCl / H2O; tetrahydrofuran / 2 h / Heating 2: 34 percent / aq. HBr / acetic acid / 26 h / Heating View Scheme |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HCl / H2O; tetrahydrofuran / 2 h / Heating 2: 34 percent / aq. HBr / acetic acid / 26 h / Heating View Scheme |
DL-(4R,5S)-2,4,5-triphenyl-4,5-dihydro-1H-imidazole
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 70 percent / aq. NaOH / bis-(2-hydroxy-ethyl) ether / 0.75 h / 155 °C 2: 68 percent / dicyclohexylcarbodiimide / CH2Cl2 / -20 - 20 °C 3: 92 percent / HCl / H2O; tetrahydrofuran / 2 h / Heating 4: 34 percent / aq. HBr / acetic acid / 26 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 87 percent / aq. NaOH / bis-(2-hydroxy-ethyl) ether / 155 °C 2: 1) Ac2O, 2) dil. HCl, 3) aq. HBr / 3) AcOH, reflux 3: 60 percent View Scheme |
(R,R)-(+)-4,5-diphenyl-1,3,2-dioxathiolan-2-one
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 81 percent / LiN3 / dimethylformamide / 120 °C 2: pyridine 3: LiN3 / dimethylformamide / 120 °C 4: H2 / 10percent Pd/C / ethyl acetate / 38000 Torr View Scheme |
(R,R)-hydroxybenzoin
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 100 percent / SOCl2 / CCl4 / Heating 2: 81 percent / LiN3 / dimethylformamide / 120 °C 3: pyridine 4: LiN3 / dimethylformamide / 120 °C 5: H2 / 10percent Pd/C / ethyl acetate / 38000 Torr View Scheme | |
Multi-step reaction with 3 steps 1: pyridine 2: NaN3 / dimethylformamide 3: LiAlH4 / diethyl ether View Scheme |
(1R,2S)-2-azido-1,2-diphenylethan-1-ol
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine 2: LiN3 / dimethylformamide / 120 °C 3: H2 / 10percent Pd/C / ethyl acetate / 38000 Torr View Scheme |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LiN3 / dimethylformamide / 120 °C 2: H2 / 10percent Pd/C / ethyl acetate / 38000 Torr View Scheme |
(-)-(1R,2R)-1,2-diphenyl-1,2-ditosyloxyethane
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaN3 / dimethylformamide 2: LiAlH4 / diethyl ether View Scheme |
(E)-1,2-diphenyl-ethene
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) NaN3, Fe2(SO4)3, (ii) H2O2, (iii) Sn, aq. HCl View Scheme |
Conditions | Yield |
---|---|
In ethanol; water Equilibrium constant; enantioselective reaction; |
C14H16N2*C47H38O4
A
(S,S)-1,2-diphenyl-1,2-diaminoethane
B
[(4R,5R)-2,2-dimethyl-1,3-dioxolan-4,5-diyl]bis(dinaphthalen-2-ylmethanol)
Conditions | Yield |
---|---|
In chloroform-d1 Equilibrium constant; |
1,2-Diphenylethylenediamine
A
(S,S)-1,2-diphenyl-1,2-diaminoethane
B
(R,R)-1,2-diphenylethylenediamine
Conditions | Yield |
---|---|
With chiral stationary phase including isopropyl-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 0℃; Purification / work up; |
N-benzoyl-N'-benzylidene-meso-1,2-diphenyl-ethylendiamine
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
With sulfuric acid for 1h; Reflux; |
A
(S,S)-1,2-diphenyl-1,2-diaminoethane
B
(R,R)-1,2-diphenylethylenediamine
Conditions | Yield |
---|---|
With barium(II) hydroxide In water at 80℃; for 23h; Overall yield = 93 %; enantioselective reaction; | A n/a B n/a |
2,2-ppirocyclohexane-4,5-diphenyl-2H-imidazole
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: ammonia; lithium / tetrahydrofuran; ethanol / -78 - -65 °C / Inert atmosphere 1.2: -65 °C / Inert atmosphere 1.3: 0 °C / Inert atmosphere 2.1: ethanol / 20 - 70 °C 3.1: sodium hydroxide / water; dichloromethane / 0 - 5 °C View Scheme |
pyridine-2-carbaldehyde
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
In benzene for 2h; Heating; | 100% |
In methanol | 22% |
formaldehyd
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
With formic acid Heating; | 100% |
P,P-dichlorophenylphosphine oxide
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
carbon disulfide
(S,S)-1,2-diphenyl-1,2-diaminoethane
(4S,5S)-4,5-diphenylimidazolidine-2-thione
Conditions | Yield |
---|---|
In ethanol at 95℃; for 4h; Inert atmosphere; | 100% |
In ethanol at 95℃; |
(S,S)-1,2-diphenyl-1,2-diaminoethane
(R)-2-phenyl-N-tosylaziridine
4-methyl-N-[(1R)-2-{[(1S,2S)-2-{[(2R)-2-(4-methylbenzenesulfonamido)-2-phenylethyl]amino}-1,2-diphenylethy]amino}-1-phenylethyl]benzene-1-sulfonamido
Conditions | Yield |
---|---|
In acetonitrile Reflux; | 100% |
In acetonitrile for 72h; Inert atmosphere; Reflux; | 74% |
In acetonitrile for 72h; Reflux; | 74% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 25℃; for 17h; Inert atmosphere; Schlenk technique; | A 100% B n/a |
2-bromoanisole
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 20℃; for 1.5h; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: 2-bromoanisole In toluene at 120℃; for 9h; Inert atmosphere; Schlenk technique; Glovebox; | 100% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
In ethanol at 20℃; for 20h; Inert atmosphere; Molecular sieve; | 100% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
In ethanol at 20℃; for 20h; Inert atmosphere; Molecular sieve; | 100% |
(R)-camphorquinone
(S,S)-1,2-diphenyl-1,2-diaminoethane
(1R,4S,5S)-4,5-diphenyl-1,11,11-trimethyl-3,6-diazatricyclo[6.2.1.02,7]undeca-2,6-diene
Conditions | Yield |
---|---|
In benzene Condensation; Heating; | 99% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Glyoxilic acid
Conditions | Yield |
---|---|
In dichloromethane for 16h; | 99% |
In dichloromethane for 16h; | 99% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
In dichloromethane for 0.5h; | 99% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
In dichloromethane for 0.5h; | 99% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
In dichloromethane for 0.5h; | 99% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
With hydrogen In dichloromethane for 1h; | 99% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
3,4-dimethoxybenzene-1-sulfonyl chloride
(S,S)-N-(2-amino-1,2-diphenyl-ethyl)-3,4-dimethoxy-benzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 99% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
chloroformic acid ethyl ester
diethyl ((1S,2S)-1,2-diphenylethane-1,2-diyl)dicarbamate
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 4h; | 98% |
In ethanol Ambient temperature; | |
With pyridine In benzene for 2h; |
(S,S)-1,2-diphenyl-1,2-diaminoethane
2-formylbenzene boronic acid
(R)-1,1'-Bi-2-naphthol
Conditions | Yield |
---|---|
In chloroform at 20℃; for 1h; | 98% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
2-bromo-4-methyl-1,1'-biphenyl
C27H26N2
Conditions | Yield |
---|---|
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; for 48h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere; | 98% |
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 10h; Inert atmosphere; | 86.3% |
di-μ-chlorobis[1-[2-(di-tert-butulphosphino)phenyl]ethyl-C1,P]dipalladium(II)
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
In methanol (Ar, Schlenk) a suspn. of dimer and diamine in anhyd. CH3OH was stirred for 1 h at room temp.; filtered, evapd. to dryness; | 98% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
ethyl acetimidate hydrochloride
(4S,5S)-2-methyl-4,5-diphenyl-4,5-dihydro-1H-imidazole
Conditions | Yield |
---|---|
In ethanol at 0 - 20℃; for 12h; Inert atmosphere; | 98% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Glyoxilic acid
Conditions | Yield |
---|---|
With N-Bromosuccinimide In methanol at 20℃; for 1h; Inert atmosphere; | 98% |
Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane; Glyoxilic acid In methanol Stage #2: With N-Bromosuccinimide | 98% |
With N-Bromosuccinimide |
Pentafluoropyridine
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux; regioselective reaction; | 98% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
Conditions | Yield |
---|---|
In (2)H8-toluene at 20℃; for 2h; | 98% |
trifluoromethylsulfonic anhydride
(S,S)-1,2-diphenyl-1,2-diaminoethane
(1S,2S)-1,2-diphenyl-N,N'-bis(trifluoromethanesulfonyl)ethane-1,2-diamine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 97% |
With dmap; triethylamine In dichloromethane at -78 - 20℃; | 69% |
With dmap; triethylamine In dichloromethane at -78 - 20℃; for 0.5h; Inert atmosphere; | 57% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
phenyl isocyanate
Conditions | Yield |
---|---|
In dichloromethane Ambient temperature; | 97% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
5-bromo-3-tert-butyl-2-hydroxybenzaldehyde
Conditions | Yield |
---|---|
In ethanol for 1h; Heating; | 97% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
salicylaldehyde
N,N'-Disalicyliden-meso-1,2-diphenylethylendiamin
Conditions | Yield |
---|---|
With sodium sulfate In methanol for 12h; Ambient temperature; | 97% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
2-Hydroxy-2'-methoxy-<1,1'-biphenyl>-3-carboxaldehyde
Conditions | Yield |
---|---|
In ethanol at 20℃; for 24h; | 97% |
(S,S)-1,2-diphenyl-1,2-diaminoethane
5-chloro-5H-dibenzo[a,d]cycloheptene
(S,S)-N,N'-bis(5H-dibenzo[a,d]cyclohepten-5-yl)-1,2-diphenyl-1,2-ethylenediamine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 0.166667h; Heating; | 97% |
Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane; 5-chloro-5H-dibenzo[a,d]cycloheptene In dichloromethane at 20℃; for 2.16667h; Stage #2: With potassium carbonate In dichloromethane; water | 97% |
In dichloromethane at 20℃; for 2.16667h; | 97% |
The (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine, with the CAS registry number 29841-69-8, is also known as 1,2-Ethanediamine, 1,2-diphenyl-, (1S,2S)-. It belongs to the product categories of Chiral; Chiral reagent; Chiral compounds; Amines (Chiral); Analytical Chemistry; Asymmetric Synthesis; Chiral Building Blocks; e.e. / Absolute Configuration Determination (NMR); Enantiomer Excess & Absolute Configuration Determination; Synthetic Organic Chemistry; Amines and Derivatives; Chiral chemicals; Chiral Compound. Its IUPAC name is called (1S,2S)-1,2-diphenylethane-1,2-diamine. You should store it in a tightly-sealed container(2 ºC -8 ºC) which is white to light yellow crystal powder.
Physical properties of (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine: (1)ACD/LogP: 1.60; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 4; (5)#Freely Rotating Bonds: 5; (6)Index of Refraction: 1.619; (7)Molar Refractivity: 67.36 cm3; (8)Molar Volume: 191.8 cm3; (9)Surface Tension: 50.5 dyne/cm; (10)Density: 1.106 g/cm3; (11)Flash Point: 199.9 °C; (12)Enthalpy of Vaporization: 59.89 kJ/mol; (13)Boiling Point: 353.9 °C at 760 mmHg; (14)Vapour Pressure: 3.48E-05 mmHg at 25°C.
Uses of (1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine: it is widely used in asymmetric synthesis and optical resolution, such as asymmetric hydroxylation of olefins, asymmetric aldol condensation, asymmetric Diels-Alder reaction, asymmetric carbonyl allylation reaction.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes and may destroy living tissue on contact. Causes burns. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)C(C(C2=CC=CC=C2)N)N
(2)Isomeric SMILES: C1=CC=C(C=C1)[C@@H]([C@H](C2=CC=CC=C2)N)N
(3)InChI: InChI=1S/C14H16N2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14H,15-16H2/t13-,14-/m0/s1
(4)InChIKey: PONXTPCRRASWKW-KBPBESRZSA-N
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