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[ CAS No. 58520-04-0 ] {[proInfo.proName]}

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Chemical Structure| 58520-04-0
Chemical Structure| 58520-04-0
Structure of 58520-04-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 58520-04-0 ]

CAS No. :58520-04-0 MDL No. :MFCD08460191
Formula : C16H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 272.34 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 58520-04-0 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.25
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 79.1
TPSA : 70.5 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 1.34
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 1.72
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 1.88

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.888 mg/ml ; 0.00326 mol/l
Class : Soluble
Log S (Ali) : -2.42
Solubility : 1.03 mg/ml ; 0.00378 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.55
Solubility : 0.00769 mg/ml ; 0.0000282 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.41

Safety of [ 58520-04-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 58520-04-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 58520-04-0 ]

[ 58520-04-0 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 90-02-8 ]
  • [ 58520-04-0 ]
  • C30H28N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With magnesium sulfate In methanol at 50℃; for 1h;
  • 2
  • [ 358-23-6 ]
  • [ 58520-04-0 ]
  • N-[(1S,2S)-1,2-Bis-(4-methoxy-phenyl)-2-trifluoromethanesulfonylamino-ethyl]-C,C,C-trifluoro-methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine In dichloromethane
  • 3
  • d,l-1,2-diamino-1,2-bis(4-methoxyphenyl)ethane [ No CAS ]
  • [ 58520-04-0 ]
YieldReaction ConditionsOperation in experiment
98 % ee With dibenzoyltartaric acid In methanol Resolution of racemate; 1.III.b b) Resolution of diamine 3b. Formation of a salt with ditoluoyltartaric acid in methanol and crystallisation from methanol initially gave (S1S) 4b in 74% ee. It should be possible to increase the ee by further crystallisation. Formation of a salt with dibenzoyltartaric acid in methanol and crystallisation from methanol initially gave 4b in98% ee.
  • 4
  • [ 24424-99-5 ]
  • [ 58520-04-0 ]
  • [2-<i>tert</i>-butoxycarbonylamino-1,2-bis-(4-methoxy-phenyl)-ethyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% In triethylamine at 20℃; for 2h;
  • 5
  • [ 58520-04-0 ]
  • (1S,2S)-(-)-1,2-bis(4-hydroxyphenyl)ethane-1,2-diammonium dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With boron tribromide In dichloromethane for 48h;
With boron tribromide In dichloromethane at -78 - 20℃;
  • 6
  • [ 58520-04-0 ]
  • 4-[(1S,2S)-1,2-Diamino-2-(4-methoxy-phenyl)-ethyl]-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With boron tribromide In dichloromethane at 20℃; for 48h;
  • 7
  • [ 58520-04-0 ]
  • [ 91548-22-0 ]
YieldReaction ConditionsOperation in experiment
With boron tribromide In dichloromethane for 48h;
Multi-step reaction with 2 steps 1: 100 percent / BBr3 / CH2Cl2 / 48 h 2: 99 percent / polymer supported piperazine / methanol / 2 h
  • 8
  • [ 58520-04-0 ]
  • [ 787590-29-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: BBr3 / CH2Cl2 / -78 - 20 °C 2: 3.43 g / NaHCO3 / tetrahydrofuran; H2O / 20 °C
Multi-step reaction with 2 steps 1: BBr3 / CH2Cl2 / 48 h 2: DIPEA / tetrahydrofuran / 0 - 20 °C
  • 9
  • [ 58520-04-0 ]
  • [ 896155-78-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: BBr3 / CH2Cl2 / -78 - 20 °C 2: 3.43 g / NaHCO3 / tetrahydrofuran; H2O / 20 °C 3: 64 percent / K2CO3; 18-crown-6 / dimethylformamide; tetrahydrofuran / 48 h / Heating
  • 10
  • [ 58520-04-0 ]
  • (1S,2S)-(-)-1,2-bis(4-decyloxyphenyl)ethane-1,2-diammonium bis(trifluoroacetate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: BBr3 / CH2Cl2 / -78 - 20 °C 2: 3.43 g / NaHCO3 / tetrahydrofuran; H2O / 20 °C 3: 64 percent / K2CO3; 18-crown-6 / dimethylformamide; tetrahydrofuran / 48 h / Heating 4: 100 percent / CH2Cl2 / 1 h / 20 °C
  • 11
  • [ 58520-04-0 ]
  • (1S,2S)-1,2-Bis-(4-benzyloxy-phenyl)-ethane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: BBr3 / CH2Cl2 / 48 h 2: DIPEA / tetrahydrofuran / 0 - 20 °C 3: 87 percent / K2CO3; 18-crown-6 / acetone / Heating 4: 96 percent / TFA / CH2Cl2 / 20 °C
  • 12
  • [ 58520-04-0 ]
  • [ 787590-31-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: BBr3 / CH2Cl2 / 48 h 2: DIPEA / tetrahydrofuran / 0 - 20 °C 3: 87 percent / K2CO3; 18-crown-6 / acetone / Heating
  • 13
  • [ 58520-04-0 ]
  • (1S,2S)-1,2-Bis-[4-(3,5-bis-benzyloxy-benzyloxy)-phenyl]-ethane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: BBr3 / CH2Cl2 / 48 h 2: DIPEA / tetrahydrofuran / 0 - 20 °C 3: 78 percent / K2CO3; 18-crown-6 / acetone / Heating 4: 86 percent / TFA / CH2Cl2 / 20 °C
  • 14
  • [ 58520-04-0 ]
  • [ 863117-83-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: BBr3 / CH2Cl2 / 48 h 2: DIPEA / tetrahydrofuran / 0 - 20 °C 3: 78 percent / K2CO3; 18-crown-6 / acetone / Heating
  • 15
  • [ 58520-04-0 ]
  • [ 855309-78-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: BBr3 / CH2Cl2 / 48 h / 20 °C 2: 1.1 g / triethylamine / acetonitrile / 0.5 h / 20 °C
  • 16
  • [ 58520-04-0 ]
  • (1S,2S)-1-[4-(4-{4-[(1S,2S)-1,2-Diamino-2-(4-methoxy-phenyl)-ethyl]-phenoxymethyl}-benzyloxy)-phenyl]-2-(4-methoxy-phenyl)-ethane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: BBr3 / CH2Cl2 / 48 h / 20 °C 2: 1.1 g / triethylamine / acetonitrile / 0.5 h / 20 °C 3: 89 percent / K2CO3 / dimethylformamide / 50 °C 4: 96 percent / trifluoroacetic acid / CH2Cl2 / 20 °C
  • 17
  • [ 58520-04-0 ]
  • [ 855309-79-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: BBr3 / CH2Cl2 / 48 h / 20 °C 2: 1.1 g / triethylamine / acetonitrile / 0.5 h / 20 °C 3: 89 percent / K2CO3 / dimethylformamide / 50 °C
  • 18
  • [ 98-59-9 ]
  • [ 58520-04-0 ]
  • [ 887924-07-4 ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine In dichloromethane at 0 - 20℃; for 1.5 - 26h; 1.IV.b b) Tosyl-5b (Z = OCH3, B = 4-CH3-C6H4). Triethylamine (190 μl, 1.3 mmol) was added to a solution of the diamine 4b (175 mg, 0.65 mmol) in anhydrous dichloromethane (8 ml) and the solution was cooled to 00C. A solution of the tosyl chloride (p-toluenesulphonyl chloride, 1428 mg, 0.67 mmol) in anhydrous dichloromethane (5 ml) was added slowly. The mixture was stirred at 00C for 30-120 minutes and allowed to warm to room temperature over 1-24 hours. Water was added and the layers separated. The aqueous layer was extracted twice with dichloromethane and the combined organic layers were washed with brine, dried (Na2SO4) and evaporated. The crude mono-sulfonylated diamine could be purified by column chromatography. Purification by column chromatography gave 270 mg (91%) of Ts-5b as a white solid.
  • 19
  • d,l-1,2-diamino-1,2-bis(4-methoxyphenyl)ethane [ No CAS ]
  • [ 58520-03-9 ]
  • [ 58520-04-0 ]
YieldReaction ConditionsOperation in experiment
With ditoluoyltartaric acid; In methanol;Resolution of racemate;Purification / work up; b) Resolution of diamine 3b. Formation of a salt with ditoluoyltartaric acid in methanol and crystallisation from methanol initially gave (S1S) 4b in 74% ee. It should be possible to increase the ee by further crystallisation. Formation of a salt with dibenzoyltartaric acid in methanol and crystallisation from methanol initially gave 4b in98% ee.
  • 20
  • [ 825-60-5 ]
  • [ 58520-04-0 ]
  • [ 1092654-41-5 ]
YieldReaction ConditionsOperation in experiment
66% In ethanol at 20℃; Reflux; optical yield given as %ee;
  • 21
  • [ 123-11-5 ]
  • [ 58520-04-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 20 °C 2: hydrogenchloride / water; tetrahydrofuran / 3 h / 20 °C
  • 22
  • C30H28N2O4 [ No CAS ]
  • [ 58520-04-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 3h; 3 EXAMPLE 3 EXAMPLE 3Hydrolysis of the diimine products formed by either Procedure A or B.[00107] The diimine products from either procedure A or B were dissolved in THF (30 mL) and aqueous HC1 (3 mL, 12 M) was added. The mixture stuffed at room temperature for 3 hours then was partitioned between H20 (100 mL) and CH2C12 (100 mL). The organic phase was removed and the aqueous phase washed with CH2C12 (100 mL). The aqueous phase was made basic by slow addition of 3 M NaOH. The resulting cloudy solution was extracted with CH2C12 (3 x 150 mL). The organic phases were dried over Na2SO4, filtered, and concentrated by rotovap. The resulting diamines are further dried by oil pump vacuum.
Stage #1: C30H28N2O4 With hydrogenchloride In tetrahydrofuran; water Stage #2: With sodium hydroxide In dichloromethane
  • 23
  • [ 3163-76-6 ]
  • [ 58520-04-0 ]
  • [ 1619263-28-3 ]
  • 24
  • [ 585-47-7 ]
  • [ 58520-04-0 ]
  • [ 1599484-91-9 ]
YieldReaction ConditionsOperation in experiment
62% With triethylamine In dichloromethane at 0 - 20℃; for 14h;
With triethylamine In dichloromethane
  • 25
  • C78H70N4O6 [ No CAS ]
  • [ 10534-59-5 ]
  • [ 58520-04-0 ]
  • C94H86N6O6*C2H3O2(1-)*C16H36N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 20℃;
  • 26
  • [ 7647-01-0 ]
  • [ 6147-53-1 ]
  • [ 58520-04-0 ]
  • C48H60CoN6O6(3+)*3Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: cobalt(II) diacetate tetrahydrate; (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine With oxygen; pyrographite In methanol at 20℃; for 16h; Stage #2: hydrogenchloride In water
  • 27
  • [ 7647-01-0 ]
  • cobalt(II) perchlorate hexahydrate [ No CAS ]
  • [ 58520-04-0 ]
  • C48H60CoN6O6(3+)*3Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: cobalt(II) perchlorate hexahydrate; (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine With pyrographite In methanol for 16h; Stage #2: hydrogenchloride In methanol
  • 28
  • [ 626-19-7 ]
  • [ 58520-04-0 ]
  • C40H38N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% Stage #1: Isophthalaldehyde; (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine In dichloromethane at 20℃; for 1.5h; Inert atmosphere; Stage #2: With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;
  • 29
  • [ 100-52-7 ]
  • [ 58520-04-0 ]
  • [ 1092654-41-5 ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: benzaldehyde; (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine In dichloromethane at 20℃; for 1.33333h; Inert atmosphere; Stage #2: With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere;
  • 30
  • [ 58520-04-0 ]
  • C18H24N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / para-xylene / 3 h / Reflux 2: water / 12 h / Reflux 3: hydrazine hydrate / ethanol / 6 h / Reflux
  • 31
  • [ 58520-04-0 ]
  • C27H27F6N3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / para-xylene / 3 h / Reflux 2: water / 12 h / Reflux 3: hydrazine hydrate / ethanol / 6 h / Reflux 4: tetrahydrofuran / 24 h / 0 - 20 °C
  • 32
  • [ 85-44-9 ]
  • [ 58520-04-0 ]
  • C24H22N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: phthalic anhydride; (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine With toluene-4-sulfonic acid In para-xylene for 3h; Reflux; Stage #2: With sodium hydrogencarbonate In dichloromethane; water
  • 33
  • [ 85-44-9 ]
  • [ 58520-04-0 ]
  • C26H26N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / para-xylene / 3 h / Reflux 2: water / 12 h / Reflux
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