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Chemical Structure| 103-49-1 Chemical Structure| 103-49-1

Structure of Dibenzylamine
CAS No.: 103-49-1

Chemical Structure| 103-49-1

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Synonyms: Bisbenzylamine

4.5 *For Research Use Only !

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Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

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Product Details of [ 103-49-1 ]

CAS No. :103-49-1
Formula : C14H15N
M.W : 197.28
SMILES Code : C1(CNCC2=CC=CC=C2)=CC=CC=C1
Synonyms :
Bisbenzylamine
MDL No. :MFCD00004770
InChI Key :BWLUMTFWVZZZND-UHFFFAOYSA-N
Pubchem ID :7656

Safety of [ 103-49-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314-H411
Precautionary Statements:P264-P270-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P391-P405-P501
Class:8
UN#:2735
Packing Group:

Computational Chemistry of [ 103-49-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 12
Fraction Csp3 0.14
Num. rotatable bonds 4
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 63.5
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

12.03 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.74
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.67
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.67
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

3.34
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.45
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.98

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.07
Solubility 0.167 mg/ml ; 0.000845 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.57
Solubility 0.526 mg/ml ; 0.00266 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-5.78
Solubility 0.000328 mg/ml ; 0.00000166 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.61 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.0

Application In Synthesis of [ 103-49-1 ]

* 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 [ 103-49-1 ]

[ 103-49-1 ] Synthesis Path-Downstream   1~38

  • 1
  • [ 75-21-8 ]
  • [ 103-49-1 ]
  • [ 101-06-4 ]
YieldReaction ConditionsOperation in experiment
In methanol; A. Condensed ethylene oxide (7 ml, 125 mmol) was added to a mixture of dibenzylamine (19.2 ml, 100 mmol) in methanol (20 ml) cooled to 0C. After 2 hours at room temperature, the mixture was evaporated without heating above room temperature. The residue was distilled to afford the title compound, bp. 220-225C/25 mm, which solidified on standing, mp 48C.
at 130℃; under 3102.97 Torr; for 18h;Inert atmosphere; Autoclave; Large scale; Dibenzylamine (7627 g) was charged to a 24-L N2-purged pressure vessel. The reactor was pressurized and vented several times with N2, then pressurized with N2 and heated to 130 C. Ethylene oxide (1880 g) was fed into the reactor at such a rate to keep the pressure below 60 psia (?4 h). Upon completing the ethylene oxide addition, the reaction mixture was stirred at 130 C for 14 h. After lowering the temperature to 60 C and releasing pressure, 45%potassium hydroxide (70 g) was added to the vessel and the reaction mixture stirred at 110 C to remove water. The temperature was increased to 130 C and butylene oxide (11,277 g) was fed into the reactor at such a rate to keep the pressure below 60 psia (~31 h). Upon completing the addition, the reaction mixture was stirred for 4 h at 130 C. The reaction mixture was cooled to room temperature and the reaction mixture neutralized with acetic acid.
  • 2
  • [ 5350-41-4 ]
  • [ 100-46-9 ]
  • [ 103-49-1 ]
  • 3
  • [ 5350-41-4 ]
  • [ 100-46-9 ]
  • [ 103-49-1 ]
  • [ 75-50-3 ]
  • 4
  • [ 3034-48-8 ]
  • [ 103-49-1 ]
  • [ 21166-16-5 ]
  • 5
  • [ 3034-48-8 ]
  • [ 103-49-1 ]
  • [ 21166-15-4 ]
  • 6
  • [ 103-49-1 ]
  • [ 627-18-9 ]
  • [ 3161-51-1 ]
  • 7
  • [ 503-30-0 ]
  • [ 103-49-1 ]
  • [ 3161-51-1 ]
  • 8
  • [ 79-37-8 ]
  • [ 5585-96-6 ]
  • [ 103-49-1 ]
  • [ 77872-23-2 ]
  • 9
  • [ 540-51-2 ]
  • [ 103-49-1 ]
  • [ 101-06-4 ]
  • 10
  • [ 143766-89-6 ]
  • [ 103-49-1 ]
  • [ 143766-90-9 ]
  • 11
  • [ 67442-07-3 ]
  • [ 103-49-1 ]
  • [ 191731-35-8 ]
  • 12
  • [ 79-37-8 ]
  • [ 23876-39-3 ]
  • [ 103-49-1 ]
  • [ 96005-26-4 ]
  • 13
  • [ 28987-75-9 ]
  • ammonium hydroxide [ No CAS ]
  • [ 2905-56-8 ]
  • [ 100-46-9 ]
  • [ 103-49-1 ]
  • 14
  • [ 21286-54-4 ]
  • [ 103-49-1 ]
  • [ 251929-30-3 ]
  • 16
  • [ 96-49-1 ]
  • [ 103-49-1 ]
  • [ 101-06-4 ]
YieldReaction ConditionsOperation in experiment
83% With tetra-(n-butyl)ammonium iodide; at 20 - 140℃; for 26h; Preparation Example: Preparation Acetic acid 2-dibenzylamino-ethyl ester; Stepi : 0.5 gram of dibenzylamine (2.5 mmol), 0.446 gram of ethylenecarbonate (5 mmol) and 0.215 gram of tetraethylammoniumiodide (083 mmol) were mixed together at room temperature. The solid mixture was then heated at 1409C and the resulting suspension was stirred at this temperature for 26 hours. The reaction mixture was diluted with ethyl acetate and extracted with 1 OmL of a 0.5M solution of sodium hydroxide. The aqueous phase was washed with ethyl acetate and the combined organic phases were washed twice with brine. The organic phase was dried on magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash chromatography on silica gel (eluant: ethylacetate/hexane 1/2) to afford 0.5 gram of N, N- dibenzyl-2-aminoethanol (yield: 83%) as an oil.
  • 17
  • [ 54221-96-4 ]
  • [ 4363-35-3 ]
  • [ 103-49-1 ]
  • C29H28N2O [ No CAS ]
  • 18
  • [ 110-89-4 ]
  • [ 100-46-9 ]
  • [ 780-25-6 ]
  • [ 2905-56-8 ]
  • [ 103-49-1 ]
  • 19
  • [ 60-12-8 ]
  • [ 103-49-1 ]
  • [ 102-20-5 ]
  • [ 102459-18-7 ]
  • 20
  • [ 2875-79-8 ]
  • [ 103-49-1 ]
  • [ 1392831-40-1 ]
  • 21
  • [ 103-49-1 ]
  • [ 302348-51-2 ]
  • N,N-dibenzyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine [ No CAS ]
  • 22
  • [ 443776-76-9 ]
  • [ 103-49-1 ]
  • [ 1454653-71-4 ]
  • 23
  • [ 1798-83-0 ]
  • [ 103-49-1 ]
  • C23H24ClNO [ No CAS ]
  • 24
  • [ 1798-83-0 ]
  • [ 103-49-1 ]
  • C23H22ClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% In 1,4-dioxane; triethylamine;Reflux; General procedure: A mixture of amine 8 (500 mg) and the corresponding 3-(N,N-dimethylamino)propiophenone hydrochloride 9 (1 mmol) was dissolved in a mixture of 1,4-dioxane (5 mL) and triethylamine (TEA, 1 mL). The solution was stirred at reflux for 0.5-2 h until the starting materials were not further detected by TLC. After cooling, the solvent was removed under reduced pressure and the crude was purified by column chromatography on silica gel, using a mixture of CH2Cl2:AcOEt (5:1) as eluent.
  • 25
  • [ 2568-25-4 ]
  • [ 103-49-1 ]
  • [ 766-97-2 ]
  • α-[(4-methylphenyl)ethynyl]-N,N-bis(phenylmethyl)benzenemethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With indium(III) chloride; In toluene;Inert atmosphere; Reflux; General procedure: Acetal (1.2 mmol), alkyne (1.2 mmol), dibenzylamine (0.192 mL,1.0 mmol), and InCl3 (10 molpercent) were added to a flask (25 mL), followedby the addition of toluene (2.0 mL) under argon. The mixture was stirredunder reflux and monitored by TLC. The solution was then cooled to r.t.,diluted with dichloromethane (5.0 mL), washed with brine. The aqueouslayer was extracted with CH2Cl2 (3 × 10 mL), the combined organic layer was dried over MgSO4, filtered, and evaporated under vacuum. Theresidue was purified by column chromatography on silica gel (petroleumether) to afford the desired product.
  • 26
  • [ 766-98-3 ]
  • [ 2568-25-4 ]
  • [ 103-49-1 ]
  • N,N-dibenzyl-3-(4-flurophenyl)-1-phenylprop-2-yn-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With indium(III) chloride; In toluene;Inert atmosphere; Reflux; General procedure: Acetal (1.2 mmol), alkyne (1.2 mmol), dibenzylamine (0.192 mL,1.0 mmol), and InCl3 (10 molpercent) were added to a flask (25 mL), followedby the addition of toluene (2.0 mL) under argon. The mixture was stirredunder reflux and monitored by TLC. The solution was then cooled to r.t.,diluted with dichloromethane (5.0 mL), washed with brine. The aqueouslayer was extracted with CH2Cl2 (3 × 10 mL), the combined organic layer was dried over MgSO4, filtered, and evaporated under vacuum. Theresidue was purified by column chromatography on silica gel (petroleumether) to afford the desired product.
  • 27
  • [ 2568-25-4 ]
  • [ 536-74-3 ]
  • [ 103-49-1 ]
  • dibenzyl-(1,3-diphenyl-2-propynyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With indium(III) chloride; In toluene;Inert atmosphere; Reflux; General procedure: Acetal (1.2 mmol), alkyne (1.2 mmol), dibenzylamine (0.192 mL,1.0 mmol), and InCl3 (10 molpercent) were added to a flask (25 mL), followedby the addition of toluene (2.0 mL) under argon. The mixture was stirredunder reflux and monitored by TLC. The solution was then cooled to r.t.,diluted with dichloromethane (5.0 mL), washed with brine. The aqueouslayer was extracted with CH2Cl2 (3 × 10 mL), the combined organic layer was dried over MgSO4, filtered, and evaporated under vacuum. Theresidue was purified by column chromatography on silica gel (petroleumether) to afford the desired product.
  • 28
  • [ 110-89-4 ]
  • [ 100-47-0 ]
  • [ 2905-56-8 ]
  • [ 103-49-1 ]
  • 29
  • [ 110-89-4 ]
  • [ 100-47-0 ]
  • [ 780-25-6 ]
  • [ 2905-56-8 ]
  • [ 103-49-1 ]
  • 30
  • [ 1095-03-0 ]
  • N,N-dibenzyl-O-methylhydroxyamine [ No CAS ]
  • [ 91-73-6 ]
  • [ 103-49-1 ]
  • 31
  • [ 4224-62-8 ]
  • [ 103-49-1 ]
  • N,N-dibenzyl-6-chlorohexanamide [ No CAS ]
  • 32
  • [ 42906-19-4 ]
  • [ 103-49-1 ]
  • C35H34N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.1% With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere; Under an argon stream, the aldehyde compound 12.06g (40.0mmol) represented by the following structural formula (M1) , 8.68g (44.0mmol) dibenzyl amine, 13.39g (60.0mmol) triacetoxy sodium borohydride and 100mL of tetrahydrofuran (THF) was stirred at room temperature for 2 hours. After completion of the reaction, the solution was poured into sodium carbonate 100mL 1-M inclusions, which was stirred for 30 minutes and extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure to distill the solvent, to obtain a yellow oily substance. Silica gel chromatography [eluent: toluene / cyclohexane = 1: 1 (v / v)], white crystals were recrystallized with a mixed solvent of ethyl acetate and methanol. Thereby, the diamine compound No. I-4 of the following structural formula (M2) as a colorless crystal rod is obtained. The yield was 16.05g, the yield was 83.1percent, melting point is 99.0°C to 100.0°C .
  • 33
  • [ 103-49-1 ]
  • [ 428855-17-8 ]
  • 34
  • [ 118-90-1 ]
  • [ 7719-09-7 ]
  • [ 75-09-2 ]
  • [ 103-49-1 ]
  • [ 134-62-3 ]
YieldReaction ConditionsOperation in experiment
General procedure: All chemicals were purchased from Sigma Aldrich or MERCKand were used as received without further purification. Ortho-DBET: N, N-dibenzyl-o-methyl benzamide: To a solution of o-toluicacid (2.08 g, 15.3 mmol) in methylene chloride (28 mL), a catalyticamount of DMF (2 drops) was added with stirring. Freshly distilledthionyl chloride (2.3 mL, 31.0 mmol) was added to the flask, andthe resulting solution was gently refluxed for two hours. The reactionmixture was concentrated under reduced pressure to removeexcess thionyl chloride using a warm water bath (55 C). The crudeacid chloride was redissolved in methylene chloride (28 mL), anddibenzyl amine (5.88 mL, 30.6 mmol) was carefully added to theflask, dropwise, over the course of 2-3 min (Note: exothermic, producesgaseous HCl). The solution was allowed to stir at room temperatureovernight. The organic layer was washed with water (30mL) followed by 5% HCl (30 mL), 10% NaOH (30 mL), finally withbrine (30 mL), and dried with anhydrous Na2SO4. The solutionwas filtered and concentrated under reduced pressure to yield agranular, slightly yellow solid before being dissolved in a minimumamount of hot hexanes. The solution was allowed to cool, and crystalswere collected and dried to yield 1.98 g (41% overall) of thepure N, N-dibenzyl-o-toluamide.
  • 35
  • [ 3171-46-8 ]
  • [ 103-49-1 ]
  • 5,7‐dimethyl‐2‐phenyl‐1H-benzoimidazole [ No CAS ]
  • 36
  • [ 110-89-4 ]
  • [ 100-46-9 ]
  • [ 2905-56-8 ]
  • [ 103-49-1 ]
YieldReaction ConditionsOperation in experiment
79%; 21% With platinum-nickel nanoclusters on activated carbon; hydrogen; at 190℃; under 760.051 Torr;Flow reactor; The reactions were performed in a flow-through reactor at atmospheric pressure and temperature 160-230. The reduced humid catalyst was loaded in the reactor between the glass layers of the nozzle and dried in a hydrogen stream at 120 prior to the reaction. The laboratory-grade reaction was a 12Kh18N10T steel tube (inner diameter 9 mm) put in an electric oven (heating zone height 50 mm). Temperature in the reactor was measured using a thermocouple. Hydrogen feed was adjusted using a GV-7 hydrogen generator. The feeding rate of the starting amines was 0.9 and 3.6 L kgcat-1 h-1 and that of hydrogen was 0.5 L h-1 gcat-1 at atmospheric pressure.
  • 37
  • [ 107-18-6 ]
  • [ 103-49-1 ]
  • [ 3161-51-1 ]
  • 38
  • [ 2106-49-2 ]
  • [ 103-49-1 ]
  • C20H17ClN2O2 [ No CAS ]
 

Historical Records

Technical Information

Categories

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[ 103-49-1 ]

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