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N,N-Dibenzyl-2-aminoethanol

N,N-Dibenzyl-2-aminoethanol

N,N-Dibenzyl-2-aminoethanol

CAS No.: 101-06-4

Category Products

Cat.NO.:A639618 Purity:98%

Product Details of [ 101-06-4 ]

CAS No. :	101-06-4
Formula :	C₁₆H₁₉NO
M.W :	241.33
SMILES Code :	OCCN(CC1=CC=CC=C1)CC1=CC=CC=C1
MDL No. :	MFCD00020574
InChI Key :	WTTWSMJHJFNCQB-UHFFFAOYSA-N
Pubchem ID :	22657

Safety of [ 101-06-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 101-06-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	12
Fraction Csp3	0.25
Num. rotatable bonds	6
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	74.37
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	23.47 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.76
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.57
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.38
Log P_o/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.	2.92
Log P_o/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	3.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.75

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.05
Solubility	0.214 mg/ml ; 0.000886 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.	-2.71
Solubility	0.47 mg/ml ; 0.00195 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	-5.3
Solubility	0.00121 mg/ml ; 0.000005 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	No
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.	-5.95 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	0.0
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)	1.27

Application In Synthesis of [ 101-06-4 ]

* 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 [ 101-06-4 ]

[ 101-06-4 ] Synthesis Path-Downstream 1~35

1
[ 75-21-8 ]
[ 103-49-1 ]
[ 101-06-4 ]

Yield	Reaction Conditions	Operation 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.

References: [1]Bulletin de la Societe Chimique de France,1934,vol. <5>1,p. 1006,1008.
[2]Patent: EP289262,1989,A3 .
[3]Patent: EP2653463,2013,A1 .Location in patent: Paragraph 0018.

2
[ 59-67-6 ]
[ 101-06-4 ]
[ 109867-24-5 ]

References: [1]Patent: US2766252,1955, .

3
[ 74-96-4 ]
[ 101-06-4 ]
2-dibenzylamino-ethanol; hydrobromide [ No CAS ]

References: [1]Acta Physiologica Scandinavica,1949,vol. 19,p. 1.

4
[ 874512-36-4 ]
[ 101-06-4 ]
cyclopent-2-enyl-[2]thienyl-acetic acid-(2-dibenzylamino-ethyl ester) [ No CAS ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 2855,2857.

5
[ 2199-94-2 ]
[ 101-06-4 ]
6-bromo-2-oxo-2<i>H</i>-chromene-3-carboxylic acid-(2-dibenzylamino-ethyl ester) [ No CAS ]

References: [1]Patent: US2683720,1949, .

6
[ 1729-01-7 ]
[ 101-06-4 ]
8-methoxy-2-oxo-2<i>H</i>-chromene-3-carboxylic acid-(2-dibenzylamino-ethyl ester) [ No CAS ]

References: [1]Patent: US2683720,1949, .

7
[ 3855-87-6 ]
[ 101-06-4 ]
6,8-dibromo-2-oxo-2<i>H</i>-chromene-3-carboxylic acid-(2-dibenzylamino-ethyl ester) [ No CAS ]

References: [1]Patent: US2683720,1949, .

8
[ 4124-41-8 ]
[ 101-06-4 ]
[ 103276-85-3 ]

References: [1]Patent: US2775608,1950, .

9
[ 101-06-4 ]
[ 51-50-3 ]

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 1103 – 1109.
[2]Journal of the Chemical Society,1949,p. 500,505.
[3]Canadian Journal of Chemistry,1965,vol. 43,p. 3119 – 3128.
[4]European Journal of Organic Chemistry,2014,vol. 2014,p. 1103 – 1109.
[5]Patent: DE538456,1930, .

Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 18,p. 2980.

10
[ 101-06-4 ]
[ 2133-09-7 ]

References: [1]Chemicke Listy,1952,vol. 46,p. 672.

Chem.Abstr.,1953,p. 8028.
[2]Helvetica Chimica Acta,1965,vol. 48,p. 830 – 837.

11
[ 101-06-4 ]
[ 537-11-1 ]

Yield	Reaction Conditions	Operation in experiment
	With dibromo sulfoxide; In cyclohexane; N,N-dimethyl-formamide; for 15h;	To <strong>[101-06-4]N,N-dibenzyl-2-aminoethanol</strong> (80.68 g) were added cyclohexane (500 ml) and DMF (12.9 ml), and thereto was added dropwise thionyl bromide (83.4 g). The mixture was stirred for 15 hours, and to the reaction solution was added an saturated aqueous sodium hydrogen carbonate solution in an ice-bath, and the mixture was extracted with ethyl acetate. The organic layer was washed with water (three times) and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (72.1 g). 1H NMR (400 MHz, CDCl3) delta 7.48-7.39 (m, 8H), 7.36-7.33 (m, 2H), 3.74 (s, 4H), 3.43 (m, 2H), 2.97 (m, 2H).

References: [1]Tetrahedron Letters,2000,vol. 41,p. 3011 – 3014.
[2]Tetrahedron Letters,2008,vol. 49,p. 1648 – 1651.
[3]Patent: US2504977,1946, .
[4]Acta Poloniae Pharmaceutica,1955,vol. 12,p. 223,229.

Chem.Abstr.,1956,p. 12042.
[5]Journal of the Chemical Society,1961,p. 1291 – 1297.
[6]Patent: EP2447264,2012,A1 .Location in patent: Page/Page column 178.

12
[ 101-06-4 ]
1-[bis-(3-nitro-benzyl)-amino]-2-nitryloxy-ethane; nitrate [ No CAS ]

References: [1]Bulletin de la Societe Chimique de France,1940,vol. <5>7,p. 621,623.

Bulletin de la Societe Chimique de France,1944,vol. <5>11,p. 470,474.

13
[ 100-44-7 ]
[ 141-43-5 ]
[ 101-06-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate; In ethanol; for 16h;Heating / reflux;	Example 1; Dibenzylaminoethanol:; To a 250 mL round bottom flask equipped with stirbar, reflux condensor, nitrogen inlet, and septum was added potassium carbonate (56.5 g, 0.41 mol), ethanol (80 mL), and ethanolamine (9.9 mL, 0.16 mol). The stirred solution was heated to reflux and benzyl chloride (37.9 mL, 0.33 mol) was added via syringe. The resulting solution was stirred for 16 hours at reflux, allowed to cool, then poured into water (200 mL). The solution was extracted with chloroform (3×300 mL). The combined organic layers were dried with magnesium sulfate, filtered, then evaporated to dryness. Recrystallization from hexanes yielded the product as colorless crystals (32.8 g, 83 %). 1H NMR (300 MHz, CDCl3) delta 7.33 (10 H), 3.60 (4 H), 3.58 (2 H), 2.67 (2H). 13C NMR (75 MHz, CDCl3) delta 138.9, 129.2, 128.6, 127.4, 58.7, 58.4, 55.0.
69%	With potassium carbonate; In ethanol; for 36h;Reflux;	Dibenzylamino Ethanol Benzyl chloride (278.5g, 2.2 mol), ethanol amine (60 mL, 1 mol), potassium carbonate (283.1g, 2.05mol) and ethanol (2 L) were mixed together in a 3L 3- neck flask, fitted with an overhead stirrer, a condenser and a glass plug. The apparatus was heated up to reflux for 36 hr, after which the insoluble solid was filtered through a medium frit. The filtrate was recovered and ethanol was removed by rotoary evaporation. The viscous liquid was redissolved in ether, the solid suspension removed by filtration and extracted twice against water. The ether solution was kept and the aqueous layer was extracted twice with dichloromethane (2 x 400 mL). The fraction were recombined, dried over MgSO4, stirred over carbon black for 15 min and filtered through a celite pad. Dichloromethane was removed and the solid was redissolved into a minimal amount of ether (combined volume of 300 mL with the first ether fraction, 300 m Details Products CAS 53-59-8 Read more Products CAS 54-21-7 Read more Products CAS 53-64-5 Read more Reviews There are no reviews yet. Be the first to review “N,N-Dibenzyl-2-aminoethanol” Cancel reply Your email address will not be published. Required fields are marked * Your rating * Your review * Name * Email * Save my name, email, and website in this browser for the next time I comment. Previous 3-Methyl-4-phenyl-1H-1,2,4-triazol-5(4H)-one Next 6-Methoxy-2-(p-tolyl)benzo[d]thiazole Easy CDMO Easy CDMO is China TOP100 CDMO company. We believe: Easy CDMO, Medicinal Chemical is Big. More than 100 scientists are serving you. Quick Links About Us Products Blog Contacts Support Links Privacy Policy Term And Condition Locations Office address: Chenxun Technology Building, No. 633, Jinzhong Road, Changning District, Shanghai info@easycdmo.com +8602161734564 © Copyright Easy CDMO 2025. All Rights Reserved.