Home Cart Sign in  
Chemical Structure| 101-32-6 Chemical Structure| 101-32-6

Structure of 2,2'-(Benzylimino)diethanol
CAS No.: 101-32-6

Chemical Structure| 101-32-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

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

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 101-32-6 ]

CAS No. :101-32-6
Formula : C11H17NO2
M.W : 195.26
SMILES Code : OCCN(CCO)CC1=CC=CC=C1
MDL No. :MFCD00020587
InChI Key :MIZIOHLLYXVEHJ-UHFFFAOYSA-N
Pubchem ID :7553

Safety of [ 101-32-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H319
Precautionary Statements:P305+P351+P338

Computational Chemistry of [ 101-32-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.45
Num. rotatable bonds 6
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 55.86
TPSA ?

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

43.7 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.98
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

0.86
Log Po/w (WLOGP)?

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

0.32
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.

0.98
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

1.23
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.07

Water Solubility

Log S (ESOL):?

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

-1.51
Solubility 5.99 mg/ml ; 0.0307 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.36
Solubility 8.5 mg/ml ; 0.0435 mol/l
Class?

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

Very 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

-2.61
Solubility 0.478 mg/ml ; 0.00245 mol/l
Class?

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

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

No
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

No
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

No
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.

-6.88 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

1.0
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)

1.06

Application In Synthesis of [ 101-32-6 ]

* 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 [ 101-32-6 ]

[ 101-32-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 101-32-6 ]
  • [ 24468-88-0 ]
YieldReaction ConditionsOperation in experiment
54.6% With phosphorus tribromide; In toluene; at 0℃; for 6h;Inert atmosphere; Reflux; A mixture of compound O-1 (12.10 g, 115.1 mmol), benzyl bromide (13.70 mL, 115.3 mmol) and potassium carbonate (31.81 g, 230.2 mmol) in acetone (120 mL) was refluxed for 18 hours, cooled to rt and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v) = 20/1) to give compound O-2 as pale yellow liquid (16.39 g, 72.9%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3): delta 7.36-7.23 (m, 5H), 3.70 (s, 2H), 3.62 (t, J = 5.3 Hz, 4H), 2.72 (t, J = 5.3 Hz, 4H), 2.48 (brs, 2H). [0555] To a solution of compound O-2 (14.60 g, 74.77 mmol) in toluene (140 mL) was added phosphorus tribromide (21.1 mL, 224.5 mmol) dropwise at 0 C under N2. At the end of the addition, the mixture was refluxed for 6 hours, cooled to rt, quenched with ice water (400 mL) and filtered. The filtrate was washed with NaOH solution and extracted with DCM (100 mL x 3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc (v/v) = 10/1) to give the title compound 32-1 as colorless oil (13.30 g, 54.6%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3): delta 7.36-7.25 (m, 5H), 3.73 (s, 2H), 3.34 (t, J = 7.3 Hz, 4H), 2.98 (t, J = 7.3 Hz, 4H).
54.6% With phosphorus tribromide; In toluene; at 0℃; for 6h;Inert atmosphere; Reflux; To a solution of compound O-2 (14.60 g, 74.77 mmol) in toluene (140 mL) was added phosphorus tribromide(21.1 mL, 224.5 mmol) dropwise at 0 C under N2. At the end of the addition, the mixture was refluxed for 6 hours, cooledto rt, quenched with ice water (400 mL) and filtered. The filtrate was washed with NaOH solution and extracted withDCM (100 mL x 3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. Theresidue was purified by silica gel column chromatography (hexane/EtOAc (v/v) = 10/1) to give the title compound 32-1as colorless oil (13.30 g, 54.6%). The compound was characterized by the following spectroscopic data:1H NMR (400 MHz, CDCl3): delta 7.36-7.25 (m, 5H), 3.73 (s, 2H), 3.34 (t, J = 7.3 Hz, 4H), 2.98 (t, J = 7.3 Hz, 4H).
18% With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 8h; Into a 500-mL round-bottom flask was placed 2,2'-(benzylazanediyl)diethanol (11.3 g, 57.9 mmol, 1 equiv) and CH2C12 (100 mL). This was followed by the dropwise addition of phosphorus tribromide (34.6 g, 128 mmol, 2.2 equiv) at 0 C. The resulting solution was stirred for 8 h at room temperature. The reaction was then quenched by the addition of 80 mL of ice-water. The pH value of the solution was adjusted to 7 with sat. aq. Na2C03 solution. The resulting solution was extracted with 3x80 mL of CH2C12. The combined organic layers were dried over anhydrous Na2S04, filtered, and concentrated under vacuum. The residue was purified by normal phase chromatography on silica gel using CH2Cl2/petroleum ether (1 :3). The collected fractions were concentrated under vacuum to afford 3.3 g (18% yield) of the title compound as yellow oil. 1H MR (400 MHz, CDC13) delta (ppm): 7.34-7.27 (m, 5H), 3.73 (s, 2H), 3.43 (t, J= 7.2 Hz, 4H), 2.98 (t, J= 7.2 Hz, 1H).
41.58 g With phosphorus tribromide; In toluene; at 0 - 105℃; for 16h; To a 0 C solution of 2,2?-(benzylazanediyl)bis(ethan-l-ol) (30.66 g, 0.16 mol) intoluene (300 mL) was added tribromophosphane (69.13 g, 0.26 mol) dropwise. The resultingmixture was stirred at 105 C for 16 h. After cooling to RT, the volatiles were removed under reduce pressure. The residue was diluted with water (300 mL), and the pH value was adjusted to 9with NaOH. The resulting mixture was extracted with EA (3 x 150 mL), the organic layers combined, dried over anhydrous Na2504 and filtered. The filtrate was concentrated under reducedpressure to give N-benzyl-2-bromo-N-(2-bromoethyl) ethan-1-amine (41.58 g) which was used in next step without any further purification. MS: m/z 320 (M+H).
41.58 g With phosphorus tribromide; In toluene; at 0 - 105℃; for 15h; N-Benzyldiethanolamine (30.66 g, 0.16 mol) in toluene (300 mL) at 0 CPhosphorus tribromide (69.13 g, 0.26 mol) was added dropwise to the solution. The system was heated to 105 C and stirred for 16 h.After cooling to RT, the volatiles were removed under reduced pressure. The residue was diluted with water (300 mL) and the pH was adjusted to 9 with NaOH.The system was extracted with EA (3×150 mL).The filtrate was concentrated under reduced pressure to give N-benzyl-2-bromo-N-(2-bromoethyl)ethane-l-amine (41.58 g).Used directly in the next step without any further purification.

 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 101-32-6 ]

Aryls

Chemical Structure| 101-98-4

A117419 [101-98-4]

2-(Benzyl(methyl)amino)ethanol

Similarity: 1.00

Chemical Structure| 104-63-2

A208848 [104-63-2]

2-(Benzylamino)ethanol

Similarity: 0.94

Chemical Structure| 54881-13-9

A316596 [54881-13-9]

1-Benzylazetidin-3-ol

Similarity: 0.92

Chemical Structure| 246232-73-5

A138024 [246232-73-5]

2-(Dibenzylamino)propane-1,3-diol

Similarity: 0.89

Chemical Structure| 10316-00-4

A169994 [10316-00-4]

4-Benzylmorpholine

Similarity: 0.87

Alcohols

Chemical Structure| 101-98-4

A117419 [101-98-4]

2-(Benzyl(methyl)amino)ethanol

Similarity: 1.00

Chemical Structure| 104-63-2

A208848 [104-63-2]

2-(Benzylamino)ethanol

Similarity: 0.94

Chemical Structure| 54881-13-9

A316596 [54881-13-9]

1-Benzylazetidin-3-ol

Similarity: 0.92

Chemical Structure| 246232-73-5

A138024 [246232-73-5]

2-(Dibenzylamino)propane-1,3-diol

Similarity: 0.89

Chemical Structure| 6940-80-3

A287757 [6940-80-3]

(S)-2-(Benzylamino)propan-1-ol

Similarity: 0.86

Amines

Chemical Structure| 101-98-4

A117419 [101-98-4]

2-(Benzyl(methyl)amino)ethanol

Similarity: 1.00

Chemical Structure| 104-63-2

A208848 [104-63-2]

2-(Benzylamino)ethanol

Similarity: 0.94

Chemical Structure| 246232-73-5

A138024 [246232-73-5]

2-(Dibenzylamino)propane-1,3-diol

Similarity: 0.89

Chemical Structure| 91271-82-8

A160455 [91271-82-8]

2-Morpholin-4-ylmethylbenzylamine

Similarity: 0.87

Chemical Structure| 91271-84-0

A645522 [91271-84-0]

(4-(Morpholinomethyl)phenyl)methanamine

Similarity: 0.87