Home Cart Sign in  
Chemical Structure| 139525-77-2 Chemical Structure| 139525-77-2

Structure of 139525-77-2

Chemical Structure| 139525-77-2

*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 [ 139525-77-2 ]

CAS No. :139525-77-2
Formula : C13H16ClNO
M.W : 237.73
SMILES Code : COC1=CC2=C(CCN)C=CC=C2C=C1.[H]Cl
MDL No. :MFCD13185884
InChI Key :HPYGZUDDGWEYDQ-UHFFFAOYSA-N
Pubchem ID :16050055

Safety of [ 139525-77-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 139525-77-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 10
Fraction Csp3 0.23
Num. rotatable bonds 3
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 69.89
TPSA ?

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

35.25 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

3.26
Log Po/w (WLOGP)?

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

3.15
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.

2.72
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

2.93
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.41

Water Solubility

Log S (ESOL):?

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

-3.63
Solubility 0.0554 mg/ml ; 0.000233 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.

-3.67
Solubility 0.0503 mg/ml ; 0.000212 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

-4.66
Solubility 0.00525 mg/ml ; 0.0000221 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

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

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.

-5.44 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 [ 139525-77-2 ]

* 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 [ 139525-77-2 ]

[ 139525-77-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 138113-08-3 ]
  • [ 139525-77-2 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogen; sodium hydroxide; In methanol; water; at 30℃; under 3000.3 Torr; In a 10L reactor compound of formula II (230 g), methanol (3,7 L), NaOH solution ((123,3) g NaOH is diluted in 460mL water) and Raney Nickel (41 ,193 g) is charged. Reaction mixture is stirred at 30C and 4 bar hb and monitored with HPLC. After reaction is done, it is filtered and solvent is evaporated. To concentrate is added toluene (4,25 L) and water (2,13 L), mixed and separated. To organic phase water is added (2,13 L), pH is adjusted to 2 with 37 % HCI, and phases are separated. To water phase fe/f-butyl methyl ether (2,13 L) is added and pH is adjusted to 10 with 40 % NaOH. Further organic phase is concentrated, ethanol (230 mL) is added, heated to 50C then 4 M HCI in ie/f-butyl methyl ether (355 mL) and ie/f- butyl methyl ether (920 mL). White precipitate started to obtain. Suspension is cooled to room temperature, filtered, washed with ie/f-butyl methyl ether and dried. Product is white solid (256,2, yield 92%).
90% A mixture of 2-(7-methoxynaphthyl) acetonitrile (100g), methanol (800 ml), aq. sodium hydroxide (30.42 g sodium hydroxide in 100 ml water), 20 g of Raney Ni stirred in hydrogen atmosphere (apply H2 gas up to 10 kg) at 25 to 30 C for 2-3 hrs. Filtered the reaction mixture, distilled out solvent completely under vacuum. IPA is added to the residue and heated at 50 to 55 C, IPA HCI added at 50 to 55 C and stirred for one hour. Cooled the reaction mixture at 10-15C, filtered the solid, washed with IPA and dried. There was thus obtained 2-(7-methoxynanphthyl)ethanamine hydrochloride (Yield 90%, HPLC purity 99.5 to 99.9 %)
83% Example 2: Preparation of 2-(7-methoxy-l-naphthyi)ethanamine hydrochloride of Formula (D) Methanol (500 ml) was added to an autoclave with 1 Kg/cm2 pressure of Ammonia gas at 10C to 15C and stirred for 1 hour followed by addition of (7-methoxy-l- naphthyl)acetonitrile of Formula (C) (70 g). Raney Nickel (14 g) was added and 5.0 Kg/cm2 pressure of Hydrogen gas was applied at 15C to 25C. The reaction was heated to 50C to 55C. The reaction mass was filtered and treated with ethyl acetate (500 ml) at 25C to 35C and cooled to 0C to 5C followed by addition of Con. HCI acid and maintained for 1 hour. The reaction mass was filtered and washed with chilled ethyl acetate (2 X 50 ml) afforded 2-(7-methoxy- l-naphthyl)ethanamine hydrochloride of formula (D) Yield - 83%
32% A solution of (7-methoxynaphthalen-l-yl)acetonitrile (30 g) in methanol (150 mL) and aqueous ammonia (15 mL) was treated with hydrogen gas (3 Kg) in the presence of Raney nickel (45 g) at 40C. After completion of the reaction, the reaction mixture was filtered through a Hyflo. The filtrate was concentrated under vacuum (200-220 mbar) at 45C to 50C to obtain a residue. The residue in ethyl acetate (60 mL) was acidified (pH 2) with concentrated hydrochloric acid (10 mL to 15 mL) at 10C to 15C to obtain a solid. The solid was dried under vacuum (5-10 mbar) at 45C to 50C over 10 to 15 hours to get the title product.Yield (w/w): 32%
32% A solution of <strong>[138113-08-3](7-methoxynaphthalen-1-yl)acetonitrile</strong> (30 g) in methanol (150 mL) and aqueous ammonia (15 mL) was treated with hydrogen gas (3 Kg) in the presence of Raney nickel (45 g) at 40 C. After completion of the reaction, the reaction mixture was filtered through a Hyflo. The filtrate was concentrated under vacuum (200-220 mbar) at 45 C. to 50 C. to obtain a residue. The residue in ethyl acetate (60 mL) was acidified (pH 2) with concentrated hydrochloric acid (10 mL to 15 mL) at 10 C. to 15 C. to obtain a solid. The solid was dried under vacuum (5-10 mbar) at 45 C. to 50 C. over 10 to 15 hours to get the title product. Yield (w/w): 32%

 

Historical Records

Technical Information

Categories