Home Cart Sign in  
Chemical Structure| 676133-24-7 Chemical Structure| 676133-24-7

Structure of 676133-24-7

Chemical Structure| 676133-24-7

(S)-7-Bromo-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride

CAS No.: 676133-24-7

4.5 *For Research Use Only !

Cat. No.: A547030 Purity: 95%

Change View

Size Price

US Stock

Global Stock

In Stock
100mg ł§Ê¶ÊÊ Inquiry Inquiry
250mg łďͶÊÊ Inquiry Inquiry
1g łËîÿ¶ÊÊ Inquiry Inquiry

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

  • 100mg

    ł§Ê¶ÊÊ

  • 250mg

    łďͶÊÊ

  • 1g

    łËîÿ¶ÊÊ

In Stock

- +

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 [ 676133-24-7 ]

CAS No. :676133-24-7
Formula : C10H13BrClN
M.W : 262.57
SMILES Code : N[C@H]1CCCC2=C1C=C(Br)C=C2.[H]Cl
MDL No. :MFCD22393203
InChI Key :GOFDJFJHJKVZRC-PPHPATTJSA-N
Pubchem ID :68538495

Safety of [ 676133-24-7 ]

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

Computational Chemistry of [ 676133-24-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 61.25
TPSA ?

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

26.02 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

3.05
Log Po/w (WLOGP)?

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

3.26
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.

3.08
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

2.85
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.45

Water Solubility

Log S (ESOL):?

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

-3.73
Solubility 0.0488 mg/ml ; 0.000186 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.

-3.26
Solubility 0.143 mg/ml ; 0.000546 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

-3.78
Solubility 0.044 mg/ml ; 0.000167 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

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

Yes
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.

-5.74 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<0.0
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)

2.37

Application In Synthesis of [ 676133-24-7 ]

* 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 [ 676133-24-7 ]

[ 676133-24-7 ] Synthesis Path-Downstream   1~5

  • 1
  • C10H10BrN3 [ No CAS ]
  • [ 676133-24-7 ]
YieldReaction ConditionsOperation in experiment
66.3% A solution of (R)-7-BROMOTETRALIN-L-OL (8.13 g, 35.8 mmol) in toluene (75 mL) was cooled in an ice bath and treated with diphenylphosphorylazide (DPPA, 11.8 g, 9.6 mL, 43 mmol). A solution of 1, 8-diazabicyclo [5.4. 0] undec-7-ene (DBU, 6.5 g, 6.4 mL, 43 mmol) in toluene (20 mL) was added over 35 min and the mixture was allowed to stir at 0 C for 2 h and ambient temp for 16 h. The mixture was filtered through a pad of silica gel (eluted 6: 1 hexanes/ethyl acetate) to remove precipitates and the volatiles were removed in vacuo to give an oily residue of the crude S-azide. This material was used directly in the next step without further characterization. The azide was dissolved in dry THF (60 mL) and added dropwise at RT to a slurry of lithium aluminum hydride (1. 63g, 43 mmol) in dry THF (50 mL). The mixture was stirred at RT for 1H and then heated to reflux for 1 h. The reaction was cooled to RT and quenched by successive addition of water (1.63 mL), 15% aq NaOH (1.63 mL) and water (4.9 mL). The resulting mixture was stirred for 1 h and then filtered through a pad of Celite (eluted diethyl ether). The volatiles were removed in vacuo and the residue taken up into ethyl acetate (120 mL) and treated with 4N HC1 in dioxane (10 mL). The resulting precipitate was filtered (wash ethyl acetate), collected and vacuum dried to give (S)-7-bromo-1, 2,3, 4-TETRAHYDRO-1-NAPTHYLAMINE hydrochloride as a white solid (6.23 g, 66. 3%, note 14). [Note 13. Procedure adapted from: Rover, S.; Adam, G. ; Cesura, A. M.; Galley, G.; Jenck, F.; Monsma Jr. , F. J.; Wichmann, J.; Dautzenberg, F. M. J. Med. Chem. 2000,43, 1329- 1338. Authors report a somewhat diminished yield due to partial formation of a dihydronapthalene via elimination of the hydroxyl moiety Note 14. Analytical chiral HPLC indicated a 96: 4 mixture of enantiomers (Daicel Crownpak (-) COLUMN, isocratic elution 10% methanol in water (0. 1% TFA), 0.8 mL/min, RT 39.4 min (minor enantiomer), 57.6 min (major enantiomer)].
66.3% With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 2.0h;Heating / reflux; A solution of (R)-7-BROMOTETRALIN-1-OL (8.13 g, 35.8 mmol) in toluene (75 mL) was cooled in an ice bath and treated with diphenylphosphorylazide (DPPA, 11.8 g, 9.6 mL, 43 mmol). A solution of 1, 8-diazabicyclo [5.4. 0] undec-7-ene (DBU, 6.5 g, 6.4 mL, 43 mmol) in toluene (20 mL) was added over 35 min and the mixture was allowed to stir at 0 C for 2 h and ambient temp for 16 h. The mixture was filtered through a pad of silica gel (eluted 6: 1 hexanes/ethyl acetate) to remove precipitates and the volatiles were removed in vacuo to give an oily residue of the crude S-azide. This material was used directly in the next step without further characterization. The azide was dissolved in dry THF (60 mL) and added dropwise at RT to a slurry of lithium aluminum hydride (1.63g, 43 mmol) in dry THF (50 mL). The mixture was stirred at RT for Ih and then heated to reflux for 1 h. The reaction was cooled to RT and quenched by successive addition of water (1.63 mL), 15% aq NaOH (1.63 mL) and water (4.9 mL). The resulting mixture was stirred for 1 h and then filtered through a pad of Celite (eluted diethyl ether). The volatiles were removed in vacuo and the residue taken up into ethyl acetate (120 mL) and treated with 4N HC1 in dioxane (10 mL). The resulting precipitate was filtered (wash ethyl acetate), collected and vacuum dried to give (S)-7-bromo-1, 2,3, 4-TETRAHYDRO-1-NAPTHYLAMINE hydrochloride as a white solid (6.23 g, 66. 3%, note 14). [Note 13. Procedure adapted from: Rover, S.; Adam, G.; Cesura, A. M.; Galley, G.; Jenck, F.; Monsma Jr. , F. J.; Wichmann, J.; Dautzenberg, F. M. J. Med. Chem. 2000,43, 1329- 1338. Authors report a somewhat diminished yield due to partial formation of a dihydronapthalene via elimination of the hydroxyl moiety Note 14. Analytical chiral HPLC indicated a 96: 4 mixture of enantiomers (Daicel Crownpak (-) column, isocratic elution 10% methanol in water (0. 1% TFA), 0.8 mL/min, RT 39. 4 min (minor enantiomer), 57.6 min (major enantiomer)]. The following compounds are prepared essentially according to the procedures described in the schemes, charts, examples and preparations set forth herein.
  • 3
  • [ 676133-24-7 ]
  • [ 24424-99-5 ]
  • [ 33974-41-3 ]
  • [ 676137-06-7 ]
  • 4
  • [ 676133-24-7 ]
  • [ 24424-99-5 ]
  • tert-butyl (S)-(7-bromo-1,2,3,4-tetrahydronaphthalen-1-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1 g With triethylamine; In dichloromethane; at 0 - 23℃; for 12.0h; To a stirred solution of above amine hydrochloride (0.94 g,3.6 mmol) in CH2Cl2 (30 mL) was consecutively added triethylamine(1.5 mL, 10.89 mmol) and di-tert-butyl-dicarbonate (1.17 g,5.44 mmol) at 0 C. The reaction mixture was stirred at 23 C for12 h. The reaction mixture was then diluted with CH2Cl2 andwashed with water and brine solution, dried over Na2SO4 andconcentrated. The crude product was purified by column chromatographyover silica gel (20% EtOAc/hexanes) to give 16 (1.0 g, 85%over two steps) as an amorphous solid. Rf 0.7 (20% EtOAc/hexanes);[a]D239.32 (c 1.0, CHCl3); 1H NMR (400 MHz, CDCl3)δ 7.54-7.39 (m, 1H), 7.33-7.09 (m, 1H), 6.94 (d, J 8.1 Hz, 1H), 4.78(q, J 10.6, 8.8 Hz, 2H), 2.88-2.50 (m, 2H), 2.02 (td, J 10.9, 9.9,4.9 Hz, 1H), 1.78 (ddp, J 23.3, 11.4, 4.2 Hz, 3H), 1.49 (s, 9H); 13CNMR (100 MHz, CDCl3) δ 155.55, 139.66, 136.43, 131.38, 130.84,130.31, 119.73, 79.77, 48.67, 30.45, 28.89, 28.57, 20.05.
  • 5
  • (R)-N-((S)-7-bromo-1,2,3,4-tetrahydronaphthalen-1-yl)-2-methylpropane-2-sulfinamide [ No CAS ]
  • [ 676133-24-7 ]
YieldReaction ConditionsOperation in experiment
0.94 g With hydrogenchloride; In methanol; water; for 2.5h; A solution of 15 (1.2 g, 3.63 mmol) in MeOH (20 mL) was treatedwith 6 N HCl in isopropanol (5 mL). After 2.5 h, solvent wasremoved in vacuo, and the residue was co-evaporated with ethylacetate. The residue obtained was dried under high vacuum toprovide (S)-7-bromo-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride(0.94 g).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 676133-24-7 ]

Amines

Chemical Structure| 1810069-91-0

A231931 [1810069-91-0]

6-Bromo-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride

Similarity: 1.00

Chemical Structure| 1810069-90-9

A266551 [1810069-90-9]

7-Bromo-5-methyl-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride

Similarity: 1.00

Chemical Structure| 1199782-93-8

A351552 [1199782-93-8]

7-Bromo-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride

Similarity: 1.00

Chemical Structure| 789490-65-9

A803440 [789490-65-9]

(R)-7-Bromo-1,2,3,4-tetrahydro-naphthalen-1-ylamine hydrochloride

Similarity: 1.00

Chemical Structure| 1443238-61-6

A317792 [1443238-61-6]

(R)-5-Bromo-2,3-dihydro-1H-inden-1-amine hydrochloride

Similarity: 0.98