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[ CAS No. 847728-89-6 ] (S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate

Cat. No.: A181612
Chemical Structure| 847728-89-6
Chemical Structure| 847728-89-6
Structure of 847728-89-6 * Storage: Sealed in dry,Room Temperature
Purity Size Price USA Stock *0-1 Day Global Stock *5-7 Days Quantity
98% 250mg $6.00 Inquiry Inquiry
98% 1g $11.00 Inquiry Inquiry
98% 5g $16.00 Inquiry Inquiry
98% 10g $31.00 Inquiry Inquiry
98% 25g $55.00 Inquiry Inquiry
98% 100g $219.00 Inquiry Inquiry
98% 500g $767.00 Inquiry Inquiry

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* Storage: Sealed in dry,Room Temperature

* Shipping: Normal

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Product Details of [ 847728-89-6 ]

CAS No. :847728-89-6 MDL No. :MFCD11506011
Formula : C13H18BrNO2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :KECPRZHCNCDSET-VIFPVBQESA-N
M.W : 300.19 Pubchem ID :56973617
Synonyms :

Calculated chemistry of [ 847728-89-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.46
TPSA : 38.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.12
Log Po/w (XLOGP3) : 3.52
Log Po/w (WLOGP) : 3.71
Log Po/w (MLOGP) : 3.32
Log Po/w (SILICOS-IT) : 2.95
Consensus Log Po/w : 3.32

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.85
Solubility : 0.0424 mg/ml ; 0.000141 mol/l
Class : Soluble
Log S (Ali) : -4.01
Solubility : 0.0294 mg/ml ; 0.000098 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.62
Solubility : 0.00712 mg/ml ; 0.0000237 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.41

Safety of [ 847728-89-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 847728-89-6 ]

* 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 [ 847728-89-6 ]

[ 847728-89-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 24424-99-5 ]
  • [ 84499-77-4 ]
  • [ 847728-89-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20.0℃; Description 1 : (S)-tert-butyl (1-(4- romophenyl)ethyl)carbamate (D1)A mixture of (S)-(-)-1 -(4-Bromophenyl)ethylamine hydrochloride (9 g, 38.0 mmol, available from Bepharm Ltd No.B157615), di-tert-butyl dicarbonate (8.72 g, 1 .05 mmol), and triethylamine (16ml, 1 14 mmol) in dichloromethane (120ml) was stirred at room temperature overnight. The mixture was diluted with dichloromethane (200ml) and washed with water (100ml). The organic solution was dried over Na2S04 and solvents were evaporated in vacuo to afford the title compound (D1) (12.7 g) as a white solid.1 H NMR (400MHz ,CHLOROFORM-d) δ (ppm): 7.47- 7.42 (2H, m), 7.18 (2H, d, J= 8.4 Hz), 5.30 (2H, br s), 1 .41 (12H, br s).
12.7 g With triethylamine; In dichloromethane; at 20.0℃; A mixture of (S)-(-)-1-(4-Bromophenyl)ethylamine hydrochloride (9 g, 38.0 mmol, available from Bepharm Ltd B157615), di-tert-butyl dicarbonate (8.72 g, 1.05 mmol), and triethylamine (16 ml, 114 mmol) in dichloromethane (120 ml) was stirred at room temperature overnight. The mixture was diluted with dichloromethane (200 ml) and washed with water (100 ml). The organic solution was dried over Na2SO4 and solvents were evaporated in vacuo to afford the title compound (D1) (12.7 g) as a white solid.
  • 2
  • [ 72287-26-4 ]
  • [ 847728-89-6 ]
  • [ 73183-34-3 ]
  • [ 1171897-03-2 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate; Step 1 A flask was charged with tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]carbamate (1.4 g, 4.66 mmol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.42 g, 5.60 mmol, 1.2 eq), <strong>[72287-26-4](1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride</strong> (170 mg, 0.23 mmol, 0.05 eq), potassium acetate (915 mg, 9.33 mmol, 2 eq) and dioxane (30 mL). The mixture was purged with nitrogen for 10 min, then heated to 80 C. for 1 h. The reaction mixture was cooled to 20 C. and filtered through a pad of celite. The filtrate was concentrated in vacuum. The crude product was purified by column (petroleum ether:ethyl acetate=10:1). Tert-butyl N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate (1.9 g, crude) was obtained as a colorless oil.
With potassium acetate; Step 3 A flask was charged with tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]carbamate (1.4 g, 4.66 mmol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.42 g, 5.60 mmol, 1.2 eq), <strong>[72287-26-4](1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride</strong> (170 mg, 0.23 mmol, 0.05 eq), potassium acetate (915 mg, 9.33 mmol, 2 eq) and dioxane (30 mL). The mixture was purged with nitrogen for 10 minutes, then heated to 80 C. for 1 hour. The reaction mixture was cooled to 20 C. and filtered through a pad of celite. The filtrate was concentrated in vacuum. The crude product was purified by flash chromatography (petroleum ether:ethyl acetate=10:1). Tert-Butyl N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate (1.9 g, crude) was obtained as a colorless oil.
  • 3
  • [ 847728-89-6 ]
  • [ 1047644-76-7 ]
  • benzyl N-[(1S)-1-(4-bromophenyl)ethyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; Step 2 Into a 250-mL round-bottom flask, was placed tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]carbamate (1.0 g, 3.331 mmol, 1 equiv), <strong>[1047644-76-7]1,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (1.48 g, 6.664 mmol, 2.00 equiv), K2CO3 (1.38 g, 9.963 mmol, 2.99 equiv) and Pd(dppf)Cl2 (244.0 mg, 0.333 mmol, 0.10 equiv) in dioxane (16 mL) and H2O (2 mL). The resulting mixture was stirred for 3 hours at 90 C. under nitrogen atmosphere. The mixture was concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:1). This resulted in 1.63 g (99%) of benzyl N-[(1S)-1-(4-bromophenyl)ethyl]carbamate as a light yellow solid.
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