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[ CAS No. 103273-01-4 ] {[proInfo.proName]}

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Chemical Structure| 103273-01-4
Chemical Structure| 103273-01-4
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Product Details of [ 103273-01-4 ]

CAS No. :103273-01-4 MDL No. :MFCD00052693
Formula : C10H14BrN Boiling Point : -
Linear Structure Formula :- InChI Key :OLKYFBNIFKQRIZ-UHFFFAOYSA-N
M.W :228.13 Pubchem ID :238591
Synonyms :

Calculated chemistry of [ 103273-01-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.82
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.48
Log Po/w (XLOGP3) : 3.6
Log Po/w (WLOGP) : 3.34
Log Po/w (MLOGP) : 3.46
Log Po/w (SILICOS-IT) : 2.93
Consensus Log Po/w : 3.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.83
Solubility : 0.034 mg/ml ; 0.000149 mol/l
Class : Soluble
Log S (Ali) : -3.83
Solubility : 0.0335 mg/ml ; 0.000147 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.11
Solubility : 0.0178 mg/ml ; 0.000078 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.45

Safety of [ 103273-01-4 ]

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

Application In Synthesis of [ 103273-01-4 ]

* 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.

  • Upstream synthesis route of [ 103273-01-4 ]
  • Downstream synthetic route of [ 103273-01-4 ]

[ 103273-01-4 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 103273-01-4 ]
  • [ 6683-75-6 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1966, vol. 85, p. 457 - 466
  • 2
  • [ 103273-01-4 ]
  • [ 3972-64-3 ]
Reference: [1] Heterocycles, 2006, vol. 68, # 12, p. 2635 - 2645
[2] Chemische Berichte, 1888, vol. 21, p. 2956
[3] Journal of the American Chemical Society, 1944, vol. 66, p. 914,917
[4] Journal of the American Chemical Society, 1946, vol. 68, p. 1088
[5] Chemische Berichte, 1962, vol. 95, p. 1921 - 1942
[6] Organic and Biomolecular Chemistry, 2007, vol. 5, # 23, p. 3778 - 3786
  • 3
  • [ 769-92-6 ]
  • [ 103273-01-4 ]
YieldReaction ConditionsOperation in experiment
87% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 18.5 h; Darkness To a solution of 4-tert-butylaniline (10 g, 68 mmol) in DMF (150 mL) cooled to 0 °C was added NBS (12.1 g, 68 mmol) under strictly exclusion of light, and the mixture was stirred for 30 min at the same temperature. Then the ice-bath was removed and the stirring was continued at rt overnight (18 h). The mixture was poured into water (300 mL) and extracted with CH2Cl2, the combined organic phase was over MgSO4 and filtered. he filtrate was evaporated to give a black-brown tar which was purified by column chromatography (PE : EtOAc = 20 : 1) to obtain a colorless oil (13.5 g, 87 percent); Rf = 0.69 (PE : EtOAc = 5 : 1); 1H-NMR (CDCl3, 300 MHz) δ: 7.43 (t, J = 1.2 Hz, 1H), 7.14 (m, 1H), 6.72 (d, J = 8.1 Hz,1H), 3.96 (br, 2H), 1.30 (s, 9H).
68% With N-Bromosuccinimide In chloroform at 0 - 20℃; for 5 h; Inert atmosphere Prepared according to a literature procedure. To a solution of 4-(tertbutyl)aniline (5.50 mL, 34.5 mmol, 1.0 eq.) in chloroform (200 mL) at 0 °C wasadded N-bromosuccinimide (6.76 g, 37.9 mmol, 1.1 eq.). The reaction was warmed to room temperature and stirred for 5 hours, then washed with water and extracted into chloroform. The organic phase was dried over sodium sulphate and the solvent removed under reduced pressure. Purification by flash chromatography on silica gel (SiO2, hexane)afforded the title compound as a brown oil (5.35 g, 23.5 mmol, 68 percent yield).
Reference: [1] Heterocycles, 2006, vol. 68, # 12, p. 2635 - 2645
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 1, p. 178 - 183[3] Angew. Chem., 2014, vol. 126, # 1, p. 182 - 187,6
[4] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5248 - 5252
[5] Journal of Fluorine Chemistry, 2015, vol. 180, p. 33 - 39
[6] Journal of the American Chemical Society, 2005, vol. 127, # 25, p. 9071 - 9078
[7] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7360 - 7377
[8] Tetrahedron, 2001, vol. 57, # 38, p. 8075 - 8083
[9] Patent: WO2008/147952, 2008, A1, . Location in patent: Page/Page column 53
[10] Patent: WO2009/36412, 2009, A1, . Location in patent: Page/Page column 66
[11] Patent: WO2010/53471, 2010, A1, . Location in patent: Page/Page column 49
[12] Patent: US2011/98311, 2011, A1,
[13] Patent: US2011/98311, 2011, A1,
[14] Patent: US2012/309758, 2012, A1, . Location in patent: Page/Page column 76
[15] Angewandte Chemie - International Edition, 2014, vol. 53, # 19, p. 4945 - 4949
[16] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 0459; 1959
[17] Journal of the American Chemical Society, 2016, vol. 138, # 40, p. 13147 - 13150
[18] Chinese Journal of Chemistry, 2018, vol. 36, # 9, p. 815 - 818
  • 4
  • [ 91801-97-7 ]
  • [ 103273-01-4 ]
Reference: [1] Chemische Berichte, 1962, vol. 95, p. 1921 - 1942
[2] Tetrahedron Letters, 1996, vol. 37, # 52, p. 9325 - 9328
[3] Tetrahedron, 2001, vol. 57, # 38, p. 8075 - 8083
[4] Organic and Biomolecular Chemistry, 2007, vol. 5, # 23, p. 3778 - 3786
  • 5
  • [ 20330-45-4 ]
  • [ 103273-01-4 ]
Reference: [1] Tetrahedron, 2001, vol. 57, # 38, p. 8075 - 8083
[2] Tetrahedron Letters, 1996, vol. 37, # 52, p. 9325 - 9328
[3] Chemische Berichte, 1962, vol. 95, p. 1921 - 1942
  • 6
  • [ 769-92-6 ]
  • [ 103273-01-4 ]
  • [ 10546-67-5 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
  • 7
  • [ 769-92-6 ]
  • [ 103273-01-4 ]
  • [ 10546-67-5 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
  • 8
  • [ 103273-01-4 ]
  • [ 10546-67-5 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 1602,1603
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