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[ CAS No. 135999-16-5 ] {[proInfo.proName]}

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Chemical Structure| 135999-16-5
Chemical Structure| 135999-16-5
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Product Details of [ 135999-16-5 ]

CAS No. :135999-16-5 MDL No. :MFCD09056758
Formula : C7H7BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GCFJMEJVRHBPJI-UHFFFAOYSA-N
M.W : 203.03 Pubchem ID :15073622
Synonyms :

Calculated chemistry of [ 135999-16-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.66
TPSA : 29.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 2.16
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 2.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.88
Solubility : 0.267 mg/ml ; 0.00131 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.666 mg/ml ; 0.00328 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.81
Solubility : 0.316 mg/ml ; 0.00156 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 135999-16-5 ]

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

Application In Synthesis of [ 135999-16-5 ]

* 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 [ 135999-16-5 ]
  • Downstream synthetic route of [ 135999-16-5 ]

[ 135999-16-5 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 578-57-4 ]
  • [ 28165-49-3 ]
  • [ 135999-16-5 ]
Reference: [1] Tetrahedron, 1995, vol. 51, # 15, p. 4291 - 4296
  • 2
  • [ 30778-86-0 ]
  • [ 135999-16-5 ]
YieldReaction ConditionsOperation in experiment
30%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2.75 h;
Stage #2: With ethylene dibromide In tetrahydrofuran; hexane at 0 - 20℃; for 14 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water for 1 h;
33 mL (52.8 mMol) n-butyllithium (1.6 M in hexane)were added dropwise to a solution 10 gm (48.1 mMol) tetrahydropyran-2-yl 3-methoxyphenyl ether in 100 mL tetrahydrofuran over 15 minutes. After stirring for 2.5 hours at room temperature, the reaction mixture was cooled to 0° C. and then 4.6 mL (53.2 mMol) 1,2-dibromoethane were added dropwise. The reaction mixture was then allowed to stir at room temperature for about 14 hours. The reaction mixture was then diluted with 50 mL 1 N hydrochloric acid and was stirred for 1 hour. The aqueous phase was extracted with three 100 mL portions of diethyl ether. The organic phases were combined and extracted well with 5 N sodium hydroxide. These basic aqueous extracts were combined and cooled in an ice/water bath. The pH of this aqueous solution was adjusted to about 1 with 5 N hydrochloric acid and then extracted with three 100 mL portions of diethyl ether. These ether extracts were combined and washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography, eluting with a gradient of hexane containing from 0 to 10percent ethyl acetate. Fractions containing the desired compound were combined and concentrated under reduced pressure to provide 2.91 gm (30percent) of a residue which crystallized upon standing.EA: Calculated for C7H7BrO2: Theory: C, 41.41; H, 3.48. Found: C, 41.81; H, 3.46.
30%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2.75 h;
Stage #2: With ethylene dibromide In tetrahydrofuran; hexane at 0 - 20℃; for 14 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water for 1 h;
33 mL (52.8 mMol) n-butyllithium (1.6 M in hexane) were added dropwise to a solution 10 gm (48.1 mMol) tetrahydropyran-2-yl 3-methoxyphenyl ether in 100 mL tetrahydrofuran over 15 minutes. After stirring for 2.5 hours at room temperature, the reaction mixture was cooled to 0°C and then 4.6 mL (53.2 mMol) 1,2-dibromoethane were added dropwise. The reaction mixture was then allowed to stir at room temperature for about 14 hours. The reaction mixture was then diluted with 50 mL 1 N hydrochloric acid and was stirred for 1 hour. The aqueous phase was extracted with three 100 mL portions of diethyl ether. The organic phases were combined and extracted well with 5 N sodium hydroxide. These basic aqueous extracts were combined and cooled in an ice/water bath. The pH of this aqueous solution was adjusted to about 1 with 5 N hydrochloric acid and then extracted with three 100 mL portions of diethyl ether. These ether extracts were combined and washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography, eluting with a gradient of hexane containing from 0 to 10percent ethyl acetate. Fractions containing the desired compound were combined and concentrated under reduced pressure to provide 2.91 gm (30percent) of a residue which crystallized upon standing. EA: Calculated for C7H7BrO2: Theory: C, 41.41; H, 3.48. Found: C, 41.81; H, 3.46.
Reference: [1] Patent: US7045545, 2006, B1, . Location in patent: Page/Page column 22
[2] Patent: EP1204659, 2003, B1, . Location in patent: Page/Page column 16-17
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 6, p. 1571 - 1579
  • 3
  • [ 146746-58-9 ]
  • [ 135999-16-5 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1401 - 1408
[2] Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7305 - 7308
[3] Tetrahedron, 2015, vol. 71, # 15, p. 2317 - 2326
  • 4
  • [ 16932-45-9 ]
  • [ 135999-16-5 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 1, p. 42 - 45
  • 5
  • [ 150-19-6 ]
  • [ 135999-16-5 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1401 - 1408
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 6, p. 1571 - 1579
[3] Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7305 - 7308
[4] Patent: EP1204659, 2003, B1,
  • 6
  • [ 150-19-6 ]
  • [ 6192-52-5 ]
  • [ 30778-86-0 ]
  • [ 135999-16-5 ]
Reference: [1] Patent: EP1204654, 2003, B1,
[2] Patent: EP1204654, , A1, [2] Patent: , 2002, ,
  • 7
  • [ 6751-75-3 ]
  • [ 77-78-1 ]
  • [ 135999-16-5 ]
Reference: [1] European Journal of Organic Chemistry, 2004, # 14, p. 3119 - 3127
  • 8
  • [ 57234-28-3 ]
  • [ 135999-16-5 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1401 - 1408
[2] Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7305 - 7308
  • 9
  • [ 578-57-4 ]
  • [ 28165-49-3 ]
  • [ 135999-16-5 ]
Reference: [1] Tetrahedron, 1995, vol. 51, # 15, p. 4291 - 4296
  • 10
  • [ 578-57-4 ]
  • [ 135999-16-5 ]
  • [ 90-05-1 ]
Reference: [1] Tetrahedron, 1995, vol. 51, # 15, p. 4291 - 4296
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