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[ CAS No. 90050-59-2 ] {[proInfo.proName]}

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Chemical Structure| 90050-59-2
Chemical Structure| 90050-59-2
Structure of 90050-59-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 90050-59-2 ]

CAS No. :90050-59-2 MDL No. :MFCD05662390
Formula : C8H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :YILPAIKZHXATHY-UHFFFAOYSA-N
M.W : 199.04 Pubchem ID :10420289
Synonyms :

Calculated chemistry of [ 90050-59-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.5
TPSA : 17.07 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) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 2.57
Log Po/w (MLOGP) : 2.52
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.52

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.204 mg/ml ; 0.00102 mol/l
Class : Soluble
Log S (Ali) : -2.44
Solubility : 0.72 mg/ml ; 0.00362 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.59
Solubility : 0.0512 mg/ml ; 0.000257 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 90050-59-2 ]

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 [ 90050-59-2 ]

* 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.

  • Upstream synthesis route of [ 90050-59-2 ]
  • Downstream synthetic route of [ 90050-59-2 ]

[ 90050-59-2 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 529-20-4 ]
  • [ 90050-59-2 ]
YieldReaction ConditionsOperation in experiment
21% With aluminum (III) chloride; bromine In dichloromethane at 0 - 20℃; for 20.33 h; Intermediate 6: 5-Bromo-2-methylbenzaldehydeTo a solution of 15.1 g (113 mmol) AICI3 in 30 ml_ CH2CI2 at O0C was added dropwise over 20 min 7.50 ml_ (64.8 mmol) of 2-methylbenzaldehyde followed by the dropwise addition of 3.35 ml_ (64.8 mmol) Br2 in 30 ml_ CH2CI2 <n="54"/>over 8 hrs at O0C. The solution was allowed to warm to room temperature over 12 hours then was poured over 50Og ice. This mixture was extracted with 400 ml_ CH2CI2 and the organics washed with 250 ml_ 1.0 N HCI (aq), 250 ml_ sat. NaHCO3 (aq) and 250 ml_ brine then dried over Na2SO4. The solution was concentrated then the resulting solid was recrystallized twice from 50 ml_ hexanes to give 2.92 g (21 percent) of 5-bromo-2-methylbenzaldehyde as an off-white solid: 1 H NMR (400 MHz, CDCI3). δ 10.21 (s, 1 H), 7.94 (s, 1 H), 7.57 (d, 1 H, J = 8.5 Hz), 7.16 (d, 1 H, J = 8.5 Hz), 2.64 (s, 3H.)
5% With aluminum (III) chloride; bromine In dichloromethane at 0 - 20℃; for 18.5 h; Example 15E
5-Bromo-2-methylbenzaldehyde
77.7 g (583 mmol) of aluminium trichloride are suspended in 200 ml of dichloromethane and cooled to 0° C. 40.0 g (333 mmol) of 2-methylbenzaldehyde are added dropwise over the course of 30 min.
Then 53.2 g (333 mmol) of bromine are added at 0° C. over the course of 6 h, and the mixture is allowed to warm to RT and is stirred for 12 h.
The reaction solution is added to 500 ml of ice-water.
The aqueous phase is extracted several times with dichloromethane.
The combined organic phases are washed successively with 2N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution.
The organic phase is dried over sodium sulfate and concentrated in vacuo.
Purification is by silica gel chromatography and subsequently by crystallization from cyclohexane.
The precipitated product is filtered off.
Yield: 3.2 g (5percent of theory) LC-MS (method 9): Rt=3.26 min MS (EI): m/z=199 (M+H)+
Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 29, p. 6935 - 6949
[2] Patent: WO2008/28118, 2008, A1, . Location in patent: Page/Page column 52-53
[3] Patent: US2007/99885, 2007, A1, . Location in patent: Page/Page column 23
[4] Patent: WO2008/57497, 2008, A2, . Location in patent: Page/Page column 356
[5] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 356
[6] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 356
[7] Patent: EP2746301, 2014, A1, . Location in patent: Page/Page column
  • 2
  • [ 529-20-4 ]
  • [ 90050-59-2 ]
  • [ 83647-40-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 6, p. 1645 - 1652
[2] Patent: WO2005/51911, 2005, A1, . Location in patent: Page/Page column 70
[3] Patent: WO2013/7650, 2013, A1, . Location in patent: Page/Page column 68;69
  • 3
  • [ 258886-04-3 ]
  • [ 90050-59-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 14, p. 2744 - 2748
  • 4
  • [ 156001-51-3 ]
  • [ 90050-59-2 ]
Reference: [1] Patent: US2003/119670, 2003, A1,
  • 5
  • [ 79669-49-1 ]
  • [ 90050-59-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 14, p. 2744 - 2748
  • 6
  • [ 90050-59-2 ]
  • [ 90326-54-8 ]
Reference: [1] Patent: WO2014/138616, 2014, A2,
  • 7
  • [ 529-20-4 ]
  • [ 90050-59-2 ]
  • [ 83647-40-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 6, p. 1645 - 1652
[2] Patent: WO2005/51911, 2005, A1, . Location in patent: Page/Page column 70
[3] Patent: WO2013/7650, 2013, A1, . Location in patent: Page/Page column 68;69
  • 8
  • [ 90050-59-2 ]
  • [ 1030825-20-7 ]
Reference: [1] Patent: CN104072348, 2018, B,
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