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Chemical Structure| 20921-00-0
Chemical Structure| 20921-00-0
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Product Details of [ 20921-00-0 ]

CAS No. :20921-00-0 MDL No. :MFCD13659375
Formula : C9H7BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :FFZQWUVOIMYRKC-UHFFFAOYSA-N
M.W : 227.05 Pubchem ID :266737
Synonyms :

Calculated chemistry of [ 20921-00-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.49
TPSA : 26.3 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) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 2.33
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 2.58
Log Po/w (SILICOS-IT) : 3.08
Consensus Log Po/w : 2.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.09
Solubility : 0.186 mg/ml ; 0.000821 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.684 mg/ml ; 0.00301 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.72
Solubility : 0.0437 mg/ml ; 0.000192 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 20921-00-0 ]

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 [ 20921-00-0 ]

* 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 [ 20921-00-0 ]
  • Downstream synthetic route of [ 20921-00-0 ]

[ 20921-00-0 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 20921-00-0 ]
  • [ 3875-78-3 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 7, p. 2360 - 2361
  • 2
  • [ 119-84-6 ]
  • [ 20921-00-0 ]
YieldReaction ConditionsOperation in experiment
74% With bromine In dichloromethane at 15℃; A solution of bromine (155 ml) in dichloromethane (500 ml) was added during 30 min to a solution of 3,4-dihydrocoumarin (450 g, 0.3 mol) in dichloromethane (2000 ml). The mixture was stirred overnight at 15°C, then diluted with dichloromethane (2000 ml), and washed with aqueous sodium bicarbonate (2 x 1000 ml) followed by water (1000 ml). The solution was dried over magnesium sulphate, filtered, and concentrated under reduced pressure. The residue was washed with petroleum ether (2 x 500 ml), and filtrate concentrated. The solid was recrystallised from dichloromethane/petroleum ether to give the bromide (BM1490) as thick white crystals (471 g, 74percent).
46.5% With bromine In dichloromethane at 20℃; for 7 h; Reference Example 13 [Step a] To a solution of compound 1 (5.00 g, 33.7 mmol) in dichloromethane (50.0 mL) was added dropwise a solution of bromine (1.80 mL, 35.4 mmol) in dichloromethane (20.0 mL) at room temperature, and the mixture was stirred for 7 hr. To the reaction solution was added water, and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The precipitated solid was suspended and washed in diisopropyl ether (10.0 mL), collected by filtration and washed with diisopropyl ether and hexane to give compound 2 (3.56 g, 46.5percent). MS(ESI)m/z: 227, 229(M+1)+.
Reference: [1] Journal of Organometallic Chemistry, 1990, vol. 387, # 3, p. 381 - 390
[2] Patent: WO2017/49343, 2017, A1, . Location in patent: Paragraph 0066
[3] Patent: EP3135667, 2017, A1, . Location in patent: Paragraph 0425-0426
[4] Justus Liebigs Annalen der Chemie, 1884, vol. 226, p. 359
[5] Journal of Organic Chemistry, 1997, vol. 62, # 24, p. 8522 - 8528
[6] Monatshefte fuer Chemie, 1913, vol. 34, p. 1660
[7] Monatshefte fuer Chemie, 1913, vol. 34, p. 1660
[8] Patent: WO2006/113432, 2006, A2, . Location in patent: Page/Page column 69-70
  • 3
  • [ 1643-30-7 ]
  • [ 20921-00-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 22, p. 10228 - 10243
[2] Patent: WO2018/32467, 2018, A1, . Location in patent: Page/Page column 47; 48
  • 4
  • [ 92569-86-3 ]
  • [ 19063-55-9 ]
  • [ 20921-00-0 ]
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1759 - 1762
  • 5
  • [ 34598-49-7 ]
  • [ 20921-00-0 ]
Reference: [1] Chemistry - An Asian Journal, 2017, vol. 12, # 24, p. 3119 - 3122
  • 6
  • [ 82547-30-6 ]
  • [ 20921-00-0 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 3523,3527
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 3523,3527
  • 7
  • [ 6342-77-4 ]
  • [ 20921-00-0 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 3523,3527
  • 8
  • [ 7017-52-9 ]
  • [ 20921-00-0 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 3523,3527
  • 9
  • [ 34598-49-7 ]
  • [ 20921-00-0 ]
  • [ 1162262-43-2 ]
Reference: [1] European Journal of Organic Chemistry, 2009, # 15, p. 2526 - 2532
[2] European Journal of Organic Chemistry, 2009, # 15, p. 2526 - 2532
  • 10
  • [ 495-78-3 ]
  • [ 20921-00-0 ]
Reference: [1] Monatshefte fuer Chemie, 1913, vol. 34, p. 1660
[2] Monatshefte fuer Chemie, 1913, vol. 34, p. 1660
[3] Justus Liebigs Annalen der Chemie, 1884, vol. 226, p. 359
[4] Monatshefte fuer Chemie, 1913, vol. 34, p. 1660
  • 11
  • [ 19063-55-9 ]
  • [ 20921-00-0 ]
Reference: [1] Monatshefte fuer Chemie, 1913, vol. 34, p. 1660
  • 12
  • [ 749878-59-9 ]
  • [ 20921-00-0 ]
Reference: [1] Monatshefte fuer Chemie, 1913, vol. 34, p. 1660
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