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[ CAS No. 24589-89-7 ] {[proInfo.proName]}

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Chemical Structure| 24589-89-7
Chemical Structure| 24589-89-7
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Product Details of [ 24589-89-7 ]

CAS No. :24589-89-7 MDL No. :MFCD02257408
Formula : C9H7BrO4 Boiling Point : -
Linear Structure Formula :- InChI Key :KXRYNWDCFUKVNN-UHFFFAOYSA-N
M.W : 259.05 Pubchem ID :968879
Synonyms :

Calculated chemistry of [ 24589-89-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.6
TPSA : 63.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 1.71
Log Po/w (WLOGP) : 1.73
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 1.96
Consensus Log Po/w : 1.6

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.58
Solubility : 0.687 mg/ml ; 0.00265 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.565 mg/ml ; 0.00218 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.72
Solubility : 0.492 mg/ml ; 0.0019 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.95

Safety of [ 24589-89-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24589-89-7 ]

* 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 [ 24589-89-7 ]
  • Downstream synthetic route of [ 24589-89-7 ]

[ 24589-89-7 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 24589-89-7 ]
  • [ 108-24-7 ]
  • [ 23145-07-5 ]
YieldReaction ConditionsOperation in experiment
40% at 100℃; for 20 h; Heating / reflux To a mixture of 2-formyl-4-bromophenoxy acetic acid [(50G,] 0. [192MOL),] sodium acetate [(100G,] 1. 21mol) in acetic acid (250mL) at [100°C] was added acetic anhydride [(LOOML)] portions during a period of 3h. The reaction mixture was then refluxed for 20h. The solvent was removed by distillation and residue diluted with 3N HCl [(500ML)] and refluxed for 2h. The reaction mixture was then concentrated under vacuum and product extracted with pet. ether [(3X200ML).] The organic layer was washed with 10percent [NAHC03] solution and evaporated to give [5-BROMO-1-BENZOFURAN] [(15G,] 40percent) as a pale yellow liquid.
Reference: [1] Patent: WO2004/7491, 2004, A1, . Location in patent: Page 51-52
  • 2
  • [ 51336-47-1 ]
  • [ 24589-89-7 ]
YieldReaction ConditionsOperation in experiment
94% With lithium hydroxide; water In tetrahydrofuran at 20℃; for 24 h; A mixture of ethyl-2-formyl-4-bromophenoxy acetate (60g, 0. [209MOL),] [LIOH] (7. 5g, [0.] [31MOL),] THF (250mL) and water (lOOmL) was stirred at RT for 24h. The reaction mixture was concentrated under reduce pressure and residue acidified with 1. 5N HCl to pH=2. The solid precipitate obtained was filtered and dried to give 4-bromo-2- formylphenoxy acetic acid [(50G,] 94percent).
Reference: [1] Patent: WO2004/7491, 2004, A1, . Location in patent: Page 51
[2] Organic Letters, 2015, vol. 17, # 23, p. 5824 - 5827
[3] European Journal of Medicinal Chemistry, 1999, vol. 34, # 12, p. 1061 - 1070
  • 3
  • [ 79-08-3 ]
  • [ 1761-61-1 ]
  • [ 24589-89-7 ]
YieldReaction ConditionsOperation in experiment
55% With sodium hydroxide In tetrahydrofuran; water Step A:
(4-Bromo-2-formyl)phenoxyacetic acid. Monohydrate
To a solution of 5-bromosalicylaldehyde (5.0 kg, 24.87 mol) in tetrahydrofuran (12.1 L) at 40° C. under a nitrogen atmosphere is added a solution of bromoacetic acid (3.8 kg, 27.42 mol) in water (50 L).
The mixture is stirred at 40° C. and a solution of sodium hydroxide (2.09 kg, 52.29 mmol) in water (8.1 L) added over 20 min.
The deep red solution is warmed to gentle reflux for 18 hours.
Tetrahydrofuran (~7 L) is distilled from the reaction mixture at atmospheric pressure and the resultant yellow solution cooled to room temperature (25° C.).
The pH is adjusted to 8+-0.2 by addition of saturated sodium bicarbonate solution.
The resultant mixture is extracted with isopropylacetate (2*15 L) and the aqueous layer acidified to pH 3+-0.2 with concentrated hydrochloric acid (2.4 L).
The resultant slurry is aged at 20° C. for 1 hour, filtered, and the cake washed with water (7 L).
The product is air dried for 3 hours, and in vacuo overnight to give the product as a pale yellow solid (3.77 Kg, 55percent yield).
Reference: [1] Patent: US5149838, 1992, A,
  • 4
  • [ 1761-61-1 ]
  • [ 24589-89-7 ]
Reference: [1] Patent: US5378718, 1995, A,
[2] Journal of Medicinal Chemistry, 1969, vol. 12, # 3, p. 420 - 424
[3] Organic Letters, 2015, vol. 17, # 23, p. 5824 - 5827
  • 5
  • [ 79-11-8 ]
  • [ 1761-61-1 ]
  • [ 24589-89-7 ]
Reference: [1] Journal of the Indian Chemical Society, 2008, vol. 85, # 7, p. 754 - 758
[2] Archiv der Pharmazie, 2015, vol. 348, # 6, p. 421 - 432
  • 6
  • [ 24581-99-5 ]
  • [ 24589-89-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1969, vol. 12, # 3, p. 420 - 424
  • 7
  • [ 6280-80-4 ]
  • [ 24589-89-7 ]
Reference: [1] Chemische Berichte, 1884, vol. 17, p. 2997
[2] Tetrahedron, 1969, vol. 25, p. 2407 - 2415
  • 8
  • [ 90-02-8 ]
  • [ 24589-89-7 ]
Reference: [1] Chemische Berichte, 1884, vol. 17, p. 2997
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