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[ CAS No. 223576-64-5 ] {[proInfo.proName]}

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Chemical Structure| 223576-64-5
Chemical Structure| 223576-64-5
Structure of 223576-64-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 223576-64-5 ]

CAS No. :223576-64-5 MDL No. :MFCD18383028
Formula : C8H6BClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :IODPQZJZPKMFKV-UHFFFAOYSA-N
M.W : 196.40 Pubchem ID :18476279
Synonyms :

Calculated chemistry of [ 223576-64-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.05
TPSA : 53.6 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) : -6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 0.77
Log Po/w (MLOGP) : 0.35
Log Po/w (SILICOS-IT) : 0.4
Consensus Log Po/w : 0.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.69
Solubility : 0.397 mg/ml ; 0.00202 mol/l
Class : Soluble
Log S (Ali) : -2.64
Solubility : 0.452 mg/ml ; 0.0023 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.8
Solubility : 0.313 mg/ml ; 0.00159 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.71

Safety of [ 223576-64-5 ]

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 [ 223576-64-5 ]

* 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 [ 223576-64-5 ]
  • Downstream synthetic route of [ 223576-64-5 ]

[ 223576-64-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 23145-05-3 ]
  • [ 223576-64-5 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; Dimethyl ether at -60 - -10℃; for 1.25 h;
Stage #2: With Triisopropyl borate In hexane; Dimethyl ether at -60℃;
Stage #3: With hydrogenchloride In hexane; Dimethyl ether; water for 1 h;
5-Chlorobenzofuran was prepared by heating 4-chlorophenoxyacetaldehyde dimethylacetal in polyphosphoric acid; yield: 73percent. [0323] To a solution of 8.8 g (57.7 mmol) 5-chlorobenzofuran in 250 ml dry ether were added 7.32 g (63.0 mmol) tetramethylethylenediamine (TMEDA). The solution was kept below -60° C. under argon, while 37.5 ml of a 1.6M solution of butyllithium in hexane was added dropwise. It was warmed to -10° C. during 45 min and stirred at this temperature for another 30 min. The mixture was cooled again below -60° C. followed by dropwise addition of 35.7 g (190 mmol) triisopropyl borate. After warming to room temperature the mixture was quenched with 70 ml 2N hydrochloric acid and stirred for 1 h. The organic layer was washed three times with 30 ml 2N hydrochloric acid, twice with water, and extracted with 2N sodium hydroxide solution, successively. The alkaline aqueous layer was brought to pH5 and extracted with tert.-butylmethylether. All organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the pale yellow crystalline boronic acid which was used for the next step without further purification. [0324] yield: 9.4 g (83percent); MS 196 (M+).
Reference: [1] Patent: US2004/9976, 2004, A1, . Location in patent: Page/Page column 21-22
[2] Patent: EP1266897, 2002, A2, . Location in patent: Page 35
  • 2
  • [ 23145-05-3 ]
  • [ 227802-36-0 ]
  • [ 5419-55-6 ]
  • [ 20485-44-3 ]
  • [ 223576-64-5 ]
YieldReaction ConditionsOperation in experiment
73% With hydrogenchloride; n-butyllithium In PPA; hexane Step A:
5-Chlorobenzofuran-2-boronic acid
5-Chlorobenzofuran was prepared by heating 4-chlorophenoxyacetaldehyde dimethylacetal in polyphosphoric acid; yield: 73percent.
To a solution of 8.8 g (57.7 mmol) 5-chlorobenzofuran in 250 ml dry ether were added 7.32 g (63.0 mmol) tetramethylethylenediamine (TMEDA).
The solution was kept below -60° C. under argon, while 37.5 ml of a 1.6M solution of butyllithium in hexane was added dropwise.
It was warmed to -10° C. during 45 min and stirred at this temperature for another 30 min.
The mixture was cooled again below -60° C. followed by dropwise addition of 35.7 g (190 mmol) triisopropyl borate.
After warming to room temperature the mixture was quenched with 70 ml 2N hydrochloric acid and stirred for 1 h.
The organic layer was washed three times with 30 ml 2N hydrochloric acid, twice with water, and extracted with 2N sodium hydroxide solution, successively.
The alkaline aqueous layer was brought to pH5 and extracted with tert.-butylmethylether.
All organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the pale yellow crystalline boronic acid which was used for the next step without further purification.
yield: 9.4 g (83percent); MS 196 (M+).
Reference: [1] Patent: US6410562, 2002, B1,
  • 3
  • [ 23145-05-3 ]
  • [ 5419-55-6 ]
  • [ 223576-64-5 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387
  • 4
  • [ 23145-05-3 ]
  • [ 5419-55-6 ]
  • [ 7732-18-5 ]
  • [ 223576-64-5 ]
Reference: [1] Patent: WO2012/119046, 2012, A2, . Location in patent: Page/Page column 69
  • 5
  • [ 106-48-9 ]
  • [ 223576-64-5 ]
Reference: [1] Patent: WO2012/119046, 2012, A2,
[2] Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387
  • 6
  • [ 41964-04-9 ]
  • [ 223576-64-5 ]
Reference: [1] Patent: WO2012/119046, 2012, A2,
  • 7
  • [ 4122-68-3 ]
  • [ 223576-64-5 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387
  • 8
  • [ 122-88-3 ]
  • [ 223576-64-5 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387
  • 9
  • [ 3261-05-0 ]
  • [ 223576-64-5 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387
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