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[ CAS No. 13885-09-1 ] {[proInfo.proName]}

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Chemical Structure| 13885-09-1
Chemical Structure| 13885-09-1
Structure of 13885-09-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 13885-09-1 ]

CAS No. :13885-09-1 MDL No. :MFCD11559063
Formula : C24H19P Boiling Point : -
Linear Structure Formula :P(C6H5)2C12H9 InChI Key :FNCQSSIMHQVKGF-UHFFFAOYSA-N
M.W : 338.38 Pubchem ID :12976978
Synonyms :

Calculated chemistry of [ 13885-09-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 110.58
TPSA : 13.59 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.67
Log Po/w (XLOGP3) : 6.23
Log Po/w (WLOGP) : 5.11
Log Po/w (MLOGP) : 6.27
Log Po/w (SILICOS-IT) : 7.03
Consensus Log Po/w : 5.66

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.31
Solubility : 0.000166 mg/ml ; 0.000000491 mol/l
Class : Poorly soluble
Log S (Ali) : -6.3
Solubility : 0.000169 mg/ml ; 0.0000005 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -10.03
Solubility : 0.0000000319 mg/ml ; 0.0000000001 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.28

Safety of [ 13885-09-1 ]

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 [ 13885-09-1 ]

* 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 [ 13885-09-1 ]
  • Downstream synthetic route of [ 13885-09-1 ]

[ 13885-09-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 2113-51-1 ]
  • [ 829-85-6 ]
  • [ 13885-09-1 ]
YieldReaction ConditionsOperation in experiment
61% With potassium acetate In N,N-dimethyl acetamide at 130℃; for 3 h; Schlenk technique; Inert atmosphere General procedure: MCM-41-3N-Pd(0) (21mg, 0.01mmol), KOAc (1.5mmol) and aryl iodide 1 (1.0mmol) (if solid) were placed in an oven-dried 20mL Schlenk tube, the reaction vessel was evacuated and filled with argon for three times. Then aryl iodide 1 (1.0mmol) (if liquid), diphenylphosphine (1.2mmol) and DMAc (1mL) were added with a syringe under a counter flow of argon. The reaction mixture was stirred at 130°C for 3h. After completion of the reaction, the mixture was cooled to room temperature and diluted with CH2Cl2 (20mL) and filtered. The MCM-41-3N-Pd(0) catalyst was washed with distilled water (2×5mL) and ethanol (2×5mL), and reused in the next run. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel to provide the product 2.
Reference: [1] Organic Letters, 2003, vol. 5, # 13, p. 2315 - 2318
[2] Applied Organometallic Chemistry, 2018, vol. 32, # 8,
[3] Journal of Organometallic Chemistry, 2018, vol. 866, p. 50 - 58
  • 2
  • [ 2113-51-1 ]
  • [ 40841-62-1 ]
  • [ 13885-09-1 ]
YieldReaction ConditionsOperation in experiment
92% With palladium diacetate; caesium carbonate In toluene at 80℃; for 12 h; Sealed tube; Inert atmosphere General procedure: In a sealed vial, under nitrogen, p-methylbenzoyldiphenylphosphine (61 Cs2CO3 mg, 0.20 mmol, 1.0 equiv), Pd(OAc)2 (1.4 mg, 0.006 mmol), aryl iodides (0.21mmol, 1.05 equiv), (72 mg, 0.22 mmol, 1.1 equiv) and toluene (0.5 mL) were mixed and stirred at 80 oC for 12 h. When reaction completed, the reaction mixture was directly purified by flash column chromatography on silica gel to give pure product.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 30, p. 3404 - 3406
  • 3
  • [ 1942-82-1 ]
  • [ 13885-09-1 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 51, p. 9085 - 9088
[2] Tetrahedron, 2004, vol. 60, # 19, p. 4159 - 4168
  • 4
  • [ 2052-07-5 ]
  • [ 1079-66-9 ]
  • [ 13885-09-1 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 12, p. 5697 - 5705
[2] Organic Letters, 2013, vol. 15, # 20, p. 5302 - 5305
[3] Organic Letters, 2013, vol. 15, # 24, p. 6186 - 6189
[4] Chemical Communications, 2014, vol. 50, # 36, p. 4686 - 4689
[5] Organic Letters, 2017, vol. 19, # 7, p. 1842 - 1845
  • 5
  • [ 583-55-1 ]
  • [ 13885-09-1 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 19, p. 4159 - 4168
[2] Tetrahedron, 2004, vol. 60, # 19, p. 4159 - 4168
[3] Organic Letters, 2013, vol. 15, # 20, p. 5302 - 5305
[4] Organic Letters, 2013, vol. 15, # 24, p. 6186 - 6189
[5] Chemical Communications, 2014, vol. 50, # 36, p. 4686 - 4689
[6] Organic Letters, 2017, vol. 19, # 7, p. 1842 - 1845
  • 6
  • [ 98-80-6 ]
  • [ 13885-09-1 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 11, p. 2127 - 2131
[2] Organic Letters, 2013, vol. 15, # 20, p. 5302 - 5305
[3] Organic Letters, 2013, vol. 15, # 24, p. 6186 - 6189
[4] Chemical Communications, 2014, vol. 50, # 36, p. 4686 - 4689
[5] Organic Letters, 2017, vol. 19, # 7, p. 1842 - 1845
  • 7
  • [ 2051-60-7 ]
  • [ 1079-66-9 ]
  • [ 13885-09-1 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 11, p. 2127 - 2131
  • 8
  • [ 62336-24-7 ]
  • [ 98-80-6 ]
  • [ 13885-09-1 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 51, p. 9085 - 9088
  • 9
  • [ 88652-74-8 ]
  • [ 13885-09-1 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 19, p. 4159 - 4168
[2] Tetrahedron Letters, 2001, vol. 42, # 51, p. 9085 - 9088
  • 10
  • [ 829-85-6 ]
  • [ 13885-09-1 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 19, p. 4159 - 4168
[2] Tetrahedron Letters, 2016, vol. 57, # 30, p. 3404 - 3406
  • 11
  • [ 4559-70-0 ]
  • [ 13885-09-1 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 19, p. 4159 - 4168
  • 12
  • [ 62336-24-7 ]
  • [ 13885-09-1 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 19, p. 4159 - 4168
  • 13
  • [ 95-50-1 ]
  • [ 13885-09-1 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 11, p. 2127 - 2131
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