29949-85-7|Tris(3-chlorophenyl)phosphine| Ambeed

CAS No. :	29949-85-7
Formula :	C₁₈H₁₂Cl₃P
M.W :	365.62
SMILES Code :	ClC1=CC(P(C2=CC=CC(Cl)=C2)C3=CC=CC(Cl)=C3)=CC=C1
MDL No. :	MFCD00013632
InChI Key :	QAPGHLJQIVDTPT-UHFFFAOYSA-N
Pubchem ID :	121600

Safety of [ 29949-85-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 29949-85-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	22
Num. arom. heavy atoms	18
Fraction Csp3	0.0
Num. rotatable bonds	3
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	100.18
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	13.59 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	4.06
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	6.49
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	5.41
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	6.65
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	7.34
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	5.99

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-6.6
Solubility	0.0000912 mg/ml ; 0.000000249 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-6.57
Solubility	0.0000981 mg/ml ; 0.000000268 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-9.34
Solubility	0.000000168 mg/ml ; 0.0000000005 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-3.92 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	4.18

Application In Synthesis of [ 29949-85-7 ]

* 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.

Downstream synthetic route of [ 29949-85-7 ]

[ 29949-85-7 ] Synthesis Path-Downstream 1~53

1
[ 64-17-5 ]
[ 29949-85-7 ]
[ 127-65-1 ]
[ 54300-36-6 ]

References: [1]Journal of the Chemical Society,1937,p. 527,530.

2
[ 29949-85-7 ]
[ 127-65-1 ]
[ 54300-36-6 ]

References: [1]Journal of the Chemical Society,1937,p. 527,530.

3
[ 2892-63-9 ]
[ 29949-85-7 ]
[ 102268-48-4 ]

References: [1]Synthesis,1984,p. 754 - 757.

4
[ 2446-83-5 ]
[ 29949-85-7 ]
[ 84985-43-3 ]
C₃₄H₂₉Cl₃N₂O₇P⁽¹⁺⁾*C₈H₁₅N₂O₄^(1-) [ No CAS ]

References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 6487 - 6491.

5
[ 20057-88-9 ]
[ 29949-85-7 ]
[ 54300-45-7 ]
[ 882-33-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1992,p. 775 - 779.

6
[ 29949-85-7 ]
[ 76943-18-5 ]
C₂₂H₁₆Cl₃F₆O₂P [ No CAS ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1995,vol. 102,p. 195 - 204.

7
[ 29949-85-7 ]
[ 54300-36-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; In dichloromethane; at 0 - 20℃;	Under the protection of N2, dissolve 1-chloro-3-bromobenzene (5g) in 40mL ultra-dry tetrahydrofuran and put it in a Dewar flask at -78; add n-BuLi(16.4 mL) and stirred for 1h, then added phosphine trichloride (0.75mL), warmed to room temperature, stirred for 8-12 hours; added water (20mL) to quench the butyllithium, then distilled under reduced pressure to remove tetrahydrofuran; then extracted with water and CH2Cl2 Three times, the organic phase was collected and dried with anhydrous Na2SO4, and then distilled under reduced pressure to remove the solvent; finally purified by column chromatography to obtain m-TClPP; m-TClPP was dissolved in CH2Cl2 and placed in an ice-water bath at 0C, slowly dripping Add H2O2 (5 mL), then stir at room temperature for 2-4 hours. It was extracted three times with water and CH2Cl2, the organic phase was collected and dried with anhydrous Na2SO4 to remove water, and then distilled under reduced pressure to remove the solvent to obtain m-TClPPO as a white powder.

References: [1]Acta Crystallographica, Section C: Crystal Structure Communications,1997,vol. 53,p. 1451 - 1452.
[2]Phosphorus, Sulfur and Silicon and the Related Elements,1995,vol. 105,p. 145 - 156.
[3]Journal of Organic Chemistry,2013,vol. 78,p. 8098 - 8104.
[4]Patent: CN112940035,2021,A .Location in patent: Paragraph 0041; 0044-0046.

8
[ 64-17-5 ]
[ 29949-85-7 ]
sodium-<<i>N</i>-chloro-toluenesulfonamide-(4)-trihydrate [ No CAS ]
[ 54300-36-6 ]

References: [1]Journal of the Chemical Society,1937,p. 527,530.

10
3-chloro-phenyl magnesium iodide [ No CAS ]
[ 29949-85-7 ]

References: [1]Journal of the Chemical Society,1937,p. 527,530.

11
[ 29949-85-7 ]
selenium [ No CAS ]
[ 54300-56-0 ]

References: [1]Journal of general chemistry of the USSR,1981,vol. 51,p. 512 - 514.
Zhurnal Obshchei Khimii,1981,vol. 51,p. 642 - 644.

12
[ 29949-85-7 ]
[ 3474-40-6 ]
bis(3-chlorophenyl)phosphinyl radical [ No CAS ]

References: [1]Journal of Physical Chemistry A,2004,vol. 108,p. 3421 - 3429.

13
[ 114713-40-5 ]
[ 29949-85-7 ]
Cu(OCC(C(CH₃)3)CHC(C(CH₃)3)CHCNNC(CH)2CH(CH)2)(P(CCHCCl(CH)3)3)2 [ No CAS ]