4712-55-4|Diphenyl phosphite| Ambeed

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Structure of Diphenyl phosphite
CAS No.: 4712-55-4

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Quality Control of [ 4712-55-4 ] Purity: 75% SDS Specification

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Product Details of [ 4712-55-4 ]

CAS No. :	4712-55-4
Formula :	C₁₂H₁₁O₃P
M.W :	234.19
SMILES Code :	O=P(OC1=CC=CC=C1)OC2=CC=CC=C2
MDL No. :	MFCD00044497
InChI Key :	CDXVUROVRIFQMV-UHFFFAOYSA-N
Pubchem ID :	6327546

Safety of [ 4712-55-4 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H318-H335
Precautionary Statements:	P261-P280-P305+P351+P338
Class:	8
UN#:	1760
Packing Group:	Ⅲ

Computational Chemistry of [ 4712-55-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	63.14
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	59.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.14
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	3.09
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.53
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.	2.67
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	3.59
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.53
Solubility	0.0692 mg/ml ; 0.000295 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.0
Solubility	0.0236 mg/ml ; 0.000101 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-4.42
Solubility	0.0089 mg/ml ; 0.000038 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	No
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	No
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.	-5.53 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	0.0
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	0.0
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<1.0
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)	3.36

Application In Synthesis of [ 4712-55-4 ]

* 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 [ 4712-55-4 ]

[ 4712-55-4 ] Synthesis Path-Downstream 1~17

1
[ 67442-07-3 ]
[ 4712-55-4 ]
[ 367508-01-8 ]

References: [1]Heteroatom Chemistry,2004,vol. 15,p. 515 - 523.
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 11594 - 11598.
Angew. Chem.,2017,vol. 129,p. 11752 - 11756,5.

2
[ 23377-40-4 ]
[ 4712-55-4 ]
[ 136982-89-3 ]
[ 883989-38-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2178 - 2189.

3
[ 4712-55-4 ]
[ 1095-03-0 ]

References: [1]Journal of the Chemical Society,1960,p. 4037 - 4039.

4
[ 4712-55-4 ]
[ 100-51-6 ]
[ 20724-73-6 ]
C₁₇H₂₂N₃O₇P [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5394 - 5407.

5
[ 40299-87-4 ]
[ 4712-55-4 ]
[ 1190210-95-7 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 5689 - 5691.

6
[ 1123-93-9 ]
[ 4712-55-4 ]
2-cyclopropyl pyrimidine 4-carbaldehyde [ No CAS ]
[ 1610793-27-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With phosphomolybdic acid; In dichloromethane; at 20℃; for 0.333333h;Inert atmosphere;	General procedure: A mixture of the 2-cyclopropylpyrimidine 4-carbaldehyde (4) (0.148g, 1.0 mmol), aniline (5a) (0.093 g, 1.0 mmol) and diphenyl phosphite (6a) (0.280 g, 1.2 mmol) were taken into a 25 ml round bottomflask in dry dichloromethane (10 ml) in the presence of 0.5 molpercent of phosphomolybidic acid (0.0370 g, 0.02 mmol) was stirred at room temperature for20 min. The progress of the reaction was monitored by TLC analysis. Aftercompletion of the reaction solvent was filtered to recover the catalyst. The filtrate was evaporated under reduced pressure and the residue was purified bycolumn chromatography on silica gel (100-200 mesh) using 20-30percent petroleum etherand ethyl acetate as eluents to obtain the pure alpha-aminophosphonate as a solid (7a) in 95percent (0.434 g) yield. This procedure was applied successfully for the preparation of other compounds 7b-n (Table 2).
90%	With hydrogen trititanate; In neat (no solvent); at 20℃; for 0.25h;Green chemistry;	General procedure: Dialkyl/diaryl phosphite (1.0 mmol) was added portion wise over a period of 5 min to the stirred mixture of heterocyclic aldehyde (1.0 mmol) and benzothiazole amine (1.0 mmol) at room temperature. Further 5 mol percent of TNT was added to the reaction mixture and the stirring was continued for 15 min. After the completion of the reaction as monitored through TLC, the reaction mixture was dissolved in EtOAc (2 mL) and the catalyst was separated by centrifugation followed by subsequent washings with EtOAc. The recovered catalyst was reused for the next cycle. The filtrate was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated on a rotary evaporator and the resulting residue was purified by silica gel column chromatography (70:30, hexane/EtOAc) to afford the corresponding pure alpha-aminophosphonate. The novel alpha-aminophosphonates were structurally assigned by their IR, NMR (1H, 13C & 31P), and mass spectral (HRMS) analyses.

References: [1]Tetrahedron Letters,2014,vol. 55,p. 3336 - 3339.
[2]Tetrahedron Letters,2016,vol. 57,p. 696 - 702.

7
[ 4712-55-4 ]
[ 161798-01-2 ]
C₂₆H₂₄NO₇PS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With N,N'-dimethylpiperazine; In tetrahydrofuran; at 60℃; for 3h;	Synthesis of dibutyl (5-(5-ethyl-4-methylthiazol-2-yl)-2-hydroxyphenyl) (hydroxy) methyl phosphonate (3a). Amixture of febuxostat aldehyde (0.002 mole), dibutylphosphite(0.002 mole), and 1, 4-dimethylpiperazine (0.002 mole) wasrefluxed for 3 h in tetrahydrofuran (THF) (20 mL) at 60°C.The progress of the reaction was monitored by TLC analysis.After completion of the reaction, as indicated by TLC (silicagel) using hexane and ethyl acetate (3:1) as a mobile phase, thesolvent was removed in a rota-evaporator and the crude productobtained was purified by column chromatography on silica gel(60?120 mesh) using hexane and ethyl acetate (3:1) as an eluentto afford the analytically pure 3a. Analogously, the compounds3b?d were prepared by adopting the above procedure.

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,2016,vol. 191,p. 95 - 99.

8
[ 1123-93-9 ]
[ 23145-19-9 ]
[ 4712-55-4 ]
diphenyl (benzo[d]thiazol-5-ylamino)(5-methoxybenzofuran-2-yl)methylphosphonate [ No CAS ]