14135-38-7|2,2'-Difluorodiphenyldisulfide| Ambeed

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Quality Control of [ 14135-38-7 ] Purity: 98% SDS Specification

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Product Details of [ 14135-38-7 ]

CAS No. :	14135-38-7
Formula :	C₁₂H₈F₂S₂
M.W :	254.32
SMILES Code :	FC1=CC=CC=C1SSC1=C(F)C=CC=C1
MDL No. :	MFCD09029446
InChI Key :	BSLPHWROVJBMHX-UHFFFAOYSA-N
Pubchem ID :	14740277

Safety of [ 14135-38-7 ]

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

Computational Chemistry of [ 14135-38-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	64.51
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	50.6 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.8
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	4.61
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	5.6
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.	5.22
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	4.5
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	4.55

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.68
Solubility	0.00534 mg/ml ; 0.000021 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-5.4
Solubility	0.00102 mg/ml ; 0.000004 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-5.7
Solubility	0.00051 mg/ml ; 0.000002 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	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.	-4.58 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	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)	2.52

Application In Synthesis of [ 14135-38-7 ]

* 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 [ 14135-38-7 ]

[ 14135-38-7 ] Synthesis Path-Downstream 1~35

1
[ 2924-28-9 ]
[ 14135-38-7 ]

References: [1]Journal of Organometallic Chemistry,1967,vol. 7,p. 357 - 359.

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[ 2557-78-0 ]
[ 14135-38-7 ]

Yield	Reaction Conditions	Operation in experiment
45%	With C17H14OPdC26H24P2S2; In melt; at 100℃; for 6h;Inert atmosphere; Green chemistry;	General procedure: The melt of catalyst (5 mole %) and appropriate aryl thiophenol (1 equiv.) was stirred under N2 atmosphere at 100 C for 6 hours. The progress of reaction was monitored by thin layer chromatography. After 6 hours the reaction mixture was diluted with ethyl acetate and filtered through a sintered glass funnel. The filtrate was further washed with brine (X 3) and dried over Na2SO4 and concentrated under reduced pressure. The oily mass obtained was purified by column chromatography using hexane afford the desired compounds 2a-k.
	With sulfuryl dichloride; In dichloromethane; at 0℃; for 0.5h;	i) l J '-dithiobis(2-fluorobenzene')Sulfuryl chloride (0.7ml) was added dropwise to a solution of 2-fluorobenzenethiol (1.5ml) in DCM (20ml) at O0C. The reaction mixture was stirred for 30 min, then concentrated under EPO <DP n="35"/>reduced pressure. The residue was purified by chromatography on silica eluting with isohexane to give the sub-title compound as an oil, yield 1.7g. MS: APCI(+ve) 254 (M+H)
	With N-chloro-succinimide; In dichloromethane; at 20℃; for 0.5h;	General procedure: To the stirred solution of thiols (5 mmol) in dichloromethane (10 mL),NCS (0.5 eq.) was added. The mixture was then stirred for 30 min. The progressof the reaction was monitored by TLC. After completion of the reaction, CH2Cl2(10 mL) was added and the mixture was washed successively with water (2×20mL).The organic layer was separated and dried by adding anhydrous Na2SO4.Evaporation of the solvent under reduced pressure gave almost pure product.Further purication was achieved by column chromatography on silica gel (ethyl acetate:hexane (1:30)) to give pure product in good to excellent yield.

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2180 - 2186.
[2]Organic Letters,2018,vol. 20,p. 6274 - 6278.
[3]Tetrahedron Letters,1990,vol. 31,p. 5007 - 5010.
[4]Tetrahedron Letters,2017,vol. 58,p. 527 - 530.
[5]Patent: WO2007/39741,2007,A1 .Location in patent: Page/Page column 33-34.
[6]Tetrahedron Letters,2015,vol. 56,p. 4305 - 4307.
[7]Organic and Biomolecular Chemistry,2014,vol. 12,p. 9557 - 9561.
[8]ChemistryOpen,2016,vol. 5,p. 315 - 318.
[9]Chemical Communications,2017,vol. 53,p. 12197 - 12200.
[10]Angewandte Chemie - International Edition,2019,vol. 58,p. 1950 - 1954.
Angew. Chem.,2019,vol. 131,p. 1970 - 1974,5.

3
[ 14135-38-7 ]
3-(3-Fluoro-phenyl)-N-[2-(2-{3-(3-fluoro-phenyl)-2-[(E)-hydroxyimino]-propionylamino}-ethyldisulfanyl)-ethyl]-2-[(E)-hydroxyimino]-propionamide [ No CAS ]
3-(3-fluoro-phenyl)-<i>N</i>-[2-(2-fluoro-phenyldisulfanyl)-ethyl]-2-hydroxyimino-propionamide [ No CAS ]

References: [1]Chemistry - A European Journal,2001,vol. 7,p. 4296 - 4310.

4
[ 659-28-9 ]
[ 14135-38-7 ]
[ 447460-19-7 ]

Yield	Reaction Conditions	Operation in experiment
62%		Preparation of Sch 425084 Compound 29. To a solution of N,N,N-Trimethylethylenediamine (1.2 mL, 8.6 mmol) in THF (8 mL) at -20 C. was added n-BuLi (1.6 M, 5.4 mL, 8.6 mmol) dropwise. After 15 min 4-trifluoromethoxybenzaldehyde (1.5 g, 7.8 mmol) in THF (8 mL) was added. The mixture was stirred for 15 minutes and additional n-BuLi (1.6M, 14.6 mL, 23 mmol) was added. The reaction mixture was stirred at -20 C. for 1 h, then placed in the freezer at -20 C. for 20 h. The mixture was cooled to -40 C, and a solution of bis(2-fluorophenyl)disulfide (4.0 g, 15.7 mmoles) in 30 mL THF was added. The reaction mixture was stirred at -35 C. for 3 h. The reaction mixture was poured into 0.5 N HCl and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated to an oil. Purification by sgc (3percent EtOAc/hexanes) gave 1.55 g (62percent) of Compound 29 as a solid.

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4417 - 4420.
[2]Patent: US2003/232859,2003,A1 .Location in patent: Page 43.

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[ 447460-23-3 ]