32431-75-7|Methyl 4-fluorothiophene-2-carboxylate| Ambeed

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Quality Control of [ 32431-75-7 ] Purity: 95% SDS Specification

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Product Details of [ 32431-75-7 ]

CAS No. :	32431-75-7
Formula :	C₆H₅FO₂S
M.W :	160.17
SMILES Code :	O=C(C1=CC(F)=CS1)OC
MDL No. :	MFCD11618006
InChI Key :	XQDIKAOOGCLKQR-UHFFFAOYSA-N
Pubchem ID :	15533897

Safety of [ 32431-75-7 ]

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

Computational Chemistry of [ 32431-75-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	5
Fraction Csp3	0.17
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	35.56
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.54 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.08
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	1.89
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.09
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.	1.35
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	2.79
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.04

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.26
Solubility	0.877 mg/ml ; 0.00547 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.	-2.66
Solubility	0.352 mg/ml ; 0.0022 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	-2.01
Solubility	1.57 mg/ml ; 0.00977 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	No
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.	-5.94 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	1.0
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	0.0 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)	2.2

Application In Synthesis of [ 32431-75-7 ]

* 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 [ 32431-75-7 ]

[ 32431-75-7 ] Synthesis Path-Downstream 1~24

2
[ 32431-75-7 ]
[ 395664-59-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With bromine; In chloroform; at 60℃; for 1h;	Synthesis of methyl 5-bromo-4-fluorothiophene-2-carboxylateBr2 (2.29 g, 14.4 mmol, 0.740 ml) was added to a mixture of <strong>[32431-75-7]methyl 4-fluorothiophene-2-carboxylate</strong>(0.230 g, 1.43 mmol) in CHCI3 (5 mL) and the mixture was warmed up to 60 00 and stirred for 1 h. Thesolution was cooled to RT and poured in an aqueous solution of Na2S2O3 (10%, 10 mL) and stirred for 30 mm. The phases were separated and the aqueous layer extracted with DCM (3x 10 mL). The collected organic layer was washed with brine (20 mL), dried over Na2SO4 and evaporated in vacuo to leave a yellow solid (0.800 g). The solid was sublimated in the kugelrohr at 150 C under vacuum (50 torr) to yield methyl 5-bromo-4-fluorothiophene-2-carboxylate 0.280 g 1.17 mmol, 82%).

References: [1]Tetrahedron Letters,2001,vol. 42,p. 8797 - 8800.
[2]Patent: WO2015/161928,2015,A1 .Location in patent: Page/Page column 55; 56.

3
[ 89499-43-4 ]
[ 32431-75-7 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 8797 - 8800.

4
[ 7311-63-9 ]
[ 32431-75-7 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 8797 - 8800.

5
[ 62224-19-5 ]
[ 32431-75-7 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 8797 - 8800.

6
[ 32431-75-7 ]
5-(4-dodecyloxy-phenyl)-4-fluoro-thiophene-2-carboxylic acid [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 8797 - 8800.

7
[ 32431-75-7 ]
[ 395664-69-4 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 8797 - 8800.

8
[ 32431-75-7 ]
5-(4-Dodecyloxy-phenyl)-4-fluoro-thiophene-2-carboxylic acid 4-((R)-1-methyl-heptyloxycarbonyl)-phenyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 8797 - 8800.

9
[ 38239-32-6 ]
[ 32431-75-7 ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 8797 - 8800.

10
5-(methoxycarbonyl)thiophene-3-diazonium hexafluorophosphate [ No CAS ]
[ 32431-75-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	With silica gel; at -78 - 250℃;Inert atmosphere;	Synthesis of methyl 4-fluorothiophene-2-carboxylateA mixture of 5-(methoxycarbonyl)thiophene-3-diazonium hexafluorophosphate (5.50 g, 15.9 mmol) and sand (30 g) was warmed to 250 C under vacuum (0.01 torr) in a Kugelrohr apparatus equipped with a trap at -78 00 and two traps in liquid N2. A yellow liquid started to distill and condensed in the traps and it was carefully collected using Et20 as solvent. The solvent was evaporated to give methyl 4-fluorothiophene-2-carboxylate (1.5 g, 9.4 mmol, 59%). GCMS: calc. for [M]160.00, found 160.0.

References: [1]Patent: WO2015/161928,2015,A1 .Location in patent: Page/Page column 55.

11
[ 32431-75-7 ]
4-fluoro-5-(pyrimidin-5-yl)thiophene-2-carboxylic acid [ No CAS ]

References: [1]Patent: WO2015/161928,2015,A1 .

12
[ 32431-75-7 ]
methyl 4-fluoro-5-(pyrimidin-5-yl)thiophene-2-carboxylate [ No CAS ]

References: [1]Patent: WO2015/161928,2015,A1 .

13
methyl 4-aminothiophene-2-carboxylate hydrobromide [ No CAS ]
[ 32431-75-7 ]

References: [1]Patent: WO2015/161928,2015,A1 .

14
[ 32431-75-7 ]
[ 1007388-28-4 ]

Yield	Reaction Conditions	Operation in experiment
77.6%	With sodium tetrahydroborate; ethanol; at 0 - 20℃; for 16.5h;	Into a 1000-mL round-bottom flask, was placed <strong>[32431-75-7]methyl 4-fluorothiophene-2-carboxylate</strong> (10 g, 62.4 mmol) in ethanol (300 mL). Then to the above solution was added NaBH4(4.62 g, 125 mmol) in portions at 0C in an ice/ethanol bath. The resulting solution was stirred for 30 min at 0C and then the reaction solution was allowed to react for an additional 16 h at RT. The reaction was then quenched by the addition of 50 mL of water. Then the mixture was concentrated and extracted with 3xl00mL of ethyl acetate and the organic layers were combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 6.4 g (77.6%) of the title compound as white oil. MS-ESI: 133 (M+l)
77.5%	With sodium tetrahydroborate; ethanol; at 0 - 20℃; for 16.5h;Inert atmosphere;	Into a 1000-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed <strong>[32431-75-7]methyl 4-fluorothiophene-2-carboxylate</strong> (10 g, 62.4 mmol) in EtOH (300 mL). To the above solution was added NaBH4 (4.74 g, 124.8 mmol) with stirring at 0C. Theresulting solution was stirred for 30 mm at 0C. The resulting solution was allowed to react for an additional 16 h at RT. The reaction was then quenched by the addition of 10 mL of water. The resulting mixture was extracted with 3x1000 mL of ethyl acetate. Evaporation of combined ethyl acetate solution resulted in 6.4 g (77.5%) of the title compound as white oil.

References: [1]Patent: WO2019/23147,2019,A1 .Location in patent: Page/Page column 504.
[2]Patent: WO2019/23145,2019,A1 .Location in patent: Page/Page column 423.

15
[ 32431-75-7 ]
2-(bromomethyl)-4-fluorothiophene [ No CAS ]