[ CAS No. 657-46-5 ] {[proInfo.proName]}

Name: 657-46-5|1-Fluoro-3-(methylsulfonyl)benzene|95%
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SKU: A314268
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Quality Control of [ 657-46-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 657-46-5 ]

SDS Specification

Alternatived Products of [ 657-46-5 ]

Product Details of [ 657-46-5 ]

CAS No. :	657-46-5	MDL No. :	MFCD11519068
Formula :	C₇H₇FO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JTKXOVHBLURUOP-UHFFFAOYSA-N
M.W :	174.19	Pubchem ID :	21730266
Synonyms :

Calculated chemistry of [ 657-46-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.49
TPSA :	42.52 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.37
Log Po/w (XLOGP3) :	0.99
Log Po/w (WLOGP) :	2.73
Log Po/w (MLOGP) :	1.95
Log Po/w (SILICOS-IT) :	1.54
Consensus Log Po/w :	1.72

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.88
Solubility :	2.29 mg/ml ; 0.0131 mol/l
Class :	Very soluble
Log S (Ali) :	-1.47
Solubility :	5.88 mg/ml ; 0.0338 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.98
Solubility :	0.18 mg/ml ; 0.00104 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.76

Safety of [ 657-46-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 657-46-5 ]

* 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 [ 657-46-5 ]
Downstream synthetic route of [ 657-46-5 ]

[ 657-46-5 ] Synthesis Path-Upstream 1~12

1
[ 701-27-9 ]
[ 74-88-4 ]
[ 657-46-5 ]

Reference： [1] Patent: US2010/273816, 2010, A1, . Location in patent: Page/Page column 40

2
[ 2557-77-9 ]
[ 74-88-4 ]
[ 657-46-5 ]

Reference： [1] Patent: US2010/273816, 2010, A1, . Location in patent: Page/Page column 41

3
[ 1073-06-9 ]
[ 20277-69-4 ]
[ 657-46-5 ]

Reference： [1] Patent: US2010/273816, 2010, A1, . Location in patent: Page/Page column 41

4
[ 331-55-5 ]
[ 657-46-5 ]

Reference： [1] Journal of the Korean Chemical Society, 2014, vol. 58, # 1, p. 17 - 24
[2] Journal of the Serbian Chemical Society, 2015, vol. 80, # 8, p. 1019 - 1034
[3] Polyhedron, 2016, vol. 115, p. 164 - 173

5
[ 2557-77-9 ]
[ 657-46-5 ]

Reference： [1] Journal of the American Chemical Society, 1963, vol. 85, p. 709 - 724
[2] Journal of the Korean Chemical Society, 2014, vol. 58, # 1, p. 17 - 24
[3] Polyhedron, 2016, vol. 115, p. 164 - 173

6
[ 1121-86-4 ]
[ 67-68-5 ]
[ 657-46-5 ]

Reference： [1] Chemical Communications, 2012, vol. 48, # 60, p. 7513 - 7515

7
[ 3996-49-4 ]
[ 657-46-5 ]

Reference： [1] Journal of the Korean Chemical Society, 2014, vol. 58, # 1, p. 17 - 24
[2] Polyhedron, 2016, vol. 115, p. 164 - 173

8
[ 658-28-6 ]
[ 657-46-5 ]

Reference： [1] Journal of the American Chemical Society, 1963, vol. 85, p. 709 - 724

9
[ 625-98-9 ]
[ 657-46-5 ]

Reference： [1] Journal of the American Chemical Society, 1963, vol. 85, p. 709 - 724

10
[ 3112-85-4 ]
[ 657-46-5 ]
[ 654-47-7 ]

Reference： [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 10, p. 1462 - 1464

11
[ 462-06-6 ]
[ 7143-01-3 ]
[ 455-15-2 ]
[ 657-46-5 ]
[ 654-47-7 ]

Reference： [1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 21, p. 3150 - 3154

12
[ 3112-85-4 ]
[ 657-46-5 ]

Reference： [1] Journal of the Chemical Society [Section] B: Physical Organic, 1969, p. 646 - 648

[ 657-46-5 ] Synthesis Path-Downstream 1~27

1
[ 3112-85-4 ]
[ 657-46-5 ]

Reference： [1]Journal of the Chemical Society B: Physical Organic,1969,p. 646 - 648

2
[ 658-28-6 ]
[ 657-46-5 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8925 - 8929
[2]Journal of the American Chemical Society,1963,vol. 85,p. 709 - 724

5
[ 3112-85-4 ]
[ 657-46-5 ]
[ 654-47-7 ]
methyl 3,3,6,6-tetrafluoro-1,4-cyclohexadienyl sulfone [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2002,vol. 38,p. 1462 - 1464

6
[ 462-06-6 ]
[ 7143-01-3 ]
[ 455-15-2 ]
[ 657-46-5 ]
[ 654-47-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 3150 - 3154

7
[ 2557-77-9 ]
[ 657-46-5 ]

Reference： [1]Journal of the American Chemical Society,1963,vol. 85,p. 709 - 724
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 17 - 24
[3]Polyhedron,2016,vol. 115,p. 164 - 173

8
[ 625-98-9 ]
[ 657-46-5 ]

Reference： [1]Journal of the American Chemical Society,1963,vol. 85,p. 709 - 724

9
[ 657-46-5 ]
[ 73874-95-0 ]
[ 1033955-55-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; for 48h;Heating / reflux;	step 1-A mixture of <strong>[657-46-5]1-fluoro-3-methanesulfonyl-benzene</strong> (5 mmol) and 116 (5 mmol) in DIPEA (1 mL) and DMSO (10 mL) was heated at reflux for 48 h. After cooling, the mixture was poured into water (50 mL) and extracted with EtOAc. The organic phase was (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluding with EtOAc/hexane (1:2) to afford 0.970 g (77%) of 120a as white solid.

Reference： [1]Patent: US2008/146595,2008,A1 .Location in patent: Page/Page column 32

10
[ 1167570-75-3 ]
[ 657-46-5 ]
[ 1167570-79-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; In N,N-dimethyl-formamide; at 150℃;	A mixture of 3-(2-methyl-8-(trifluoromethyl)imidazo[ 1 ,2-a]pyridin-3-yl)phenol (0.100 g, 0.342 mmol), 1 -fluoro-3-(methylsulfonyl)benzene (0.119 g, 0.684 mmol) and potassium carbonate (0.095 g, 0.684 mmol) in DMF (3 mL) was heated at 150 0C overnight. The reaction mixture was cooled, diluted with water and extracted with several portions of ethyl acetate. The combined organics were washed with half-saturated brine and dried over MgSO4. The extracts were concentrated in vacuo and chromatographed using a 0:100 to 25:75 E:H gradient to afford the title compound as a white solid (0.096 g, 63%). MS (ES) m/z 447 '.2; HRMS: calcd for C22HnF3N2O3S + H+, 447.09847; found (ESI, [M+H]+), 447.0981.

Reference： [1]Patent: WO2009/86123,2009,A1 .Location in patent: Page/Page column 81

11
[ 1167570-76-4 ]
[ 657-46-5 ]
[ 1167570-88-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate; In N,N-dimethyl-formamide; at 150℃;	A mixture of 3-(2-ethyl-8-(trifluoromethyl)imidazo[l ,2-a]pyridin-3-yl)phenol (0.100 g, 0.326 mmol), l-fluoro-3-(methylsulfonyl)benzene (0.114 g, 0.653 mmol) and potassium carbonate (0.090 g, 0.653 mmol) in DMF (3 mL) was heated at 150 0C overnight. The reaction mixture was cooled, diluted with water and extracted with several portions of ethyl acetate. The combined organics were washed with half-saturated brine and dried over MgSO4. The extracts were concentrated onto Celite and chromatographed, typically using a 0:100 to 40:60 E:H gradient to afford the title compound as a white solid (0.163 g, 50%). HRMS: calcd for C23Hi9F3N2O3S + H+, 461.11412; found (ESI, [M+H]+), 461.1149.

Reference： [1]Patent: WO2009/86123,2009,A1 .Location in patent: Page/Page column 83

12
[ 626-02-8 ]
[ 657-46-5 ]
[ 1167571-52-9 ]

Yield	Reaction Conditions	Operation in experiment
28%	With potassium carbonate; In N,N-dimethyl-formamide; at 150℃; for 48h;Product distribution / selectivity;	A mixture of 3-iodophenol (2.64 g, 12.0 mmol), l-fluoro-3-(methylsulfonyl)benzene (1.74 g, 10.0 mmol), and K2CO3 (2.07 g, 15 mmol) in DMF (40 mL) was heated at 150 0C for 48 h. After cooling, the mixture was partitioned between EtOAc (150 mL) and water (80 mL). The layers were separated and the organic layer was washed with aqueous 2N HCl (40 mL), aqueous 2N NaOH (3 x 40 mL), water (4 x 40 mL) and brine (80 mL). The solution was dried over Na2SO4, concentrated, and the residue was purified by SiO2 flash chromatography eluting with a 0:100 to 25:75 E:H gradient. The residue was then purified by C18-reverse phase chromatography eluting with a gradient of 5:95 to 50:50 CH3CN:H2O to yield the title compound as a light- yellow gum (1.00 g, 28%). MS (ES) m/z 374.6.

Reference： [1]Patent: WO2009/86138,2009,A1 .Location in patent: Page/Page column 93-94

13
[ 1221265-56-0 ]
[ 657-46-5 ]
[ 1225650-98-5 ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium carbonate; In N,N-dimethyl acetamide; at 180℃; for 1h;Microwave irradiation;	Step 3: To a reaction vial suitable for microwave reactions containing a magnetic stir bar was placed 3-(3-methyl-5-(trifluoromethyl)quinoxalin-2-yl)phenol (50 mg, 0.164 mmol), <strong>[657-46-5]1-fluoro-3-(methylsulfonyl)benzene</strong> (57 mg, 0.328 mmol) and K2CO3 (68 mg, 0.493 mmol) in DMA (4 ml). The vial was capped put in a microwave reactor (Personal Chemistry unit) and the sample was irradiated at 180 C. for 1 h. Cooling to room temperature and partition between EtOAc and H2O (5 ml each), extraction, separation, extraction of the aqueous layer with EtOAc (4 ml). All organics combined, dried MgSO4, filtration concentration in vacuo to a brown powder. To this same powder was purified by RP-HPLC (H2O:AcCN) to afford the title compound as a red powder (36 mg, 48% yield). MS (ES) m/z 459.0; HRMS: calcd for C23H17F3N2O3S+H+, 459.09847. found (ESI, [M+H]+ Obs'd), 459.0984.

Reference： [1]Patent: US2010/120778,2010,A1 .Location in patent: Page/Page column 21

14
[ 854771-80-5 ]
[ 657-46-5 ]
[ 1020735-51-6 ]