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Chemical Structure| 126534-43-8
Chemical Structure| 126534-43-8
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Product Details of [ 126534-43-8 ]

CAS No. :126534-43-8 MDL No. :MFCD08064295
Formula : C8H8ClFO Boiling Point : -
Linear Structure Formula :- InChI Key :VTCREIYEGAGUDS-QMMMGPOBSA-N
M.W : 174.60 Pubchem ID :12300420
Synonyms :

Calculated chemistry of [ 126534-43-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.13
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 1.76
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.25

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.3
Solubility : 0.869 mg/ml ; 0.00498 mol/l
Class : Soluble
Log S (Ali) : -1.8
Solubility : 2.75 mg/ml ; 0.0158 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.17
Solubility : 0.119 mg/ml ; 0.000681 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.84

Safety of [ 126534-43-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501 UN#:1760
Hazard Statements:H302-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 126534-43-8 ]

* 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 [ 126534-43-8 ]

[ 126534-43-8 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 108-22-5 ]
  • [ 61592-48-1 ]
  • [ 134295-34-4 ]
  • [ 126534-43-8 ]
YieldReaction ConditionsOperation in experiment
1: 3.7 g 2: 4.3 g In diethyl ether for 48h; Ambient temperature; amano lipase P from Pseudomonas sp.;
  • 2
  • [ 61592-48-1 ]
  • [ 134295-34-4 ]
  • [ 126534-43-8 ]
YieldReaction ConditionsOperation in experiment
4.3 g
  • 3
  • [ 126534-43-8 ]
  • (S)-1-(4-fluorophenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Ambient temperature;
Multi-step reaction with 2 steps 1: 5.7 g / potassium carbonate / methanol; H2O / 3 h / Ambient temperature 2: 0.12 g / lithium aluminum hydride / tetrahydrofuran / 1 h / Ambient temperature
  • 4
  • [ 126534-43-8 ]
  • R-(-)-2-(4-fluorophenyl)oxirane [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.7 g With potassium carbonate In methanol; water for 3h; Ambient temperature;
  • 5
  • [ 876-27-7 ]
  • [ 61592-48-1 ]
  • [ 134295-34-4 ]
  • [ 126534-42-7 ]
  • [ 126534-43-8 ]
  • (R)-1-chloro-2-acetoxy-2-(p-fluorophenyl)ethane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Pseudomonas sp. lipase In toluene at 60℃; for 5h; Enzymatic reaction; Title compound not separated from byproducts.;
  • 6
  • [ 456-04-2 ]
  • [ 126534-42-7 ]
  • [ 126534-43-8 ]
YieldReaction ConditionsOperation in experiment
With benzo[1,3,2]dioxaborole In dichloromethane at 25℃; for 48h;
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; Title compound not separated from byproducts.;
63 %Chromat. With stems and germinated seed of Brassica oleracea variety italica In water at 20℃; for 48h; optical yield given as %ee; enantioselective reaction;
77.83 % ee With D-glucose; NADP; alcohol dehydrogenase derived from Lactobacillus kefir mutant LkADH-D18 (Y190C/V196L/M206H/D150H); glucose dehydrogenase (GDH) from Bacillus subtilis CGMCC 1.1398 In aq. buffer Enzymatic reaction; enantioselective reaction; Activity, stereoselectivity assay, and determination of kinetic parameters General procedure: The specific activities of LkADH-D18 were spectrophotometrically assayed by measuring the change in NADPH absorbance at 340 nm in 1 min. The reaction system contained the appropriate weights of the purified enzymes, 0.5 mM NADPH, 5 mM substrate dissolved in methanol, and 100 mM triethanolamine buffer (pH 7.6), at a final reaction volume of 200 μL. The kinetic parameters for 1a were determined by increasing the substrate concentration from 0.075 to 2.5 mM at 30 °C. Initial velocities at different substrate concentrations were used to generate a Lineweaver-Burk plot (1/v vs. 1/[S]). The stereoselectivity toward ketones with different substituents was also determined. The reaction system (500 µL) contained 155 µg purified LkADH-D18, 100 U glucose dehydrogenase (GDH) from Bacillus subtilis CGMCC 1.1398, 25 µL of 5 mM NADP stock, 10 µL of 200 mM 1a, 20 mM glucose, and 100 mM triethanolamine buffer (pH 7.6). The chiral HPLC analysis method is shown in Table S1.

  • 7
  • [ 456-04-2 ]
  • [ 126534-43-8 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 2-Chloro-4'-fluoroacetophenone With borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 20℃; for 105h; Inert atmosphere; Stage #2: With methanol In tetrahydrofuran Inert atmosphere; A Step A: (1 RV2-Chloro-1-(4-fluoro-pheny1Vethanol. To a solution consisting of BH3-THF (1 M1 150 mL) and (R)-(+)-2-methyl-CBS-oxazaborolidine (1 M in THF) (2.14 mL) was added a second solution consisting of 2-chloro-4'-fluoro- acetophenone (37.0 g, 214 mmol) and THF (100 ml) over 1 h at rt. The resultant colorless reaction mixture was stirred for 45 min and then quenched with MeOH (75 mL). The solvent was removed in vacuo leaving the title compound as pale yellow oil, which was used without further purification (37 g, 100%)
96% With Almag CRED A131; NADP; glucose dehydrogenase In water; dimethyl sulfoxide; isopropyl alcohol at 20℃; Enzymatic reaction; 4.4_B General procedure: Almac CRED (200 mg) and NADP or NAD (10 mg)were charged into a 100 mL round bottomed flask and dissolvedin 0.1 M potassium phosphate buffer (pH 7, ca. 50 mL). Next, IPA(7 mL) was added, followed by a solution of ketone (900-1700 mg) in DMSO (2.5-5 mL, depending on solubility). This was shaken at room temperature overnight and the reaction progresswas checked by 1H NMR. If not complete, additional CRED (100-200 mg) and NADP or NAD (10 mg) were added and shaking wascontinued. This was repeated until the reaction reached completion.If the reaction appeared to stall or proceed very slowly, experimentalmethod C was used.
94% With formic acid; C25H29N2O3RuS; potassium formate In water; ethyl acetate at 60℃; for 4h; Inert atmosphere; enantioselective reaction;
82% With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; isopropyl alcohol; NADPH; magnesium chloride In 2-methyltetrahydrofuran; water at 40℃; Enzymatic reaction; enantioselective reaction;
76% With isopropyl alcohol In dimethyl sulfoxide at 30℃; for 24h; Enzymatic reaction; enantioselective reaction;
With D-glucose; D-glucose dehydrogenase; NADPH In dimethyl sulfoxide at 20℃;
Multi-step reaction with 2 steps 1: 24.4 g / sodium borohydride / methanol / 1.5 h / Ambient temperature

  • 8
  • [ 126534-43-8 ]
  • [ 134295-41-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5.7 g / potassium carbonate / methanol; H2O / 3 h / Ambient temperature 2: 0.18 g / propan-2-ol / 2 h / Heating
Multi-step reaction with 2 steps 1: 5.7 g / potassium carbonate / methanol; H2O / 3 h / Ambient temperature 2: 0.06 g / propan-2-ol / 2 h / Heating
  • 9
  • [ 126534-43-8 ]
  • [ 134295-37-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5.7 g / potassium carbonate / methanol; H2O / 3 h / Ambient temperature 2: 1.2 g / propan-2-ol / 2 h / Heating
  • 10
  • [ 126534-43-8 ]
  • [ 134295-40-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5.7 g / potassium carbonate / methanol; H2O / 3 h / Ambient temperature 2: 1.06 g / propan-2-ol / 2 h / Heating
YieldReaction ConditionsOperation in experiment
27.b b) The compound obtained in Example 27 (a) (1.0 g, 5.73 mmol) was dissolved in diethyl ether (15 ml), and the solution was added with isopropenyl acetate (2.2 ml, 20 mmol) and lipase PS (Amano, immobilized Lipase PS on diatomite, 2.0 g), and then the mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered through Cerite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate = 10:1) to obtain (R)-(-)-2-chloro-(4-fluorophenyl)ethanol (393 mg, yield: 39%) and (S)-(+)-2-chloro-(4-fluorophenyl)ethanol acetate (511 mg, yield: 41%) both as colorless oil.
27 (R)-(-)-2-Chloro-(4-fluorophenyl)ethanol (R)-(-)-2-Chloro-(4-fluorophenyl)ethanol 1H-NMR (CDCl3): 7.35 (m, 2H), 7.06 (m, 2H), 4.88 (m, 2H), 3.64 (m, 2H), 2.70 (s, 1H) >99% e.e. (HPLC: Daicel CHIRALCEL OJ, UV 254 nm, hexane/ethanol = 95/5)
  • 12
  • [ 134295-34-4 ]
  • [ 126534-43-8 ]
  • (2S)-2-(4-fluorophenyl)oxirane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In methanol; water 28.a (a) (a) (S)-4-Fluorostyrene oxide The (S)-(+)-2-chloro-(4-fluorophenyl)ethanol acetate obtained in Example 27 (b) (565 mg, 2.61 mmol) was dissolved in methanol (10 ml) and water (5 ml), and the solution was added with sodium hydrogencarbonate (500 mg). The reaction mixture was stirred at 60°C for 1 hour, and then the solvent was evaporated under reduced pressure. The residue was added with water and extracted with methylene chloride. The organic layer was washed with water and dried over sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the title compound as colorless oil (300 mg, yield: 83%). 1H-NMR (CDCl3): 7.25 (m, 2H), 7.04 (m, 2H), 3.85 (t, 1H), 3.14 (m, 1H), 2.70 (s, 1H)
  • 13
  • 4-(6-chloro-2-methyliminobenzothiazolin-3-ylmethyl)piperidine [ No CAS ]
  • [ 126534-43-8 ]
  • (R)-1-(4-Fluorophenyl)-2-[4-(6-chloro-2-methyliminobenzothiazolin-3-yl-methyl)piperidin-1-yl]ethanol dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In ethanol; water 27.c c) c) (R)-1-(4-Fluorophenyl)-2-[4-(6-chloro-2-methyliminobenzothiazolin-3-ylmethyl)-piperidin-1-yl]ethanol dihydrochloride The (R)-(-)-2-chloro-(4-fluorophenyl)ethanol obtained in Example 27 (b) (340 mg, 1.95 mmol) was dissolved in ethanol (10 ml) and the solution was added with the 4-(6-chloro-2-methyl iminobenzothiazolin-3-ylmethyl)piperidine obtained in Example 4 (c) (577 mg, 1.95 mmol) and potassium carbonate (270 mg, 1.95 mmol), and then the mixture was stirred at 60°C for 4 hours. The deposited solid was collected by filtration, and washed with ethanol. The resulting solid was washed by suspending the solid in ethanol and water (1:1, 20 ml) at 60°C for 1 hour, then the solid was collected by filtration and washed with ethanol to obtain the free form of the title compound as white solid (534 mg, yield: 63%). Melting point: 211-212°C 1H-NMR (CDCl3): 7.31 (m, 3H), 7.18 (dd, 1H), 7.01 (m, 2H), 6.77 (d, 1H), 4.67 (dd, 1H), 3.80 (d, 2H), 3.12 (d, 1H), 3.08 (s, 3H), 2.81 (d, 1H), 2.44 (m, 2H), 2.27 (m, 1H), 1.98 (m, 2H), 1.67 (m, 2H), 1.43 (m, 2H)
  • 14
  • [ 126534-43-8 ]
  • [ 1184850-40-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium azide / N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere 2.1: hydrogen / 5%-palladium/activated carbon / ethanol / 3 h / 20 °C / 2585.81 Torr / Inert atmosphere 2.2: Inert atmosphere 3.1: sodium hydrogencarbonate / 1,4-dioxane / 19 h / 100 °C / Inert atmosphere
  • 15
  • [ 126534-43-8 ]
  • [ 1185198-25-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium azide / N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere 2.1: hydrogen / 5%-palladium/activated carbon / ethanol / 3 h / 20 °C / 2585.81 Torr / Inert atmosphere 2.2: Inert atmosphere
  • 16
  • [ 126534-43-8 ]
  • (1R)-2-azido-1-(4-fluorophenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With sodium azide In N,N-dimethyl-formamide at 100℃; for 3h; Inert atmosphere; B Step B: (1 RV2-Azido-1-(4-fluoro-Dhenyl)--ethanol. Sodium azide (41.8 g, 642 mmol) was added to a solution consisting of (1R)-2-chloro-1-(4-fluoro-phenyl)- ethanol (37.4 g, 214 mmol) and DMF (214 mL) at rt. The reaction mixture was heated to 100 °C for 3 h, diluted with water (500 mL), and extracted with EtOAc (700 mL). The organic layer was washed with brine (500 mL), and the organic layer dried (MgSO4), filtered, and concentrated, giving the title compound as a yellow liquid, which was used without further purification (39 g, 100%).
  • 17
  • [ 108-05-4 ]
  • [ 61592-48-1 ]
  • [ 134295-34-4 ]
  • [ 126534-42-7 ]
  • [ 126534-43-8 ]
YieldReaction ConditionsOperation in experiment
1: 99 % ee 2: 82 % ee With Amano AK lipase from Pseudomonas fluorescens immobilized on silk friboin-alginate sphere In hexane at 32℃; for 120h; Resolution of racemate; Enzymatic reaction; enantioselective reaction; Kinetic resolution of chlorohydrins (R,S)-1a-h by immobilized lipase from P. fluorescens General procedure: To a 3 mL vial flask were added HPLC grade solvent(1 mL), vinyl acetate (0.100 mL), immobilized lipase Fib-Alg (30mg) and the appropriate chlorohydrins (R,S)-1a-h (40 mg). The reaction mixture was stirred in a mechanic agitation at 300 rpm, at 32 C. The progress of the reactions was followed by removing samples (30 µL of reaction mixture were added to 600 µL of EtOAc) for GC or HPLC analyses, according to the time indicated in Table 4. After the reaction was complete, the immobilized lipase was filtered off. The filtrate was evaporated under reduced pressure and purified by column chromatography on silica gel using hexanes/EtOAc (8:2) as eluent, yielding the enantiomerically enriched (R)-alcohols 1a-h and (S)-acetates 2a-h.
  • 18
  • [ 1737-34-4 ]
  • [ 126534-43-8 ]
YieldReaction ConditionsOperation in experiment
94% With chloro([(S,2S)-(−)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido)(mesitylene)ruthenium (II); formic acid; [2,5-bis(2,6-diisopropylphenyl)cyclopent-3-en-1-yl]{1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methylsulfonamido}gold; water; triethylamine In 1,2-dichloro-ethane at 20℃; for 14h; enantioselective reaction;
86% With formic acid; water; triethylamine In 1,2-dichloro-ethane enantioselective reaction;
Multi-step reaction with 2 steps 1: [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; isopropyl alcohol / water; 2-methyltetrahydrofuran / 16 h / 40 °C 2: [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; isopropyl alcohol; NADPH; magnesium chloride / water; 2-methyltetrahydrofuran / 40 °C / Enzymatic reaction
  • 19
  • [ 7589-27-7 ]
  • [ 126534-43-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triphenylphosphine; trichloroacetamide / dichloromethane / 1 h / 30 °C / Schlenk technique; Inert atmosphere 2.1: escherichia coli (P450PL2-4) cells / aq. phosphate buffer; ethanol / 8 h / 35 °C / pH 8.5 / Green chemistry; Enzymatic reaction 2.2: cell-free extract of HheA10 / 35 °C / pH 8.5 / Enzymatic reaction; Green chemistry
  • 20
  • [ 7589-27-7 ]
  • [ 126534-42-7 ]
  • [ 126534-43-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; trichloroacetamide / dichloromethane / 1 h / 30 °C / Schlenk technique; Inert atmosphere 2: escherichia coli (P450PL2-4) cells / aq. phosphate buffer / 12 h / 35 °C / pH 8.5 / Green chemistry; Enzymatic reaction
  • 21
  • [ 332-43-4 ]
  • [ 126534-43-8 ]
YieldReaction ConditionsOperation in experiment
62 %Chromat. Stage #1: 1-(2-chloroethyl)-4-fluorobenzene With escherichia coli (P450PL2-4) cells In aq. phosphate buffer; ethanol at 35℃; for 8h; Green chemistry; Enzymatic reaction; Stage #2: With cell-free extract of HheA10 In aq. phosphate buffer; ethanol at 35℃; Enzymatic reaction; Green chemistry; enantioselective reaction;
  • 22
  • [ 332-43-4 ]
  • [ 126534-42-7 ]
  • [ 126534-43-8 ]
YieldReaction ConditionsOperation in experiment
87 % ee With escherichia coli (P450PL2-4) cells In aq. phosphate buffer at 35℃; for 12h; Green chemistry; Enzymatic reaction; Overall yield = 81 percentChromat.; enantioselective reaction;
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