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[ CAS No. 771-61-9 ] {[proInfo.proName]}

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Chemical Structure| 771-61-9
Chemical Structure| 771-61-9
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Halynne R. Lamontagne ; Mélanie Cyr ; Mário C. Vebber , et al. DOI:

Abstract: Organic thin-film transistors (OTFTs) are an emerging platform for rapid, point-of-source detection and speciation of Δ9 -tetrahydrocannabinol (THC) and cannabidiol (CBD). (F5PhO)2-F16-SiPc semiconductor was implemented into high performance, air-stable n-type bottom gate, bottom contact OTFTs, however, the resulting device performance changes in response to THC and CBD were negligible. We explored the orientation of the corresponding thin films by synchrotron-based grazing incidence wide-angle X-ray scattering (GIWAXS) and angle-dependent near-edge X-ray absorption fine structure (NEXAFS), as well as polarized Raman microscopy. These techniques demonstrate for the first time that (F5PhO)2-F16-SiPc molecules are at a 45–48° orientation to the substrate; comparable to other reported R2-SiPcs. This orientation did not change upon exposure to THC and CBD, which has previously been reported for phthalocyanine-based OTFT cannabinoid sensors. The presence of two bulky axial groups, along with the absence of hydrogens in the molecule and the low reactivity of the silicon atom likely causes the lack of interaction with the cannabinoids. While (F5PhO)2-F16-SiPc may be a successfully air-stable n-type semiconductor for OTFTs, the structural changes performed to make it air stable over traditional nonfluorinated silicon MPcs, are likely responsible for its lack of response to cannabinoid exposure.

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Product Details of [ 771-61-9 ]

CAS No. :771-61-9 MDL No. :MFCD00002156
Formula : C6HF5O Boiling Point : -
Linear Structure Formula :- InChI Key :XBNGYFFABRKICK-UHFFFAOYSA-N
M.W : 184.06 Pubchem ID :13041
Synonyms :
Chemical Name :2,3,4,5,6-Pentafluorophenol

Calculated chemistry of [ 771-61-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 28.26
TPSA : 20.23 ?2

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) : -5.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 3.23
Log Po/w (WLOGP) : 4.19
Log Po/w (MLOGP) : 3.64
Log Po/w (SILICOS-IT) : 3.53
Consensus Log Po/w : 3.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.39
Solubility : 0.0757 mg/ml ; 0.000411 mol/l
Class : Soluble
Log S (Ali) : -3.33
Solubility : 0.0865 mg/ml ; 0.00047 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.22
Solubility : 0.111 mg/ml ; 0.000604 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 771-61-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 771-61-9 ]

* 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 [ 771-61-9 ]

[ 771-61-9 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 771-61-9 ]
  • [ 34622-39-4 ]
  • [ 78664-72-9 ]
  • 2
  • [ 6624-49-3 ]
  • [ 771-61-9 ]
  • [ 197895-16-2 ]
  • 3
  • [ 771-61-9 ]
  • [ 32926-43-5 ]
  • [ 396728-17-9 ]
  • 4
  • [ 771-61-9 ]
  • [ 35737-10-1 ]
  • [ 149303-38-8 ]
  • 5
  • [ 771-61-9 ]
  • [ 51146-57-7 ]
  • pentafluorophenyl (R)-2-(4-isobutylphenyl)propionate [ No CAS ]
  • 6
  • [ 771-61-9 ]
  • [ 475-11-6 ]
  • C12H10F5NO2 [ No CAS ]
  • 7
  • [ 771-61-9 ]
  • [ 2456-81-7 ]
  • 4-(pyrrolidino)pyridinium pentafluorophenate pentafluorophenol [ No CAS ]
  • 8
  • [ 14154-42-8 ]
  • [ 771-61-9 ]
  • pentauorophenoxy aluminum phthalocyanine [ No CAS ]
  • 9
  • [ 771-61-9 ]
  • [ 1835-65-0 ]
  • 5,6-bis(pentafluorophenoxy)-4,7-difluoro-2H-isoindole [ No CAS ]
  • 10
  • [ 771-61-9 ]
  • [ 1835-65-0 ]
  • 4,5-bis(pentafluorophenoxy)-3,6-difluorophthalonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.83% With potassium fluoride; at 20℃; for 48h;Cooling with ice; First raw material 4,5-bis (pentafluorophenyl) -3,6-difluoro-phthalonitrile were prepared as follows: A 200ml reaction vessel equipped with a dropping funnel and a thermometer <strong>[1835-65-0]tetrafluorophthalonitrile</strong> 20.1 g ( 100.45mmol), potassium fluoride 13.99g (240.79mmol), was added to the methyl isobutyl ketone 130ml.After cooling with an ice-bath, conducted from the dropping funnel, was added slowly a solution of pentafluorophenol 37.0g (201.02mmol) of methyl isobutyl ketone 70 ml, then the reaction was stirred for 2 days at room temperature It was.Except inorganic salt and the reaction solution was filtered, washed with water using a separatory funnel, was dehydrated with anhydrous sodium sulfate, the reaction solution was concentrated in an evaporator.The concentrate, by re-precipitation purification with toluene / hexane solvent, 4,5-bis (pentafluorophenyl) -3,6-difluoro phthalonitrile, 70.83percent yield (37.4g, 70.81mmol obtained in).
  • 11
  • [ 771-61-9 ]
  • [ 13122-90-2 ]
  • C29H27F5N2O5 [ No CAS ]
  • 12
  • [ 771-61-9 ]
  • [ 14019-62-6 ]
  • [ 770-12-7 ]
  • C17H15F5NO5P [ No CAS ]
  • 13
  • [ 532391-89-2 ]
  • [ 771-61-9 ]
  • pentafluorophenyl 4-methyl-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With dicyclohexyl-carbodiimide; In 1,4-dioxane; for 17.0h; Dicyclohexylcarbodiimide (807 mg, 3.91 mmol) was added to a stirred suspension of4-methyl-3,4-dihydro-2H-1 ,4-benzoxazine-7-carbcxylic acid (CAS 532391-89-2) (685 mg,3.55 mmcl) and pentafluorophenol (653 mg, 3.55 mmcl) in 1,4-dioxane (15 mL). Stirring was continued for 17 h by which time a colorless precipitate had formed. The mixture was filtered and evaporated; the residue was dissolved in CH2CI2 (20 mL) and evaporated to give the crude ester pentafluorophenyl 4-methyl-3,4-dihydro-2H-1 ,4-benzoxazine-7-carboxylate(1.4g, 3.90 mmcl, 100%) as a yellow oily solid which was used in the next step without purification. 1Pr2NEt (523 pL, 388 mg, 3 mmol) was added to a stirred mixture of 1-(3- brcmophenyl)ethanone (199 mg, 1 mmcl) and MgBr2Et2O (646 mg, 2.5 mmcl) in CH2CI2 (10 mL). The resulting suspension was stirred for 15 mm, then pentafluorophenyl 4-methyl-3,4- dihydro-2H-1 ,4-benzcxazine-7-carboxylate (431 mg, 1 .2 mmcl) in CH2CI2 (2 mL) was addeddropwise. After 24 h 1-(3-brcmophenyl)ethanone (199 mg, 1 mmcl), MgBr2Et2O (646 mg,2.5 mmcl), and 1Pr2NEt (523 pL, 388 mg, 3 mmcl) were added and the stirring was continued for further 24 h. 1 N phosphate buffer pH 6 (20 mL) was added, stirred for 10 mm, the organic phase was separated, the aqueous phase was extracted with CHCI3 (10 mL), the combined organic extract was washed with saturated NaHCO3 solution, brine, dried over Na2SO4 andconcentrated in vacuo. The residue was purified by flash chromatography on silica gel (n-hexane/chlcrofcrm =1:1, Rf 0.15) to afford 362 mg of crude product as yellow foam which was used in the next step without further purification. To a solution of crude 1-(3- brcmcphenyl)-3-(4-methyl-3,4-dihydrc-2H- 1 ,4-benzcxazin-7-yl )prcpane-1 ,3-dicne (362 mg) in EtDH (10 mL) hydrazine monohydrate (194 pL, 200 mg, 4 mmcl) was added. The reactionmixture was stirred at 78 00 for 15 h, cooled down to room temperature, the solvent and excess of hydrazine monchydrate were removed on the rotary evaporator. Tcluene (20 mL) was added and the mixture was concentrated to dryness. The crude product (380 mg) waspurified by flash chromatography on silica gel (chloroform/methanol =100:1, Rf 0.26) to afford the product (30 mg, 0.08 mmol, 8% over three steps) as a white solid.
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