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Chemical Structure| 4084-38-2 Chemical Structure| 4084-38-2
Chemical Structure| 4084-38-2

*Storage: Keep in dark place,Inert atmosphere,Room temperature.

2,3,5,6-Tetrafluorobenzyl alcohol

CAS No.: 4084-38-2

4.5 *For Research Use Only !

Cat. No.: A102116 Purity: 98%

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Product Details of [ 4084-38-2 ]

CAS No. :4084-38-2
Formula : C7H4F4O
M.W : 180.10
SMILES Code : OCC1=C(F)C(F)=CC(F)=C1F
MDL No. :MFCD00792428
InChI Key :AGWVQASYTKCTCC-UHFFFAOYSA-N
Pubchem ID :2734029

Safety of [ 4084-38-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317-H319
Precautionary Statements:P261-P264-P270-P272-P280-P301+P312+P330-P302+P352+P333+P313+P363-P305+P351+P338+P337+P313-P501

Calculated chemistry of [ 4084-38-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 32.4
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.75
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.44
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.26
Log Po/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.

3.26
Log Po/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

3.38
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.62

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.17
Solubility 1.22 mg/ml ; 0.00679 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.

-1.47
Solubility 6.1 mg/ml ; 0.0339 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very 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

-3.34
Solubility 0.0818 mg/ml ; 0.000454 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

No
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.

-6.38 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

2.0
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)

1.3

Application In Synthesis [ 4084-38-2 ]

* 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 [ 4084-38-2 ]

[ 4084-38-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 773-82-0 ]
  • [ 4084-38-2 ]
  • [ 64248-63-1 ]
  • [ 5216-17-1 ]
  • [ 241154-09-6 ]
  • 2
  • [ 5216-17-1 ]
  • [ 19842-76-3 ]
  • [ 4084-38-2 ]
YieldReaction ConditionsOperation in experiment
100% With acetic acid;aluminum nickel; In 1,4-dioxane; water; Example 19 (Reaction for Conversion from Cyano Group to Aldehyde Group) Using 82 g of dioxane, 21 g of water, 45 g of acetic acid, and 0.5 g of Raney nickel, a reaction was carried out by a method similar to Example 18. The conversion of <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong> was found to be 100% and the yield of 2,3,5,6-tetrafluorobenzaldehyde (based on <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong>) was 47%. The yield of 2,3,5,6-tetrafluorobenzyl alcohol was 2%.
57% With acetic acid;aluminum nickel; In methanol; water; Example 22 (Reaction for Conversion from Cyano Group to Hydroxymethyl Group) 83 g of methanol, 45 g of acetic acid, 21 g of water, 0.5 g of Raney nickel, and 5.0 g of <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong> were added to a 500 cc stainless steel autoclave equipped with a Teflon inner tube in a nitrogen atmosphere. The gas phase was sufficiently replaced with hydrogen gas, then the autoclave was sealed and heated to 60 C. The reaction was carried out for 2 hours, Next, 1.0 g of Raney nickel catalyst was newly added, the gas sufficiently replaced with hydrogen gas, then the pressure raised to 0.5 MPa (gauge pressure). The reaction was carried out at 80 C. for 2 hours again, then the reaction solution was analyzed by gas chromatography, whereupon the conversion of <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong> was found to be 100%, the yield of 2,3,5,6-tetrafluorobenzyl alcohol (based on <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong>) was 57%, and the yield of 2,3,5,6-tetrafluorobenzaldehyde was 2%.
44% With sulfuric acid;aluminum nickel; In methanol; Example 16 (Reaction for Conversion from Cyano Group to Aldehyde Group) Using 158 g of methanol, 5.7 g of concentrated sulfuric acid, and 5.0 g of Raney nickel, a reaction was carried out by a method similar to Example 15. When the reaction was carried out at 25 C. for 4 hours, the conversion of <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong> was found to be 80%, the yield of 2,3,5,6-tetrafluorobenzaldehyde (based on <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong>) was 44%, and the yield of 2,3,5,6-tetrafluorobenzyl alcohol was 1%.
33% With sulfuric acid; acetic acid;palladium/activated carbon; Example 15 (Reaction for Conversion from Cyano Group to Aldehyde Group) 150 g of acetic acid, 50 g of 3N aqueous sulfuric acid solution, 0.875 g of 2% palladium/activated carbon, and 8.75 g of <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong> were added to a 500 cc glass three-necked flask with a reflux condenser in a nitrogen atmosphere. The gas phase was sufficiently replaced with hydrogen gas, then a hydrogen balloon was attached to the top portion of the reflux condenser and the reaction was carried out at 80 C. for 8 hours. The reaction solution was analyzed by gas chromatography, whereupon the conversion of <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong> was found to be 59%, the yield of 2,3,5,6-tetrafluorobenzaldehyde (based on <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong>) was 33%, and the yield of 2,3,5,6-tetrafluorobenzyl alcohol was 7%.

  • 3
  • [ 5216-17-1 ]
  • [ 598-54-9 ]
  • [ 19842-76-3 ]
  • [ 4084-38-2 ]
YieldReaction ConditionsOperation in experiment
80% With acetic acid;aluminum nickel; In methanol; water; Example 14 (Reaction for Conversion from Cyano Group to Aldehyde Group) 0.5 g of Raney nickel, 0.31 g of a copper acetate 10 hydrate, and 50 ml of water were added to a 500 cc glass three-necked flask with a reflux condenser in a nitrogen atmosphere. The resulting mixture was stirred at 25 C. for 2 hours, then 50 ml of water and methanol were successively added and decanting performed to wash the catalyst. Further, 80 g of methanol, 100 g of acetic acid, and 5 g of water as the solvent and 8.75 g of <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong> were newly added. The gas phase was sufficiently replaced with hydrogen gas, then a hydrogen balloon was attached to the top portion of the reflux condenser and the reaction carried out at 25 C. for 6 hours. The reaction solution was analyzed by gas chromatography, whereupon the conversion of <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong> was found to be 100%, the yield of 2,3,5,6-tetrafluorobenzaldehyde (based on <strong>[5216-17-1]2,3,5,6-tetrafluorobenzonitrile</strong>) was 80%, and the yield of 2,3,5,6-tetrafluorobenzyl alcohol was 2%.
 

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Technical Information

• Alkyl Halide Occurrence • Appel Reaction • Arndt-Eistert Homologation • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hunsdiecker-Borodin Reaction • Hydride Reductions • Jones Oxidation • Lawesson's Reagent • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Preparation of Carboxylic Acids • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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