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Chemical Structure| 2314-36-5 Chemical Structure| 2314-36-5

Structure of 2314-36-5

Chemical Structure| 2314-36-5

3,5-Dichloro-4-hydroxybenzaldehyde

CAS No.: 2314-36-5

4.5 *For Research Use Only !

Cat. No.: A204560 Purity: 97%

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Product Details of [ 2314-36-5 ]

CAS No. :2314-36-5
Formula : C7H4Cl2O2
M.W : 191.01
SMILES Code : O=CC1=CC(Cl)=C(O)C(Cl)=C1
MDL No. :MFCD00017605
InChI Key :LIYGCLJYTHRBQV-UHFFFAOYSA-N
Pubchem ID :16839

Safety of [ 2314-36-5 ]

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

Computational Chemistry of [ 2314-36-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 43.87
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.48
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

2.52
Log Po/w (WLOGP)?

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

2.51
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.

1.97
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

2.79
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.25

Water Solubility

Log S (ESOL):?

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

-2.95
Solubility 0.215 mg/ml ; 0.00112 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.

-2.95
Solubility 0.215 mg/ml ; 0.00112 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

-3.01
Solubility 0.188 mg/ml ; 0.000986 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.

-5.68 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

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)

1.19

Application In Synthesis of [ 2314-36-5 ]

* 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.

  • Downstream synthetic route of [ 2314-36-5 ]

[ 2314-36-5 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 103-82-2 ]
  • [ 2314-36-5 ]
  • [ 101095-25-4 ]
  • 3
  • [ 141-82-2 ]
  • [ 2314-36-5 ]
  • [ 73747-62-3 ]
  • 4
  • [ 2314-36-5 ]
  • [ 14399-63-4 ]
  • 2-cyclohex-1-enyl-3-(3,5-dichloro-4-hydroxy-phenyl)-acrylic acid [ No CAS ]
  • 5
  • [ 2314-36-5 ]
  • [ 13005-36-2 ]
  • [ 5325-40-6 ]
  • 6
  • [ 123-08-0 ]
  • [ 2314-36-5 ]
YieldReaction ConditionsOperation in experiment
55% With sulfuryl dichloride; In chloroform;Inert atmosphere; Reflux; Compound R53 (4.9 g, 40 mmol) was dissolved in 80 ml of dry chloroform, followed by argon gasProtected, heated to reflux, slowly added dropwise a solution of 20 ml of sulfonyl chloride (6.4 ml, 80 mmol) in chloroform, and then refluxed overnight. The reaction solution was spin-dried and purified on a silica gel column. Yield 4.2g (55percent).
  • 7
  • [ 2314-36-5 ]
  • [ 79-19-6 ]
  • [ 112367-64-3 ]
  • 8
  • [ 2314-36-5 ]
  • [ 103-81-1 ]
  • [ 102590-58-9 ]
  • 9
  • [ 2314-36-5 ]
  • [ 108-24-7 ]
  • [ 543-24-8 ]
  • [ 14886-17-0 ]
  • 10
  • [ 300-87-8 ]
  • [ 2314-36-5 ]
  • [ 113465-84-2 ]
  • 11
  • [ 79-46-9 ]
  • [ 22002-17-1 ]
  • [ 2314-36-5 ]
  • [ 85628-45-1 ]
  • 12
  • [ 79-46-9 ]
  • [ 56733-60-9 ]
  • [ 87-65-0 ]
  • [ 2314-36-5 ]
  • [ 85628-45-1 ]
  • 13
  • [ 22002-17-1 ]
  • [ 2314-36-5 ]
YieldReaction ConditionsOperation in experiment
22% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2CI2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77g, 22percent). LC-MS: tR = 0.82 min.
22% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2Cl2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77 g, 22percent). LC-MS: tR=0.82 min.
22% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CHaCk, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77g, 22percent). LC-MS: tR = 0.82 min.
22% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2Cl2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77 g, 22percent). LC-MS: tR = 0.82 min.

  • 14
  • [ 2314-36-5 ]
  • [ 98033-85-3 ]
  • [ 124811-92-3 ]
  • 15
  • [ 2314-36-5 ]
  • [ 6921-34-2 ]
  • [ 73049-09-9 ]
  • 16
  • [ 2314-36-5 ]
  • [ 107-05-1 ]
  • [ 27164-07-4 ]
  • 17
  • [ 2314-36-5 ]
  • [ 22002-17-1 ]
  • 18
  • [ 3970-21-6 ]
  • [ 2314-36-5 ]
  • [ 124956-03-2 ]
  • 19
  • [ 2314-36-5 ]
  • [ 108-94-1 ]
  • 2,6-Bis-[1-(3,5-dichloro-4-hydroxy-phenyl)-meth-(E)-ylidene]-cyclohexanone [ No CAS ]
  • 20
  • [ 2314-36-5 ]
  • [ 120-92-3 ]
  • 2,5-Bis-[1-(3,5-dichloro-4-hydroxy-phenyl)-meth-(E)-ylidene]-cyclopentanone [ No CAS ]
  • 21
  • [ 2314-36-5 ]
  • [ 67-64-1 ]
  • 1,5-bis(4-hydroxy-3,5-dichlorophenyl)-1,4-pentadien-3-one [ No CAS ]
  • 22
  • [ 60-35-5 ]
  • [ 201230-82-2 ]
  • [ 2314-36-5 ]
  • [ 212067-18-0 ]
  • 23
  • [ 60-35-5 ]
  • [ 201230-82-2 ]
  • [ 2314-36-5 ]
  • (R)-N-acetyl-α-(3,5-dichloro-4-hydroxyphenyl)glycine [ No CAS ]
  • 24
  • [ 36517-91-6 ]
  • [ 2314-36-5 ]
  • 2-(3,5-Dichloro-4-hydroxy-benzylidene)-5,6-dimethoxy-indan-1,3-dione [ No CAS ]
  • 25
  • [ 2314-36-5 ]
  • 5-Amino-indan-1,3-dione [ No CAS ]
  • 5-Amino-2-[1-(3,5-dichloro-4-hydroxy-phenyl)-meth-(E)-ylidene]-indan-1,3-dione [ No CAS ]
  • 26
  • [ 2314-36-5 ]
  • 2-[1-(3,4-Dihydroxy-phenyl)-meth-(Z)-ylidene]-4-nitro-indan-1,3-dione [ No CAS ]
  • 2-[1-(3,5-Dichloro-4-hydroxy-phenyl)-meth-(Z)-ylidene]-4-nitro-indan-1,3-dione [ No CAS ]
  • 27
  • [ 2432-12-4 ]
  • [ 124-41-4 ]
  • [ 2314-36-5 ]
  • [ 79817-03-1 ]
  • 2-chloro-6-(2,6-dichloro-4-methyl-phenoxy)-4-methoxy-4-methyl-cyclohexa-2,5-dienone [ No CAS ]
  • 2-chloro-6-(2,6-dichloro-4-methoxymethyl-phenoxy)-4-methoxy-4-methyl-cyclohexa-2,5-dienone [ No CAS ]
  • 28
  • [ 2314-36-5 ]
  • [ 156-87-6 ]
  • 2,6-Dichloro-4-[(E)-3-hydroxy-propylimino]-methyl}-phenol [ No CAS ]
  • 30
  • [ 2314-36-5 ]
  • [ 7722-84-1 ]
  • KOH-solution [ No CAS ]
  • [ 20103-10-0 ]
YieldReaction ConditionsOperation in experiment
90% With hexamethylenetetramine;Reflux; General procedure: A solution of the selected phenol (10 mmol) and hexamethylenetetramine (11 mmol, 1.550 g) in trifluoroacetic acid (10 mL) was stirred and heated at reflux overnight. After cooling to room temperature, the crude product mixture was evaporated under reduced pressure and the yellow residue obtained was poured into distilled water and crushed ice. The cream-colored solid that precipitated was filtered under reduced pressure, washed with distilled water and dried at room temperature under vacuum, yielding the desired compound as a white solid. See, e.g., (Scheme 1, Figure 2). Yield: 60percent, 940 mg;
quaternary ammonium compounds, such asN-alkyl-N,N-dimethylbenzyl ammonium chloride and...cetylpyridinium chloridediguanidinepolybiguanide1,2-dibromo-2,4-dicyanobutane3,5-dichloro4-hydroxybenzaldehydeethylene glycol hemiformaldichlorophen2,2-dibromo-3-nitrilopropionic acid amide...
Stage A 3,5-dichloro-4-hydroxy-benzaldehyde 15 g of hydroxy-4-benzaldehyde in 75 ml of thionyl chloride was stirred at reflux for 36 hours and then the reaction medium was evaporated under reduced pressure to obtain the expected crude product which was crystallized from an acetone/n-pentane mixture to obtain 20 g of an 85/15 mixture of dichlorinated/monochlorinated product. Crystallization from a cyclohexane/acetone mixture (4/1) allowed the pure dichlorinated product to be obtained with a Rf=0.15 (dichloromethane/methanol 99/1). IR (CHCl3)
Quaternary ammonium compounds such asN-alkyl-N,N-dimethylbenzylammonium chloride anddi-n-decyldimethylammonium chlorideCetylpyridinium chlorideDiguanidine1,2-Dibromo-2,4-dicyanobutane3,5-Dichloro-4-hydroxybenzaldehydeEthylene glycol hemiformal

 

Historical Records

Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Halogenation of Phenols • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Reimer-Tiemann Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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