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Chemical Structure| 1475-11-2 Chemical Structure| 1475-11-2
Chemical Structure| 1475-11-2

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1-(3,4-Dichlorophenyl)ethanol

CAS No.: 1475-11-2

4.5 *For Research Use Only !

Cat. No.: A349421 Purity: 95%

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Product Details of [ 1475-11-2 ]

CAS No. :1475-11-2
Formula : C8H8Cl2O
M.W : 191.06
SMILES Code : CC(O)C1=CC=C(Cl)C(Cl)=C1
MDL No. :MFCD00021865
Boiling Point : No data available
InChI Key :VZTGSONNNMGQNQ-UHFFFAOYSA-N
Pubchem ID :97899

Safety of [ 1475-11-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H315-H318-H335-H410
Precautionary Statements:P261-P273-P280-P305+P351+P338
Class:9
UN#:3082
Packing Group:

Calculated chemistry of [ 1475-11-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 47.4
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.

2.29
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

3.32
Log Po/w (WLOGP)?

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

2.72
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.

3.03
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

3.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.89

Water Solubility

Log S (ESOL):?

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

-3.45
Solubility 0.0672 mg/ml ; 0.000352 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.

-3.42
Solubility 0.0724 mg/ml ; 0.000379 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

-3.49
Solubility 0.0614 mg/ml ; 0.000321 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.

-5.11 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

0.0 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)

1.8

Application In Synthesis [ 1475-11-2 ]

* 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 [ 1475-11-2 ]

[ 1475-11-2 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 1475-11-2 ]
  • [ 2642-63-9 ]
YieldReaction ConditionsOperation in experiment
With manganese(IV) oxide; silica gel; In acetonitrile; at 70℃; for 8h;Molecular sieve; General procedure: The above secondary alcohol was dissolved in acetonitrile (30mL). Molecular sieve (1.5g), silica gel (1.5g) and activated MnO2 (3.5g, 40mmol) were added, and the mixture was stirred at 70C for 8h. upon completion of the oxidation, the resulting suspension was filtered through diatomite, and the filtrate was concentrated by rotary evaporation. Purification of the residue by column chromatography (petroleum ethrt/EtOAc, 15:1) afforded ketone 13.
  • 2
  • [ 917-64-6 ]
  • [ 6287-38-3 ]
  • [ 1475-11-2 ]
  • 3
  • [ 555-31-7 ]
  • [ 2642-63-9 ]
  • [ 1475-11-2 ]
  • 4
  • [ 1475-11-2 ]
  • [ 2039-83-0 ]
  • 5
  • [ 2642-63-9 ]
  • [ 1475-11-2 ]
YieldReaction ConditionsOperation in experiment
97% With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol; at 82℃; for 6h;Inert atmosphere; Green chemistry; The 3, 4 - dichloro ethanone (189 mg, 1.0 mmol), cat. [Ir] (1.1 mg, 0 . 002 mmol, 0.2 muM %) and isopropyl alcohol (5 ml) are added to the 25 ml Kjeldahl tube, N2Protection, 82 C reaction 6 h. Cooling to room temperature, rotary evaporation to remove the solvent, then through the column chromatography (developing solvent: petroleum ether/ethyl acetate) to obtain the pure target compound, yield: 97%
94% With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); hydrogen; In tert-Amyl alcohol; at 30℃; under 760.051 Torr; for 12h;Green chemistry; General procedure: To an oven-dried 5 mL round-bottom flask were added ketone (1 mmol), cat. 7 (2.7 mg, 0.5 mol %) and tert-amyl alcohol (1 mL). Next, vacuum was applied to the flask followed by filling with H2 gas and keeping the flask attached to a balloon filled with H2 gas. The mixture was heated at 30 C for 12 h. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. The alcohols were isolated and purified by filtering a hexanes/ethyl acetate (5:1) solution of the crude product through a pad of silica gel, and then removing the solvent under reduced pressure. The conversion and purity of the alcohol products was assessed using NMR spectroscopy.
80% With sodium tetrahydroborate; ethanol; at 20℃;Cooling with ice; 2.2 mmol NaBH4 was added to 2.1 mmol of 8a in dry ethanol (10 mL) stirred in an ice bath.The suspension was further stirred at room temperature overnight. After the reaction was completed, it was quenched by the addition of 1.0 N HCl, and the remaining ethanol was evaporated under reduced pressure. The product was extracted with diethyl ether (25 mL x 2),washed with sodium bicarbonate (15 mL), and water (10 mL), dried over MgSO4, and evaporated under reduced pressure. Silica gel column chromatography (hex ane:ethyl acetate4:1) was performed to give the corresponding rac-8b. 9a-11a and 13a (2.21 mmol~2.66 mmol) were also reduced similarly. The 1H-NMR spectra of alcohols 8b [1], 9b-11b [2], and 13b [3] were in agreement with those reported in the literature. 1.2.1 1-(3?,4?-Dichlorophenyl)ethanol, rac-8b. 0.42 g (2.21 mmol) of 8a was converted to 0.34 g of rac-8b (1.77 mmol, 80%, colorless oil). 1H-NMR (400 MHz, CDCl3, 25C, TMS): delta=7.47-7.48 (m, 1H), 7.41(d, J=8.4 Hz, 1H), 7.20 (dd, J=8.4 Hz, 2.0Hz, 1H), 4.85-4.90 (m, 1H), 1.85 (brd,J=3.6 Hz, 1H), 1.48 (d, J=6.4 Hz, 3H).
With sodium tetrahydroborate; In methanol; at 0 - 20℃; To a stirred solution of 3,4-dichloroacetophenone (4 g, 21.15 mmol, Aldrich) in dry MeOH (80 mL), sodium borohydride (0.96 g, 25.39 mmol, spectrochem) was added portionwise at 0 C. The reaction mixture was stirred at rt overnight. It was cooled to 0 C and quenched using ice water (10 mL). Solvents were removed under reduced pressure and resulting residue was dissolved in DCM (50 mL). The organic layer was washed with water (25 mL), brine (20 mL), dried over Na2SO4 and concentrated. The crude product was used for next step without further purification. Yield: 95% (3.8 g, colorless liquid). 1H NMR (400 MHz, DMSO-d6): delta 7.57-7.55 (m, 2H), 7.33 (d, J = 1.9 Hz, 1H), 5.38 (d, J = 4.4 Hz, 1H), 4.76-4.70 (m, 1H), 1.30 (d, J = 6.4 Hz, 3H).
With methanol; sodium tetrahydroborate; at 0 - 20℃; General procedure: Ten mmol of NaBH4 was added to a cooled (0C) solution of 2.5 mmol of each specific substrate(1a-1f, 1m and 1n) in 50 mL of methanol. After stirring for 10 min, the mixture was warmed to room temperature and stirred for another 3-4 h to complete the reduction. After quenching with 2 M HCl topH 7.0, the mixture was extracted with EtOAc (50 mL 3). The organic phases were washed withbrine, dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by flashchromatography on silica gel (eluent: EtOAc/PE 1:20) to give the racemic alcohol 2a-2f, 2m and 2n(see Supplementary Materials for NMR spectroscopic data).

  • 6
  • [ 52909-94-1 ]
  • [ 60-29-7 ]
  • lithium borate [ No CAS ]
  • [ 1475-11-2 ]
  • [ 35364-79-5 ]
  • 7
  • [ 52909-94-1 ]
  • [ 64-17-5 ]
  • platinum [ No CAS ]
  • [ 1475-11-2 ]
  • [ 35364-79-5 ]
  • 9
  • (+-)-<3,4-dichloro-phenyl>-oxirane [ No CAS ]
  • [ 1475-11-2 ]
  • 11
  • [ 1475-11-2 ]
  • (1S,2R,3R,5R,6S)-2-amino-3-[1-(3,4-dichlorophenyl)ethoxy]bicyclo[3.1.0]hexane-2,6-dicarboxylic acid [ No CAS ]
  • 12
  • [ 1475-11-2 ]
  • (1S,2R,3R,5R,6S)-2-amino-3-[1-(3,4-dichlorophenyl)ethoxy]bicyclo[3.1.0]hexane-2,6-dicarboxylic acid [ No CAS ]
  • 13
  • [ 1475-11-2 ]
  • (1S,2R,3R,5R,6S)-2-Azido-3-[1-(3,4-dichloro-phenyl)-ethoxy]-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester [ No CAS ]
  • 14
  • [ 1475-11-2 ]
  • (1S,2R,3R,5R,6S)-2-Amino-3-[1-(3,4-dichloro-phenyl)-ethoxy]-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester [ No CAS ]
  • 15
  • [ 1475-11-2 ]
  • (1S,2R,3R,5R,6S)-2-Azido-3-[1-(3,4-dichloro-phenyl)-ethoxy]-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester [ No CAS ]
  • 16
  • [ 1475-11-2 ]
  • (1S,2R,3R,5R,6S)-2-Amino-3-[1-(3,4-dichloro-phenyl)-ethoxy]-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester [ No CAS ]
  • 17
  • [ 1475-11-2 ]
  • (1R,2R,3R,5R,6R)-2-amino-3-(1-(3,4-dichlorophenyl)ethoxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid [ No CAS ]
  • 18
  • [ 1475-11-2 ]
  • (1R,2R,3R,5R,6R)-2-Amino-3-[1-(3,4-dichloro-phenyl)-ethoxy]-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester [ No CAS ]
  • 19
  • [ 1475-11-2 ]
  • (1R,2R,3R,5R,6R)-2-Azido-3-[1-(3,4-dichloro-phenyl)-ethoxy]-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester [ No CAS ]
  • 20
  • [ 1475-11-2 ]
  • [ 52909-94-1 ]
  • 21
  • [ 1475-11-2 ]
  • 1-(3,4-Dichloro-phenyl)-2-((1R,3S,5S)-3-phenyl-8-aza-bicyclo[3.2.1]oct-8-yl)-ethanol [ No CAS ]
  • 23
  • [ 110-89-4 ]
  • [ 1475-11-2 ]
  • [ 459451-08-2 ]
YieldReaction ConditionsOperation in experiment
Example 169 5-(2-Piperidinyl-ethyl)-2-methyl-1H-indole-3-carboxylic 1-(3,4-dichlorophenyl)-ethyl Ester The procedure for Example 65 was followed, substituting (3,4-dichlorophenyl)-ethan-1-ol for (S)-phenylethanol, and substituting piperidine for diethylamine. ESI+MS m/z 459 (M+1).
  • 24
  • [ 1897-52-5 ]
  • [ 1475-11-2 ]
  • [ 872181-29-8 ]
YieldReaction ConditionsOperation in experiment
Example 78; 5-[1-(3,4-Dichlorophenyl)-ethoxy]-quinazoline-2,4-diamine; [00244] Step 1; To a cold (ice water) suspension of sodium hydride (316 mg; 7.9 mmol) in anhydrous DMF (10 mL) is added a solution of 1-(3,4-dichlorophenyl)- ethanol (1.40 g; 7.3 mmol) in anhydrous DMF (5 mL) over 30 minutes. After allowing to room temperature over 30 minutes, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (1.0 g; 7.2 mmol) in anhydrous DMF (15 mL), and allowed to room temperature over 2 hours. The reaction mixture is poured into ice water with vigorous stirring and extracted with ethyl acetate. The organics are separated and dried over magnesium sulfate. The solvent is removed and the resulting oil is dried under vacuum at 30 C overnight to give 1.93 gm of 2-[1- (3,4-dichlorophenyl) -ethoxy]-6-fluorobenzonitrile.
 

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