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Chemical Structure| 122-37-2 Chemical Structure| 122-37-2

Structure of 4-Hydroxydiphenylamine
CAS No.: 122-37-2

Chemical Structure| 122-37-2

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Product Details of [ 122-37-2 ]

CAS No. :122-37-2
Formula : C12H11NO
M.W : 185.22
SMILES Code : OC1=CC=C(NC2=CC=CC=C2)C=C1
MDL No. :MFCD00020142
InChI Key :JTTMYKSFKOOQLP-UHFFFAOYSA-N
Pubchem ID :31208

Safety of [ 122-37-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H319
Precautionary Statements:P305+P351+P338

Computational Chemistry of [ 122-37-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 1.0
Num. H-bond donors 2.0
Molar Refractivity 58.01
TPSA ?

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

32.26 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.88
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

2.82
Log Po/w (WLOGP)?

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

3.14
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.

2.68
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

2.26
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.55

Water Solubility

Log S (ESOL):?

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

-3.27
Solubility 0.1 mg/ml ; 0.00054 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.

-3.15
Solubility 0.13 mg/ml ; 0.0007 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

-4.39
Solubility 0.00753 mg/ml ; 0.0000406 mol/l
Class?

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

Moderately 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

Yes
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.

-5.43 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)

1.57

Application In Synthesis of [ 122-37-2 ]

* 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 [ 122-37-2 ]

[ 122-37-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 84-67-3 ]
  • [ 122-37-2 ]
  • [ 1013336-06-5 ]
YieldReaction ConditionsOperation in experiment
88% Bis(4-diphenylamino)-<strong>[84-67-3]2,2'-dimethyl-4,4'-diaminobiphenyl</strong> (hereinafter abbreviated as BDDMD) represented by the formula (34) was prepared from p-hydroxydiphenylamine and 4,4'-diaminodiphenyl ether according to the following procedure (white solid, yield of 88percent). [Show Image] In 1 liter of toluene, 10.6145 g (0.05 mols) of <strong>[84-67-3]2,2'-dimethylbenzidine</strong> was dissolved. To obtain a dehydrating condensation agent, 153.144 g (0.45 mols) of titanium tetra-n-butoxide and 67.5765 g (0.45 mols) of p-tolyl acetate were evaporated on a water bath of 60°C for 60 minutes to completely distill off the resulting butyl acetate. This agent was added to the solution. While keeping the reaction solution at 110°C, 22.2264 g (0.12 mols) of p-hydroxydiphenylamine was added to the solution under nitrogen atmosphere, followed by reaction at the temperature for 48 hours under nitrogen atmosphere. After completion of the reaction, the reaction solution, cooled down to room temperature, was filtered and the resulting filtrate was washed with toluene and then with diethyl ether and dried to obtain white powder. The thus obtained crude product of BDDMD was purified according to the treatment with active carbon and recrystallization treatment as in Comparative Example 1. The recovery rate was at 98percent
  • 2
  • [ 10016-52-1 ]
  • [ 122-37-2 ]
  • C36H26N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.8 g With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In toluene; at 100℃; for 17h; To a one-necked flask were added A-1-1 (2.5 g), B8 (3.6 g)And sodium tert-butoxide (4.4 g) was added thereto.Fill the flask, add di-gassed toluene (40 mL), and heat to 100 oC. Pd [P (t-Bu) 3] 2 (200 mg), PdAnd the mixture was stirred at the same temperature for 17 hours.Diluted with DCM (100 mL) and filtered through SiO2.The filtered solution was depressurized to remove the solvent. The solvent was dissolved again in THF to obtain EA, which was then recrystallized to obtain A-8-1 (1.8 g).
 

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