4-Nitrophenethyl alcohol

Cat.NO.:A288778 Purity:99%

Product Details of [ 100-27-6 ]

CAS No. :	100-27-6
Formula :	C₈H₉NO₃
M.W :	167.16
SMILES Code :	O=[N+](C1=CC=C(C=C1)CCO)[O-]
MDL No. :	MFCD00010202
InChI Key :	IKMXRUOZUUKSON-UHFFFAOYSA-N
Pubchem ID :	7494

Safety of [ 100-27-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P264-P270-P280-P301+P312+P330-P305+P351+P338-P337+P313-P501

Computational Chemistry of [ 100-27-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	46.2
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.43
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.12
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.13
Log P_o/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.	1.49
Log P_o/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	-0.16
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.0

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.75
Solubility	2.95 mg/ml ; 0.0176 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.1
Solubility	1.33 mg/ml ; 0.00793 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	-2.0
Solubility	1.65 mg/ml ; 0.00989 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.	-6.52 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	2.0 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)	1.5

Application In Synthesis of [ 100-27-6 ]

* 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 [ 100-27-6 ]

[ 100-27-6 ] Synthesis Path-Downstream 1~7

1
[ 103-45-7 ]
[ 100-27-6 ]
[ 15121-84-3 ]

References: [1]Bulletin de la Societe Chimique de France,1929,vol. <4> 45,p. 845,846.
[2]Bulletin de la Societe Chimique de France,1933,vol. <4> 53,p. 330,332.
[3]Helvetica Chimica Acta,1981,vol. 64,p. 1688 – 1703.
[4]Bulletin de la Societe Chimique de France,1931,vol. <4> 49,p. 3,5.

2
[ 60-12-8 ]
[ 100-27-6 ]
[ 15121-84-3 ]
[ 52022-77-2 ]

References: [1]Russian Journal of Organic Chemistry,1994,vol. 30,p. 1556 – 1558.

Zhurnal Organicheskoi Khimii,1994,vol. 30,p. 1478 – 1480.
[2]Russian Journal of Organic Chemistry,1994,vol. 30,p. 1556 – 1558.

Zhurnal Organicheskoi Khimii,1994,vol. 30,p. 1478 – 1480.

3
[ 100-27-6 ]
[ 3056-33-5 ]
[ 917376-69-3 ]

References: [1]Nucleosides, nucleotides and nucleic acids,2005,vol. 24,p. 1665 – 1706.
[2]Synthetic Communications,1999,vol. 29,p. 3003 – 3009.

4
[ 7697-37-2 ]
[ 103-45-7 ]
[ 100-27-6 ]
[ 15121-84-3 ]

References: [1]Bulletin de la Societe Chimique de France,1929,vol. <4> 45,p. 845,846.

5
[ 100-27-6 ]
[ 3056-33-5 ]
[ 218152-30-8 ]

References: [1]Tetrahedron,2001,vol. 57,p. 3373 – 3381.

6
[ 100-27-6 ]
[ 603-35-0 ]
[ 19935-81-0 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; carbon tetrabromide;	EXAMPLE 4 Preparation of 2,2 di (4-nitrophenyl) ethyl bromide To a stirred solution of 2,2 di (4-nitrophenyl) ethanol (0.155 g, 0.54 mmoles) produced by the process of Example 2 in carbon tetrabromide (1.08 moles, 0.362 g) was added triphenyl phosphine (21.08 mmoles, 0.289 g). The originally clear liquid turned yellow immediately, whilst thin layer chromatography indicated that no starting material was present. The solvent was removed under vacuum to give, after flash chromatography (eluent, 1:4 ethyl acetate: petrol ether), the bromide in crystalline form (yield 75%); recrystallisation was from methylene chloride.

References: [1]Patent: US5164515,1992,A .

7
[ 100-27-6 ]
[ 83345-11-3 ]

References: [1]Patent: WO2020/14332,2020,A1 .

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