3-Amino-2-bromophenol

Cat.NO.:A729251 Purity:95%

Product Details of [ 100367-36-0 ]

CAS No. :	100367-36-0
Formula :	C₆H₆BrNO
M.W :	188.02
SMILES Code :	OC1=CC=CC(N)=C1Br
MDL No. :	MFCD11846453
InChI Key :	ZSNIVQDQECTJAJ-UHFFFAOYSA-N
Pubchem ID :	459240

Safety of [ 100367-36-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 100367-36-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	2.0
Molar Refractivity	40.57
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.47
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	1.58
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.74
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.	1.58
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	1.34
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.54

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.49
Solubility	0.602 mg/ml ; 0.0032 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.	-2.16
Solubility	1.29 mg/ml ; 0.00689 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	-2.32
Solubility	0.906 mg/ml ; 0.00482 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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.33 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)	1.14

Application In Synthesis of [ 100367-36-0 ]

* 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.

Upstream synthesis route of [ 100367-36-0 ]
Downstream synthetic route of [ 100367-36-0 ]

[ 100367-36-0 ] Synthesis Path-Upstream 1~5

1
[ 101935-40-4 ]
[ 100367-36-0 ]

Yield	Reaction Conditions	Operation in experiment
43.9%	With iron; acetic acid In ethanolReflux	[00408] 2-Bromo-3-nitro-phenol (3.35 g, 15.4 mmol), acetic acid (35 mL) and iron powder(4.5 g, 77.2 mmol) were stirred in ethanol (50 mL) under reflux overnight. The mixture was diluted with 1 00m1 of water and neutralised with potassium carbonate before extraction with DCM. The organics were dried with sodium sulfate and concentrated in vacuo to leave the crude product as a brown oil. This was dry-packed on to silica and purified by columnchromatography using a 0-50percent gradient of ethyl acetate in isohexane. The resulting fragments were concentrated in vacuo to give 3-amino-2-bromo-phenol (1 .27 g, 6.75 mmol, 43.9percent) as a pale yellow solid.[00409] 1H NMR (DMSO-d6): O 7.02 (t, J = 8.0 Hz, 1H), 6.45 (dd, J= 1.6 and 8.0 Hz,1 H), 6.38 (dd, J = 1 .6 and 8.0 Hz, 1 H) 5.44 (bs, 1 H), 4.89 (bs, 2H).

References:

[1] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 – 1176.

[2] Chemistry – A European Journal, 2017, vol. 23, # 42, p. 9996 – 10000.

[3] Patent: WO2015/79251, 2015, A1, . Location in patent: Paragraph 00408; 00409.

2
[ 168335-63-5 ]
[ 100367-36-0 ]

References:

[1] Farmaco, 1995, vol. 50, # 6, p. 425 – 430.

[2] Journal of the American Chemical Society, 1995, vol. 117, # 25, p. 6666 – 6672.

3
[ 56619-93-3 ]
[ 100367-36-0 ]

References:

[1] Journal of the American Chemical Society, 1995, vol. 117, # 25, p. 6666 – 6672.

[2] Farmaco, 1995, vol. 50, # 6, p. 425 – 430.

4
[ 168335-61-3 ]
[ 100367-36-0 ]

References:

[1] Journal of the American Chemical Society, 1995, vol. 117, # 25, p. 6666 – 6672.

[2] Farmaco, 1995, vol. 50, # 6, p. 425 – 430.

5
[ 603-85-0 ]
[ 100367-36-0 ]

References:

[1] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 – 1176.

[2] Chemistry – A European Journal, 2017, vol. 23, # 42, p. 9996 – 10000.

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