80622-53-3|Methyl 2-(3-bromophenyl)propanoate| Ambeed

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Quality Control of [ 80622-53-3 ] Purity: 95% SDS Specification

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Product Details of [ 80622-53-3 ]

CAS No. :	80622-53-3
Formula :	C₁₀H₁₁BrO₂
M.W :	243.10
SMILES Code :	CC(C1=CC=CC(Br)=C1)C(OC)=O
MDL No. :	MFCD18908974
Boiling Point :	No data available
InChI Key :	IQJQUAGEAURVAU-UHFFFAOYSA-N
Pubchem ID :	13244717

Safety of [ 80622-53-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 80622-53-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	54.81
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.66
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	2.97
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.73
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.	2.99
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	2.89
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.85

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.36
Solubility	0.106 mg/ml ; 0.000435 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.	-3.19
Solubility	0.159 mg/ml ; 0.000652 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	-3.77
Solubility	0.0415 mg/ml ; 0.000171 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.	-5.67 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	0.0
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)	2.26

Application In Synthesis of [ 80622-53-3 ]

* 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 [ 80622-53-3 ]
Downstream synthetic route of [ 80622-53-3 ]

[ 80622-53-3 ] Synthesis Path-Upstream 1~6

1
[ 150529-73-0 ]
[ 74-88-4 ]
[ 80622-53-3 ]

Yield	Reaction Conditions	Operation in experiment
82.3%	Stage #1: With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5 h; Inert atmosphere Stage #2: at 20℃; for 3 h; Inert atmosphere	To a dry 100 mL three-necked flask was added methyl 3-bromophenylacetate (4.58 g, 20 mmol, 1.0 eq) under N2.Add anhydrous tetrahydrofuran (30 mL),A 2.0 M solution of lithium diisopropylamide in THF / heptane / ethylbenzene (10.5 mL, 21 mmol, 1.05 eq) was slowly added dropwise at -78 °C.After the completion of the dropwise addition, the mixture was stirred for 30 minutes, and then methyl iodide (2.84 g, 20 mmol,1.0eq). Stirring was continued at room temperature for a further 3 hours.60 mL of water was added to the reaction flask, followed by extraction with 50 mL of dichloromethane, and the mixture was separated.The aqueous phase was extracted twice more with 30 mL of dichloromethane. Combine the organic phase,Wash twice with saturated saline solution,Drying with anhydrous sodium sulfate, concentration, and the residue was separated by column chromatography.Methyl 2-(3-bromophenyl)propanoate 3.95 g was obtained in a yield of 82.3percent.

References: [1] Patent: CN108794319, 2018, A, . Location in patent: Paragraph 0033-0035.
[2] Green Chemistry, 2017, vol. 19, # 20, p. 4798 - 4803.
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 11, p. 3299 - 3311.

2
[ 67-56-1 ]
[ 53086-52-5 ]
[ 80622-53-3 ]

References: [1] Patent: WO2015/104684, 2015, A1, . Location in patent: Page/Page column 95.
[2] Patent: US2016/340328, 2016, A1, . Location in patent: Paragraph 0482; 0483.

3
[ 81712-05-2 ]
[ 80622-53-3 ]

References: [1] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 1, p. 99 - 105.

4
[ 19829-31-3 ]
[ 149-73-5 ]
[ 80622-53-3 ]

References: [1] Chemistry - A European Journal, 2016, vol. 22, # 45, p. 16072 - 16077.

5
[ 67-56-1 ]
[ 150529-73-0 ]
[ 80622-53-3 ]

References: [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 21, p. 3373 - 3380.

6
[ 1878-67-7 ]
[ 80622-53-3 ]

References: [1] Green Chemistry, 2017, vol. 19, # 20, p. 4798 - 4803.

[ 80622-53-3 ] Synthesis Path-Downstream 1~29

1
[ 81712-05-2 ]
[ 80622-53-3 ]