5042-97-7|6-Chloro-2-naphthoic acid| Ambeed

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Quality Control of [ 5042-97-7 ] Purity: 95% SDS Specification

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Product Details of [ 5042-97-7 ]

CAS No. :	5042-97-7
Formula :	C₁₁H₇ClO₂
M.W :	206.63
SMILES Code :	O=C(O)C1=CC=C2C=C(Cl)C=CC2=C1
MDL No. :	MFCD11848443
InChI Key :	SRISHMVSUHENAI-UHFFFAOYSA-N
Pubchem ID :	13288327

Safety of [ 5042-97-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 5042-97-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	55.92
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.92
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	3.71
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.19
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.	3.19
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	2.96
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.99

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.92
Solubility	0.0248 mg/ml ; 0.00012 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.	-4.18
Solubility	0.0135 mg/ml ; 0.0000654 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-4.07
Solubility	0.0176 mg/ml ; 0.0000853 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	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.	-4.93 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.	0.56

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<2.0
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)	1.0

Application In Synthesis of [ 5042-97-7 ]

* 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 [ 5042-97-7 ]
Downstream synthetic route of [ 5042-97-7 ]

[ 5042-97-7 ] Synthesis Path-Upstream 1~10

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[ 5773-80-8 ]
[ 5042-97-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(l) iodide; copper(l) chloride In N,N-dimethyl-formamide for 4 h; Inert atmosphere; Reflux	Example 32 Synthesis of Compound 32 6-chloro-2-naphthoic acid A suspension of 6-bromo-2-naphthoic acid (3.0 g, 11.47 mmol), CuCl (11.7 g, 114.64 mmol) and CuI (2.19 g, 11.50 mmol) in degassed DMF (45 mL) was heated to reflux under argon in dark for 4 hrs. After cooling to room temperature, the solution was decanted into H₂O (200 mL) and the resulting mixture was extracted with EtOAc (2500 mL). The combined organic layers were then washed with H₂O (4500 mL) followed by brine (1*500 mL), dried over MgSO₄, filtered and concentrated under reduced pressure to dryness. The residue was trituated with CH₃CN and the solid obtained was then re-crystallized from EtOAc to give the pure product 32 (2.2 g, 93percent) as an off-white solid. HPLC t_R 6.47 min.
93%	With copper(l) iodide; copper(l) chloride In N,N-dimethyl-formamide for 4 h; Inert atmosphere; Darkness; Reflux	Example 66 - Synthesis of Compound 68 6-chloro-2-naphthoic acid686-chloro-2 -naphthoic acidA suspension of 6-bromo-2-naphthoic acid (3.0 g, 11.47 mmol), CuCI (1 1.7 g, 114.64 mmol) and CuI (2.19 g, 1 1.50 mmol) in degassed DMF (45 ml.) was heated to reflux under argon in dark for 4 hrs. After cooling to room temperature, the solution was decanted into H₂O (200 ml.) and the resulting mixture was extracted with EtOAc (2 x 500 mL). The combined organic layers were then washed with H₂O (4 x 500 mL) followed by brine (1 x 500 mL), dried over MgSO₄, filtered and concentrated under reduced pressure to dryness. The residue was trituated with CH₃CN and the solid obtained was then re-crystallized from EtOAc to give the pure product 68 (2.2 g, 93percent) as a off-white solid. HPLC f_R 6.47 min.
93%	With copper(l) iodide; copper(l) chloride In N,N-dimethyl-formamide for 4 h; Reflux; Inert atmosphere; Darkness	A suspension of 6-bromo-2-naphthoic acid (3.0 g, 11.47 mmol), CuCI (1 1.7 g, 114.64 mmol) and CuI (2.19 g, 1 1.50 mmol) in degassed DMF (45 ml.) was heated to reflux under argon in dark for 4 hrs. After cooling to room temperature, the solution was decanted into H₂O (200 ml.) and the resulting mixture was extracted with EtOAc (2 x 500 ml_). The combined organic layers were then washed with H₂O (4 x 500 ml.) followed by brine (1 x 500 ml_), dried over MgSO₄, filtered and concentrated under reduced pressure to dryness. The residue was trituated with CH₃CN and the solid obtained was then re-crystallized from EtOAc to give the pure product 70 (2.2 g, 93percent) as a off-white solid. HPLC fe 6.47 min

93%	With copper(l) iodide; copper(l) chloride In N,N-dimethyl-formamide for 4 h; Inert atmosphere; Darkness; Reflux	A suspension of 6-bromo-2-naphthoic acid (3.0 g, 11.47 mmol), CuCl (11.7 g, 114.64 mmol) and CuI (2.19 g, 11.50 mmol) in degassed DMF (45 mL) was heated to reflux under argon in dark for 4 hrs. After cooling to room temperature, the solution was decanted into H₂O (200 mL) and the resulting mixture was extracted with EtOAc (2500 mL). The combined organic layers were then washed with H₂O (4500 mL) followed by brine (1*500 mL), dried over MgSO₄, filtered and concentrated under reduced pressure to dryness. The residue was trituated with CH₃CN and the solid obtained was then re-crystallized from EtOAc to give the pure product 68 (2.2 g, 93percent) as a off-white solid. HPLC t_R 6.47 min.
75%	With CuI In N,N-dimethyl-formamide	Step 1. To a solution of 6-bromo-2-naphthoic acid (4.4 g, 17.5 mmol) in 50 mL anhydrous DMF were added CuCl (8.7 g, 87.5 mmol) and CuI (0.2 g). The slurry was refluxed for 1 hour. At room temperature it was diluted with 300 mL EtOAc and stirred for 2 hours. It was filtered through celite. The filtrate was evaporated in vacuuo to afford 6-chloro-2-naphthoic acid (2.7 g, 75percent). ES-MS: (M+H)⁺207.

References: [1] Patent: US2009/221557, 2009, A1, . Location in patent: Page/Page column 120.
[2] Patent: WO2010/96853, 2010, A1, . Location in patent: Page/Page column 104.
[3] Patent: WO2010/96854, 2010, A1, . Location in patent: Page/Page column 119.
[4] Patent: US2012/141392, 2012, A1, . Location in patent: Page/Page column 57.
[5] Patent: US2002/91116, 2002, A1, .
[6] Patent: US6632815, 2003, B2, .
[7] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6463 - 6466.
[8] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1229 - 1234.
[9] Patent: WO2017/192304, 2017, A1, . Location in patent: Paragraph 0149.

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References: [1] Patent: WO2004/48314, 2004, A1, . Location in patent: Page 45-46.
[2] Patent: WO2006/85118, 2006, A2, . Location in patent: Page/Page column 29.

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References: [1] European Journal of Medicinal Chemistry, 1984, vol. 19, # 3, p. 205 - 214.
[2] Chem.Abstr., 1976, vol. 85, # 94079, .

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[ 2065-70-5 ]
[ 1141-38-4 ]
[ 5042-97-7 ]