55877-79-7|5-Chloro-2-methoxybenzonitrile| Ambeed

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Quality Control of [ 55877-79-7 ] Purity: 98% SDS Specification

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Product Details of [ 55877-79-7 ]

CAS No. :	55877-79-7
Formula :	C₈H₆ClNO
M.W :	167.59
SMILES Code :	ClC1=CC(=C(C=C1)OC)C#N
MDL No. :	MFCD00052867
InChI Key :	LREABOKKLIVXNA-UHFFFAOYSA-N
Pubchem ID :	2800979

Safety of [ 55877-79-7 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302+H312-H315-H319-H331-H335
Precautionary Statements:	P261-P280-P305+P351+P338-P311
Class:	6.1
UN#:	3439
Packing Group:	Ⅲ

Computational Chemistry of [ 55877-79-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	42.66
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.04
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	2.24
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.22
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.	1.71
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	2.43
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.63
Solubility	0.395 mg/ml ; 0.00236 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.	-2.57
Solubility	0.452 mg/ml ; 0.0027 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	-3.22
Solubility	0.101 mg/ml ; 0.000603 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.	-5.73 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	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)	1.5

Application In Synthesis of [ 55877-79-7 ]

* 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.

Downstream synthetic route of [ 55877-79-7 ]

[ 55877-79-7 ] Synthesis Path-Downstream 1~35

1
[ 64-17-5 ]
[ 55877-79-7 ]
[ 68216-06-8 ]

References: [1]Roczniki Chemii,1954,vol. 28,p. 663,666.
Chem.Abstr.,1956,p. 246.

2
[ 21663-61-6 ]
[ 124-41-4 ]
[ 55877-79-7 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1931,vol. 50,p. 753,779.
[2]Recueil des Travaux Chimiques des Pays-Bas,1931,vol. 50,p. 753,779.

3
[ 55877-79-7 ]
[ 3438-16-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In ethylene glycol; at 170℃; for 7h;	General procedure: 2-Ethylbenzonitrile (7.6mmol) and KOH (24.8mmol) were suspended in ethane-1,2-diol (10mL) and stirred at 170C for 7h. Then, the reaction mixture was cooled down to rt, H2O (50mL) was added and the resulting mixture was extracted three times with ether (30mL). pH of the aqueous layer was adjusted to 1 by diluted HCl and the aqueous phase was extracted three times with ether (40mL). Organic phases were collected, extracted three times with H2O (40mL) and dried over Na2SO4. The solvent was removed and obtained compound was directly used in the next step. Yield: 89.0%, white solid; mp: 64-65C; IR: 3400-2300 (b, OH), 2977 (as CH3), 2955 (as CH2), 2869 (s CH3), 1681 ( CO), 1601, 1575, 1488, 1447 ( CC aromatic) cm-1; 1H NMR (DMSO-d6, 300MHz): δ 12.79 (1H, br s, COOH), 7.76 (1H, d, J=7.0Hz), 7.43 (1H, t, J=7.5Hz), 7.33-7.21 (2H, m), 2.90 (2H, q, J=7.4Hz, CH2), 1.14 (3H, t, J=7.4Hz, CH3); 13C NMR (DMSO-d6, 75MHz): δ 169.14, 145.12, 131.96, 130.54, 130.35, 130.34, 126.04, 27.03, 16.32.

References: [1]Journal fur praktische Chemie (Leipzig 1954),1929,vol. <2> 120,p. 211,212.
[2]Tetrahedron,2016,vol. 72,p. 2072 - 2083.

4
[ 7035-09-8 ]
[ 55877-79-7 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2251 - 2255.

5
[ 55877-79-7 ]
[ 164670-74-0 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hexamethyldisilazane; In tetrahydrofuran; at 20℃; for 48h;	To a solution of <strong>[55877-79-7]5-chloro-2-methoxybenzonitrile</strong> (50 mg, 0.30 mmol) in anhydrous THF (1 mL) was added dropwise a solution of Lithium hexamethyldisilazane (5eq of 1 M solution in THF) at rt. The reaction mixture was stirred for 48 h and then acidified to pH = 3 with HC1 IN. The solvent was removed and the solution was basified to pH = 12 with NaOH 2 N. The product was extracted with DCM, the organic layer was dried (Na2S04) and the solvent was removed (Yield 87%). NMR (400MHZ, CDCI3) : 7,52 (1H, d), 7.27 (1H, d), 6.83 (1H, d), 5.70 (2H, NH), 3.82 (3H, s).

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2251 - 2255.
[2]Patent: WO2016/16370,2016,A1 .Location in patent: Page/Page column 43.

6
copper (I)-cyanide [ No CAS ]
diazotized 4-chloro-2-amino-anisole [ No CAS ]
[ 55877-79-7 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1929,vol. <2> 120,p. 211,212.

7
[ 55877-79-7 ]
[ 55877-78-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 1769 - 1780.

8
[ 24424-99-5 ]
[ 55877-79-7 ]
(5-chloro-2-methoxybenzyl)carbamic acid tert-butyl ester [ No CAS ]

References: [1]Tetrahedron,2003,vol. 59,p. 5417 - 5423.

9
[ 64-17-5 ]
[ 55877-79-7 ]
ethyl 5-chloro-2-methoxybenzimidate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With hydrogenchloride; In dichloromethane; at 0℃; for 120.5h;	Example 93D Ethyl 5-chloro-2-methoxybenzimidate hydrochloride A cooled solution of <strong>[55877-79-7]5-chloro-2-methoxybenzonitrile</strong> (9.3 g, 0.056 mol, Maybridge) and ethanol (16.2 mL, 0.28 mol) in CH2Cl2 (40 mL) was bubbled with HCl gas at 0 C. for 30 min. The reaction mixture was kept in refrigerator for 5 days. The reaction mixture was then concentrated and triturated with diethyl ether to remove unreacted starting material. The precipitate was dried under reduced pressure to obtain 7.1 g (51%) of the title compound. MS (ESI+) m/z 214 (M+H)+.
51%	With hydrogenchloride; In dichloromethane; at 0℃; for 120.5h;Cooling in refrigerator;	Example 128C; Ethyl 5-chloro-2-methoxybenzimidate hydrochloride; A cooled solution of <strong>[55877-79-7]5-chloro-2-methoxybenzonitrile</strong> (9.3 g, 0.056 mol, Maybridge) and ethanol (16.2 mL, 0.28 mol) in CH2Cl2 (40 mL) was bubbled with HCl gas at 0 0C for 30 min. The reaction mixture was kept in refrigerator for 5 days. The reaction mixture was then concentrated and triturated with diethyl ether to remove unreacted starting material. The precipitate was dried under reduced pressure to obtain 7.1 g (51%) of the title compound. MS (ESI+) m/z 214 (M+H)+.
51%	With hydrogenchloride; In dichloromethane; at 0℃; for 120.5h;	Example 128C; Ethyl 5-chloro-2-methoxybenzimidate hydrochloride; A cooled solution of <strong>[55877-79-7]5-chloro-2-methoxybenzonitrile</strong> (9.3 g, 0.056 mol, Maybridge) and ethanol (16.2 mL, 0.28 mol) in CH2Cl2 (40 mL) was bubbled with HCl gas at 0 0C for 30 min. The reaction mixture was kept in refrigerator for 5 days. The reaction mixture was then concentrated and triturated with diethyl ether to remove unreacted starting material. The precipitate was dried under reduced pressure to obtain 7.1 g (51%) of the title compound. MS (ESI+) m/z 214 (M+H)+.

References: [1]Patent: US2008/242654,2008,A1 .Location in patent: Page/Page column 67.
[2]Patent: WO2010/54024,2010,A2 .Location in patent: Page/Page column 122.
[3]Patent: WO2008/130953,2008,A2 .Location in patent: Page/Page column 106.
[4]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2303 - 2308.

10
[ 55877-79-7 ]
[ 774607-89-5 ]