105603-49-4|Methyl 5-bromo-2,3-dihydroxybenzoate| Ambeed

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Quality Control of [ 105603-49-4 ] Purity: 98% SDS Specification

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Product Details of [ 105603-49-4 ]

CAS No. :	105603-49-4
Formula :	C₈H₇BrO₄
M.W :	247.04
SMILES Code :	O=C(OC)C1=CC(Br)=CC(O)=C1O
MDL No. :	MFCD01412199
InChI Key :	DADZQRYTHXRMPM-UHFFFAOYSA-N
Pubchem ID :	53429428

Safety of [ 105603-49-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 105603-49-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	2.0
Molar Refractivity	49.47
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.76 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.24
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	2.46
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.65
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.	1.48
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	1.43
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.85

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.13
Solubility	0.183 mg/ml ; 0.00074 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.	-3.51
Solubility	0.0771 mg/ml ; 0.000312 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	-2.18
Solubility	1.62 mg/ml ; 0.00658 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.	-6.06 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.	1.0 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)	1.88

Application In Synthesis of [ 105603-49-4 ]

* 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 [ 105603-49-4 ]

[ 105603-49-4 ] Synthesis Path-Downstream 1~36

1
[ 67-56-1 ]
[ 72517-15-8 ]
[ 105603-49-4 ]

Yield	Reaction Conditions	Operation in experiment
78%		A mixture of thionyl chloride (0.35 mL, 4.8 mmol) and methanol (5.4 mL) was stirred at room temperature for 30 min then treated with part B compound (600 mg, 2.57 mmol). The reaction mixture was stirred at room temperature for 2.0 hr. refluxed for 7.0 hr, cooled and concentrated to a brown solid. Purification by column chromatography (2.5×25 cm column, 1:4 EtOAc/hexane, then 1:1 EtOAc) gave the title compound (500 mg, 78%).
12.5 g	With thionyl chloride; at 0℃;Reflux; Inert atmosphere;	SOCl2(13.1 mL, 180.9 mmol) was added dropwise into a solution of the compound (17-1) (14.1 g, 60.3 mmol) in 27 MeOH (200 mL) at 0C in a nitrogen atmosphere. A resulting mixture was stirred at reflux overnight. After a reaction was completed, a volatile solvent was evaporated under reduced pressure. A resulting residue was purified by means of a silica gel column chromatography, so as to obtain the 106 title compound (17-2) (12.5 g, 50.6 mmol, 84%). (0144) 1H NMR (400 MHz, CDCl3); delta 10.85 (s, 1H), 7.51 (s, 1H), 7.23 (s, 1H), 5.69 (s, 1H), 3.96 (s, 3H)

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2279 - 2280.
[2]Patent: US2003/225091,2003,A1 .Location in patent: Page 63.
[3]Patent: US2005/137162,2005,A1 .Location in patent: Page/Page column 6.
[4]Chemistry - A European Journal,2011,vol. 17,p. 6369 - 6381.
[5]Patent: EP3404033,2018,A1 .Location in patent: Paragraph 0143-0144.

2
[ 100-39-0 ]
[ 105603-49-4 ]
[ 182676-91-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 2279 - 2280.

3
[ 105603-49-4 ]
[ 240797-46-0 ]
[ 874447-89-9 ]

References: [1]Israel Journal of Chemistry,2005,vol. 45,p. 303 - 319.

4
[ 2051-90-3 ]
[ 105603-49-4 ]
[ 854472-28-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	at 160℃; for 0.666667h;	A suspension of the corresponding methyl 2,3-dihydroxybenzoate (1 eq.) in dichlorodiphenylmethane (1.5 eq.) was stirred at 160 C. for 40 min. After cooling to 50 C., 30 mL MeOH was added to the viscous brown oil leading to the formation of a precipitate. The precipitate was filtered, washed with MeOH (3×20 mL) and dried under high vacuum to yield the desired compound as a colorless solid. ; <strong>[105603-49-4]Methyl 5-bromo-2,3-dihydroxybenzoate</strong> (3 g, 12.87 mmol, 1 eq.) was reacted with dichlorodiphenylmethane (3.7 mL, 4.58 g, 19.31 mmol, 1.5 eq.) according to GP2, Method A. Yield: 4 g (76%). Colorless powder. Mp.: 146-148 C. IR (KBr): 3079w, 2950w, 1718s (CO); 1467s; 1355s; 1238s; 1204s; 1043s; 1013s; 944m; 867m; 780s. 1H-NMR (300 MHz, CDCl3); 3.94 (s, 3 H, CH3); 7.14 (d, J=1.9, 1 H, Harom, Cat.); 7.38-7.41 (m, 6 H, Harom, Ketal); 7.55-7.59 (m, 5 H, Harom, Cat., Harom, Ketal). 13C-NMR (75 MHz, CDCl3): 52.4; 112.6; 113.7; 115.6; 119.1; 125.0; 126.2; 128.3; 129.4; 139.0; 147.5; 149.1; 163.7. HR-MS (MALDI): calcd. for C21H16BrO4 ([M+H]+): 411.0231, found 411.0220.

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 1856 - 1887.
[2]Patent: US2005/137162,2005,A1 .Location in patent: Page/Page column 6; 10-11; 13.

5
[ 105603-49-4 ]
[ 854472-29-0 ]