307353-32-8|Methyl 3-bromo-5-(hydroxymethyl)benzoate| Ambeed

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Quality Control of [ 307353-32-8 ] Purity: 95% SDS Specification

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Product Details of [ 307353-32-8 ]

CAS No. :	307353-32-8
Formula :	C₉H₉BrO₃
M.W :	245.07
SMILES Code :	O=C(OC)C1=CC(CO)=CC(Br)=C1
MDL No. :	MFCD11040228
Boiling Point :	No data available
InChI Key :	PWAJHVDGAMQOPF-UHFFFAOYSA-N
Pubchem ID :	11356988

Safety of [ 307353-32-8 ]

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

Computational Chemistry of [ 307353-32-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	51.55
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.34
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.	1.58
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.	2.09
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	2.24
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.96

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.5
Solubility	0.778 mg/ml ; 0.00317 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.	-2.17
Solubility	1.66 mg/ml ; 0.00679 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	-3.16
Solubility	0.169 mg/ml ; 0.000689 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.	-6.67 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)	1.79

Application In Synthesis of [ 307353-32-8 ]

* 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 [ 307353-32-8 ]

[ 307353-32-8 ] Synthesis Path-Downstream 1~35

1
[ 220286-47-5 ]
[ 307353-32-8 ]

Yield	Reaction Conditions	Operation in experiment
62%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃; for 0.5h;	Methyl 3-bromo-5-(hydroxymethyl)benzoate. Methyl 3-amino-5-(hydroxymethyl)benzoate (2.4 g, 13.2 mmol) in dry acetonitrile (10 mL) was added dropwise to a solution of copper (II) bromide (3.54 g, 15.8 mmol) and tert-butyl nitrite (2.24 mL, 18.9 mmol) in acetonitrile (20 mL) at 65 C. After stirring for 30 min at 65 C., the reaction mixture was cooled to room temperature, poured into a 1 N hydrochloric acid solution, and extracted with ethyl acetate (2×). The organic layers were pooled together, washed with brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (30% ethyl acetate/hexanes) afforded 2.0 g (62%). 1H-NMR (CDCl3, 300 MHz) delta 8.04 (s, 1H), 7.90 (s, 1H), 7.69 (s, 1H), 4.70 (s, 2H), 3.89 (s, 3H). Mass spec.: 246.98 (MH)+.

References: [1]Patent: US2007/249607,2007,A1 .Location in patent: Page/Page column 85.

2
[ 307353-32-8 ]
[ 877624-40-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-Bromosuccinimide; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 16.0h;	Methyl 3-bromo-5-(bromomethyl)benzoate. Methyl 3-bromo-5-(hydroxymethyl)benzoate (2.0 g, 8.2 mmol) and triphenylphosphine (4.28 g, 16.3 mmol) were combined in tetrahydrofuran (20 mL) and cooled to 0 C. N-Bromosuccinimide (3.05 g, 17.1 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with ethyl acetate, washed with concentrated sodium bicarbonate (2×), then brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (10% ethylacete/hexanes) gave 2.1 g (83%) as a light brown oil. 1H-NMR (CDCl3, 300 MHz) delta 8.07 (s, 1H), 7.96 (s, 1H), 7.70 (s, 1H), 4.42 (s, 2H), 3.90 (s, 3H). Mass spec.: 308.93 (MH)+.

References: [1]Patent: US2007/249607,2007,A1 .Location in patent: Page/Page column 85.

3
[ 51760-21-5 ]
[ 307353-32-8 ]
[ 51760-22-6 ]

Yield	Reaction Conditions	Operation in experiment
83.3%	With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0℃; for 5.0h;Cooling with ice;	A three-necked flask having a capacity of 2 liters was charged with 109.2g of dimethyl 5-bromo-isophthalate and then with 400 ml of tetrahydrofuran (THF), to prepare a solution of dimethyl 5-bromoisophthalate. The solution was mixed with 16.6g of sodium borohydride and the resultant mixture liquid was agitated while cooling the mixture liquid with ice pieces. Separately, 40.5 ml of methyl alcohol were dissolved in 150 ml of THF, the resultant solution was mixed in the ice-cooled mixture liquid. Then, the resultant reaction mixture liquid was agitated for 5 hours while cooling with ice pieces. The reaction mixture liquid was added with 380 ml of water to terminate the reaction, and then mixed with a 1 mole hydrochloric acid solution to adjust the pH value of the reaction mixture liquid to 7.0. The resultant reaction mixture liquid was subjected to an extraction treatment with 380 ml of ethyl acetate and then with 200 ml of ethyl acetate. The resultant organic extract liquids were mixed with each other, and the resultant mixed extract liquid was washed with 300 ml of water and then with 80 ml of a saturated aqueous common salt solution, and the resultant washed extract liquid was dried with a drying agent consisting of anhydrous magnesium sulfate. The dried extract liquid was filtered to separate the drying agent, and the resultant filtrate was concentrated. A crude product of the target compound, namely methyl 5-bromo-3-(hydroxymethyl)benzoate was obtained in an amount of 96.5g. In the crude product, the mass ratio of the target compound, namely methyl 5-bromo-3-(hydroxymethyl)benzoate to the by-product consisting of 5-bromo-3-(hydroxymethyl)benzyl alcohol was 88:10, as determined by NMR measurement. The crude product was dissolved in 160 ml of methyl alcohol; the resultant solution was placed in a separatory funnel and mixed with 160 ml of water and 1000 ml of xylene; and the resultant mixture liquid was subjected to a phase separation. The resultant organic phase fraction was collected, washed with 160 ml of a solution of methyl alcohol in water in volume ratio of 1:1, then with 160 ml of water and finally with 160 ml of a saturated aqueous common salt solution. The washed organic phase fraction was dried with a drying agent consisting of anhydrous magnesium sulfate. The dried solution was subjected to a filtration procedure to remove the drying agent from the organic phase fraction. Then, the filtrate was concentrated. The target compound, namely, purified methyl 5-bromo-3-(hydroxymethyl)benzoate was obtained in an amount of 81.98g. The yield thereof was 83.3%. In the resultant purified product, a mass ratio of the target compound, methyl 5-bromo-3-(hydroxymethyl)benzoate to a by-product, namely, 5-bromo-3-(hydroxymethyl)benzyl alcohol was 96:1.8, determined by the NMR measurement. The results of the 1H-NMR measurement (200 MHz, delta ppm, CDCl3) were as follows 3.93(s, 3H), 4.74 (d, J = 5.6 Hz, 2H) 7.73 (s, 1H), 7.95 (s, 1H), 8.09 (s, 1H).

References: [1]Patent: EP1460059,2004,A1 .Location in patent: Page 8.

4
[ 307353-32-8 ]
[ 377734-27-5 ]

Yield	Reaction Conditions	Operation in experiment
94.3%	With manganese dioxide; In toluene; at 105℃; for 7.0h;	In a three-necked flask with a capacity of 3 liters, 253.11g of <strong>[307353-32-8]methyl 5-bromo-3-(hydroxymethyl)benzoate</strong> were placed and mixed with 2000 ml of toluene, and the resultant mixture was agitated to prepare a solution. The resultant solution was mixed with 44g of manganese dioxide, and the resultant reaction mixture liquid was heated to a temperature of 105C and agitated for 7 hours. The resultant reaction mixture liquid was allowed to be cooled to room temperature and filtered to remove a solid fraction therefrom, and the resultant filtrate was concentrated. The target compound, methyl 5-bromo-3-formylbenzoate was obtained in an amount of 236.79g which corresponded to a yield of 94.3%. The results of the 1H-NMR (200 MHz, delta ppm, CDCl3) of the resultant compound were as follows. 3.98 (s, 3H), 8.1 - 8.3 (m, 1H), 8.3 - 8.6 (m, 2H), 10.0 (s, 1H)
	With manganese(IV) oxide; In dichloromethane; at 20℃;	A mixture of <strong>[307353-32-8]methyl 3-bromo-5-(hydroxymethyl)benzoate</strong> (149 mg, 0.61 mmol) and manganese(IV) oxide (529 mg, 6.08 mmol), and CH2Cl2 (3 mL) was stirred at rt overnight. The mixture was filtered through Celite and the filter cake was washed with CH2Cl2. The filtrate was concentrated to afford the title compound.

References: [1]Patent: EP1460059,2004,A1 .Location in patent: Page 9-10.
[2]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 123.

5
dimethyl 3-bromoisophthalate [ No CAS ]
[ 307353-32-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium borohydrid; In tetrahydrofuran; methanol;	Productive Example 2 Preparation of methyl 3-bromo-5-(hydroxymethyl)benzoate In 25 ml of tetrahydrofuran, was dissolved 10.00 g of dimethyl 3-bromoisophthalate. 1.66 g of sodium borohydride was added to the above solution and thereby a suspension was obtained. A mixed solution of 7.4 ml of methanol and 25 ml of tetrahydrofuran was slowly dropped into the resulting suspension. After completing the dropping, the reaction solution was refluxed for 30 minutes. A 1 M hydrochloric acid was added to the solution to quench the reaction. The resulting solution was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate. The solvent was removed under reduced pressure to afford 9.30 g of the title compound as a colorless oil quantitatively. 1H-NMR (270 MHz, CDCl3): delta 53.9 (s, 3H), 4.73 (d, 2H, J=5.4 Hz), 7.7-8.1 (m, 3H).

References: [1]Patent: US6538137,2003,B1 .

7
[ 161796-10-7 ]
[ 307353-32-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 60℃; for 12.5h;	Method 125; Methyl 3-bromo-5-(hydroxymethyl)benzoate; A solution of 3-bromo-5-(methoxycarbonyl)benzoic acid (Method 97; 1.2 g, 4.6 5 mmol) in anhydrous THF (20 ml) was treated with BH3-dimethyl sulfide (2.0 M in THF, 3.5 ml, 6.9 mmol) dropwise under nitrogen at 0 C. The mixture was stirred at 0 C for 30 min then heated up to 60 C for 12 hours. The reaction mixture was quenched with H2O-acetic acid (1 :2) (3 ml) and then diluted with EtOAc. The organics were washed with NaHCO3 (sat) and then dried with NaCl (sat) followed by Na2SO4 (s). The solvents were removed under 10 reduced pressure to give the desired product.

References: [1]Patent: WO2006/40568,2006,A1 .Location in patent: Page/Page column 81.

8
[ 51760-21-5 ]
[ 307353-32-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of dimethyl 5-bromoisophthalate (5.4 g, 20 mmol) in methanol (300 mL) at 0 0C was slowly added sodium tetrahydroborate (1O g, 0.28 mol). The mixture was stirred at rt for 3 h, and then treated with water (300 mL). The volatiles were removed in vacuo and the aqueous phase was extracted with CH2Cl2 (100 niL x 3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The resulting oil was purified by flash chromatography to afford the title compound.

References: [1]Patent: EP1179527,2002,A1 .Location in patent: Page 20.
[2]Journal of the American Chemical Society,2012,vol. 134,p. 1673 - 1679.
[3]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 531 - 536.
[4]Patent: WO2009/110985,2009,A2 .Location in patent: Page/Page column 122-123.

9
[ 307353-32-8 ]
[ 150255-96-2 ]
[ 225657-76-1 ]

References: [1]Patent: EP1179527,2002,A1 .Location in patent: Page 21.
[2]Patent: EP1179527,2002,A1 .Location in patent: Page 21.
[3]Patent: EP1179527,2002,A1 .Location in patent: Page 20.

10
[ 307353-32-8 ]
[ 123065-61-2 ]

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 1673 - 1679.

11
[ 307353-32-8 ]
[ 1334304-19-6 ]

References: [1]Patent: WO2012/68450,2012,A1 .

12
[ 307353-32-8 ]
[ 1334304-20-9 ]

References: [1]Patent: WO2012/68450,2012,A1 .

13
[ 307353-32-8 ]
[ 1334304-21-0 ]

References: [1]Patent: WO2012/68450,2012,A1 .

14
[ 307353-32-8 ]
potassium [(dimethylamino)methyl](trifluoro)borate^(1-) [ No CAS ]
[ 1334304-18-5 ]

Yield	Reaction Conditions	Operation in experiment
34%	With palladium diacetate; caesium carbonate; XPhos; In tetrahydrofuran; water; at 80℃; for 17.0h;Inert atmosphere; sealed vessel;	Step A. Methyl 3-[ (dimethylamino)methyl]-5-(hydroxymethyl)benzoateTo a reaction vial was added <strong>[307353-32-8]methyl 3-bromo-5-(hydroxymethyl)benzoate</strong> (1.2 g, 4.9 mmol, prepared as described in WO 2003/048111 from dimethyl 5- bromoisophthalate, Alfa Aesar), cesium carbonate (4.79 g, 14.7 mmol),dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (280 mg, 0.59 mmol, Aldrich), potassium [(dimethylamino)methyl](trifluoro)borate(l-) (0.970 g, 5.88 mmol, Aldrich), palladium acetate (66 mg, 0.29 mmol) and THF:H20 (10: 1, 30 mL). The reaction mixture was degassed by purging with a stream of nitrogen for 10 minutes. The vial was sealed and heated at 80 C for 17 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was was washed twice with water. The combined aqueous portions were then saturated with NaCl, and the product was extracted with eight portions of DCM. The extracts were dried over sodium sulfate, filtered and concentrated to afford product as a colorless oil (0.37 g, 34%). 1H NMR (300 MHz, CDC13): delta 7.94 (s, 1H), 7.88 (s, 1H), 7.56 (s, 1H), 4.74 (s, 2H), 3.91 (s, 3H), 3.46 (s, 2H), 2.24 (s, 6H); LCMS (M+H)+: 224.1.

References: [1]Patent: WO2012/68450,2012,A1 .Location in patent: Page/Page column 198.

15
[ 307353-32-8 ]
[ 52721-69-4 ]
3-bromo-N-[2-(2-fluorophenyl)ethyl]-5-(hydroxymethyl)benzamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 531 - 536.

16
[ 307353-32-8 ]
3-bromo-N-[2-(2-fluorophenyl)ethyl]-5-formylbenzamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 531 - 536.

17
[ 307353-32-8 ]
N-[2-(2-fluorophenyl)ethyl]-3-formyl-5-[6-(methyloxy)-3-pyridinyl]benzamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 531 - 536.

18
[ 307353-32-8 ]
N-(2-fluorophenethyl)-3-(6-methoxypyridin-3-yl)-5-(((4-(N-methyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)sulfamoyl)phenyl)amino)methyl)benzamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 531 - 536.

19
[ 307353-32-8 ]
[ 144025-03-6 ]
C₁₅H₁₂F₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium dihydrogenphosphate; In toluene; at 140℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Step 1 (0579) Compound iii-51 (300mg, 1.22mmol), (2,4-difluorophenyl)boronic acid (290mg, 1.84mmol), PdCl2 (dppf) (90mg, 0.12mmol) and potassium phosphate (780mg, 3.67mmol) were dissolved into toluene (12mL) under nitrogen atmosphere under microwave irradiation, and the mixture was stirred at 140C for 30 minutes. After the reaction mixture was filtrated by Celite, the solvent was removed in vacuo. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give Compound iii-52 (304mg, 89%). 1H-NMR (CDCl3) delta: 8.09-8.05 (m, 2H), 7.72 (d, J = 1.5 Hz, 1H), 7.46-7.40 (m, 1H), 7.00-6.91 (m, 2H), 4.82 (d, J = 5.8 Hz, 2H), 3.94 (s, 3H), 1.83 (t, J = 5.9 Hz, 1H).

References: [1]Patent: EP3192794,2017,A1 .Location in patent: Paragraph 0578; 0579.

20
[ 307353-32-8 ]
[ 144025-03-6 ]
C₁₆H₁₄F₂O₅S [ No CAS ]

References: [1]Patent: EP3192794,2017,A1 .

21
[ 307353-32-8 ]
[ 1186519-96-9 ]