[ CAS No. 1072004-32-0 ]

Name: 1072004-32-0|Methyl 3-fluoro-5-hydroxybenzoate|98%
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Quality Control of [ 1072004-32-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1072004-32-0 ]

CAS No. :	1072004-32-0	MDL No. :	MFCD14698043
Formula :	C₈H₇FO₃	Boiling Point :	290.7±25.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	170.14 g/mol	Pubchem ID :	46311142
Synonyms :

Calculated chemistry of of [ 1072004-32-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.7
TPSA :	46.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.72
Log Po/w (XLOGP3) :	1.93
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.75
Log Po/w (SILICOS-IT) :	1.64
Consensus Log Po/w :	1.75

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.35
Solubility :	0.762 mg/ml ; 0.00448 mol/l
Class :	Soluble
Log S (Ali) :	-2.53
Solubility :	0.501 mg/ml ; 0.00294 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.17
Solubility :	1.14 mg/ml ; 0.00673 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

Safety of [ 1072004-32-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338-P280	UN#:	N/A
Hazard Statements:	H319-H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1072004-32-0 ]

* 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 [ 1072004-32-0 ]

[ 1072004-32-0 ] Synthesis Path-Downstream 1~11

1
[ 1072004-32-0 ]
[ 1596093-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 4 h / Reflux 2: diisobutylaluminium hydride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2014/154859, 2014, A1

2
[ 1072004-32-0 ]
[ 106-95-6 ]
[ 1629996-54-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile for 4h; Reflux;	Allyl bromide (13 mL, 0.15 mmol) was added drop wise to a mixture of A3 (23 g, 0.135 mmol) and K2CO3 (28 g, 0.2 mmol) in CH3CN (460 mL). The mixture was stirred at reflux for 4 h, and then concentrated under reduced pressure. The residue was taken up with water and was extracted with EtOAc. The organic layers were combined, washed with water, dried over MgS04, filtered and the solvent was evaporated. The crude compound (27 g, 95% yield) was used directly in the next reaction step.
	With potassium carbonate; potassium iodide In acetone Reflux;	General procedure: Step 2: To a solution of methyl 3-hydroxybenzoate (0.95 g, 6.25 mmol), and potassium carbonate (2.59 g, 18.75 mmol), potassium iodide (311.3 mg, 1.9 mmol) in acetone (40 mL), allyl bromide (1.14 g, 9.4 mmol) was added and the mixture was stirred under reflux for 6 hours. The mixture was filtered and the solvent was evaporated. The residue was purified by column chromatography column chromatography on silica gel, and elution with petroleum ether/ethyl acetate (4:1) to obtain methyl 3-allyloxybenzoate (colorless oil, 1.0 g, 83.2% yield).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2014/154859, 2014, A1 Location in patent: Page/Page column 38; 39
[2]Chen, Chao; Zhang, Yi; Shi, Chen; Yang, Yaxi; Zhou, Bing [Tetrahedron Letters, 2022, vol. 108]

3
[ 860296-12-4 ]
[ 67-56-1 ]
[ 1072004-32-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With thionyl chloride Cooling with ice; Reflux;
99%	With thionyl chloride for 2h; Cooling with ice; Reflux;	6.a a. Preparation of Methyl 3-bromo-5-fluorobenzoate (25) General procedure: To an ice cold stirred solution of 3-bromo-5-fluorobenzoic acid (4.13 g, 18.9 mmol) in anhydrous methanol (40 mL) was added thionyl chloride (2.05 mL, 28.2 mmol) dropwise. The reaction mixture was allowed to stir for 15 min and then heated to reflux. Upon completion (1 h) the solvent was removed under reduced pressure, and the residue was taken into EtOAc (150 mL). The organic solution was washed with water (2×150 mL), brine (150 mL) and dried over MgSO4. The solids were filtered, and solvent removed under reduced pressure to yield compound 25 (4.00 g, 91% yield) as brown liquid. 1H NMR (300 MHz, CDCl3): δ ppm 7.95-7.93 (m, 1H), 7.64 (ddd, 1H, J=1.4, 2.4, 8.8 Hz), 7.41 (td, 1H, J=2.1, 7.8 Hz), 3.92 (s, 3H). 13C NMR (75 MHz, CDCl3): δ ppm 164.59 (d, J=3.1Hz), 162.25 (d, J=251.9 Hz), 133.36 (d, J=8.0 Hz), 128.54 (d, J=3.3 Hz), 123.38 (d, J=24.5 Hz), 122.60 (d, J=9.2 Hz), 115.48 (d, J=23.1 Hz), 52.66.
87%	With thionyl chloride at 0℃; for 3h; Reflux;	Methyl 2-fluoro-5-hydroxybenzoate (10c). General procedure: To a solution of 2-fluoro-5-hydroxybenzoic acid(1.56 g, 10 mmol) in anhydrous methanol (10 mL), thionly chloride (1.42 mL, 20mmol) was added dropwise at 0 °C. The reaction was allowed to warm to rt andreflux for 3 h. The solvent was removed under reduced pressure, water wasadded, and the mixture was extracted with DCM (80 mL). The organic layer was washedwith water, saturated brine, dried over anhydrous sodium sulfate, evaporated togive title compound as a white solid (1.5 g, 88% yield), which was used in thefollowing step without any further purification

	With sulfuric acid In water Inert atmosphere; Sealed tube; Reflux;
	With thionyl chloride
	With sulfuric acid Reflux;	Synthesis of 3-(allyloxy)-N-methoxybenzamide (1a) General procedure: Step 1: To a solution of 3-hydroxybenzoic acid (1.00 g, 7.24 mmol) in MeOH (30 mL), concentrated H2SO4 (0.5 mL) was added and then stir the solution under reflux overnight. After the solvent was evaporated and water was carefully poured into the residue. The reaction mixture was extracted with ethyl acetate for three times. The combined organic layers were washed by water and NaCl saturated solution and then were dried over MgSO4, filtered, concentrated under reduced pressure without further purification. There was thus obtained methyl 3-hydroxybenzoate, white solid (0.95 g, 86% yield).

Reference： [1]Wisniewski, John A.; Yin, Jinya; Teuscher, Kevin B.; Zhang, Min; Ji, Haitao [ACS Medicinal Chemistry Letters, 2016, vol. 7, # 5, p. 508 - 513]
[2]Current Patent Assignee: UNIVERSITY OF UTAH - US2021/171502, 2021, A1 Location in patent: Paragraph 0414-0415; 0440-0441
[3]Yang, Feipu; Jiang, Xiangrui; Li, Jianfeng; Wang, Yu; Liu, Yongjian; Bi, Minghao; Wu, Chunhui; Zhao, Qingjie; Chen, Weiming; Yin, Jingjing; Zhang, Jian; Xie, Yuanchao; Hu, Tianwen; Xu, Mingshuo; Guo, Shuang; Wang, Zhen; He, Yang; Shen, Jingshan [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3141 - 3147]
[4]Lin, Jian; Hu, Liuyu; Chen, Chao; Feng, Huijin; Yu, Yang; Yang, Yaxi; Zhou, Bing [Organic Letters, 2021, vol. 23, # 4, p. 1194 - 1198]
[5]Current Patent Assignee: ARVINAS - WO2022/87125, 2022, A1 Location in patent: Paragraph 00199
[6]Chen, Chao; Zhang, Yi; Shi, Chen; Yang, Yaxi; Zhou, Bing [Tetrahedron Letters, 2022, vol. 108]

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[ 1072004-32-0 ]
[ 109431-87-0 ]
[ 1895004-04-2 ]