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[ CAS No. 128577-48-0 ] {[proInfo.proName]}

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Chemical Structure| 128577-48-0
Chemical Structure| 128577-48-0
Structure of 128577-48-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 128577-48-0 ]

CAS No. :128577-48-0 MDL No. :MFCD03840738
Formula : C9H8Br2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZTDXOVAPGGNGSD-UHFFFAOYSA-N
M.W : 307.97 Pubchem ID :19806367
Synonyms :

Calculated chemistry of [ 128577-48-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.26
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.63
Log Po/w (XLOGP3) : 3.02
Log Po/w (WLOGP) : 2.98
Log Po/w (MLOGP) : 3.39
Log Po/w (SILICOS-IT) : 3.39
Consensus Log Po/w : 3.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.8
Solubility : 0.0493 mg/ml ; 0.00016 mol/l
Class : Soluble
Log S (Ali) : -3.24
Solubility : 0.178 mg/ml ; 0.000579 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.57
Solubility : 0.00833 mg/ml ; 0.000027 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.02

Safety of [ 128577-48-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P362+P364-P405-P501 UN#:3261
Hazard Statements:H302+H312-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 128577-48-0 ]

* 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.

  • Upstream synthesis route of [ 128577-48-0 ]
  • Downstream synthetic route of [ 128577-48-0 ]

[ 128577-48-0 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 87808-49-9 ]
  • [ 128577-48-0 ]
YieldReaction ConditionsOperation in experiment
94% With tert.-butylhydroperoxide; cetyltrimethylammonim bromide; potassium bromide In water at 120℃; Microwave irradiation General procedure: The reaction mixture was treated in a controlled microwavesynthesizer (Biotage Initiator+SP Wave model, 0–200 W at2.45 GHz, capped at 60 W during steady state) for severalminutes (the reaction attained 120 °C at 1 bar pressure). Thefinal products were isolated by column chromatographyusing an EtOAc–hexane gradient
48% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In 1,2-dichloro-ethane at 90℃; for 1 h; 2-Bromo-4-methylbenzoate (4.6 g, 20.08 mmol) was dissolved in anhydrous 1,2- dichioroethane (60.0 ml), and N-bromosuccinimide (4.3 g, 24.10 mmol) and AIBN (0.3 g, 2.01 mmol) were added at room temperature. The mixture was refluxed at 90°C for 1 hour, followed by cooling to room temperature and extracted with CH2C12. The organic extractwas washed with brine, dried over anhydrous Na2SO4, and concentrated under a reduced pressure. The residue was purified by reversed-phase column chromatography (C 18-silica gel, 0.1percent formic acid in CH3CN: 0.1percent formic acid in H20) to obtain methyl 2-bromo-4- (bromomethyl)benzoate (3.0 g, 48percent) as a colorless liquid.LC/MS ESI (+): 309 (M+1)‘H-NMR(400MHz, CDC13): ö 7.78 (d, 1H, J=8.OHz), 7.69 (d, 1H, J1.6Hz), 7.38 (dd, 1H,J=8.0, 1.6Hz), 4.42 (s, 2H), 3.94 (s, 3H)
45% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 1 h; Heating / reflux Step 1: To a solution of 2-bromo-4-methyl-benzoic acid (5.50 g, 25.6 mmol) in methanol (250 mL) was added concentrated sulfuric acid (1 mL). The reaction mixture was heated to reflux overnight (approximately 16 hours), allowed to cool to room temperature and then concentrated to approximately {fraction (1/4)} volume under reduced pressure. The residue was then partitioned between water and ethyl acetate, the layers were separated and the aqueous layer was extracted with one additional portion of ethyl acetate. The combined organics were washed one time with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered through a plug of silica gel and concentrated under reduced pressure. 2-Bromo-4-methyl-benzoic acid methyl ester was obtained as an oil (4.95 g, 85percent). To a solution of this oil (2.50 g, 10.9 mmol) in carbon tetrachloride (100 mL) was added N-bromosuccinimide (2.04 g, 11.5 mmol) and benzoylperoxide (0.106 g, 0.44 mmol). The reaction mix was heated to reflux. After approximately 1 hour, the reaction mixture became colorless. At this time the heat was removed to allow the mixture to cool to room temperature and the mixture was filtered. The filtrate was concentrated under reduced pressure. The crude mixture was purified by HPLC (40percent methylene chloride in hexane) to give 2-bromo-4-bromomethyl-benzoic acid methyl ester (1.50 g, 45percent) as a white powder. 1H NMR (400 MHz, CDCl3); δ 7.75 (d, 1H), 7.66 (s, 1H), 7.35 (d, 1H), 4.39 (s, 2H), 3.90 (s, 3H).
36% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2 h; Heating / reflux NBS (8.53 g, 48 mmol) was added to a solution of methyl 2-bromo-4- methylbenzoate (10.4 g, 45.6 mmol) in CCl4 (400 ml), followed by benzyol peroxide (441 mg, 1.82 mmol). The reaction mixture was then heated to reflux and after 2 h, the reaction mix became colorless. The mixture was allowed to cool to room temperature and before it was filtered. The filtrate was concentrated to give 12 g of crude material which was purified by column chromatography (440 g silica gel 60, 230-400 mesh, 10 then 20 percent CH2Cl2/hexane) to give methyl 2-bromo-4-(bromomethyl)benzoate (5.07 g, 36 percent) as a white solid. MS (m/z) 307.3(M+H+).

Reference: [1] Synlett, 2014, vol. 25, # 17, p. 2485 - 2487
[2] Patent: WO2016/89062, 2016, A2, . Location in patent: Page/Page column 38; 39
[3] Patent: US2005/70584, 2005, A1, . Location in patent: Page/Page column 24
[4] Patent: WO2008/124575, 2008, A1, . Location in patent: Page/Page column 144
[5] Patent: WO2017/156165, 2017, A1, . Location in patent: Paragraph 00504; 00505
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