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[ CAS No. 5400-80-6 ] {[proInfo.proName]}

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Chemical Structure| 5400-80-6
Chemical Structure| 5400-80-6
Structure of 5400-80-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5400-80-6 ]

CAS No. :5400-80-6 MDL No. :MFCD00003798
Formula : C9H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :RTESDSDXFLYAKZ-UHFFFAOYSA-N
M.W : 213.07 Pubchem ID :95444
Synonyms :

Calculated chemistry of [ 5400-80-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.1
TPSA : 20.23 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) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.82
Log Po/w (XLOGP3) : 1.93
Log Po/w (WLOGP) : 1.72
Log Po/w (MLOGP) : 2.25
Log Po/w (SILICOS-IT) : 2.44
Consensus Log Po/w : 2.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.78
Solubility : 0.353 mg/ml ; 0.00166 mol/l
Class : Soluble
Log S (Ali) : -1.98
Solubility : 2.24 mg/ml ; 0.0105 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.05
Solubility : 0.19 mg/ml ; 0.000891 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.58

Safety of [ 5400-80-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5400-80-6 ]

* 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 [ 5400-80-6 ]
  • Downstream synthetic route of [ 5400-80-6 ]

[ 5400-80-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 5400-80-6 ]
  • [ 10485-09-3 ]
YieldReaction ConditionsOperation in experiment
77% With H-β-zeolite In chlorobenzene at 120℃; for 6 h; General procedure: In a 25 mL round bottomed flask, 250 mg (1.2 mmol) of 2-bromo-1-phenylethanol (1a), 50 mg (20 W/W percent) H-β-Zeolite and 1.0 mL of chlorobenzene were placed. The reaction flask was placed in an oil bath at 120°C for 6 h; the progress of the reaction was monitored by TLC. After completion of the reaction, the flask was allowed to attain room temperature, and filtered through Watt-Mann filter paper and washed with 10 mL of diethyl ether. Removal of the solvent under reduced pressure, the left out residue was purified by column chromatography on silica gel (200-400 mesh) and hexane as eluent to obtain 2a in (0.16 g) 72percent yield.
70% With toluene-4-sulfonic acid In toluene at 90℃; for 20 h; (2)
Synthesis of 2-bromoindene
25 g was taken from the bromohydrin compound obtained from the above reaction, dissolved in 300 mL of toluene, then 500 mg of p-toluene sulfonic acid was added thereto, and the temperature was raised to 90° C., and stirring was carried out for 20 h.
After the reactant was cooled to room temperature, it was washed with a sufficient amount of water, dehydrated with MgSO4, and filtered and dried under reduced pressure, thereby obtaining a brown concentrate.
This was dissolved in about 100 mL of hexane, and hexane was filtered as an eluent through a silica pad, thereby obtaining non-viscous yellow oil (2-bromoindene) in a yield of 60 to 70percent.
1H NMR (500 MHz, CDCl3): δ 3.61 (3H, s), 6.95 (1H, s), 7.18-7.20 (3H, m), 7.27-7.32 (1H, m), 7.39 (1H, m)
60% for 24 h; Heating Indene (259 mmol, 30 g) and distilled water (9 mL) were put into dimethyl sulfoxide (DMSO, 90 mL), the temperature was decreased to 0°C, and N-bromosuccinimide (NBS, 263 mmol, 46.9 g) was slowly added thereto. The temperature of this solution was increased to normal temperature, and the solution was agitated for 12 hours. After that, after the reaction was finished by distilled water, the organic layer was extracted with diethyl ether, and moisture was removed by anhydrous magnesium sulfate. After the filtration under reduced pressure, compound B (38.9 g, 72percent) was obtained by removing the solvent by reducing the pressure of the filtered solution and recrystallizing the solution by hexane. 14.3 g of compound B and p-toluenesulfonic acid (p-TsOH, 2.6 mmol, 0.5 g) were dissolved in 60 mL of toluene, and agitated and heated for 24 hours while water was removed by using the Tin-Stock method. Compound C (7.8 g, 60percent) was obtained by decreasing the temperature of the solution to normal temperature and using the fractionation method.
88.7 % With p-toluenesulfonic acid monohydrate In chloroform; toluene Preparation of 2-Bromoindene
To a 500 mL flask containing a magnetic stir bar was added (+/-)trans-2-bromo-1-indanol (50.0 g, 235 mmol), p-toluenesulfonic acid monohydrate (0.50 g, 2.6 mmol), and toluene (300 mL).
A Dean Stark trap and reflux condenser were placed on the flask, and the reaction was refluxed for 16 hours.
The reaction was transferred to a separatory funnel, chloroform was added (200 mL), and the resulting mixture was washed with aqueous sodium bicarbonate solution (3*200 mL).
The organic layer was then washed with a saturated aqueous sodium chloride solution (1*300 mL), dried over anhydrous magnesium sulfate, and filtered.
The solvents were removed and distillation provided 40.6 g (88.7 percent) of the slightly yellow crystalline solid collected at 72-105° C. at 3 mm Hg.
1 H NMR (300 MHz, CDCl3, TMS); δ7.4-7.1(m, 4H), 6.93(s, 1H), 3.60(s, 2H).
13 C NMR (75 MHz, CDCl3): δ143.62, 142.22, 132.64, 126.38, 124.59, 124.49, 122.85, 119.88, 45.40.
GC-MS: Calculated for C9 H7 79 Br 193.97, found 194.00.
Calculated for C9 H7 81 Br 195.90, found 195.90.

Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 10, p. 1793 - 1795
[2] Patent: US2016/194422, 2016, A1, . Location in patent: Paragraph 0129; 0138
[3] Journal of Organic Chemistry, 1982, vol. 47, # 4, p. 705 - 709
[4] Patent: EP2390249, 2011, A2, . Location in patent: Page/Page column 20-21
[5] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2222 - 2231
[6] Patent: US6342622, 2002, B1, . Location in patent: Example III
[7] Patent: US6015868, 2000, A,
[8] Polyhedron, 2017, vol. 126, p. 72 - 82
[9] Polyhedron, 2017, vol. 137, p. 284 - 295
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