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[ CAS No. 119999-22-3 ] {[proInfo.proName]}

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Chemical Structure| 119999-22-3
Chemical Structure| 119999-22-3
Structure of 119999-22-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 119999-22-3 ]

CAS No. :119999-22-3 MDL No. :MFCD08235072
Formula : C15H21Br Boiling Point : -
Linear Structure Formula :- InChI Key :ONNHBALCPUEXBT-UHFFFAOYSA-N
M.W : 281.23 Pubchem ID :10039346
Synonyms :

Calculated chemistry of [ 119999-22-3 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.6
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 75.53
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.47
Log Po/w (XLOGP3) : 6.1
Log Po/w (WLOGP) : 5.11
Log Po/w (MLOGP) : 5.17
Log Po/w (SILICOS-IT) : 5.53
Consensus Log Po/w : 5.08

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.7
Solubility : 0.000556 mg/ml ; 0.00000198 mol/l
Class : Moderately soluble
Log S (Ali) : -5.88
Solubility : 0.00037 mg/ml ; 0.00000131 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.27
Solubility : 0.000152 mg/ml ; 0.00000054 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.35

Safety of [ 119999-22-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 119999-22-3 ]

* 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 [ 119999-22-3 ]
  • Downstream synthetic route of [ 119999-22-3 ]

[ 119999-22-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 6223-78-5 ]
  • [ 95-46-5 ]
  • [ 119999-22-3 ]
YieldReaction ConditionsOperation in experiment
78% With aluminum (III) chloride In dichloromethane for 1.08333 h; Inert atmosphere 2,5-dimethylhexane-2,5-diol (10.0 g, 68.4 mmol) was stirred in 50 mL of conc. aq. HCl for 16 hr. The reaction was diluted with 50 mL of H2O and extracted with Et2O (3×50 mL). The combined organics were evaporated to 30 mL. A white crystalline solid precipitated and was collected via filtration (8.8 g, 70percent) and was not purified further. 1H NMR (400 MHz, CDCl3): δ = 1.96 (s, 4H), 1.61 (s, 12H). 1H NMR matches literature.5 2,5-dichloro-2,5-dimethylhexane (5.50 g, 30.0 mmol) and o-bromotoluene (10.3 g, 60.0 mmol) were dissolved in 60 mL of DCM. AlCl3 (400 mg, 3.00 mmol) was added slowly over 5 minutes. The reaction was stirred for 1 hr under an Ar atmosphere. 50 mL of H2O was added to the reaction and the layers were separated. The aqueous was extract with hexane (3×50 mL). The combined organics were dried with MgSO4, filtered, and removed under vacuum to yield an oil. The oil was dissolved in 75 mL of boiling MeOH and then cooled in an ice bath. The mixture was filtered to yield white crystals (6.6 g, 78percent). 1H NMR (400 MHz, CDCl3): δ = 7.43 (s, 1H), 7.15 (s, 1H), 2.35 (s, 3H), 1.66 (s, 4H), 1.26 (s, 12H). 1H NMR matches literature[5].
53% With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃; for 0.5 h; Inert atmosphere Reactor under a nitrogen purge to 2,5-dichloro-2,5-dimethyl-hexane (18.3 g, 100 mmol), 2-bromotoluene (17.1 g (100mmol) and 1,2-dichloroethane into a 200 ml by stirring, where the charged aluminum chloride (1.33 g, 10 mmol) all at once and stir at room temperature for 30 minutes. after the reaction was completed, into water, the organic layer was extracted with dichloromethaneThe magnesium treatment, and concentrated under reduced pressure to remove water.Is recrystallized by using methanol Melting point 73 white solid of 6-bromo -1,1,4,4,7- pentamethyl-1,2,3,4-tetrahydronaphthalene 15 g (yield 53percent) It was obtained.
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 46, p. 8067 - 8070
[2] Chemistry - A European Journal, 2013, vol. 19, # 10, p. 3504 - 3511
[3] Tetrahedron Letters, 2017, vol. 58, # 50, p. 4703 - 4708
[4] Patent: KR101515814, 2015, B1, . Location in patent: Paragraph 0307; 0308
  • 2
  • [ 108-88-3 ]
  • [ 119999-22-3 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With hydrogenchloride In water; toluene at 20℃;
Stage #2: at 60℃; for 2 h;
Stage #3: With hydrogen bromide; dihydrogen peroxide; propionic acid In water at 50 - 80℃; for 3 h;
step A-A 100 gal glass-lined reactor was charged with 1a (CAS Reg. No. 110-03-2, 18.1 Kg), toluene (30.4 Kg) and 37percent HCl (225 Kg). The biphasic mixture was stirred overnight at RT. After draining off the lower layer, the toluene solution was added to AlCl3 (1.23 Kg) over 1 h. The mixture was aged at 60° C. for 2 h. An aqueous HCl solution (2.93 Kg of 37percent HCl diluted with 7.07 Kg water) was added to the reaction mixture and the lower layer discarded. The organic layer was washed with additional water (5.07 L), the phases separated and the toluene was removed by vacuum distillation and replaced with propionic acid (20.42 Kg). The solution was further concentrated until less than 0.1 percent toluene remains. Additional propionic acid (6.17 Kg), H2O (12.3 L) and 48percent HBr (19.9 Kg) were added followed by 30percent H2O2 added over 1 h while maintaining the internal temperature between 50-60° C. The reaction was stirred for 1 h a the addition was complete then the temperature was raised to 80° C. for one additional hour. The reaction was quenched with sodium sulfite solution (2 Kg Na2SO3 and 19.3 Kg of H2O) followed by an additional H2O (72 L). The resulting mixture was aged overnight at 20° C. then filtered to give to afford 28.6 Kg (82percent yield for the 3 steps) of 2b.
Reference: [1] Patent: US2007/232810, 2007, A1, . Location in patent: Page/Page column 6-7
  • 3
  • [ 6683-48-3 ]
  • [ 119999-22-3 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3368 - 3383
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8432 - 8454
[4] Journal of Medicinal Chemistry, 1989, vol. 32, # 7, p. 1504 - 1517
[5] Patent: US8293803, 2012, B2,
[6] Patent: WO2013/40227, 2013, A2, . Location in patent: Page/Page column 36
  • 4
  • [ 6223-78-5 ]
  • [ 119999-22-3 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782
[2] Patent: US5716624, 1998, A,
[3] Patent: US8293803, 2012, B2,
  • 5
  • [ 6223-78-5 ]
  • [ 95-46-5 ]
  • [ 107-06-2 ]
  • [ 119999-22-3 ]
Reference: [1] Patent: US6316009, 2001, B1,
  • 6
  • [ 110-03-2 ]
  • [ 119999-22-3 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782
[2] Patent: US8293803, 2012, B2,
[3] Chemistry - A European Journal, 2013, vol. 19, # 10, p. 3504 - 3511
[4] Tetrahedron Letters, 2017, vol. 58, # 50, p. 4703 - 4708
  • 7
  • [ 116233-16-0 ]
  • [ 119999-22-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 7, p. 1504 - 1517
  • 8
  • [ 116233-17-1 ]
  • [ 119999-22-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 7, p. 1504 - 1517
  • 9
  • [ 119999-22-3 ]
  • [ 153559-49-0 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782
[2] Chemistry - A European Journal, 2013, vol. 19, # 10, p. 3504 - 3511
  • 10
  • [ 119999-22-3 ]
  • [ 153559-48-9 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782
  • 11
  • [ 119999-22-3 ]
  • [ 169126-64-1 ]
YieldReaction ConditionsOperation in experiment
0.8838 mg
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667 h; Inert atmosphere
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 3.33333 h; Inert atmosphere
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane for 2 h;
The method of Faul et al. was used. To a 100 mL round bottom flask containing THF (30 mL) was added a 1.6 M solution of «-BuLi in hexanes (8.0 mL, 12.8 mmol), and the resulting solution was cooled in a dry-ice acetone bath to -78 °C with stirring, under nitrogen. To this solution was added a solution of the 2:1 mixture of 32:12 (3.3587 g, 7.88 mmol) in THF (8 mL) over 20 min and the reaction was stirred at -78 °C for 10 min, and a mixture of triisopropylborate (4.9 mL, 21.3 mmol) in THF (10 mL) was added dropwise over 20 min. The reaction was stirred at -78 °C for 1 h and then warmed to room temperature and stirred for 2 h. The reaction was then quenched with 3 N HC1 (35 mL), and after stirring for 2 h, it was poured into ethyl acetate, the layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to give a crude product that was purified by column chromatography (150 mL Si02, ethyl acetate:hexanes 1 :3) to give 33 (0.8838 g, 45percent) as a white crystalline solid: 1H NMR (400 MHz, CDC13) ? 8.29 (s, 1H), 7.21 (s, 1H), 2.82 (s, 3H), 1.72 (s, 4H), 1.34 (s, 6H), 1.33 (s, 6H); 13C NMR (100.6 MHz, CDC13) ? 149.4, 142.8, 141.4, 136.3, 128.5, 35.1, 35.0, 34.3, 33.8, 31.8, 31.5, 22.6.
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 17, p. 5772 - 5782
[2] Patent: US6147255, 2000, A,
[3] Patent: WO2013/40227, 2013, A2, . Location in patent: Page/Page column 37
  • 12
  • [ 13780-71-7 ]
  • [ 121-43-7 ]
  • [ 119999-22-3 ]
  • [ 169126-64-1 ]
Reference: [1] Patent: US6147255, 2000, A,
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