Home Cart 0 Sign in  

[ CAS No. 189367-54-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 189367-54-2
Chemical Structure| 189367-54-2
Structure of 189367-54-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 189367-54-2 ]

Related Doc. of [ 189367-54-2 ]

Alternatived Products of [ 189367-54-2 ]

Product Details of [ 189367-54-2 ]

CAS No. :189367-54-2 MDL No. :MFCD03427215
Formula : C25H32Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :OXFFIMLCSVJMHA-UHFFFAOYSA-N
M.W : 492.33 Pubchem ID :3539647
Synonyms :

Calculated chemistry of [ 189367-54-2 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.52
Num. rotatable bonds : 10
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 127.86
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -1.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.63
Log Po/w (XLOGP3) : 11.22
Log Po/w (WLOGP) : 9.42
Log Po/w (MLOGP) : 7.68
Log Po/w (SILICOS-IT) : 9.72
Consensus Log Po/w : 8.74

Druglikeness

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

Water Solubility

Log S (ESOL) : -9.63
Solubility : 0.000000115 mg/ml ; 0.0000000002 mol/l
Class : Poorly soluble
Log S (Ali) : -11.19
Solubility : 0.0000000032 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -11.53
Solubility : 0.0000000014 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.63

Safety of [ 189367-54-2 ]

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 [ 189367-54-2 ]

* 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 [ 189367-54-2 ]
  • Downstream synthetic route of [ 189367-54-2 ]

[ 189367-54-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 111-25-1 ]
  • [ 16433-88-8 ]
  • [ 189367-54-2 ]
YieldReaction ConditionsOperation in experiment
86%
Stage #1: With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; dimethyl sulfoxide for 0.5 h;
Stage #2: at 20℃; for 3 h;
2,7-dibromo fluorene 1.5g, triethyl benzyl ammonium chloride 0.009g, 30mL dimethylSulfoxides discharge suspended in three flask, was added dropwise 1.5 mL of 50wtpercent aqueous sodium hydroxide,The reaction for half an hour, and then dropping 1.59g1- bromine hexane. The mixture was stirred at room temperature for 3 hours,Extracted with ether. The organic phase was washed with brine, dried over anhydrous magnesium sulfate. The solvent was distilled off, noRecrystallization from aqueous ethanol orange needle crystals of 2,7-dibromo-9,9-dihexylfluorene (fluorenyl Compound 2)1.96g, Yield: 86percent
84.36% With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 24 h; Inert atmosphere Dissolve hfluorene (5.00 g, 30.08 mmol) in 40 mL of chloroform solution.A solution of Br2 (3.08 mL) dissolved in 15 mL of chloroform was added dropwise to the above solution and stirred at 0°C for 10 hours in the dark.The reaction was stopped and the mixed solution was poured into an aqueous Na2S2O3 solution and extracted with dichloromethane (15 mL x 3).The combined organic layers were washed with deionized water (25 mL x 3) and saturated brine (20 mL), respectively.After that, the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was recrystallized from an absolute ethanol solution to give 2,7-dibromo-fluorene (7.04 g, 72.2percent) as a white solid;Then, 2,7-dibromo-fluorene (6.40 g, 19.75 mmol) obtained from the previous reaction was dissolved with tetrabutylammonium bromide (0.10 g, 0.31 mmol) and 1-bromohexane (7.30 mL, 44.24 mmol). In 60mL of tolueneAnd 25mL of 50percent water by mass of NaOH solution, and argon is kept at 80°C and stirred under reflux for 24 hours.Stop the reaction and extract the solution with ethyl acetate (25mL x 3). Combine the organic layers with deionized water (25mL x 3)After washing with saturated brine (30 mL), the organic layer was dried over anhydrous magnesium sulfate and the solvent was removed using a rotary evaporator.The crude product was separated on a chromatography column (petroleum ether:dichloromethane = 4:1) to give 2,7-dibromo-9,9-dihexyl-fluorene (8.20 g, 84.36percent) as a pale yellow solid;Finally, the resulting 2,7-dibromo-9,9-dihexyl-fluorene (1.00 g, 2.03 mmol) was reacted in the previous step.Dissolve in 30 mL of dichloromethane, add 5 mL of concentrated sulfuric acid, and cool to 0 °C.Ammonium cerium nitrate (3.34 g, 6.09 mmol) was added portionwise to the above mixed solution, and the reaction was stirred for 1 hour.Stop the reaction and add 30 mL of deionized water and extract with dichloromethane (15 mL × 3).The organic phase was washed with deionized water (15 mL x 3) and saturated brine (20 mL), respectively.The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the crude product was separated by a chromatography column (petroleum ether: dichloromethane=2:1) to give an orange-yellow product.2,7-dibromo-9,9-dihexyl-1,6-dinitro-fluorene (0.62 g, 52.54percent),
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 8, p. 2714 - 2717
[2] Macromolecules, 2003, vol. 36, # 19, p. 6995 - 7003
[3] Chemical Communications, 2008, # 32, p. 3765 - 3767
[4] Macromolecules, 2003, vol. 36, # 19, p. 6970 - 6975
[5] Tetrahedron Letters, 2007, vol. 48, # 1, p. 89 - 93
[6] Macromolecules, 2011, vol. 44, # 20, p. 7977 - 7986
[7] Dyes and Pigments, 2015, vol. 113, p. 682 - 691
[8] Macromolecules, 2003, vol. 36, # 18, p. 6704 - 6710
[9] Macromolecules, 2004, vol. 37, # 23, p. 8523 - 8529
[10] Chemical Communications, 2005, # 27, p. 3397 - 3399
[11] Tetrahedron Letters, 2010, vol. 51, # 9, p. 1317 - 1321
[12] Polymer, 2010, vol. 51, # 26, p. 6182 - 6192
[13] Chemical Communications, 2002, # 15, p. 1608 - 1609
[14] European Journal of Organic Chemistry, 2013, # 3, p. 498 - 508
[15] Patent: CN104774147, 2016, B, . Location in patent: Paragraph 0048; 0051
[16] Organic and Biomolecular Chemistry, 2003, vol. 1, # 17, p. 3069 - 3077
[17] Patent: CN107686448, 2018, A, . Location in patent: Paragraph 0018; 0020; 0021
[18] Chemistry - A European Journal, 2010, vol. 16, # 47, p. 14131 - 14141
[19] Macromolecules, 2015, vol. 48, # 19, p. 7007 - 7014
[20] Dalton Transactions, 2016, vol. 45, # 11, p. 4580 - 4587
[21] Chemistry - An Asian Journal, 2017, vol. 12, # 2, p. 181 - 189
[22] Journal of the American Chemical Society, 2005, vol. 127, # 33, p. 11763 - 11768
[23] Chemical Communications, 1999, # 18, p. 1837 - 1838
[24] Journal of Materials Chemistry, 2011, vol. 21, # 5, p. 1582 - 1592
[25] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 15, p. 3355 - 3365
[26] Journal of Physical Chemistry A: Molecules, Spectroscopy, Kinetics, Environment, and General Theory, 2012, vol. 116, # 37, p. 9305 - 9314,10
[27] Asian Journal of Chemistry, 2013, vol. 25, # 10, p. 5700 - 5702
[28] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 23, p. 4945 - 4956
[29] Journal of Materials Chemistry C, 2014, vol. 2, # 38, p. 8122 - 8130
[30] Patent: CN105503846, 2016, A, . Location in patent: Paragraph 0045; 0046; 0047; 0048
[31] Heterocyclic Communications, 2017, vol. 23, # 1, p. 15 - 21
[32] Patent: CN108815529, 2018, A, . Location in patent: Paragraph 0021; 0024-0025
  • 2
  • [ 123863-97-8 ]
  • [ 189367-54-2 ]
YieldReaction ConditionsOperation in experiment
98.2 %Turnov. With N-Bromosuccinimide In water at 55℃; for 19 h; A 250 ml flask equipped with a electric stirrer, nitrogen pad, thermowell, and heating mantle was wrapped in foil to minimize the introduction of light.It was loaded with 17.0 g (<=0.047 moles) crude 9,9-di-n-hexylfluorene from Example 1a, 21.1 g (0.119 moles) of N-bromosuccinimide (NBS), and 53.2 g of water.The system was heated to 55° C. for 19 hours where the conversion was determined to be 98.2percent (by area percent GC).Addition of 1.8 g (0.017 moles) NaHSO3 caused the color to change from red to yellow.The temperature was then increased to 65° C.
The phases were separated.The top aqueous phase was extracted with 1*8 g of toluene.The combined organic phases were mixed with 32 g of acetonitrile and heated to reflux.It was then cooled to 10° C. and filtered. Air-Drying yielded 19.9 g of a yellow solid, an 84.3percent isolated yield (based on fluorene).Analyzing the filtrate gave a total accountability based on fluorene of about 92percent.
Reference: [1] Journal of Materials Chemistry, 2002, vol. 12, # 4, p. 924 - 933
[2] Chemistry Letters, 2004, vol. 33, # 10, p. 1290 - 1291
[3] Patent: US2004/122266, 2004, A1, . Location in patent: Page 2
[4] Journal of Materials Chemistry, 2008, vol. 18, # 10, p. 1131 - 1138
  • 3
  • [ 86-73-7 ]
  • [ 189367-54-2 ]
Reference: [1] Chemical Communications, 2005, # 27, p. 3397 - 3399
[2] Chemistry Letters, 2004, vol. 33, # 10, p. 1290 - 1291
[3] Journal of Materials Chemistry, 2002, vol. 12, # 4, p. 924 - 933
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 15, p. 3355 - 3365
[5] European Journal of Organic Chemistry, 2013, # 3, p. 498 - 508
[6] Journal of Polymer Science, Part A: Polymer Chemistry, 2013, vol. 51, # 23, p. 4945 - 4956
[7] Dyes and Pigments, 2015, vol. 113, p. 682 - 691
[8] Journal of Materials Chemistry C, 2014, vol. 2, # 38, p. 8122 - 8130
[9] Patent: CN105503846, 2016, A,
[10] Patent: CN104774147, 2016, B,
[11] Heterocyclic Communications, 2017, vol. 23, # 1, p. 15 - 21
[12] Chemistry - An Asian Journal, 2017, vol. 12, # 2, p. 181 - 189
[13] Patent: CN107686448, 2018, A,
  • 4
  • [ 544-10-5 ]
  • [ 16433-88-8 ]
  • [ 189367-54-2 ]
YieldReaction ConditionsOperation in experiment
77.1 %Chromat. With sodium hydroxide; Aliquat 336 In water; toluene at 55 - 75℃; for 33.5 h; A mixture of 16.2 g (0.05 moles) dibromofluorene, 13.7 g (0.113 moles) chlorohexane, 0.9 g (0.002 moles) tricaprylmethylammonium chloride (commercially known as Aliquat 336) and 15 ml of toluene was heated to 55° C. under nitrogen. To this was shot added 60.1 g (0.76 moles) 50percent NaOH. No exotherm was detected. The system was heated at 55° C. for 3 hours, 65° C. for 19.5 hours, then 75° C. for 11 hours. At this point, a GC analysis indicated 98+percent conversion. The system was cooled to 60° C. The solids (NaCl) remained suspended in the top organic phase. The aqueous phase was separated and the organic phase was extracted with 1.x.18 ml water, keeping the system at about 60° C. This seemed to be enough water to dissolve all of the solids. The organic phase remained the top phase. The aqueous phase was separated and the organic phase extracted with 19 ml 3.5percent HCl. The organic phase now became the bottom phase and changed color from dark to green and then orange. The organic phase was separated off and product precipitated with of 30.6 g of acetonitrile. It was cooled to 10° C. and filtered. The cake was rinsed with 1.x.10 ml of acetonitrile and air-dried to 19.3 g of a pale yellow solid. By area percent GC it was 98.3percent 2,7-dibromo-9,9-di-n-hexylfluorene, a 77.1percent yield.
Reference: [1] Patent: US2004/122266, 2004, A1, . Location in patent: Page 2-3
  • 5
  • [ 111-25-1 ]
  • [ 16433-88-8 ]
  • [ 1112-67-0 ]
  • [ 189367-54-2 ]
Reference: [1] Patent: US2003/170490, 2003, A1,
  • 6
  • [ 111-25-1 ]
  • [ 189367-54-2 ]
Reference: [1] Chemistry Letters, 2004, vol. 33, # 10, p. 1290 - 1291
[2] Journal of Materials Chemistry, 2002, vol. 12, # 4, p. 924 - 933
Same Skeleton Products
Historical Records