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[ CAS No. 21524-34-5 ] {[proInfo.proName]}

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Chemical Structure| 21524-34-5
Chemical Structure| 21524-34-5
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Product Details of [ 21524-34-5 ]

CAS No. :21524-34-5 MDL No. :MFCD00051547
Formula : C15H23Br Boiling Point : -
Linear Structure Formula :- InChI Key :FUMMYHVKFAHQST-UHFFFAOYSA-N
M.W : 283.25 Pubchem ID :140846
Synonyms :

Calculated chemistry of [ 21524-34-5 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.6
Num. rotatable bonds : 3
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 77.88
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 : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.81
Log Po/w (XLOGP3) : 5.99
Log Po/w (WLOGP) : 5.82
Log Po/w (MLOGP) : 5.57
Log Po/w (SILICOS-IT) : 5.63
Consensus Log Po/w : 5.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.45
Solubility : 0.00101 mg/ml ; 0.00000355 mol/l
Class : Moderately soluble
Log S (Ali) : -5.77
Solubility : 0.000484 mg/ml ; 0.00000171 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.71
Solubility : 0.000547 mg/ml ; 0.00000193 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.98

Safety of [ 21524-34-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21524-34-5 ]

* 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 [ 21524-34-5 ]
  • Downstream synthetic route of [ 21524-34-5 ]

[ 21524-34-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 717-74-8 ]
  • [ 21524-34-5 ]
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 8, p. 2883 - 2889
[2] Journal of Organic Chemistry, 1999, vol. 64, # 8, p. 2883 - 2889
[3] Synlett, 1998, # 3, p. 286 - 288
[4] Journal of Organometallic Chemistry, 1997, vol. 532, # 1-2, p. 109 - 116
[5] Journal of the American Chemical Society, 1940, vol. 62, p. 2962
[6] Journal of the American Chemical Society, 1943, vol. 65, p. 2444
[7] Journal of the American Chemical Society, 1974, vol. 96, # 17, p. 5398 - 5407
[8] Journal of the American Chemical Society, 1976, vol. 98, p. 1860 - 1865
[9] Liebigs Annalen der Chemie, 1981, # 7, p. 1190 - 1197
[10] Angewandte Chemie - International Edition, 2013, vol. 52, # 35, p. 9266 - 9270[11] Angew. Chem., 2013, vol. 125, # 35, p. 9436 - 9440
  • 2
  • [ 148163-04-6 ]
  • [ 2344-22-1 ]
  • [ 21524-34-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 4, p. 395 - 396
  • 3
  • [ 71-43-2 ]
  • [ 21524-34-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 35, p. 9266 - 9270[2] Angew. Chem., 2013, vol. 125, # 35, p. 9436 - 9440
  • 4
  • [ 21524-34-5 ]
  • [ 154549-38-9 ]
Reference: [1] Tetrahedron, 2000, vol. 56, # 49, p. 9655 - 9662
  • 5
  • [ 13716-10-4 ]
  • [ 694-80-4 ]
  • [ 21524-34-5 ]
  • [ 564483-19-8 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With magnesium In tetrahydrofuran for 2 h; Inert atmosphere; Reflux
Stage #2: With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 5.5 h; Reflux; Inert atmosphere
1L three bottles,To a solution of 32.5 g of 2,4,6-triisopropylbromobenzene,5.6 g of magnesium turnings and 300 mL of anhydrous THF,20 g of o-chlorobromobenzene was dropwise added,2,4,6-triisopropyl-2-bromobiphenyl Grignard reagent,Refluxed for 2 hours,Down to room temperature,2.4 g of tetrakis (triphenylphosphine) palladium was added,Stirred for 30 minutes,18.8 g of di-tert-butylphosphonium chloride was added dropwise at room temperature,The reaction was refluxed for 5 hours.And the mixture was added dropwise to the reaction solution under ice-water bath200 mL of saturated aqueous ammonium chloride was quenched,Liquid separation,The organic phase is dissolved,Add methanol crystallization,And filtered to obtain 41.7 g of white 2-di-tert-butylphosphine-2,4,6-triisopropylbiphenyl,Yield 94percent.
Reference: [1] Patent: CN105859774, 2016, A, . Location in patent: Paragraph 0078; 0079; 0080; 0081
[2] Journal of the American Chemical Society, 2003, vol. 125, # 22, p. 6653 - 6655
  • 6
  • [ 21524-34-5 ]
  • [ 16523-54-9 ]
  • [ 583-53-9 ]
  • [ 564483-18-7 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With n-butyllithium In tetrahydrofuran at 0℃; for 1 h; Inert atmosphere
Stage #2: at 0℃; for 1 h; Inert atmosphere
Under the protection of nitrogen, 200 ml of THF and 31g of 2, 4, 6-tri-isopropyl-bromobenzene was added to 1L three-mouth bottle. The temperature was cooled down to 0 °C, and 46 ml of 2.5M n-butyl lithiumwas added dropwise. The reaction was continued for 1 hour after the addition. At 0 °C, 24.6g O-dibromobenzene was added dropwise. The reaction was continued for 1 hour after the addition. At0 °C, 42 ml of 2.5M n-butyl lithiumwas added dropwise to the reaction liquid.After the addition, the reaction was continued for 1 hour. 26.7g of dicyclohexyl phosphine was added dropwise, and the temperature was naturally warmed to react at room temperature for 2 hours. 200 ml saturated ammonium chloride aqueous solution was added dropwsie to the reaction liquid under the ice bath to quench the reaction. After phase separation, the organic phase was precipitated, and methanol was added for crystallization. Byfiltering, 44.5g white product of 2’-dicyclohexyl phosphino-2, 4, 6-tri-isopropyl biphenyl was obtained, with a yield of 89percent.
Reference: [1] Patent: CN105273006, 2016, A, . Location in patent: Paragraph 0069; 0070
  • 7
  • [ 694-80-4 ]
  • [ 21524-34-5 ]
  • [ 16523-54-9 ]
  • [ 564483-18-7 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 22, p. 6653 - 6655
[2] Chemistry - A European Journal, 2011, vol. 17, # 39, p. 10828 - 10831
[3] Organic Process Research and Development, 2004, vol. 8, # 6, p. 1065 - 1071
  • 8
  • [ 694-80-4 ]
  • [ 21524-34-5 ]
  • [ 100384-03-0 ]
  • [ 564483-18-7 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 39, p. 10828 - 10831
  • 9
  • [ 13716-10-4 ]
  • [ 21524-34-5 ]
  • [ 82830-49-7 ]
  • [ 1160861-53-9 ]
YieldReaction ConditionsOperation in experiment
18%
Stage #1: With magnesium; ethylene dibromide In tetrahydrofuranInert atmosphere; Reflux
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere
Stage #3: With copper(l) chloride In tetrahydrofuran; hexane at 20 - 75℃; for 48 h;
EXAMPLE THREE: Synthesis of Ligand 6; An oven-dried three-neck 100 rnL round bottom flask, which was equipped with a magnetic stir bar and charged with Magnesium shavings (360 mg, 15.36 mmol), was fitted with a reflux condenser, glass stopper, and rubber septum. The flask was evacuated and backfilled with argon (this process was repeated a total of 3 times) and then THF (40 mL) and 2,4,6-triisopropylbromobenzene (3.62 g, 12.8 mmol) were added via syringe. The reaction was heated to reflux and 1 ,2-dibromethane (40 μL) was added dropwise. The reaction was allowed to stir at reflux for 1 h and then was cooled to room temperature. A separate oven-dried 500 mL round bottom schlenk flask, which was equipped with a magnetic stir bar and fitted with a septum, was evacuated and backfilled with argon (this process was repeated a total of 3 times) and then THF (160 mL) and 1 ,4-dimethoxy-2- fluorobenzene (2 g, 12.8 mmol) were added to the flask via syringe. The reaction was cooled to -78 0C and n-BuLi (2.5 M in Hexane, 5.12 mL, 12.8 mmol) was added dropwise over a 15 min period. The solution was stirred for 30 min and the Grignard reagent, which was prepared in the first reaction vessel, was added via cannula transfer over a 20 min period and allowed to stir at -78 0C for 1 h. The reaction was warmed to room temperature slowly where it was stirred for an additional 3 h. Under a constant flow of argon the septum was removed and anhydrous CuCl (1.267 g, 12.8 mmol) was added quickly. The ClP(t-Bu)2 (2.44 mL, 12.8 mmol) was then added via syringe and the schlenk tube was sealed with a Teflon screw cap. The reaction was heated to 75 0C for 48 h and then cooled to room temperature. The reaction was quenched with 30percent aqueous NH4OH (100 mL) and the resulting suspension was extracted with EtOAc (200 mL). The organic layer was washed with 30percent aqueous NH4OH (3 x 100 mL) and brine (100 mL), dried over MgSO4, filtered, and concentrated on a rotary evaporator to yield a thick yellow oil. The crude material was taken up in minimum amount of hot MeOH and placed in a -25 0C freezer over night to yield 1.11 g (18percent) of white crystals.
Reference: [1] Patent: WO2009/76622, 2009, A2, . Location in patent: Page/Page column 116
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