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[ CAS No. 23450-18-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 23450-18-2
Chemical Structure| 23450-18-2
Structure of 23450-18-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 23450-18-2 ]

CAS No. :23450-18-2 MDL No. :MFCD00079713
Formula : C13H11Br Boiling Point : -
Linear Structure Formula :- InChI Key :DLCYFIIONMLNAJ-UHFFFAOYSA-N
M.W : 247.13 Pubchem ID :13061
Synonyms :

Calculated chemistry of [ 23450-18-2 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 63.6
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.84
Log Po/w (XLOGP3) : 4.53
Log Po/w (WLOGP) : 4.04
Log Po/w (MLOGP) : 4.81
Log Po/w (SILICOS-IT) : 4.57
Consensus Log Po/w : 4.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.73
Solubility : 0.00462 mg/ml ; 0.0000187 mol/l
Class : Moderately soluble
Log S (Ali) : -4.25
Solubility : 0.0138 mg/ml ; 0.000056 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.18
Solubility : 0.000165 mg/ml ; 0.000000667 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.85

Safety of [ 23450-18-2 ]

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

Application In Synthesis of [ 23450-18-2 ]

* 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 [ 23450-18-2 ]
  • Downstream synthetic route of [ 23450-18-2 ]

[ 23450-18-2 ] Synthesis Path-Upstream   1~31

  • 1
  • [ 23450-18-2 ]
  • [ 13047-06-8 ]
YieldReaction ConditionsOperation in experiment
91% With N-Bromosuccinimide; water In chloroform for 3 h; Reflux General procedure: In around-bottom flask, diarylmethanes (1.0 mmol), NBS (889.9 mg, 5.0 mmol) andwater (0 or 5.0 mmol) were dissolved in CHCl3 (4.0 mL). After refluxing for 3 h in the air, the reaction mixture was quenched withNa2S2O3·5H2O, cooled to roomtemperature, washed with 5mL CH2Cl2, dried with MgSO4,and filtered to get clear organic solution. The solvent was removed reduced pressure by a rotary evaporator, and the resulting residue was subjected to column chromatography on silica gel using co-solvent(ethyl acetate / petroleum ether, v/v) as eluent to give the corresponding diaryllketones.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 32, p. 4458 - 4462
  • 2
  • [ 13047-06-8 ]
  • [ 23450-18-2 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 7, p. 2000 - 2002
[2] Journal of Organic Chemistry, 1948, vol. 13, p. 786,788
[3] Journal of Organic Chemistry, 1937, vol. 2, p. 139,143
[4] Journal of the American Chemical Society, 1930, vol. 52, p. 2881,2887
[5] Journal of Organic Chemistry, 1939, vol. 4, p. 1,9
[6] Justus Liebigs Annalen der Chemie, 1939, vol. 540, p. 83,96
[7] Journal of Medicinal Chemistry, 1979, vol. 22, p. 1347 - 1354
[8] Journal of the Chemical Society, 1961, p. 1405 - 1407
[9] Advanced Synthesis and Catalysis, 2018, vol. 360, # 13, p. 2522 - 2536
  • 3
  • [ 18982-54-2 ]
  • [ 23450-18-2 ]
YieldReaction ConditionsOperation in experiment
55% With iron(III) chloride In benzene for 12 h; Reflux Benzene (20 mL) was added slowly to 2-bromobenzyl alcohol (8.0 g,42 mmol) and FeCl3 (3.2 g, 20 mmol), then the mixture was heated atreflux for 12 h. Once cooled to r.t., the solvent was removed under reducedpressure and the residual solid purified by column chromatography(eluent: pentane) affording 3a as a white solid; yield: 4.67 g(55percent).1H NMR (400 MHz, CDCl3): δ = 7.59 (dd, J = 8.0, 1.2 Hz, 2 H, ArH), 7.32(t, J = 7.6 Hz, 2 H, ArH), 7.26–7.21 (m, 4 H, ArH), 7.16 (dd, J = 7.6, 1.7Hz, 1 H, ArH), 7.10 (td, J = 8.0, 1.7 Hz, 1 H, ArH), 4.14 (s, 2 H, ArCH2).13C NMR (100 MHz, CDCl3): δ = 41.6, 124.9, 126.2, 127.4, 127.8, 128.5,129.0, 131.0, 132.8, 139.9, 140.4.
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 12, p. 1761 - 1765
[2] Synlett, 2006, # 11, p. 1729 - 1733
[3] Synthesis (Germany), 2015, vol. 47, # 12, p. 1761 - 1765
  • 4
  • [ 59142-47-1 ]
  • [ 23450-18-2 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 63, p. 16895 - 16901
[2] Journal of the American Chemical Society, 2017, vol. 139, # 1, p. 245 - 254
[3] New Journal of Chemistry, 2016, vol. 40, # 11, p. 9030 - 9033
[4] RSC Advances, 2015, vol. 5, # 104, p. 85291 - 85295
[5] European Journal of Medicinal Chemistry, 2000, vol. 35, # 1, p. 41 - 52
[6] Tetrahedron Letters, 2015, vol. 56, # 50, p. 7005 - 7007
  • 5
  • [ 71-43-2 ]
  • [ 3433-80-5 ]
  • [ 23450-18-2 ]
Reference: [1] Journal of Materials Chemistry, 2004, vol. 14, # 8, p. 1342 - 1346
[2] Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4532 - 4544
[3] Organic Letters, 2011, vol. 13, # 20, p. 5628 - 5631
[4] Chemische Berichte, 1992, vol. 125, # 4, p. 941 - 950
[5] Chemical Communications, 2016, vol. 52, # 44, p. 7138 - 7141
[6] Journal of the American Chemical Society, 2017, vol. 139, # 45, p. 16210 - 16221
  • 6
  • [ 18982-54-2 ]
  • [ 71-43-2 ]
  • [ 23450-18-2 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 9, p. 3289 - 3292
[2] Angewandte Chemie - International Edition, 2012, vol. 51, # 12, p. 2939 - 2942
[3] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6997 - 7005
[4] Organic Letters, 2013, vol. 15, # 21, p. 5542 - 5545
[5] Tetrahedron Letters, 2014, vol. 55, # 32, p. 4458 - 4462
  • 7
  • [ 5467-74-3 ]
  • [ 100-44-7 ]
  • [ 2116-36-1 ]
  • [ 23450-18-2 ]
YieldReaction ConditionsOperation in experiment
63% at 100℃; for 24 h; Sealed tube To a 10 mL reaction tube containing a magnet was added (4-bromophenyl) boronic acid (201 mg, 1.0 mmol)Lithium tert-butoxide (80 mg, 1.0 mmol).Trifluorotoluene (2 mL) and benzyl chloride (63 mg, 0.5 mmol) were added.Stuffed rubber stopper,The reaction was performed on a 100 ° C electromagnetic heating stirrer for about 24 hours.After the reaction,Cool to room temperature,The organic solvent is removed using a rotary evaporator,And purified by column chromatography to give 1-benzyl-4-bromobenzeneAnd 1-benzyl-2-bromobenzene (82 mg, 63percent).The compound is a colorless oily liquid,
88.889 % de
Stage #1: Schlenk technique; Inert atmosphere
Stage #2: at 100℃; for 24 h; Schlenk technique; Inert atmosphere
General procedure: Arylboronic acid (1.0 mmol), LiOtBu (1.0 mmol) was added to a Schlenk tube. The tube was charged with nitrogen and then PhCF3 (2 mL) and benzyl chloride (0.5 mmol) were added. The reaction mixture was stirred at 100 °C for 24 h. After the mixture was cooled down to room temperature, solvent was removed under reduced pressure to leave a crude product. The crude product was purified by column chromatography on silica gel, eluting with petroleum ether to afford the coupling product.
Reference: [1] Patent: CN106478326, 2017, A, . Location in patent: Paragraph 0098; 0099; 0100; 0101; 0102
[2] Tetrahedron, 2016, vol. 72, # 49, p. 8022 - 8030
  • 8
  • [ 108-86-1 ]
  • [ 100-44-7 ]
  • [ 2116-36-1 ]
  • [ 23450-18-2 ]
Reference: [1] Transition Metal Chemistry, 2016, vol. 41, # 2, p. 225 - 233
  • 9
  • [ 98-80-6 ]
  • [ 3433-80-5 ]
  • [ 23450-18-2 ]
Reference: [1] Patent: US2018/305381, 2018, A1,
  • 10
  • [ 6630-33-7 ]
  • [ 23450-18-2 ]
Reference: [1] Tetrahedron, 1976, vol. 32, p. 1921 - 1930
[2] Organic Letters, 2013, vol. 15, # 21, p. 5542 - 5545
[3] Tetrahedron Letters, 2014, vol. 55, # 32, p. 4458 - 4462
[4] Tetrahedron Letters, 2015, vol. 56, # 50, p. 7005 - 7007
[5] New Journal of Chemistry, 2016, vol. 40, # 11, p. 9030 - 9033
[6] Journal of the American Chemical Society, 2017, vol. 139, # 1, p. 245 - 254
[7] Chemistry - A European Journal, 2018, vol. 24, # 63, p. 16895 - 16901
  • 11
  • [ 911707-65-8 ]
  • [ 71-43-2 ]
  • [ 23450-18-2 ]
Reference: [1] Synlett, 2006, # 11, p. 1729 - 1733
  • 12
  • [ 1078-58-6 ]
  • [ 3433-80-5 ]
  • [ 23450-18-2 ]
Reference: [1] Dalton Transactions, 2015, vol. 44, # 27, p. 12189 - 12195
  • 13
  • [ 3433-80-5 ]
  • [ 23450-18-2 ]
  • [ 606-97-3 ]
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 12, p. 1761 - 1765
  • 14
  • [ 392-83-6 ]
  • [ 71-43-2 ]
  • [ 23450-18-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1417 - 1421[2] Angew. Chem., 2016, vol. 55, # 4, p. 1439 - 1443,5
  • 15
  • [ 108-86-1 ]
  • [ 23450-18-2 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 50, p. 7005 - 7007
[2] New Journal of Chemistry, 2016, vol. 40, # 11, p. 9030 - 9033
[3] Journal of the American Chemical Society, 2017, vol. 139, # 1, p. 245 - 254
[4] Chemistry - A European Journal, 2018, vol. 24, # 63, p. 16895 - 16901
  • 16
  • [ 62673-31-8 ]
  • [ 583-53-9 ]
  • [ 792-68-7 ]
  • [ 23450-18-2 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, p. 845 - 848
  • 17
  • [ 578-51-8 ]
  • [ 23450-18-2 ]
  • [ 606-97-3 ]
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 12, p. 1761 - 1765
  • 18
  • [ 108-86-1 ]
  • [ 100-52-7 ]
  • [ 2116-36-1 ]
  • [ 23450-18-2 ]
  • [ 27798-39-6 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 35, p. 6291 - 6294
  • 19
  • [ 100-58-3 ]
  • [ 3433-80-5 ]
  • [ 23450-18-2 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 81, p. 12109 - 12111
  • 20
  • [ 61593-14-4 ]
  • [ 23450-18-2 ]
Reference: [1] Tetrahedron, 1976, vol. 32, p. 1921 - 1930
  • 21
  • [ 61593-04-2 ]
  • [ 23450-18-2 ]
Reference: [1] Tetrahedron, 1976, vol. 32, p. 1921 - 1930
  • 22
  • [ 6921-34-2 ]
  • [ 583-53-9 ]
  • [ 23450-18-2 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, p. 845 - 848
  • 23
  • [ 108-86-1 ]
  • [ 103-50-4 ]
  • [ 2116-36-1 ]
  • [ 23450-18-2 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 37, p. 9146 - 9152
  • 24
  • [ 108-86-1 ]
  • [ 100-51-6 ]
  • [ 2116-36-1 ]
  • [ 23450-18-2 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 41, p. 10185 - 10188
  • 25
  • [ 108-86-1 ]
  • [ 65-85-0 ]
  • [ 2116-36-1 ]
  • [ 23450-18-2 ]
Reference: [1] European Journal of Organic Chemistry, 2011, # 17, p. 3178 - 3183
  • 26
  • [ 100-58-3 ]
  • [ 23450-18-2 ]
Reference: [1] Dalton Transactions, 2015, vol. 44, # 27, p. 12189 - 12195
  • 27
  • [ 61593-05-3 ]
  • [ 23450-18-2 ]
Reference: [1] Tetrahedron, 1976, vol. 32, p. 1921 - 1930
  • 28
  • [ 108-86-1 ]
  • [ 2116-36-1 ]
  • [ 23450-18-2 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 46, p. 8097 - 8100
  • 29
  • [ 6630-33-7 ]
  • [ 23450-18-2 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, p. 2091 - 2094
  • 30
  • [ 23450-18-2 ]
  • [ 40276-63-9 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4532 - 4544
[2] Journal of the American Chemical Society, 2017, vol. 139, # 45, p. 16210 - 16221
  • 31
  • [ 121-43-7 ]
  • [ 23450-18-2 ]
  • [ 40276-63-9 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 44, p. 7138 - 7141
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