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[ CAS No. 4209-02-3 ] {[proInfo.proName]}

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Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
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3d Animation Molecule Structure of 4209-02-3
Chemical Structure| 4209-02-3
Chemical Structure| 4209-02-3
Structure of 4209-02-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4209-02-3 ]

CAS No. :4209-02-3 MDL No. :MFCD00095178
Formula : C8H6BrClO Boiling Point : -
Linear Structure Formula :- InChI Key :HCQNNQFCUAGJBD-UHFFFAOYSA-N
M.W : 233.49 Pubchem ID :77882
Synonyms :

Calculated chemistry of [ 4209-02-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.13
TPSA : 17.07 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) : -5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 3.05
Log Po/w (WLOGP) : 2.87
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 3.33
Consensus Log Po/w : 2.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.48
Solubility : 0.0772 mg/ml ; 0.000331 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.197 mg/ml ; 0.000842 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.23
Solubility : 0.0139 mg/ml ; 0.0000594 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 4209-02-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4209-02-3 ]

* 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 [ 4209-02-3 ]
  • Downstream synthetic route of [ 4209-02-3 ]

[ 4209-02-3 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 99-90-1 ]
  • [ 4209-02-3 ]
YieldReaction ConditionsOperation in experiment
50.3% With sulfuryl dichloride In methyl t-butyl ether at 20℃; for 1 h; [0371] [TABLE-US-00002] (18) acetophenone derivative R13 R14 1 NO2 H 2 NO2 Cl 3 H Br 4 H H [0372] An acetophenone (2.00 g) as shown by the formula (18) was dissolved or suspended in a solvent as shown in Table 2 (M representing the molarity based on the acetophenone derivative), and sulfuryl chloride in an amount as shown in Table 2 was added all at once under stirring. The temperature and reaction time were as shown in Table 2. [TABLE-US-00003] TABLE 2 Acetophenone SO2Cl2 Time Yield Ex. Solvent (M) derivative (equivalent) Temp. (hr) (percent) 42 MTBE(0.5) 1 3.0 r.t. 4.5 50.8 43 MTBE(1) 1 1.65 reflux 7.0 70.1 44 IPE(1) 1 3.0 r.t. 3.0 77.8 45 DME(1) 1 1.65 r.t. 4.0 71.4 46 MTBE(1) 3 3.0 r.t. 1.0 50.3 47 MTBE(1) 4 1.1 r.t. 7.0 78.9 MTBE: methyl t-butyl ether; IPE: diisopropyl ether; DME: 1,2-dimethoxyethane
35% With Oxone; ammonium chloride In methanol at 20℃; for 24 h; General procedure: A typical procedure for the α-chlorination of ketone:acetophenone 1a (0.5 mmol), Oxone® (0.6 mmol) and NH4Cl (1.0 mmol) were added in MeOH (2 mL). The mixture was stirred at room temperature for 24 h and then separated on a silica gel plate using (4:1 hexane-ethyl acetate) as eluant to give α-chloroacetophenone 2a in 85percent of yield. White solid, mp 52–54 °C; 1H NMR (500 MHz, CDCl3): δ 7.97 (d, 2 H, J = 8.4 Hz), 7.64–7.61 (m, 1H), 7.53–7.50 (m, 2H), 4.73 (s, 2H); 13C NMR (125 MHz, CDCl3): δ 193.35, 137.53, 134.46, 128.75, 127.13, 48.14.
Reference: [1] Synthesis, 1988, # 7, p. 545 - 546
[2] Synthetic Communications, 2006, vol. 36, # 2, p. 255 - 258
[3] Green Chemistry, 2009, vol. 11, # 2, p. 275 - 278
[4] Synthetic Communications, 2011, vol. 41, # 10, p. 1508 - 1513
[5] Tetrahedron Letters, 2004, vol. 45, # 1, p. 191 - 193
[6] European Journal of Organic Chemistry, 2017, vol. 2017, # 43, p. 6390 - 6400
[7] Synthetic Communications, 2006, vol. 36, # 6, p. 777 - 780
[8] Advanced Synthesis and Catalysis, 2017, vol. 359, # 23, p. 4177 - 4183
[9] Patent: US2003/225289, 2003, A1, . Location in patent: Page 28
[10] Chinese Chemical Letters, 2012, vol. 23, # 11, p. 1213 - 1216,4
[11] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1985, vol. 24, # 4, p. 300 - 303
[12] Journal of the American Chemical Society, 1952, vol. 74, p. 3333,3337
[13] Magnetic Resonance in Chemistry, 1987, vol. 25, p. 179 - 180
[14] Bulletin des Societes Chimiques Belges, 1964, vol. 73, p. 579 - 584
[15] Chemistry Letters, 2012, vol. 41, # 4, p. 432 - 434
[16] Tetrahedron, 2013, vol. 69, # 31, p. 6392 - 6398
[17] Organic and Biomolecular Chemistry, 2016, vol. 14, # 17, p. 4129 - 4135
[18] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2119 - 2124
  • 2
  • [ 108-86-1 ]
  • [ 79-04-9 ]
  • [ 4209-02-3 ]
Reference: [1] MedChemComm, 2013, vol. 4, # 9, p. 1267 - 1274
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1897, vol. 125, p. 718
[3] Chemical and Pharmaceutical Bulletin, 1977, vol. 25, p. 3370 - 3375
[4] Synthetic Communications, 2000, vol. 30, # 15, p. 2763 - 2768
[5] Tetrahedron Asymmetry, 2003, vol. 14, # 24, p. 3861 - 3866
[6] Patent: WO2008/124000, 2008, A2, . Location in patent: Page/Page column 81; 118
  • 3
  • [ 41262-33-3 ]
  • [ 4209-02-3 ]
  • [ 881650-48-2 ]
YieldReaction ConditionsOperation in experiment
55% With [2,2]bipyridinyl; copper(l) chloride In 1,2-dichloro-ethane; benzene for 1.5 h; Inert atmosphere; Schlenk technique; Reflux General procedure: A two-neck round bottom flask fitted with a rubber septum was connected to a Schlenk tube through a condenser. The flask was evacuated and dried by heating with a flame while the vacuum pump was turned on, and then the flask was filled with dry nitrogen. After removing the rubber septum, it was charged with CuCl (800 mg, 8 mmol), 2,2’-bipyridyl (1.248 gm, 8 mmol), and a magnetic bar under continuous flow of nitrogen. The rubber septum was then restored and the flask was evacuated and filled with nitrogen. Dry Benzene (10 ml) was then injected into the flask to ensure the formation of the brown colored copper-bpy complex. Now the solution of 2,2,2-trichloro-1-phenylethanone 1 (4 mmol) in DCE (10 ml) was injected through the septum. The flask was again evacuated and filled with nitrogen after cooling it in an ice bath. The ice bath was removed and the reaction mixture was heated at reflux with stirring under a slow and continuous flow of nitrogen. The progress of the reaction was monitored at regular 30 min. intervals of time by taking the sample of the reaction mixture with a syringe. The initial brown color of the reaction mixture faded as the reaction progresses. After the completion of the reaction as indicated by TLC, the greenish reaction mixture was cooled and filtered through a celite pad. The insoluble green solid on the celite pad was washed thoroughly with chloroform and the light brown filtrate was evaporated under reduced pressure on a rotary evaporator. The residual mass was subjected to column chromatography using silica gel as the solid support and n-hexane and its mixture with ethyl acetate as the solvent for elution to get pure products in 45-70 percent yield. The products were characterized by spectroscopic analysis, melting point and by comparing with authentic values.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 22, p. 2437 - 2440
  • 4
  • [ 51556-09-3 ]
  • [ 4209-02-3 ]
Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 116 - 121
[2] Chinese Journal of Chemistry, 2016, vol. 34, # 12, p. 1251 - 1254
  • 5
  • [ 5391-88-8 ]
  • [ 4209-02-3 ]
Reference: [1] Chemistry Letters, 1990, # 7, p. 1125 - 1128
  • 6
  • [ 81585-72-0 ]
  • [ 4209-02-3 ]
Reference: [1] Tetrahedron, 2013, vol. 69, # 31, p. 6392 - 6398
  • 7
  • [ 99-90-1 ]
  • [ 7716-86-1 ]
  • [ 4209-02-3 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 23, p. 4177 - 4183
[2] Journal of the Chinese Chemical Society (Taipei, Taiwan), 1997, vol. 44, # 3, p. 309 - 312
  • 8
  • [ 21757-86-8 ]
  • [ 4209-02-3 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 14, p. 5633 - 5635
  • 9
  • [ 80-11-5 ]
  • [ 586-75-4 ]
  • [ 4209-02-3 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 14, p. 5814 - 5823
  • 10
  • [ 99-73-0 ]
  • [ 4209-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1943, vol. 65, p. 2096
[2] Journal of the American Chemical Society, 1943, vol. 65, p. 2096
[3] Journal of Medicinal Chemistry, 1976, vol. 19, # 7, p. 928 - 933
[4] RSC Advances, 2016, vol. 6, # 30, p. 25339 - 25345
  • 11
  • [ 619-41-0 ]
  • [ 4209-02-3 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 52, p. 9359 - 9364
  • 12
  • [ 99-90-1 ]
  • [ 4209-02-3 ]
  • [ 403-30-5 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 46, p. 9550 - 9556
  • 13
  • [ 1122-91-4 ]
  • [ 4209-02-3 ]
  • [ 881650-48-2 ]
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 22, p. 2437 - 2440
  • 14
  • [ 21757-86-8 ]
  • [ 4209-02-3 ]
  • [ 881650-48-2 ]
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 22, p. 2437 - 2440
  • 15
  • [ 67-56-1 ]
  • [ 99-90-1 ]
  • [ 4209-02-3 ]
  • [ 1206904-21-3 ]
Reference: [1] Chemistry Letters, 2012, vol. 41, # 4, p. 432 - 434
  • 16
  • [ 94783-77-4 ]
  • [ 4209-02-3 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1964, vol. 73, p. 579 - 584
  • 17
  • [ 766-96-1 ]
  • [ 64-19-7 ]
  • [ 7716-86-1 ]
  • [ 4209-02-3 ]
  • [ 51556-09-3 ]
  • [ 99-90-1 ]
  • [ 84553-29-7 ]
  • [ 84553-24-2 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 34, p. 3483 - 3486
  • 18
  • [ 766-96-1 ]
  • [ 64-19-7 ]
  • [ 7716-86-1 ]
  • [ 4209-02-3 ]
  • [ 99-90-1 ]
  • [ 84553-24-2 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1983, # 9, p. 2127 - 2155
  • 19
  • [ 4209-02-3 ]
  • [ 92093-23-7 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 48, p. 8801 - 8805
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