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[ CAS No. 174265-12-4 ] {[proInfo.proName]}

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Chemical Structure| 174265-12-4
Chemical Structure| 174265-12-4
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Product Details of [ 174265-12-4 ]

CAS No. :174265-12-4 MDL No. :MFCD00462870
Formula : C7H4BrClO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 219.46 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 174265-12-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.54
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) : -5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 3.29
Log Po/w (WLOGP) : 2.92
Log Po/w (MLOGP) : 2.79
Log Po/w (SILICOS-IT) : 3.3
Consensus Log Po/w : 2.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.65
Solubility : 0.049 mg/ml ; 0.000223 mol/l
Class : Soluble
Log S (Ali) : -3.32
Solubility : 0.104 mg/ml ; 0.000475 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.82
Solubility : 0.0331 mg/ml ; 0.000151 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 174265-12-4 ]

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

Application In Synthesis of [ 174265-12-4 ]

* 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 [ 174265-12-4 ]
  • Downstream synthetic route of [ 174265-12-4 ]

[ 174265-12-4 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 174265-12-4 ]
  • [ 2999-46-4 ]
  • [ 4792-67-0 ]
Reference: [1] Chemical Communications, 2009, # 48, p. 7581 - 7583
  • 2
  • [ 174265-12-4 ]
  • [ 623-33-6 ]
  • [ 4792-67-0 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 511 - 514
[2] European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 511 - 514
  • 3
  • [ 174265-12-4 ]
  • [ 1906-82-7 ]
  • [ 4792-67-0 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6549 - 6551
[2] RSC Advances, 2017, vol. 7, # 23, p. 13754 - 13759
  • 4
  • [ 174265-12-4 ]
  • [ 14548-38-0 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 23, p. 6635 - 6637
  • 5
  • [ 174265-12-4 ]
  • [ 3970-52-3 ]
  • [ 3970-51-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 50, p. 16013 - 16017[2] Angew. Chem., 2017, vol. 129, p. 16229 - 16233,5
  • 6
  • [ 174265-12-4 ]
  • [ 935-99-9 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 22, p. 5566 - 5569
[2] Journal of the American Chemical Society, 2016, vol. 138, # 42, p. 13830 - 13833
[3] Tetrahedron Letters, 2017, vol. 58, # 4, p. 285 - 288
[4] Journal of Organic Chemistry, 2017, vol. 82, # 21, p. 11585 - 11593
[5] Chemistry - An Asian Journal, 2018, vol. 13, # 15, p. 1897 - 1901
  • 7
  • [ 174265-12-4 ]
  • [ 60666-70-8 ]
YieldReaction ConditionsOperation in experiment
100% With sodium tetrahydroborate In methanol at 0 - 20℃; for 1 h; Step 1: (2-Bromo-5-chlorophenyl)methanol
To a stirred suspension of 2-bromo-5-chlorobenzaldehyde (4.48 g, 20.4 mmol) in MeOH (50 mL) was added NaBH4(1.16 g, 30.7 mmol) at 0 °C. The reaction was stirred at 0 °C for 30 min, then allowed to warm to room temperature and stirred for an additional 30 min. TLC analysis indicated complete consumption of starting material. The solvent was removed and then NH4C1 (aq. satd., 30 mL) was added to quench the reaction. The mixture was extracted with CH2CI2(3x50 mL). The combined organic phases were washed with NaCl (aq. satd.,100 mL) and dried over Na2S04. The solvent was concentrated to yield the title compound as an oil (4.55 g, quant.) which was used in the next step without further purification.
1H NMR (500 MHz, acetone-6) δ ppm 4.64 (br. s, 1H), 4.65 (s, 2H), 7.24 (dd, J=8.4, 2.7 Hz, 1H), 7.56 (d, J=8.5 Hz, 1H), 7.62 (d, J=2.5 Hz, 1H)
95% With sodium hydride In methanol at 20℃; PREPARATION 172 (2-Bromo-5-chlorophenyl)methanol Sodium borohydride (0.17 g, 4.56 mmol) was suspended in 15 ml methanol. 2-Bromo- 5-chlorobenzaldehyde (1 g, 4.56 mmol) dissolved in 10 ml methanol was added drop- wise and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was re-dissolved in ethyl acetate. The organics were washed sequentially with water and brine. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure to give 0.97 g (4.34 mmol, 95percent) of the title compound as a white solid. Purity 99percent. 1 H NMR (400 MHz, CHLOROFORM-d) δ ppm 1 .98 (t, J=5.67 Hz, 1 H), 4.73 (d, J=5.47 Hz, 2 H), 7.15 (dd, J=8.60, 2.74 Hz, 1 H), 7.47 (d, J=8.60 Hz, 1 H), 7.53 (d, J=2.34 Hz, 1 H). UPLC/MS (3 min) retention time 1 .55 min. LRMS: m/z Molecular ion not detected.
94% With sodium borohydrid In methanol; water; acetone Example 73
Synthesis of 2-bromo-5-chlorobenzyl alcohol
2-Bromo-5-chlorobenzaldehyde (20.5 g) from Example 72 was dissolved with dry methanol (200 ml), followed by sodium borohydride (1.06 g) at 0° C., and the mixture was stirred for 30 minutes.
After addition of acetone, the solvent was removed under reduced pressure, water was added the obtained residue, and then extracted with ether.
The organic layer was washed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution, and dried over anhydrous sodium sulfate.
The solvent was removed under reduced pressure, to give the title compound (19.5 g; 94percent)
Reference: [1] Patent: WO2016/25932, 2016, A1, . Location in patent: Page/Page column 183
[2] Patent: WO2013/10880, 2013, A1, . Location in patent: Page/Page column 164
[3] Patent: US5587392, 1996, A,
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 19, p. 6108 - 6115
[5] Tetrahedron, 2015, vol. 71, # 42, p. 8172 - 8177
  • 8
  • [ 174265-12-4 ]
  • [ 57381-37-0 ]
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 29, p. 2844 - 2847
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7959 - 7963
  • 9
  • [ 60666-70-8 ]
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YieldReaction ConditionsOperation in experiment
85% at 55℃; for 1 h; Microwave irradiation General procedure: The benzyl alcohols substrates (1a–1p) (0.2mmol), FeCl3·6H2O (0.002mmol, 5.4mg) and triphenylmethanol 2 (0.2mmol, 52mg) were mixed in a dried vessel. Then the reaction was irradiated under the microwave at 55°C for 1h. The crude mixture was purified by a flash column chromatography to afford the benzaldehydes (4a–4p).
85% at 140℃; for 1 h; Microwave irradiation General procedure: To 10 mL of a microwave tube was added benzyl alcohol (0.5 mmol, 61.2 mg) and triphenylmethanol (0.5 mmol,(0.015 mmol, 11 mg) was added, the reaction mixture was heated to 120 ° C with a microwave reactor, and the reaction was stirred for 60 minutes. After completion of the reaction, the reaction product was separated by flash column chromatography to obtain the desired product I, 92percent.Substitution of 37.0 mg of Ph3PAuNTf2 for 11 mg of Ph3PAuNTf2,In the same manner as in Example 1,The target compound I,Yield 96percent.2-bromo-5-chlorobenzyl alcohol was used in place of 2-bromo-5-fluorobenzyl alcohol,In the same manner as in Example 4,The target compound V,Yield 85percent.
Reference: [1] Chemical Communications, 2018, vol. 54, # 20, p. 2467 - 2470
[2] Tetrahedron, 2015, vol. 71, # 38, p. 6744 - 6748
[3] Patent: CN104817441, 2017, B, . Location in patent: Paragraph 0034-0037; 0041; 0055-0057
[4] Journal of the American Chemical Society, 2011, vol. 133, # 20, p. 7916 - 7925
[5] Patent: US9540357, 2017, B1, . Location in patent: Page/Page column 68
  • 10
  • [ 66192-24-3 ]
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YieldReaction ConditionsOperation in experiment
92% With 4-methylmorpholine N-oxide In acetonitrile at 0℃; for 2 h; Molecular sieve Step 2: 2-bromo-5-chlorobenzaldehyde; 2-bromo-5-chlorobenzaldehyde was prepared according to literature precedent (/. Am. Chem. Soc. 2002, 124 (7), 1354): a mixture of activated powdered 4A molecular sieves (800 mg/mmol substrate), N- methylmorpholine-N-oxide (2 eq) and 2-bromomethyl-5-chlorobenzaldehyde (1 eq) in MeCN (0.16 M) was stirred at 0 0C for 2 h. The reaction was then filtered through a pad of celite and concentrated in vacuo to afford the title compound (92 percent)
Reference: [1] Patent: WO2006/46030, 2006, A2, . Location in patent: Page/Page column 28
[2] Journal of the American Chemical Society, 2002, vol. 124, # 7, p. 1354 - 1363
  • 11
  • [ 587-04-2 ]
  • [ 174265-12-4 ]
YieldReaction ConditionsOperation in experiment
90.1% at 10 - 25℃; for 3 h; Concentrated sulfuric acid (mass fraction 98percent, 150mL) was added to the reactor to reduce the temperature.The temperature of the system is ≤ 10°C, the compound A liquid (3-chlorobenzaldehyde, 0.5 mol) is slowly added dropwise, and after addition, an appropriate amount of catalyst I2 (0.236-2.36 mmol, 30 mg in this example) is added.When 3-chlorobenzaldehyde and catalyst 12 were added, there was a clear exothermic phenomenon and the reaction temperature of the system was controlled to be ≤ 10°C; System temperature control ≤15°C, add in batches 5-10 timesNBS (N-bromosuccinimide, 0.5 mol); Insulation reaction for 2h, slowly rise to 25 °C, and stir the reaction for 1h,GC detection of raw materials 3_ chlorobenzaldehyde content ≤ 1 percent,The reaction solution was purified by post-treatment to obtain an acicular off-white solid compound (98 g, purity 98.0percent, yield 90.1 percent).
Reference: [1] Patent: CN107879918, 2018, A, . Location in patent: Paragraph 0034-0037; 0058-0065; 0070-0085
[2] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 888 - 896
[3] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6414 - 6420
  • 12
  • [ 882772-93-2 ]
  • [ 174265-12-4 ]
YieldReaction ConditionsOperation in experiment
83% With sulfuric acid In methanol; water for 0.5 h; Reflux (2-Bromo-5-chlorophenyl)methanediyl diacetate(1.5 g, 4.7 mmol) was refluxed in MeOH–H2O (15 mL, 1/1 V/V) containing H2SO4 (1.6 mL)for 30 min. The reaction mixture was then diluted with H2O (15 mL) and extracted withEtOAc (3×20 mL). The combined organic layers were washed with H2O (20 mL) and brine(20 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue and 1 Mhydrochloric acid (4.0 mL) were heated for 3 h in THF (15 mL) under reflux. The solvent wasremoved under reduced pressure. The residue was purified by column chromatography (SiO2,hexane/EtOAc = 95/5). Yield: 0.84 g, 83 percent.
Reference: [1] Journal of the Serbian Chemical Society, 2015, vol. 80, # 7, p. 839 - 852
[2] Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 13, p. 5247 - 5253
  • 13
  • [ 14495-51-3 ]
  • [ 1333-82-0 ]
  • [ 174265-12-4 ]
YieldReaction ConditionsOperation in experiment
77% With sulfuric acid In ethanol; water; acetic anhydride Example 72
Synthesis of 2-bromo-5-chlorobenzaldehyde
To the solution of 2-bromo-5-chlorotoluene (25 g) in acetic anhydride (100 ml) and sulfuric acid (20 ml) was added dropwise chromium(VI) oxide (36.5 g) in acetic anhydride (200 ml) for 3 hours at -15° C.
The mixture was stirred for 1 hour at -5° C. and then poured into ice-cooled water, and extracted with ether.
The organic layer was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate.
After removal of the solvent under reduced pressure, the residue was suspended in ethanol (100 ml) and 3N-HCl (200 ml) and refluxed for 1 hour.
After removal of the solvent, water was added to the residue, and extracted with ether.
The organic layer was washed with saturated sodium hydrogencarbonate solution and saturated sodium chloride solution, and dried over anhydrous sodium sulfate.
After removal of the solvent under reduced pressure, the residue was purified by chromatography on a silica gel column (hexane:methylene chloride=4:1) to give the title compound (20.5 g; 77percent).
Reference: [1] Patent: US5587392, 1996, A,
  • 14
  • [ 7775-19-1 ]
  • [ 174265-12-4 ]
Reference: [1] Patent: US2012/261615, 2012, A1,
  • 15
  • [ 1313762-49-0 ]
  • [ 174265-12-4 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 23, p. 6635 - 6637
  • 16
  • [ 13780-71-7 ]
  • [ 174265-12-4 ]
Reference: [1] Patent: US2012/313083, 2012, A1,
  • 17
  • [ 14495-51-3 ]
  • [ 174265-12-4 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 23, p. 6635 - 6637
[2] Journal of the Serbian Chemical Society, 2015, vol. 80, # 7, p. 839 - 852
  • 18
  • [ 21739-93-5 ]
  • [ 174265-12-4 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 20, p. 7916 - 7925
[2] Chemical Communications, 2018, vol. 54, # 20, p. 2467 - 2470
  • 19
  • [ 33499-36-4 ]
  • [ 174265-12-4 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 15, p. 6414 - 6420
  • 20
  • [ 174265-12-4 ]
  • [ 536-74-3 ]
  • [ 1186603-47-3 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 9, p. 2228 - 2231
[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 9, p. 1922 - 1930
[3] Chemistry - A European Journal, 2015, vol. 21, # 50, p. 18122 - 18127
[4] Advanced Synthesis and Catalysis, 2013, vol. 355, # 2-3, p. 559 - 568
[5] Chemical Communications, 2013, vol. 49, # 96, p. 11320 - 11322
[6] Journal of the American Chemical Society, 2015, vol. 137, # 3, p. 1165 - 1180
[7] Journal of Organic Chemistry, 2015, vol. 80, # 15, p. 7635 - 7641
[8] Organic Letters, 2015, vol. 17, # 16, p. 4018 - 4021
[9] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10674 - 10681
[10] Chemistry - A European Journal, 2016, vol. 22, # 27, p. 9125 - 9129
[11] Patent: CN105330663, 2016, A, . Location in patent: Paragraph 0038; 0039; 0040
[12] Chemical Communications, 2017, vol. 53, # 85, p. 11666 - 11669
[13] Organic Letters, 2017, vol. 19, # 19, p. 5070 - 5073
[14] Organic Letters, 2017, vol. 19, # 21, p. 5856 - 5859
[15] Angewandte Chemie - International Edition, 2017, vol. 56, # 49, p. 15570 - 15574[16] Angew. Chem., 2017, vol. 129, p. 15776 - 15780,5
[17] Advanced Synthesis and Catalysis, 2018, vol. 360, # 15, p. 2825 - 2830
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