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[ CAS No. 52449-43-1 ] {[proInfo.proName]}

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Chemical Structure| 52449-43-1
Chemical Structure| 52449-43-1
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Product Details of [ 52449-43-1 ]

CAS No. :52449-43-1 MDL No. :MFCD00032743
Formula : C9H9ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WWIYGBWRUXQDND-UHFFFAOYSA-N
M.W : 184.62 Pubchem ID :104196
Synonyms :

Calculated chemistry of [ 52449-43-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.32
TPSA : 26.3 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) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 2.06
Log Po/w (MLOGP) : 2.55
Log Po/w (SILICOS-IT) : 2.67
Consensus Log Po/w : 2.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.71
Solubility : 0.363 mg/ml ; 0.00197 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.407 mg/ml ; 0.00221 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.5
Solubility : 0.0591 mg/ml ; 0.00032 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 52449-43-1 ]

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 [ 52449-43-1 ]

* 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 [ 52449-43-1 ]
  • Downstream synthetic route of [ 52449-43-1 ]

[ 52449-43-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 52449-43-1 ]
  • [ 86147-28-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732
  • 2
  • [ 52449-43-1 ]
  • [ 24091-92-7 ]
YieldReaction ConditionsOperation in experiment
63% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 3 h; Heating / reflux A solution of 4-chlorophenylacetic acid methyl ester (14.6 g, 79.1 mmol), N-bromosuccinimide (14.4 g, 80.7 mmol), and benzoyl peroxide (1.91 g, 7.89 mmol) in carbon tetrachloride (100 mL) was heated at reflux for 3 h. After the mixture was cooled at room temperature, hexanes (500 mL) was added. The reaction mixture was filtered and the solvent was evaporated in vacuo. The crude material was purified by column chromatography on silica (EtOAc/Hexanes, 15:85) to give the title compound as colorless oil (16.9 g, 63percent): 1H NMR (400 MHz, CDCl3) δ 3.81 (s, 3H, CH3), 5.34 (s, 1H, CH), 7.44 (dd, J = 60.4 Hz, J = 8.4 Hz, 4H, ArH).
63% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 3 h; Heating / reflux A solution of 4-chlorophenylacetic acid methyl ester (14.6 g, 79.1 mmol), N-bromosuccinimide (14.4 g, 80.7 mmol), and benzoyl peroxide (1.91 g, 7.89 mmol) in carbon tetrachloride (100 mL) was heated at reflux for 3 h.
After the mixture was cooled at room temperature, hexanes (500 mL) was added.
The reaction mixture was filtered and the solvent was evaporated in vacuo.
The crude material was purified by column chromatography on silica (EtOAc/Hexanes, 15:85) to give the title compound as colorless oil (16.9 g, 63percent): 1H NMR (400 MHz, CDCl3) δ 3.81 (s, 3H, CH3), 5.34 (s, 1H, CH), 7.44 (dd, J=60.4 Hz, J=8.4 Hz, 4H, ArH).
103% With N-Bromosuccinimide In tetrachloromethane REFERENTIAL EXAMPLE 2
Methyl (4-chlorophenyl)bromoacetate
To a solution of 102 g (0.55 mole) of methyl (4-chlorophenyl)acetate in 100 ml of carbon tetrachloride was added 97.9 g (0.55 mole) of N-bromosuccinimide.
The resulting mixture was refluxed and irradiated with a 500 W bromo lamp for 5 hours.
It was then cooled, filtered, and the filtrate was evaporated to dryness to give 150 g (103percent yield) of methyl (4-chlorophenyl)bromoacetate.
NMR (CDCl3) δ ppm; 3.79 (3H, s), 5.31 (1H, s), 7.3-7.7 (4H, s)
103% With N-Bromosuccinimide In tetrachloromethane Referential Example 2
Methyl (4-chlorophenyl)bromoacetate
To a solution of 102 g (0.55 mole) of methyl (4-chlorophenyl)acetate in 100 ml of carbon tetrachloride was added 97.9 g (0.55 mole) of N-bromosuccinimide.
The resulting mixture was refluxed and irradiated with a 500 W bromo lamp for 5 hours.
It was then cooled, filtered, and the filtrate was evaporated to dryness to give 150 g (103percent yield) of methyl (4-chlorophenyl)bromoacetate.
NMR (CDCl3) δ ppm; 3.79 (3H, s), 5,31 (1H, s), 7.3-7.7 (4H, s)
7.2 g With N-Bromosuccinimide; dibenzoyl peroxide In acetonitrile for 48 h; Reflux Benzoyl peroxide (5 mg) was added to a mixture of methyl 2-(4-chlorophenyl)- acetate [CAS 52449-43-1 ] (5.0 g, 29.7 mmol) and NBS (4.82 g, 27.1 mmol) in CH3CN (80 mL). The mixture was heated under reflux for 48 h and the solvent was evaporated under reduced pressure. The mixture was taken up in cyclohexane/EtOAc 80/20 and the precipitate was filtered off and discarded (succinimide). The filtrate was concentrated under reduced pressure to give methyl 2-bromo-2-(4-chlorophenyl)acetate 3a (7.2 g). The compound was used as such in the next step.

Reference: [1] Tetrahedron, 2002, vol. 58, # 51, p. 10113 - 10126
[2] Patent: EP1712235, 2006, A2, . Location in patent: Page/Page column 53
[3] Patent: US2004/220179, 2004, A1, . Location in patent: Page 34
[4] Journal of Medicinal Chemistry, 1993, vol. 36, # 23, p. 3738 - 3742
[5] Patent: US2003/191190, 2003, A1,
[6] Patent: WO2006/71819, 2006, A1, . Location in patent: Page/Page column 80
[7] Patent: US4849434, 1989, A,
[8] Patent: EP256687, 1991, B1,
[9] Patent: EP1595867, 2005, A1, . Location in patent: Page/Page column 29
[10] Patent: US2010/48619, 2010, A1, . Location in patent: Page/Page column 17
[11] Advanced Synthesis and Catalysis, 2015, vol. 357, # 11, p. 2479 - 2484
[12] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 12, p. 2866 - 2869
[13] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732
[14] Patent: WO2017/167953, 2017, A1, . Location in patent: Page/Page column 20
  • 3
  • [ 67-56-1 ]
  • [ 24091-92-7 ]
  • [ 52449-43-1 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: at 55℃; for 1 h;
Stage #2: at 9 - 80℃; for 23.3333 h;
The initial compound listed in Scheme 1, i.e., 4-chlorophenylacetic acid, is readily available from several commercial sources (e.g., Aldrich and Fluka).fO247f A 5-L Morton reactor equipped with a magnetic stirrer, a pot temperature control, and addition funnel was vented through a gas scrubber and charged with p- chlorophenylacetic acid (720 gm, 4.2 moles) and SOCl2 (390 ml, 630 gm, 5.3 moles). The reaction was stirred, heated and held at 55° +5° C for 1 hour. Bromine (220 ml., 670 gm, 5.3 moles) was then added over 20 min. and stirred at 55°+5° C for 16 hours. The temperature was raised to 80° C for 7 hours and then cooled to 9° C in an ice-water bath. Methanol (2.0 L, 1.6 kg, 49.4 moles) was then carefully added. The solvent was stripped to obtain 2 liquids weighing 1.28kg. These were dissolved in a mixture of 0.84 L water and 2.1 L ether and separated. The organic phase was washed once with 0.78 L 25percent (w:w) aqueous NaCl and dried over 0.13 kg MgSO4. This was filtered through Whatman No.1 filter paper and stripped of solvent to obtain 0.985 kg of orange liquid. The proton NMR showed this to be 80percent product and 19percent non-brominated ester. The HPLC showed 82percent product and 18percent non- brominated ester. HPLC was run on a Zorbax SB-C8 column at 30° C measuring 250 X 4.6 mm and 5 μ particle size. The mobile phase was 60:40 (v:v) acetonitrile: 0.1percent H3PO4 at 1.5 ml/min. Detection was at 210 nm. The injected sample of 1 μl was dissolved in acetonitrile at a concentration of 10 mg/ml. The product had a retention time of 5.0 min. and that of the non-brominated ester was 3.8 min. This crude product was purified by vacuum distillation to obtain 96percent pure product with an 84percent yield. The product proton NMR (CDCl3, 300 MHz) showed shifts at 3.79 (s, 3H), 5.32 (s, IH) and 7.20-7.55 (m, 4H) ppm.
Reference: [1] Patent: WO2006/102375, 2006, A2, . Location in patent: Page/Page column 70
  • 4
  • [ 52449-43-1 ]
  • [ 6529-53-9 ]
Reference: [1] Journal of the American Chemical Society, 1977, vol. 99, # 9, p. 3059 - 3067
[2] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 386 - 393
  • 5
  • [ 52449-43-1 ]
  • [ 75-16-1 ]
  • [ 5468-97-3 ]
Reference: [1] Patent: US2012/252802, 2012, A1, . Location in patent: Page/Page column 77
  • 6
  • [ 52449-43-1 ]
  • [ 769944-39-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3726 - 3732
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