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[ CAS No. 2632-13-5 ] {[proInfo.proName]}

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Chemical Structure| 2632-13-5
Chemical Structure| 2632-13-5
Structure of 2632-13-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2632-13-5 ]

CAS No. :2632-13-5 MDL No. :MFCD00000201
Formula : C9H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XQJAHBHCLXUGEP-UHFFFAOYSA-N
M.W : 229.07 Pubchem ID :4965
Synonyms :
α-Bromo-4’-methoxyacetophenone;NSC 129010;Protein Tyrosine Phosphatase Inhibitor II;4-Methoxyphenacyl bromide;ω-Bromo-4’-methoxyacetophenone;4-(Bromoacetyl)anisole;PTP Inhibitor II
Chemical Name :2-Bromo-1-(4-methoxyphenyl)ethanone

Calculated chemistry of [ 2632-13-5 ]

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 : 51.0
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) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 2.27
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 2.71
Consensus Log Po/w : 2.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.03
Solubility : 0.216 mg/ml ; 0.000942 mol/l
Class : Soluble
Log S (Ali) : -2.73
Solubility : 0.428 mg/ml ; 0.00187 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.74
Solubility : 0.0419 mg/ml ; 0.000183 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 2632-13-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 UN#:3261
Hazard Statements:H302+H312+H332-H314-H290 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2632-13-5 ]

* 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 [ 2632-13-5 ]
  • Downstream synthetic route of [ 2632-13-5 ]

[ 2632-13-5 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 2632-13-5 ]
  • [ 531-95-3 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 18, p. 4884 - 4887
  • 2
  • [ 487-70-7 ]
  • [ 2632-13-5 ]
  • [ 491-80-5 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With thiamine hydrochloride In ethanol at 20℃; for 0.25 h; Green chemistry
Stage #2: at 20℃; for 2 h; Green chemistry
General procedure: To prepare catalyst, 0.21 g of thiamine hydrochloride (0.6 mmol) was dissolved in 0.64 mL of water and added 2.4 mLof 95percent ethanol (water : 95percent ethanol = ~1:4). The solution was cooled in an ice bath, then added 0.40 mL of 3 M NaOH(1.2 mmol) dropwise with stirring in a manner such that thetemperature remained below 20 °C. Intense yellow coloured solution changed to pale yellow solution of thiamine (thiazolium ion)/N-heterocyclic carbene (Scheme 1).47 In a 25-mL round bottom flask, a mixture of phenacylbromide 1 (2.5 mmol, 0.5 g in case of 1a) and thiamine (0.6 mmol, 25 mol percent) in ethanol (4 mL) was stirred at room temperature for 15 min. Then, salicylaldehyde 2 (2.5 mmol, 0.26 mL in case of 2a) was added slowly and the mixture was stirred at room temperature until the reaction was completed (as monitored by TLC) (Table 3) . The reaction mixture was then poured into 20 mL of distilled water and extracted with ethyl acetate (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The resulting product isoflavone 3 was further purified either by recrystallizationor by column chromatography (Ethyl acetate:Hexane, 1:4v/v). All compounds were characterized by their mp and 1HNMR, 13CNMR and mass spectral data.
Reference: [1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1070 - 1076
  • 3
  • [ 90-05-1 ]
  • [ 2632-13-5 ]
  • [ 19513-80-5 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 3, p. 702 - 706
[2] Green Chemistry, 2016, vol. 18, # 24, p. 6545 - 6555
[3] Journal of the American Chemical Society, 2014, vol. 136, # 4, p. 1218 - 1221
[4] Journal of Organic Chemistry, 2014, vol. 79, # 22, p. 11091 - 11100
[5] Organic Letters, 2016, vol. 18, # 19, p. 5166 - 5169
[6] Green Chemistry, 2016, vol. 18, # 7, p. 2029 - 2036
[7] Green Chemistry, 2016, vol. 18, # 23, p. 6229 - 6235
[8] Journal of Catalysis, 2017, vol. 346, p. 170 - 179
[9] Green Chemistry, 2017, vol. 19, # 19, p. 4538 - 4543
  • 4
  • [ 2632-13-5 ]
  • [ 108-59-8 ]
  • [ 22027-50-5 ]
YieldReaction ConditionsOperation in experiment
7%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1 h; Inert atmosphere; Sealed tube
Stage #2: at 0 - 20℃; for 18 h; Inert atmosphere; Sealed tube
General procedure: Reaction of dimethyl malonate/LHMDS system with benzyl bromide. A 1M LHMDS solution in anhydrous THF (1.0mL, 1.0mmol) was treated at 0°C with a solution of dimethyl malonate (0.132g, 1.0mmol) in anhydrous THF (3.0mL) and the reaction mixture was stirred at the same temperature for 1h. A solution of benzyl bromide (0.171g, 0.12mL, 1.0mmol) in anhydrous THF (0.5mL) was added dropwise at 0°C and the reaction mixture was stirred for 18h at room temperature. Dilution with Et2O and evaporation of the washed (saturated aqueous NaCl) organic solution afforded a crude reaction mixture (0.19g) consisting of a 35:33:32 mixture (68percent conversion) of dimethyl benzylmalonate (10a), methyl phenylacetate (11a) and unreacted dimethyl malonate (1H NMR) which was subjected to preparative TLC by using a 9:1 hexane/AcOEt mixture as the eluant. Extraction of the two most intense bands (the faster moving band contained 10a) afforded pure dimethyl benzylmalonate (10a) (0.027g, 12percent yield) and methyl phenylacetate (11a) (0.017g, 11percent yield).
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 15, p. 1644 - 1647
  • 5
  • [ 2632-13-5 ]
  • [ 3883-94-1 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With sodium diformamide In acetonitrile at 20 - 70℃; for 4 h;
Stage #2: With hydrogenchloride In ethanol for 1 h; Heating / reflux
To a stirred solution of 2-Bromo-4'-methoxyacetophenone (20.0 g, 87.3 mmol) in CH3CN (90 mL), was added sodium diformylamide (9.95 g, 104.76 mmol, 1.2 [EQ).] The resulting mixture was stirred for 2h at RT, and heated for 2 h at [70 °C] (monitored by TLC). Solvent was removed under reduced pressure. Then [ETOH] (250 mL) and Conc. HCl (40 mL) were added. The reaction mixture was refluxed for 1h. Solvent was removed by rotavap. The crude product was suspended in iPr-OH (100 mL) and stirred at RT O/N. The off-white pure product was obtained by filtration (17.28 g, [98percent). 1H NMR] (300 MHz, [DMSO-D6)] 8 8.4 (br), 8.0 (d, 2H), 7.1 (d, 2H), 4.5 (s, 2H), 3.9 (s, 3H). MS (APCI+) [M/Z] 166 [(M-HCL).] Yield: 98percent
Reference: [1] Patent: WO2004/18428, 2004, A1, . Location in patent: Page 356
[2] Journal of Medicinal Chemistry, 1982, vol. 25, # 9, p. 1045 - 1050
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1119 - 1121
[4] Synthesis, 1990, # 7, p. 615 - 618
[5] Patent: US4898862, 1990, A,
[6] Patent: EP238357, 1991, B1,
[7] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2550 - 2557
[8] Journal of Pharmaceutical Sciences, 2014, vol. 103, # 9, p. 2797 - 2808
[9] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 849 - 853
[10] Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9275 - 9289
[11] Patent: WO2007/149395, 2007, A2, . Location in patent: Page/Page column 57
  • 6
  • [ 100-97-0 ]
  • [ 2632-13-5 ]
  • [ 3883-94-1 ]
Reference: [1] Patent: US5217645, 1993, A,
  • 7
  • [ 18197-26-7 ]
  • [ 2632-13-5 ]
  • [ 3883-94-1 ]
Reference: [1] Synthesis, 1990, # 7, p. 615 - 618
  • 8
  • [ 2632-13-5 ]
  • [ 84449-65-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 8, p. 1057 - 1066
  • 9
  • [ 2632-13-5 ]
  • [ 82640-04-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 8, p. 1057 - 1066
  • 10
  • [ 2632-13-5 ]
  • [ 92409-15-9 ]
Reference: [1] Green Chemistry, 2016, vol. 18, # 24, p. 6545 - 6555
  • 11
  • [ 2632-13-5 ]
  • [ 92409-23-9 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 19, p. 5166 - 5169
[2] Green Chemistry, 2016, vol. 18, # 24, p. 6545 - 6555
  • 12
  • [ 90-05-1 ]
  • [ 2632-13-5 ]
  • [ 92409-23-9 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 4, p. 1218 - 1221
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