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[ CAS No. 4509-90-4 ] {[proInfo.proName]}

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Chemical Structure| 4509-90-4
Chemical Structure| 4509-90-4
Structure of 4509-90-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4509-90-4 ]

CAS No. :4509-90-4 MDL No. :MFCD00013660
Formula : C5H8BrClO Boiling Point : -
Linear Structure Formula :- InChI Key :OKRUMSWHDWKGHA-UHFFFAOYSA-N
M.W : 199.47 Pubchem ID :521173
Synonyms :

Calculated chemistry of [ 4509-90-4 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.02
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 2.18
Log Po/w (WLOGP) : 2.32
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 2.31
Consensus Log Po/w : 2.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.19
Solubility : 1.3 mg/ml ; 0.00651 mol/l
Class : Soluble
Log S (Ali) : -2.17
Solubility : 1.34 mg/ml ; 0.00673 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.92
Solubility : 0.239 mg/ml ; 0.0012 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.39

Safety of [ 4509-90-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4509-90-4 ]

* 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 [ 4509-90-4 ]
  • Downstream synthetic route of [ 4509-90-4 ]

[ 4509-90-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 4509-90-4 ]
  • [ 37675-18-6 ]
Reference: [1] Helvetica Chimica Acta, 2005, vol. 88, # 8, p. 2235 - 2249
  • 2
  • [ 4509-90-4 ]
  • [ 100-01-6 ]
  • [ 38560-30-4 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃;
Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃;
Part A: 4-Nitroaniline (30.0 g, 217.2 mmol) and 400 mL of dry THF were stirred together at 0° C. and N,N-diisopropylethylamine (28.3 g, 219.0 mmol) dissolved in 100 mL of THF was slowly added. Then 5-bromovaleryl chloride (43.3 g, 217.2 mmol) in 180 mL of THF was slowly added while maintaining the temperature at 0-5° C. After addition was complete, the reaction was allowed to warm to rt over 2.5 hours. [0732] The reaction was again cooled to 0° C. and potassium t-butoxide (1.0 M in THF, 434 ml, 434 mmol) was added and the reaction allowed to warm to rt overnight. The reaction was evaporated, dissolved in EtOAc and washed with NaHCO3, water, then brine. Next it was dried over sodium sulfate and evaporated to give the corresponding lactam (44.68 g, 96percent yield). LRMS (AP+) 221.1 (M+H)+.
96.82% With pyridine; dmap In tetrahydrofuran at 0 - 100℃; for 1 h; A mixture of 13.8 g (0.l mol) of p-nitroaniline Was added to 55. 2 mL of tetrahydrofuran,11.85 g (0.15 mol) of pyridine was added, And 1. 38 g (10percent w / w) DMAP, The temperature 0 ° C -10 ° C drop of 5-bromo valeryl chloride 23.94 (0.12mol), within 1 hour drop finished,TLC detection of the disappearance of p-nitroaniline, a large number of white crystals precipitated, filtered and washed with 13. 8mL tetrahydrofuran filter cake, 0 ° C -10 ° C to the filtrate slowly add potassium hydroxide 0. 93g(Content: 90percent, 0.15 mol) was added over 1 hour, and the reaction was continued until the completion of the TLC reaction.5 ml of concentrated hydrochloric acid (0.05 mol) was added dropwise to a solution of 5-6. The reaction solution was evaporated to dryness under reduced pressure, and the cake was washed with tetrahydrofuran.And dried to obtain 21.30 g (yield 96.82percent) of the target compound 7.
90%
Stage #1: at 20℃; for 1 h; Green chemistry
Stage #2: at 20℃; for 4 h; Green chemistry
Potassium carbonate 40 g, water 30 mL, p-nitroaniline 57.2 g, tetrahydrofuran 272 mL were added to the reaction flask.Tetra-n-butylammonium bromide (2.0 g) was stirred at room temperature, and 89.5 g of 5-bromovaleryl chloride was added dropwise.After stirring for 1 hour, add 26.4 g of potassium hydroxide and stir at room temperature for 4 hours.40 mL of water and 60 mL of ethyl acetate were added. After stirring, the mixture was allowed to stand for stratification. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo (45°-55° C., -0.085 MPa--0.1 MPa). Light yellow solid.Add 100 mL of ethyl acetate, stir at room temperature for 2 hours, filter, vacuum dry and dry at -0.01 MPa to -0.1 MPa, 45°C to 55°C for 8 hours to 12 hours to obtain 1-(4-nitrophenyl) )-2-Piperidinone 76 g, 90percent yield.
Reference: [1] Patent: US2003/232804, 2003, A1, . Location in patent: Page 102
[2] Patent: CN103694237, 2016, B, . Location in patent: Paragraph 0069-0071
[3] Patent: CN107955002, 2018, A, . Location in patent: Paragraph 0121
[4] Patent: US2003/232804, 2003, A1, . Location in patent: Page 96
  • 3
  • [ 4509-90-4 ]
  • [ 38560-30-4 ]
Reference: [1] Patent: WO2014/203275, 2014, A2,
[2] Patent: US9603846, 2017, B2,
  • 4
  • [ 4509-90-4 ]
  • [ 10226-29-6 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 7, p. 1427 - 1429
  • 5
  • [ 4509-90-4 ]
  • [ 65632-62-4 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 5, p. 1734 - 1737
[2] Journal of Organic Chemistry, 2004, vol. 69, # 5, p. 1734 - 1737
[3] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 11, p. 1587 - 1592
  • 6
  • [ 4509-90-4 ]
  • [ 75-65-0 ]
  • [ 164365-88-2 ]
Reference: [1] Organic Preparations and Procedures International, 2004, vol. 36, # 2, p. 141 - 149
  • 7
  • [ 4509-90-4 ]
  • [ 193693-68-4 ]
Reference: [1] Helvetica Chimica Acta, 2005, vol. 88, # 8, p. 2235 - 2249
  • 8
  • [ 4509-90-4 ]
  • [ 193693-67-3 ]
Reference: [1] Helvetica Chimica Acta, 2005, vol. 88, # 8, p. 2235 - 2249
  • 9
  • [ 4509-90-4 ]
  • [ 540-37-4 ]
  • [ 385425-15-0 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With triethylamine In tetrahydrofuran at 0 - 20℃;
Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃;
Part A. 4-iodoaniline (45.82 g, 209.2 mmol) and triethylamine (65.61 ml, 470.7 mmol) were dissolved into THF (800 mL) and cooled to 0° C. 5-Bromovaleryl chloride (50.0 g, 251.1 mmol) dissolved in THF (200 mL) was added dropwise to the reaction. The reaction was warmed to room temperature and stirred overnight. Reaction was cooled to 0° C. and potassium tert-butoxide (70.43 g, 627.6 mmol) was slowly added. The reaction was warmed to room temperature and stirred overnight. The reaction was concentrated and then re-dissolved in ethyl acetate (500 mL) and 3N HCl (500 mL), extracted with ethyl acetate (2.x.250 mL), washed with 1N HCl (3.x.250 mL), washed with brine (1.x.250 mL), and dried (Na2SO4). Purification by silica gel chromatography using 0percent-100percentethyl acetate/hexane gradient as eluent to afford 51.03 g (81percent): 1H NMR (CDCl3) δ 7.70 (d, j=8.4 Hz, 2H), 7.03 (d, j=8.8 Hz, 2H), 3.62 (t, j=5.9 Hz, 2H), 2.56 (t, j=5.7 Hz, 2H), 2.50-1.88 (m, 4H) ppm.
81%
Stage #1: With triethylamine In tetrahydrofuran at 0 - 20℃;
Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃;
Part A. 4-iodoaniline (45.82 g, 209.2 mmol) and triethylamine (65.61 mL, 470.7 mmol) were dissolved into THF (800 mL) and cooled to 0° C. 5-Bromovaleryl chloride (50.0 g, 251.1 mmol) dissolved in THF (200 mL) was added dropwise to the reaction. The reaction was warmed to rt and stirred overnight. Reaction was cooled to 0° C. and potassium tert-butoxide (70.43 g, 627.6 mmol) was slowly added. The reaction was warmed to rt and stirred overnight. The reaction was concentrated and then redissolved in ethyl acetate (500 mL) and 3N HCl (500 mL), extracted with ethyl acetate (2×250 mL), washed with 1N HCl (3×250 mL), washed with brine (1×250 mL), and dried (Na2SO4). Purification by silica gel chromatography using 0percent-100percent ethyl acetate/hexane gradient as eluent to afford 51.03 g (81percent): 1H NMR (CDCl3)□ δ 7.70 (d,j=8.4 Hz, 2H), 7.03 (d,j=8.8 Hz, 2H), 3.62 (t,j=5.9 Hz, 2H), 2.56 (t,j=5.7 Hz, 2H), 2.50-1.88 (m, 4H) ppm.
48.5%
Stage #1: With triethylamine In tetrahydrofuran at 0 - 20℃; for 16.5 h;
Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran
EXAMPLE 1; l-(4-Methoxyphenyl)-7-oxo-6-(4-(2-oxo-l-piperidinyl)phenyl)-4,5,6,7- tetrahydro-lH-pyrazole- [3,4-c] pyridine-3-carboxamide; l-(4-Iodophenyl) piperidin-2-one:; Triethylamine (31.10 g, 307.38 mmol) was added to a solution of 4-iodoaniline (30.0 g, 136.98 mmol) in tetrahydrofuran (80OmL). After cooling the mixture to about 0 0C, a solution of 5- bromo-pentanoyl chloride (32.7g, 163.90 mmol) in tetrahydrofuran (20OmL) was slowly added to the mixture over a period of about 30 minutes. The mixture was stirred at ambient temperature for about 16 hours. The mixture was then cooled to about 0 0C, and potassium tert-butoxide (46.0 g, 410 mmol) was slowly added. The mixture was stirred at ambient temperature for about 18 hours. Evaporation of the solvent in vacuo afforded a thick oily mass which was acidified to a pH of about 2.0 by adding a 3 N hydrochloric acid solution. Following standard extractive workup with ethyl acetate (3 x 500 mL), the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane, 0percent-100percent) to give the title product as an off-white solid (20.0 g, yield = 48.5percent). mp: 108-1100C. 1H NMR (400 MHz, CDCl3) δ 1.93-1.95 (m, 4H), 2.55 (t, J=6.2 Hz, 2H), 3.62 (t, J=5.2 Hz, 2H), 7.02 (d, J= 8.4 Hz, 2H), 7.70 (d, J=8.4 Hz, 2H); IR (KBr) υ 3256, 3049, 2936, 2864, 1634, 1576, 1482, 1434, 1164, 1000, 819, 709 cm"1; MS 302 (M + 1).
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 22, p. 5339 - 5356
[2] Patent: US2003/232804, 2003, A1, . Location in patent: Page 94
[3] Patent: US2017/50964, 2017, A1, . Location in patent: Paragraph 0699
[4] Patent: WO2010/30983, 2010, A2, . Location in patent: Page/Page column 28
  • 10
  • [ 4509-90-4 ]
  • [ 385425-15-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 4141 - 4147
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5584 - 5589
[3] Patent: WO2015/177801, 2015, A1,
[4] Patent: US2017/313695, 2017, A1,
[5] Patent: WO2017/187245, 2017, A1,
  • 11
  • [ 4509-90-4 ]
  • [ 473927-64-9 ]
Reference: [1] Patent: WO2015/177801, 2015, A1,
[2] Patent: WO2015/177801, 2015, A1,
  • 12
  • [ 4509-90-4 ]
  • [ 503615-03-0 ]
Reference: [1] Patent: WO2014/203275, 2014, A2,
[2] Patent: US9603846, 2017, B2,
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