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[ CAS No. 2003-10-3 ] {[proInfo.proName]}

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Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 2003-10-3
Chemical Structure| 2003-10-3
Structure of 2003-10-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2003-10-3 ]

CAS No. :2003-10-3 MDL No. :MFCD03094283
Formula : C9H6BrF3O Boiling Point : -
Linear Structure Formula :- InChI Key :TZIYNLSEBAYCBZ-UHFFFAOYSA-N
M.W : 267.04 Pubchem ID :2778386
Synonyms :

Calculated chemistry of [ 2003-10-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.51
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) : -5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 3.28
Log Po/w (WLOGP) : 4.44
Log Po/w (MLOGP) : 3.24
Log Po/w (SILICOS-IT) : 3.75
Consensus Log Po/w : 3.34

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.68
Solubility : 0.0556 mg/ml ; 0.000208 mol/l
Class : Soluble
Log S (Ali) : -3.31
Solubility : 0.13 mg/ml ; 0.000486 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.49
Solubility : 0.00862 mg/ml ; 0.0000323 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.85

Safety of [ 2003-10-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P301+P330+P331-P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2003-10-3 ]

* 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 [ 2003-10-3 ]
  • Downstream synthetic route of [ 2003-10-3 ]

[ 2003-10-3 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
81.7% With pyridinium perbromide hydrobromide In toluene at 0 - 20℃; for 5 h; Reference Example 6
Synthesis of 2-bromo-3'-trifluoromethylacetophenone
To a toluene solution (423 mL) of commercially available 3'-trifluoromethylacetophenone (79.6 g, 0.423 mol) was added pyridinium bromide perbromide (135.4 g, 0.423 mol) under ice cooling and stirred for 5 hours while heating up to room temperature.
The reaction liquid was ice cooled again, followed by dropwise adding 400 mL of distilled water to stop reaction and fractionation.
A toluene layer was washed with 400 mL of a saturated aqueous solution of sodium bicarbonate, followed by drying with magnesium sulfate anhydride and concentration under reduced pressure and distillation under reduced pressure to obtain an objective compound (92.35 g, 81.7percent).
1H-NMR (200 MHzFT,TMS,CDCl3)
4.46(2H,s), 7.66(1H,brt,J=7.9Hz), 7.88(1H,brd,J=7.6Hz), 8.19(1H,brd,J=7.5Hz), 8.25(1H,brs)
b.p. 92°C /3 mmHg
78% With bromine In dichloromethane at 20℃; for 4 h; EXAMPLE 54; 4-{4-r4-(3-Trifluoromethyl-phenyl)-lH-imidazol-2-yl1-piperidin-l-yl}-lH-pyrazolo- r3,4-(/1pyrimidine hydrochloride; To a 22L 4-necked round bottom flask (fitted with addition funnel, nitrogen blanket, condenser, scrubber and mechanical stirrer) add: 3-trifluoromethyl- acetophenone (1500 g, 1.00 equiv; 7.97 moles) and dichloromethane (7.5L). Stir the resulting clear, colorless solution at room temperature while adding a solution of bromine (127 '4 g; 1.00 equiv; 7.97 moles) in dichloromethane at room temperature via addition funnel over 4 hours. Quench the reaction by slow addition of saturated aqueous NaHCψ3 (2000 mL), controlling the temperature by ice bath to less than 25 0C. Separate the phases and wash the organic layer with saturated aqueous sodium chloride (2000 mL), then dry the solution over sodium sulfate, filter and concentrate to a clear colorless oil. Purify this crude oil by silica gel chromatography (step gradient, 20percent to 50percent CH2Cl2 in heptane) to afford 2-Bromo-l-(3-trifluoromethyl-phenyl)-ethanone (1667g, 6.24 mol, 78percent) as a clear, colorless oil.
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 1, p. 34 - 41
[2] Journal of Organic Chemistry, 1980, vol. 45, # 24, p. 4989 - 4990
[3] Journal fuer Praktische Chemie/Chemiker-Zeitung, 1998, vol. 340, # 7, p. 649 - 655
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6572 - 6582
[5] Patent: EP1571148, 2005, A1, . Location in patent: Page/Page column 28
[6] Patent: WO2005/121105, 2005, A1, . Location in patent: Page/Page column 16
[7] Patent: WO2008/140947, 2008, A1, . Location in patent: Page/Page column 56
[8] Tetrahedron, 2008, vol. 64, # 22, p. 5191 - 5199
[9] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 7, p. 686 - 691
[10] Journal of medicinal chemistry, 1972, vol. 15, # 9, p. 989 - 994
[11] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 451 - 453
[12] Journal of Physical Chemistry, 1995, vol. 99, # 20, p. 8190 - 8195
[13] Chemical & Pharmaceutical Bulletin, 1995, vol. 43, # 9, p. 1497 - 1504
[14] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 17, p. 2421 - 2423
[15] Arzneimittel-Forschung/Drug Research, 2001, vol. 51, # 7, p. 569 - 573
[16] Patent: US4968707, 1990, A,
[17] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 8187 - 8195
[18] Patent: US2004/6058, 2004, A1, . Location in patent: Page/Page column 92
[19] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1432 - 1435
[20] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 1, p. 182 - 185
[21] Patent: WO2012/6473, 2012, A1, . Location in patent: Page/Page column 55-56
[22] Patent: WO2012/100734, 2012, A1, . Location in patent: Page/Page column 26
[23] Antimicrobial Agents and Chemotherapy, 2014, vol. 58, # 7, p. 4242 - 4245
[24] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5226 - 5237
[25] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 14 - 35
[26] Chemical Biology and Drug Design, 2015, vol. 86, # 4, p. 849 - 856
[27] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3669 - 3674
[28] Organic Letters, 2017, vol. 19, # 8, p. 1994 - 1997
[29] Patent: CN107266413, 2017, A, . Location in patent: Paragraph 0137; 0139; 0140; 0141
[30] Advanced Synthesis and Catalysis, 2018, vol. 360, # 8, p. 1628 - 1633
[31] Patent: WO2009/146358, 2009, A1, . Location in patent: Page/Page column 68
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Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 5, p. 982 - 1002
  • 3
  • [ 402-24-4 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9889 - 9894
  • 4
  • [ 108773-81-5 ]
  • [ 67-64-1 ]
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Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 14, p. 3143 - 3150
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  • [ 1801-10-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9889 - 9894
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