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[ CAS No. 19064-73-4 ] {[proInfo.proName]}

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Chemical Structure| 19064-73-4
Chemical Structure| 19064-73-4
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Product Details of [ 19064-73-4 ]

CAS No. :19064-73-4 MDL No. :MFCD11101043
Formula : C8H5BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :DHXVJJHOVGTNDK-UHFFFAOYSA-N
M.W : 225.04 Pubchem ID :614310
Synonyms :

Calculated chemistry of [ 19064-73-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.06
TPSA : 45.75 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) : -6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 1.82
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 2.27
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.0
Solubility : 0.226 mg/ml ; 0.001 mol/l
Class : Soluble
Log S (Ali) : -2.4
Solubility : 0.895 mg/ml ; 0.00398 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.09
Solubility : 0.0181 mg/ml ; 0.0000804 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.12

Safety of [ 19064-73-4 ]

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 [ 19064-73-4 ]

* 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 [ 19064-73-4 ]
  • Downstream synthetic route of [ 19064-73-4 ]

[ 19064-73-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 1445-69-8 ]
  • [ 19064-73-4 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With phosphorus pentabromide In dichloromethane for 24 h; Heating / reflux
Stage #2: at 120℃; for 2 h;
4-Bromo-2H-phthalazin-1-one: 2,3-Dihydro-1,4-phthalazinedione (12.5 g, 78 mmol) was suspended in DCE (200 ml) and phosphorous pentabromide (50.0 g, 116 mmol) was added in one portion and the reaction heated to reflux for 24 hours. A further portion of phosphorous pentabromide (20.0 g, 70 mol) was added and the reaction heated for a further 24 hours. The reaction was cooled to RT and poured into ice water. The resulting precipitate was filtered and washed with water to give a crude mixture of mono and dibrominated product (22.8 g). This crude material was suspended in HOAc (230.0 mL) and heated to 120° C. for 2 hrs. The reaction was cooled to RT and poured into ice water and the resulting precipitate filtered. The solid was washed with water and dried to give the title compound (10.4 g, 60percent yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 12.95 (1H, s), 8.25 (1H, dd), 8.03 (1H, ddd), 7.96-7.90-(2H, m); MS (ESI+)=(M+H)+ 225 227
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 35, p. 12363 - 12370
[2] Patent: US2007/219195, 2007, A1, . Location in patent: Page/Page column 39
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 312 - 319
[4] Patent: US4898872, 1990, A,
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 12, p. 2801 - 2805
[6] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3217 - 3226
  • 2
  • [ 119-39-1 ]
  • [ 19064-73-4 ]
YieldReaction ConditionsOperation in experiment
66% With bromine; potassium bromide In water at 20℃; for 31 h; Heating The reaction was carried out in a round-bottom flask fitted with a magnetic stirrer bar. To a suspension of phthalazin-1(2H)-one (2) or 2-methylphthalazin-1(2H)-one (5) or pyridopyridazinone 8 (6.84mmol) in water (55mL) (Method A) or in the acetate buffer solution pH=5.8 (55mL) (Method B), was added potassium bromide (8.44mmol) and bromine (8.44mmol) at an ambient temperature. The mixture was then stirred for 6h at an ambient temperature, and next the whole was heated to boiling and stirred for 25h until the bromine colour entirely disappeared. After cooling to an ambient temperature (in the case of 9 the mixture was adjusted to pH 7 with saturated NaHCO3) the separated solid was collected by filtration and washed with water (5mL). The crude product was purified by flash chromatography. 4.4.1 4-Bromophthalazin-1(2H)-one (3) (Path A) White solid; Yield: 693 mg, 45percent (Method A), 1.02 g, 66percent (Method B); Mp: 279-281 °C, (lit. 277-279 °C;273 °C ); Rf (DCM/AcOEt/Hex 6:1:1)=0.24; FTIR (KBr): ν=3022, 2931, 2892, 1671, 1659 (C=O), 1581 cm-1; 1H NMR (600 MHz, DMSO-d6): δ=12.94 (s, 1H, NH), 8.26 (d, J=7.9 Hz, 1H, 8 Ar-H), 8.06-8.01 (m, 1H, Ar-H), 7.97-7.91 (m, 2H, Ar-H); 13C NMR (150 MHz, DMSO-d6): δ=159.1 (C=O), 134.8, 133.1, 129.9, 129.4, 128.2, 127.6, 126.5 ppm; HRMS (ESI) m/z: calcd for C8H6BrN2O [M+H]+ 224.9658, found 224.9658.
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 4, p. 1520 - 1526
[2] Tetrahedron, 2016, vol. 72, # 49, p. 7942 - 7951
  • 3
  • [ 3660-90-0 ]
  • [ 19064-73-4 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: at 120℃; for 2 h;
Stage #2: at 0 - 20℃;
This crude material was suspended in acetic acid (230.OmL) and heated to 12O0C for 2 hrs. The reaction was cooled to room temperature and poured into ice water EPO <DP n="156"/>and the resulting precipitate filtered. The solid was washed with water and dried to give the title compound (10.4g, 60percent yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 12.95 (IH, s), 8.25 (IH, dd), 8.03 (IH, ddd), 7.96-7.90-(2H, m); MS (ESI+) = (M+H)+ 225 227
Reference: [1] Patent: WO2006/32518, 2006, A1, . Location in patent: Page/Page column 154; 155
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3217 - 3226
  • 4
  • [ 1445-69-8 ]
  • [ 7789-69-7 ]
  • [ 3660-90-0 ]
  • [ 19064-73-4 ]
Reference: [1] Patent: WO2006/32518, 2006, A1, . Location in patent: Page/Page column 154
  • 5
  • [ 85-44-9 ]
  • [ 19064-73-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 312 - 319
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 312 - 319
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3217 - 3226
  • 6
  • [ 1445-69-8 ]
  • [ 3660-90-0 ]
  • [ 19064-73-4 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1932, vol. &lt;2&gt; 135, p. 128,131
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. &lt;2&gt; 135, p. 128,131
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 312 - 319
  • 7
  • [ 119-67-5 ]
  • [ 19064-73-4 ]
Reference: [1] Tetrahedron, 2016, vol. 72, # 49, p. 7942 - 7951
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