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[ CAS No. 51206-40-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 51206-40-7
Chemical Structure| 51206-40-7
Chemical Structure| 51206-40-7
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Product Details of [ 51206-40-7 ]

CAS No. :51206-40-7 MDL No. :MFCD00234475
Formula : C9H5Br2N Boiling Point : -
Linear Structure Formula :- InChI Key :KXAHDPKQOFASEB-UHFFFAOYSA-N
M.W : 286.95 Pubchem ID :640981
Synonyms :

Calculated chemistry of [ 51206-40-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.14
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.45
Log Po/w (XLOGP3) : 3.82
Log Po/w (WLOGP) : 3.76
Log Po/w (MLOGP) : 3.26
Log Po/w (SILICOS-IT) : 3.79
Consensus Log Po/w : 3.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.64
Solubility : 0.00654 mg/ml ; 0.0000228 mol/l
Class : Moderately soluble
Log S (Ali) : -3.79
Solubility : 0.047 mg/ml ; 0.000164 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.4
Solubility : 0.00115 mg/ml ; 0.00000399 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.84

Safety of [ 51206-40-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51206-40-7 ]

* 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 [ 51206-40-7 ]
  • Downstream synthetic route of [ 51206-40-7 ]

[ 51206-40-7 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 491-30-5 ]
  • [ 51206-40-7 ]
YieldReaction ConditionsOperation in experiment
96% at 140℃; for 0.166667 h; A mixture of 2.90 g, 19.07mMol of isocarbostyril and 14.40 g, 33.68mMol of phosphorus pentabromide were allowed to melt together at 140 °C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried. wt. 5.50 g, 96percent yield, mp.=94-96°. Rf=0.66 in 40percent ethyl acetate in hexanes.
96% at 140℃; for 0.166667 h; Preparation of Intermediate A: A mixture of 2.90 g, 19.07mMol of isocarbostyril and 14.40 g, 33.68mMol of phosphorus pentabromide were allowed to melt together at 140 0C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried, wt. 5.50 g, 96percent yield, mp.=94-96°. Rf=0.66 in 40percent ethyl acetate in hexanes.
71.3% at 125 - 140℃; In a 250ml three neck flask fitted with overhead stirrer and condenser which is also connected to a scrubber solution, 1-hydroxyisoquinoline (lO.g, 68.89mmol) and PBrs (53.38g, 124 mmol) were taken. The reaction mixture was gradually heated to 140°C. At about 125°C - 130°C the solid melts and a deep read solution obtained which on further heating converts to yellowish solid at ~135°C. The reaction mixture was heated at this temperature for lOmin then allowed to cool to room temperature. The pale yellow solid was crushed and added in portions into ice with stirring to obtain a pale yellow powder which was filtered and washed with water (150ml) and dried in an oven at 50°C under vacuum. The crude solid was purified by recrystallisation from EtOAc/heptane (14. lg, 99.93percent HPLC, 71.3percent yield). 1H-NMR (600MHz, CDCI3, TMS): S= 8.47 (s, 1H), 8.32(d, 1H), 8.19 (m, 1H), 7.72(m, 1H).
Reference: [1] Patent: EP1228063, 2009, B1, . Location in patent: Page/Page column 32
[2] Patent: WO2007/118602, 2007, A1, . Location in patent: Page/Page column 51
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 8029 - 8047
[4] Patent: WO2017/103586, 2017, A1, . Location in patent: Page/Page column 38
[5] Patent: US2010/222345, 2010, A1, . Location in patent: Page/Page column 97
  • 2
  • [ 3749-21-1 ]
  • [ 51206-40-7 ]
YieldReaction ConditionsOperation in experiment
73% With N,N-dimethyl-formamide; phosphorus(V) oxybromide In dichloromethane at 0 - 25℃; for 6 h; Inert atmosphere General procedure: The procedure is identical to general procedure I, except that reactions were conducted at 0.2 M concentration with N-oxide (1.00 equiv), POBr3 (3.00 equiv), DMF (1.50 equiv) at rt. 4.2 General procedure I for the bromination of azine N-oxides (0013) To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 °C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7–8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.
Reference: [1] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768
  • 3
  • [ 491-30-5 ]
  • [ 51206-40-7 ]
YieldReaction ConditionsOperation in experiment
96% at 140℃; for 0.166667 h; Neat (no solvent) A mixture of 2.90 g, 19.07 mMol of isocarbostyril and 14.40 g, 33.68 mMol of phosphorus pentabromide were allowed to melt together at 140° C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried. wt. 5.50 g, 96percent yield, mp.=94-96°. Rf=0.66 in 40percent ethyl acetate in hexanes.
Reference: [1] Patent: US6689883, 2004, B1, . Location in patent: Page column 43
  • 4
  • [ 1532-71-4 ]
  • [ 51206-40-7 ]
Reference: [1] Patent: US4678781, 1987, A,
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