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[ CAS No. 666747-06-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 666747-06-4
Chemical Structure| 666747-06-4
Chemical Structure| 666747-06-4
Structure of 666747-06-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 666747-06-4 ]

CAS No. :666747-06-4 MDL No. :MFCD09996906
Formula : C7H6Br2O Boiling Point : -
Linear Structure Formula :- InChI Key :VXEVXBMLHQPKGA-UHFFFAOYSA-N
M.W : 265.93 Pubchem ID :17836195
Synonyms :

Calculated chemistry of [ 666747-06-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.97
TPSA : 20.23 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) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 2.42
Log Po/w (WLOGP) : 2.55
Log Po/w (MLOGP) : 3.03
Log Po/w (SILICOS-IT) : 3.03
Consensus Log Po/w : 2.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.39
Solubility : 0.108 mg/ml ; 0.000406 mol/l
Class : Soluble
Log S (Ali) : -2.49
Solubility : 0.866 mg/ml ; 0.00326 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.93
Solubility : 0.031 mg/ml ; 0.000117 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.4

Safety of [ 666747-06-4 ]

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

Application In Synthesis of [ 666747-06-4 ]

* 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 [ 666747-06-4 ]
  • Downstream synthetic route of [ 666747-06-4 ]

[ 666747-06-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 557-21-1 ]
  • [ 666747-06-4 ]
  • [ 90110-98-8 ]
YieldReaction ConditionsOperation in experiment
44% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃; for 5 h; Inert atmosphere Zinc cyanide (1.01 g, 8.65 mmol) and tetrakis(triphenylphosphine) palladium (Pd(PPh3)4, 0.50 g, 0.43 mmol) were added into a solution of 2,4-dibromobenzyl alcohol (1-1, 2.3 g, 8.65 mmol) in DMF (20 mL). After deoxygenated via argon bubbling, the reaction mixture was heated at 80 °C and reacted for 5 hours, cooled down to room temperature, diluted with ethyl acetate (80 mL), washed successively with water (80 mLx3) and saturated brine (80 mLx3), dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated to obtain a crude product. The crude product was then purified by column chromatography (elution system: petroleum ether: ethyl acetate = 15/1-4/1) to obtain a white solid product (0.81 g, 44percent yield). The molecular ion peak shown by liquid chromatography-mass spectrometry was: MS (ESI): m/z 211.9/213.9 [M+H]+. NMR: 1HNMR (400 MHz, CDCl3) δ: 7.82 (s, 1 H), 7.69 (d, J = 8.0 Hz, 1 H), 7.65 (d, J = 8.0 Hz, 1 H), 4.80 (s, 2H).
Reference: [1] Patent: EP3048103, 2016, A1, . Location in patent: Paragraph 0081; 0082
  • 2
  • [ 54335-33-0 ]
  • [ 666747-06-4 ]
YieldReaction ConditionsOperation in experiment
43% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 1 h; At 0 °C, lithium aluminum hydride (1.14 g, 30 mmol) was dropped into a solution of methyl 2,4-dibromobenzoate (5.90 g, 20 mmol) in tetrahydrofuran (120 mL) slowly.
The ice-salt bath used was removed after that dropping. The reaction was complete (detected with LCMS and TLC) after stirred for 1 hour at room temperature. The mixture was cooled to 0 °C again and the reaction was quenched with water (1.14 mL) and 10percent NaOH solution (11.4 mL) respectively.
After stirred for 15 min at room temperature, the mixture was filtered and then the filter cake was washed with tetrahydrofuran (60 mL*2) and ethyl acetate EA (60 mL*2). The filtrate was dried with anhydrous sodium sulfate, filtered, concentrated, and then purified by column chromatography (elution system: petroleum ether: ethyl acetate = 10/1-4/1) to obtain a colorless oil product (2.3 g, 43percent yield). The molecular ion peak shown by liquid chromatography-mass spectrometry was: MS (ESI): m/z 246.9/248.9/250.9 [M-OH]+.
Reference: [1] Patent: EP3048103, 2016, A1, . Location in patent: Paragraph 0079; 0080
  • 3
  • [ 611-00-7 ]
  • [ 666747-06-4 ]
Reference: [1] Patent: EP3048103, 2016, A1,
[2] Organic Letters, 2018, vol. 20, # 11, p. 3310 - 3313
  • 4
  • [ 5629-98-1 ]
  • [ 666747-06-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2818 - 2841
  • 5
  • [ 615-57-6 ]
  • [ 666747-06-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2818 - 2841
  • 6
  • [ 78222-69-2 ]
  • [ 666747-06-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2818 - 2841
  • 7
  • [ 64382-92-9 ]
  • [ 666747-06-4 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 303
  • 8
  • [ 858841-41-5 ]
  • [ 666747-06-4 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 303
  • 9
  • [ 666747-06-4 ]
  • [ 98434-44-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2818 - 2841
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