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[ CAS No. 329944-72-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 329944-72-1
Chemical Structure| 329944-72-1
Chemical Structure| 329944-72-1
Structure of 329944-72-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 329944-72-1 ]

CAS No. :329944-72-1 MDL No. :MFCD08437596
Formula : C7H6BrCl Boiling Point : -
Linear Structure Formula :- InChI Key :YRIKDGJWRMHTJP-UHFFFAOYSA-N
M.W : 205.48 Pubchem ID :10774638
Synonyms :

Calculated chemistry of [ 329944-72-1 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.12
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 4.05
Log Po/w (WLOGP) : 3.41
Log Po/w (MLOGP) : 3.95
Log Po/w (SILICOS-IT) : 3.62
Consensus Log Po/w : 3.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.16
Solubility : 0.0143 mg/ml ; 0.0000694 mol/l
Class : Moderately soluble
Log S (Ali) : -3.75
Solubility : 0.0362 mg/ml ; 0.000176 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.26
Solubility : 0.0113 mg/ml ; 0.0000552 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.53

Safety of [ 329944-72-1 ]

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 [ 329944-72-1 ]

* 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 [ 329944-72-1 ]
  • Downstream synthetic route of [ 329944-72-1 ]

[ 329944-72-1 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 329944-72-1 ]
  • [ 42860-02-6 ]
Reference: [1] Journal of the Chemical Society, 1904, vol. 85, p. 1269
  • 2
  • [ 135340-78-2 ]
  • [ 329944-72-1 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With hydrogenchloride; sodium nitrite In water; acetic acid at 5 - 10℃; for 2 h;
Stage #2: With hypophosphorous acid In water; acetic acid at 0 - 20℃; for 48 h;
The amine 5 or 6 (30 mmol) was dissolved in a mixture of acetic acid (60 mL), water (25 mL) and concentrated HCl (7 mL) and cooled to 5 °C. A solution of sodium nitrite (48 mmol, 3.31 g) in water (12 mL) was added dropwise, with the temperature of the mixture kept below 5 °C. The mixture was stirred at 5-10 °C for further 2 h, then poured into 50percent solution of hypophosphorous acid, cooled to 0 °C and stirred at ambient temperature for 48 h. The mixture was extracted with dichloromethane (3×120 mL). The combined organic extracts were washed with brine (100 mL), dried over anhydrous Na2SO4 and evaporated. The residue was purified by flash column chromatography.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5568 - 5572
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
  • 3
  • [ 30273-42-8 ]
  • [ 329944-72-1 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With hydrogenchloride; sodium nitrite In water; acetic acid at 0℃; for 0.5 h;
Stage #2: With hypophosphorous acid In water; acetic acid at 0 - 20℃;
To an ice-water-cooled and stirred solution of 2-amino-5-bromo-3-chlorotoluene (12 g, 54 mmol) in a mixture of 100 mL of acetic acid, 43 mL of H2O and 11.5 mL of concentrated HCl was added dropwise a solution of NaNO2 (4.48 g, 65 mmol) in 15 mL of H2O. The reaction mixture was stirred for 30 min and was then added to an 112 mL solution of 50percent H3PO2 cooled at 0° C. After being stirred for 6 h at 0° C., the reaction mixture was allowed to stand at room temperature overnight. The solid was filtered and washed with water, then dried in vacuum. 3-Chloro-5-bromo-toluene (9 g, 81percent) was obtained as brown solid. Crystals. 1H NMR (CDCl3): δ 2.31 (s, 3H), 7.10 (s, 1H), 7.21 (s, 1H), 7.31 (s, 1H).
Reference: [1] Patent: US2006/287287, 2006, A1, . Location in patent: Page/Page column 18
[2] Journal of the Chemical Society, 1915, vol. 107, p. 849
  • 4
  • [ 1611-92-3 ]
  • [ 329944-72-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 727 - 739
  • 5
  • [ 502630-89-9 ]
  • [ 329944-72-1 ]
Reference: [1] Journal of the American Chemical Society, 2007, vol. 129, # 50, p. 15434 - 15435
  • 6
  • [ 615-65-6 ]
  • [ 329944-72-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5568 - 5572
  • 7
  • [ 614-83-5 ]
  • [ 329944-72-1 ]
Reference: [1] Journal of the Chemical Society, 1904, vol. 85, p. 1269
  • 8
  • [ 24106-05-6 ]
  • [ 329944-72-1 ]
Reference: [1] Journal of the Chemical Society, 1915, vol. 107, p. 849
  • 9
  • [ 866998-75-6 ]
  • [ 329944-72-1 ]
Reference: [1] Journal of the Chemical Society, 1915, vol. 107, p. 849
  • 10
  • [ 95-69-2 ]
  • [ 329944-72-1 ]
Reference: [1] Journal of the Chemical Society, 1915, vol. 107, p. 849
  • 11
  • [ 146948-68-7 ]
  • [ 329944-72-1 ]
Reference: [1] Journal of the Chemical Society, 1915, vol. 107, p. 849
  • 12
  • [ 99-52-5 ]
  • [ 329944-72-1 ]
Reference: [1] Journal of the Chemical Society, 1904, vol. 85, p. 1269
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