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[ CAS No. 608-33-3 ] {[proInfo.proName]}

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Chemical Structure| 608-33-3
Chemical Structure| 608-33-3
Structure of 608-33-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 608-33-3 ]

CAS No. :608-33-3 MDL No. :MFCD00002152
Formula : C6H4Br2O Boiling Point : -
Linear Structure Formula :- InChI Key :SSIZLKDLDKIHEV-UHFFFAOYSA-N
M.W :251.90 Pubchem ID :11847
Synonyms :
2,6-Dibromophenol

Calculated chemistry of [ 608-33-3 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.87
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
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) : -5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 3.36
Log Po/w (WLOGP) : 2.92
Log Po/w (MLOGP) : 2.99
Log Po/w (SILICOS-IT) : 2.74
Consensus Log Po/w : 2.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.01
Solubility : 0.0245 mg/ml ; 0.0000973 mol/l
Class : Moderately soluble
Log S (Ali) : -3.46
Solubility : 0.0868 mg/ml ; 0.000345 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.53
Solubility : 0.0742 mg/ml ; 0.000294 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.28

Safety of [ 608-33-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 608-33-3 ]

* 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 [ 608-33-3 ]
  • Downstream synthetic route of [ 608-33-3 ]

[ 608-33-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 608-33-3 ]
  • [ 3722-78-9 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2219 - 2222
  • 2
  • [ 608-33-3 ]
  • [ 917-54-4 ]
  • [ 576-26-1 ]
  • [ 13319-71-6 ]
  • [ 32750-14-4 ]
  • [ 95-48-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2617 - 2625
  • 3
  • [ 608-33-3 ]
  • [ 74-88-4 ]
  • [ 38603-09-7 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With potassium carbonate In acetone at 20℃; for 0.5 h;
Stage #2: at 60℃; for 3 h;
Example 1
Preparation of 2,6-Dibromo-4-(6-(3-bromobenzyloxy)pyridazin-3-yl)phenol (compound 91)
To a stirred solution of 2,6-dibromophenol (5.26 g, 20.9 mmol) in acetone (170 mL) was added anhydrous potassium carbonate (4.33 g, 31.3 mmol) and the mixture was stirred at room temperature for 30 min.
Iodomethane (1.97 mL, 31.4 mmol) was then added and the mixture was heated at 60° C. for 3 h.
The mixture was filtered and the filtrate was evaporated.
The residue was partitioned between petroleum ether (40-60° C., 100 mL) and water (100 mL).
The aqueous layer was further extracted with petroleum ether (40-60° C., 100 mL) and the combined organic extracts were washed with brine (50 mL), dried (MgSO4) and evaporated to leave 5.43 g (98percent) of the title compound as a colorless oil. 1H NMR δ (ppm)(CDCl3): 3.89 (3H, s), 6.86 (1H, t, J=8.02 Hz), 7.50 (2H, d, J=8.01 Hz).
92%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere
Stage #2: at 20℃;
21.2) 2,6-dibromo-methoxy-benzene (intermediate 66); To a solution of 2,6-dibromo-phenol (30 g, 119.09 mmol) in DMF (160 ml) at O0C was added NaH (60percent, 5.72 g, 142.91 mmol) portionwise under argon. After 30 min methyl iodide (7.78 ml, 125.05 mmol) was added dropwise and the reaction mixture was stirred for 4 h at RT. The mixture was diluted with ethyl acetate (100 ml), washed with water (2x 200 ml) and brine (100 ml), dried over Na2SO4, and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel (eluent: AcOEt/cyclohexane 1/4). Yield: 29.08 g, 92 percent
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 33, p. 4912 - 4914
[2] Patent: US2009/270398, 2009, A1, . Location in patent: Page/Page column 35
[3] Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17371 - 17375
[4] Journal of the American Chemical Society, 2016, vol. 138, # 31, p. 9779 - 9782
[5] Patent: WO2009/103440, 2009, A1, . Location in patent: Page/Page column 75
[6] Journal of the American Chemical Society, 2011, vol. 133, # 34, p. 13317 - 13319
[7] Advanced Synthesis and Catalysis, 2008, vol. 350, # 13, p. 2024 - 2032
  • 4
  • [ 608-33-3 ]
  • [ 38603-09-7 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate; dimethyl sulfate In n-heptane; ethyl acetate; acetonitrile 2,6-Dibromoanisole (1):
A mixture of 2,6-dibromophenol (25 g, 0.099 mol), powder potassium carbonate (28 g, 0.2 mol, 2 equiv) and dimethyl sulfate (12.6 g, 0.099 mol) in acetonitrile (400 mL) was kept at reflux with good stirring for 4 hr.
After cooling, the solids were removed by filtration and the solvent was removed in a rotary evaporator.
The residue was taken in 2:1 heptane/ethyl acetate mixture (800 mL) and washed with water (2*400 mL).
The organic layer was dried over sodium sulfate, filtered and the solvent was removed in a rotary evaporator, leaving almost pure 1 (15.5 g, 96percent).
Reference: [1] Patent: US2011/98425, 2011, A1,
[2] Journal of Applied Chemistry, 1956, vol. 6, p. 125,126
  • 5
  • [ 608-33-3 ]
  • [ 77-78-1 ]
  • [ 38603-09-7 ]
Reference: [1] Journal of the American Chemical Society, 1932, vol. 54, p. 1465,1468
[2] Journal of Organic Chemistry, 1966, vol. 31, p. 3666 - 3671
  • 6
  • [ 608-33-3 ]
  • [ 292638-85-8 ]
  • [ 33491-30-4 ]
Reference: [1] Heterocyclic Communications, 2010, vol. 16, # 2-3, p. 113 - 120
  • 7
  • [ 608-33-3 ]
  • [ 196799-45-8 ]
Reference: [1] Advanced Synthesis and Catalysis, 2007, vol. 349, # 1-2, p. 193 - 203
[2] Tetrahedron Letters, 2000, vol. 41, # 14, p. 2269 - 2273
  • 8
  • [ 608-33-3 ]
  • [ 206347-30-0 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 15, p. 2219 - 2222
  • 9
  • [ 608-33-3 ]
  • [ 327183-32-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2007, vol. 349, # 1-2, p. 193 - 203
[2] Chemistry - A European Journal, 2015, vol. 21, # 29, p. 10322 - 10325
[3] Patent: WO2008/82488, 2008, A1,
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