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[ CAS No. 63837-11-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 63837-11-6
Chemical Structure| 63837-11-6
Chemical Structure| 63837-11-6
Structure of 63837-11-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 63837-11-6 ]

CAS No. :63837-11-6 MDL No. :MFCD00603096
Formula : C8H6BrNS Boiling Point : -
Linear Structure Formula :- InChI Key :OLQKNZNXLBILDD-UHFFFAOYSA-N
M.W : 228.11 Pubchem ID :3017457
Synonyms :

Calculated chemistry of [ 63837-11-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.29
TPSA : 41.13 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) : -5.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.48
Log Po/w (XLOGP3) : 3.47
Log Po/w (WLOGP) : 3.37
Log Po/w (MLOGP) : 2.58
Log Po/w (SILICOS-IT) : 4.27
Consensus Log Po/w : 3.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.05
Solubility : 0.0205 mg/ml ; 0.00009 mol/l
Class : Moderately soluble
Log S (Ali) : -4.02
Solubility : 0.022 mg/ml ; 0.0000964 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.22
Solubility : 0.0139 mg/ml ; 0.0000608 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.09

Safety of [ 63837-11-6 ]

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 [ 63837-11-6 ]

* 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 [ 63837-11-6 ]
  • Downstream synthetic route of [ 63837-11-6 ]

[ 63837-11-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 120-75-2 ]
  • [ 63837-11-6 ]
  • [ 5304-21-2 ]
  • [ 112146-10-8 ]
Reference: [1] Heterocycles, 2011, vol. 83, # 6, p. 1267 - 1274
  • 2
  • [ 63837-11-6 ]
  • [ 557-21-1 ]
  • [ 90418-93-2 ]
YieldReaction ConditionsOperation in experiment
93% at 80℃; for 16 h; Commercially available 5-bromo-2-methylbenzothiazole (1.42 g), zinc(II) cyanide (584 mg) and tetrakis(triphenylphosphine)palladium(0) (360 mg) were dissolved in dry DMF (12 mL), degassed and stirred at 80° C. under argon. After 16 h the mixture was evaporated and diluted with chloroform. The solution was washed with 1N hydrochloric acid, 1N sodium hydroxide and brine, dried (MgSO4) and absorbed on silica. Purification by column chromatography (cyclohexane/EtOAc, 8:2 to 7:3) afforded the intermediate (1.01 g; 93percent) as bright yellow needles.
Reference: [1] Patent: US2006/173183, 2006, A1, . Location in patent: Page/Page column 97
  • 3
  • [ 63837-11-6 ]
  • [ 90418-93-2 ]
Reference: [1] Patent: US5576343, 1996, A,
  • 4
  • [ 63837-11-6 ]
  • [ 124-38-9 ]
  • [ 584-08-7 ]
  • [ 24851-69-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13426 - 13430[2] Angew. Chem., 2017, vol. 129, p. 13611 - 13615,5
  • 5
  • [ 398132-82-6 ]
  • [ 63837-11-6 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 36, p. 14760 - 14763
[2] Organic Letters, 2011, vol. 13, # 18, p. 4974 - 4976
[3] Journal of the American Chemical Society, 2010, vol. 132, # 40, p. 14076 - 14078
  • 6
  • [ 32770-99-3 ]
  • [ 63837-11-6 ]
YieldReaction ConditionsOperation in experiment
52% at 0℃; for 2 h; Step A: Sodium nitrite (0.9 g, 13 mmol) was added portionwise to a suspension of 2-methyl-5-aminobenzothiazole dihydrochloride (2.0 g, 8 mmol) in hydrobromic acid (24 ml) at 0° C. The resulting mixture was added dropwise to a solution of copper(I) bromide (4.0 g, 14 mmol) in hydrobromic acid (50 ml) at 0° C. After stirring at 0° C. for 2 hours, water was added. The reaction mixture was basified to pH 9 using aqueous ammonium hydroxide and was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate to give 2-methyl-5-bromobenzothiazole (1.0 g, 52percent, 82percent AUC GC) after chromatography (9:1 heptane/ethyl acetate): 1H NMR (300 MHz, DMSO-d6) δ 8.12 (d, J=1.8 Hz, 8.02 (dd,1H) J=8.4, 1.5 Hz, 1H), 7.56 (dd, J=8.7, 2.1 Hz, 1H), 2.81 (s, 3H).
Reference: [1] Patent: US2006/52378, 2006, A1, . Location in patent: Page/Page column 108
  • 7
  • [ 110704-51-3 ]
  • [ 63837-11-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 1, p. 108 - 122
  • 8
  • [ 25462-66-2 ]
  • [ 63837-11-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 1, p. 108 - 122
  • 9
  • [ 29452-12-8 ]
  • [ 63837-11-6 ]
  • [ 110704-32-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 1, p. 108 - 122
  • 10
  • [ 3460-18-2 ]
  • [ 63837-11-6 ]
Reference: [1] Russian Journal of Organic Chemistry, 1996, vol. 32, # 12, p. 1803 - 1811
  • 11
  • [ 120-75-2 ]
  • [ 63837-11-6 ]
  • [ 5304-21-2 ]
  • [ 112146-10-8 ]
Reference: [1] Heterocycles, 2011, vol. 83, # 6, p. 1267 - 1274
  • 12
  • [ 76209-05-7 ]
  • [ 108-24-7 ]
  • [ 63837-11-6 ]
Reference: [1] Russian Journal of Organic Chemistry, 1996, vol. 32, # 12, p. 1803 - 1811
  • 13
  • [ 120-75-2 ]
  • [ 63837-11-6 ]
  • [ 5304-21-2 ]
  • [ 112146-10-8 ]
Reference: [1] Heterocycles, 2011, vol. 83, # 6, p. 1267 - 1274
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