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[ CAS No. 62266-82-4 ] {[proInfo.proName]}

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Chemical Structure| 62266-82-4
Chemical Structure| 62266-82-4
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Product Details of [ 62266-82-4 ]

CAS No. :62266-82-4 MDL No. :MFCD00239363
Formula : C7H4BrNOS Boiling Point : -
Linear Structure Formula :- InChI Key :HECJMTPEVWQFCY-UHFFFAOYSA-N
M.W : 230.08 Pubchem ID :188444
Synonyms :

Calculated chemistry of [ 62266-82-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.15
TPSA : 61.1 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) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.73
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 2.35
Log Po/w (MLOGP) : 2.07
Log Po/w (SILICOS-IT) : 3.97
Consensus Log Po/w : 2.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.42
Solubility : 0.0884 mg/ml ; 0.000384 mol/l
Class : Soluble
Log S (Ali) : -3.38
Solubility : 0.0967 mg/ml ; 0.00042 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.74
Solubility : 0.0423 mg/ml ; 0.000184 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 62266-82-4 ]

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 [ 62266-82-4 ]

* 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 [ 62266-82-4 ]
  • Downstream synthetic route of [ 62266-82-4 ]

[ 62266-82-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 62266-82-4 ]
  • [ 80945-86-4 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With trichlorophosphate In N,N-dimethyl-formamide at 100℃;
Stage #2: With potassium carbonate In water; N,N-dimethyl-formamide at 20 - 35℃; for 1 h;
DMF (0.807 mL, 10.4 mmol) was added to phosphorous oxychloride (8.10 mL, 86.9 mmol), and the reaction mixture was stirred for 15 min. 6- bromobenzo[dlthiazol-2(3H)-one (2.00 g, 8.69 mmol) was added and the reaction mixture was heated to 100 0C overnight. Upon cooling to rt, the reaction mixture was slowly added to a solution OfKaCO3 (75 g) in water (200 mL) while maintaining the temperature below 35 0C. Additional K2CO3 was added in order <n="90"/>to maintain the pH above 10. Upon complete addition, the mixture was allowed to stir for 1 h. The solid was collected by filtration, washed with water (2 x 25 mL), and air dried. Further drying in a vacuum oven gave 2.06 g (95percent) of the desired product as a brown solid. The material was used without further purification. LC- MS: RT = 9.94 min., compound does not ionize.
83% for 18 h; Reflux A solution of 6-bromobenzothiazolin-2-one (500 mg, 2.2 mmol) in POCI3 (5 mE) was refluxed during 18 h, then poured onto ice. The solution was neutralized to pH 9 by addition of NH4OH, and the resulting solid collected by filtration. Washing with water and drying in vacuo gave 6-bromo-2-chlorobenzothiazole (450 mg, 83percent).
Reference: [1] Patent: WO2007/146066, 2007, A2, . Location in patent: Page/Page column 88-89
[2] Patent: US2015/368278, 2015, A1, . Location in patent: Paragraph 1050
  • 2
  • [ 934-34-9 ]
  • [ 62266-82-4 ]
YieldReaction ConditionsOperation in experiment
90% With bromine In dichloromethane at 20℃; for 3 h; Bromine (5.1mL, 99.2mmol) is added dropwise to a solution of 3H-benzothiazol-2-one 7 (5g, 33,1mmol) in DCM (200mL) and the reaction mixture is stirred for 3h at room temperature. The precipitate is filtered, washed with diethyl ether and dried, yielding 8 as a white powder (6.85g, 90percent); C7H4BrNOS; MW=230.1g/mol; mp 229–231°C. 1H NMR (300MHz, CDCl3): δ 7,03 (d, 1H, J=8,9Hz); 7,43 (dd, 1H, J=1.7Hz, 8,9Hz); 7,85 (d, 1H, J=1,7Hz). MS (ESI+) m/z 229.8 [M+H79Br ]+, 231.7 [M+H81Br ]+.
Reference: [1] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1503 - 1509
[2] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 310 - 326
[3] Monatshefte fur Chemie, 2011, vol. 142, # 1, p. 67 - 80
[4] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 807 - 817
[5] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1944, vol. 5, p. 11,14, 16, 18
[6] Journal of the Chemical Society, 1930, p. 125,145
[7] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 575 - 582
  • 3
  • [ 66416-72-6 ]
  • [ 68-12-2 ]
  • [ 62266-82-4 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 12, p. 6090 - 6093
  • 4
  • [ 408328-13-2 ]
  • [ 62266-82-4 ]
Reference: [1] Journal of Organic Chemistry, 1953, vol. 18, p. 1092,1099
  • 5
  • [ 615-20-3 ]
  • [ 62266-82-4 ]
Reference: [1] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1944, vol. 5, p. 11,14, 16, 18
  • 6
  • [ 80945-86-4 ]
  • [ 62266-82-4 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 125,145
  • 7
  • [ 941-57-1 ]
  • [ 62266-82-4 ]
Reference: [1] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1944, vol. 5, p. 11,14, 16, 18
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