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[ CAS No. 57381-37-0 ] {[proInfo.proName]}

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Chemical Structure| 57381-37-0
Chemical Structure| 57381-37-0
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Product Details of [ 57381-37-0 ]

CAS No. :57381-37-0 MDL No. :MFCD08445660
Formula : C7H3BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :CTSHRMBLMKPDAG-UHFFFAOYSA-N
M.W : 216.46 Pubchem ID :10330944
Synonyms :

Calculated chemistry of [ 57381-37-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.87
TPSA : 23.79 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) : -5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 2.97
Log Po/w (MLOGP) : 2.79
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.49
Solubility : 0.0699 mg/ml ; 0.000323 mol/l
Class : Soluble
Log S (Ali) : -3.12
Solubility : 0.163 mg/ml ; 0.000754 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.96
Solubility : 0.0238 mg/ml ; 0.00011 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 57381-37-0 ]

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 [ 57381-37-0 ]

* 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 [ 57381-37-0 ]
  • Downstream synthetic route of [ 57381-37-0 ]

[ 57381-37-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 925-90-6 ]
  • [ 57381-37-0 ]
  • [ 22246-02-2 ]
YieldReaction ConditionsOperation in experiment
34.6%
Stage #1: at 0 - 5℃; for 5 h; Inert atmosphere
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 16 h; Inert atmosphere
To a stirred solution of 2-bromo-5-chlorobenzonitrile (80 g, 370 mmol) in THF (1000 mL) at 0°C was added EtMgBr (370 mL, 1110 mmol) dropwise. The reaction mixture was stilTed at 0-5°C for 5 hours before MeOH (500 mL) was added dropwise. After the solution was stilTed for another 15 mm, NaBH4 (28 g, 740 mmol) was added carefully and the resulting mixture was stirred at room temperature for 16 hours. The reaction solution was then poured into water and exacted with EtOAc (3 x 200 mL). The combined organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crudeproduct, which was purified by column chromatography (petroleum ether: EtOAc =3: 1) to afford the title compound (30 g, 34.6percent) as yellowish oil. MS: 235.5 [M+H’i.
Reference: [1] Patent: WO2014/191340, 2014, A1, . Location in patent: Page/Page column 37; 38
  • 2
  • [ 766-84-7 ]
  • [ 57381-37-0 ]
YieldReaction ConditionsOperation in experiment
63% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid In trifluoroacetic acid at 24 - 31℃; for 6.13333 h; An alternative synthesis of compound 1-2 follows: To a solution of 3-chlorobenzonitrile 1-1 (50 g, 360 mmol) in trifluoroacetic acid (180 mL) was added sulfuric acid (24 mL) and then 1,3-dibromo-5,5-dimethylhydantoin (67 g, 234 mmol) in portions over 8 minutes. The reaction temperature was allowed to reach 31° C. and then cooling was applied to bring the temperature to 24° C. After a 6 hour age, the heterogeneous reaction was cooled to 10° C. and water (250 mL) was added. Following a 10 minute age, the reaction was filtered and the product cake was washed twice with water (250 and 100 mL) to afford a white solid (52.4 g, 63percent). 1H NMR (CDCl3, 400 MHz) 6 7.64-7.62 (m, 2H), 7.44 (dd, J=8.6, 2.5 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ134.2, 134.1, 133.9, 133.8, 123.3, 117.2, 115.8
Reference: [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 9, p. 3026 - 3035
[2] Tetrahedron, 2004, vol. 60, # 50, p. 11367 - 11374
[3] Organic Letters, 2006, vol. 8, # 18, p. 3903 - 3906
[4] Patent: US2004/181070, 2004, A1, . Location in patent: Page 11
[5] Patent: US2004/181070, 2004, A1, . Location in patent: Page 11
  • 3
  • [ 21739-93-5 ]
  • [ 124-63-0 ]
  • [ 57381-37-0 ]
Reference: [1] Patent: US5130318, 1992, A,
  • 4
  • [ 174265-12-4 ]
  • [ 57381-37-0 ]
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 29, p. 2844 - 2847
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7959 - 7963
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