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[ CAS No. 5381-20-4 ] {[proInfo.proName]}

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Chemical Structure| 5381-20-4
Chemical Structure| 5381-20-4
Structure of 5381-20-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5381-20-4 ]

CAS No. :5381-20-4 MDL No. :MFCD00052376
Formula : C9H6OS Boiling Point : -
Linear Structure Formula :- InChI Key :WDJLPQCBTBZTRH-UHFFFAOYSA-N
M.W : 162.21 Pubchem ID :227328
Synonyms :

Calculated chemistry of [ 5381-20-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.21
TPSA : 45.31 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) : -5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 2.56
Log Po/w (WLOGP) : 2.71
Log Po/w (MLOGP) : 1.81
Log Po/w (SILICOS-IT) : 3.81
Consensus Log Po/w : 2.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.0
Solubility : 0.163 mg/ml ; 0.001 mol/l
Class : Soluble
Log S (Ali) : -3.16
Solubility : 0.112 mg/ml ; 0.000693 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.28
Solubility : 0.0851 mg/ml ; 0.000525 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 5381-20-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5381-20-4 ]

* 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 [ 5381-20-4 ]
  • Downstream synthetic route of [ 5381-20-4 ]

[ 5381-20-4 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 7342-82-7 ]
  • [ 68-12-2 ]
  • [ 5381-20-4 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 22, p. 8705 - 8710
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 17, p. 5981 - 5996
[3] Synlett, 2002, # 12, p. 2083 - 2085
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 3, p. 714 - 723
[5] Patent: CN108250058, 2018, A, . Location in patent: Paragraph 0381; 0387-0389
  • 2
  • [ 7342-82-7 ]
  • [ 201230-82-2 ]
  • [ 5381-20-4 ]
Reference: [1] Chemistry - An Asian Journal, 2012, vol. 7, # 10, p. 2213 - 2216
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 1, p. 154 - 158
  • 3
  • [ 1455-18-1 ]
  • [ 5381-20-4 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 18, p. 14547 - 14551
[2] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410
  • 4
  • [ 5312-73-2 ]
  • [ 95-15-8 ]
  • [ 5381-20-4 ]
Reference: [1] Patent: US2002/161237, 2002, A1,
  • 5
  • [ 7342-82-7 ]
  • [ 5381-20-4 ]
Reference: [1] Patent: US4659717, 1987, A,
[2] RSC Advances, 2015, vol. 5, # 22, p. 17060 - 17063
  • 6
  • [ 7342-82-7 ]
  • [ 119072-55-8 ]
  • [ 5381-20-4 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 13, p. 3492 - 3495
  • 7
  • [ 4885-02-3 ]
  • [ 95-15-8 ]
  • [ 5381-20-4 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 25, p. 3165 - 3168
[2] European Journal of Organic Chemistry, 2007, # 12, p. 1891 - 1904
  • 8
  • [ 50-00-0 ]
  • [ 95-15-8 ]
  • [ 5381-20-4 ]
  • [ 3541-37-5 ]
Reference: [1] Synlett, 2004, # 9, p. 1575 - 1576
  • 9
  • [ 95-15-8 ]
  • [ 5381-20-4 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 10, p. 2739 - 2744
[2] Journal of Organic Chemistry, 1948, vol. 13, p. 635,637
[3] Journal of Organic Chemistry, 1948, vol. 13, p. 635,637
[4] Patent: CN108250058, 2018, A,
  • 10
  • [ 3216-47-5 ]
  • [ 5381-20-4 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 10, p. 2739 - 2744
  • 11
  • [ 1196-19-6 ]
  • [ 5381-20-4 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410
  • 12
  • [ 3216-47-5 ]
  • [ 100-97-0 ]
  • [ 5381-20-4 ]
Reference: [1] Journal of Organic Chemistry, 1948, vol. 13, p. 635,637
  • 13
  • [ 917-54-4 ]
  • [ 86051-32-3 ]
  • [ 5381-20-4 ]
  • [ 24434-84-2 ]
  • [ 39857-07-3 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1983, vol. 92, # 1, p. 53 - 60
  • 14
  • [ 5381-20-4 ]
  • [ 24434-84-2 ]
YieldReaction ConditionsOperation in experiment
55% With trifluorormethanesulfonic acid; trimethylsilylazide In acetonitrile at 20℃; for 0.333333 h; Sealed tube; Inert atmosphere General procedure: To a solution of an aromatic aldehyde 1 (0.500 mmol, 1.0 equiv) and TMSN3 (115 mg, 1.00 mmol,2.0 equiv) in a premixed HFIP/ACN mixture (2.0 mL, 1:1) in a nitrogen-flushed two dram vial wasadded triflic acid (TfOH; 17.7 L, 0.200 mmol, 0.40 equiv) (exotherm and brisk effervescence due tonitrogen gas evolution was immediately observed). The vial was capped and the reaction mixture wasallowed to stir at rt for 20–75 min. The reaction mixture was concentrated under nitrogen. The residueobtained was suspended in CH2Cl2/hexanes mixture and loaded on a silica gel in a 5 g samplecartridge. Purification using a normal phase silica flash column on a CombiFlash purification systemafforded a corresponding aromatic nitrile 2 upon concentration of appropriate fractions.
Reference: [1] Molecules, 2016, vol. 21, # 1,
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 5, p. 1840 - 1840
[3] Tetrahedron Letters, 2013, vol. 54, # 17, p. 2177 - 2179
[4] Organic and Biomolecular Chemistry, 2015, vol. 13, # 30, p. 8322 - 8329
  • 15
  • [ 917-54-4 ]
  • [ 86051-32-3 ]
  • [ 5381-20-4 ]
  • [ 24434-84-2 ]
  • [ 39857-07-3 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1983, vol. 92, # 1, p. 53 - 60
  • 16
  • [ 5381-20-4 ]
  • [ 39856-98-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 3, p. 714 - 723
  • 17
  • [ 5381-20-4 ]
  • [ 1196-19-6 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 0℃; for 1 h;
Stage #2: With carbon tetrabromide; triphenylphosphine In dichloromethane for 1 h; Inert atmosphere
To a solution of l-benzothiophene-5-carbaldehyde (800 mg, 5 mmol) in MeOH (10 mL) was added sodium tetrahydroborate (0.28 g, 7.4 mmol) at 0 °C. The reaction mixture was allowed to stir at 0 °C for lh, at which point a saturated aqueous solution of H4C1 (50 mL) and water (50 mL) was added. The mixture was extracted with DCM (3x). The organic solutions were combined, dried over MgS04, filtered, and concentrated to dryness. The crude solid was then dissolved in DCM (100 mL) under argon and triphenyl phosphine (2.30 g, 8.78 mmol) and carbon tetrabromide (2.0 g, 5.9 mmol) were added. After stirring for lh, diethyl ether was added and the resulting mixture was filtered and washed with diethyl ether (2x). The filtrate was concentrated to dryness and the crude residue was purified by column chromatography to afford 5-(bromomethyl)-l-benzothiophene (760 mg, 70 percent) as a white solid. 1H MR (400 MHz, CDCI3) δ 7.80 - 7.92 (m, 2H), 7.51 (d, J=5.4 Hz, 1H), 7.41 (dd, J=8.3, 1.8 Hz, 1H), 7.35 (d, J=5.4 Hz, 1H), 4.68 (s, 2H).
Reference: [1] Patent: WO2018/89786, 2018, A1, . Location in patent: Paragraph 00376
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