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[ CAS No. 536-33-4 ] {[proInfo.proName]}

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Chemical Structure| 536-33-4
Chemical Structure| 536-33-4
Structure of 536-33-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 536-33-4 ]

CAS No. :536-33-4 MDL No. :MFCD00057361
Formula : C8H10N2S Boiling Point : -
Linear Structure Formula :- InChI Key :AEOCXXJPGCBFJA-UHFFFAOYSA-N
M.W : 166.24 Pubchem ID :2761171
Synonyms :
2-Ethylthioisonicotinamide;NSC 255115;Bayer 5312

Calculated chemistry of [ 536-33-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.47
TPSA : 71.0 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 1.07
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 0.73
Log Po/w (SILICOS-IT) : 2.71
Consensus Log Po/w : 1.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.82
Solubility : 2.54 mg/ml ; 0.0153 mol/l
Class : Very soluble
Log S (Ali) : -2.15
Solubility : 1.17 mg/ml ; 0.00704 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.6
Solubility : 0.416 mg/ml ; 0.0025 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.63

Safety of [ 536-33-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335-H351-H361 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 536-33-4 ]

* 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 [ 536-33-4 ]
  • Downstream synthetic route of [ 536-33-4 ]

[ 536-33-4 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 536-33-4 ]
  • [ 1531-18-6 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 4, p. 747 - 748
[2] Synthesis, 1999, # 10, p. 1724 - 1726
[3] Synthetic Communications, 2000, vol. 30, # 16, p. 3047 - 3052
[4] Synthesis, 2001, # 3, p. 373 - 375
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 8, p. 722 - 723
[6] Synthetic Communications, 1999, vol. 29, # 23, p. 4235 - 4239
[7] Journal of Organic Chemistry, 1988, vol. 53, # 10, p. 2166 - 2170
[8] Chemical Communications, 2012, vol. 48, # 91, p. 11247 - 11249
  • 2
  • [ 536-33-4 ]
  • [ 1531-18-6 ]
  • [ 3376-96-3 ]
  • [ 3376-95-2 ]
  • [ 1531-16-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 37, p. 8848 - 8858
  • 3
  • [ 536-33-4 ]
  • [ 865-05-4 ]
  • [ 1531-18-6 ]
  • [ 3376-96-3 ]
  • [ 3376-95-2 ]
  • [ 1531-16-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 37, p. 8848 - 8858
  • 4
  • [ 1531-18-6 ]
  • [ 536-33-4 ]
YieldReaction ConditionsOperation in experiment
67% With sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 130℃; for 2.5 h; General procedure: Benzonitrile 1a (1 mmol), Na2S*9H2O (1.2 mmol) and DMF (1 mL) were added into a 10 mL bottle. The reactor was placed in a heating magnetic stirrer at 130 °C. After 2.5 h, by adding about 3 mL H2O after the reaction to disperse the solid product, the reaction mixture was extracted with EtOAc (3 x 3 mL), and the mixture was purified by column chromatography.
Reference: [1] RSC Advances, 2018, vol. 8, # 1, p. 170 - 175
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6572 - 6582
[3] Heterocycles, 2018, vol. 96, # 3, p. 509 - 517
[4] Bulletin de la Societe Chimique de France, 1958, p. 687,691
[5] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 915,918; engl. Ausg. S. 898
  • 5
  • [ 3376-95-2 ]
  • [ 536-33-4 ]
YieldReaction ConditionsOperation in experiment
35% With Lawessons reagent In tetrahydrofuran at 20℃; for 48 h; Inert atmosphere General procedure: THF (5ml/mmol) was added to a flask containing pyridine-4-carboxamide derivative (1 eq) at room temperature under inert atmosphere (argon) and stirring. Lawesson's reagent (1.5 eq) was added to the flask and the solution was stirred at room temperature for 48h-72h. The THF was evaporated under reduce pressure and the residue was partitioned between saturated aqueous NaHCO3 (25ml) and ethyl acetate (25ml) and extracted with ethyl acetate (2×25ml). The organic phase was dried over MgSO4 and eliminated under vacuum. The residue was further purified by flash chromatography (0–3percent MeOH:DCM, puriFlash 15-SI-HC 25G, over 45min). 5.1.3.1.1 2-ethylpyridine-4-carbothioamide (3a) Following general procedure H furnished 3a as a yellow solid, with an isolated yield of 35percent. TLC (CH2Cl2:CH3OH, 90:10 v/v): Rf=0.69; 1H NMR (300MHz, CD3OD): δ 8.47 (dd, J=5.3, 0.8Hz, 1H), 7.65 (dd, J=1.8, 0.8Hz, 1H), 7.58 (dd, J=5.3, 1.8Hz, 1H), 2.86 (q, J=7.6Hz, 2H), 1.32 (t, J=7.6Hz, 3H); 13C NMR (75MHz, CD3OD): δ 200.2, 163.6, 148.5, 148.3, 119.6, 118.6, 30.5, 13.0; IR (neat): 3258.6, 2961.5, 2932.6, 2912.0, 2875.9, 1654.8, 1593.9, 1415.6, 1392.3, 1285.6, 1260.7, 1205.4, 1149.6, 864.4, 808.4, 648.0, 528.8cm−1; HRMS (m/z): [M]+ calcd. for C8H10N2S, 167.0643; found, 167.0643.
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 6, p. 1546 - 1553
[2] European Journal of Medicinal Chemistry, 2018, vol. 159, p. 35 - 46
[3] Bulletin de la Societe Chimique de France, 1958, p. 687,691
  • 6
  • [ 100-48-1 ]
  • [ 536-33-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6572 - 6582
  • 7
  • [ 29840-73-1 ]
  • [ 536-33-4 ]
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 159, p. 35 - 46
  • 8
  • [ 1531-16-4 ]
  • [ 536-33-4 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1958, p. 687,691
  • 9
  • [ 4104-77-2 ]
  • [ 536-33-4 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1958, p. 687,691
  • 10
  • [ 156761-88-5 ]
  • [ 536-33-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 915,918; engl. Ausg. S. 898
  • 11
  • [ 50826-64-7 ]
  • [ 536-33-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 915,918; engl. Ausg. S. 898
  • 12
  • [ 4833-24-3 ]
  • [ 536-33-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 915,918; engl. Ausg. S. 898
  • 13
  • [ 38594-62-6 ]
  • [ 536-33-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 915,918; engl. Ausg. S. 898
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