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[ CAS No. 1457-93-8 ] {[proInfo.proName]}

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Chemical Structure| 1457-93-8
Chemical Structure| 1457-93-8
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Product Details of [ 1457-93-8 ]

CAS No. :1457-93-8 MDL No. :MFCD00173945
Formula : C7H6N2S Boiling Point : -
Linear Structure Formula :- InChI Key :XDQJAYFCPRWDOL-UHFFFAOYSA-N
M.W : 150.20 Pubchem ID :2781249
Synonyms :

Calculated chemistry of [ 1457-93-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.38
TPSA : 54.02 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) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 2.16
Log Po/w (WLOGP) : 2.0
Log Po/w (MLOGP) : 0.98
Log Po/w (SILICOS-IT) : 3.15
Consensus Log Po/w : 2.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.8
Solubility : 0.239 mg/ml ; 0.00159 mol/l
Class : Soluble
Log S (Ali) : -2.93
Solubility : 0.178 mg/ml ; 0.00118 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.97
Solubility : 0.162 mg/ml ; 0.00108 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 1457-93-8 ]

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

Application In Synthesis of [ 1457-93-8 ]

* 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 [ 1457-93-8 ]
  • Downstream synthetic route of [ 1457-93-8 ]

[ 1457-93-8 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 496-72-0 ]
  • [ 1457-93-8 ]
YieldReaction ConditionsOperation in experiment
82% With thionyl chloride; trimethylamine In dichloromethane for 5 h; Reflux
(1)
To a 250 mL three-neck flask were added commercial 4-methylbenzene-1,2-diamine (3.75 g, 0.03 mol), 60 mL of CH2Cl2 and, trimethylamine (13.14 g, 0.13 mol).
The solution was stirred until total dissolution of the diamine.
Sulfurous dichloride (11.47 g, 0.10 mol) was added dropwise very slowly and the mixture refluxed for 5 h.
After quenching the reaction with 1 mol/L sodium hydroxide solution, the solvent was extracted three times with dichloromethane (30 mL) and removed by rotary evaporation.
The residue was purified by silica gel column chromatography using pure petroleum ether as eluant to collect a brown needle solid, yield 3.69 g (82percent).
Mp 33-34 °C; 1H NMR (CDCl3, 400 MHz, TMS): δ 7.88 (d, 1H, J=9 Hz), 7.76 (s, 1H), 7.43 (d, 1H, J=9 Hz), 2.55 (s, 3H); 13C NMR (CDCl3, 100 MHz, TMS): δ 155.31, 153.54, 139.94, 132.41, 120.66, 119.76, 21.91; EIMS [M+] Calcd 150.0252, Found 150.0251.
82% With thionyl chloride In dichloromethane for 5 h; Inert atmosphere; Reflux To a 250 mL three-neck flask were added commercial 4- methylbenzene-1,2-diamine (3.75 g, 0.03 mol), 60 mL of CH2Cl2 and, trimethylamine (13.14 g, 0.13 mol). The solution was stirred until total dissolution of the diamine Sulfurous dichloride (11.47 g, 0.10 mol) was added dropwise very slowly and the mixture refluxed for 5 h. After quenching the reaction with 1 mol/L sodium hydroxide solution, the solvent was extracted 3 times with dichloromethane (30 mL) and removed by rotary evaporation. The residue was purified by silica gel column chromatography using pure petroleum ether as eluant to collect a brown needle solid, yield 3.69 g (82percent). m.p. 33e34 C; 1 H NMR (CDCl3, 400 MHz, TMS): d 7.88 (d, 1H, J 9 Hz), 7.76 (s, 1H), 7.43 (d, 1H, J 9 Hz), 2.55 (s, 3H); 13C NMR (CDCl3, 100 MHz, TMS): d 155.31, 153.54, 139.94, 132.41, 120.66, 119.76, 21.91; EI-MS [M] Calcd. 150.0252, Found 150.0251.
33% With thionyl chloride; triethylamine In benzene at 0℃; for 3 h; Reflux Compound 22 (4.8 g, 0.04 mol) was dissolved in the solution of benzene (150 mL) and TEA (20 mL).
To this mixture was added thionyl chloride (30 mL) at 0 °C and heated to reflux for 3 h.
When cooled to room temperature, the mixture was washed with water (100 mL), saturated sodium bicarbonate solution (100 mL) and brine (100 mL), dried with MgSO4 to obtain the crude product, which was purified by column chromatography on silica gel, eluting with ethyl acetate/petroleum (1:8) to afford product 23 (2 g, 33percent) as colorless granular crystal. Mp: 32-33 °C (lit.
Reference: [1] Tetrahedron, 2016, vol. 72, # 9, p. 1244 - 1248
[2] Tetrahedron, 2017, vol. 73, # 19, p. 2824 - 2830
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 5, p. 668 - 677
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
[5] Chemische Berichte, 1889, vol. 22, p. 2897
[6] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 2, p. 534
[7] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1967, vol. 3, p. 662 - 666[8] Khimiya Geterotsiklicheskikh Soedinenii, 1967, vol. 3, # 5, p. 839 - 844
[9] Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 629 - 633
[10] Journal of Organic Chemistry, 1962, vol. 27, p. 676 - 677
  • 2
  • [ 496-72-0 ]
  • [ 62-53-3 ]
  • [ 1457-93-8 ]
Reference: [1] Patent: CN103539760, 2016, B, . Location in patent: Paragraph 0065-0067
  • 3
  • [ 106-44-5 ]
  • [ 1457-93-8 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1985, # 11, p. 3649 - 3665
  • 4
  • [ 103-89-9 ]
  • [ 1457-93-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
  • 5
  • [ 106-49-0 ]
  • [ 1457-93-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
  • 6
  • [ 612-45-3 ]
  • [ 1457-93-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
  • 7
  • [ 89-62-3 ]
  • [ 1457-93-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
  • 8
  • [ 222851-56-1 ]
  • [ 496-72-0 ]
  • [ 1457-93-8 ]
Reference: [1] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1570,1572; engl. Ausg. S. 1643, 1645
  • 9
  • [ 1457-93-8 ]
  • [ 71605-72-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 12, p. 3163 - 3179
[2] Bulletin of the Chemical Society of Japan, 1959, vol. 32, p. 551
  • 10
  • [ 1457-93-8 ]
  • [ 89795-51-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 12, p. 3163 - 3179
[2] J. Gen. Chem. USSR (Engl. Transl.), 1964, vol. 34, p. 1270 - 1273[3] Zhurnal Obshchei Khimii, 1964, vol. 34, p. 1272 - 1276
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