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[ CAS No. 10496-18-1 ] {[proInfo.proName]}

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Chemical Structure| 10496-18-1
Chemical Structure| 10496-18-1
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Product Details of [ 10496-18-1 ]

CAS No. :10496-18-1 MDL No. :MFCD00039859
Formula : C20H42S2 Boiling Point : -
Linear Structure Formula :- InChI Key :IDJPKRIELSFBPE-UHFFFAOYSA-N
M.W :346.68 Pubchem ID :139170
Synonyms :

Calculated chemistry of [ 10496-18-1 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 19
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 113.44
TPSA : 50.6 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -1.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.86
Log Po/w (XLOGP3) : 9.91
Log Po/w (WLOGP) : 8.65
Log Po/w (MLOGP) : 6.47
Log Po/w (SILICOS-IT) : 8.27
Consensus Log Po/w : 7.83

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.98
Solubility : 0.0000364 mg/ml ; 0.000000105 mol/l
Class : Poorly soluble
Log S (Ali) : -10.9
Solubility : 0.0000000044 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -8.12
Solubility : 0.00000261 mg/ml ; 0.0000000075 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.22

Safety of [ 10496-18-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10496-18-1 ]

* 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 [ 10496-18-1 ]
  • Downstream synthetic route of [ 10496-18-1 ]

[ 10496-18-1 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 2050-77-3 ]
  • [ 10496-18-1 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; for 1.5 h; General procedure: Na2S·3H2O (0.291 g, 2.2 mmol) was addedto a magnetically stirred solution of an alkyl halide (2 mmol) and C2Cl6 or CCl4 (1.5 mmol) in PEG-200 (2 mL) at r.t. The stirring was continued until the starting halide was completely consumed (30–150 min). Next, the reaction mixture was diluted with H2O (1 mL) and extracted with EtOAc–hexane (1:1;4 × 2 mL). The organic extracts were combined, concentrated and purified by chromatography on silica gel. The desired disulfides were produced in excellent yields (Table 1).
90% at 80 - 90℃; for 2 h; Green chemistry General procedure: In a round-bottom flask (25 mL) equipped with a condenser,Europhtal (8020) catalyst solution (0.07 mL) was added to amixture of an alkyl halide (2.0 mmol), thiourea (2.2 mmol), H2O(0.1 mL), and NaHCO3 (3.0 mmol) in PEG 200 (1 mL) and themixture was stirred magnetically in an oil bath at 80-90 °C. Thestirring was continued under such conditions up to 2 h after thecomplete consumption of the starting halide. Next, the mixturewas diluted with water (0.5 mL) and extracted with 1:2 n-hexane/EtOAc (3 x 1 mL). The organic layers were decanted, combined,and concentrated to yield the crude product, which wasfurther purified by silica gel chromatography, using n-hexane aseluent.
90% With carbon disulfide; potassium cyanide In N,N-dimethyl-formamide at 20 - 60℃; for 1.75 h; General procedure: CS2 (1.3 mmol, 0.07 mL) was added to a stirred solution of KCN (1.1 mmol, 0.07 g) in DMF (1 mL) at room temperature. After 15 min, benzyl chloride (1.0 mmol, 0.11 mL) was added and the reaction mixture stirred at 60 °C. Upon reaction completion (TLC, 45 min), the mixture was cooled to room temperature, diluted with H2O (1 mL), and extracted with n-hexane/ethyl acetate (1:1, 4 × 1 mL). The combined organic extracts were dried, evaporated at 90 °C and the residue purified by silica gel column chromatography using n-hexane as eluent to give the pure dibenzyldisulfane as a white crystalline powder in 87percent (0.107 g) yield.
87% With dimethyl sulfoxide; thiourea; 1,1,1,3,3,3-hexamethyl-disilazane In water at 50℃; for 10 h; General procedure: An alkyl halide (2 mmol) and HMDS (3 mmol) were addedto a solution of thiourea (2.2 mmol) in wet DMSO (2 mLDMSO + 0.05 mL H2O). The mixture was stirred magneticallyat 50 °C for 10–24 h. Then, the mixture was dilutedwith water (2 mL) and extracted with 1:1 EtOAc/hexane(3 × 2 mL). The upper layers were decanted, combined,and concentrated. The crude product was purified by silicagel chromatography using low-boiling petroleum ether aseluent to provide the desired disulfide in high yield.

Reference: [1] Synlett, 2015, vol. 26, # 9, p. 1185 - 1190
[2] Journal of the Iranian Chemical Society, 2013, vol. 10, # 2, p. 201 - 205
[3] New Journal of Chemistry, 2016, vol. 40, # 1, p. 89 - 92
[4] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 6, p. 698 - 702
[5] Journal of Organometallic Chemistry, 2017, vol. 833, p. 10 - 17
[6] Tetrahedron Letters, 2017, vol. 58, # 45, p. 4251 - 4254
[7] Journal of the Iranian Chemical Society, 2016, vol. 13, # 1, p. 81 - 86
[8] Tetrahedron Letters, 2010, vol. 51, # 3, p. 508 - 509
  • 2
  • [ 2050-77-3 ]
  • [ 17356-08-0 ]
  • [ 10496-18-1 ]
YieldReaction ConditionsOperation in experiment
86% With tetrachloromethane; water; triethylamine In glycerol at 50℃; for 12 h; General procedure: A mixture of an alkyl halide (2 mmol), thiourea (2.5 mmol),Et3N (3.5 mmol) and CCl4 (2 mmol) in wet glycerol (2 mLglycerol + 0.1 mL H2O) was stirred magnetically at 50 °Cfor 12–24 h. Then H2O (1 mL) was added to the reactionmixture and the reaction was extracted with EtOAc(3 × 2 mL). The organic layers were decanted, combined,dried over Na2SO4, and concentrated to yield the crudedisulfide, which was further purified by silica gel chromatographyusing low-boiling petroleum ether as eluent toprovide the desired disulfides in good to excellent yields
72% With sodium carbonate In water; acetonitrile at 80℃; for 3 h; General procedure: A mixture of an alkyl halide or alkyl tosylates 1 (2 mmol), thiourea (2.2 mmol),graphene oxide (60 wtpercent), and Na2CO3 (3 mmol) in wet acetonitrile (2 mL CH3CN +0.2 mL H2O) was stirred at 80 C for 3–12 h. The progress of reaction was monitored byTLC using n-hexane. The reaction mixture was then cooled to room temperature and thegraphene oxidewas separated by simple filtration. The filtratewas evaporated under reducedpressure to get the crude product, which was further purified by silica gel chromatographyusing n-hexane as eluent to give disulfide 2 (Table 2). Characterization details of knownproducts, and graphene oxide are provided in the Supplemental Materials.
Reference: [1] Journal of the Iranian Chemical Society, 2015, vol. 12, # 8, p. 1425 - 1430
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 11, p. 1727 - 1734
  • 3
  • [ 143-10-2 ]
  • [ 10496-18-1 ]
Reference: [1] Journal of Chemical Research - Part S, 1998, # 12, p. 816 - 817
[2] Journal of Chemical Research - Part S, 1999, # 6, p. 374 - 375
[3] Journal of Chemical Research - Part S, 1998, # 8, p. 472 - 473
[4] RSC Advances, 2015, vol. 5, # 117, p. 96695 - 96704
[5] Synthetic Communications, 1997, vol. 27, # 16, p. 2783 - 2788
[6] Organic Preparations and Procedures International, 1998, vol. 30, # 3, p. 360 - 363
[7] Chemical Communications, 2016, vol. 52, # 54, p. 8448 - 8451
[8] Macromolecules, 2004, vol. 37, # 4, p. 1257 - 1270
[9] Synthetic Communications, 2002, vol. 32, # 8, p. 1151 - 1157
[10] RSC Advances, 2016, vol. 6, # 57, p. 51983 - 51988
[11] Synthetic Communications, 1996, vol. 26, # 1, p. 191 - 196
[12] Journal of Chemical Research - Part S, 1998, # 6, p. 310 - 311
[13] Journal of Organic Chemistry, 1989, vol. 54, # 13, p. 3106 - 3113
[14] Russian Chemical Bulletin, 2001, vol. 50, # 12, p. 2352 - 2355
  • 4
  • [ 5349-20-2 ]
  • [ 10496-18-1 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 47, p. 8833 - 8834
[2] Synthetic Communications, 1997, vol. 27, # 15, p. 2721 - 2724
  • 5
  • [ 29684-56-8 ]
  • [ 143-10-2 ]
  • [ 10496-18-1 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 13, p. 4989 - 4992
  • 6
  • [ 5349-20-2 ]
  • [ 10496-18-1 ]
  • [ 143-10-2 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 17, p. 3203 - 3208
  • 7
  • [ 1534-09-4 ]
  • [ 10496-18-1 ]
  • [ 143-10-2 ]
Reference: [1] Langmuir, 2010, vol. 26, # 16, p. 13221 - 13226
  • 8
  • [ 866219-37-6 ]
  • [ 10496-18-1 ]
Reference: [1] Synlett, 2005, # 12, p. 1901 - 1904
  • 9
  • [ 24566-80-1 ]
  • [ 10496-18-1 ]
Reference: [1] Synlett, 2005, # 12, p. 1901 - 1904
  • 10
  • [ 4101-68-2 ]
  • [ 10496-18-1 ]
Reference: [1] Synlett, 2005, # 12, p. 1901 - 1904
  • 11
  • [ 364329-22-6 ]
  • [ 10496-18-1 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 4, p. 1300 - 1303
  • 12
  • [ 13019-22-2 ]
  • [ 10496-18-1 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 4, p. 1300 - 1303
  • 13
  • [ 131034-47-4 ]
  • [ 10496-18-1 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 4, p. 1300 - 1303
  • 14
  • [ 213207-75-1 ]
  • [ 10496-18-1 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 4, p. 1300 - 1303
  • 15
  • [ 112-29-8 ]
  • [ 10496-18-1 ]
Reference: [1] Zhurnal Obshchei Khimii, 1951, vol. 21, p. 242,248;engl.Ausg.S.263,268
[2] Wear, 1957, vol. 1, p. 291,304
[3] Zhurnal Obshchei Khimii, 1950, vol. 20, p. 2085;engl.Ausg.S.2159
  • 16
  • [ 2050-77-3 ]
  • [ 100-44-7 ]
  • [ 150-60-7 ]
  • [ 10496-18-1 ]
Reference: [1] Synlett, 2015, vol. 26, # 9, p. 1185 - 1190
  • 17
  • [ 866219-38-7 ]
  • [ 143-10-2 ]
  • [ 866219-40-1 ]
  • [ 10496-18-1 ]
  • [ 220008-84-4 ]
Reference: [1] Synlett, 2005, # 12, p. 1901 - 1904
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