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[ CAS No. 19362-77-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 19362-77-7
Chemical Structure| 19362-77-7
Chemical Structure| 19362-77-7
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Quality Control of [ 19362-77-7 ]

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Product Details of [ 19362-77-7 ]

CAS No. :19362-77-7 MDL No. :MFCD00142119
Formula : C12H10S3 Boiling Point : -
Linear Structure Formula :- InChI Key :JLLMOYPIVVKFHY-UHFFFAOYSA-N
M.W : 250.40 Pubchem ID :619483
Synonyms :

Calculated chemistry of [ 19362-77-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.51
TPSA : 102.9 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.85
Log Po/w (XLOGP3) : 3.84
Log Po/w (WLOGP) : 4.42
Log Po/w (MLOGP) : 4.95
Log Po/w (SILICOS-IT) : 4.14
Consensus Log Po/w : 4.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.27
Solubility : 0.0134 mg/ml ; 0.0000535 mol/l
Class : Moderately soluble
Log S (Ali) : -5.7
Solubility : 0.000503 mg/ml ; 0.00000201 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.25
Solubility : 0.0014 mg/ml ; 0.00000561 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.95

Safety of [ 19362-77-7 ]

Signal Word:Danger Class:9
Precautionary Statements:P264-P270-P273-P280-P301+P312-P305+P351+P338 UN#:3077
Hazard Statements:H302-H318-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 19362-77-7 ]

* 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.

  • Downstream synthetic route of [ 19362-77-7 ]

[ 19362-77-7 ] Synthesis Path-Downstream   1~101

  • 2
  • [ 79-01-6 ]
  • [ 19362-77-7 ]
  • di<4-(2,2-dichlorovinylthio)phenyl> sulfide [ No CAS ]
  • 3
  • [ 19362-77-7 ]
  • [ 107-06-2 ]
  • [ 152419-82-4 ]
YieldReaction ConditionsOperation in experiment
With tetrabutyl-ammonium chloride; potassium hydroxide; at 23℃; To synthesize bis(4-vinylthiophenyl)sulfide, 4,4?- thiobis(benzenethiol) was first reacted with an excess of 1 ,2-dichloroethane in the presence of KOH and tetrabutylammonium chloride at room temperature (23 C.). The bis[4-(2-chloroethylthiophenyl)sulfide obtained was dehydrohalogenated with KOH in water at 85 C. to form bis(4-vinylthiophenyl)sulfide. Bis(4-vinylthiophenyl)sulfide was obtained as a colourless, low-viscosity liquid at room temperature, with a viscosity of only 17 mPa s (23 C.). The refractive index n is 1.695 and the polymerization shrinkage AV is -7.8 vol.-%. The polymerization shrinkage was measured in accordance with DIN 13907: ?Dentistry:Polymerization shrinkage of filling materials?.
  • 6
  • [ 19362-77-7 ]
  • 1,3-di(carbazol-9-yl)-1-diphenylamino-2-propanol glycidyl ether [ No CAS ]
  • bis<4-<7-(carbazol-9-yl)-6-(diphenylamino-N-methyl)-3-hydroxy-5-oxa-1-thioheptyl>phenyl>sulphide [ No CAS ]
  • 7
  • [ 19362-77-7 ]
  • [ 82684-71-7 ]
  • bis<4-<6-(carbazol-9-methyl)-7-(carbazol-9-yl)-3-hydroxy-5-oxa-1-thioheptyl>phenyl>sulphide [ No CAS ]
  • 8
  • [ 19362-77-7 ]
  • tetraisopropyl 2,2'-dithiodi(phenylphosphonate) [ No CAS ]
  • tetraisopropyl 2,2'-dimercapto-5,5'-thiodi(phenylphosphonate) [ No CAS ]
  • 9
  • [ 19362-77-7 ]
  • [ 2574-25-6 ]
  • O,O,O',O',-tetraisopropyl S,S'-(thiodi-4,1-phenylene) bis(phosphorothioate) [ No CAS ]
  • 10
  • [ 37860-51-8 ]
  • [ 19362-77-7 ]
  • 10,13,16-Trioxa-2,7,19-trithia-tricyclo[18.2.2.23,6]hexacosa-1(23),3(26),4,6(25),20(24),21-hexaene [ No CAS ]
  • 11
  • [ 5197-62-6 ]
  • [ 19362-77-7 ]
  • 2-(2-{2-[4-(4-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethylsulfanyl}-phenylsulfanyl)-phenylsulfanyl]-ethoxy}-ethoxy)-ethanol [ No CAS ]
  • 12
  • [ 19362-77-7 ]
  • [ 77544-60-6 ]
  • 2-{2-[2-(2-{4-[4-(2-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethoxy}-ethylsulfanyl)-phenylsulfanyl]-phenylsulfanyl}-ethoxy)-ethoxy]-ethoxy}-ethanol [ No CAS ]
  • 13
  • [ 19362-77-7 ]
  • [ 134881-77-9 ]
  • C34H44O8S3 [ No CAS ]
  • 14
  • [ 19362-77-7 ]
  • 2-(2-{2-[4-(4-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethylsulfanyl}-phenylsulfanyl)-phenylsulfanyl]-ethoxy}-ethoxy)-ethanol [ No CAS ]
  • C36H40O4S6 [ No CAS ]
  • 15
  • [ 19362-77-7 ]
  • 2-{2-[2-(2-{4-[4-(2-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethoxy}-ethylsulfanyl)-phenylsulfanyl]-phenylsulfanyl}-ethoxy)-ethoxy]-ethoxy}-ethanol [ No CAS ]
  • C40H48O6S6 [ No CAS ]
  • 16
  • [ 19362-77-7 ]
  • [ 106-93-4 ]
  • 1,2,9,14,17,22-hexathia[1.4.1.4]paracyclophane [ No CAS ]
  • 17
  • [ 19362-77-7 ]
  • [ 111-44-4 ]
  • C32H32O2S6 [ No CAS ]
  • 18
  • [ 19362-77-7 ]
  • [ 19249-03-7 ]
  • 10,13-Dioxa-2,7,16-trithia-tricyclo[15.2.2.23,6]tricosa-1(20),3(23),4,6(22),17(21),18-hexaene [ No CAS ]
  • 19
  • [ 19362-77-7 ]
  • [ 100-44-7 ]
  • [ 103677-18-5 ]
  • 20
  • [ 19362-77-7 ]
  • [ 104-82-5 ]
  • [ 103677-20-9 ]
  • 21
  • [ 19362-77-7 ]
  • [ 74-88-4 ]
  • 4-(4-methylsulfanyl-phenylsulfanyl)-benzenethiol [ No CAS ]
  • 22
  • [ 19362-77-7 ]
  • [ 74-88-4 ]
  • [ 125877-23-8 ]
  • 23
  • [ 19362-77-7 ]
  • [ 325963-57-3 ]
  • poly(thiophenylene)(N,N'-diphenyl-1,4-phenylenediamine), molecular weight 5.4E3, temperature 10% weight loss 362 deg C, temperature glass transition 131 deg C [ No CAS ]
  • 24
  • [ 19362-77-7 ]
  • [ 21615-34-9 ]
  • (C6H4(OCH3)COSC6H4)2S [ No CAS ]
  • 25
  • [ 861224-37-5 ]
  • [ 19362-77-7 ]
  • [ 861224-35-3 ]
  • 26
  • di((4-(diphenylamino)iminomethyl)phenyl)-4-(2,3-epoxypropyl)oxyphenylamine [ No CAS ]
  • [ 19362-77-7 ]
  • di(4-(4-(di((4-(diphenylamino)iminomethyl)phenyl)amino)phenyl)oxy-2-hydroxypropylthio)phenylsulfide [ No CAS ]
  • 27
  • 3,6-bis(diphenylamino)-9-(4-(2,3-epoxypropyl)phenyloxy)carbazole [ No CAS ]
  • [ 19362-77-7 ]
  • di(4-(4-(3,6-di(N,N-diphenylamino)carbazole-9-yl)phenyloxy-2-hydroxypropylthio)phenyl)sulphide [ No CAS ]
  • 28
  • 1,6-di(carbazol-9-yl)-5-(1-carbazol-9-ylmethyl)-4-oxa-2-hexanol glycidyl ether [ No CAS ]
  • [ 19362-77-7 ]
  • 4,4'-bis[10-(carbazol-9-yl)-6,9-(1-carbazol-9-ylmethyl)-3 hydroxy-5,8-dioxa-1-thia]thiobisbenzene [ No CAS ]
  • 29
  • [ 1035221-52-3 ]
  • [ 19362-77-7 ]
  • C68H56O8N2S3 [ No CAS ]
  • 31
  • [ 19362-77-7 ]
  • 4,4'-bis(3-nitro-5-phenylsulfonylphenylsulfonyl)diphenyl sulfone [ No CAS ]
  • 33
  • [ 19362-77-7 ]
  • bis[4-(4-methylbenzylsulfinyl)phenyl]sulfide [ No CAS ]
  • 34
  • [ 19362-77-7 ]
  • [ 337984-50-6 ]
  • 36
  • [ 19362-77-7 ]
  • [ 337984-51-7 ]
  • 37
  • [ 19362-77-7 ]
  • C36H40O4S6 [ No CAS ]
  • 38
  • [ 19362-77-7 ]
  • C40H48O6S6 [ No CAS ]
  • 40
  • [ 19362-77-7 ]
  • di<4-(2,2-dichlorovinylsulfinyl)phenyl> sulfoxide [ No CAS ]
  • 43
  • Au55(triphenylphosphine)12Cl6 [ No CAS ]
  • [ 19362-77-7 ]
  • 2Au55*22S(C6H4S)2=[(Au55)2(S(C6H4S)2)22] [ No CAS ]
  • 44
  • Au55(triphenylphosphine)12Cl6 [ No CAS ]
  • [ 19362-77-7 ]
  • 2Au55*14(S(C6H4S)2)2=[(Au55)2((S(C6H4S)2)2)14] [ No CAS ]
  • 45
  • [ 72428-60-5 ]
  • [ 19362-77-7 ]
  • [ 2966-50-9 ]
  • [ 909123-22-4 ]
  • 46
  • [ 37095-27-5 ]
  • [ 19362-77-7 ]
  • [ 2966-50-9 ]
  • [ 909123-20-2 ]
  • 47
  • [ 18024-34-5 ]
  • [ 19362-77-7 ]
  • [ 2966-50-9 ]
  • [ 909123-21-3 ]
  • 48
  • [ 99396-97-1 ]
  • [ 19362-77-7 ]
  • [ 2966-50-9 ]
  • [S(C6H4SAu)2(μ-trans-Ph2PCHCHPPh2)] [ No CAS ]
  • 49
  • [ 64659-16-1 ]
  • [ 19362-77-7 ]
  • [ 2966-50-9 ]
  • [ 909123-25-7 ]
  • 50
  • [ 99350-05-7 ]
  • [ 19362-77-7 ]
  • [ 2966-50-9 ]
  • [ 909123-24-6 ]
  • 51
  • [ 63640-04-0 ]
  • [ 19362-77-7 ]
  • [ 2966-50-9 ]
  • [ 909123-23-5 ]
  • 52
  • [ 19362-77-7 ]
  • [ 107-07-3 ]
  • [ 133921-80-9 ]
YieldReaction ConditionsOperation in experiment
90% Example 54,4'-Bis(methacryloyloxyethylthio)diphenylsulfide4,4'-(Thiophenyl)sulfide (100 g; 0.4 moles; available from Sumitomo Seika) is added to a solution of NaOH (32 g; moles) in water (200 ml). The mixture is warmed up to 600C and stirred for an additional 1 h until a clear solution. 2-Chloroethanol (70 g; 0.87 moles) is added dropwise for 1.5h alongside with more water (100 ml). After the addition is complete, the reaction mixture is stirred at 600C for another 1.5 hours, cooled to room temperature and filtered to give 4,4'- bis(hydroxyethylthiophenyl)sulfide as pure, white crystals (121 g; yield 90%). 1H NMR (CDCI3, delta ppm) 7.32 (d, 4H), 7.25 (d, 4H), 3.78 (t, 4H), 3.13 (t, 4H), 1.78 (s, broad, 2H).4,4'-Bis(hydroxyethylthiophenyl)sulfide (100 g; 0.3 moles), methyl methacrylate (100 g; 1 mole), and 2,4-dimethyl-6-terf-butyl-phenol (0.1 g) are charged in a reactor and dried by azeotropically <n="37"/>distilling the water with cyclohexane until the water content of the reaction mixture is less then 500 ppm. Titanium /so-propoxide (2 g) is added and the reaction is advanced by heating at 90- 92C and continuously removing the methanol/cyclohexane azeotrope using a rectifying column until the desired conversion is achieved. Throughout the drying process and transesterification reaction, a steady stream of air is supplied to the reaction vessel as an additional polymerization inhibitor. The reaction mixture is then vacuum distilled to remove excess methyl methacrylate and cyclohexane, and mixed vigorously for 2h with 20 ml water at 50C. The resulting white titanium oxide precipitate is filtered to leave behind the desired product as a clear, light-yellow liquid (120 g; yield 90%; nD251.6097). 1H NMR (CDCI3, delta ppm) 7.32 (d, 4H), 7.23 (d, 4H), 6.06 (d, 2H), 5.56 (d, 4H), 4.31 (t, 4H), 3.12 (t, 4H), 1.91 (s, 6H).
  • 53
  • [ 19362-77-7 ]
  • [ 122-60-1 ]
  • [ 1048373-73-4 ]
YieldReaction ConditionsOperation in experiment
90% boron trifluoride diethyl etherate; at 110℃; for 6h; Example 74,4'-Bis[2-(phenyloxymethyl)-2-(methacryloyloxy)ethylthio]diphenylsulfide <n="38"/>4,4'-(Thiophenyl)sulfide (12.6 g; 0.05 moles) is added to phenyl glycidyl ether (15 g; 0.1 moles) and heated to 1100C when it became a clear liquid. The mixture is kept at 1100C for about 6h during which time several drops of BF3chietherate 48% are added every one hour to catalyze the epoxide ring opening. Upon completion of reaction, the crude is cooled to room temperature to give 4,4'-bis[2-(phenyloxymethyl)-2-(hydroxy)ethylthio]diphenylsulfide as a grey-white solid (25 g; yield 90%). 1H NMR (CDCI3, delta ppm) 7.25 (m, 12H), 6.96 (t, 2H), 6.85 (d, 4H), 4.10 (m, 8H), 3.20 (ddd, 2H), 1.35 (s, broad, 2H).Methacryloyl chloride (11 g of 97% purity; 107 mmoles) is added dropwise to a solution of 4,4'- bis[2-(phenyloxymethyl)-2-(hydroxy)ethylthio]diphenylsulfide (27.6 g; 50 mmoles) and triethylamine (13.5 g; 134 mmoles) in CH2CI2 (100 ml) at 0-5C. The mixture is stirred at room temperature for 3h. After addition of water (50 ml), the crude is extracted with CH2CI2, washed with aqueous 5% NaOH solution, passed over a short silica gel plug and stripped of solvent to give 4,4'-bis[2-(phenyloxymethyl)-2-(methacryloyloxy)ethylthio]diphenylsulfide as a clear, slight- yellow liquid (29.3 g; yield 85%; nD251.621 ). 1H NMR (CDCI3, delta ppm) 7.20 (m, 12H), 6.90 (t, 2H), 6.80 (d, 4H), 6.00 (s, 2H), 5.48 (s, 2H), 5.22 (quintet, 2H), 4.21 (t, 2H), 3.39 (dd, 2H), 1.83 (s, 6H), 1.51 (s, 4H).
  • 54
  • [ 30674-80-7 ]
  • [ 19362-77-7 ]
  • [ 1048373-38-1 ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine; In toluene; at 20℃; Example 64,4'-Bis(methacryloyloxyethylcarbamoylthio)diphenylsulfideA mixture of 4,4'-(thiophenyl)sulfide (12.5 g; 0.05 moles), 2-isocyanato methacrylate (34.1 g; 0.22 moles), and triethylamine (0.9 g) in toluene (150 ml) is stirred at room temperature with instantaneous formation of a voluminous white solid product. The reaction mixture is filtered and the mother liquors are placed in the refrigerator when additional solid crystallized. The combined solids afforded the desired product as a pure, white solid (25.2 g; yield 90%). 1H NMR (CDCI3, delta ppm) 7.49 (d, 4H), 7.36 (d, 4H), 6.09 (d, 2H), 5.70 (t, 2H), 5.62 (d, 4H), 4.25 (t, 4H), 3.60 (q, 4H), 1.94 (s, 6H).
87.5% In acetone; at 20℃; for 5.5h; A mixture solution of IEM (10.41 g, 67.07 mmol) and 20 mL anhydrous acetone was added dropwise to an anhydrous acetone solution (150 mL) of PBDT (8.00 g, 31.94 mmol), for 30 min at RT. The reaction proceeded for 5 h to react the ingredients completely. Subsequently, the reaction mixture was concentrated by rotary evaporation, and the crude product was further purified by column chromatography using 1:3 acetone/petroleum as eluent to give a white powder (15.67 g, 87.5%).
  • 55
  • [ 19362-77-7 ]
  • [ 753-73-1 ]
  • [ 1008533-57-0 ]
  • 56
  • [ 19362-77-7 ]
  • [ 1066-45-1 ]
  • [ 1008533-54-7 ]
  • 57
  • [ 19362-77-7 ]
  • [ 3151-41-5 ]
  • [ 1008533-56-9 ]
  • 58
  • [ 19362-77-7 ]
  • [ 1135-99-5 ]
  • [ 1008533-58-1 ]
  • 59
  • [ 19362-77-7 ]
  • [ 639-58-7 ]
  • [ 1008533-55-8 ]
  • 60
  • [ 19362-77-7 ]
  • [ 3002-01-5 ]
  • [ 1008533-59-2 ]
  • 61
  • [ 19362-77-7 ]
  • [ 1168723-23-6 ]
  • [ 1168723-25-8 ]
  • 62
  • [ 19362-77-7 ]
  • [ 76435-22-8 ]
  • [ 1210440-82-6 ]
  • 63
  • [ 19362-77-7 ]
  • [ 5367-28-2 ]
  • [ 1210440-78-0 ]
  • 64
  • [ 117-80-6 ]
  • [ 64-17-5 ]
  • [ 19362-77-7 ]
  • [ 1259956-07-4 ]
  • [ 1259956-06-3 ]
  • 66
  • [ 19362-77-7 ]
  • [ 1357516-23-4 ]
  • [ 1357516-25-6 ]
  • 67
  • [ 19362-77-7 ]
  • [ 1357351-42-8 ]
  • [ 1357516-26-7 ]
  • 68
  • [ 19362-77-7 ]
  • [ 22711-24-6 ]
  • [ 1242241-52-6 ]
  • 69
  • [ 19362-77-7 ]
  • [ 871132-46-6 ]
  • [ 1241386-11-7 ]
  • 70
  • [ 19362-77-7 ]
  • [ 888031-81-0 ]
  • [ 1241386-13-9 ]
  • 71
  • [ 19362-77-7 ]
  • [ 1035221-48-7 ]
  • [ 1379468-81-1 ]
  • 72
  • [ 61351-34-6 ]
  • [ 19362-77-7 ]
  • 1-[(1,3,4,4-tetrachloro-2-nitrobuta-1,3-dien-1-yl)sulfanyl]-4-([4-[(1,3,4,4-tetrachloro-2-nitrobuta-1,3-dien-1-yl)sulfanyl]phenyl]sulfanyl)benzene [ No CAS ]
  • 73
  • [ 19362-77-7 ]
  • [ 121-44-8 ]
  • C12H10S3*2C6H15N [ No CAS ]
  • 74
  • [ 446-36-6 ]
  • [ 19362-77-7 ]
  • [ 1467066-71-2 ]
  • 75
  • [ 14243-64-2 ]
  • [ 75-09-2 ]
  • [ 19362-77-7 ]
  • C48H38Au2P2S3*0.5CH2Cl2 [ No CAS ]
  • 76
  • [ 38255-48-0 ]
  • [ 19362-77-7 ]
  • C46H36Au2N2P2S3 [ No CAS ]
  • 77
  • [ 19362-77-7 ]
  • [ 13239-25-3 ]
  • [ 1600504-86-6 ]
  • 78
  • [ 19362-77-7 ]
  • [ 88-95-9 ]
  • [ 250294-28-1 ]
  • 79
  • [ 634-47-9 ]
  • [ 19362-77-7 ]
  • [ 1608504-48-8 ]
  • 80
  • [ 3913-17-5 ]
  • [ 19362-77-7 ]
  • [ 1608504-50-2 ]
  • 81
  • [ 3913-18-6 ]
  • [ 19362-77-7 ]
  • [ 1608504-49-9 ]
  • 82
  • [ 4298-52-6 ]
  • [ 19362-77-7 ]
  • C24H18S5 [ No CAS ]
  • [ 1607804-39-6 ]
  • 83
  • [ 19362-77-7 ]
  • [ 104-88-1 ]
  • [ 109-77-3 ]
  • 6,6'-(4,4'-thiobis(4,1-phenylene)bis(sulfanediyl))bis(2-amino-4-(4-chlorophenyl)pyridine-3,5-dicarbonitrile) [ No CAS ]
  • 84
  • [ 19362-77-7 ]
  • [ 108-88-3 ]
  • [ 103677-18-5 ]
  • 85
  • [ 19362-77-7 ]
  • [ 106131-61-7 ]
  • C28H16N8S6 [ No CAS ]
  • C42H24N12S9 [ No CAS ]
  • 86
  • [ 19362-77-7 ]
  • [ 1488422-74-7 ]
  • bis[4-(1,2,5,6,7-pentamethyl-4,4-difluoro-4-bora-3a,4a-diaza-sindacen-3-ylthio)phenyl]sulfide [ No CAS ]
  • 87
  • [ 19362-77-7 ]
  • C43H33NO2 [ No CAS ]
  • C98H76N2O4S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine; In tetrahydrofuran; at 20℃; To the mixture of 2 (2.30 g, 0.004 mol) and 4,4'-thiobisbenzenethiol (0.50 g, 0.002 mol) in THF (20 mL) triethylamine (0.4 mL, 0.001 mol) were added and the obtained mixture was stirred at room temperature overnight. After termination of the reaction (TLC monitoring) THF and trimethylamine were removed and the residue was purified by column chromatography using acetone: n-hexane (1:4,v/v) as the eluent. A 20% solution of the resulting product in toluene was prepared and poured with intensive stirring into a 10-fold excess of n-hexane. The precipitate was filtered off and washed with n-hexane. The yield of compound 3 was 2.37 g (82%). 1H-NMR (CDCl3, ppm): delta 7.48-6.86 (m, 64H, Ht, Ph, C=CH, NH); 4.21 (d, J = 4.7 Hz, 4H, OCH2CH); 4.07-3.98 (m, 2H, CHO); 3.12 (dd, J1 = 13.8 Hz, J2 = 6.1 Hz, 2H, one proton of SCH2); 3.04 (dd, J1 = 13.8 Hz, J2 = 6.8 Hz, 2H, other proton of SCH2); 2.61 (d, J = 4.9 Hz, 2H, OH). IR (KBr, cm-1): 3549 (OH); 3423 (NH); 3053, 3021 (aromatic CH); 2921, 2867 (aliphatic CH); 1598, 1576, 1491, 1475, 1443 (C=C, C-N); 1208, 1167, 1098, 1073,1029, 1010 (C-O-C); 811, 765, 744, 698 (CH=CH of 1,2,3,-trisubstituted carbazole, monosubstituted and 1,4-disubstituted benzene); 641, 611 (C-S). Anal. Calcd for C98H76N2O4S3: C, 80.09; H, 5.33; N,1.90. Found: C, 79.83; H, 5.31; N, 1.74.
  • 88
  • [ 139-66-2 ]
  • [ 19362-77-7 ]
  • 89
  • C14H18N4S3 [ No CAS ]
  • [ 19362-77-7 ]
YieldReaction ConditionsOperation in experiment
80% With water; sodium hydroxide; In ethanol; at 80 - 90℃; for 2h; To 10 l of the reaction flask was added the product obtained in Example 2 (338g, 1mol) embodiment, water (3 liters) and ethanol (2 l), then heated to 80-90 deg.] C, at this temperature, under stirring drop state added aqueous sodium hydroxide (100g, 2.5mol) 3 liters, dropwise over 2 hours to complete.Then at this temperature, stirring was continued for 6-8 hours.After completion of the reaction, cooled to room temperature and extracted with dichloromethane (3 * 2 liters) and the combined organic phase was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, and dichloromethane was distilled off under reduced pressure, after recrystallization to give the product (200g, 80% yield)
  • 90
  • [ 19362-77-7 ]
  • 1-bromomethyl-3,5,7-trimethyl-2,4,6,8,9,10-hexathiaadamantane [ No CAS ]
  • C28H30S15 [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 7h;Inert atmosphere; In a 100 ml three-necked flask, 1.66 g (12 mmol) of potassium carbonate,1.0 g (4.0 mmol) of 4,4'-thiobisbenzenethiol was charged, and nitrogen was introduced to form a nitrogen atmosphere. 25 ml of N, N-dimethylformamide as a solvent was added and stirred to obtain 3.79 g of 1-bromomethyl-3,5,7-trimethyl-2,4,6,8,8,9,10-hexathiaadamantane (10 Mmol) was added as a solid. The mixture was heated in an oil bath at 90 C. and allowed to react for 7 hours, and then it was confirmed by TLC that the raw material had disappeared.The reaction mixture was poured into 200 ml of water and diluted and extracted three times with ethyl acetate. The combined organic layer was washed twice with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Five parts of the obtained crude product was purified by silica gel column chromatography (eluent: hexane: ethyl acetate = 6: 1), and the fractions of the main constituents were collected and the solvent was removed to obtain a white solid (yield: 0. 89 g, yield: 26%
  • 91
  • [ 19362-77-7 ]
  • [ 25069-74-3 ]
  • di(4-(2-(4-(N,N-diphenylamino)phenyl)ethyl)thio)phenylsulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% In dichloromethane; at 20℃; for 1h;Inert atmosphere; General procedure: A mixture of vinyl derivative (V-TPA or V-CZ, 2.2 equiv.) and 4,4'-thiodibenzenthiol (TBT, 1.0 equiv.) in dichloromethane was stirred for 1 h under argon atmosphere at room temperature. Then the solvent was distilled and the crude product was purified by column chromatography. Di(4-(2-(4-(N,N-diphenylamino)phenyl)ethyl)thio)phenylsulfide (TBT-2TPA) was prepared according to the general procedure from 4-vinyltriphenylamine (V-TPA, 1.6 g, 5.9 mmol) and 4,40-thiodibenzenthiol (TBT, 0.5 g, 2.0 mmol). The crude product was purified by column chromatography on silica gel using hexane/dichloromethane (8/1) as an eluent. The target compound was obtained as white powder (fw = 792 g/mol) in 38% yield (0.37 g). 1H NMR (700 MHz, CDCl3), delta (ppm): 2.91 (t, J = 8.3 Hz, 4H, S-CH2), 3.17(t, J = 8.3 Hz, 4H, Ar-CH2), 7.00-7.06 (m, 8H, Ar), 7.07-7.11 (m, 12H,Ar), 7.22-7.30 (m, 16H, Ar). 13C NMR (175 MHz, CDCl3), delta (ppm):147.9, 146.3, 136.0, 134.4, 133.1, 131.5, 129.6, 129.3, 129.2, 124.4,124.0, 122.6, 35.1 (S-CH2), 35.0 (Ar-CH2). MS (APCl+, 20 V), m/z(%) = 793 ([M + H]+, 100). Elemental analysis. Calcd for C52H44N2S3(%): C 78.75, H 5.59, N 3.53, S 12.13; found (%): C 78.63, H 5.69, N3.64.
  • 92
  • [ 1486-07-3 ]
  • [ 19362-77-7 ]
  • C44H40N2S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% In dichloromethane; at 20℃; for 1h;Inert atmosphere; General procedure: A mixture of vinyl derivative (V-TPA or V-CZ, 2.2 equiv.) and 4,4'-thiodibenzenthiol (TBT, 1.0 equiv.) in dichloromethane was stirred for 1 h under argon atmosphere at room temperature. Then the solvent was distilled and the crude product was purified by column chromatography.
  • 93
  • [ 19362-77-7 ]
  • C42H36N12O12S6 [ No CAS ]
  • C26H26N4O8S4 [ No CAS ]
  • C28H20N8O4S5 [ No CAS ]
  • 94
  • [ 19362-77-7 ]
  • C42H36N12O12S6 [ No CAS ]
  • C28H20N8O4S5 [ No CAS ]
  • 95
  • [ 19362-77-7 ]
  • [ 25906-72-3 ]
  • [ 106131-61-7 ]
  • C28H20N8O4S5 [ No CAS ]
  • 96
  • [ 19362-77-7 ]
  • C24H12N12S6 [ No CAS ]
  • C22H12N8S5 [ No CAS ]
  • 97
  • [ 19362-77-7 ]
  • 1,4-bis((6-chloro-1,2,4,5-tetrazin-3-yl)thio)benzene [ No CAS ]
  • C22H12N8S5 [ No CAS ]
  • 98
  • 4,4'-bis(acetylthio)diphenyl sulfide [ No CAS ]
  • [ 19362-77-7 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydroxide; In water; for 3h;Reflux; Large scale; In a 500 L reactor,Take 15kg sodium hydroxide dissolved in 200L of water,25kg of 4,4'-bis (acetylthio) diphenyl sulfide (II)Stir for 3 hours,Make the solid fully dissolved,Hot filtration,Insoluble matter was removed, the filtrate was cooled to room temperature,Slowly add 30% hydrochloric acid mass concentration to make the pH of 3.Stirring crystallization 3 hours, suction filtration,The crude product of 4,4'-dimercaptodiphenyl sulfide (III) was obtained in an amount of 18.5 kg.Recrystallization with 200 kg of toluene,18 kg of yellowish flaky crystal 4,4'-dimercaptodiphenyl sulfide (III), yield 96.3%, HPLC 99.25%.In a 500 L reactor,15kg of crude 4,4'-dimercaptodiphenyl sulfide (III)100kg toluene, 60kg water,1kg zinc powder,Slow heating while warming slowly dropping 15% hydrochloric acid mass concentration of 100kg,After the addition temperature was raised to 80 or so. At this point the solution becomes colorless clear night, rapid filtration,Hot liquid, the upper crystallization of toluene,14.4kg white flaky crystals of 4,4'-dimercaptodiphenyl sulfide (IV) boutique.HPLC 99.68%, yield 96%. The total yield of 83%.
  • 99
  • [ 19362-77-7 ]
  • C18H11Cl2N9O3 [ No CAS ]
  • C30H19N9O3S3 [ No CAS ]
  • 100
  • [ 17685-52-8 ]
  • [ 19362-77-7 ]
  • [Fe2(CO)6]2(μ-4,4'-thiobisbenzenethiolato)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
41.3% In toluene; for 0.5h;Inert atmosphere; Reflux; Triirondodecarbonyl (2.28 g, 4.53 mmol) and 4,40-thiobisbenzenethiol(0.85 g, 3.39 mmol) were mixed in a 100 mL flask andpurged with nitrogen for 30 min. Toluene (70 mL) was then addedto the flask and stirred under reflux conditions for 30 min. Thesolution changed color from dark green to red. The solvent of thesolution was removed by rotary evaporation affording an orangesolid. Silica gel chromatographic separation of the residue usinghexanes-dichloromethane (50:50) solvent mixture as eluent gave[Fe2(CO)6]2(m-4,40-thiobisbenzenethiolato)2 as an orange productin 41.3% yield
  • 101
  • C10H12N5O7PS [ No CAS ]
  • [ 3344-70-5 ]
  • [ 19362-77-7 ]
  • guanosine-3',5'-cyclic monophosphate-[8-thio-(dodecanyl)-(4-thio-phenyl-4''-thio-phenylthio)-(dodecanyl)-thio-8]-guanosine-3',5'-cyclic monophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% General procedure: A solution of 8-T-cGMP (200 mM, 1 eq) and N.N-diisopropylethylamine (2 eq) in DMSO was added portionwise over 30 min to a solution of 1 , 12-dibromdodecane (1.5 M, 15 eq) in (0803) DMSO at 40 C. The reaction mixture was stirred until no further reaction progress was observed (< 10 % remaining starting material). The solvent was removed through high vacuum evaporation with a speedvac concentrator. The residue was dissolved in (0804) MeCN/water (8:1 , v/v), washed with petroleum ether (3 x) and the aqueous phase evaporated to dryness using a rotary evaporator. The crude product was dissolved in DMF (115 mM). 4,4"-Thiobisbenzenthiol (0.5 eq) and Nu,Nu-diisopropylethylamine (2.2 eq) were added successively. The reaction mixture was stirred until the starting material was completely consumed. The solvent was removed through high vacuum evaporation with a speedvac concentrator. The residue was dissolved in water (1 mL), washed with ethyl acetate (3 x 1 mL), subjected to preparative reversed phase hplc and desalted. (0805) Yield f Purity) :26 % (> 99 %). (0806) HPLC: (57 % MeCN, 30 mM NaH2PO* buffer, pH 6.8). (0807) UV-VIS: Amax = 275 nm (pH 7), epsilon = 24660 (est.). (0808) ESI- S (+): m/z calculated for C56H73N10O14P2S5 (P+H]+): 1337.39, found: 1337. (0809) ESS-MS (-): m/z calculated for C56H77N10O14P2S5 ([M-H] ): 1335.37, found: 1335.
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