Home Cart 0 Sign in  
X

[ CAS No. 1015-38-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 1015-38-9
Chemical Structure| 1015-38-9
Chemical Structure| 1015-38-9
Structure of 1015-38-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1015-38-9 ]

Related Doc. of [ 1015-38-9 ]

Alternatived Products of [ 1015-38-9 ]

Product Details of [ 1015-38-9 ]

CAS No. :1015-38-9 MDL No. :MFCD00014457
Formula : C12H11PS2 Boiling Point : -
Linear Structure Formula :- InChI Key :CLUOCCWZZAGLPM-UHFFFAOYSA-N
M.W : 250.32 Pubchem ID :129564
Synonyms :

Calculated chemistry of [ 1015-38-9 ]

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 : 75.65
TPSA : 80.7 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) : -4.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 4.7
Log Po/w (WLOGP) : 3.61
Log Po/w (MLOGP) : 3.8
Log Po/w (SILICOS-IT) : 5.01
Consensus Log Po/w : 3.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.81
Solubility : 0.00385 mg/ml ; 0.0000154 mol/l
Class : Moderately soluble
Log S (Ali) : -6.12
Solubility : 0.000189 mg/ml ; 0.000000753 mol/l
Class : Poorly 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 : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.84

Safety of [ 1015-38-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1015-38-9 ]

* 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 [ 1015-38-9 ]

[ 1015-38-9 ] Synthesis Path-Downstream   1~53

  • 2
  • [ 1015-38-9 ]
  • [ 1017-89-6 ]
YieldReaction ConditionsOperation in experiment
93% With 50-100 mmol; chlorine In tetrachloromethane 1) 0 deg C, 2) 30 min, r.t.;
With chlorine
  • 5
  • [ 1015-38-9 ]
  • [ 6079-77-2 ]
YieldReaction ConditionsOperation in experiment
99.7% With dihydrogen peroxide In tert-butyl methyl ether; water at 2 - 5℃; for 0.25h; Inert atmosphere;
40% With tetrachloromethane; sodium ethanolate In N,N-dimethyl-formamide at 60℃; for 6h;
  • 6
  • [ 1015-38-9 ]
  • [ 2315-36-8 ]
  • [ 71037-00-8 ]
YieldReaction ConditionsOperation in experiment
62% With potassium hydroxide In benzene at 20℃; for 3h;
  • 7
  • [ 1015-38-9 ]
  • [ 98-88-4 ]
  • [ 22551-30-0 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In benzene for 0.25h; ice-cooling;
  • 8
  • [ 286-20-4 ]
  • [ 1015-38-9 ]
  • Diphenyl-phosphinodithioic acid (1R,2R)-2-hydroxy-cyclohexyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In toluene at 0℃; for 0.5h;
  • 9
  • (1S,5R)-6-Oxa-bicyclo[3.1.0]hexane [ No CAS ]
  • [ 1015-38-9 ]
  • Diphenyl-phosphinodithioic acid (1R,2R)-2-hydroxy-cyclopentyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% In toluene at 0℃; for 0.5h;
  • 10
  • [ 1015-38-9 ]
  • [ 4925-71-7 ]
  • Diphenyl-phosphinodithioic acid (1R,2R)-2-hydroxy-cyclooctyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% In toluene at 0℃; for 0.5h;
  • 11
  • [ 1015-38-9 ]
  • [ 14149-40-7 ]
  • [ 92589-06-5 ]
  • [ 6079-78-3 ]
YieldReaction ConditionsOperation in experiment
93% With diphenyldithiophosphonic acid In isopropyl alcohol at 58℃; for 38h;
  • 12
  • [ 4549-74-0 ]
  • [ 1015-38-9 ]
  • diphenylphosphinodithioic acid 1,2-dimethylbut-2-enyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With silver tetrafluoroborate In dichloromethane at 20℃;
  • 13
  • [ 577-71-9 ]
  • [ 1015-38-9 ]
  • O-(3,4-dinitrophenyl) diphenylphosphinothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: diphenylphosphinodithioic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane for 3h; Stage #2: 3,4-dinitophenol In dichloromethane at 20℃; Further stages.;
With dmap; dicyclohexyl-carbodiimide In dichloromethane
  • 14
  • [ 1015-38-9 ]
  • [ 18298-00-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: chlorine / beim anschliessenden Erhitzen mit rotem Phosphor
  • 15
  • [ 1005500-82-2 ]
  • [ 1015-38-9 ]
  • [ 1005500-92-4 ]
YieldReaction ConditionsOperation in experiment
97% In 1,2-dimethoxyethane at 20℃; for 1h;
  • 16
  • [ 1005500-75-3 ]
  • [ 1015-38-9 ]
  • [ 1005500-83-3 ]
YieldReaction ConditionsOperation in experiment
86% In 1,2-dimethoxyethane at 20℃; for 1h;
86% In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 17
  • [ 1005500-76-4 ]
  • [ 1015-38-9 ]
  • [ 1005500-84-4 ]
YieldReaction ConditionsOperation in experiment
76% In 1,2-dimethoxyethane at 20℃; for 1h;
76% In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 18
  • [ 1005500-78-6 ]
  • [ 1015-38-9 ]
  • [ 1005500-86-6 ]
YieldReaction ConditionsOperation in experiment
91% In 1,2-dimethoxyethane at 20℃; for 1h;
91% In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 19
  • [ 1005500-79-7 ]
  • [ 1015-38-9 ]
  • [ 1005500-87-7 ]
YieldReaction ConditionsOperation in experiment
97% In 1,2-dimethoxyethane at 20℃; for 1h;
97% In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 20
  • [ 1005500-80-0 ]
  • [ 1015-38-9 ]
  • [ 1005500-88-8 ]
YieldReaction ConditionsOperation in experiment
88% In 1,2-dimethoxyethane at 20℃; for 1h;
88% In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 21
  • [ 1005500-81-1 ]
  • [ 1015-38-9 ]
  • [ 1005500-89-9 ]
YieldReaction ConditionsOperation in experiment
97% In 1,2-dimethoxyethane at 20℃; for 1h;
97% In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 22
  • [ 872349-00-3 ]
  • [ 1015-38-9 ]
  • [ 1005500-90-2 ]
YieldReaction ConditionsOperation in experiment
63% In 1,2-dimethoxyethane at 20℃; for 1h;
63% In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 23
  • [ 1015-38-9 ]
  • [ 683246-91-5 ]
  • [ 1005500-91-3 ]
YieldReaction ConditionsOperation in experiment
95% In 1,2-dimethoxyethane at 20℃; for 1h;
95% In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction;
  • 24
  • [ 1015-38-9 ]
  • [ 14364-93-3 ]
  • {Pt(CH3)3(C5H5N)(SSP(C6H5)2)} [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With pyridine In benzene byproducts: C5H5N*HI; excess of pyridine, stirring, 30 min; addn. of (C6H5)2PSSH; stirring, 1 h; filtn.; drying (vac.); recrystn. (benzene/hexane); elem. anal.;
  • 25
  • [ 1034014-59-9 ]
  • [ 1015-38-9 ]
  • [ 1034014-66-8 ]
YieldReaction ConditionsOperation in experiment
96% In ethanol at 25℃; for 5h; Inert atmosphere; optical yield given as %de; stereoselective reaction;
  • 26
  • [ 1034014-60-2 ]
  • [ 1015-38-9 ]
  • (E)-1-dodecylsulfanyl-1-octenyl diphenyldithiophosphinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In ethanol at 25℃; for 5h; Inert atmosphere; stereoselective reaction;
  • 27
  • [ 1034014-61-3 ]
  • [ 1015-38-9 ]
  • [ 1034014-70-4 ]
YieldReaction ConditionsOperation in experiment
91% In ethanol at 25℃; for 5h; Inert atmosphere; optical yield given as %de; stereoselective reaction;
  • 28
  • [ 1034014-63-5 ]
  • [ 1015-38-9 ]
  • [ 1034014-72-6 ]
YieldReaction ConditionsOperation in experiment
86% In ethanol at 25℃; for 5h; Inert atmosphere; optical yield given as %de; stereoselective reaction;
  • 29
  • [ 1034014-64-6 ]
  • [ 1015-38-9 ]
  • [ 1034014-73-7 ]
YieldReaction ConditionsOperation in experiment
92% In ethanol at 25℃; for 5h; Inert atmosphere; stereoselective reaction;
  • 30
  • [ 1034014-65-7 ]
  • [ 1015-38-9 ]
  • [ 1034014-74-8 ]
YieldReaction ConditionsOperation in experiment
97% In ethanol at 25℃; for 5h; Inert atmosphere; optical yield given as %de; stereoselective reaction;
  • 31
  • [ 63707-12-0 ]
  • [ 1015-38-9 ]
  • [ 1034014-67-9 ]
YieldReaction ConditionsOperation in experiment
85% In ethanol at 25℃; for 5h; Inert atmosphere; stereoselective reaction;
  • 32
  • [ 1015-38-9 ]
  • [ 433228-70-7 ]
  • [ 1034014-69-1 ]
YieldReaction ConditionsOperation in experiment
86% In ethanol at 25℃; for 5h; Inert atmosphere; optical yield given as %de; stereoselective reaction;
  • 33
  • [ 915281-92-4 ]
  • [ 1015-38-9 ]
  • [ 1187947-92-7 ]
YieldReaction ConditionsOperation in experiment
84% In toluene at 100℃; for 1h; regioselective reaction;
  • 34
  • [ 915281-93-5 ]
  • [ 1015-38-9 ]
  • [ 1187948-00-0 ]
YieldReaction ConditionsOperation in experiment
83% In toluene at 100℃; for 1h; regioselective reaction;
  • 35
  • [ 1064087-13-3 ]
  • [ 1015-38-9 ]
  • [ 1187948-08-8 ]
YieldReaction ConditionsOperation in experiment
72% In toluene at 100℃; for 1h; regioselective reaction;
  • 36
  • [ 1093645-87-4 ]
  • [ 1015-38-9 ]
  • [ 1187948-03-3 ]
YieldReaction ConditionsOperation in experiment
82% In toluene at 100℃; for 1h; regioselective reaction;
  • 37
  • [ 32749-90-9 ]
  • [ 1015-38-9 ]
  • [ 1187948-17-9 ]
YieldReaction ConditionsOperation in experiment
90% With water-d2 In toluene at 100℃; for 1h; regioselective reaction;
  • 38
  • [ 32749-90-9 ]
  • [ 1015-38-9 ]
  • [ 1187946-93-5 ]
YieldReaction ConditionsOperation in experiment
95% With 2,6-di-tert-butyl-4-methylpyridine In toluene at 100℃; for 1h; regioselective reaction;
  • 39
  • [ 1015-38-9 ]
  • [ 153619-99-9 ]
  • [ 1187947-85-8 ]
YieldReaction ConditionsOperation in experiment
99% In toluene at 100℃; for 1h; regioselective reaction;
  • 40
  • [ 1015-38-9 ]
  • [ 331676-35-8 ]
  • [ 1187947-81-4 ]
YieldReaction ConditionsOperation in experiment
90% In toluene at 100℃; for 1h; regioselective reaction;
  • 41
  • [ 1015-38-9 ]
  • [ 331676-33-6 ]
  • [ 1187947-89-2 ]
YieldReaction ConditionsOperation in experiment
79% In toluene at 100℃; for 1h; regioselective reaction;
  • 42
  • [ 1015-38-9 ]
  • [ 1572-99-2 ]
  • [ 17503-31-0 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol at 20℃; Reflux; 79 Intermediate 79: Ethyl 3-amino-2-methyl-3-thioxopropanoate A mixture of diphenylphosphinodithioic acid (Alfa-Aesar) (7.48 g, 29.9 mmol) and 2-cyanopropionic acid ethyl ester (ABCR, 1.980 mL, 14.94 mmol) in isopropanol (80 mL) was heated under reflux for 8 h then stood at rt overnight. Reaction mixture was filtered and filtrate was diluted with EtOAc and washed with 1N NaOH, brine, and dried over Na2SO4. Crude was purified by chromatography on silica gel using a Hex/EtOAc gradient. Appropriate fractions were combined and evaporated to yield title compound as a yellow oily solid. 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.60 (s, 1H), 9.40 (s, 1H), 4.05 (q, 2H), 3.74 (q, 1H), 1.29 (d, 3H), 1.15 (t, 3H). [ES+MS] m/z 162 (MH+).
  • 43
  • [ 1572-98-1 ]
  • [ 1015-38-9 ]
  • [ 17969-52-7 ]
YieldReaction ConditionsOperation in experiment
46.32% In isopropyl alcohol for 4h; Reflux; 91 Intermediate 91: ethyl 3-amino-2,2-dimethyl-3-thioxopropanoate A mixture of diphenyldithiophosphonic acid (ALFAAESAR, 1.42 g, 5.67 mmol) and 2-cyano-2-methylpropionic acid ethyl ester (ABCR, 0.412 mL, 2.83 mmol) in isopropanol (30 mL) was heated under reflux for 4 h. Reaction mixture was cooled to room temperature and a precipitate was formed. Reaction flask was placed in the freezer for 1 h. Reaction mixture was filtered and filtrate was concentrated. Residue was taken up in DCM (100 mL) and washed with water (20 mL), 1N NaOH (20 mL), saturated NaHCO3 (20 mL) and dried over sodium sulfate and concentrated. The resulting oil was loaded on a 25 g silica cartridge and eluted with linear gradient 0-50% hexane-ethyl acetate to yield the title compound (110 mg, 0.628 mmol, 22.2% yield). Another impure batch was loaded on a 10 g silica cartridge and eluted with linear gradient 0-50% hexane-ethyl acetate to recover the title compound (120 mg, 0.685 mmol, 24.17% yield). Total yield: (230 mg, 1.313 mmol, 46.32%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.70 (br s, 1H), 8.86 (br s, 1H), 4.05 (q, 2H), 1.39 (s, 6H), 1.15 (t, 3H). [ES+MS] m/z 176 (MH+).
  • 44
  • [ 1015-37-8 ]
  • [ 5827-17-8 ]
  • [ 1015-38-9 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: diphenylthiophosphinoyl chloride With sodium hydrogensulfide In water at 95℃; for 2h; Stage #2: sodium diphenylphosphinodithioate With hydrogenchloride In water at 20℃; for 0.5h;
  • 45
  • [ 13755-29-8 ]
  • di-μ-sulphido-tetrakis(triphenylphosphine)-diplatinum(II) [ No CAS ]
  • [ 1015-38-9 ]
  • [ 5970-45-6 ]
  • [Pt2(μ-S)2(PPh3)4Zn(S2PPh2)]BF4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% Stage #1: di-μ-sulphido-tetrakis(triphenylphosphine)-diplatinum(II); zinc(II) acetate dihydrate In methanol for 0.25h; Stage #2: diphenylphosphinodithioic acid With trimethylamine In methanol; water for 1h; Stage #3: sodium tetrafluoroborate In methanol; water 3.2. Synthesis of [Pt2(μ-S)2(PPh3)4ZnQ]BF4 (7*BF4) General procedure: A suspension of [Pt2(μ-S)2(PPh3)4] (363 mg, 0.242 mmol) and Zn(OAc)2*2H2O (55 mg,0.251 mmol) in methanol (40 mL) was stirred for 15 min. to give a cream solution/suspension. 8-Hydroxyquinoline (HQ, 37 mg, 0.255 mmol) was added and the reaction mixture immediately went more yellow. Aqueous trimethylamine solution (five drops, excess) was added with no significant change. The reaction mixture was stirred for 1 h and filtered through glass fiber filter paper to give a clear yellow solution. Sodium tetrafluoroborate (200 mg, large excess) was added, followed by water (60 mL) to give a yellow precipitate. This was filtered, washed with water (2 × 10 mL), and dried under vacuum to give 7*BF4 (194 mg, 45%) as a pale yellow solid.
  • 46
  • [ 866-54-6 ]
  • [ 1015-38-9 ]
  • [ 56990-50-2 ]
  • [ 24057-20-3 ]
  • [ 6079-77-2 ]
  • N-tert-butyl-2-(diphenylphosphinothioylthio)-2-methylpropan-1-iminium chloride [ No CAS ]
  • C12H26NPS2*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 20℃; for 3h; Competitive reaction of acids 7a and 7b with imine 8a. A solution of a mixture of 0.93 g (3.7 mmol) of acid 7 and 0.57 g (3.7 mmol) of acid 7b was added dropwise at 0-5° to a solution of 0.6 g (3.7 mmol) chlorimine 8 in CH2Cl2. The reaction mixture was then let to warm up to 20°C and was stirred for 3 h. The 31P NMR spectrum of the reaction mixture showed signals of compounds 10 (57.3 ppm), 12 (68.12 ppm), 10c (77.21 ppm), and 12b (89.25 ppm), as well signals of the starting dithio acids 7 (56.55 ppm) and 7b (75.46 ppm). From the integral intensities of the signals it was concluded that, firstly, in the reaction with chlorimine 8 78% of acid 7 was consumed and as little as 37% of acid 7b, and secondly, the reaction of diphenylphosphinothioic acid 7 with imine 8 resulted predominantly in the formation of substitution product 10, and of diethylphosphinothioic acid 7b, in the formation of substituted product 10c and of reduction product 12b in a ratio 55 : 45.
  • 47
  • [ 1015-38-9 ]
  • [ 56990-50-2 ]
  • 1,1-dimethyl-2-oxoethyl diphenylphosphinodithioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% Stage #1: diphenylphosphinodithioic acid; N-(2-chloro-2-methylpropylidene)-tert-butylamine In dichloromethane at 0 - 20℃; for 48h; Inert atmosphere; Stage #2: With hydrogenchloride; water In dichloromethane at 10 - 20℃; for 1h; 1,1-Dimethyl-2-oxoethyl diphenylphosphinodithioate (15a). General procedure: Acid 7a, 15 g (0.06 mol), was added in portions under argon to a solution of 11.6 g (0.071 mol) of imine 8 in 75 mL of anhydrous methylene chloride maintaining the temperature of the reaction mixture at 0-5°. The mixture was stirred at room temperature for 5 h. After 48 h, to convert iminium salt 10a in toa ldehyde 15a, water, 16 mL (0.089 mol), containing 2-3 drops of conc. HCl was added maintaining the temperature of the reaction mixture at 10-15°. The mixture was stirred at room temperature for 1 h. The organic layer was separated and dried with MgSO4. The solvent was removed and the residue was recrystallized from CCl4. Yield 10.2 g (54%).
  • 48
  • [ 1015-38-9 ]
  • [ 56990-50-2 ]
  • N-tert-butyl-2-(diphenylphosphinothioylthio)-2-methylpropan-1-iminium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% In tetrachloromethane at 0 - 20℃; for 54h; Inert atmosphere; N-tert-Butyl-2-(diphenylphosphinothioylthio)-2-methylpropan-1-iminium chloride (10a) General procedure: Acid 7, 10.53 g (0.042 mol), was added in portions with stirring under dry argon to a solution of 8.17 g (0.05 mol) of imine 8a in 60 mL CCl4, maintaining the temperature at 0-3°. The reaction mixture was then let to warm up to 20°, stirred for 6 h, and allowed to stand at a room temperature for 48 h. The solvent and excess chlorimine were removed in a vacuum, the residue was treated with diethyl ether and cooled down. The crystals were filtered off. Yield 15.8 g (91%).
91% In tetrachloromethane at 0 - 20℃; Inert atmosphere; Reaction of diphenyldithiophosphinic acid (17) with N-tert-butyl-2-chloro-2-methylpropanimine (9a) General procedure: To a stirred solution of imine 9a (8.17 g, 50 mmol) in CCl4 (60 mL), acid 17 (10.53 g, 42 mmol) was added by portions under an argon flow maintaining the reaction temperature at 0-3 °C. Then the reaction temperature was raised to 20 °C and stirring was continued for additional 6 h. The reaction mixture was kept at room temperature for 48 h and the volatiles (solvent and chlorimine excess) were removed in vacuo. The residue was treated with diethyl ether and cooled down, the crystals formed were collected by filtration to give iminium salt 20a in the yield of 15.8 g (91%), m.p. 124 °C. 1H NMR (CDCl3), δ: 1.62 (s, 9 H, CMe3); 1.86 (s, 6 H, CMe2); 7.90 (dd, 4 H, ortho-CH(arom), 3JHH = 7.0 Hz, 3JPH = 14.4 Hz); 7.36-7.54 (m, 6 H, meta- and para-CH(arom)); 8.87 (s, 1 H, CH=N+); 14.81 (br.s, 1 H, N+H). 31P NMR (CDCl3), δ: 57.63. Found (%): C, 58.48; H, 6.71; P, 7.43; S, 15.10. C20H27ClNPS2. Calculated (%): C, 58.31; H, 6.61; P, 7.52; S, 15.57
  • 49
  • [ 1015-38-9 ]
  • [ 63364-30-7 ]
  • N-isopropyl-2-(diphenylphosphinothioylthio)-2-methylpropan-1-iminium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In tetrachloromethane at 0 - 20℃; for 54h; Inert atmosphere; N-tert-Butyl-2-(diphenylphosphinothioylthio)-2-methylpropan-1-iminium chloride (10a) General procedure: Acid 7, 10.53 g (0.042 mol), was added in portions with stirring under dry argon to a solution of 8.17 g (0.05 mol) of imine 8a in 60 mL CCl4, maintaining the temperature at 0-3°. The reaction mixture was then let to warm up to 20°, stirred for 6 h, and allowed to stand at a room temperature for 48 h. The solvent and excess chlorimine were removed in a vacuum, the residue was treated with diethyl ether and cooled down. The crystals were filtered off. Yield 15.8 g (91%).
81% In tetrachloromethane at 0 - 20℃; Inert atmosphere; Reaction of diphenyldithiophosphinic acid (17) with N-tert-butyl-2-chloro-2-methylpropanimine (9a) General procedure: To a stirred solution of imine 9a (8.17 g, 50 mmol) in CCl4 (60 mL), acid 17 (10.53 g, 42 mmol) was added by portions under an argon flow maintaining the reaction temperature at 0-3 °C. Then the reaction temperature was raised to 20 °C and stirring was continued for additional 6 h. The reaction mixture was kept at room temperature for 48 h and the volatiles (solvent and chlorimine excess) were removed in vacuo. The residue was treated with diethyl ether and cooled down, the crystals formed were collected by filtration to give iminium salt 20a. Reaction of diphenyldithiophosphinic acid (17) with 2-chloro-N-isopropyl-2-methylpropanimine (9b) was performed as described above using imine 9b (4.67 g, 32 mmol) in CCl4 (30 mL) and acid 17 (6.15 g, 25 mmol) to obtain compound 20b in the yield of 7.9 g (81%), m.p. 102-103 °C. 1H NMR (CDCl3), δ: 1.52 (d, 6 H, CHMe2, 3JHH = 6.4 Hz); 1.79 (s, 6 H, CMe2); 4.09 (m, 1 H, NCH); 7.87 (dd, 4 H, ortho-CH(arom), 3JHH = 7.2 Hz, 3JPH = 14.4 Hz); 7.47-7.53 (m, 6 H, meta- and para-CH(arom)); 8.83 (br.s, 1 H, CH=N+); 15.22 (br.s, 1 H, N+H). 31P NMR (CDCl3), δ: 56.33. Found (%): C, 57.21; H, 6.47; P, 7.57; S, 16.24. C19H25ClNPS2. Calculated (%): C, 57.34; H, 6.33; P, 7.78; S, 16.11.
  • 50
  • [ 1015-38-9 ]
  • [ 78827-38-0 ]
  • N-isopropyl-2-[(diphenylphosphinothioyl)sulfanyl]-1,2-dimethylpropan-1-iminium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In dichloromethane at 5 - 20℃; for 53h; Reaction of diphenyldithiophosphinic acid (2) with N-isopropyl-3-chloro-3-methyl-2-butanimine (14). To a stirred solution of imine 14 (5.35 g, 33 mmol) in CH2Cl2 (50 mL), acid 2 (6.25g, 25 mmol) was added maintaining the reaction temperature at 5 °C. After warming up to room temperature, the reaction mixture was stirred for 5 h. In 48 h, the upper oily layer was separated and the volatiles were removed in vacuo (0.06 Torr) to give iminium salt 18b as a very thick oil. Yield 8.4 g (82%). 1NMR, δ: 1.67 (d, 6 H, Me2CH, 3JH,H = 6.4 Hz); 1.83 (s, 6 H, CMe2); 2.73 (s, 3 H, ); 4.20 (quint, 1 H, CHMe2, 3JH,H = 6.4 Hz); 7.47-7.50 (m, 6 H, meta- and para-CHarom); 7.87 (dd, 4 H, ortho-CHarom, 3JH,H = 7.2 Hz, 3JP,H = 14.4 Hz); 13.13 (br.s, 1 H, N+H). 31P NMR (CCl4), δ: 57.26. Found (%): C, 58.09; H, 6.74; P, 7.39; S, 15.41. C20H27ClNPS2. Calculated (%): C, 58.31; H, 6.61; P, 7.52; S, 15.57.
  • 51
  • [ 1015-38-9 ]
  • [ 603-33-8 ]
  • bismuth tris(diphenylphosphinodithioate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In ethanol at 60℃; for 0.333333h; Inert atmosphere; Schlenk technique; Microwave irradiation; Bismuth Tris(diphenylphosphinodithioate) [Bi(SP(=S)Ph2)3] (4) Diphenylphosphinodithioic acid (3 equiv.) was added to an ethanol solution of BiPh3 (1 equiv.) and treated under microwave (150 W) at 60 °C for 20 min. The resultant yellow colour solid was filtered and washed with cold ethanol. The single crystals (0.421 g, 88% yield) suitable for X-ray crystal diffractionstudies were obtained from DMSO. Mp 167 °C (dec.). νmax (FT-IR)/cm-1 3052 w, 2679 w, 2192 w, 2123 w, 1893 w,1808 w, 1577 w, 1480 m, 1437 s, 1336 w, 1308 m, 1185 m,1162 w, 1100 s, 1071 w, 1026 m, 1000 m, 924 w, 847 w, 746 s,706 s, 689 s, 629 m, 605 s. δH (400 MHz, DMSO-d6, 25 °C) 7.75(m, 12H, o-CH), 7.51 (m, 6H, m-CH), 7.45 (m, 12H, p-CH). δP (a00 MHz, DMSO-d6, 25 °C) 58.81. δC (100 MHz, DMSO-d6, 25 °C) 137.0 (CP), 131.1 (p-CH), 130.1 (o-CH, m-CH(Ph), o-CH(Ph)), 127.8 (m-CH3, p-CH(Ph)). m/z (ESI)+ 707.0 (25 %) [Bi(SP(=S)Ph2)2]+. Anal. Calc. for C36H30BiP3S6: C 45.19, H3.16. Found: C 45.32, H 2.82 %.
  • 52
  • [ 1015-37-8 ]
  • [ 14278-72-9 ]
  • [ 1015-38-9 ]
YieldReaction ConditionsOperation in experiment
44% Stage #1: diphenylthiophosphinoyl chloride With sodium hydrogen sulfide In water at 95℃; for 1h; Stage #2: With hydrogenchloride In water Diphenylphosphinodithioic Acid, HSP(=S)Ph2 ClP(=S)Ph2 was synthesised as described above and the yellow oil was used immediately and not isolated. The yellow oil was slowly added to a hot solution of NaHS (2 equiv., 0.1 mol) in water. After a retardation period, H2S evolution started and continued until the addition was completed. The reaction mixture was stirred at 95 °C for another 1 h. The reaction mixture was then transferred to a conical flask containing 100 g of ice. Once the reaction mixture was cooled to room temperature methyl tert-butyl ether (200 mL) was added, followed by the slow addition of concentrated hydrochloric acid (1.1 equiv.,0.055 mol) to the stirred solution. The organic phase was extracted and dried over anhydrous MgSO4. Upon removal of the solvent, a colourless solid was isolated (9.10 g). The isolatedsolid contained HSP(=S)Ph2 and HSP(=O)Ph2 in a 3 : 2 ratio. HSP(=S)Ph2 was isolated by washing with toluene (HSP(=O)Ph2 is insoluble in toluene while HSP(=S)Ph2 ishighly soluble) to give 5.46 g, 44% yield. νmax (FT-IR)/cm-1 3053 m, 2917 w, 2346 m, 2116 w, 1437 s, 1335 w, 1311 m,1185 w, 1099 s, 1073 w, 1000 m, 891 m, 749 m, 716 s, 689 s, 632 s, 616 s, 589 m. δH (400 MHz, CDCl3) 7.89-7.83 (m, 4H), 7.50-7.46 (m, 2H), 7.41-7.36 (m, 4H). δP (100 MHz, CDCl3) 80.22. m/z (ESI)- 249.0 (100 %).
  • 53
  • [ 1015-38-9 ]
  • [ 312329-87-6 ]
  • 1-(4-methyl-N-phenylphenylsulfonamido)vinyl diphenylphosphinodithioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With cetyltrimethylammonim bromide In water at 25 - 34℃; for 12h; Green chemistry;
Same Skeleton Products
Historical Records