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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 : |
|
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 |
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 |
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 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
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 |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.84 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With methyl thiocyanate In diethyl ether for 24h; Ambient temperature; | |
With benzonitrile | ||
With dicyclohexyl-carbodiimide In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 50-100 mmol; chlorine In tetrachloromethane 1) 0 deg C, 2) 30 min, r.t.; | |
With chlorine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With aluminium trichloride; tetraphosphorus decasulfide | |
41% | With diphosphorus pentasulfide; aluminium trichloride | |
With aluminium trichloride; tetraphosphorus decasulfide |
With aluminium trichloride; tetraphosphorus decasulfide | ||
With aluminum (III) chloride; tetraphosphorus decasulfide |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium hydroxide In benzene at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In benzene for 0.25h; ice-cooling; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In toluene at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In toluene at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In toluene at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With diphenyldithiophosphonic acid In isopropyl alcohol at 58℃; for 38h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With silver tetrafluoroborate In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: chlorine / beim anschliessenden Erhitzen mit rotem Phosphor |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In 1,2-dimethoxyethane at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In 1,2-dimethoxyethane at 20℃; for 1h; | |
86% | In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In 1,2-dimethoxyethane at 20℃; for 1h; | |
76% | In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In 1,2-dimethoxyethane at 20℃; for 1h; | |
91% | In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In 1,2-dimethoxyethane at 20℃; for 1h; | |
97% | In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In 1,2-dimethoxyethane at 20℃; for 1h; | |
88% | In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In 1,2-dimethoxyethane at 20℃; for 1h; | |
97% | In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In 1,2-dimethoxyethane at 20℃; for 1h; | |
63% | In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In 1,2-dimethoxyethane at 20℃; for 1h; | |
95% | In 1,2-dimethoxyethane at 25℃; for 1h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In ethanol at 25℃; for 5h; Inert atmosphere; optical yield given as %de; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In ethanol at 25℃; for 5h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In ethanol at 25℃; for 5h; Inert atmosphere; optical yield given as %de; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In ethanol at 25℃; for 5h; Inert atmosphere; optical yield given as %de; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In ethanol at 25℃; for 5h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In ethanol at 25℃; for 5h; Inert atmosphere; optical yield given as %de; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In ethanol at 25℃; for 5h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In ethanol at 25℃; for 5h; Inert atmosphere; optical yield given as %de; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In toluene at 100℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In toluene at 100℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In toluene at 100℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In toluene at 100℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With water-d2 In toluene at 100℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 2,6-di-tert-butyl-4-methylpyridine In toluene at 100℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In toluene at 100℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In toluene at 100℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In toluene at 100℃; for 1h; regioselective reaction; |
Yield | Reaction Conditions | Operation 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+). |
Yield | Reaction Conditions | Operation 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+). |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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%). |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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 %. |
Yield | Reaction Conditions | Operation 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 %). |