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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
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CAS No. : | 707-61-9 | MDL No. : | MFCD00014518 |
Formula : | C11H13OP | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YMKWWHFRGALXLE-UHFFFAOYSA-N |
M.W : | 192.19 | Pubchem ID : | 69722 |
Synonyms : |
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Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P273-P301+P312+P330 | UN#: | 2811 |
Hazard Statements: | H302-H350-H412 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* 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 |
---|---|---|
100% | With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 15001.5 Torr; | Synthetic Procedures; Preparation of Compound (1): 3-methyl-l-phenylphospholane-l-oxide,; Rapidly, in air, commercially available 3-methyl-l -phenyl -2-phospholene-l -oxide (3.0 g, 16 mmol, CAS 707-61-9) was weighed into a tared 500 mL round-bottom flask. Methanol (300 mL) was added to prepare a 0.05 M solution. The phospholene oxide was hydrogenated via the H-Cube Midi with a catalyst cartridge containing 10% Pd/C. The reduction occurred at ambient temperature, under 20 bar H2, at 1 mL/min flow rate. Methanol was removed in vacuo to yield the product as a viscous 2: 1 mixture of diastereomers in 100% yield. 1H-NMR and 31P-NMR spectra match previously reported data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane; In toluene; at 100℃; for 40h;Inert atmosphere; Sealed tube; | General procedure: In a sealed tube containing a solution of the phosphine oxide derivative (5 mmol) in anhydrous toluene (1 M) was added InBr3 (1 mol %, 0.05 mmol) and the TMDS (1.5 equiv, 7.5 mmol) under an argon atmosphere. The reaction mixture was stirred at 100 C during 7-40 h depending on the substrate (the reaction was monitored by 31P NMR). After complete consumption of the reagent the mixture was kept under argon in the sealed tube and cooled to 0 C. A solution of BH3.SMe2 (2 M in THF, 1 equiv) was then slowly added. After 1 h at room temperature, 31P NMR analysis of an aliquot indicates complete conversion to phosphine borane adduct. The crude was poured in an erlenmeyer flask and silica gel was carefully added while stirring. When silica gel was added in the reaction mixture, a slightly exothermic reaction was observed. The reaction mixture was then filtered on silica gel and washed several times with ethyl acetate. After evaporation of the ethyl acetate, the residue was purified by flash chromatography on silica gel with pure cyclohexane to afford the desired phosphine-borane. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | EXAMPLE 10 The reaction sequence, including working up, described in Example 2 is repeated with 358 g of phenyl dichlorophosphine instead of methyl dichlorophosphine. The yield of 1-phenyl-3-methyl-1-oxophospholine amounts to 177 g (46% of the theoretical yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With manganese(IV) oxide; bromine; In dichloromethane; at 20℃; for 12h; | <strong>[707-61-9]3-Methyl-1-phenyl-2-phospholene 1-oxide</strong> (0.27 g, 1.4 mmol; 1.0 eq.) was dissolvedin CH2Cl2 (5 mL), and added MnO2 (0.24 g, 2.8 mmol; 2.0 eq.). To the mixture was addedCH2Cl2 (10 mL) solution of bromine (0.4 mL; 7.8 mmol; 5.7 eq.) dropwisely and stirredfor 12 h at room temperature. The reaction mixture was treated with saturated sodiumhydrogensulfite solution and was extracted with CHCl3. The CHCl3 extract was washedwith saturated sodium hydrogen carbonate, brine, and water, and then dried over anhydrousNa2SO4. Evaporation of the solvent from the solution of the product followed by silica gelcolumn chromatography with the mixed eluent of chloroform and methanol (30:1) afforded2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide (DBMPP; 0.38 g, 1.1 mmol) in 78%yield; TLC: Rf = 0.54 (CHCl3 :MeOH = 30 : 1); MS (m/z), 351.5 (MH+, 60), 353.5 (MH+,100), 355.5 (MH+, 40); 1H-NMR (CDCl3, 300 MHz), δ = 2.09 (s, 3H, C3-CH3), 2.44-2.58(m, 2H, C5), 2.60-2.85 (m, 2H, C4), 4.66-4.68 (dd, 1H, C2), 7.49-7.80 (m, 5H, Ph). |