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Structure of 24630-67-9

Chemical Structure| 24630-67-9

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Product Details of [ 24630-67-9 ]

CAS No. :24630-67-9
Formula : C3H9O4P
M.W : 140.08
SMILES Code : COP(=O)(CO)OC
MDL No. :MFCD11053766
InChI Key :OIERWUPLBOKSRB-UHFFFAOYSA-N
Pubchem ID :11051732

Safety of [ 24630-67-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 24630-67-9 ]

* 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 [ 24630-67-9 ]

[ 24630-67-9 ] Synthesis Path-Downstream   1~35

  • 6
  • [ 110-87-2 ]
  • [ 24630-67-9 ]
  • O,O-dimethyl-2-(tetrahydropyranyloxy)methyl phosphonate [ No CAS ]
  • 7
  • [ 103-75-3 ]
  • [ 24630-67-9 ]
  • (6-Ethoxy-tetrahydro-pyran-2-yloxymethyl)-phosphonic acid dimethyl ester [ No CAS ]
  • 8
  • [ 332-19-4 ]
  • [ 24630-67-9 ]
  • (6-Butoxy-tetrahydro-pyran-2-yloxymethyl)-phosphonic acid dimethyl ester [ No CAS ]
  • 9
  • [ 71098-88-9 ]
  • [ 24630-67-9 ]
  • [ 132178-50-8 ]
  • [ 132204-43-4 ]
  • 11
  • [ 24630-67-9 ]
  • [ 2241-68-1 ]
  • 1-(dimethylphosphono)methyl bis(1,1,3-trihydroperfluoropropyl) phosphite [ No CAS ]
  • 13
  • [ 24630-67-9 ]
  • [ 134361-23-2 ]
  • [ 134361-24-3 ]
  • 14
  • [ 24630-67-9 ]
  • [ 132178-50-8 ]
  • [ 132178-51-9 ]
  • 15
  • [ 24630-67-9 ]
  • [ 132178-45-1 ]
  • [ 132178-47-3 ]
  • 16
  • [ 24630-67-9 ]
  • [ 85233-01-8 ]
  • 2-(α-O,O-dimethylphosphono)methyl-4,5-benzo-1,3,2-dioxaphospholane [ No CAS ]
  • [ 76-05-1 ]
  • 19
  • [ 868-85-9 ]
  • sodium hydroxymethylaminoacetate [ No CAS ]
  • [ 24630-67-9 ]
  • [ 65886-96-6 ]
  • [ 13590-71-1 ]
  • 20
  • [ 868-85-9 ]
  • [ 24630-67-9 ]
  • [ 65886-96-6 ]
  • [ 13590-71-1 ]
  • 22
  • [ 24630-67-9 ]
  • [ 7354-93-0 ]
  • [ 17331-67-8 ]
  • 23
  • [ 69412-44-8 ]
  • [ 76-05-1 ]
  • [ 24630-67-9 ]
  • dimethyl-α-dimethylphosphono-β,β,β-trifluoroethyl phosphate [ No CAS ]
  • 25
  • [ 50-00-0 ]
  • [ 96-36-6 ]
  • [ 24630-67-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; at 70℃; for 1h; (R)-tert-Butoxycarbonylamino-[4-(dimethoxy-phosphorylmethoxy)-phenyl]-acetic acid was prepared as follows:; (1) Dimethyl phosphite (2.0 g, 18.2 mmol), paraformaldehyde (574 mg, 19.1 mmol) and triethylamine (0.25 mL, 1.8 mmol) were combined and heated to 70 C. to give a clear solution. After 1 hour the reaction was cooled and concentrated in vacuo overnight to afford the crude hydroxymethyl-phosphonic acid dimethyl ester (2.5 g).
  • 26
  • [ 358-23-6 ]
  • [ 24630-67-9 ]
  • [ 96851-20-6 ]
YieldReaction ConditionsOperation in experiment
83% With 2,6-dimethylpyridine; In dichloromethane; at -50 - 0℃; for 1.5h; Trifluoromethanesulfonic anhydride (4.7 ml, 27.8 mmol) was added in a dropwise manner to a stirred solution of dimethy phosphonic ester alcohol (3.54 g, 25.3 mmol) and 2,6-lutidene (3.5 ml, 30.3 mmol) in dichloromethane (30 ml) ensuring that the internal temperature remained below -50 C. Once the addition was complete the mixture was slowly warmed to 0 C over approximately 90 minutes. Diethyl ether (150 ml) was then added and the resultant suspension was filtered through celite andwashed with diethyl ether (20 ml). The solution was then sequentially washed with water (90 ml), 1M hydrochloric acid (90 ml) and brine (90 ml). After drying (NaaSC^), filtration followed by concentration provided the title compound as a light yellow oil (5.67 g, 83%) which was used without further purification.'H NMR (400 MHz, CDC13) 8 ppm 4.87 (2H5 d, J9 Hz), 3.91 (3H, s) and 3.89 (3H, s)19F{.H} NMR (376.5 MHz, CDC13) 8 ppm -74.531P{JH} NMR (400.1 MHz, CDC13) 8 ppm 16.1
53% With pyridine; In dichloromethane; at -20 - 0℃; for 0.5h; (2) To a solution of <strong>[24630-67-9]hydroxymethyl-phosphonic acid dimethyl ester</strong> (2.0 g, 14.5 mmol) in anhydrous dichloromethane (50 mL) at -20 C. was added pyridine (1.4 mL, 16.7 mmol) followed by trifluoromethanesulfonic anhydride (2.7 mL, 15.9 mmol). After stirring at 0 C. for 0.5 hours, the mixture was filtered through celite with a thin layer of silica gel. The filtrate was washed with cold 1.0 N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and dried over sodium sulfate. The solvents were removed to give trifluoro-methanesulfonic acid dimethoxy-phosphorylmethyl ester as an oil (2.1 g, 53%).
In dichloromethane; at -78 - 20℃; for 1h; A solution of dimethoxyphosphorylmethanol (1 g) in dichloromethane (20 mL) was cooled to -78C and 2,6-Lutidine (1.32 mL) followed by trifluoromethylsulfonyl trifluoromethanesulfonate (1.91g) was added. The resulting reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was poured into water and extracted with dichloromethane (50 mL). The organic layer was washed with 1 M aqueous hydrochloric acid (50 mL), dried over anhydrous sodium sulfate and concentrated to give dimethoxyphosphorylmethyl trifluoromethanesulfonate as a pale yellow liquid. 1 H NMR (400 MHz, de-DMSO) 4.82 (d, 2H) 3.78 (s, 3H) 3.74 (s, 3H)
  • 28
  • [ 24630-67-9 ]
  • [ 135911-57-8 ]
  • [(3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-iodomethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yloxymethyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 29
  • [ 24630-67-9 ]
  • [ 135911-57-8 ]
  • [(3S,5R)-2-Bromomethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yloxymethyl]-phosphonic acid diisopropyl ester [ No CAS ]
  • 30
  • [ 24630-67-9 ]
  • [ 135911-57-8 ]
  • [ 183279-88-1 ]
  • [ 183505-84-2 ]
  • 31
  • [ 24630-67-9 ]
  • [ 183279-94-9 ]
  • [(3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-iodomethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yloxymethyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 32
  • [ 50-00-0 ]
  • [ 868-85-9 ]
  • [ 24630-67-9 ]
YieldReaction ConditionsOperation in experiment
62% With triethylamine; at 100℃; for 2.5h; A stirred mixture of dimethylphosphite (10.0 ml, 109 mniol), triethylamine (1.5 ml, 10.9 mmol) and paraformaldehyde (3.26 g) was heated in an oil bath at 100 C (external temperature). After 2.5 hours the mixture was cooled to room temperature, concentrated in vacua and the residue was purified by flash column chromatography (eluent: ethyl acetate/methanol 95:5) to provide the title compound as a colourless oil (9.41 g, 62%).'H NMR (400 MHz, CDC13) 5 ppm 4.32 (1H, br s), 3.95 (2H, d, J6 Hz), 3.83 (3H, s) and 3.81 (3H,s).31P{1H} NMR (400.1 MHz, CDC13) 5 ppm 27.8.13C NMR (100.6 MHz, CDC13) 8 ppm 53.5, 56.0 and 57.6.
With triethylamine; at 70℃; for 1h; Dimethyl phosphite (2.0 g, 18.2 mmol), paraformaldehyde (574 mg, 19.1 mmol) and triethylamine (0.25 mL, 1.8 mmol) were combined and heated to 70 C. to give a clear solution. After 1 hour the reaction was cooled and concentrated in vacuo overnight to afford the crude hydroxymethyl-phosphonic acid dimethyl ester (2.5 g).
With potassium carbonate; In methanol; at 0 - 20℃; for 1h; In the first step, 1.75 g (55 mmol) of paraformaldehyde was dissolved in 50 mL of methanol, 0.63 g (4.54 mmol) of potassium carbonate was added and the solution was cooled to 0 C. 5.0 g (45.4 mmol) of phosphorous acid And the temperature was raised to room temperature. After 1 h, the potassium carbonate was filtered off and the filtrate was removed under reduced pressure to give a colorless oil as Intermediate I;
1.38 g of anhydrous potassium carbonate,6.01g of paraformaldehyde and 100ml of methanol were sequentially added to the reflux condenser equipped withMagnetic stirrer inside the three-necked flask of the thermometer,After stirring for 10 minutes, dimethyl phosphite (22.01g) was added dropwise to the three-necked flask.Control the dripping speed to avoid the reaction solution from boiling. After the dropwise addition is complete, react for one hour at room temperature;After the reaction is completed, the remaining potassium carbonate particles are removed by filtration, and the solvent is removed by rotary evaporation. Then,Put in vacuum oven, 60 , 12h,The obtained colorless transparent liquid is the product dimethyl methyl phosphinate.

  • 34
  • [ 17435-77-7 ]
  • [ 24630-67-9 ]
  • 2-(dimethoxy-phosphorylmethoxymethyl)-acrylic acid ethyl ester [ No CAS ]
  • 35
  • [ 24630-67-9 ]
  • [ 79-04-9 ]
  • chloro-acetic acid dimethoxy-phosphorylmethyl ester [ No CAS ]
 

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