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Chemical Structure| 65600-74-0
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Product Details of [ 65600-74-0 ]

CAS No. :65600-74-0 MDL No. :MFCD00460154
Formula : C7H17O4P Boiling Point : -
Linear Structure Formula :- InChI Key :ZKNJRUPWSFSOFM-UHFFFAOYSA-N
M.W :196.18 Pubchem ID :11019774
Synonyms :

Safety of [ 65600-74-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
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Application In Synthesis of [ 65600-74-0 ]

* 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.

  • Upstream synthesis route of [ 65600-74-0 ]
  • Downstream synthetic route of [ 65600-74-0 ]

[ 65600-74-0 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation in experiment
56% With ammonium hypophosphorous acid; methanesulfonic acid In ethanol; toluene at 0 - 10℃; for 2 - 2.5 h; Synthesis of ethyl (diethoxymethyl) phosphinate using methane sulphonic acid; Triethylorthoformate (42.1 mL, 253 mmol, 2.1 eq) was added to a cold (00C) mixture of finely ground ammonium hypophosphite (10 g, 120 mmol, 1.0 eq), toluene (50 mL) and ethanol (3.5 mL) under a nitrogen atmosphere. The slurry was inerted and cooled to about 00C. Methane sulphonic acid (8.4 mL, 127 mmol, 1.05 eq) was charged (exotermic) during 4 minutes (T; was kept below 1O0C). The slurry was stirred at 00C and after 1 hour GC- analysis showed 93percent conversion from the ethylester to the desired product. After 2 hours, the reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate (37 mL). After phase separation the organic layer was concentrated under reduced pressure at 400C to a colourless liquid containing ~50percent toluene (28.0 g, GC-purity 95percent, assay 51.2percent). (Amount of ethyl (diethoxymethyl) phosphinate: 14.3 g, 73.1 mmol, yield -61percent). 13C-NMR (CD3CN): δ 14.2 (2 x CH3), 15.4 (CH3), 62.4+62.5 (CH2O), 64.5+64.6 (CH2O), 64.9+65.0 (CH2O) and 99.1+100.5 (CHO2). 31P-NMR: 8 26.8 (ddd). Synthesis of ethyl (diethoxyraethyl) phosphinate using methane sulphonic acid in 2-L- scale; Triethylorthoformate (632 mL, 3.80 mol, 2.1 eq) was added to a cold (O0C) mixture of ammonium hypophosphite (150 g, 1.81 mol, 1.0 eq), toluene (750 mL) and ethanol (75 mL) under a nitrogen atmosphere. The slurry was inerted and cooled to ~0°C. Methane sulphonic acid (126 mL, 1.90 mol, 1.05 eq) was charged (exothermic) during 8 minutes (Tj was kept below 1O0C). The slurry was stirred at O0C and after 1 hour GC-analysis showed 90percent conversion from the ethylester to the desired product. After 1.5 hours, the reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate (600 mL). After phase separation the organic layer was concentrated under reduced pressure at 4O0C to a colourless liquid containing ~65percent toluene (579 g, GC-purity 88percent, assay 34.4percent). (Amount of ethyl (diethoxymethyl) phosphinate: 199.2 g, 1.02 mol, yield -56percent).Synthesis of ethyl (diethoxymethyl) phosphinate using methane sulphonic acid in 500- L-scale; Triethylorthoformate (133.6 kg, 901.4 mol, 2.1 eq) was charged to a cold (00C), vigorously stirred mixture of ammonium hypophosphite (35.6 kg, 429.2 mol, 1.0 eq), toluene (107 L) and ethanol (11 L) under a nitrogen atmosphere. The slurry was carefully inerted while cooled to -O0C. The slurry was then continuously purged with nitrogen in order to reduce the amount of oxidized by-products. Methane sulphonic acid (43.3 kg, 450.7 mol, 1.05 eq) was then charged (exotermic) during 30 minutes (T; was kept below 1O0C). The slurry was stirred at O0C and after 2.5 hours the reaction mixture was quenched by a controlled charge (Tj < 1O0C) of a mixture with sodium hydrogen carbonate (14.4 kg, 171.7 mol, 0.4 eq) and water (128 L). The charging vessel was rinsed with water (14 L) and the reaction mixture was stirred vigorously during 10 minutes After phase separation the organic layer was concentrated under reduced pressure at 4O0C to ~l/3 of the volume. (82 L, 0.991 kg/ L, 81.3 kg, GC-purity 89.6 percent, assay 61 percent). (Amount of ethyl (diethoxymethyl) phosphinate: 49.6 kg, 252.7 mol, yield 58.9 percent).
44% With ammonium hypophosphorous acid; sulfuric acid In ethanol; toluene at 20℃; Synthesis of ethyl (diethoxymethyl) phosphinate using sulphuric acid Concentrated sulphuric acid (1.65 mL, 29.7 mmol, 0.5 eq) was charged to a mixture of ammonium hypophosphite (5 g, 60.2 mmol, 1 eq), toluene (45 mL) and ethanol (5 mL) at ambient temperature. After 2 hours triethylorthoformate (26.0 mL, 156.3 mmol, 2.6 eq) was added and the slurry was stirred over night. GC-analysis showed almost complete conversion of the intermediate ethylester to the desired product. The reaction mixture was then quenched with a 1 : 1 mixture of saturated aqueous sodium hydrogen carbonate and brine (50 mL). The phases were separated and the organic layer was washed twice, first with the 1:1 mixture of saturated aqueous sodium hydrogen carbonate and brine (50 mL) and then with only brine (25 mL). The organic layer was then dried (Na2SO4) and concentrated under reduced pressure. Ethyl (diethoxymethyl) phosphinate was isolated as a colourless oil. (5.7 g, GC-purity ~ 93percent, yield ~ 44percent).
Reference: [1] European Journal of Organic Chemistry, 2009, # 34, p. 6048 - 6054
[2] Journal of Organic Chemistry, 2008, vol. 73, # 22, p. 8987 - 8991
[3] Chemistry - A European Journal, 2008, vol. 14, # 20, p. 6049 - 6052
[4] Tetrahedron, 1999, vol. 55, # 3, p. 771 - 780
[5] Patent: WO2006/31180, 2006, A1, . Location in patent: Page/Page column 3-5
[6] Tetrahedron Letters, 1992, vol. 33, # 35, p. 5133 - 5136
[7] Patent: WO2006/31180, 2006, A1, . Location in patent: Page/Page column 5
[8] Australian Journal of Chemistry, 1980, vol. 33, # 2, p. 287 - 294
[9] Journal of Medicinal Chemistry, 1995, vol. 38, # 17, p. 3313 - 3331
[10] Patent: WO2006/31180, 2006, A1, . Location in patent: Page/Page column 5
[11] Patent: WO2006/31180, 2006, A1, . Location in patent: Page/Page column 5-6
[12] Patent: US4933478, 1990, A,
[13] Patent: US4933478, 1990, A,
[14] Synlett, 2008, # 14, p. 2142 - 2146
[15] Tetrahedron Letters, 2014, vol. 55, # 27, p. 3706 - 3708
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YieldReaction ConditionsOperation in experiment
61% for 24 h; Heating / reflux Preparation of ethvKdiethoxymethvDphosphinateIn a previously deoxygenated three-necked flask were introduced under nitrogen 14.2 g of hypophosphorous acid (0.215 mol), 80 ml of methyl oformate (0.48 mol, 2.2 eq.) and 7.4 g of p-toluene-sulfonic acid (0.043 mol, 0.2 eq.). The medium was then refluxed for 24 hours. The reaction medium in a first step was taken up in 200 ml of chloroform and washed with a sodium hydrogenocarbonate saturated solution. After drying The organic phase was evaporated using the vane pump, the resulting oil was then distilled under reduced pressure (0.02 mmHg, 100 <) g) 3.161H NMR (400.13 MHz, CDCI3): ? 1 .20 (t, 3H, 3JH-H = 3.4 Hz, 4CH3), 1 .22 (t, 3H, 3JH-H = 3.4 Hz, 6CH3), 1 .34 (t, 3H, 3JH-H = 3.6 Hz, 8CH3), 3.62 -3.82 (m, 4H, 3CH2* 5CH2), 4.07 -4.28 (m, 2H, 7CH2), 4.67 (d, 1 H, 2JP_H = 23.1 Hz, 2CH), 6.91 (d, 1 H, 1JP_H = 560.0 Hz, 1P-H).
Reference: [1] Patent: WO2009/4096, 2009, A1, . Location in patent: Page/Page column 27-28
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  • [ 14684-32-3 ]
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Reference: [1] Journal of Organometalic Chemistry, 2002, vol. 643-644, p. 381 - 391
[2] Journal of Organometalic Chemistry, 2002, vol. 643-644, p. 381 - 391
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