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[ CAS No. 1066-51-9 ] {[proInfo.proName]}

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Chemical Structure| 1066-51-9
Chemical Structure| 1066-51-9
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Product Details of [ 1066-51-9 ]

CAS No. :1066-51-9 MDL No. :MFCD00008105
Formula : CH6NO3P Boiling Point : -
Linear Structure Formula :- InChI Key :MGRVRXRGTBOSHW-UHFFFAOYSA-N
M.W : 111.04 Pubchem ID :14017
Synonyms :

Calculated chemistry of [ 1066-51-9 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 20.62
TPSA : 93.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -10.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.45
Log Po/w (XLOGP3) : -4.72
Log Po/w (WLOGP) : -0.92
Log Po/w (MLOGP) : -2.45
Log Po/w (SILICOS-IT) : -0.54
Consensus Log Po/w : -1.82

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : 2.51
Solubility : 36000.0 mg/ml ; 324.0 mol/l
Class : Highly soluble
Log S (Ali) : 3.39
Solubility : 270000.0 mg/ml ; 2430.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 1.27
Solubility : 2060.0 mg/ml ; 18.5 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.88

Safety of [ 1066-51-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1066-51-9 ]

* 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 [ 1066-51-9 ]

[ 1066-51-9 ] Synthesis Path-Downstream   1~93

  • 1
  • [ 64-67-5 ]
  • [ 1066-51-9 ]
  • [ 67910-53-6 ]
  • triethylammoniomethyl phosphonate [ No CAS ]
  • 2
  • [ 5332-26-3 ]
  • [ 122-52-1 ]
  • [ 1066-51-9 ]
  • 4
  • [ 50-00-0 ]
  • [ 1066-51-9 ]
  • 7
  • [ 27167-53-9 ]
  • [ 1066-51-9 ]
  • [((R)-2-Benzyloxycarbonylamino-propionylamino)-methyl]-phosphonic acid [ No CAS ]
  • 8
  • [ 1066-51-9 ]
  • [ 24424-99-5 ]
  • N-t-butoxycarbonylaminomethylphosphonic acid [ No CAS ]
  • 9
  • [ 1066-51-9 ]
  • [ 71922-16-2 ]
  • [(S)-2-(Benzyloxycarbonyl-methyl-amino)-propionylamino]-methyl}-phosphonic acid [ No CAS ]
  • 10
  • [ 1066-51-9 ]
  • [ 40465-45-0 ]
  • [ 139583-44-1 ]
  • 11
  • [ 1066-51-9 ]
  • [ 77004-75-2 ]
  • [ 148823-29-4 ]
  • 12
  • [ 1066-51-9 ]
  • [ 53114-57-1 ]
  • [ 55215-14-0 ]
  • 13
  • [ 1066-51-9 ]
  • [ 75902-92-0 ]
  • (Z)-2-[(2,2-Dimethyl-cyclopropanecarbonyl)-amino]-8-(phosphonomethyl-amino)-oct-2-enoic acid [ No CAS ]
  • 15
  • [ 3852-14-0 ]
  • [ 1066-51-9 ]
  • [ 6419-19-8 ]
  • 16
  • [ 6419-19-8 ]
  • [ 1066-51-9 ]
  • [ 2617-47-2 ]
  • [ 35869-68-2 ]
  • 17
  • [ 5994-61-6 ]
  • [ 64-18-6 ]
  • [ 1066-51-9 ]
  • [ 35404-71-8 ]
  • [ 1071-83-6 ]
  • [ 84767-96-4 ]
  • [ 68-12-2 ]
  • 18
  • [ 57637-97-5 ]
  • [ 1066-51-9 ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In methanol; water; EXAMPLE 6 14.4 g (0.094 mol) of acetylaminomethanephosphonic acid and 28 g of water were fed into a sealed tube and maintained at 200 C. for 20 hours. The mixture was then cooled, and the resulting reaction solution was freed in vacuo from water and acetic acid. The residue was digested with a mixture of 30 ml of methanol and 1 ml of water. 9.6 g (92% of theory) of aminomethanephosphonic acid of a decomposition point of 270-278 C. were obtained.
With water; In water-d2; at 100℃; for 8h; General procedure: A sample of 1-(N-acylamino)alkylphosphonic acid (AC)-AAP(0.50 mmol) was placed into 5 mL V-vials, and dissolved in5 mL of appropriate, fortifed with D2O solution (2 M HCl, water and/or acetate buer). The vials were thermostated at desiredtemperature [25 C ± 0.5 C (in water bath) or at 100 C ± 2 C(in oil bath)]. At various time intervals the vials were removedfrom the baths, and the samples of 0.5 mL were taken for 3lPNMR analysis. The concentration of the substrate and formedproducts were determined from the integration of its NMRsignal.
With potassium hydroxide; In water-d2; at 25℃; General procedure: A sample of (AC)-AAP (0.5 mmol) was placed into 5-mL V-vials, before being dissolved in 5 mLof appropriate solution fortified with D2O (2 M KOH). The vials were maintained at 25 C ± 0.2 C.At various time intervals, the vials were removed from the baths and the samples of 0.5 mL weretaken for 3lP NMR analysis. The concentration of the substrate and formed products weredetermined from the integration of its NMR signal.
  • 20
  • [ 20495-31-2 ]
  • [ 1066-51-9 ]
  • 23
  • [ 6282-02-6 ]
  • [ 1066-51-9 ]
  • 24
  • [ 26028-46-6 ]
  • [ 1066-51-9 ]
  • 25
  • [ 20495-33-4 ]
  • [ 1066-51-9 ]
  • 26
  • [ 30805-19-7 ]
  • [ 1066-51-9 ]
  • 27
  • [ 106938-62-9 ]
  • [ 1066-51-9 ]
  • 28
  • [ 77393-49-8 ]
  • [ 1066-51-9 ]
  • 29
  • [ 1066-51-9 ]
  • [ 501-53-1 ]
  • [ 55601-40-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In sodium hydroxide; sodium carbonate; i. Benzyloxycarbonylaminomethylphosphonic acid. To a solution of aminomethylphosphonic acid (2.5 g) in 2N aqueous sodium hydroxide (23 mL) containing sodium carbonate (4.77 g) and sodium bicarbonate (3.78 g) at 50 C. was added benzyl chloroformate (9.64 mL), portionwise over 1 h. The resulting solution was allowed to stir overnight. The solution was diluted with water (100 mL) and the pH lowered to 1. The product was extracted into ethyl acetate and the organic solvent dried (MgSO4). The solvent was evaporated and the product crystallized from ethyl acetate to provide the carbamate (4.64 g); MS: m/z=246(M+1).
  • 30
  • [ 50918-70-2 ]
  • [ 1066-51-9 ]
  • 31
  • [ 120060-80-2 ]
  • [ 1066-51-9 ]
  • 32
  • [ 2899-60-7 ]
  • [ 1066-51-9 ]
  • disodium N-[N'-(benzyloxycarbonyl)aminoacetyl]aminomethylphosphonate [ No CAS ]
  • 33
  • [ 106-31-0 ]
  • [ 1066-51-9 ]
  • (butyrylamino-methyl)-phosphonic acid [ No CAS ]
  • 34
  • [ 1066-51-9 ]
  • [ 3282-30-2 ]
  • [ 866605-67-6 ]
  • 35
  • [ 1066-51-9 ]
  • [ 123-62-6 ]
  • (propionylamino-methyl)-phosphonic acid [ No CAS ]
  • 36
  • [ 1071-83-6 ]
  • [ 1066-51-9 ]
YieldReaction ConditionsOperation in experiment
The precipitate was removed by filtration to leave a solution containing 1.0% w/w N-phosphonomethylglycine and 0.95%w/w aminomethylphosphonic acid. (i.e. 91% recovery of N-phosphonomethylglycine with no precipitation of aminomethylphosphonic acid). The filtrates from above (502.9g) were adjusted to PH 2.5 by the addition of caustic soda solution (2.7g at 47%).
  • 37
  • [ 5994-61-6 ]
  • N-(phosphonomethyl)-N-methyl glycine [ No CAS ]
  • [ 1066-51-9 ]
  • [ 1071-83-6 ]
YieldReaction ConditionsOperation in experiment
With oxygen; at 104.5 - 115.5℃; under 5171.62 Torr;Product distribution / selectivity; Experiments were conducted in a laboratory scale continuous trickle bed reactor. The reaction system was similar to that described in Example 1, except the reactor effluent was not returned to the feed mixing vessel. In each experiment, the reactor wall temperature was maintained at a constant value by continuously circulating hot oil through a jacket around the reactor, giving a nearly isothermal temperature in the catalyst bed. The catalyst bed contained 14.4 g of [20X50] mesh Nuchar RGC activated carbon catalyst. Experiments were conducted at various temperatures and liquid feed rates. The reactor pressure was 100 psia (689 [KPA),] and the oxygen flow rate was 200 sccm. The aqueous feed consisted of 2 weight % PMIDA and, optionally, 3.02 weight % PMG. The experiments with the additional PMG were used to simulate a partially converted 6 weight % PMIDA feed. For samples 1 and 2, the molar selectivities and fractional conversion are based on the simulated feed of 6 weight % PMIDA. The results are listed in Table 4, below. These data are GC results, normalized and then converted to molar selectivities and conversions.
  • 38
  • [ 1066-51-9 ]
  • [ 920-46-7 ]
  • N-methacryloyl-2-aminomethylphosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; at 0℃; In a reactor equipped with an agitator, 15 ml of water and 0.16 mol of sodium hydroxide were added. Then 0.0045 mol of aminoethylphosphonic acid, aminoethylphosphonic acid or aminopropylphosphonic acid (made by Tokyo Kasei Kogyo Co., Ltd.) was dissolved therein, and the amino group of aminomethylphosphonic acid, aminoethylphosphonic acid or aminopropylphosphonic acid was condensed with methacrylic chloride by dropping 0.045 mol of methacrylic chloride to the above solution while the reactor was cooled with ice. After completion of the reaction, hydrogen chloride gas was introduced while the reactor was cooled by adding methanol (made by Wako Pure Chemical Industries Ltd.) to adjust pH of the reaction layer at 0.4 or less. After separating deposited sodium chloride by filtration, the solution was dried by adding anhydrous sodium sulfate. After filtration, the solvent was distilled off under a reduced pressure. The residue was added with ethyl acetate and ethanol to crystallize N-methacryloyl-2-aminomethylphosphonic acid (NMMP), N-methacryloyl-3-aminoethylphosphonic acid (NMEP) or N-methacryloyl-4-aminopropylphosphonic acid (NMPP) followed by isolation and purification.(2) Results The NMR data of the compounds obtained are shown in Table 2 to Table 4. [Table 2:] Chemical shifts of the 13C NMR peaks assigned to NMMP CH2=>C<-CH3 -CO-NH-alpha -CH2-121.65139.1017.92171.8038.19 35.98[Table 3:] Chemical shifts of the 13C NMR peaks assigned to NMEP CH2=>C<-CH3 -CO-NH-beta-CH2-alpha -CH2-121.266139.4518.56170.2734.6128.3626.36[Table 4:] Chemical shifts of the 13C NMR peaks assigned to NMPP CH2=>C<-CH3 -CO-NH-gamma-CH2-beta-CH2-alpha-CH2-121.25139.29121.24172.0740.3122.4123.1440.0422.41
  • 39
  • [ 50655-38-4 ]
  • [ 1066-51-9 ]
YieldReaction ConditionsOperation in experiment
98%Turnov. The preparation of Example 13 was substantially repeated, but with an increased ratio of urea to HMPA. The conditions of the reaction, HMPA conversion, AMPA selectivity, iminobis (i.e., glyphosine) selectivity and phosphate selectivity are set forth below in Table 9 wherein T,h=reaction time in hours, and t, C=reaction temperature in degrees centigrade.
  • 40
  • CH3O4PPol2 [ No CAS ]
  • self-ester of HMPA [ No CAS ]
  • [ 13598-36-2 ]
  • bis-phosphonomethylimine [ No CAS ]
  • [ 1066-51-9 ]
  • [ 86119-84-8 ]
YieldReaction ConditionsOperation in experiment
0.9%Chromat.; 4.1%Chromat.; 93%Chromat.; 3.6%Chromat. To a sample of HMPA self-esters, prepared as described above in example 8 from 0.2975 g (2.13 mmol) of (OH)2P(O)CH2OH.1.4H2O at 120 C. for 2 hours, urea (1.245 g, 20.75 mmol) was added. The flask was immersed in an oil bath and heated to 185 C. for 15 hours with stirring under N2. To the reaction mixture 10 ml of 15% NaOH was added and the homogeneous solution was hydrolyzed for 10 hours under reflux. According to HPLC, AMPA was obtained in 93% yield with 3.6% H3PO4, O0.9% H3PO3, and 4.1% bis-phosphonomethylimine also detected.
  • 41
  • CH3O4PPol2 [ No CAS ]
  • self-ester of HMPA [ No CAS ]
  • [ 1066-51-9 ]
YieldReaction ConditionsOperation in experiment
90.6%Chromat. To a sample of HMPA self-esters, prepared as described above in the example 8 from 0.551 g (3.7 mmol) of (OH)2P(O)CH2OH.1.4H2O, 5.5 ml of N-benzylamine was added. The flask was immersed in an oil bath and heated to 180 C. for 16 hours with stirring. In the morning white crystals were present in the liquid. To the reaction, mixture 30 ml of 6% NaOH was added and a homogeneous solution was formed. Excess monobenzylamine was extracted by toluene (4×20 ml) and then ether (2×20 ml). The aqueous layer was diluted by water to 100 g, and 10 g of the solution was hydrogenolyzed under 90 psi H2 pressure in the presence of Pd(OH)2/C to give, according to HPLC, AMPA in 90.6% yield.
  • 42
  • CH3O4PPol2 [ No CAS ]
  • self-ester of HMPA [ No CAS ]
  • [ 6000-44-8 ]
  • [ 13598-36-2 ]
  • [ 1066-51-9 ]
  • [ 86119-84-8 ]
  • [ 1071-83-6 ]
YieldReaction ConditionsOperation in experiment
1.5%Chromat.; 1.1%Chromat.; 2.3%Chromat.; 16.7%Chromat. A sample of HMPA self-esters, prepared as described above in example 8 from 0.066 g (0.48 mmol) of (OH)2P(O)CH2OH.1.4H2O, was stirred with an excess of sodium glycinate (0.482 g, 4.97 mmol) in 2 ml of acetonitrile for about ten minutes, followed by removal of the solvent. The flask was immersed in an oil bath and heated to 180 C. for 16 hours with vigorous stirring. At the end of this time the reaction mixture was hydrolyzed by 24% HBr (10 ml) at 110 C. for 6 hours to give, according to HPLC, 16.7% glyphosate, 1.1% AMPA, 2.3% H3PO4, and 1.5% H3PO3 at 20% HMPA conversion.
  • 43
  • CH3O4PPol2 [ No CAS ]
  • self-ester of HMPA [ No CAS ]
  • [ 6000-44-8 ]
  • [ 13598-36-2 ]
  • [ 1066-51-9 ]
  • [ 2439-99-8 ]
  • [ 86119-84-8 ]
  • [ 1071-83-6 ]
YieldReaction ConditionsOperation in experiment
0.7%Chromat.; 1.2%Chromat.; 1.7%Chromat.; 2.2%Chromat.; 15.1%Chromat. A sample of HMPA self-esters, prepared as described above in example 8 from 0.106 g (0.775 mmol) of (OH)2P(O)CH2OH.1.4H2O was vigorously stirred with an excess of sodium glycinate (0.480 g, 4.96 mmol) in 1.5 ml of sulfolane at 180 C. for 16 hours. At the end of this time the reaction mixture was hydrolyzed by 24% HBr (10 ml) at 110 C. for 6 hours to give, according to HPLC, 15.1 % glyphosate, 1.2% AMPA, 2.2% H3PO4, 0.7% H3PO3, and 1.7% glyphosine at 20% HMPA conversion.
  • 44
  • CH3O4PPol2 [ No CAS ]
  • self-ester of HMPA [ No CAS ]
  • [ 6000-44-8 ]
  • [ 1066-51-9 ]
  • [ 2439-99-8 ]
  • [ 86119-84-8 ]
  • [ 1071-83-6 ]
YieldReaction ConditionsOperation in experiment
1.8%Chromat.; 1.9%Chromat.; 1.9%Chromat.; 18%Chromat. A sample of HMPA self-esters, prepared as described above in example 8 from 0.077 g (0.56 mmol) of (OH)2P(O)CH2OH.1.4H2O was vigorously stirred with an excess of sodium glycinate (0.488 g, 5.03 mmol) in 2 ml of 15-crown-5 ether at 178 C. for 16 hours. At the end of this time the reaction mixture was hydrolyzed by 24% HBr (10 ml) at 110 C. for 6 hours to give, according to HPLC, 18.0% glyphosate, 1.8% AMPA, 1.9% H3PO4, and 1.9% glyphosine at 23% HMPA conversion.
2.5%Chromat.; 0.7%Chromat.; 4.7%Chromat.; 30.3%Chromat. A sample of HMPA self-esters, prepared as described above in example 8 from 0.064 g (0.47 mmol) of (OH)2P(O)CH2OH.1.4H2O was vigorously stirred with excess of sodium glycinate (0.475 g, 4.90 mmol) in 2 ml of sulfolane in the presence of 0.219 g (1.46 mmol) of Nal at 150 C. for 94 hours. At the end of this time the reaction mixture was hydrolyzed by 24% HBr (10 ml) at 110 C. for 6 hours to give, according to HPLC, 30.3% glyphosate, 2.5% AMPA, 4.7% H3PO4, and 0.7% glyphosine at 36% HMPA conversion.
  • 45
  • [ 115989-10-1 ]
  • [ 1066-51-9 ]
YieldReaction ConditionsOperation in experiment
0.3% In a series of runs, HMPA was separately reacted with benzylamine, urea and formamide, in each case in the presence of a catalyst. The substrate, catalyst, conditions of the reaction and results are set forth in Table 15.
  • 46
  • [ 2617-47-2 ]
  • [ 1066-51-9 ]
YieldReaction ConditionsOperation in experiment
0% In a series of runs, HMPA was separately reacted with benzylamine, urea and formamide, in each case in the presence of a catalyst. The substrate, catalyst, conditions of the reaction and results are set forth in Table 15.
0 - 4.9% In a series of runs, HMPA was separately reacted with benzylamine, urea and formamide, in each case in the presence of a catalyst. The substrate, catalyst, conditions of the reaction and results are set forth in Table 15.
0.7 - 5.0% In a series of runs, HMPA was separately reacted with benzylamine, urea and formamide, in each case in the presence of a catalyst. The substrate, catalyst, conditions of the reaction and results are set forth in Table 15.
0% In a series of runs, HMPA was separately reacted with benzylamine, urea and formamide, in each case in the presence of a catalyst. The substrate, catalyst, conditions of the reaction and results are set forth in Table 15.
0% In a series of runs, HMPA was separately reacted with benzylamine, urea and formamide, in each case in the presence of a catalyst. The substrate, catalyst, conditions of the reaction and results are set forth in Table 15.

  • 47
  • [ 1066-51-9 ]
  • [ 6000-59-5 ]
  • [ 84767-96-4 ]
YieldReaction ConditionsOperation in experiment
In formic acid; EXAMPLE 22 <strong>[1066-51-9]Aminomethylphosphonic acid</strong> (3.12 g, 0.028 mol) was dissolved in 30 ml of stirred 98% formic acid maintained at 80 C. with an oil bath. Glyoxylic acid hydrate (5.60 g, 0.061 mol) was added to the solution in several portions, resulting in vigorous gas evolution. After one hour, the reaction flask was removed from the oil bath and the solvent removed on a rotary evaporator to afford crude N-formyl-N-phosphonomethylglycine as a viscous yellow oil. 1 H NMR (D2 O): delta 8.3(s), 8.15(s), 4.4(s), 4.3(s), 3.79 (d, J=12 Hz), 3.75 (d, J=10 Hz). 3 1 p NMR (D2 O): delta 17.0 (t, J=12 Hz), 16.1 (t, J=10 Hz)
  • 48
  • [ 1066-51-9 ]
  • [ 6000-59-5 ]
  • [ 1071-83-6 ]
YieldReaction ConditionsOperation in experiment
96% EXAMPLE 12 <strong>[1066-51-9]Aminomethylphosphonic acid</strong> and glyoxylic acid hydrate were reacted under catalytic hydrogenation conditions in the manner described in Example 2, except prior to introduction of hydrogen, the pH was adjusted to 8.0. A 96% yield of glyphosate was obtained.
In water; EXAMPLE 25 <strong>[1066-51-9]Aminomethylphosphonic acid</strong> (5.50 g, 0.05 mol) was dissolved in 50 ml of water maintained at 95-100 C. Glyoxylic acid hydrate (9.70 g, 0.105 mol) was added in one portion. After 8 hours of reaction time, the water was removed on a rotary evaporator to afford a brown semisolid. Trituration of this semisolid with a small amount of water followed by filtration afforded 6.43 grams of glyphosate as a crude white solid. An additional 1.60 grams of glyphosate was recovered by chromatography of the mother liquor as described in Example 22.
  • 49
  • [ 1066-51-9 ]
  • [ 109745-70-2 ]
  • [ 1071-83-6 ]
YieldReaction ConditionsOperation in experiment
In hydrogenchloride; EXAMPLE 26 <strong>[1066-51-9]Aminomethylphosphonic acid</strong> (1.9 g, 0.017 mol) and glyoxylic acid methyl ester methyl hemiacetal (4.5 g, 0.038 mol) were heated at reflux in 25 ml of 37% HCl for 20 hours. The solvent was removed on a rotary evaporator to give crude glyphosate as an oily solid. The crude glyphosate was purified by ion exchange chromatography (Dowex 50*8-400) using water as the eluent to yield 2.6 g (89.6%) of glyphosate.
  • 50
  • [ 1066-51-9 ]
  • [ 460-19-5 ]
  • [ 1071-83-6 ]
  • [ 68291-34-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydroxide; In water; Example 1 To a 300 ml-volume four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser were added 50 g of water, 16.7 g (200 mmol) of a 48% aqueous sodium hydroxide solution and 11.1 g (100 mmol) of an aminomethylphosphonic acid and the mixture was stirred. The flask was cooled in an ice water bath, and while keeping the reaction solution at a temperature of 5 C. or lower, 14.3 g (100 mmol) of a 50% glycolonitrile solution was added dropwise over a period of 30 minutes. After completing the dropwise addition, the mixture was stirred at a temperature of 5 C. or lower for 30 minutes. After returning the mixture to room temperature, it was further stirred for 1 hour. Then, 50.7 g (500 mmol) of a 36% aqueous hydrochloric acid solution was added, and the mixture was heat-refluxed for 8 hours with stirring. After completing the reaction, the reaction solution was analyzed by HPLC and was found to contain 89 mmol of N-phosphonomethylglycine. Thus, the reaction yield to N-phosphonomethylglycinonitrile as a raw material was 89%. The reaction solution was concentrated to about one half of its volume, and was allowed to stand all night to crystallize N-phosphonomethylglycine. The N-phosphonomethylglycine was separated by filtration, washed with water and dried to obtain 11.2 g of a purified product.
With hydrogenchloride; sodium hydroxide; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; Example 1 To a 300 ml-volume four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser were added 50 g of water, 16.7 g (200 mmol) of a 48 % aqueous sodium hydroxide solution and 11.1 g (100 mmol) of an aminomethylphosphonic acid and the mixture was stirred. The flask was cooled in ice water, and while keeping the reaction solution at a temperature of 5 iC or lower, 14.3 g (100 mmol) of a 50 % glycolonitrile solution was added dropwise over a period of 30 minutes. After completing the dropwise addition, the mixture was stirred at a temperature of 5 iC or lower for 30 minutes. After returning the mixture to room temperature, it was further stirred for 1 hour. Then, 50.7 g (500 mmol) of a 36 % aqueous hydrochloric acid solution was added, and the mixture was heat-refluxed for 8 hours with stirring. After completing the reaction, the reaction solution was analyzed by HPLC and was found to contain 89 mmol of N-phosphonomethylglycine. Thus, the reaction yield to N-phosphonomethylglycinonitrile as a raw material was 89 %. The reaction solution was concentrated to about one half of its volume, and was allowed to stand all night to crystallize N-phosphonomethylglycine. The N-phosphonomethylglycine was separated by filtration, washed with water and dried to obtain 11.2 g of a purified product.
YieldReaction ConditionsOperation in experiment
41.5% EXAMPLE 10 The disodium salt of [bis(2hydroxyethyl)amino]merhylphosphonic acid (1.6 g, 0.006 mol) was heated in a 11.5% solution of sodium hydroxide (1.5 g, 0.04 mol) in water (10.0 g) at 270 C. for 90 minutes. Work-up gave N-phosphonomethylglycine (0.56 g, 51.4%) and aminomethylphosphonic acid (0.30 g, 41.5%).
18.7% EXAMPLE 9 The procedure of Example 5 was followed in heating the disodium salt of [bis(2hydroxyethyl)amino]methylphosphonic acid trihydrate (2.0 g, 0.007 mol) in a 20% solution of potassium hydroxide (1.5 g, 0.02 mol) and sodium hydroxide (1.1 g, 0.03 mol) in water (10.0 g) at 250 C. for 60 minutes. Product isolation gave N-phosphonomethylglycine (0.57 g, 50.4%) and aminomethylphosphonic acid (0.14 g, 18.7%).
0.71 g (34.1%) EXAMPLE 3 To a 100 mL Monel autoclave were added 2.23 g (12.3 mmol) of 4-morpholinylmethylphosphonic acid 7.88 g (98.5 mmol) of a 50% solution of NaOH, and 10 mL of H2 O to give a slurry. The vessel was flushed with N2, sealed and heated to 250 C. This temperature was maintained for five and one-half hours with little noticeable reaction occurring. The temperature was then raised to 300 C. for three hours. During this period the internal pressure in the vessel rose from 4.5*106 N/M2 to 5.7*106 N/M2. The vessel was cooled to room temperature and the residual pressure was released. The resulting solution was diluted with water and neutralized with 8.1 mL (98.5 mmol) of conc. HCl. The solution was concentrated to dryness. The residue was taken up in conc. HCl and the precipitated NaCl was filtered away. The final filtrate was concentrated and purified by ion exchange chromatography to yield 0.71 g (34.1 %) of N-phosphonomethylglycine and 0.43 g (31.5%) of aminomethylphosphonic acid.
  • 52
  • disodium salt of [bis(2hydroxyethyl)amino]methylphosphonic acid monohydrate [ No CAS ]
  • [ 1066-51-9 ]
  • [ 1071-83-6 ]
YieldReaction ConditionsOperation in experiment
60.0% With potassium hydroxide; EXAMPLE 8 The disodium salt of [bis(2hydroxyethyl)amino]methylphosphonic acid monohydrate (4.0 g, 0.016 mol) was heated with 85% potassium hydroxide (15.0 g, 0.23 mol) at 250 C. for 75 minutes. Product isolation gave N-phosphonomethylglycine (0.31 g, 12.6%) and aminomethylphosphonic acid (1.0 g, 60.0%).
YieldReaction ConditionsOperation in experiment
68.6% EXAMPLE 2 The phosphonylmethylation procedure of Example 1 was repeated to prepare N-acetylaminomethylphosphonic acid. After adding water, and evaporating the reaction mixture to an oil, water (25 ml) was added, and the solution was evaporated again to remove residual formaldehyde and formic acid. To the resulting oil was added concentrated hydrochloric acid (60 ml) and the mixture was heated at reflux for about 16 hours. After cooling, the solution was evaporated to an oil and purified by ion exchange chromatography to yield aminomethylphosphonic acid (3.8 g, 68.6% yield).
  • 54
  • [ 1066-51-9 ]
  • [ 131543-46-9 ]
  • [ 1071-83-6 ]
YieldReaction ConditionsOperation in experiment
7.7 g (45.5%) With sulfur dioxide; In water; EXAMPLE 2 A suspension of 11.1 g (0.1 mol) of aminomethanephosphonic acid and 7.2 g (0.1 mol) of 80% polymeric glyoxal in 40 ml of water is treated with sulfur dioxide and further processed in the manner described in Example 1; yield: 7.7 g (45.5%) of N-phosphonomethylglycine; decomposition: 244 C.
44 g (65%) With sulfur dioxide; In water; EXAMPLE 6 26 g (0.4 mol) Sulfur dioxide gas and 58 g of a 40% aqueous solution of glyoxal (0.4 mol) are simultaneously introduced at a temperature of 40 C. into a suspension of 44.4 g (0.4 mol) of aminomethanephosphonic acid in 160 ml of water. The resulting solution is refluxed for 30 minutes, in course of which an evolution of sulfur dioxide occurs. The solution is then cooled to 5 C.; the formed precipitate is separated, washed with a small amount of ice-water and dried. The resulting yield is 44 g (65%) of N-phosphonomethylglycine; decomposition: >250 C.
50 g (74%) With sulfur dioxide; In water; EXAMPLE 7 26 g (0.4 mol) Sulfur dioxide gas and 58 g of a 40% aqueous solution of glyoxal (0.4 mol) are simultaneously introduced at a temperature of 60 C. into a suspension of 44.4 g (0.4 mol) of aminomethanephosphonic acid in 160 ml of water. The resulting solution is refluxed for 30 minutes, in course of which an evolution of sulfur dioxide occurs. The solution is then cooled to 5 C.; the formed precipitate is separated, washed with a small amount of ice-water and dried. The resulting yield is 50 g (74%) of N-phosphonomethylglycine; decomposition: >250 C.
50 g (74%) With sulfur dioxide; In water; EXAMPLE 8 13 g (0.2 mol) Sulfur dioxide gas and 58 g of a 40% aqueous solution of glyoxal (0.4 mol) are simultaneously introduced at a temperature of 60 C. into a suspension of 44.4 g (0.4 mol) of aminomethanephosphonic acid in 160 ml of water. The resulting solution is refluxed for 30 minutes, in course of which an evolution of sulfur dioxide occurs. The solution is then cooled to 5 C.; the formed precipitate is separated, washed with a small amount of ice-water and dried. The resulting yield is 50 g (74%) of N-phosphonomethylglycine; decomposition: >250 C.
37.6 g (67%) With sodium hydrogen sulphite; In water; EXAMPLE 9 50.5 g of a 40% aqueous solution of glyoxal (0.334 mol) is dropwise added to a solution of 37.1 g (0.334 mol) of aminomethanephosphonic acid and 2.6 g (0.016 mol) of sodium hydrogen sulfite in 150 ml of water at a temperature of 60 C. Stirring of the mixture at the same temperature is continued for 1 hour; the mixture is cooled to 5 C.; the formed precipitate is separated, washed with a small amount of ice-water and dried. The resulting yield is 37.6 g (67%) of N-phosphonomethylglycine; decomposition: >250 C.
10.6 g (62.8%) In water; EXAMPLE 3 Sulfur dioxide gas is introduced, without cooling and with vigorous stirring, into a suspension of 11.1 g (0.1 mol) of aminomethanephosphonic acid and 7.2 g (0.1 mol) of 80% polymeric glyoxal in 40 ml of water until saturation is attained, in the course of which the solution turns yellowish-orange and the temperature rises to 42 C. The solution is subsequently stirred and refluxed, during which time the colour of the solution becomes dark brown. The solution is filtered hot and then cooled to 5 C.; the precipitate is afterwards separated, washed with a small amount of ice-cold water and dried. The resulting yield is 10.6 g (62.8%) of N-phosphonomethylglycine; decomposition: 235 C.

  • 55
  • [ 1066-51-9 ]
  • [ 55101-47-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; EXAMPLE 1 Preparation of Sodium Aminomethanephosphonate STR3 A solution of 4 g (0.1 mole) of sodium hydroxide in 20 ml of distilled water was added to a suspension of 11.11 g (0.1 mole) of aminomethanephosphonic acid in 50 ml of distilled water. Hereupon, salt formation occurred and a clear solution resulted. The solution was then evaporated to dryness in vacuo at a bath temperature of 70 C. The residue which hereupon remained was comminuted and left for a further 30 to 60 minutes in vacuo at 70 C. In this way, 6.65 g (100% of theory) of sodium aminomethanephosphonate were obtained, which decomposed on heating at 320 C. The following compounds were prepared by methods analogous to that in Example 1:
With sodium hydroxide; In water; EXAMPLE 19 Preparation of the Disodium Salt of Aminomethanephosphonic Acid STR21 A solution of 8 g (0.2 mole) of sodium hydroxide in 40 ml of distilled water was added to a suspension of 11.11 g (0.1 mole) of aminomethanephosphonic acid in 50 ml of distilled water. Hereupon, salt formation occurred and a clear solution was formed. The solution was then evaporated to dryness in vacuo at a bath temperature of 70 C. The residue which hereupon remained was comminuted and left in vacuo at 70 C for a further 30 to 60 minutes. 24.15 (98.6% of theory) of the disodium salt of aminomethanephosphonic acid were thus obtained. On heating, the salt behaved as follows: at 84 to 85 C, liquefaction occurred, and from 124 C onwards the water of crystallization boiled off and the residue resolidified and did not melt again up to 355 C.
  • 56
  • [ 1066-51-9 ]
  • ammonium-methyl-phosphonic acid chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; EXAMPLE 20 Preparation of Ammonium-Methyl-Phosphonic Acid Chloride STR22 0.1 mole of hydrochloric acid was added to a suspension of 11.11 g (0.1 mole) of aminomethanephosphonic acid in 50 ml of distilled water. Hereupon salt formation occurred and a clear solution resulted. The solution was then evaporated to dryness in vacuo at a bath temperature of 70 C. The residue which hereupon remained was comminuted and was then left for a further 30 to 60 minutes in vacuo at 79 C. 14.6 g (99% of theory) of ammonium-methyl-phosphonic acid chloride of melting point 170-172 C (decomposition) were thus obtained.
YieldReaction ConditionsOperation in experiment
90% Example 54 Monophospholactate 59: A solution of 34 (2.10 g, 2.48 mmol) in THF (72 mL) and H2O (8 mL) at -15 C. was treated with NaBH4 (0.24 g, 6.20 mmol). The reaction mixture was stirred for 10 min at -15 C. The reaction was quenched with 5% aqueous NaHSO3 and extracted with CH2Cl2 (3*). The combined organic layers were washed with H2O, dried with Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel (5% 2-propanol/CH2Cl2) to give monophospholactate (1.89 g, 90%, GS 278053, 1:1 diastereomeric mixture) as a white solid: 1H NMR (CDCl3) delta7.64 (m, 2H), 7.51(m, 2H), 7.38-7.19 (m, 7H), 6.92 (m, 2H), 5.69 (d, J=4.8 Hz, 1H), 5.15 (m, 2H), 4.76 (s, 2H), 4.54 (d, J=10.5 Hz, 1H), 4.44 (m, 1H), 4.2 (m, 2H), 4.04-3.68 (m, 6H), 3.06-2.62 (m, 7H), 1.8 (m, 3H), 1.62-1.5 (dd, 3H), 1.25 (m, 3H), 0.94 (d, J=6.3 Hz, 3H), 0.87 (d, J=6.3 Hz, 3H); 31P NMR (CDCl3) delta17.4, 15.4.
90% Example M54 Monophospholactate 59: A solution of 34 (2.10 g, 2.48 mmol) in THF (72 mL) and H2O (8 mL) at -15 C. was treated with NaBH4 (0.24 g, 6.20 mmol). The reaction mixture was stirred for 10 min at -15 C. The reaction was quenched with 5% aqueous NaHSO3 and extracted with CH2Cl2 (3*). The combined organic layers were washed with H2O, dried with Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel (5% 2-propanoU/CH2Cl2) to give monophospholactate (1.89 g, 90%, GS 278053, 1:1 diastereomeric mixture) as a white solid: 1H NMR (CDCl3) delta 7.64 (m, 2H), 7.51(m, 2H), 7.38-7.19 (m, 7H), 6.92 (m, 2H), 5.69 (d, J=4.8 Hz, 1H), 5.15 (m, 2H), 4.76 (s, 2H), 4.54 (d, J=10.5 Hz, 1H), 4.44 (m, 1H), 4.2 (m, 2H), 4.04-3.68 (m, 6H), 3.06-2.62 (m, 7H), 1.8 (m, 3H), 1.62-1.5 (dd, 3H), 1.25 (m, 3H), 0.94 (d, J=6.3 Hz, 3H), 0.87 (d, J=6.3 Hz, 3H); 31P NMR (CDCl3) delta 17.4, 15.4.
  • 58
  • [ 213248-53-4 ]
  • [ 1066-51-9 ]
  • [ 1002111-64-9 ]
  • 59
  • [ 1066-51-9 ]
  • [ 2946-39-6 ]
  • [ 1002111-61-6 ]
  • 60
  • [ 53044-29-4 ]
  • [ 1066-51-9 ]
  • 61
  • copper(II) choride dihydrate [ No CAS ]
  • [ 1066-51-9 ]
  • bis(aminomethylphosphonate)copper(II) [ No CAS ]
  • 62
  • cis-Pt((15)NH3)2(OH)2 [ No CAS ]
  • [ 1066-51-9 ]
  • [ 99837-56-6 ]
  • [ 99829-44-4 ]
  • 63
  • cis-Pt((15)NH3)2(OH)2 [ No CAS ]
  • [ 1066-51-9 ]
  • [ 99829-42-2 ]
  • 64
  • cis-diamminediaquaplatinum(II) [ No CAS ]
  • [ 1066-51-9 ]
  • [ 99829-38-6 ]
  • 65
  • cis-diamminediaquaplatinum(II) [ No CAS ]
  • [ 1066-51-9 ]
  • [ 99837-56-6 ]
  • 66
  • [ 10025-99-7 ]
  • [ 1066-51-9 ]
  • [ 99829-41-1 ]
  • 67
  • [ 1066-51-9 ]
  • copper dichloride [ No CAS ]
  • Cu(2+)*H2NCH2PO3(2-)*2H2O=Cu(H2NCH2PO3)*2H2O [ No CAS ]
  • 68
  • [ 1066-51-9 ]
  • copper dichloride [ No CAS ]
  • Cu(2+)*2H3NCH2PO3(1-)=Cu(H3NCH2PO3)2 [ No CAS ]
  • 69
  • [ 1066-51-9 ]
  • copper dichloride [ No CAS ]
  • [ 77338-49-9 ]
  • 70
  • cobalt(II) chloride hexahydrate [ No CAS ]
  • [ 1066-51-9 ]
  • diaquo-bis(aminomethylphosphonate)cobaltate(II) monohydrate [ No CAS ]
  • 71
  • iron(III) perchlorate hydrate [ No CAS ]
  • [ 1066-51-9 ]
  • [ 7732-18-5 ]
  • [ 364042-16-0 ]
  • 72
  • [ 7446-70-0 ]
  • [ 1066-51-9 ]
  • [ 7789-20-0 ]
  • [Al2(D2O)4(OD)2(aminomethylphosphonic acid(-1H))(aminomethylphosphonic acid)](3+) [ No CAS ]
  • 73
  • [ 1066-51-9 ]
  • [ 2923-28-6 ]
  • [Ag6(aminomethylphosphonate)4(CF3SO3)2(H2O)2]n [ No CAS ]
  • 74
  • [ 1066-51-9 ]
  • mercury(II) nitrate [ No CAS ]
  • [Hg2(aminomethylphosphonate)2(H2O)(NO3)]n [ No CAS ]
  • 75
  • [ 1066-51-9 ]
  • cadmium(II) nitrate [ No CAS ]
  • [ 1043413-89-3 ]
  • 76
  • [ 1066-51-9 ]
  • [ 34946-82-2 ]
  • silver nitrate [ No CAS ]
  • [Ag(aminomethylphosphonate)Cu2(NO3)]n [ No CAS ]
  • 77
  • [ 1066-51-9 ]
  • silver nitrate [ No CAS ]
  • [Ag(aminomethylphosphonate)2]NO3 [ No CAS ]
  • [Ag3(aminomethylphosphonate)2(NO3)(H2O)]n [ No CAS ]
  • 78
  • lead(II) nitrate [ No CAS ]
  • [ 1066-51-9 ]
  • [ 1042385-18-1 ]
  • 79
  • [ 1066-51-9 ]
  • [ 7646-85-7 ]
  • [ 1043413-88-2 ]
  • 80
  • [ 1066-51-9 ]
  • N-{2-[(3-[5-oxido-4-(phenylsulphonyl)-1,2,5-oxadiazol-3-yl]-oxy}-propionyl)-oxy]-5-norbornene-2,3-dicarboximide [ No CAS ]
  • [ 1134634-19-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20℃; for 72h; EXAMPLE 7(2S,3aS,7aS)-1-[(2S)-2-[(1S)-1-(Ethoxycarbonyl)-butyl]-amino}-propionyl]-octahydro-1H-indole-2-carboxylic Acid-[(3-[5-oxido-4-(phenylsulphonyl)-1,2,5-oxadiazol-3-yl]-oxy}-propionyl)-amino]-methyl}-phosphonic Acid (1:1)Step A[(3-[5-Oxido-4-(phenylsulphonyl)-1,2,5-oxadiazol-3-yl]-oxy}-propionyl)-amino]-methyl}-phosphonic Acid (Compound B9); A solution prepared from the compound obtained in Step A of Example 6 (2.14 g-4.5 mmol), aminomethylphosphonic acid (0.7 g-6 mmol) and NaHCO3 (1 g-12 mmol) in 50 ml of dioxane and 50 ml of water is stirred for 72 hours at ambient temperature. The solvents are then evaporated off to dryness and the residue is taken up in 100 ml of water and 100 ml of ethyl acetate and stirred for 1 hour. After decanting, the aqueous phase is purified on a column of DOWEX 50WX8 cation exchange resin. The residue obtained following evaporation of the water is crystallised in acetonitrile, filtered off with suction and then dried in vacuo to yield the expected product.Melting point: 171-172 C.
  • 81
  • [ 10213-10-2 ]
  • [ 155306-81-3 ]
  • [ 17620-46-1 ]
  • [ 1066-51-9 ]
  • hydrous silica gel [ No CAS ]
  • methyl tri-n-octyl ammonium hydrogen sulfate [ No CAS ]
  • [ 958885-37-5 ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; In a 50 ml three-necked flask equipped with a reflux condenser, thermometer, stirrer, dropping funnel and oil bath there were charged 100.0 g of N-allyl-4-cyclohexene-1,2-dicarboximide, 2.44 g of methyltrioctylammonium hydrogensulfate, 3.45 g of sodium tungstate dihydrate and 0.58 g of aminomethylphosphonic acid. The mixture was heated using an oil bath kept at 90 C., and after adding 80 ml of 30% hydrogen peroxide water dropwise over a period of 180 minutes through a dropping funnel, the mixture was aged for 4 hours. After cooling with an ice bath and removing the excess hydrogen peroxide with 300 ml of saturated aqueous sodium thiosulfate, extraction was performed twice with 200 ml of ethyl acetate. The obtained ethyl acetate solution was dried overnight over anhydrous sodium sulfate, and a rotary evaporator was used to remove the ethyl acetate solvent, after which purification was performed with a chromatography column packed with 25% hydrous silica gel to obtain 78.9 g of 4,5-epoxy-N-allylcyclohexane-1,2-dicarboximide.
  • 82
  • [ 1066-51-9 ]
  • [ 119197-24-9 ]
  • C11H10ClF3NO3P [ No CAS ]
  • 84
  • [ 1066-51-9 ]
  • [ 149508-60-1 ]
  • C13H15F3NO3PS [ No CAS ]
  • 86
  • [ 500-22-1 ]
  • [ 1066-51-9 ]
  • [ 261958-77-4 ]
  • 87
  • [ 98-01-1 ]
  • [ 1066-51-9 ]
  • C6H8NO4P [ No CAS ]
  • 88
  • [ 1066-51-9 ]
  • [ 104-88-1 ]
  • C8H9ClNO3P [ No CAS ]
  • 89
  • [ 1066-51-9 ]
  • [ 123-11-5 ]
  • C9H12NO4P [ No CAS ]
  • 90
  • [ 1066-51-9 ]
  • [ 119-67-5 ]
  • C9H10NO5P [ No CAS ]
  • 91
  • [ 120060-75-5 ]
  • [ 108-24-7 ]
  • [ 1066-51-9 ]
  • [ 6419-19-8 ]
  • [ 17261-34-6 ]
  • 92
  • [ 120060-75-5 ]
  • [ 108-24-7 ]
  • [ 1066-51-9 ]
  • [ 17261-34-6 ]
  • 93
  • [ 1066-51-9 ]
  • C10H8N2O5S [ No CAS ]
  • C7H9N2O5PS [ No CAS ]
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