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[ CAS No. 96-26-4 ]

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Chemical Structure| 96-26-4
Chemical Structure| 96-26-4
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Product Details of [ 96-26-4 ]

CAS No. :96-26-4 MDL No. :MFCD00004670
Formula : C3H6O3 Boiling Point : 213.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :90.08 g/mol Pubchem ID :670
Synonyms :

Safety of [ 96-26-4 ]

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
GHS Pictogram:

Application In Synthesis of [ 96-26-4 ]

  • Upstream synthesis route of [ 96-26-4 ]
  • Downstream synthetic route of [ 96-26-4 ]

[ 96-26-4 ] Synthesis Path-Upstream   1~38

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Reference: [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1929, vol. 183, p. 71
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Reference: [1] Journal of the American Society for Mass Spectrometry, 2016, vol. 27, # 5, p. 897 - 907
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Patent: US6268363, 2001, B1,
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Reference: [1] Green Chemistry, 2017, vol. 19, # 15, p. 3515 - 3519
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YieldReaction ConditionsOperation in experiment
54%
Stage #1: With barium(II) chloride In water at 100℃; for 0.166667 h;
Stage #2: With sodium acetate; DL-cysteine hydrochloride In water at 20℃; for 24 h;
To a suspension of tetraaminopyrimidine sulfate (7.14 g, 30 mmol) in water is added barium chloride (7.32 g, 30 mmol) at once. The mixture is heated at 100 0C for 10 min and cooled to RT. The solid barium sulfate is removed by filtration. The filtrate is added to a solution of 450 mL of 4 M aqueous sodium acetate solution containing dihydroxyacetone (8 g, 90 mmol) and cysteine hydrochloride monohydrate (3.63 g, 30 mmol) in a 1 liter 3-neck round bottom flask attached with a mechanical stirrer and stirred for 24 h at RT open to air. The precipitated yellow solid is filtered, washed with water, and ethanol and dried overnight in a heated vacuum oven to give 3.4 g (66percent) of product. This product is further purified as per the following procedure. The yellow solid is dissolved in 10percent acetic acid with aid of few drops of cone. HCl at 75 0C. The hot solution is treated with activated charcoal and filtered. The filtrate is neutralized with cone. NH4OH. The bright yellow solid is collected, washed with water, water-ethanol and finally ethanol and dried overnight in a heated vacuum oven to provide 2.8 g of the title compound (54percent).
Reference: [1] Patent: WO2010/110907, 2010, A1, . Location in patent: Page/Page column 48-49
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 10, p. 1463 - 1468
[2] Patent: CN102977090, 2016, B, . Location in patent: Paragraph 0087; 0088
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Reference: [1] Patent: US2006/205729, 2006, A1, . Location in patent: Page/Page column 11
[2] Patent: US2005/209239, 2005, A1, . Location in patent: Page/Page column 16
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YieldReaction ConditionsOperation in experiment
72 % With selenium(IV) oxide; sodium acetate In water 1.
2,4-DIAMINO-6-HYDROXYMETHYLPTERIDINE SPC2
A solution of 6.4 grams of barium chloride in a minimum amount of hot water was added with stirring at a temperature of 70°-80° C to a suspension of 7.6 grams of 2,4,5,6-tetraaminopyrimidine sulphate in 104 ml water.
The resulting suspension was stirred for 30 minutes and the formed barium sulphate was removed by filtration and washed on the funnel with 26 ml water at a temperature of 70° C.
The solution containing the 2,4,5,6-tetraaminopyrimidine dihydrochloride is diluted with water to a final volume of 400 ml.
A solution of 128 grams of sodium acetate, 136 grams of bisulphite addition product of 1,3-dihydroxyacetone (free of methyl glyoxal) and 46 grams of cysteine hydrochloride in 390 ml water was prepared at room temperature in a 2 liter three-necked flask fitted with a stirrer, an air-bubbling system and a dropping funnel.
To this solution, the 400 ml of the previously prepared solution of 2,4,5,6-tetraaminopyrimidine dihydrochloride were added with energic stirring and air-bubbling.
A solution of 8 g of selenium dioxide dissolved in the minimum amount of water was made.
Half of this solution was added to the reaction mixture immediately after the addition of the tetraaminopyrimidine solution and the other half 4-7 hours later.
The reaction was allowed to proceed for 24 hours at room temperature.
The reaction can be carried out in a similar manner in a range of temperatures from 20° to 100° C, but the yield is lower.
After the end of the reaction, the solution is kept 1 hour at 4° C.
The precipitate was filtered off, washed on the funnel with cold alcohol, alcohol:ethyl ether (1:1) and ethyl ether, then dried under vacuum for 24 hours at 50°.
The yield is 3,8 g (72 percent) of 2,4-diamino-6-hydroxymethylpteridine.
Reference: [1] Patent: US3989703, 1976, A,
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YieldReaction ConditionsOperation in experiment
71% With ammonium hydroxide; hydrogen In methanol; water at 65℃; for 6 h; Autoclave In an autoclave, a mixture of Raney nickel (4 g, wet) and ammonium hydroxide solution (257 g, 28percent NH3 in water, 4.2 mol) was heated to 65° C. under 250 psi of hydrogen atmosphere. A solution of 1,3-dihydroxyacetone (38 g, 0.42 mol) in methanol (76 ml) was pumped into the autoclave over a period of 3 h. After the addition was complete, the reaction mixture was maintained at 65° C. and 250 psi hydrogen pressure for additional 3 h. The autoclave was then cooled to ambient temperature and depressurized. The resulting reaction mixture was filtered to remove the catalyst. Ammonia and most of the water were removed by distillation under reduced pressure. GC analysis of the crude product showed a mixture of 91percent serinol (2-amino-1,3-propanediol) and 7percent bis-adduct (2,2′-iminobis-1,3-propanediol). (0025) An aqueous solution of the crude product mixture was loaded to a column of Amberlyst® 15 and eluted with water until neutral pH. GC analysis of the water eluate showed mainly the bis-adduct and other unidentified impurities. The column was then eluted with 300 ml of 4M ammonium hydroxide solution to recover the serinol. The eluate was then stripped under vacuum to remove ammonia and water. The residue was triturated with a 1:1 mixture of 2-butanol and 2-methyltetrahydrofuran to yield crystalline serinol (27 g, 71percent yield). Assay by GC: 97percent; Assay by titration: 101percent
61% With ammonia; hydrogen In methanol; water at 65℃; for 5 h; In an autoclave, ammonia gas (13 g, 0.77 mol) was charged to a suspension of Raney nickel (4 g, wet) in methanol (100 ml) and then heated to 65° C. under 250 psi of hydrogen atmosphere. A solution of 1,3-dihydroxyacetone (58percent solution in water, 200 g, 1.29 mol) was pumped into the autoclave over a period of 2 h. After the addition was complete, the reaction mixture was continued to hydrogenate at 65° C. temperature and 250 psi hydrogen pressure for an additional 3 h. The autoclave was cooled to ambient temperature and depressurized. The reaction mixture was filtered to remove the catalyst and evaporated under vacuum to remove ammonia and most of the water. The crude product was shown to contain 2.4percent serinol and 90percent 2,2′-iminobis-1,3-propanediol by GC analysis. (0029) An aqueous solution of the crude product was loaded to a column of Amberlyst® 15 and eluted with water until neutral pH. GC analysis of the water eluate showed complete removal of serinol (FIG. 5). The water eluate was then evaporated under vacuum, the residue was dissolved in 1:1 mixture of 2-butanol and tetrahydrofuran, treated with activated carbon, and concentrated to yield the bis-adduct 2,2′-iminobis-1,3-propanediol as a viscous oil (65 g, 61percent). Assay by GC: 99percent
Reference: [1] Patent: US8653306, 2014, B1, . Location in patent: Page/Page column 3-4
[2] Patent: US8653306, 2014, B1, . Location in patent: Page/Page column 4-5
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Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 120, p. 141 - 150
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YieldReaction ConditionsOperation in experiment
81% With Cu/Al2O3; dihydrogen peroxide In water at 25℃; for 24 h; Green chemistry General procedure: The catalyst A 25 mg prepared in Example 1 was weighed, added to a 38 mL reaction tube with magnetic stirring, and then 465 mg (5 mmol) of aniline, 90 mg (1 mmol) of 1,3-dihydroxyacetone, 0.5 mL (6 mmol) 35percent hydrogen peroxide and 5 mL chloroform. Thereafter, the temperature was raised to 50 ° C using an electric heating furnace and maintained for 12 hours. Then, the reaction tube was cooled to room temperature by water cooling, centrifuged at 8000 rpm for 5 minutes using a centrifuge (Shanghai Anting Scientific Instrument Factory), and separated to recover Catalyst A from the reaction mixture. Using N-formylated aniline standard product as a comparison, qualitative and quantitative analysis was performed using HP 6890/5973 GC-MS gas chromatography mass spectrometer and Agilent 7890A (30m×0.25mm×0.33μm capillary column, hydrogen flame ionization detector). A well-known method in the art, such as an industrial rectification process, obtains the target product N-formylated aniline, and the yield results are shown in Table 1 below.
Reference: [1] Patent: CN108658715, 2018, A, . Location in patent: Paragraph 0040; 0048; 0049
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Reference: [1] ChemSusChem, 2013, vol. 6, # 8, p. 1352 - 1356
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Reference: [1] Chemical Communications, 2005, # 21, p. 2716 - 2718
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Reference: [1] ChemCatChem, 2015, vol. 7, # 7, p. 1152 - 1160
[2] ChemSusChem, 2013, vol. 6, # 8, p. 1352 - 1356
[3] Chemical Communications, 2005, # 21, p. 2716 - 2718
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YieldReaction ConditionsOperation in experiment
26.7 %Spectr. With molybdenum(VI) oxide In water at 100℃; for 4 h; FIG. 8 shows 1H NMR spectra of D-fructose standard solution and of the fructose-containing fraction isolated after reaction of D-fructose with MoO3 in water at 100° C. for 4 h. Sorbose is present in the collected fraction.
Reference: [1] Patent: US2017/15614, 2017, A1, . Location in patent: Page/Page column 2; 13-14
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Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 9, p. 2623 - 2632
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Reference: [1] Patent: US2011/137085, 2011, A1, . Location in patent: Page/Page column 9-10
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YieldReaction ConditionsOperation in experiment
87.5% With hydrogenchloride; ammonium cerium (IV) nitrate; sodium ethanolate In ethanol; acetonitrile at 60℃; for 8 h; A mixture of acetonitrile and ethanol in a volume ratio of 2: 1 was added to the reactor,100 mmol of 1,3-dihydroxyacetone and 200 mmol of formaldehyde were dissolved in an organic solvent,100 mmol of cerium ammonium nitrate was added,Under normal pressure 60 conditions,Adding sodium ethoxide to adjust the pH to 10,15 mmol of catalyst was added,Stirring reaction 8h, obtained 4-hydroxymethyl imidazole,After completion of the reaction,Dropping concentrated HCl,Adjust pH = 2,filter,The filtered solid,Washed with saturated brine,Recrystallization from ethanol,Dried in vacuo to give the product 4-hydroxymethylimidazole hydrochloride.The purity of the prepared 4-hydroxymethylimidazolidine hydrochloride was 98.2percentThe yield was 87.5percent.
Reference: [1] Patent: CN106349165, 2017, A, . Location in patent: Paragraph 0016-0030
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Reference: [1] Synthesis, 1983, # 7, p. 576
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YieldReaction ConditionsOperation in experiment
85% With hydrogenchloride; sodium cyanoborohydride In N,N-dimethyl-formamide at 60℃; for 24 h; III (0.2 g, 0.001 mmol) was added to DMF (8 mL), stirred and dissolved, followed by the addition of 1,3-dihydroxyacetone (0.3 g, 0.03 mmol), 2N HCl (0.15 mL) and NaBH3CN (0.22 g, 0.004 mol) at 60 °C for 24 h cooled to room temperature, add water (3mL), adjusted to pH=4.0 with 2 Ν HCl, stirred for 30min, 1N NaOH was added to adjust PH = 7.0, the solvent was distilled off under reduced pressure through the UBK resin, followed by elution with water, 2N ammonia, and the eluate was collected and concentrated. After passing through CG50, water: ethanol (6: 4) was eluted and the eluate was collected, and then decolorized by Dowex1 x 2 to give 0.24 g of white powder voglibose, 85percent.
82% With hydrogenchloride; water; sodium cyanoborohydride In water; N,N-dimethyl-formamide at 70℃; for 16 h; To a solution of 6 (483mg, 2.5mmol) in DMF (30mL), 1,3-dihydroxyacetone (900mg, 10.0mmol) and 2.0M hydrochloric acid (0.50mL) and NaBH3CN (628mg, 10.0mmol) were added successively. The mixture was heated for 16h at 70°C with stirring and cooled to rt and then evaporated. The residual product was dissolved in H2O (25mL) and adjusted to pH=4.0 with 2.0M hydrochloric acid under ice bath. The mixture was stirred at rt and adjusted to pH=4.5 with 1.0M NaOH and then concentrated. The residual product was eluted from a column of Amberlite CG-50 (NH4+) resin (100mL) with deionized water (100mL) and 1.0M aqueous ammonia (200mL) successively to give white product (550mg, 82percent). (0031) Amorphous white solid, mp 161.5–162.1°C (lit.11 mp 162–163°C). [α]D25 +25.9(c 1.02, H2O) (lit.11 [α]D25 +26.2(c 1.00, H2O)). FT-IR (Neat): νmax=3453, 3295, 2928, 1417, 1115, 1086, 1055, 1031, 992, 848cm−1; 1H NMR (400MHz, D2O): δ=3.77 (t, J=9.7Hz, 1H), 3.66 (dd, J=8.4, 3.8Hz, 1H), 3.63 (dd, J=6.9, 4.8Hz, 2H), 3.58 (dd, J=12.1, 3.9Hz, 2H), 3.52 (dd, J=11.5, 6.7Hz, 1H), 3.46 (d, J=11.3Hz, 1H, ABq), 3.42 (d, J=11.3Hz, 1H, ABq), 3.35 (d, J=9.5Hz, 1H), 3.32 (d, J=3.5Hz, 1H) ppm. 13C NMR (101MHz, D2O): δ=76.67, 74.50, 73.55, 72.47, 65.60, 62.65, 58.93, 56.93, 54.87, 29.75ppm.
Reference: [1] Patent: CN107129474, 2017, A, . Location in patent: Paragraph 0060; 0068; 0069
[2] Tetrahedron, 2013, vol. 69, # 34, p. 7031 - 7037
[3] Journal of Medicinal Chemistry, 1986, vol. 29, # 6, p. 1038 - 1046
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Reference: [1] Chemische Berichte, 1980, vol. 113, # 4, p. 1514 - 1523
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Reference: [1] Journal of Medicinal Chemistry, 1985, vol. 28, # 5, p. 660 - 667
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