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[ CAS No. 116-09-6 ] {[proInfo.proName]}

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Chemical Structure| 116-09-6
Chemical Structure| 116-09-6
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Product Details of [ 116-09-6 ]

CAS No. :116-09-6 MDL No. :MFCD00004669
Formula : C3H6O2 Boiling Point : -
Linear Structure Formula :CH3C(O)CH2OH InChI Key :XLSMFKSTNGKWQX-UHFFFAOYSA-N
M.W : 74.08 Pubchem ID :8299
Synonyms :

Safety of [ 116-09-6 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P403+P235 UN#:1224
Hazard Statements:H225 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 116-09-6 ]

* 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 [ 116-09-6 ]

[ 116-09-6 ] Synthesis Path-Downstream   1~14

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  • 5
  • [ 116-09-6 ]
  • [ 109-77-3 ]
  • [ 5117-87-3 ]
YieldReaction ConditionsOperation in experiment
30% With triethylamine; In methanol; at 0 - 20℃; To a mixture of malonontrile (0.96 g, 14.6 mmol), acetol (1.08 g, 14.6 mmol) in methanol (10 mL) at 0 C. was added, dropwise, triethylamine (2.0 mL). The reaction mixture was stirred at room temperature overnight. After removal of solvent under reduced pressure the crude solid was washed with cold isopropanol to give product as white powder (0.54 g, 30%). HPLC/MS: (M+H)+ 123.3 m/z. Retention time (LC-MS)=1.81 min. 1H NMR (CD3OD): 6.58(s, 1H,); 1.95 (s, 3H).
With triethylamine; In methanol; at 20℃; To a solution of hydroxyacetone (1.0 g, 13.5 mmol) in 45 mL MeOH was added a solution of malonitrile (0.9 g, 13.5 mmol) in TEA (1.36 g, 13.5 mmol) and 10 mL MeOH. After stirring overnight at room temperature, the solvents were removed by rotary evaporation to give Q-1 as a brown semi-solid. Data for Q-1: 1H NMR (500 MHz, CDCl3) delta 2.01 (s, 3H), 4.71 (br s, 2H), 6.57 (s, 1H).
With triethylamine; In methanol; at 20℃; for 12h; Compound 3 was obtained as per reported method by stirring 1 with 2 at room temperature in the presence of triethylamine and was used without purification for further steps
With methanol; triethylamine; at 20℃; Intermediate compound 12 (Scheme 1B) was prepared by a 2-step procedure reported by Taylor et al.?2 Acetol 10 was condensed with malononitrile in the presence of triethylamine in methanol to afford 2-amino-3-cyano-4-methylfuran (compound 11) which was condensed with guanidine hydrochloride in presence of sodium methoxide to give intermediate (compound 12) in 44% yield. The synthesis of target compounds 2-9, outlined in Scheme 1B, involved oxidative thiolation of the common intermediate 2,4-diamino-5 -methyl-pyrrolo [2,3-d]pyrimidine (compound 12) with appropriately substituted thiols. Compounds 2-5 were synthesized from compound 12 with slight modification of the oxidative thiolation previously reported by Gangjee et al.?3 This procedure involved reacting compound l2with appropriately substituted thiols and iodine in a 2:1 mixture of ethanol and water at reflux to give compounds 2-5. Compounds 6-9 were synthesized by methylation of the pyrrole nitrogen using sodium hydride and iodomethane.
With triethylamine; at 20℃; for 12h; To a solution ofacetol (10 g, 135 mmol) in methanol (200 mL) at room temperaturewas added malononitrile (8.9 g, 135 mmol) and triethylamine(13.7 g, 135 mmol). The resulting mixture was stirred at room temperatureovernight. The reaction mixture was then stripped of solventin vacuo. The residue was washed with hexane-ethyl acetate(5:1) (250 mL 5). The resulting hexane-ethyl acetate solution ofthe product was collected. After the evaporation of solvent underreduced pressure, 13 g (79%) of the crude product was obtainedas an orange powder and was used directly in the next reactionwithout analysis.

  • 6
  • [ 114046-25-2 ]
  • [ 116-09-6 ]
  • 3-hydroxy-4-(4-methoxyphenylamino)-4-(4-cyanophenyl)butan-2-one [ No CAS ]
  • (3S,4R)-3-hydroxy-4-(4-methoxyphenylamino)-4-(4-cyanophenyl)-butan-2-one [ No CAS ]
  • 7
  • [ 513-86-0 ]
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YieldReaction ConditionsOperation in experiment
8percent Mo on gamma-alumina containing 1-2percent dispersed silica; at 145℃; for 2h;Conversion of starting material; [0032] A feed containing 990 ppm hydroacetone (HA or acetol), 520 ppm of 1-hydroxy-2-butanone (1HB), and 490 ppm of 3-hydroxy-2-butanone (3HB or acetoin), was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing approximately 8 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones averaged 98, 98, and 100 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. Approximately 6 percent of the HA was converted to 2-methyl benzofuran, 3 percent of the 1-HB was converted to 2-ethyl benzofuran, and 3 percent of 3-HB was converted to 1,3-dimethyl benzofuran.
gamma-alumina Containing 1-2percent Dispersed Silica; at 145℃; for 2h;Conversion of starting material; [0034] A feed containing 990 ppm HA, 520 ppm of 1HB, and 490 ppm of 3HB was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing no molybdenum and which had been previously activated and dried. Conversion of hydroxyketones were 18, 15, and 8 percent for HA, 1HB, and 3HB, respectively. The corresponding benzofuran selectivities were approximately 2, 0.5, and 2 percent.
4percent Mo on gamma-alumina Containing 1-2percent Dispersed Silica; at 145℃; for 2h;Conversion of starting material; [0033] A feed containing 990 ppm hydroacetone (HA or acetol), 520 ppm of 1-hydroxy-2-butanone (1HB), and 490 ppm 3-hydroxy-2-butanone (3HB or acetoin), was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing approximately 4 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones averaged 84, 87 and 98 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 6, 3, and 2.5 percent.
at 145℃; for 2h;Conversion of starting material; [0035] A feed containing 990 ppm HA, 520 ppm of 1HB and 490 ppm of 3HB was prepared from pure phenol and heated for 2 hours at 145° C. without addition of a catalyst. Conversion of hydroxyketones averaged 5, 5, and 7 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 3, 0.1, and 3 percent.
at 145℃; for 2h;Conversion of starting material; A feed containing 990 ppm hydroacetone (HA or acetol), 520 ppm of 1-hydroxy-2-butanone (1HB), and 490 ppm of 3- HYDROXY-2-BUTANONE (3HB or acetoin), was prepared from pure phenol and contacted for 2 hours at 145 C with an alumina catalyst containing approximately 8 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones averaged 98,98, and 100 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. Approximately 6 percent of the HA was converted to 2-methyl benzofuran, 3 percent of the 1-HB was converted to 2-ethyl benzofuran, and 3 percent of 3-HB was converted to 1,3- dimethyl benzofuran.
aluminum oxide; at 145℃; for 2h;Conversion of starting material; A feed containing 990 ppm HA, 520 ppm of 1HB, and 490 ppm of 3HB was prepared from pure phenol and contacted for 2 hours at 145 C with an alumina catalyst containing no molybdenum and which had been previously activated and dried. Conversion of hydroxyketones were 18,15, and 8 percent for HA, 1HB, and 3HB, respectively. The corresponding benzofuran selectivities were approximately 2,0. 5, and 2 percent.
at 145℃; for 2h;Conversion of starting material; A feed containing 990 ppm hydroacetone (HA or acetol), 520 ppm of 1-hydroxy-2-butanone (1HB), and 490 ppm 3-hydroxy- 2-butanone (3HB or acetoin), was prepared from pure phenol and contacted for 2 hours at 145°C with an alumina catalyst containing approximately 4 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones averaged 84,87 and 98 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 6,3, and 2.5 percent.
at 145℃; for 2h;Conversion of starting material; A feed containing 990 ppm HA, 520 ppm of 1HB and 490 ppm of 3HB was prepared from pure phenol and heated for 2 hours at 145 C without addition of a catalyst. Conversion of hydroxyketones averaged 5,5, and 7 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 3,0. 1, and 3 percent.

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  • [ 3131-63-3 ]
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YieldReaction ConditionsOperation in experiment
amberlyst 15 (TM) cation exchange resin; at 80℃; for 2h;Conversion of starting material; [0046] A feed containing 1450 ppm hydroxyacetone (HA or acetol), 520 ppm of 1-hydroxy-2-butanone (1HB), and 540 ppm of 3-hydroxy-2-butanone (3HB or acetoin) was prepared from pure phenol. The feed was stirred for 2 hours at 80° C. with Amberlyst 15 (TM) cation exchange resin beads which had previously been water rinsed and vacuum dried. Conversion of the hydroxyketones was 94 percent for HA, 74 percent for 1HB, and 80 percent for 3HB. Approximately 6 percent of the HA was converted to 2-MBF (2-methyl benzofuran), 3 percent of the 1HB was converted to EBF (2-ethyl benzofuran), and 24 percent of the 3HB was converted to DMBF (1,3 dimethyl benzofuran).
Y-zeolite catalyst; at 150℃; for 2h;Conversion of starting material; [0047] A feed containing 1000 ppm HA, 5300 ppm of 1HB, and 1050 ppm of 3HB was prepared from pure phenol and contacted for 2 hours at 150° C. with a Y-zeolite catalyst which had been previously activated and dried. The percent conversions of hydroxyketones were 93 for HA, 84 for 1HB, and 89 for 3HB. The corresponding benzofuran selectives were 33, 18 and 68 percent.
alumina catalyst containing approximately 4 percent molybdenum; at 145℃; for 2h;Conversion of starting material; [0049] A feed containing 990 ppm HA, 520 ppm of 1HB, and 490 ppm 3HB was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing approximately 4 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones were 84, 87 and 98 percent for HA, 1HB, and 3HB. The corresponding benzofuran selectivities averaged approximately 6, 3, and 2.5 percent.
alumina catalyst containing approximately 8 percent molybdenum; at 145℃; for 2h;Conversion of starting material; [0048] A feed containing 990 ppm HA, 520 ppm of 1HB, and 490 ppm of 3HB was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing approximately 8 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones averaged 98, 98, and 100 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 6, 3, and 3 percent
[0050] A feed containing 990 ppm HA, 520 ppm of 1HB, and 490 ppm of 3HB was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing no molybdenum and which had been previously activated and dried. Conversion of hydroxyketones averaged 18, 15, and 8 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities were approximately 2, 0.5, and 2 percent.
Conversion of starting material; [0051] A feed containing 990 ppm HA, 520 ppm of 1HB and 490 ppm of 3HB was prepared from pure phenol and heated for 2 hours at 145° C. without addition of a catalyst. Conversion of hydroxyketones averaged 5, 5, and 7 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 3, 0.1, and 3 percent.

  • 9
  • [ 116-09-6 ]
  • [ 122-51-0 ]
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YieldReaction ConditionsOperation in experiment
With sodium acetate; acetic anhydride; acetic acid; triethylamine; In toluene; EXAMPLE 1 This Example illustrates the preparation of a number of 4-amino-5-methyl-furo [2,3-d] pyrimidines having the structural formula: STR5 The supposed 2-amino-3-cyano-4-methylfuran (m.p. 156-8) described by Gewalt (Chem. Ber., 1966, 99, 1002) has been shown by McKee (J. Org. Chem., 1973, 38, 612) to be the Diels-Alder dimer, 2,4-diamino-3,5-dicyano-3a,6-dimethyl-3a,4,7,7a-tetrahydro-endo-4,7-epoxybenzofuran. A mixture of malononitrile (17.9 g), triethylamine (14.6 ml) and toluene (140 ml) was stirred at room temperature for ten minutes, then treated with acetol (13.2 g). Following an exothermic reaction, the mixture was refluxed for ten minutes, cooled and the toluene layer decanted. The oily residue was extracted with toluene and the total extracts washed with water, dried and evaporated to give a white solid (7.24 g; m.p. 114). Recrystallisation from petroleum (b.p. 80-100) gave material m.p. 117, shown to be the unstable monomeric 2-amino-3-cyano-4-methylfuran by analysis and by n.m.r. spectrometry [CDCl3:tau3.43 (1H, singlet); 5.0 (2H, broad); 8.03 (3H, singlet]. A mixture of this freshly prepared material (3.12 g), triethylorthoformate (3.0 ml) and acetic anhydride (0.5 ml) was heated for two and a half hours at 130, then treated with a mixture of an appropriate primary amine (0.028 mole, approximately 10% excess), acetic acid (5 ml) and anhydrous sodium acetate (3.1 g). The mixture was heated at 130 for a further three hours, cooled, poured into water and extracted with ether. The extracts were washed with water, dried and evaporated and the residue distilled in a bulb-tube apparatus (pressure, ~0.02 mm; bath temperature 130-170) to give products as shown in Table II below. In most cases, the distillate solidified and was recrystallized from e.g. petroleum to give material with the melting-point shown. Compound No. 9 was made similarly.
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  • 11
  • [ 56-81-5 ]
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  • [ 39986-37-3 ]
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  • 3,5-dihydroxycyclohexanamine [ No CAS ]
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  • [ 64-19-7 ]
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  • [ 116-09-6 ]
  • [ 107-02-8 ]
YieldReaction ConditionsOperation in experiment
With H-ZSM5; In water; at 340℃; under 760.051 Torr; for 6.0h;Inert atmosphere; General procedure: For each experiment, 5 g of catalyst was charged into the reactorequipped with a catalyst support (stainless steel) and a fritted disk(quartz). Dimensions are reported in previously published work [5].Experiments were conducted at atmospheric pressure and 340 C in continuous operation with nitrogen as carrier gas and a con-stant supply of a 35 wt% glycerol aqueous solution. Details on massflow controllers, furnaces and pumps are described elsewhere [26].Sampling took place at hourly intervals, and product analyses wereoff-line. Liquid samples were collected using a syringe. Methanol was used as solvent for GC-MS analyses, performed in an Agilent6890 series GC with an Agilent 5973N detector and a Restek Rtx-200 MS column: 30 m × 0.25 mm ID × 0.5 m. Helium was used ascarrier gas with a sample injection (1 l) split ratio of 10:1 appliedfor all analyses. Injector and detector were maintained at 220Cand 285C respectively, while the oven initial temperature (45C)was held for 5 min, increasing to 115C in 15 min and then ramping up to 285C at a rate of 10C min-1. Filament and detector were turned off during the elution of the injection solvent (i.e. methanol).For quantification, cyclohexanone was used as internal standardand GC-FID analyses were conducted in a 5890A model GC, fitted with a Restek Stabilwax column: 30 m × 0.32 mm ID × 1 m, usingair, hydrogen and helium with a split ratio of 100:1. Injector anddetector were kept at 300C and 320C respectively, while an ini-tial temperature of 35C was held for 5 min, ramping to 200C ata rate of 10C min-1, holding at this temperature for 20 min. Gassamples were collected in a gas bag and analysed using a Varian490-GC micro gas chromatograph and an IR Prestige 21 ShimadzuFTIR QP 5000 apparatus. IR spectra were processed using QASoft software.
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  • [ 79-14-1 ]
  • [ 623-50-7 ]
  • [ 627-82-7 ]
  • [ 556-52-5 ]
  • [ 116-09-6 ]
  • [ 107-02-8 ]
YieldReaction ConditionsOperation in experiment
62% With pretreated aluminium vanadium phosphate; In water; at 280℃; under 760.051 Torr;Catalytic behavior; Activation energy; The glycerol transformation was carried out in a continuous-flow fixed-bed reactor under atmospheric pressure, as previouslydescribed [23]. The reactor was made of stainless-steel tubing(7 mm internal diameter and 190 mm long), placed in a tubularelectric furnace. The temperature was monitored by a thermocou-ple located in the catalyst bed. The analysis of the feed and reactionproducts was carried out on-line using a multicolumn gas chro-matograph (GC) equipped with both flame ionization (FID) andthermal conductivity (TCD) detectors in parallel. The compoundswere separated in a capillary column, DB-1 (100% methylpolysilox-ane, 60 m x 0,25 mm x 0,25 m).The catalyst (100 mg) was pretreated at the reaction tempera-ture during 2 h in a N2flow (75 mL/min). A 36 wt% glycerol (99.5%,Sigma-Aldrich) aqueous solution was fed at 0.6 mL/h (0.69 mol/sof glycerol). In general, each catalytic test was conducted at least for3 h at different temperatures (220C, 250C and 280C). The reac-tion products were identified by chromatographic patterns and/or agas chromatograph-mass spectrometer (GC-MS) (VARIAN CP 3800,QUADRUPOLE MS 1200) also equipped with a capillary column DB-1. A blank test showed the absence of homogeneous reactions andthe reactor inactivity in the absence of a catalyst.
  • 14
  • [ 9004-34-6 ]
  • [ 57-55-6 ]
  • [ 107-21-1 ]
  • [ 5077-67-8 ]
  • [ 116-09-6 ]
  • [ 584-03-2 ]
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