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[ CAS No. 88-12-0 ] {[proInfo.proName]}

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Chemical Structure| 88-12-0
Chemical Structure| 88-12-0
Structure of 88-12-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 88-12-0 ]

CAS No. :88-12-0 MDL No. :MFCD00003197
Formula : C6H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :WHNWPMSKXPGLAX-UHFFFAOYSA-N
M.W : 111.14 Pubchem ID :6917
Synonyms :

Calculated chemistry of [ 88-12-0 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.38
TPSA : 20.31 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) : -6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 0.37
Log Po/w (WLOGP) : 0.37
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 1.09
Consensus Log Po/w : 0.76

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.7
Solubility : 22.4 mg/ml ; 0.201 mol/l
Class : Very soluble
Log S (Ali) : -0.36
Solubility : 48.3 mg/ml ; 0.435 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.6
Solubility : 28.0 mg/ml ; 0.252 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 88-12-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P261-P270-P202-P201-P271-P264-P280-P308+P313-P361+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338+P310-P403+P233-P405 UN#:2810
Hazard Statements:H311-H302+H332-H315-H318-H351-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 88-12-0 ]

* 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 [ 88-12-0 ]
  • Downstream synthetic route of [ 88-12-0 ]

[ 88-12-0 ] Synthesis Path-Upstream   1~22

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Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 47, p. 13181 - 13187
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YieldReaction ConditionsOperation in experiment
90% at 350℃; for 10 h; The alkaline component NH3 with N-hydroxyethylpyrrolidone steam as well as N2 were mixed. Heat to reaction temperature to obtained gaseous starting material mixture. Gaseous starting material mixture specific composition is 0.01NH3+ 0.05NHP + 0.94N2; then, The said starting material mixture, under temperature 350 °C, pressure 0.1 MPa and gas phase space velocity 2000h-1 conditons, goes through fixed bed reactor loaded with step A prepared catalyst. After reacting for 10 hours and reaching stability, collect the N-vinylpyrrolidone discharged from the fixed-bed reactor. With the embodiment 1 the same analysis method, in this embodiment the prepared N-vinyl pyrrolidone the analysis of products, obtained by the analysis result to calculate: the conversion rate of NHP 94.0percent, NVP selective 95.7percent, NVP yield 90.0percent, recombinant sub-impurity selective 1.7percent.
82% at 348℃; for 1 h; EXAMPLE 1
A tube (0.81" ID with 0.185" thermowell) was packed with 10 cc (10.95 g) of Ca/Zn oxide (30 wt. percent Ca) that had been ground to 14/30 mesh.The tube was heated in an electric furnace to 348° C. under a nitrogen flow of 18 SLH (standard liters per hour).
N-hydroxyethyl pyrrolidone was fed at 9.9 g/h to the top of the reactor and the product was recovered in an ice trap for analysis.After 1 hour, N-vinyl pyrrolidone was obtained in 82.0percent yield (97.8percent conversion of N-hydroxyethyl pyrrolidone with 83.9percent selectivity to N-vinyl pyrrolidone).
67.5% at 331 - 359℃; for 1 h; Example 1 is repeated except Ca/Zn oxide (8.85 g, 14.x.30 mesh, 9 wt. percent Ca) is used. After 1 hour at 336° C., N-vinyl pyrrolidone was obtained in 69.8percent yield (99.9percent conversion of N-hydroxyethyl pyrrolidone with 69.8percent selectivity to N-vinyl pyrrolidone). EXAMPLE 3 [0020] Example 1 is repeated except Ca/Zn oxide (8.63 g, 14.x.30 mesh, 16 wt. percent Ca) is used. After 1 hour at 331° C., N-vinyl pyrrolidone was obtained in 67.5percent yield (84.8percent conversion of N-hydroxyethyl pyrrolidone with 79.6percent selectivity to N-vinyl pyrrolidone). EXAMPLE 4 [0021] Example 1 is repeated except Ca/Zn oxide (9.30 g, 14.x.30 mesh, 16 wt. percent Ca) is used. After 1 hour at 359° C., N-vinyl pyrrolidone was obtained in 80.4percent yield (94.8percent conversion of N-hydroxyethyl pyrrolidone with 84.8percent selectivity to N-vinyl pyrrolidone).
66.7% at 356 - 360℃; for 2 - 4 h; Example 1 is repeated except Mg/Zn oxide (7.15 g, 14.x.30 mesh, 20 wt. percent Mg) is used. After 4 hours at 356° C., N-vinyl pyrrolidone was obtained in 66.7percent yield (99.4percent conversion of N-hydroxyethyl pyrrolidone with 67.1percent selectivity to N-vinyl pyrrolidone). EXAMPLE 6 [0024] Example 1 is repeated except Mg/Zn oxide (6.79 g, 14.x.30 mesh, 10 wt. percent Mg) is used. After 2 hours at 360° C., N-vinyl pyrrolidone was obtained in 88.3percent yield (98.9percent conversion of N-hydroxyethyl pyrrolidone with 89.3percent selectivity to N-vinyl pyrrolidone).
44% at 366℃; for 1 h; COMPARATIVE EXAMPLE 1
Example 1 is repeated except the Ca/Zn oxide is calcined in air to 500° C. prior to running.Analysis by XRD shows the presence of a crystalline ZnO phase.After 1 hour at 366° C., N-vinyl pyrrolidone was obtained in 44.0percent yield (62.0percent conversion of N-hydroxyethyl pyrrolidone with 70.9percent selectivity to N-vinyl pyrrolidone).
26.6% at 368℃; for 1 h; COMPARATIVE EXAMPLE 4
Example 1 is repeated except MgO (7.93 g, 14*30 mesh) is used.After 1 hour at 368° C., N-vinyl pyrrolidone was obtained in 26.6percent yield (63.8percent conversion of N-hydroxyethyl pyrrolidone with 41.7percent selectivity to N-vinyl pyrrolidone).
The above results demonstrate the improved N-vinyl pyrrolidone production using amorphous Mg/Zn oxide catalyst (Examples 5 and 6) as compared to use of only MgO catalyst (Comparative Example 4).
11.5% at 359℃; for 1 h; Example 1 is repeated except the Ca/Zn oxide is calcined in air to 700° C. prior to use. Analysis by XRD shows the presence of both crystalline ZnO and CaO phases. After 1 hour at 359° C., NVP was obtained in 11.5percent yield (76.1percent conversion of N-hydroxyethyl pyrrolidone with 15.1percent selectivity to N-vinyl pyrrolidone).
2.7% at 377℃; for 1 h; COMPARATIVE EXAMPLE 3
Example 1 is repeated except CaCO3 (6.07 g, 14*30 mesh) is used.After 1 hour at 377° C., N-vinyl pyrrolidone was obtained in 2.7percent yield (19.7percent conversion of N-hydroxyethyl pyrrolidone with 13.6percent selectivity to N-vinyl pyrrolidone).
The above examples demonstrate the superior results achieved through practice of the invention (Example 1) as compared to similar examples where the mixed oxide is calcined at 500° C. (Comparative Example 1), at 700° C. (Comparative Example 2), and where only a calcium carbonate catalyst is used (Comparative Example 3).
Examples 2-4 show that the Ca content can vary and still produce a desirable result:
87 %Chromat. for 1 h; Inert atmosphere; Sealed tube To prepare as a catalyst to be used in the second-stage reaction, 7.76 g of cesium carbonate was dissolved in 250 g of water, and 30 g of silicon oxide was added thereto while the solution was heated to 90° C. and stirred. The mixture was dried at 120° C. for 20 hours. The resulting solid was crushed to size of 9-16 mesh, calcined in air at 500° C. for 2 hours, thereby preparing a catalyst having a composition of Cs1Si10 (expressed as atomic ratio excluding oxygen). [0238] 30 ml of the catalyst was charged into a stainless steel reaction tube having an inner diameter of 15 mm, and the reaction tube was placed in a reactor at 360° C. Raw material gas obtained by diluting N-(2-hydroxyethyl)-2-pyrrolidone in nitrogen to reach a partial pressure of 76 mmHg was supplied to the reaction tube at a space velocity of 200 h−1 and allowed to react at atmospheric pressure. After 1 hour from the initiation of the reaction, gas discharged from the reactor was captured by methanol, and the gas chromatography analysis of the gas showed that the yield of N-vinyl-2-pyrrolidone was 87 mole percent.

Reference: [1] Patent: , 2016, , . Location in patent: Paragraph 0171; 0172; 0173; 0174
[2] Patent: US2004/63970, 2004, A1, . Location in patent: Page 1
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[4] Patent: US2004/63970, 2004, A1, . Location in patent: Page 2
[5] Patent: US2004/63970, 2004, A1, . Location in patent: Page 1
[6] Patent: US2004/63970, 2004, A1, . Location in patent: Page 2
[7] Patent: US2004/63970, 2004, A1, . Location in patent: Page 1
[8] Patent: US2004/63970, 2004, A1, . Location in patent: Page 1
[9] Patent: US2669570, 1951, ,
[10] Journal of the American Chemical Society, 1952, vol. 74, p. 4959
[11] Patent: US5625076, 1997, A,
[12] Patent: US5625076, 1997, A,
[13] Patent: US5625076, 1997, A,
[14] Patent: US5625076, 1997, A,
[15] Patent: US5625076, 1997, A,
[16] Patent: US5625076, 1997, A,
[17] Patent: US5625076, 1997, A,
[18] Patent: US5625076, 1997, A,
[19] Patent: US5625076, 1997, A,
[20] Patent: US5625076, 1997, A,
[21] Patent: US5625076, 1997, A,
[22] Patent: US5801252, 1998, A,
[23] Patent: US5801252, 1998, A,
[24] Patent: US5801252, 1998, A,
[25] Patent: US5801252, 1998, A,
[26] Patent: WO2006/109869, 2006, A1, . Location in patent: Page/Page column 13-14
[27] Bulletin of the Chemical Society of Japan, 2008, vol. 81, # 4, p. 449 - 459
[28] Patent: WO2006/118319, 2006, A1, . Location in patent: Page/Page column 13
[29] Patent: US2014/296466, 2014, A1, . Location in patent: Paragraph 0236; 0237; 0238
  • 3
  • [ 616-45-5 ]
  • [ 96-49-1 ]
  • [ 88-12-0 ]
YieldReaction ConditionsOperation in experiment
82.13% With TEMPOL; 1,8-diazabicyclo[5.4.0]undec-7-ene In 5,5-dimethyl-1,3-cyclohexadiene at 100 - 120℃; for 3.5 h; Dean-Stark To a 1 liter four necked flask with thermometer, dessicant tube, electrical stirrer, Dean Stark apparatus, is added 85,1g (1 mol) of butyrolactam, 130g (1.1 mol) of 1,3-dioxolan-2-one, 500ml of xylene , 300mg of 4-hydroxy-TEMPO as inhibitor and 6,4g of catalyst 1, 8-Diazabicyclo [5,4,0] undec-7-ene (DBU). [0065] The whole reaction mass is heated at 100°C to react during 30mn. Once the reaction of decarboxylation start, water is gradually generated and separated along with the water carrying agent. The reaction stops after temperature reach 120°C after 3h and no longer water is generated. [0066] The resulting product is further separated and the fraction at 90°C /9mmHg is collected. The product yield 82,13percent of N-ethenyl butyrolactam with a purity of 99,3percent.
Reference: [1] Patent: EP2835365, 2015, A1, . Location in patent: Paragraph 0064; 0065; 0066
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YieldReaction ConditionsOperation in experiment
99% at 220℃; To a 30 mL recovery flask was added N- (α-ethoxyethyl) -2-pyrrolidone (8.50 g, 54.1 mmol) and the surface modified hydroxyapatite catalyst prepared in Example 1 (451 mg) were added.The mixture was heated and stirred at a temperature of 220 ° C., and ethanol produced by the reaction was continuously removed out of the reaction system by distillation. Analysis of the reaction solution after 20 minutes of the reaction by 1 H NMR revealed that the conversion of N- (α-ethoxyethyl) -2-pyrrolidone was> 99percent, the yield and selectivity of N-vinyl-2-pyrrolidone were 99percent,> 99percent.
Reference: [1] Patent: JP5663964, 2015, B2, . Location in patent: Paragraph 0041
[2] Patent: US5700946, 1997, A,
  • 5
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YieldReaction ConditionsOperation in experiment
69%
Stage #1: Distillation at reduced pressure
Stage #2: at 150℃; for 1 h;
Example 1
85.1 g (1 mol) of 2-pyrrolidone and 2.05 g (30 mmol) of potassium methoxide were initially charged, and methanol was distilled off under reduced pressure.
30 g of the mixture thus obtained were subjected to vinylation at 150° C. and 20 bar of acetylene for 1 h.
The yield of N-vinylpyrrolidone (NVP) was 69percent of theory (determined by gas chromatography).
95 %Chromat. at 170℃; for 0.2 h; Example 2Without Polymerization InhibitorA mixture of 10.0 g (118 mmol) of 2-pyrrolidone, 0.5 g (0.77 mmol) of Re2(CO)10 and 17.4 g of toluene were subjected to vinylation at 170° C. under a nitrogen pressure of 2 bar and an acetylene pressure of 18 bar for 0.2 h. The yield of N-vinyl-2-pyrrolidone determined by GC analysis was 95percent.
98 %Chromat. With 2,6-di-tert-butyl-4-methyl-phenol In toluene at 170℃; for 0.2 h; Example 3With Polymerization InhibitorA mixture of 10.0 g (118 mmol) of 2-pyrrolidone, 0.5 g (0.77 mmol) of Re2(CO)10, 53 mg (0.24 mmol) of di-tert-butyl-p-cresol and 17.4 g of toluene were subjected to vinylation at 170° C. under a nitrogen pressure of 2 bar and an acetylene pressure of 18 bar for 0.2 h. The yield of N-vinyl-2-pyrrolidone determined by GC analysis was 98percent.
Reference: [1] Patent: US4939273, 1990, A,
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Reference: [1] Gazzetta Chimica Italiana, 1993, vol. 123, # 8, p. 457 - 462
[2] Journal of the American Chemical Society, 1952, vol. 74, p. 4959
[3] Journal of the American Chemical Society, 1952, vol. 74, p. 4959
[4] Journal of the American Chemical Society, 1952, vol. 74, p. 4959
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Reference: [1] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1957, p. 1457,1461; engl. Ausg. S. 1478, 1481
[2] Justus Liebigs Annalen der Chemie, 1956, vol. 601, p. 81,104
[3] Patent: US4873336, 1989, A,
[4] Patent: US2806847, 1955, ,
[5] Patent: US2806848, 1956, ,
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Reference: [1] Tetrahedron, 2013, vol. 69, # 5, p. 1600 - 1605
[2] Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 324 - 329
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  • [ 111-34-2 ]
  • [ 88-12-0 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 11, p. 1845 - 1848
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  • [ 3445-11-2 ]
  • [ 88-12-0 ]
  • [ 75-07-0 ]
YieldReaction ConditionsOperation in experiment
0.05% at 390℃; Example 2 [0065] The gas phase intramolecular dehydration of N-hydroxyethyl pyrrolidone by the use of the same catalyst as in Example 1 was carried out under the following conditions. [0066] Reaction temperature: 390° C. [0067] Feed gas: N-hydroxyethyl pyrrolidone 100 vol. percent [0068] The reaction gas containing N-vinyl pyrrolidone was collected with N-hydroxyethyl pyrrolidone. The collection liquid had the following composition. [0069] 0.91percent of light boiling amines; 0.05percent of acetaldehyde; 57.30percent of N-vinyl pyrrolidone; 25.00percent of N-hydroxyethyl pyrrolidone; 10.33percent of water; 5.20percent of Schiff base (formed by the reaction of the decomposed amine compounds with the aldehyde compounds); and 1.21percent of other substances. [0070] Then, the N-vinyl pyrrolidone was purified and the N-hydroxyethyl pirrolidone was recovered by using a continuous vacuum distillation apparatus composed of four distillation columns (three N-vinyl pyrrolidone purifying columns and one N-hydroxyethyl pyrrolidone recovering column) as illustrated in FIG. 1. [0071] Specifically, the collection liquid was supplied at a rate of 1 kg/h to the intermediate stage of the first distillation column and subjected to vacuum distillation therein under the conditions of 133 hPa of pressure, 90° C. of column top temperature, and 150° C. of column bottom temperature. Through the top of the column, light boiling amines and N-vinyl pyrrolidone were extracted. Through the bottom of the column, N-hydroxyethyl pyrrolidone, Schiff base, and other heavy fraction were extracted. [0072] The top liquid of the column was supplied to the intermediate stage of the second distillation column and subjected to vacuum distillation under the conditions of 66 hPa in pressure, 45° C. in column top temperature, and 60° C. in column bottom temperature. Through the top of the column, light boiling amines were extracted. Through the bottom of the column, a liquid formed of N-vinyl pyrrolidone and N-hydroxyethyl pyrrolidone was extracted. [0073] Then, the bottom liquids of the first and the third distillation column were mixed and supplied to the intermediate stage of the fourth distillation column. In the fourth distillation column, the vacuum distillation was carried out under the conditions of 260 hPa in pressure, 70° C. in column top temperature, and 130° C. in column bottom temperature. Through the top of the column, a liquid consisted of 18.01percent of acetaldehyde, 1.00percent of N-vinyl pyrrolidone, 63.5percent of water, and 17.94percent of other substances was extracted. The bottom liquid of the column consisted of 88.08percent of N-hydroxyethyl pyrrolidine, 0.83percent of Schiff base, and 11.09percent of other substances. [0074] The vacuum lines issuing from the tops respectively of the first distillation column, the second distillation column, and the third distillation column were joined short of the entrance to the vacuum pump A and connected to the vacuum pump A. The vacuum line issuing from the top of the fourth distillation column was connected to the vacuum pump B. The purifying step and the recovering step were decompressed with mutually different decompression systems. [0075] When the continuous distillation was performed for one month, the operation of distillation proceeded steadily without entailing either formation of a deposit in the vacuum lines or fluctuation of vacuum pressure.
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Reference: [1] Gazzetta Chimica Italiana, 1993, vol. 123, # 8, p. 457 - 462
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  • [ 29094-61-9 ]
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  • [ 3380-34-5 ]
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