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Chemical Structure| 927-63-9
Chemical Structure| 927-63-9
Structure of 927-63-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 927-63-9 ]

CAS No. :927-63-9 MDL No. :MFCD00006999
Formula : C5H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :RRLMPLDPCKRASL-ONEGZZNKSA-N
M.W : 99.13 Pubchem ID :638320
Synonyms :

Safety of [ 927-63-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3267
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 927-63-9 ]

* 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.

  • Upstream synthesis route of [ 927-63-9 ]
  • Downstream synthetic route of [ 927-63-9 ]

[ 927-63-9 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 927-63-9 ]
  • [ 86847-59-8 ]
  • [ 254-60-4 ]
Reference: [1] Synlett, 2006, # 3, p. 379 - 382
  • 2
  • [ 927-63-9 ]
  • [ 70298-89-4 ]
  • [ 253-72-5 ]
Reference: [1] Synlett, 2006, # 3, p. 379 - 382
  • 3
  • [ 60144-53-8 ]
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  • [ 396-30-5 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7288 - 7291
  • 4
  • [ 56619-93-3 ]
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  • [ 6931-19-7 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7288 - 7291
  • 5
  • [ 105-34-0 ]
  • [ 927-63-9 ]
  • [ 40134-18-7 ]
YieldReaction ConditionsOperation in experiment
93.9%
Stage #1: at 140℃; for 1 h; Microwave irradiation
In a reactor, 59 mL (0.5 mol) of methyl cyanoacetate was added to the reactor,N-ethylpyridine tetrafluoroborate 50 mL,3-dimethylaminopropenal 62 mL (0.5 mol) was homogeneously mixed,Microwave heating to 140 temperature and heat for 1h to carry out the reaction, TLC detection (oilEther: methylene chloride 1: 2 developed, sublimed iodine color)3-dimethylaminopropenal reaction completely, cooled to room temperature, organic solvent BEther 60mL extraction 3 times, residual phase ion water washing vacuum drying after repeated use, organic phase into the dry HCl gas, HPLC withThe reaction is continued until the reaction ends. Add the mass fraction of 20percent sodium hydroxide solution to adjust the pH = 5-6, separated, the water layer with ether20mL × 3 times extraction, combined organic layer, washed with water, molecular sieve drying, filtration, evaporation of solvent ether recovery, the residue byThe product was distilled at 110-115 ° C / 1 mmHg to prepare methyl 2-chloronicotinate and 80.6 g of colorless liquid in a yield of 93.9percent.
Reference: [1] Patent: CN105001154, 2017, B, . Location in patent: Paragraph 0060; 0061; 0062
  • 6
  • [ 105-56-6 ]
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  • [ 53087-78-8 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: at 90℃; for 4 h;
Ethyl cyanoacetate (59 mL, 0.5 mol) was added to the reactor,1-dodecyl-3-methylimidazolium chloride50 mL,3-dimethylaminopropenal 62 mL (0.5 mol) was homogeneously mixed,The oil bath was heated to 90 ° C and incubated for 4 hours. TLC detection (petroleum ether: methylene chloride 1: 2 expansion, sublimed iodine coloring) 3-dimethylaminophenaldehyde was complete,Cool to room temperature, organic solvent1,2-dichloroethane 60mL extraction 3 times, residual phase ion water washing vacuum drying and reuse,The organic phase was passed through a dry HBr gas and the HPLC was followed by the reaction until the reaction was complete.Add the mass fraction of 20percent sodium carbonate solution to adjust the pH = 5-6, liquid,For water use1,2-dichloroethane 20mL × 3 times extraction, the organic layer, combined with water,The molecular sieves were dried, filtered and the solvent was evaporated under reduced pressure1,2-dichloroethane was recovered to give ethyl 2-bromonicotinate, 108.4 g of a light brown liquid in a yield of 94.0percent.
93.5%
Stage #1: at 40℃; Sonication
Stage #2: at 40℃; Sonication
In a 500 mL three-necked flask equipped with a thermometer, first, 2-dimethylaminoacrolein (62 mL, 0.5 mol) and pyridine (20 mL) were added, and then 65 mL (0.6 mol) of ethyl cyanoacetate was added to prepare the prepared device. Into the ultrasonic instrument. Ultrasonic radiation conditions were set, and the reaction was carried out at a temperature of 40 °C, an ultrasonic power of 150 W, and a frequency of 20KHz TLC test (petroleum ether:dichloromethane 1:2 development, sublimation iodine development) 3-dimethylaminopropylene Aldehyde reaction is complete. After that, HBr gas was introduced and the ultrasonic irradiation conditions were as above, and the reaction was followed by HPLC until the reaction was completed. After the reaction is completed, add 30percent sodium hydroxide solution to adjust ρΗ = 5-6, and separate the layers. The aqueous layer is extracted with dichloromethane 20 mL x 3 times. The organic layers are combined, and the deionized water is washed with 10 mL of water. The organic layer was dried over anhydrous Na2SO4 , filtered, and the solvent was evaporated under reduced pressure in the liquid phase to obtain ethyl 2-bromonicotinate as light brown liquid, 107.5 g, with a yield of 93.5percent.
Reference: [1] Patent: CN105001154, 2017, B, . Location in patent: Paragraph 0049; 0050; 0051; 0052
[2] Patent: CN104945317, 2018, B, . Location in patent: Paragraph 0047; 0048
  • 7
  • [ 1820-80-0 ]
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  • [ 274-71-5 ]
YieldReaction ConditionsOperation in experiment
65% for 6 h; Reflux Preparation of compound 23a: pyrazolo[1,5-a]pyrimidineA mixture of 1 H-pyrazol-3-ylamine (32 g, 0.386 mol) and (E)-3-dimethylamino- propenal (38.2 g, 0.386 mol) in EtOH (500 ml_) was refluxed for 6 h. The solvent was removed in vacuo and the residue was purified via column chromatography (petroleum ether/EtOAc = 10:1 -2:1 ) which gave the title compound 23a as a white solid (30 g, 65percent).
Reference: [1] Synthesis, 2006, # 1, p. 59 - 62
[2] Patent: WO2010/16005, 2010, A1, . Location in patent: Page/Page column 116
  • 8
  • [ 141-86-6 ]
  • [ 927-63-9 ]
  • [ 15992-83-3 ]
YieldReaction ConditionsOperation in experiment
21% at 120℃; for 10 h; Part I-- Synthesis of [1,8]-Naphthyridin-2-ylamine; Pyridine-2,6-diamine (0.30 g, 2.8 mmol), 3-dimethylaminoacrolein (90percent, 0.30 g, 2.8mmol), and polyphosphoric acid (PPA) (2.7 mL) were combined and the reaction mixture washeated to 120 oc for 10 hours. Then, the reaction mixture was poured on ice water and neutralized with solid sodium carbonate. The resulting aqueous mixture was extracted threetimes with ethyl acetate and the combined organic extracts were washed with brine,concentrated, and purified by column chromatography (EtOAc/hexanes) to give [1,8]naphthyridin-2-ylamine. Yield 85 mg (21 percent). LCMS (ESI): calc. C8H7N3 = 145; obs. M+H =146.
Reference: [1] Patent: WO2013/169864, 2013, A2, . Location in patent: Paragraph 00198
  • 9
  • [ 927-63-9 ]
  • [ 86847-83-8 ]
  • [ 35170-93-5 ]
Reference: [1] Synlett, 2006, # 3, p. 379 - 382
  • 10
  • [ 927-63-9 ]
  • [ 35170-93-5 ]
Reference: [1] Synlett, 2006, # 3, p. 379 - 382
  • 11
  • [ 927-63-9 ]
  • [ 130721-78-7 ]
  • [ 35170-94-6 ]
Reference: [1] Synlett, 2006, # 3, p. 379 - 382
  • 12
  • [ 104-04-1 ]
  • [ 68-12-2 ]
  • [ 1205-59-0 ]
  • [ 78708-10-8 ]
  • [ 100-01-6 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 1520 - 1530
  • 13
  • [ 502-49-8 ]
  • [ 5043-86-7 ]
  • [ 75143-08-7 ]
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Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1980, vol. 29, # 6, p. 987 - 990[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1980, # 6, p. 1373 - 1376
  • 14
  • [ 624-67-9 ]
  • [ 124-40-3 ]
  • [ 927-63-9 ]
Reference: [1] Patent: DE944852, 1949, ,
[2] Journal of the Chemical Society, 1960, p. 3812,3819
  • 15
  • [ 75-44-5 ]
  • [ 68-12-2 ]
  • [ 927-63-9 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1958, vol. 23, p. 452,455
  • 16
  • [ 51513-20-3 ]
  • [ 3603-99-4 ]
  • [ 75143-09-8 ]
  • [ 927-63-9 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1980, vol. 29, # 6, p. 987 - 990[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1980, # 6, p. 1373 - 1376
  • 17
  • [ 67-56-1 ]
  • [ 5043-87-8 ]
  • [ 927-63-9 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1981, vol. 30, # 5, p. 820 - 824[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1981, # 5, p. 1060 - 1064
  • 18
  • [ 105-57-7 ]
  • [ 75-44-5 ]
  • [ 107-06-2 ]
  • [ 68-12-2 ]
  • [ 13984-13-9 ]
  • [ 927-63-9 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1953, vol. 23, p. 452,458
  • 19
  • [ 5220-49-5 ]
  • [ 927-63-9 ]
  • [ 53400-41-2 ]
  • [ 56798-21-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2000, vol. 37, # 1, p. 41 - 46
  • 20
  • [ 1378847-65-4 ]
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  • [ 1151814-36-6 ]
Reference: [1] Patent: WO2010/141273, 2010, A1, . Location in patent: Page/Page column 52-53
  • 21
  • [ 927-63-9 ]
  • [ 1345456-45-2 ]
  • [ 337958-60-8 ]
YieldReaction ConditionsOperation in experiment
0.42 g
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70 - -60℃; for 1.5 h; Inert atmosphere
Stage #2: at -70 - 20℃; for 0.833333 h; Inert atmosphere
Intermediate 7: 5,7-Dichloro-1,6-naphthyridine[0384]N-(2,6-Dichloro-4-pyridinyl)-2,2-dimethylpropanamide (1 g, 4.05 mmol) was taken up in THF (10 ml) under nitrogen and cooled to n-Butyl lithium (4.05 ml, 10.12 mmol, 2.5M solution in hexanes) was added over 30 min keeping the temperature below −60° C. and then stirred at below −70° C. for 1 h. (2E)-3-(dimethylamino)-2-propenal (0.607 ml, 6.07 mmol) in THF (2 ml) was added over 30 min keeping the temperature below −60° C. The reaction was stirred at below −70° C. for 20 min and then allowed to warm to room temperature. LCMS showed that no starting material remained so the reaction was quenched with 5M HCl (5 ml) and refluxed overnight. LCMS showed good conversion to product so the reaction was cooled to room temperature. The reaction mixture was basified with solid K2CO3 and extracted with EtOAc (4×25 ml). The combined organics were dried with Na2SO4, filtered and concentrated to yield a brown solid. The crude product was applied to a samplet and columned using a 40+M eluting with 12percent diethyl ether in cyclohexane for 2 CVs, then with 12percent-63percent diethyl ether in cyclohexane over 10 CVs then held at 63percent for SCVs. Appropriate fractions were combined and evaporated to give the title compound as a yellow solid (0.42 g).[0386]LCMS (Method B): Rt=0.89 min, MH+ 199/201
Reference: [1] Patent: WO2011/134971, 2011, A1, . Location in patent: Page/Page column 12; 13; 53; 54
[2] Patent: US2013/40984, 2013, A1, . Location in patent: Paragraph 0384-0386
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