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1-Methyl-4-piperidone

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CAS:1445-73-4
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1-Methyl-4-piperidone Basic information
Product Name:1-Methyl-4-piperidone
Synonyms:1-METHYL-4-PIPERIDONE;1-METHYL-4-PIPERIDINONE;1-METHYLTETRAHYDROPYRIDIN-4(1H)-ONE;N-METHYL-GAMMA-PIPERIDONE;AKOS BBS-00004237;4-PIPERIDINONE, 1-METHYL-;1-Methyl-4-piperidone,98%;N-Methyl-4-piperidone ,98%
CAS:1445-73-4
MF:C6H11NO
MW:113.16
EINECS:215-895-5
Product Categories:Miscellaneous;Piperidines, Piperidones, Piperazines;PHARMACEUTICAL INTERMEDIATES;Amines and Anilines;Carbonyl Compounds;Piperidine;Heterocycles;Miscellaneous Reagents;Building Blocks;Heterocyclic Building Blocks;Piperidones;pharmaceutical;Thiadiazoles;1445-73-4;john's
Mol File:1445-73-4.mol
1-Methyl-4-piperidone Structure
1-Methyl-4-piperidone Chemical Properties
Melting point 192-193 °C(Solv: ethyl acetate (141-78-6))
Boiling point 55-60 °C11 mm Hg(lit.)
density 0.92 g/mL at 25 °C (lit.)
refractive index n20/D 1.460
Fp 140 °F
storage temp. Store below +30°C.
solubility Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
pka8.02±0.20(Predicted)
form Liquid
color Clear yellow to orange
Specific Gravity0.92
PH12 (100g/l, H2O, 20℃)
Water Solubility MISCIBLE
Sensitive Air Sensitive
BRN 106924
Major ApplicationPFAS testing
InChI1S/C6H11NO/c1-7-4-2-6(8)3-5-7/h2-5H2,1H3
InChIKeyHUUPVABNAQUEJW-UHFFFAOYSA-N
SMILESCN1CCC(=O)CC1
CAS DataBase Reference1445-73-4(CAS DataBase Reference)
NIST Chemistry Reference4-Piperidinone, 1-methyl-(1445-73-4)
Safety Information
Hazard Codes C,Xi
Risk Statements 34-10-36/37/38
Safety Statements 23-24/25-37/39-26
RIDADR UN 1224 3/PG 3
WGK Germany 3
Hazard Note Irritant
HazardClass 3
PackingGroup III
HS Code 29333999
Storage Class3 - Flammable liquids
Hazard ClassificationsFlam. Liq. 3
MSDS Information
ProviderLanguage
1-Methyltetrahydropyridin-4(1H)-one- English
SigmaAldrich English
ACROS English
ALFA English
1-Methyl-4-piperidone Usage And Synthesis
Chemical Propertiesclear yellow to orange liquid
Uses1-Methyl-4-piperidone, are widely used in artificial fibre industry. They are polymerizable and used as nylon precursors. They have excellent applications as solvents and as intermediates for organic synthesis. They are used in the aqueous carrier medium and amide penetrants in inks and water soluble paints.
ApplicationN-Methyl-4-piperidone can be used as a reactant to prepare:
Spiropiperidine rings by reacting with malononitrile and electrophiles or Michael acceptors.
(3E,5E)-1-Methyl-3,5-bis(phenylmethylene)-4-piperidinone by reacting with benzaldehyde via Michael addition, followed by intramolecular O-cyclization/elimination sequential reactions.
N,N′-Dimethylbispidinone by utilizing a double Mannich condensation method.
Preparation[JACS (1948) vol 70 p 1820] for the synthesis of 1-methyl-4-piperidone:
To a one-liter flask containing 350 ml of 20 % hydrochloric acid was added 86 g. of 1-methyl-3-carbethoxy-4-piperidone hyrdrochloride. After refluxing for one hour, the ferric chloride reagent gave no coloration. The solution was evaporated to dryness on a steam-bath at 10 mm. pressure. The solid product, heated at 100 °C for 4 hours at 0.1 mm and further dried over solid KOH for 24 hours, weighed 57.7 g, m.p. 80 - 120 °C.
Although this melting range goes above that of the pure comound 0.45 of crude material dissolved in 90 ml. of hot acetone gave 0.40 g of pure compoundd melting at 93 - 95 °C. Other samples of crude piperidone hydrochloride showed even higher melting points than the one mentioned above, yet this apperently impure material always gave good yields of sharp melting product when recrystallized.
Purification MethodsIt is best purified by fractional distillation The hydrochloride of the hydrate (4-diol) has m 94.7-95.5o, but the anhydrous hydrochloride which crystallises from CHCl3/Et2O has m 165-168o (164-167o) and can also be obtained by sublimation at 120o/2mm. The oxime has m 130-132o (from Me2CO). The methiodide crystallises from MeOH, the crystals with 1MeOH have m 189-190o, and the solvent-free iodide has m 202-204o(dec). [Lyle et al. J Org Chem 24 342 1959, Bowden & Greeen J Chem Soc 1164 1952, Tomita Yakugaku Zasshi (J Pharm Soc Japan) 71 1053 1951, Beilstein 21 IIII/IV 3183, 21/6 V 419.]
References [1] Robert E. Lyle, Laurence Ladd, Richard Munk. “The Asinger Reaction with 1-Methyl-4-piperidone.” The Journal of Organic Chemistry 30 1 (1965): 293–294.
[2] Wildau, Martha. “Ein acidimetrisches Bestimmungsverfahren alkylsubstituierter 1-Methyl-4-piperidone.” Analytical and Bioanalytical Chemistry 147 3 (1955): 231–231.
Tag:1-Methyl-4-piperidone(1445-73-4) Related Product Information
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