626-58-4

Basic information

• Product Name: 4-Methylpiperidine
• Synonyms: LABOTEST-BB LTBB000596;HEXAHYDRO-G-PICOLINE;GAMMA-PIPECOLINE;4-PIPECOLINE;4PPC;4-METHYLPIPERIDINE;AKOS BBS-00003666;4-methyl-piperidin
• CAS NO: 626-58-4
• Molecular Formula: C₆H₁₃N
• Molecular Weight: 99.17
• EINECS: 210-954-1
• Product Categories: Piperidine;Building Blocks;C5 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines
• Mol File: 626-58-4.mol
• Article Data: 25

Chemical Properties

• Melting Point: 4-5 °C
• Boiling Point: 124 °C(lit.)
• Flash Point: 45 °F
• Appearance: Clear slightly yellow/Liquid
• Density: 0.838 g/mL at 25 °C(lit.)
• Vapor Pressure: 10.1mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: Flammables area
• Solubility: Chloroform
• PKA: pK1:11.23(+1) (25°C,μ=0.5)
• Water Solubility: miscible
• BRN: 1083
• CAS DataBase Reference: 4-Methylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylpiperidine(626-58-4)
• EPA Substance Registry System: 4-Methylpiperidine(626-58-4)

Safety Data

• Hazard Codes: F,Xi,T
• Statements: 11-36/37/38-36-20/21-10-61
• Safety Statements: 16-26-36-45-36/37-53
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 626-58-4(Hazardous Substances Data)

Usage

Chemical Properties

clear slightly yellow liquid

Uses

Different sources of media describe the Uses of 626-58-4 differently. You can refer to the following data:
1. 4-Methylpiperidine is used as a catalyst in the synthesis of stilbene derivatives as anti-malarial agents. It also serves as an anti-corrosive compound for iron.
2. 4-Methylpiperidine acts as a catalyst in the preparation of stilbene derivatives. It is used as an anti-corrosive compound for iron. It is also used in the synthesis of peptides to remove or deprotection of 9-fluorenylmethyloxycarbonyl (Fmoc) groups.

Purification Methods

Purify it via the hydrochloride (m 189o). It is freed from 3-methylpyridine by zone melting. The hydrobromide has m 173o(from butanone/*C6H6). [Beilstein 20 III/IV 1511, 20/4 V 116.]

InChI:InChI=1/C6H13N/c1-6-2-4-7-5-3-6/h6-7H,2-5H2,1H3/p+1

Upstream product

• 123-91-1 1,4-dioxane 
• 858795-25-2 3-methyl-glutaric acid bis-phenethylamide 
• 138163-12-9 benzyl 4-methylene-1-piperidinecarboxylate 
• 32049-46-0 sodium 4-methyl-piperidinedithiocarbamate 
• 45798-02-5 4-methyl-1-piperidine dithiocarboxylic acid 
• 85872-87-3 4-(4-methylpiperidin-1-yl)-benzonitrile 
• 51462-37-4 3,6-bis-[(α-4'-methylpiperidino-isobutyryl)-amino]-acridine 
• 383865-57-4 4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine 
• 1453-82-3 isonicotinamide 
• 113118-87-9 4-Methyl-1-(phenoxycarbonyl)-1,4-dihydropyridine 
• 333444-36-3 phenyl 4-methylpiperidine-1-carboxylate 
• 4457-71-0 3-methylpentane-1,5-diol 
• 100-46-9 benzylamine 
• 108-89-4 picoline 

Downstream Products

• 121836-27-9 2,6-bis(4'-methylpiperidin-1'-ylmethyl)-4-nitrophenol 
• 137488-10-9 2-(4-Methyl-piperidin-1-ylmethyl)-5-trifluoromethyl-phenol 
• 99541-50-1 6-(4-Methoxy-benzoyl)-3-(4-methyl-piperidin-1-ylmethyl)-3H-benzooxazol-2-one 
• 99541-45-4 6-(2-Chloro-benzoyl)-3-(4-methyl-piperidin-1-ylmethyl)-3H-benzooxazol-2-one 
• 99552-29-1 3-(4-Methyl-piperidin-1-ylmethyl)-6-(4-nitro-benzoyl)-3H-benzooxazol-2-one 
• 349089-67-4 4-methyl-1-phenylacetyl-piperidine 
• 86543-00-2 4-Methyl-piperidine-1-carbothioic acid (2-cyano-4,5-dimethoxy-phenyl)-amide 
• 39123-23-4 1-(2-hydroxyethyl)-4-methylpiperidine 
• 91595-79-8 4-Methyl-1-oxiranylmethyl-piperidine 
• 127396-52-5 4,6-bis(4'-methylpiperidin-1'-ylmethyl)-2-nitrophenol 
• 91045-33-9 3-{1-[1-(4-Methyl-piperidin-1-ylmethyl)-1H-benzoimidazol-2-yl]-2-phenyl-ethyl}-2-phenyl-3H-quinazolin-4-one 
• 125102-65-0 5-(4-methylpiperidinomethyl)-3-phenylpyrrolo<2,1-a>phthalazin-6(5H)-one 

Relevant articles and documents

PRODUCTION METHOD OF CYCLIC COMPOUND

PROBLEM TO BE SOLVED: To provide an industrially simple production method of a cyclic compound. SOLUTION: A production method of a cyclic compound includes a step to obtain a reduced form (B) by reducing an unsaturated bond in a ring structure of an aromatic compound (A) by means of catalytic hydrogenation of the aromatic compound (A) or its salt using palladium carbon as a catalyst under a normal pressure, in which the aromatic compound (A) has one or more ring structures selected from a group consisting of a five membered-ring, a six membered-ring, and a condensed ring of the five membered-ring or the six membered-ring with another six membered-ring, a hetero atom can be included in the ring structure, and the aromatic compound (A) can have one or two side chains bonded to the ring structure and does not have any carbon-carbon triple bond in the side chain. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Hydrogenation of N-Heteroarenes Using Rhodium Precatalysts: Reductive Elimination Leads to Formation of Multimetallic Clusters

A rhodium-catalyzed method for the hydrogenation of N-heteroarenes is described. A diverse array of unsubstituted N-heteroarenes including pyridine, pyrrole, and pyrazine, traditionally challenging substrates for hydrogenation, were successfully hydrogenated using the organometallic precatalysts, [(η5-C5Me5)Rh(N-C)H] (N-C = 2-phenylpyridinyl (ppy) or benzo[h]quinolinyl (bq)). In addition, the hydrogenation of polyaromatic N-heteroarenes exhibited uncommon chemoselectivity. Studies into catalyst activation revealed that photochemical or thermal activation of [(η5-C5Me5)Rh(bq)H] induced C(sp2)-H reductive elimination and generated the bimetallic complex, [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H]. In the presence of H2, both of the [(η5-C5Me5)Rh(N-C)H] precursors and [(η5-C5Me5)Rh(μ2,η2-bq)Rh(η5-C5Me5)H] converted to a pentametallic rhodium hydride cluster, [(η5-C5Me5)4Rh5H7], the structure of which was established by NMR spectroscopy, X-ray diffraction, and neutron diffraction. Kinetic studies on pyridine hydrogenation were conducted with each of the isolated rhodium complexes to identify catalytically relevant species. The data are most consistent with hydrogenation catalysis prompted by an unobserved multimetallic cluster with formation of [(η5-C5Me5)4Rh5H7] serving as a deactivation pathway.

Chemoselective reduction of heteroarenes with a reduced graphene oxide supported rhodium nanoparticle catalyst

Rhodium nanoparticles immobilized on reduced graphene oxide were obtained from the microwave-induced thermal decomposition of Rh6(CO)16 in the ionic liquid [bmim][BF4] (bmim = 1-butyl-3-methylimidazolium cation) in the absence of additional stabilizing agents. The resulting rhodium nanoparticles are 99%, without interfering with other reducible groups, and with high conversions. Related catalysts prepared using conventional thermal heating were prepared for comparison purposes and were found to be considerably less active.