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109-05-7

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109-05-7 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 109-05-7 differently. You can refer to the following data:
1. Colorless to yellow liquid; pepper-like aroma.
2. CLEAR YELLOW LIQUID

Uses

Different sources of media describe the Uses of 109-05-7 differently. You can refer to the following data:
1. Reactant for C-2 arylation of piperidines through directed transition metal-catalyzed sp3 C-H activation1Reactant for synthesis of:? ;Azepan-4-ones via two step [5+2] annulation2? ;2-Aminobenzoxazoles3? ;Unsymmetrically substituted ureas4? ;Corticotropin-releasing factor receptor type 1 antagonists5? ;Gefitinib analogues with anti-tumor activity6
2. 2-Methylpiperidine, is used for the oxidation of secondary amines to nitrones by means of H2O2 catalyzed by Sodium tungsten oxide dihydrate.

Aroma threshold values

High strength; ammoniacal type; recommend smelling in a 1.0% solution or less.

Taste threshold values

Amine, creamy, taco, lettuce taste at 5 ppm in water.

Synthesis Reference(s)

Journal of the American Chemical Society, 111, p. 4108, 1989 DOI: 10.1021/ja00193a056

Check Digit Verification of cas no

The CAS Registry Mumber 109-05-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 109-05:
(5*1)+(4*0)+(3*9)+(2*0)+(1*5)=37
37 % 10 = 7
So 109-05-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H13N/c1-6-4-2-3-5-7-6/h6-7H,2-5H2,1H3/p+1/t6-/m1/s1

109-05-7 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (L02567)  2-Methylpiperidine, 98+%   

  • 109-05-7

  • 100ml

  • 699.0CNY

  • Detail
  • Alfa Aesar

  • (L02567)  2-Methylpiperidine, 98+%   

  • 109-05-7

  • 500ml

  • 1403.0CNY

  • Detail
  • Aldrich

  • (M72803)  2-Methylpiperidine  98%

  • 109-05-7

  • M72803-100ML

  • 460.98CNY

  • Detail

109-05-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Methylpiperidine

1.2 Other means of identification

Product number -
Other names 2-METHYL-PIPERIDINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:109-05-7 SDS

109-05-7Related news

Absorption of carbon dioxide by the mixed aqueous absorbents using 2-Methylpiperidine (cas 109-05-7) as a promoter08/25/2019

Mixed solvents based on tertiary amine and sterically hindered amine were tested for CO2 capture performance with 2-methylpiperidine (2MPD) as an additive to improve the mass transfer rate of those absorbents, which have slow reaction rate with CO2. The absorbents are triethanolamime (TEA), N-me...detailed

Hydrodenitrogenation of 2-methylpyridine and its intermediates 2-Methylpiperidine (cas 109-05-7) and tetrahydro-methylpyridine over sulfided NiMo/γ-Al2O308/21/2019

The reaction network and mechanism of the hydrodenitrogenation (HDN) of 2-methylpyridine and 2-methylpiperidine were studied at 280–340 °C and 1–3 MPa in the absence and presence of H2S over sulfided NiMo/γ-Al2O3. By the addition of 2-ethylpiperidine to the HDN of 2-methylpyridine and of 2-e...detailed

109-05-7Relevant articles and documents

Production of Piperidine and δ-Lactam Chemicals from Biomass-Derived Triacetic Acid Lactone

Chen, Bingfeng,Xie, Zhenbing,Peng, Fangfang,Li, Shaopeng,Yang, Junjuan,Wu, Tianbin,Fan, Honglei,Zhang, Zhaofu,Hou, Minqiang,Li, Shumu,Liu, Huizhen,Han, Buxing

, (2021)

Piperidine and δ-Lactam chemicals have wide application, which are currently produced from fossil resource in industry. Production of this kind of chemicals from lignocellulosic biomass is of great importance, but is challenging and the reported routes gi

-

Hornback et al.

, p. 1077 (1975)

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Organolanthanide-catalyzed hydroamination. A kinetic, mechanistic, and diastereoselectivity study of the cyclization of N-unprotected amino olefins

Gagné, Michel R.,Stern, Charlotte L.,Marks, Tobin J.

, p. 275 - 294 (1992)

This contribution reports the efficient, regiospecific Cp'2LnR [Cp' = η5-Me5C5; R = H, CH(TMS)2,η3-C3H5, N(TMS)2; Ln = La, Nd, Sm, Y, Lu]-catalyzed hydroamination/cyclization of the amino olefins H2NCHR1R2CH=CH2 to yield the corresponding heterocycles HNCH(R1)R2CHCH3, where R1, R2, Nt (turnover frequency, h-1), °C: H, (CH2)2, 140, 60 °C; H, CMe2CH2, 95, 25 °C; H, (CH2)3, 5, 60 °C; CH3, (CH2)2, 45, 25 °C; H, CH(Me)CH2, 38, 25 °C; and o-C6H4, CH2, 13, 80 °C. In addition, Me2Si(Me4C5)2NdCH(TMS)2 effects the cyclization of CH3HN(CH2)3CH=CH2 and H2NCH2CMe2(CH2) 3CH=CH2 with Nt = 11 h-1 (25 °C) and 0.3 h-1 (60 °C), respectively. Reactions are zero-order in substrate over 3 or more half-lives, and for the cyclization of HvN(CH2)3CH=CH2 by catalyst precursor Cp'2LaCH(TMS)2, ΔH? = 12.7 (1.4) kcal mol-1 and ΔS? = -27 (5) eu. Kinetic isotope effects (kH/kD) of 2.7 (4) (60 °C), 5.2 (8) (25 °C), and 4.1 (8) (25 °C) are observed for the Cp'2LaCH(TMS)2-induced cyclizations of D2N(CH2)3CH=CH2, D2NCH(C-H3)(CH2)2CH=CH2, and D2NCH2C(CH3)2CH 2CH=CH2, respectively. Cyclization yields the corresponding DNCH-(R1)R2CHCH2D isotopomers exclusively. Cyclization of H2NCH2C(CH3)2CH 2CH=CH2 by catalyst precursor Cp'2LaCH(TMS)2 exhibits the solvent effect, ktoluene/kTHF = 5.3 (5). The complexes Cp'2LnNHR(H2NR) (Ln = La, R = CH3, CH2CH3; Ln = Nd, R = CH2CH3) and Cp'2LaNCH(CH3)CH2CR2CH 2(HNCH(CH3)CH2CR2CH2) (R = H, CH3) were synthesized to model species in the catalytic cycle. Crystallographic data for Cp'2LaNHCH3(H2NCH3) at -120 °C were as follows: P21, Z = 4, a = 19.901 (4) A?, b = 11.695 (3) A?, c = 20.202 (3) A, β- 97.95 (2)°, and R(F) = 0.049 for 3296 independent reflections with I > 2.58σ(I). Two independent molecules crystallize per unit cell with average La-NHCH3 and La←NH2CH3 bond distances of 2.31 (1) and 2.70 (1) A?, respectively. The two molecules differ slightly in relative orientations of the NCH2 groups. The amine-amido complexes undergo rapid intramolecular proton transfer between amine and amido ligands (Δ? ≈ 12.4 ± 0.5 kcal mol-1). Intermolecular exchange with free amine is rapid on the NMR time scale at -80 °C. The ordering of precatalyst activities, (Cp'2LaCH(TMS)2 > Cp'2mCH(TMS)2 > Cp'2LuCH(TMS)2; Et2Si(C5H4)-(Me4C 5)LuCH(TMS)2 > Me2Si(Me4C5)2LuCH(TMS)2 > Cp'2LuCH(TMS)2) accords with known olefin insertion reactivities. Diastereoselection in H2NCH(CH3)(CH2)2CH=CH2 (5) cyclization depends on both lanthanide and ancillary ligation. Final 2,5-dimethylpyrrolidine transtcis ratios in LnLnR-catalyzed reactions for Ln, Ln, trans:cis, °C are as follows: Cp'2, La, 3:2, 50 °C; Cp'2, La, 5:1, 25 °C; Cp'2, La, 8:1, 0 °C; Cp'2, Nd, 1:1.25, 25 °C; Cp'2, Sm, 1:1.25, 25 °C; Cp'2, Y, 8:1, 25 °C; Me2Si(Me4C5)2, Y, 3:1, 25 °C; Et2Si(H4C5)(Me4C5), Y, 18:1, 25 °C; Et2Si(H4C5)(Me4C5), Lu, 4:1, 25 °C. For the Cp'2LaCH(TMS)2-catalyzed case, the trans:cis ratio is also dependent on the extent of conversion and initial substrate:catalyst ratio. In contrast to 5, 5d2 exhibits low diastereoselectivity which is independent of conversion. In the presence of 3 equiv of n-propylamine, the Cp'2LaCH(TMS)2-catalyzed cyclization of 5 affords a ≥50:1 trans:cis product ratio. Mechanistic evidence suggests that olefin insertion into the Ln-N bond of the amine-amido complexes is turnover-limiting and is followed by a rapid protonolysis of the resulting Ln-C bond. The proposed catalytic mechanism invokes parallel manifolds, with one manifold populated at high amine concentrations exhibiting high diastereoselectivity in the cyclization of 5, and with the second, favored at low substrate concentrations, exhibiting lower diastereoselectivity. The catalyst at high amine concentrations is postulated to be a Ln(amido)(amine)2 complex.

Rigid NON-donor pincer ligand complexes of lutetium and lanthanum: Synthesis and hydroamination catalysis

Motolko, Kelly S. A.,Emslie, David J. H.,Britten, James F.

, p. 27938 - 27945 (2017)

Reaction of H2XN2 {4,5-bis(2,4,6-triisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylxanthene} with [Lu(CH2SiMe3)3(THF)2], and crystallization from O(SiMe3)2, yielded [(XN2)Lu(CH2SiMe3)(THF)]·(O(SiMe3)2)1.5 (1·(O(SiMe3)2)1.5). Lanthanum complexes of the XN2 dianion were also prepared by salt metathesis; treatment of H2XN2 with excess KH in DME produced the dipotassium salt, [K2(XN2)(DME)x] (x = 2-2.5), and subsequent reaction with [LaCl3(THF)3] afforded [{(XN2)LaCl(THF)}x]·(O(SiMe3)2)0.25x (2·(O(SiMe3)2)0.25x; x = 1 or 2) after crystallization from O(SiMe3)2. Compound 2 reacted with two equivalents of LiCH2SiMe3, to form the dialkyl-'ate' complex, [Li(THF)x][(XN2)La(CH2SiMe3)2]·Toluene·LiCl (3·toluene·LiCl; x = 3). Both 1 and 3 (x = 4) were structurally characterized, and were evaluated as catalysts for intramolecular hydroamination; while 3 showed poor activity, 1 is highly active for both intramolecular hydroamination and more challenging intermolecular hydroamination. Reactions with unsymmetrical alkenes yielded Markovnikov products, and the activity of 1 surpassed that of the previously reported yttrium analogue in the reaction of diphenylacetylene with 4-tert-butylbenzylamine.

Yttrium and Aluminum Alkyl Complexes of a Rigid Bis-Anilido NON-Donor Ligand: Synthesis and Hydroamination Catalysis

Motolko, Kelly S. A.,Emslie, David J. H.,Jenkins, Hilary A.

, p. 1601 - 1608 (2017)

The palladium-catalyzed coupling of 4,5-dibromo-2,7-di-tert-butyl-9,9-dimethylxanthene (XBr2) with 2 equiv of 2,4,6-triisopropylaniline afforded the proligand 4,5-bis(2,4,6-triisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylxanthene (H2XN2), and reaction of H2XN2 with [Y(CH2SiMe2R)3(THF)2] (R = Me, Ph) produced the monoalkyl yttrium complexes [(XN2)Y(CH2SiMe2R)(THF)] (R = Me (1a), Ph (1b)). Neutral 1a showed near-zero ethylene polymerization activity (1 atm, 20 and 80 °C), and in the presence of AlMe3, 1a converted to [(XN2)Y{(μ-Me)2AlMe2}(THF)] (2). Compound 2 is thermally robust, and transfer of the XN2 ligand from yttrium to aluminum was not observed even at elevated temperatures. However, [(XN2)AlMe] (3) was accessible via the reaction of H2XN2 with AlMe3, demonstrating the ability of the wide-bite-angle XN2 ligand to coordinate to much smaller aluminum(III). Neutral 1a proved to be highly active for both intra- and intermolecular hydroamination with various substrates, yielding Markovnikov products in the intermolecular hydroamination reactions with 1-octene.

On the role of β hydrogen atoms in the hydrodenitrogenation of 2-methylpyridine and 2-methylpiperidine

Prins,Egorova,Zhao,Kukula

, p. 263 - 271 (2002)

Heterocyclic compounds like pyridine, quinoline, and acridine are the main nitrogen-containing compounds in oil. They are removed by HDN in a hydrotreating process in which gasoline or gas oil is treated with hydrogen over a metal sulfide catalyst. The HD

-

Jones,Lindsey

, p. 3261,3264 (1952)

-

Mutual influence of the HDS of dibenzothiophene and HDN of 2-methylpyridine

Egorova, Marina,Prins, Roel

, p. 11 - 19 (2004)

The influence of 2-methylpyridine and 2-methylpiperidine on the hydrodesulfurization of dibenzothiophene (DBT) and the effect of DBT on the hydrodenitrogenation of 2-methylpyridine and 2-methylpiperidine were studied over a sulfided NiMo/Al2O3 catalyst at 5 MPa, 35 kPa H2S, and 300 and 340°C. Both N-containing molecules strongly suppressed the hydrogenation pathway of the hydrodesulfurization of DBT and inhibited the direct desulfurization route at both reaction temperatures. The inhibitory effect on the direct desulfurization was stronger for 2-methylpyridine than for 2-methylpiperidine. H2S promoted the hydrogenation of 2-methylpyridine up to 10 kPa and inhibited it at higher partial pressures. H2S had a positive influence on the hydrodenitrogenation conversions of 2-methylpiperidine and 2-methylpyridine. DBT had a negative effect on the hydrogenation of 2-methylpyridine, but did not influence the C-N bond cleavage of 2-methylpiperidine. Therefore, C-N and C-S bond breaking takes place at different active sites, whereas the hydrogenation sites for N- and S-containing molecules may be the same.

Highly economical and direct amination of sp3carbon using low-cost nickel pincer catalyst

Brandt, Andrew,Rangumagar, Ambar B.,Szwedo, Peter,Wayland, Hunter A.,Parnell, Charlette M.,Munshi, Pradip,Ghosh, Anindya

, p. 1862 - 1874 (2021/01/20)

Developing more efficient routes to achieve C-N bond coupling is of great importance to industries ranging from products in pharmaceuticals and fertilizers to biomedical technologies and next-generation electroactive materials. Over the past decade, improvements in catalyst design have moved synthesis away from expensive metals to newer inexpensive C-N cross-coupling approaches via direct amine alkylation. For the first time, we report the use of an amide-based nickel pincer catalyst (1) for direct alkylation of amines via activation of sp3 C-H bonds. The reaction was accomplished using a 0.2 mol% catalyst and no additional activating agents other than the base. Upon optimization, it was determined that the ideal reaction conditions involved solvent dimethyl sulfoxide at 110 °C for 3 h. The catalyst demonstrated excellent reactivity in the formation of various imines, intramolecularly cyclized amines, and substituted amines with a turnover number (TON) as high as 183. Depending on the base used for the reaction and the starting amines, the catalyst demonstrated high selectivity towards the product formation. The exploration into the mechanism and kinetics of the reaction pathway suggested the C-H activation as the rate-limiting step, with the reaction second-order overall, holding first-order behavior towards the catalyst and toluene substrate.

Method for regulating and controlling catalytic hydrogenation reaction of pyridine derivative with redox potential

-

Paragraph 0052-0059, (2019/05/08)

The invention discloses a method for regulating and controlling catalytic hydrogenation reactions of a pyridine derivative with redox potential. On the basis of data such as redox potential (ORP) andcatalytic hydrogenation reaction process of the pyridine derivative in different medium systems, a scheme that the catalytic hydrogenation reaction of the pyridine derivative is promoted by improvingpyridine derivative ORP with an acid water solution is proposed. As the catalytic hydrogenation reactions of the pyridine derivative are instructed with ORP data, the testing period is shortened, meanwhile, by adopting the process, the pressure of hydrogenation reactions can be reduced, a piperidine product has the advantages of being high in purity, convenient in aftertreatment, and the like, andthus great instruction significances can be achieved for industrial development of the pyridine derivative.

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