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N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE, also known as Tetramethylethylenediamine (TMEDA), is an organic compound with the chemical formula (C2H5)2NCH2CH2N(CH2C2H5)2. It is a colorless, high boiling liquid that is soluble in water and serves as a versatile reagent and catalyst in various chemical reactions due to its basic nature and ability to form complexes with metal ions.

102-53-4

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102-53-4 Usage

Uses

Used in Chemical Synthesis:
N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE is used as a reagent for facilitating various chemical reactions, such as the reaction of phenyl isocyanate with 1-butanol in toluene. It acts as a tertiary amine catalyst, enhancing the reaction rate and improving the overall efficiency of the process.
Used in Catalyst Industry:
N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE is used as a catalyst in the production of various chemicals, including pharmaceuticals, agrochemicals, and specialty chemicals. Its ability to form complexes with metal ions makes it a valuable component in homogeneous catalysis, where it can improve the selectivity and activity of the catalyst.
Used in Polymer Industry:
In the polymer industry, N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE is used as a curing agent for epoxy resins. It reacts with the epoxy groups to form cross-linked networks, resulting in improved mechanical properties and thermal stability of the final polymer product.
Used in Analytical Chemistry:
N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE is employed as a complexing agent in analytical chemistry for the determination of metal ions, particularly in titrations and spectrophotometric methods. Its ability to form stable complexes with metal ions allows for accurate and sensitive detection of trace metal concentrations in various samples.
Used in Environmental Applications:
N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE can be used in environmental applications for the removal of heavy metal ions from contaminated water and soil. Its complexing properties enable it to bind and sequester metal ions, facilitating their removal from the environment and reducing their potential impact on ecosystems and human health.

Uses

Used in Pharmaceutical Synthesis:
N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE is used as a synthetic reagent for the production of pharmaceuticals. Its strong basicity aids in various chemical reactions, such as deprotonation and condensation, which are essential for the synthesis of active pharmaceutical ingredients.
Used in Polymer Synthesis:
In the polymer industry, N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE is used as a catalyst and reagent for the synthesis of polymers. Its ability to promote specific reactions, such as elimination and condensation, contributes to the development of novel polymer materials with desired properties.
Used in Specialty Chemicals Production:
N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE is employed as a key component in the production of specialty chemicals. Its strong basicity and steric hindrance properties enable the synthesis of complex organic compounds with specific functionalities, which are valuable in various applications, such as agrochemicals, dyes, and fragrances.
Used in Catalysis:
In the field of catalysis, N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE is used as a catalyst to enhance the efficiency of chemical reactions. Its strong basicity and steric properties allow it to act as a Lewis base, facilitating the formation of reactive intermediates and improving the overall reaction rate.
Used in Organic Transformations:
N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE is utilized as a reagent in various organic transformations, such as the formation of imines, enamines, and other reactive intermediates. Its strong basicity and ability to stabilize charged species make it a valuable tool in organic synthesis, enabling the synthesis of complex organic molecules with high selectivity and yield.

Check Digit Verification of cas no

The CAS Registry Mumber 102-53-4 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 2 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 102-53:
(5*1)+(4*0)+(3*2)+(2*5)+(1*3)=24
24 % 10 = 4
So 102-53-4 is a valid CAS Registry Number.

102-53-4 Well-known Company Product Price

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  • Alfa Aesar

  • (11294)  N,N,N',N'-Tetraethylmethylenediamine, 98%   

  • 102-53-4

  • 5g

  • 465.0CNY

  • Detail
  • Alfa Aesar

  • (11294)  N,N,N',N'-Tetraethylmethylenediamine, 98%   

  • 102-53-4

  • 25g

  • 1716.0CNY

  • Detail
  • Alfa Aesar

  • (11294)  N,N,N',N'-Tetraethylmethylenediamine, 98%   

  • 102-53-4

  • 100g

  • 6862.0CNY

  • Detail
  • Aldrich

  • (127175)  N,N,N′,N′-Tetraethylmethanediamine  97%

  • 102-53-4

  • 127175-10G

  • 678.60CNY

  • Detail

102-53-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N,N',N'-tetraethylmethanediamine

1.2 Other means of identification

Product number -
Other names Bis(diethylamino)methane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:102-53-4 SDS

102-53-4Relevant academic research and scientific papers

Siloxymethylamines as Aminomethylation Reagents for Amines Leading to Labile Diaminomethanes That can be Trapped as Their [Mo(CO)4] Complexes

Sharma, Hemant K.,Gonzalez, Paulina E.,Craig, Alexander L.,Chakrabarty, Sanchita,Metta-Maga?a, Alejandro,Pannell, Keith H.

, p. 7363 - 7366 (2016)

Compound Et3SiOCH2NMe2 transfers Me2NCH2 to R2NH (R2=Et2, PhMe, [Cr(η6-C6H5)(CO)3]Me, PhH) to form previously unknown diaminomethanes, Me2NCH2NR2 and, in the case of R2=PhH, the triamine Me2NCH2N(Ph)CH2NMe2. The diaminomethanes exhibit an unreported disproportionation to a mixture of (R2N)2CH2, (Me2N)2CH2, and Me2NCH2NR2, which can be trapped as their [Mo(CO)4(diamine)] complexes. Whereas PhMeNCH2NMe2 is a labile material, the metal-substituted ([(η6-C6H5)Cr(CO)3]MeNCH2NMe2 is a stable material. The triamine Me2NCH2N(Ph)CH2NMe2 is unstable with respect to transformation to 1,3,5-triphenyltriazine, but is readily trapped as the bidentate-triamineMo(CO)4. All metal complexes were characterized by single-crystal X-ray diffraction.

A new procedure for preparing perfluoroalkoxypropanoic acid fluorides

Igumnov,Lekontseva,Shipigusev,Mukhametshin

, p. 435 - 437 (2005)

Condensation of perfluoro carboxylic acid fluorides with hexafluoropropene epoxide in the presence of N,N, N,N-tetraalkyldiaminomethanes was studied.

Method for preparing kakonein derivatives

-

Paragraph 0031-0032, (2017/03/17)

The invention discloses a puerarin derivative preparation method. Puerarin derivative has the structural formula as shown in the specification, and the puerarin derivative is obtained by that puerarin reacts with CH2(R)2, wherein R is a tertiary amine gene. The puerarin derivative preparation method is characterized in that reaction is carried out under hydrochloric acid catalysis. Compared with the prior art, the puerarin derivative preparation method is characterized in that the yield of a puerarin derivative product can be obviously improved after the class of reaction adopts hydrochloric acid catalysis.

Synthesis of amino sulfides in the presence of rare-earth and transition metal catalysts

Khairullina, R. R.,Akmanov, B. F.,Kunakova, R. V.,Ibragimov, A. G.

, p. 902 - 907,6 (2020/08/31)

Efficient procedures have been developed for the synthesis of amino sulfides by aminomethylation of thiols with higher geminal diamines, thiomethylation of secondary amines with N,N-dimethylaminomethyl sulfides, and decyclization of 1,3,6-oxadithiepane or

Synthesis, characterization, and anti-amoebic screening of core-modified 5,20-bis{2-{[(alkyl)(alkyl′)amino]methyl}ferrocen-1-yl}-10,15-diphenyl-21, 23-dithiaporphyrin (=1,1″-(10,15-diphenyl-21,23-dithiaporphine-5,20-diyl) bis[2-{[(alkyl)(alkyl′)amino]methyl}ferrocene]) derivatives

Bhat, Abdul R.,Bhat, Asif I.,Athar, Fareeda,Azam, Amir

experimental part, p. 1644 - 1656 (2009/10/16)

The synthesis of the first bis-ferrocenyl-substituted core-modified porphyrins, 5,20-bis{2-{[(alkyl)-(alkyl′)amino]methyl}ferrocen-1-yl}-10, 15-diphenyl-21,23-dithiaporphyrin derivatives 6a - 6j, via a multistep route is reported (Schemes 1, 2, and 4). The synthesis was carried out through acid-catalyzed (BF3 ? Et2O) condensation of 1,1″- [thiophene-2,5-diylbis(hydroxymethyl)]bis[2-{[(alkyl)(alkyl′)amino]methyl} ferrocenes] 4a - 4j with 2,2′-[thiophene-2,5-diylbis(phenylmethylene)] bis[1H-pyrrole] (5b) in presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (=4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile; DDQ). Characterization of the compounds was done at each step by means of various spectroscopic techniques. The final compounds were screened for in vitro anti-amoebic activity against the strain HM1:IMSS of E. histolytica (Table 2).

The generation of iminium ions using chlorosilanes and their reactions with electron rich aromatic heterocycles

Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.

, p. 2941 - 2958 (2007/10/03)

Dichlorodimethylsilane and trichloromethylsilane have been used to generate iminium ions from aminals and aminol ethers derived from secondary alkylamines, including glycine derivatives, in aprotic media which were shown to undergo reactions with electron rich aromatic heterocycles, including furan, to give mono-aminoalkylation products in good yields. Whereas chlorotrimethylsilane has been shown to generate iminium ions from aminol ethers, no evidence was adduced for the involvement of iminium ions using aminals. 2,5-Disubstitution of N-methylpyrrole was the major result in reactions of N-methylpyrrole with aminals in the presence of chlorotrimethylsilane where no build up of hydrogen chloride occurs and where chlorotrimethylsilane can function catalytically. Experimental results, including the use of bis(trimethylsilyl)acetamide as a proton scavenger, and some relative rate data, are presented that allow possible mechanisms to be evaluated.

Use of methylene chloride as a C1 unit in N,N-dialkylaminomethylation reaction

Souquet,Martens,Fleury

, p. 817 - 828 (2007/10/02)

Mannich products have been isolated in good yields with methylene chloride as a C1 unit, instead of formaldehyde. It is evidenced that, contrary to previous understanding, a high pressure procedure is not necessary required and that the methylene bisamines function as intermediates.

Photochemical Reactions of Trialkylammonio-N-diphenylphosphinoylimides: Rearrangement to N-Phosphinoyl Aminals and the Formation of Diphenylphosphinic Amide

Freeman, Sally,Harger, Martin J. P.

, p. 571 - 578 (2007/10/02)

The photolysis of the aminimide Ph2P(O)N--N+Me3 (1) in methanol gives the amide Ph2P(O)NH2 in high yield, but most of this is not formed from (1) directly via the nitrene; rather, it results from (solvolytic) decomposition of the phosphinoyl aminal Ph2P(O)NHCH2NMe2 (5) formed from (1) by a photochemical rearrangement.With Ph2P(O)N--N+Et3 the corresponding rearrangement product Ph2P(O)NHCHMeNEt2 (an ethylidene aminal) is not observed, but this is probably just a consequence of very rapid decomposition.Although substrates bearing both Me and Et groups on the ammonium N atom appear to form only the rearrangement product (a methylene aminal) that results form involvement of a Me group, the yield is reduced substantially relative to the yield of (5) from (1).The size of the reduction is consistent with an Et group participating in the rearrangement about twice as readily as a Me group, but the product (an ethylidene aminal) that results suffering (much) much more rapid decomposition to Ph2P(O)NH2.

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