Dichloro(N,N,N',N'-tetramethylethylenediamine)zinc

Base Information

• Chemical Name: Dichloro(N,N,N',N'-tetramethylethylenediamine)zinc
• CAS No.: 28308-00-1
• Molecular Formula: C6H16 Cl2 N2 Zn
• Molecular Weight: 252.502
• Hs Code.: 29349990
• European Community (EC) Number: 628-904-6
• DSSTox Substance ID: DTXSID40421952
• Mol file: 28308-00-1.mol

Synonyms:28308-00-1;Dichloro(N,N,N',N'-tetramethylethylenediamine)zinc;zncl2(tmeda);ZnCl2-TMEDA;dichlorozinc;N,N,N',N'-tetramethylethane-1,2-diamine;SCHEMBL4383415;DTXSID40421952;FT-0638774;EN300-25685243;[2-(dimethylamino)ethyl]dimethylamine;DICHLORO(N,N,N,N-TETRAMETHYLETHYLENEDIAMINE)ZINC;Zinc, dichloro(N,N,N',N'-tetramethylethylenediamine)-;Dichloro(N,N,N',N'-tetramethylethylenediamine)zinc, 98%;DICHLORO(N,N,N,N-TETRAMETHYLETHYLENE-D IAMINE)ZINC, 98%;N~1~,N~1~,N~2~,N~2~-Tetramethylethane-1,2-diamine--dichlorozinc (1/1);Zinc, dichloro(N,N,N',N'-tetramethyl-1,2-ethanediamine-N,N')-, (T-4)-

Chemical Property of Dichloro(N,N,N',N'-tetramethylethylenediamine)zinc

Chemical Property:

• Melting Point: 176-178 °C(lit.)
• Boiling Point: 121oC at 760 mmHg
• Flash Point: 10oC
• PSA: 6.48000
• LogP: 1.48610
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 249.998196
• Heavy Atom Count: 11
• Complexity: 45.2

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dichloro(N,N,N'',N''-tetramethylethylenediamine)zinc(II) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCN(C)C.Cl[Zn]Cl
• General Description: **Dichloro(N,N,N',N'-tetramethylethylenediamine)zinc** is a charge-transfer complex formed between tetramethylethylenediamine (TMEDA) and zinc chloride (ZnCl₂), with a 1:1 or 1:2 stoichiometry depending on the acceptor behavior. It exhibits distinct electrical properties, including measurable AC conductivity and dielectric coefficients, and has been studied for its potential biological activity against bacterial and fungal strains. The complex's structural and electronic characteristics influence its positron annihilation lifetime parameters, which correlate with molecular weight and reactivity.

Technology Process of Dichloro(N,N,N',N'-tetramethylethylenediamine)zinc

There total 5 articles about Dichloro(N,N,N',N'-tetramethylethylenediamine)zinc which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

N,N,N,N,-tetramethylethylenediamine (110-18-9) + zinc(II) chloride (7646-85-7,24359-56-6) → zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) (28308-00-1)

Guidance literature:

In ethanol; at 25 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.202101256

Reference yield: 69.0%

{TaCl2(2,6-(Me2NCH2)2C6H3)(CtBu)ZnCl} → zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) (28308-00-1) + TaCl(C6H3(CH2N(CH3)2)(CH2N(CH3)CH2))(CHC(CH3)3)

Guidance literature:

With Me₂NC₂H₄NMe₂; In benzene; under N2; to a soln. of the complex in benzene was added Me2NC2H4NMe2 at 62°C (30 min), stirred at room temp. for 18 h; solvent was removed in vac., extd. with hexane, solvent was removed in vac., crystn. from hexane;;

Reference yield: 20.0%

di-μ-chlorobis-[[2-(dimethylamino)methyl]phenyl-C,N]dipalladium(II) + {TaCl2(2,6-(Me2NCH2)2C6H3)(CtBu)ZnCl} → zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) (28308-00-1) + TaCl2(C6H4CH2N(CH3)2)(C(C(CH3)3)C6H3(CH2N(CH3)2)2)

Guidance literature:

With Me₂NC₂H₄NMe₂; In tetrahydrofuran; under N2; the Pd complex was suspd. in a stirred soln. of the TaZn compound in THF, Me2NC2H4NMe2 was added, stirred for 15 h;

upstream raw materials:

N,N,N,N,-tetramethylethylenediamine

zinc(II) chloride

(N,N,N′,N′-tetramethylethylenediamine)zinc hexasulfide

octasulfur dichloride

Downstream raw materials:

((CH₃)2C₆H₅Si)3Zn^(1-)*Li⁽¹⁺⁾=((CH₃)2C₆H₅Si)3ZnLi

C₁₈H₁₆Cl₂SiZn₂

Refernces

Computed CH acidity of biaryl compounds and their deprotonative metalation by using a mixed lithium/Zinc-TMP base

10.1002/chem.201300552

This research aims to develop synthetic methods for biaryl compounds, which are important in medicinal chemistry and materials science. The study explores the deprotonative metalation of various aromatic compounds using a mixed lithium/zinc-TMP (2,2,6,6-tetramethylpiperidino) base, followed by iodolysis and palladium-catalyzed cross-coupling reactions to synthesize a range of biaryl derivatives. ZnCl2·TMEDA (Dichloro(N,N,N',N'-tetramethylethylenediamine)zinc) plays a crucial role in the deprotonative metalation process. Specifically, it is used in combination with Li(TMP) (lithium 2,2,6,6-tetramethylpiperidino) to form an effective base for the deprotonation of various aromatic compounds. The researchers also used arylboronic acids and palladium catalysts for the cross-coupling reactions. The study concludes that the regioselectivity of the deprotometalation reactions is influenced by both the CH acidities of the substrates and the coordinating abilities of nearby atoms, such as nitrogen in azines. The calculated pKa values in THF solution using DFT B3LYP method provided insights into the acidity/regioselectivity relationship. The findings highlight the potential of the lithium/zinc-TMP base for functionalizing biaryl compounds, including sensitive heterocycles, and demonstrate its effectiveness in directing metalation reactions to specific sites.

N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides

10.1039/c1ob05267e

The research investigates the deprotonative metallation of N-aryl and N-heteroaryl pyrazoles using a mixed lithium–zinc base derived from ZnCl2·TMEDA (Zinc chloride N,N,N',N'-tetramethylethylenediamine complex) and LiTMP (Lithium 2,2,6,6-tetramethylpiperidide). The study explores the impact of various substituents on the pyrazole ring's CH acidity and how these influence the metallation outcomes. Through experimental and computational methods, including Density Functional Theory (DFT) calculations, the researchers determined the CH acidities of the substrates in both the gas phase and THF solution. They found that electron-withdrawing groups enhance CH acidity, favoring deprotonation, while electron-donating groups have the opposite effect. The results showed that the most acidic site on the pyrazole ring is typically the 5 position, and the study identified conditions under which mono-, di-, or tri-iodides could be selectively obtained.