tert-Butoxy bis(dimethylamino)methane

Base Information

• Chemical Name: tert-Butoxy bis(dimethylamino)methane
• CAS No.: 5815-08-7
• Molecular Formula: C9H22 N2 O
• Molecular Weight: 174.286
• Hs Code.: 2922199090
• European Community (EC) Number: 227-383-9
• UNII: JEJ0U558F7
• DSSTox Substance ID: DTXSID00206888
• Nikkaji Number: J218.073A
• Wikipedia: Tert-Butoxybis(dimethylamino)methane
• Wikidata: Q27281472
• Mol file: 5815-08-7.mol

Synonyms:5815-08-7;tert-Butoxy bis(dimethylamino)methane;Tert-Butoxybis(Dimethylamino)Methane;Bredereck's reagent;1-tert-butoxy-n,n,n',n'-tetramethylmethanediamine;[(tert-butoxy)(dimethylamino)methyl]dimethylamine;BREDERECK REAGENT;N,N,N',N'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine;MFCD00042858;JEJ0U558F7;Brederecks reagent;bis(dimethylamino)-t-butoxymethane;1-(1,1-DIMETHYLETHOXY)-N,N,N',N'-TETRAMETHYL-METHANEDIAMINE;1-tert-Butoxy-N,N,N',N'-tetramethyl-methanediamine;bis(dimethylamino)-tert-butyloxymethane;METHANEDIAMINE, 1-(1,1-DIMETHYLETHOXY)-N,N,N',N'-TETRAMETHYL-;tert-butoxy-N,N,N',N'-tetramethylmethanediamine;1-tert-Butoxy-N,N,N',N'-tetramethylmethylenediamine;tert-butoxybis-(dimethylamino)methane;tert-butoxybis-[dimethylamino]methane;Brederick's reagent;EINECS 227-383-9;Tert-butoxy-bis(dimethylamino)methane;tBuOCH(NMe2)2;(Me2N)2CHOt-Bu;t-BuOCH(NMe2)2;UNII-JEJ0U558F7;SCHEMBL62598;tert-butoxybisdimethylaminomethane;bis(dimethyamino)-t-butoxymethane;t-Butoxy-bis dimethylaminomethane;t-Butoxy-bis-dimethylaminomethane;BREDERECK'S REAGENT [MI];DTXSID00206888;bisdimethylamino-tert-butoxymethane;t-butoxy bis(dimethylamino)methane;t-butoxy-bis(dimethylamino)methane;t-butoxybis (dimethylamino)methane;t-butoxybis(dimethyl amino)methane;t-butoxybis(dimethylamino) methane;t-butoxybis(dimethylamino)-methane;tert-butoxy bisdimethylaminomethane;tertbutoxybis(dimethylamino)methane;AMY19938;BCP19463;bis-(dimethylamino)-t-butoxymethane;bis-dimethylaminotert.-butoxymethane;t-butoxy-bis(dimethylamino) methane;tert.butoxy-bis(dimethylamino)methan;BBL103828;bis(dimethylamino)-tert-butoxymethane;bis(dimethylamino)tert.-butoxymethane;bis-dimethylamino-tert.-butoxymethane;STL557638;t-butoxy-bis-(dimethylamino)-methane;tert-butoxy bis(dimethylamine)methane;tert-butoxybis (dimethylamino)methane;tert-butoxybis(dimethylamino) methane;tert-Butyloxybis(dimethylamino)methane;AKOS015850672;bis(dimethylamino)-tert.-butoxymethane;bis-(dimethylamino)-tert-butoxymethane;tert- Butoxy bis(dimethylamino)methane;tert-butoxy-bis(dimethylamino)-methane;tert-butoxybis (dimethylamino) methane;tert.-butoxy-bis(dimethylamino)methane;AB01945;T-BUTOXYBIS(DIMETHYLAMINO)METHANE;tert-butoxy-bis (dimethylamino) methane;tert.-butoxy-bis-(dimethylamino)methane;tert.-butoxy-bis-(dimethylamino)-methane;AS-18941;bis(dimethylamino)methyl tertiary-butyl ether;CS-0006022;TERT-BUTOXY-BIS(DIMETHYLAMINE)METHANE;tert-Butoxy-bis(dimethylamino)methane, Tech.;TERT-BUTOXYMETHYLENEBIS(DIMETHYLAMINE);EN300-80797;tert-Butoxy bis(dimethylamino)methane, technical;1-(t-butoxy)-N,N,N',N'-tetramethylmethanediamine;C-tert-butoxy-N,N,N',N'-tetramethylmethanediamine;tert-butoxy-N,N,N',N'-tetra-methyl-methanediamine;tert-butoxy-N,N,N',N'-tetramethyl-methanediamine;1-(tert-Butoxy)-N,N,N',N'-tetramethylmethanediamin;C-tert-Butoxy-N,N,N',N'-tetramethyl-methanediamine;1-(tert-Butoxy)-N,N,N',N'-tetramethylmethanediamine;N-[tert-butoxy(dimethylamino)methyl]-N,N-dimethylamine;Q27281472;F0001-1518;{(dimethylamino)[(1,1-dimethylethyl)oxy]methyl}dimethylamine;1-(1,1-dimethylethoxy)-N,N, N', N'-tetramethyl-methanediamine;1-(1,1-DIMETHYLETHOXY)-N,N,N',N'-TETRAMETHYLMETHANEDIAMINE

Chemical Property of tert-Butoxy bis(dimethylamino)methane

Chemical Property:

• Appearance/Colour: Clear pale yellow liquid
• Vapor Pressure: 1.07mmHg at 25°C
• Refractive Index: n20/D 1.422(lit.)
• Boiling Point: 50-55 °C15 mm Hg(lit.)
• PKA: 5.46±0.38(Predicted)
• Flash Point: 41 ºC
• PSA: 15.71000
• Density: 0.844
• LogP: 1.20830
• Storage Temp.: Freezer (-20°C)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 174.173213330
• Heavy Atom Count: 12
• Complexity: 119

Purity/Quality:

99%, ^*data from raw suppliers

1-(1,1-Dimethylethoxy)-N,N,N'',N''-tetramethyl-methanediamine(containsTris(dimethylamino)MethaneandN,N-DimethylformamideDi-tert-butylAcetal)(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(N(C)C)N(C)C
• Uses: Reactant for:? ;Preparation of pyrroloquinazolines as photochemotherapeutic agents1? ;Enanatioslective formal synthesis of the Cinchona alkaloid quinine via stereoselective intermolecular radical addition2? ;Synthesis of camptothecin via intramolecular isomuenchnone cycloaddition reaction3? ;Aminomethylenation reactions4 Mild enamination reagent; catalyst in ring-opening polymerization reactions. Reactant for:Preparation of pyrroloquinazolines as photochemotherapeutic agentsEnanatioslective formal synthesis of the Cinchona alkaloid quinine via stereoselective intermolecular radical additionSynthesis of camptothecin via intramolecular isomuenchnone cycloaddition reactionAminomethylenation reactions

Technology Process of tert-Butoxy bis(dimethylamino)methane

There total 3 articles about tert-Butoxy bis(dimethylamino)methane 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:

potassium tert-butylate (865-47-4) + N,N,N',N'-tetramethylformamidinium hexafluorophosphate → tris(dimethylamino)methane (5762-56-1) + tert-Butoxybis(dimethylamino)methane (5815-08-7) + N,N-dimethylformamide di-tert-butyl acetal (36805-97-7)

Guidance literature:

In tetrahydrofuran; at 50 ℃; for 1h;

Reference yield:

potassium tert-butylate (865-47-4) + N,N,N',N'-tetramethylformamidinium methyl sulfate (2013-91-4) → tris(dimethylamino)methane (5762-56-1) + tert-Butoxybis(dimethylamino)methane (5815-08-7) + N,N-dimethylformamide di-tert-butyl acetal (36805-97-7)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 1h;

Reference yield:

potassium tert-butylate (865-47-4) + N,N,N',N'-Tetramethylformamidinium-(p-toluolsulfonat) (3218-35-7) → tris(dimethylamino)methane (5762-56-1) + tert-Butoxybis(dimethylamino)methane (5815-08-7) + N,N-dimethylformamide di-tert-butyl acetal (36805-97-7)

Guidance literature:

In tetrahydrofuran; at 50 ℃; for 1h;

upstream raw materials:

potassium tert-butylate

N,N,N',N'-tetramethylformamidinium methyl sulfate

N,N,N',N'-Tetramethylformamidinium-(p-toluolsulfonat)

Downstream raw materials:

3-(Dimethylamino)-1,2-diphenyl-2-propen-1-on

3,3-Bis-dimethylamino-1--propin-(1)

ω-Dimethylamino-4-methoxycarbonyl-styrol

2-(2-Dimethylamino-vinyl)-benzoxazol

Refernces

An efficient and practical synthesis of 2,4-substituted pyrido[4,3-d]pyrimidin-5(6H)-ones

10.1016/j.tetlet.2019.151312

Xinrong Tian et al. describe an efficient synthesis route for 2,4-substituted pyrido[4,3-d]pyrimidin-5(6H)-ones, which are important scaffolds in biologically active compounds. The synthesis involves the acid-promoted cyclization of cyano enamine 15 to produce 2,4-bis-thiomethyl pyrido[4,3-d]pyrimidin-5(6H)-one 17 as a key intermediate. The 4-methylthio group in 17 can be selectively displaced by various anilines under acidic conditions, and the 2-methylthio group can be oxidized and subsequently substituted by different amines. This approach allows for the synthesis of a variety of 2,4-disubstituted pyrido[4,3-d]pyrimidin-5(6H)-ones with high functional group tolerance and flexibility for late-stage modifications. The study also highlights the use of tert-butoxy bis(dimethylamino)methane (Bredereck's reagent) as a more functional-group tolerant alternative to dimethylformamide dimethylacetal (DMF-DMA) for enamine formation.

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