102-53-4

Basic information

• Product Name: Bis(diethylamino)methane
• Synonyms: Bis(diethylamino)methane;N,N,N',N'-Tetraethyldiaminomethane;N,N'-Methylenebisdiethylamine;TETRAETHYLMETHYLENEDIAMINE;N,N,N',N'-TETRAETHYLMETHANEDIAMINE;N,N,N',N'-TETRAETHYLMETHYLENEDIAMINE;Methylenebis(diethylamine)
• CAS NO: 102-53-4
• Molecular Formula: C₉H₂₂N₂
• Molecular Weight: 158.28
• EINECS: 203-038-8
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines
• Mol File: 102-53-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 37.5°C (estimate)
• Boiling Point: 166-169 °C(lit.)
• Flash Point: 108 °F
• Appearance: /Liquid
• Density: 0.811 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.426(lit.)
• PKA: 7.85±0.50(Predicted)
• CAS DataBase Reference: Bis(diethylamino)methane(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(diethylamino)methane(102-53-4)
• EPA Substance Registry System: Bis(diethylamino)methane(102-53-4)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 16-26-27-36/37/39-45
• RIDADR: UN 2734 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 102-53-4(Hazardous Substances Data)

Usage

General Description

Bis(diethylamino)methane, also known as N,N'-Diethylethylenediamine or simply DBU, is a powerful organic base commonly used in synthetic chemistry and chemical research. Its strong basicity and steric hindrance properties make it valuable in various chemical reactions, particularly for deprotonation, condensation, and elimination reactions. DBU finds applications in the synthesis of pharmaceuticals, polymers, and specialty chemicals, as well as in catalysis and as a reagent in organic transformations, contributing to advancements in the field of organic chemistry.

Uses

N,N,N′,N′-Tetraethylmethanediamine has been used to study the tertiary amine catalytic activities in the reaction of phenyl isocyanate with 1-butanol in toluene.

Upstream product

• 80202-61-5 N-<(trimethylsiloxy)methyl>diethylamine 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 1353053-97-0 triethylsiloxymethyl-N,N-dimethylamine 
• 109-89-7 diethylamine 
• 50-00-0 formaldehyd 
• 2985-33-3 monoethyl methylmalonate 
• 7732-18-5 water 
• 69923-74-6 monoethyl DL-ethyl-malonate 
• 5888-29-9 diethyl(methoxymethyl)amine 
• 274-26-0 1,3-benzoxathiole 
• 3553-86-4 (dibutylamino)trimethylsilane 
• 15931-59-6 diethylamino-methanol 
• 274-09-9 Methylenedioxybenzene 
• 26198-79-8 (E)-1,3,7-octatriene 

Downstream Products

• 636-70-4 triethylamine hydrobromide 
• 105-18-0 N,N,N',N'-Tetraethyl-1,4-diaminobut-2-yne 
• 616-39-7 N,N-diethylnmethylamine 
• 6022-10-2 (diethylamino)triethylsilane 
• 154351-17-4 2-phenyl-1,3-bis(diethylaminomethyl)-5,6-benzo-1,3,2-diazaphosphepane 
• 995-14-2 diethyl <(diethylamino)methyl>phosphonate 
• 6631-70-5 N-ethyl-N-(propan-2-ylsulfanylmethyl)ethanamine 
• 13865-52-6 N-ethyl-N-(phenylsulfanylmethyl)ethanamine 
• 18975-51-4 diphenyl(N,N-diethylaminomethyl)phosphine oxide 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 140704-83-2 2,7-bis<(diethylamino)methyl>-2,7-diphenyl-3,8-dioxa-1,6-diaza-2λ⁵,7λ⁵-diphosphatricyclo<5.3.0.0^2,6>decane 
• 69084-00-0 2-(N,N-diethylaminomethyl)-4,6-dimethylphenol 
• 33935-31-8 chloro(N,N-diethylamino)diphenylsilane 
• 52853-18-6 N,N-diethyl(methylene)ammonium chloride 

Relevant articles and documents

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

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.

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A new procedure for preparing perfluoroalkoxypropanoic acid fluorides

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

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

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