Bis(dimethylamino)methane

{{Chembox

| ImageFile = Me2NCH2NMe2.svg

| ImageSize =

| ImageAlt =

| IUPACName = N,N,N′,N′-Tetramethylmethanediamine

| OtherNames = N,N,N′,N′-Tetramethylmethylenediamine

| Section1 = {{Chembox Identifiers

| CASNo = 51-80-9

| ChemSpiderID = 5624

| PubChem = 5829

| EC_number = 200-124-7

| UNNumber = 1993

| UNII = Z870I525KS

| StdInChI=1S/C5H14N2/c1-6(2)5-7(3)4/h5H2,1-4H3

| StdInChIKey = VGIVLIHKENZQHQ-UHFFFAOYSA-N

| SMILES = CN(C)CN(C)C

}}

| Section2 = {{Chembox Properties

| C = 5|H=14|N=2

| MolarMass =

| Appearance = colorless liquid

| Density = 0.749 g/cm³

| MeltingPtC = -12

| BoilingPtC = 85

| Solubility = }}

| Section3 = {{Chembox Hazards

| GHSPictograms = {{GHS02}}{{GHS05}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|225|314}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|370+378|403+235|405|501}}

| MainHazards =

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| AutoignitionPt = }}

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Bis(dimethylamino)methane is the organic compound with the formula [(CH₃)₂N]₂CH₂. It is classified as an aminal as well as a ditertiary amine, in fact the simplest. It is a colorless liquid that is widely available. It is prepared by the reaction of dimethylamine and formaldehyde:{{cite journal |doi=10.15227/orgsyn.059.0153|title=

Regioselective Mannich Condensation with Dimethyl(Methylene)ammonium Trifluoroacetate: 1-(Dimethylamino)-4-methyl-3-pentanone

|first1=Michel|last1=Gaudry|first2=Yves|last2=Jasor|first3=Trung Bui |last3=Khac|journal=Org. Synth.|year=1979|volume=59|page=153}}

: 2 (CH₃)₂NH + CH₂O → [(CH₃)₂N]₂CH₂ + H₂O

It is used for the dimethylaminomethylation reactions, the reaction being initiated by the addition of a strong, anhydrous acid:{{cite journal |journal=E-EROS Encyclopedia of Reagents for Organic Synthesis| title=Bis(dimethylamino)methane|doi=10.1002/047084289X.rb143|author=Allen J. Duplantier| date=2001| isbn=0471936235}}

: [(CH₃)₂N]₂CH₂ + H⁺ → (CH₃)₂NCH₂⁺ + (CH₃)₂NH

Bis(dimethylamino)methane, being a Lewis base, functions as a bidentate ligand.{{cite journal |doi=10.1002/chem.201600810 |title=Siloxymethylamines as Aminomethylation Reagents for Amines Leading to Labile Diaminomethanes That Can Be Trapped as Their [Mo(CO)₄] Complexes |date=2016 |last1=Sharma |first1=Hemant K. |last2=Gonzalez |first2=Paulina E. |last3=Craig |first3=Alexander L. |last4=Chakrabarty |first4=Sanchita |last5=Metta-Magaña |first5=Alejandro |last6=Pannell |first6=Keith H. |journal=Chemistry – A European Journal |volume=22 |issue=22 |pages=7363–7366 |pmid=27111263 }}