[(dimethylamino)methyl]dimethylamine

• ChemBase ID: 111441
• Molecular Formular: C5H14N2
• Molecular Mass: 102.17806
• Monoisotopic Mass: 102.11569846
• SMILES: CN(C)CN(C)C
• Canonical SMILES: CN(CN(C)C)C
• InChI: InChI=1S/C5H14N2/c1-6(2)5-7(3)4/h5H2,1-4H3
• InChIKey: VGIVLIHKENZQHQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(dimethylamino)methyl]dimethylamine
• IUPAC Traditional name: [(dimethylamino)methyl]dimethylamine
• Synonyms: N,N,N′,N′-Tetramethylmethanediamine; Bis(dimethylamino)methane; N,N,N′,N′-Tetramethyldiaminomethane; bis(DIMETHYLAMINO METHANE); N,N,N'N'-Tetramethyldiaminomethane; N,N,N',N'-Tetramethylmethylenediamine; N,N,N',N'-tetramethylmethanediamine; 双(二甲氨基)甲烷; 四甲基甲烷二胺; N,N,N′,N′-四甲基甲二胺; N,N,N',N'-四甲基亚甲二胺

Database IDs

• CAS Number: 51-80-9
• EC Number: 200-124-7
• MDL Number: MFCD00008328
• Beilstein Number: 1731946
• PubChem SID: 24900015; 162096616; 24848864
• PubChem CID: 5829

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.8240026
• LogD (pH = 7.4): -0.10955587
• Log P: 0.31891492
• Molar Refractivity: 32.8167 cm^3
• Polarizability: 13.012255 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -55°C
• Boiling Point: 83-85°C; 85 °C(lit.); 85°C
• Flash Point: -11 °C; 12.2 °F; -12°C(10°F)
• Density: 0.749; 0.749 g/mL at 25 °C(lit.)
• Refractive Index: 1.4010; n20/D 1.401; n20/D 1.401(lit.)

Safety Information

• RTECS: PA6700000
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2733; UN2733
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-34; R:11
• Safety Statements: 16-26-36/37/39-45; 20-26-36/37/39-45-60; S:9-16-29
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314; H225-H314-H318
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2733 3/PG 2

Product Information

• Purity: ≥97.0% (GC); 99%
• Grade: purum
• Impurities: ≤2% water
• Linear Formula: (CH3)2NCH2N(CH3)2

DETAILS

MP Biomedicals - 05219187

MP Biomedicals Rare Chemical collection

Sigma Aldrich - T21407

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 14790

Other Notes
Reagent used in Mannich reactions1,2,3

REFERENCES

• Has been used as a convenient source of the Mannich intermediate: J. Org. Chem., 33, 1719 (1968). For an example (dimethylaminomethyleneation of ferrocene), see: Org. Synth. Coll., 5, 434 (1973). Reaction with o-hydroxy ɑ-aryl acetophenones leads directly to isoflavanones: Synth. Commun., 29, 3895 (1999):
  
• Caution! Theproduct of double lithiation has been reported to explode on drying: Org. Process Res. Dev., 7, 1029 (2003).