[2-(dimethylamino)ethyl]dimethylamine

• ChemBase ID: 70070
• Molecular Formular: C6H16N2
• Molecular Mass: 116.20464
• Monoisotopic Mass: 116.13134852
• SMILES: C(CN(C)C)N(C)C
• Canonical SMILES: CN(CCN(C)C)C
• InChI: InChI=1S/C6H16N2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3
• InChIKey: KWYHDKDOAIKMQN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(dimethylamino)ethyl]dimethylamine
• IUPAC Traditional name: temed
• Synonyms: TEMED ELECTROPHORESIS GRADE; N,N,N′,N′-Tetramethylethylenediamine; 1,2-Bis(dimethylamino)ethane; N,N,N',N'-Tetramethylethane-1,2-diamine; N,N,N',N'-Tetramethylethylenediamine; N1,N1,N2,N2-Tetramethyl-1,2-ethanediamine; N,N,N',N'-Tetramethyl-1,2-ethanediamine; (Dimethylamino)ethyl)dimethylamine; 2,5-Dimethyl-2,5-diazahexane; Dabco TMEDA; Dimethyl[2-(dimethylamino)ethyl]amine; Kaolizer 11; MR; N,N,N',N'-Tetramethyl-1,2-diaminoethane; N,N,N',N'-Tetramethyl-1,2-ethylenediamine; N,N,N',N'-Tetramethyldiaminoethane; Propamine D; TMED; Tetrameen; Toyocat TE; N,N,N',N'-Tetramethylethylenediamine; TEMED; TMEDA; N1,N1,N2,N2-tetramethylethane-1,2-diamine; N,N,N′,N′-Tetramethylethane-1,2-diamine; Tetramethylethylenediamine; 1,2-双(二甲基氨基)乙烷; 四甲基乙二胺; N,N,N',N'-四甲基乙二胺

Database IDs

• CAS Number: 110-18-9
• EC Number: 203-744-6
• MDL Number: MFCD00008335
• Beilstein Number: 1732991
• PubChem SID: 24865721; 162035795; 24900242; 24900591; 24900026
• PubChem CID: 8037
• CHEBI ID: 32850
• Chemspider ID: 7746
• Gmelin ID: 2707
• MeSH Name: N,N,N',N'-tetramethylethylenediamine
• Wikipedia Title: Tetramethylethylenediamine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -3.377547
• LogD (pH = 7.4): -1.7988784
• Log P: 0.208814
• Molar Refractivity: 38.0072 cm^3
• Polarizability: 14.858968 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL at 20 °C, clear, colorless; Miscible in water
• Apperance: Colorless liquid
• Melting Point: -55 °C(lit.); -55°C; -55°C; -58.65°C (214.5K)
• Boiling Point: 120-122 °C; 120-122 °C(lit.); 120-122°C; 120-122°C; 121.05°C (394.2K)
• Flash Point: 10°C; 18°C(62°F); 20 °C; 20°C; 68 °F
• Density: 0.77 g/ml; 0.77 g/ml @ 25°C; 0.775; 0.775 g/mL at 20 °C(lit.); 0.7750; 775 mg mL^-1 (at 20 °C)
• Refractive Index: 1.4179; 1.4180; n20/D 1.4179(lit.); n20/D 1.418; n20/D 1.419
• pKa: 8.97
• pKb: 5.85
• Odor: Ichtyal, ammoniacal

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Air & Moisture Sensitive; Highly Flammable/Corrosive/Harmful/Air Sensitive/Moisture Sensitive/Store under Argon; HYGROSCOPIC, FLAMMABLE
• RTECS: KV7175000
• European Hazard Symbols: Corrosive (C); Flammable (F); X
• UN Number: 2372; UN2372
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2; II
• Australian Hazchem: 3WE
• Risk Statements: 11-20/22-34; R:11-20/22; R:11-20/22-34; r11, r20/22, r34
• Safety Statements: 16-26-36/37/39-45; S:16-26-45-36/37/39; s1/2, s16, s26, s36/37/39, s45
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 129
• TSCA Listed: false; 是
• EU Index: 612-103-00-3
• GHS Pictograms: GHS corrosion; GHS exclamation mark; GHS flame; GHS02; GHS05; GHS07
• GHS Signal Word: DANGER; Danger
• NFPA704:
  

  4

  2

  1
• LD50: 268 mg kg^-1 (oral, rat); 5.39 g kg^-1 (dermal, rabbit)
• Explode Limits: 0.98–9.08%; 9.08 %
• GHS Hazard statements: 225, 302, 314, 332; H225-H302-H314-H332; H225-H314-H302-H332
• GHS Precautionary statements: 210, 280, 305+351+338, 310; 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 2372 3/PG 2

Product Information

• Purity: ~99%; >99%; ≥98.0% (GC); ≥99% (GC); ≥99.0%; ≥99.0% (GC); ≥99.5%; 95+%; 98%; 99%
• Grade: absolute; ELECTROPHORESIS; for molecular biology; purum; ReagentPlus®
• Suitability: in accordance for electrophoresis test; suitable for electrophoresis
• Impurities: ≤0.02% water; ≤1% water; DNases, none detected; phosphatases, none detected; proteases, none detected; RNases, none detected
• Cation Traces: Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Foreign Activity: DNase, RNase, protease, none detected
• Purified By: redistillation
• Product Line: BioXtra
• Linear Formula: (CH3)2NCH2CH2N(CH3)2

DETAILS

MP Biomedicals - 04805615

Electrophoresis Grade
(TEMED)
Purity: >99%
Polymerization accelerator for polyacrylamide gel formation.
Packed in nitrogen purged containers.

MP Biomedicals - 04805613

Electrophoresis Grade
(TEMED)
Purity: >99%
Polymerization accelerator for polyacrylamide gel formation.
Packed in nitrogen purged containers.

MP Biomedicals - 04805614

(TMEDA) Electrophoresis Grade (TEMED) Purity: >99% Polymerization accelerator for polyacrylamide gel formation. Packed in nitrogen purged containers.

MP Biomedicals - 02195516

Purity: 98%
Catalyst for gel formation in polyacrylamide gel electrophoresis.
1 ml = approx. 0.77 g

MP Biomedicals - 02194019

Molecular Biology Reagent
Purity: ~99%
Polyacrylamide gel formation catalyst.
1 ml = approx. 0.77 g

Sigma Aldrich - T9281

Analysis Note
经测试可用作 PAGE 的催化剂。
Application
TEMED 是用于催化过硫酸铵或核黄素形成自由基的叔胺基。自由基将引起丙烯酰胺和 N,N'-亚甲基双丙烯酰胺聚合形成可用于筛分大分子的凝胶基质。
Caution
在惰性气体下处理和储存，易受空气和水分影响。
包装
25, 50, 100 mL in glass bottle

Sigma Aldrich - T7024

包装
25, 50, 100 mL in glass bottle
Quantity
针对 50mL 丙烯酰胺凝胶溶液，建议用量为 35μL。

Sigma Aldrich - 411019

Application
Employed together with BuLi to abstract a vinylic hydrogen from a conformationally twisted styrene derivative.1
Packaging
1 L in Sure/Seal™
100 mL in Sure/Seal™

Sigma Aldrich - 87689

Other Notes
Solutions of TEMED should be stored in the dark1.

Sigma Aldrich - 87687

Other Notes
Preparation of polyacrylamide gels - polymerization initiator1

Sigma Aldrich - 87690

Other Notes
Substitute for the cancerogenic HMPA as additive for reactions with alkynyl lithium reagents in THF1

Sigma Aldrich - T22500

Packaging
1 L in glass bottle
5, 100, 500 mL in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 30-1220

Suitability
for electrophoresis

Toronto Research Chemicals - T303050

N,N,N',N'-Tetramethylethylenediamine is used as polymerization accelerator in gel electrophoresis, solvent and oxidizing reagent.

REFERENCES

• Bassam, B.J., et al.: BioTechniques, 19, 568 (1995)
• Moham, D., et al.: J. Chromatogr., 979, 271 (1995)
• In catalytic amounts, produces up to a 20-fold increase in reaction rate in aqueous Michael additions catalyzed by ytterbium triflate: J. Org. Chem., 71, 352 (2006).
• Widely used complexing agent in lithiation reactions, often giving enhanced reactivity in otherwise difficult metallations: J. Am. Chem. Soc., 92, 4664 (1970). Subsequent work by Collum and others indicated that the situation may be much less straightforward than was previously thought, but the effect of TMEDA is likely to be most pronounced in the absence of strong donor solvents such as THF. For a discussion of the factors involved, see: Acc. Chem. Res., 25, 448 (1992). Under some conditions also, TMEDA itself may undergo lithiation: Organometallics, 13, 5173 (1994).
• Used in combination with alkyllithiums in the ortho-metallation of aromatics; see, e.g.: Org. Synth. Coll., 6, 478 (1988); Org. Synth. Coll., 9, 559 (1998). For discussion of the dramatic acceleration of the rate of ortho-lithiation of anisole in the presence of TMEDA, effective also in sub-stoichiometric amounts, see: Tetrahedron Lett., 35, 385 (1994). See also Tetrahedron Lett., 35, 401 (1994), J. Org. Chem., 62, 3024 (1997) for further discussion of the role of TMEDA in ortho-metallation.
• The oxidative coupling of terminal acetylenes to diynes, by O₂ in the presence of CuCl, is improved by addition of TMEDA as a complexing agent: J. Org. Chem., 27, 3320 (1962). For example and discussion, see: Org. Synth. Coll., 8, 63 (1993):