1,1,3,3-tetramethylguanidine

• ChemBase ID: 85801
• Molecular Formular: C5H13N3
• Molecular Mass: 115.17682
• Monoisotopic Mass: 115.11094743
• SMILES: N=C(N(C)C)N(C)C
• Canonical SMILES: CN(C(=N)N(C)C)C
• InChI: InChI=1S/C5H13N3/c1-7(2)5(6)8(3)4/h6H,1-4H3
• InChIKey: KYVBNYUBXIEUFW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,1,3,3-tetramethylguanidine
• IUPAC Traditional name: 1,1,3,3-tetramethylguanidine
• Synonyms: N,N,N′,N′-Tetramethylguanidine; 1,1,3,3-Tetramethylguanidine; 1,1,3,3-Tetramethylguanidine 99%; N,N,N',N'-Tetramethylguanidine; 1,1,3,3-TETRAMETHYLGUANIDINE; N,N,N′,N′-Tetramethylguanidine; 1,1,3,3-Tetramethylguanidine; TMG; 四甲基胍; 1,1,3,3-四甲基胍; 1,1,3,3-四甲基胍; 四甲基胍

Database IDs

• CAS Number: 80-70-6
• EC Number: 201-302-7
• MDL Number: MFCD00008323
• Beilstein Number: 969608
• PubChem SID: 162072917; 24854327
• PubChem CID: 66460
• Chemspider ID: 59832
• MeSH Name: 1,1,3,3-tetramethylguanidine
• Wikipedia Title: 1,1,3,3-Tetramethylguanidine

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.5731256
• LogD (pH = 7.4): -2.5730073
• Log P: -0.15766808
• Molar Refractivity: 45.9974 cm^3
• Polarizability: 12.938409 Å^3
• Polar Surface Area: 30.33 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Miscible in water
• Apperance: APHA: ≤150; Colourless liquid
• Melting Point: <-30°C; -30°C
• Boiling Point: 160 - 162°C; 162°C; 162-163 °C(lit.); 162-163°C; 52-54 °C/11 mmHg(lit.); 52-54°C
• Flash Point: 140 °F; 60 °C; 60°C; 60°C(140°F)
• Density: 0.916; 0.916 g/mL at 20 °C(lit.); 0.918; 0.918 g/mL at 25 °C(lit.); 0.92 g/ml; 918 mg mL^-1
• Refractive Index: 1.469; 1.4690; n20/D 1.469; n20/D 1.469(lit.)
• Vapor Pressure: 0.2 mm Hg (20°C); 0.2 mmHg ( 20 °C); 30 Pa (at 20 °C)
• pKa: 13.6
• pKb: 0.4

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Air Sensitive; Flammable/Corrosive/Harmful/Moisture Sensitive/Store under Argon
• European Hazard Symbols: Corrosive (C); Flammable (F); X
• UN Number: 2920; UN2920
• German water hazard class: 1
• Hazard Class: 3; 8
• Packing Group: 2; II
• Australian Hazchem: 2W
• Risk Statements: 22-34; R:10-34; r22, r34
• Safety Statements: 26-27-36/37/39-45; 26-36/37/39-45; S:16-26-27/28-36/37/39-46-64; s26, s27, s36/37/39, s45
• EU Classification: CF1
• EU Hazard Identification Number: 8A
• Emergency Response Guidebook(ERG) Number: 132
• TSCA Listed: 是
• GHS Pictograms: GHS corrosion; GHS exclamation mark; GHS flame; GHS02; GHS05; GHS06; GHS07
• GHS Signal Word: DANGER; Danger
• Explode Limits: 1–7.5%
• GHS Hazard statements: 226, 302, 314; H226-H302-H314; H301-H314-H318-H226
• GHS Precautionary statements: 280, 305+351+338, 310; P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; 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 2920 8/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... EPHX2(2053)mouse ... Ephx2(13850)

Product Information

• Purity: ≥97.0% (GC); ≥99.0% (GC); 99%
• Grade: Lonza quality; puriss.; technical
• Impurities: ≤0.50% water
• Linear Formula: (CH3)2NC(=NH)N(CH3)2

DETAILS

MP Biomedicals - 02152117

Reagent for phosphotriester cleavage in oligonucleotide synthesis.
1 ml = approx. 0.92 g

MP Biomedicals - 05218980

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 241768

Packaging
5, 100, 500 mL in glass bottle
Application
Base employed in the preparation of alkyl nitriles from alkyl halides and 3′-alkylthymidines from 3′-nitrothymidines.
Promotes the pentavalent bismuth oxidation of primary and secondary alchohols to aldehydes and ketones.1

Sigma Aldrich - 690953

Packaging
1 kg in glass bottle
10 kg in comp drum

REFERENCES

• Strong organic base useful for the formation of organic-soluble salts, and as a basic catalyst, e.g. in Michael addition reactions: J. Org. Chem., 27, 3175 (1962); Tetrahedron Lett., 569 (1973). Preferred catalyst in the Michael addition of aliphatic nitro compounds to unsaturated esters: Synthesis, 44 (1972); 953 (1989); Tetrahedron Lett., 30, 993 (1989).
• Useful base for formation of TBDMS ethers of alcohols with tert-Butyldimethylchlorosilane, A13064: J. Org. Chem., 49, 4657 (1984).
• Other uses include: Acylation of amino acids by methyl trifluoroacetate: Synthesis, 399 (1976). Formation of Boc-amino acids with tert-butyl phenyl carbonate: Org. Synth. Coll., 6, 203 (1988). Cleavage of peptides from resins: Tetrahedron, 40, 4237 (1984). Selective cleavage of a primary benzyloxycarbonyl (Cbz, Z) group in the presence of either Boc or secondary Cbz: J. Chem. Soc., Perkin 1, 1905 (1988). See also 4-Chloromethylpyridine hydrochloride, A12859 and Appendix 6.
• For use in the Baylis-Hillman reaction, see: J. Chem. Soc., Perkin 1, 2831 (2001).
• Inexpensive and efficient ligand for the palladium-catalyzed Heck reaction: Synlett, 1885 (2005).