CAS 80-70-6|1,1,3,3-Tetramethylguanidine 99%|1,1,3,3-tetramethylguanidine|1,1,3,3-tetramethylguanidine|N,N,N′,N′-Tetramethylguanidine|四甲基胍|1,1,3,3-四甲基胍|1,1,3,3-TETRAMETHYLGUANIDINE|N,N,N',...

General Information

Structure

Molecular Formula

C₅H₁₃N₃

Molecular Mass

115.17682

Exact Mass

115.11094743

Charge

InChI

InChI=1S/C5H13N3/c1-7(2)5(6)8(3)4/h6H,1-4H3

InChIKey

KYVBNYUBXIEUFW-UHFFFAOYSA-N

Canonic Smiles

CN(C(=N)N(C)C)C

Isomeric Smiles

N=C(N(C)C)N(C)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-2.5731256

LogD (pH = 7.4)

-2.5730073

Log P

-0.15766808

Molar Refractivity

45.9974

Polarizability

12.938409

Polar Surface Area

30.33

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

1,1,3,3-Tetramethylguanidine 99%1,1,3,3-四甲基胍N,N,N′,N′-Tetramethylguanidine四甲基胍1,1,3,3-TETRAMETHYLGUANIDINEN,N,N',N'-Tetramethylguanidine1,1,3,3-Tetramethylguanidine四甲基胍1,1,3,3-四甲基胍1,1,3,3-TetramethylguanidineTMGN,N,N′,N′-Tetramethylguanidine

IUPAC name

1,1,3,3-tetramethylguanidine

IUPAC Traditional name

1,1,3,3-tetramethylguanidine

Names and Identifiers

Registration numbers

Beilstein Number

EC Number

MDL Number

CAS Number

PubChem SID

PubChem CID

Wikipedia Title

1,1,3,3-Tetramethylguanidine

Chemspider ID

59832

MeSH Name

1,1,3,3-tetramethylguanidine

Registration numbers

Properties

Pharmacology Properties

human ... EPHX2(2053)mouse ... Ephx2(13850)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02152117

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

05218980

MP Biomedicals Rare Chemical collection

Wikipedia

1,1,3,3-Tetramethylguanidine

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

690953

Packaging
1 kg in glass bottle
10 kg in comp drum

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity