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690953

Sigma-Aldrich

N,N,N′,N′-Tetramethylguanidine

≥99.0% (GC)

Synonym(s):

1,1,3,3-Tetramethylguanidine

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About This Item

Linear Formula:
(CH3)2NC(=NH)N(CH3)2
CAS Number:
80-70-6
Molecular Weight:
115.18
Beilstein:
969608
EC Number:
201-302-7
MDL number:
MFCD00008323
UNSPSC Code:
12352100
PubChem Substance ID:
329761375
NACRES:
NA.22

Quality Level

200

Assay

≥99.0% (GC)

form

liquid

impurities

≤0.50% water

color

APHA: ≤150

bp

162-163 °C (lit.)

density

0.916 g/mL at 20 °C (lit.)

functional group

amine

SMILES string

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

InChI

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

InChI key

KYVBNYUBXIEUFW-UHFFFAOYSA-N

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Application

N,N,N′,N′-Tetramethylguanidine can be used to synthesize:
  • dinucleoside phosphotriester1
  • 1,1,3,3-tetramethylguanidinium 2-ethylhexoate2
  • tetramethylguanidine ionic liquid (TMG IL)3

Signal Word

Danger

Hazard Statements

H226,H290,H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Met. Corr. 1 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

122.0 °F - closed cup

Flash Point(C)

50 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG9975
BCCG1658
BCCF4610
BCCF3076
BCBZ9181

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Tetramethyl guanidinium chlorosulfonate as a highly efficient and recyclable organocatalyst for the preparation of bis (indolyl) methane derivatives.
Kalla R, et al.
Catalysis Communications, 57, 55-59 (2014)
Deoxyribonucleoside cyclic N-acylphosphoramidites as a new class of monomers for the stereocontrolled synthesis of oligothymidylyl-and oligodeoxycytidylyl-phosphorothioates.
Wilk A, et al.
Journal of the American Chemical Society, 122(10), 2149-2156 (2000)
Synthesis and thermal characterization of novel poly (tetramethylsilanthrylenesiloxane) and poly (tetramethylsilphenanthrylenesiloxane) derivatives.
Sato I, et al.
Polymer Bull., 59(5), 607-617 (2007)
G V S M Carrera et al.
Faraday discussions, 183, 429-444 (2015-09-22)
In this report, novel systems, based on highly abundant saccharides, D-mannose, D-glucose, β-cyclodextrin, alginic acid and mannitol, in combination with an organic superbase, tetramethylguanidine (TMG) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), are studied for carbon dioxide capture. With D-mannose and D-glucose, several ratios

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