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20615

Sigma-Aldrich

2-tert-Butyl-1,1,3,3-tetramethylguanidine

≥97.0% (GC)

Synonym(s):

BTMG

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About This Item

Empirical Formula (Hill Notation):
C9H21N3
CAS Number:
29166-72-1
Molecular Weight:
171.28
Beilstein:
2352408
MDL number:
MFCD01862972
UNSPSC Code:
12352100
PubChem Substance ID:
57647848
NACRES:
NA.22

Quality Level

200

Assay

≥97.0% (GC)

form

liquid

refractive index

n20/D 1.457

bp

88-89 °C/43 mmHg (lit.)

SMILES string

CN(C)\C(=N/C(C)(C)C)N(C)C

InChI

1S/C9H21N3/c1-9(2,3)10-8(11(4)5)12(6)7/h1-7H3

InChI key

YQHJFPFNGVDEDT-UHFFFAOYSA-N

General description

2-tert-Butyl-1,1,3,3-tetramethylguanidine (Barton′s base) is an excellent alternative to traditional inorganic bases for promoting the coupling reaction.

Application

  • Synthesis of dinaphthyl ethers: Barton′s base, which includes 2-tert-Butyl-1,1,3,3-tetramethylguanidine, was utilized to promote SNAr reactions for the synthesis of highly oxygenated dinaphthyl ethers, demonstrating its efficacy as a catalyst in complex organic synthesis processes (Wipf and Lynch, 2003).

Caution

Remark on appearance: Material may form precipitate on storage. The precipitate may easily be separated by filtration.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

149.0 °F - closed cup

Flash Point(C)

65.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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D.H.R. Barton et al.
Organic Syntheses, 74, 103-103 (1997)
Peter Wipf et al.
Organic letters, 5(7), 1155-1158 (2003-03-28)
[reaction: see text] Electron-rich dinaphthyl ethers were synthesized by S(N)Ar reactions between naphthols and activated fluoronaphthalenes. 2-tert-Butyl-1,1,3,3-tetramethylguanidine (Barton's base) was found to be an excellent, mild alternative to traditional inorganic bases for promoting the coupling reaction.

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