20615
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:
Molecular Weight:
171.28
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2352408
Product Name
2-tert-Butyl-1,1,3,3-tetramethylguanidine, ≥97.0% (GC)
InChI
1S/C9H21N3/c1-9(2,3)10-8(11(4)5)12(6)7/h1-7H3
SMILES string
CN(C)\C(=N/C(C)(C)C)N(C)C
InChI key
YQHJFPFNGVDEDT-UHFFFAOYSA-N
assay
≥97.0% (GC)
form
liquid
refractive index
n20/D 1.457
bp
88-89 °C/43 mmHg (lit.)
functional group
amine
Quality Level
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).
Disclaimer
Remark on appearance: Material may form precipitate on storage. The precipitate may easily be separated by filtration.
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
149.0 °F - closed cup
flash_point_c
65.0 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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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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