29166-72-1 Usage
Preparation
To an ovendried, 500-mL, three-necked, round-bottomed flask, equipped with a nitrogen inlet with gas bubbler, magnetic stirring bar, thermometer, condenser, and a 250-mL dropping funnel, were added triphosgene (14.8 g, 0.05 mol) and anhydrous toluene (120 mL). The mixture was kept under argon and cooled to ca. 10 C° with the aid of an external ice bath. A solution of N,N,N,N-tetramethylurea (18.0 mL, 0.15 mol) in dry toluene (50 mL) was then slowly added over a period of 30 min. After completion of the addition, the mixture was allowed to warm to ambient temperature, and stirring was continued for a further 1 h. During this time, a white precipitate formed, consisting of the Vilsmeier salt. Then, tert-butylamine (47.3 mL, 0.45 mol) was slowly added to the mixture over a period of 30 min. After completion of the addition, the mixture was heated under reflux for 5 h and then cooled to room temperature. Anhydrous diethyl ether (200 mL) was added and the white precipitate was quickly removed by filtration. This precipitate had to be collected as quickly as possible to avoid hydrolysis to the starting urea. The precipitate turns pale-yellow if hydrolysis is occurring. In some instances, additional diethyl ether (300 mL) was needed to ensure complete transfer of the solids to the filtration apparatus. The precipitate was washed with a further quantity of anhydrous diethyl ether (300 mL) (the filtrate must be colorless, indicating that all impurities have been removed) and immediately dissolved in aqueous 25% sodium hydroxide solution (100 mL). The mixture was then extracted with diethyl ether (3 × 300 mL). The combined organic layers were dried (potassium carbonate), filtered, and the solvent was removed under reduced pressure. The resulting colorless liquid was purified by distillation (bp 88–89 C°/36 mmHg) to afford 18.7 g (73%) of 2-tertbutyl- 1,1,3,3-tetramethylguanidine 1779.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 29166-72-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,1,6 and 6 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 29166-72:
(7*2)+(6*9)+(5*1)+(4*6)+(3*6)+(2*7)+(1*2)=131
131 % 10 = 1
So 29166-72-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H21N3/c1-9(2,3)10-8(11(4)5)12(6)7/h1-7H3
29166-72-1Relevant articles and documents
Selective Synthesis of Carbonates from Glycerol, CO 2, and Alkyl Halides Using tert -Butyltetramethylguanidine
Mihara, Masatoshi,Moroga, Kaname,Iwasawa, Tetsuo,Nakai, Takeo,Ito, Takatoshi,Ohno, Toshinobu,Mizuno, Takumi
supporting information, p. 1759 - 1764 (2018/07/21)
Herein, we describe the guanidine-promoted synthesis of carbonates from glycerol, CO 2, and alkyl halides. Specifically, a linear tricarbonate (1,2,3-tri- O -butoxycarbonylglycerol), a dicarbonate [butyl (2-oxo-1,3-dioxolan-4-yl)methyl carbonate] containing a linear and a cyclic moiety, and a cyclic monocarbonate (4-hydroxymethyl-2-oxo-1,3-dioxolan) were selectively obtained in good yields, which were strongly affected by the steric bulkiness of the guanidine group substituents. The developed method exhibits the advantages of high efficiency and mild conditions, thus being a powerful tool for the synthesis of value-added products from industrial by-products.
Preparation and reactions of 2-tert-butyl-1,1,3,3-tetramethylguanidine: 2,2,6-trimethylcyclohexen-1-yl iodide
Barton, Derek H. R.,Chen, Mi,Jászberényi, Joseph Cs.,Taylor, Dennis K.
, p. 101 - 101 (2017/09/12)
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The Synthesis and Properties of a Series of Strong but Hindered Organic Bases
Barton, Derek H. R.,Elliott, John D.,Gero, Stephen D.
, p. 1136 - 1137 (2007/10/02)
A series of highly hindered N1,N2,N2,N3,N3-penta-alkylguanidines has been synthesised from inexpensive starting materials; these strong bases show interesting effects in organic synthesis.
