29166-72-1 Usage
Uses
Used in Pharmaceutical Industry:
2-TERT-BUTYL-1,1,3,3-TETRAMETHYLGUANIDINE is used as a coupling agent for the synthesis of various pharmaceutical compounds. Its application is particularly beneficial due to its ability to enhance the efficiency of coupling reactions, leading to the production of desired products with improved yields and reduced reaction times.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-TERT-BUTYL-1,1,3,3-TETRAMETHYLGUANIDINE is used as a base to facilitate a wide range of chemical reactions. Its use as a base allows for the formation of new chemical bonds, which is crucial in the synthesis of complex molecules and compounds.
Used in Research and Development:
2-TERT-BUTYL-1,1,3,3-TETRAMETHYLGUANIDINE is also utilized in research and development settings as a tool to study and understand the mechanisms of various chemical reactions. Its unique properties make it an invaluable asset in the exploration of new reaction pathways and the development of novel synthetic methods.
Overall, 2-TERT-BUTYL-1,1,3,3-TETRAMETHYLGUANIDINE is a versatile compound with a wide range of applications across different industries, particularly in the fields of pharmaceuticals, chemical synthesis, and research and development. Its ability to promote coupling reactions and enhance the efficiency of various chemical processes makes it a valuable asset in the development of new products and the advancement of scientific knowledge.
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.
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 academic research and scientific papers
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.
Guanidine/Pd(OAc)2-catalyzed room temperature Suzuki cross-coupling reaction in aqueous media under aerobic conditions
Li, Shenghai,Lin, Yingjie,Cao, Jungang,Zhang, Suobo
, p. 4067 - 4072 (2008/02/04)
(Chemical Equation Presented) A highly efficient Pd(OAc) 2/guanidine aqueous system for the room temperature Suzuki cross-coupling reaction has been developed. The new water-soluble and air-stable catalyst Pd(OAc)2·(1f)2 from Pd-(OAc)2 and 1,1,3,3-tetramethyl-2-n-butylguanidine (1f) was synthesized and characterized by X-ray crystallography. In the presence of Pd(OAc) 2·(1f)2, coupling of arylboronic acids with a wide range of aryl halides, including aryl iodides, aryl bromides, even activated aryl chlorides, was carried out smoothly in aqueous solvent to afford the cross-coupling products in good to excellent yields and high turnover numbers (TONs) (TONs up to 850 000 for the reaction of 1-iodo-4-nitrobenzene and phenylboronic acid). Furthermore, this mild protocol could tolerate a broad range of functional groups.
Synthesis and Properties of a Series of Sterically Hindered Guanidine Bases
Barton, Derek H. R.,Elliott, John D.,Gero, Stephan D.
, p. 2085 - 2090 (2007/10/02)
By the reaction of Vilsmeier salts, derived from tetra-alkylureas or from tetra-alkylthioureas, with primary aliphatic amines, a series of sterically hindered penta-alkyl guanidines has been prepared. 2-t-Butyl-1',1',3'',3''-tetramethylguanidine and pentaisopropylguanidine combine ease of preparation with a range of resistance to alkylating agents.Preliminary experiments indicate that these inexpensive bases will useful in organic synthesis.
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.
