2-tert-Butyl-1,1,3,3-tetramethylguanidine
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2-tert-Butyl-1,1,3,3-tetramethylguanidine
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CAS No:
29166-72-1
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Formula:
C9H21N3
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Chemical Name:
2-tert-Butyl-1,1,3,3-tetramethylguanidine
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Synonyms:
Guanidine,N′′-(1,1-dimethylethyl)-N,N,N′,N′-tetramethyl-;Guanidine,2-tert-butyl-1,1,3,3-tetramethyl-;N′′-(1,1-Dimethylethyl)-N,N,N′,N′-tetramethylguanidine;Tetramethyl-2-tert-butylguanidine;N-tert-Butyl-N′,N′,N′′,N′′-tetramethylguanidine;2-tert-Butyl-1,1,3,3-tetramethylguanidine;Barton base
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CAS No:
Safety Information
Ⅱ
UN 3267 8/PG 2
3
22-34
26-36/37/39-45
C
P280-P305 + P351 + P338-P310
H302-H314
|Danger|H227 (25%): Combustible liquid [Warning Flammable liquids]|P210, P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P370+P378, P403+P235, P405, and P501|Aggregated GHS information provided by 4 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-tert-Butyl-1,1,3,3-tetramethylguanidine Use and Manufacturing
To a solution of tetramethyl urea (500 mmol) in toluene (80 mL) at room temperature under argon atmosphere, oxalyl chloride (550 mmol) was added dropwise. The mixture was heated at 60 °C for 5 h, forming a white precipitate. The precipitate was filtered using a Buchner funneland then washed with diethyl ether. The resulting white solid was suspended in acetonitrile (240mL) and gradually added to a solution of tert-butylamine (550 mmol) and triethyl amine (1 mol) in acetonitrile (300 mL) at room temperature under argon atmosphere. The mixture was heated under reflux for 3 h. After the reaction mixture was evaporated to remove acetonitrile, the resulting solid was stirred in anhydrous diethyl ether to remove the organic by-products from the solid, rapidly filtered using a Buchner funnel, and washed with anhydrous diethyl ether. The filtered solid was dissolved in diethyl ether and 20percent NaOH aqueous solution (400 mL). After the organic layer was separated, the aqueous layer was twice extracted with diethyl ether. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The resulting liquid was purified by distillation, affording the desired productin 82percent yield.
Computed Properties
Molecular Weight:171.28
XLogP3:0.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:171.173547683
Monoisotopic Mass:171.173547683
Topological Polar Surface Area:18.8
Heavy Atom Count:12
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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2-tert-Butyl-1,1,3,3-tetramethylguanidine
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