21981-37-3

Basic information

• Product Name: Di-tert-butylamine
• Synonyms: 1,1'-Iminobis(1,1-dimethylethane);Bis(tert-butyl)amine;Di-tert-butylamine;N-(1,1-Dimethylethyl)-2-methyl-2-propanamine;2-PropanaMine, N-(1,1-diMethylethyl)-2-Methyl-;N-tert-butyl-2-Methylpropan-2-aMine
• CAS NO: 21981-37-3
• Molecular Formula: C₈H₁₉N
• Molecular Weight: 129.24
• Mol File: 21981-37-3.mol

Chemical Properties

• Boiling Point: 129.4°C at 760 mmHg
• Flash Point: 12.8°C
• Appearance: /
• Density: 0.762g/cm³
• Vapor Pressure: 10.2mmHg at 25°C
• Refractive Index: 1.417
• PKA: 10.76±0.48(Predicted)
• CAS DataBase Reference: Di-tert-butylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Di-tert-butylamine(21981-37-3)
• EPA Substance Registry System: Di-tert-butylamine(21981-37-3)

Safety Data

• Hazardous Substances Data: 21981-37-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 491, 1984 DOI: 10.1016/S0040-4039(00)99919-2

InChI:InChI=1/C8H19N/c1-7(2,3)9-8(4,5)6/h9H,1-6H3

Upstream product

• 109-95-5 ethyl nitrite 
• 677-22-5 tert-butylmagnesium chloride 
• 507-19-7 t-butyl bromide 
• 67-56-1 methanol 
• 82881-21-8 1,3-Di-tert-butyl-2-(di-tert-butylamino)-4,4-dimethyl-1,3,2,4-diazaphosphasiletidin 

Downstream Products

• 110808-07-6 1-(2-Allyl-5-methyl-phenoxy)-3-(di-tert-butyl-amino)-propan-2-ol 
• 20265-77-4 di-tertbutylaniline 
• 110808-09-8 1-(2-Allyl-4-methyl-phenoxy)-3-(di-tert-butyl-amino)-propan-2-ol 
• 63819-70-5 N-Nitroso-di-tert.-butylamin 

Relevant articles and documents

An improved and one-pot procedure to the synthesis of symmetric amines by domino reactions of 5-methyl-1,3,4-thiadiazole-2-amine, a new nitrogen atom donor, and alkyl halides

Abstract: A new one-pot method has been introduced in this work for the synthesis of symmetrical primary, secondary, and tertiary alkyl amines from alkyl halides and 5-methyl-1,3,4-thiadiazole-2-amine as a nitrogen-transfer reagent. In this method, all three types of amines have been successfully prepared after changing the ratio of substrates and base control. In addition to the introduction of a new nitrogen-transfer reagent, other important features of this work include normal atmospheric conditions and excellent yields under mild reaction conditions.

Element-Organic Amine/Imine Compounds, XXIII. Rotamers of Aminophosphanes and Aminophosphoranes

The diazaphosphasiletidines 3a - h can be synthesized from R2Si(NCR3Li)2 and Cl2PNR1R2 (1) as well as from (2) and MNR1R2 (R = CH3).At ambient temperature they show hindered rotation about the P - NR1R2 bond. 3g is separated as a pair of E/Z-rotamers, whose structure has been elucidated by NMR and X-ray analyses.The kinetically measured P - N rotation barriers (ΔG* ca. 30 kcal/mol) are until now the highest that have been measured.The isomerization of 3g (E) -> 3g(Z) (P - N rotation, P inversion, or both) is a P - N rotation which has been established by the synthesis and the NMR spectroscopically measured rearra ngement of (3i) (R = CH3, four isomers).The interaction of 3a - h with sulfur, selenium, and methyl iodide gives 4 - 6a - h.Below 0 deg C they all show hindered rotation about the P - NR1R2 bond. 4 and 5 are suitable for the study of the structure dependence of 1H NMR ASIS effects.The oxidation of 3g(E/Z) to the isomers 4g - 6g(E/Z) occurs with retention of configuration.These compounds show significant differences with respect to their thermal stability and their reaction with methanol.The comparison of the ΔG* values of the P - N rotation barriers of 3 - 6 shows that the steric influence of the exo-amino substituents R1 and R2 is most important.The E/Z equilibrium of the unsymmetrically substituted compounds gives evidence that the two ground states of P - N rotation are mostly sterically, possibly also electronically.