72443-18-6

Basic information

• Product Name: 2,2-DIMETHYLPROPYLISOCYANIDE
• Synonyms: 2,2-DIMETHYLPROPYLISOCYANIDE
• CAS NO: 72443-18-6
• Molecular Formula: C₆H₁₁N
• Molecular Weight: 97.16
• Mol File: 72443-18-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-DIMETHYLPROPYLISOCYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYLPROPYLISOCYANIDE(72443-18-6)
• EPA Substance Registry System: 2,2-DIMETHYLPROPYLISOCYANIDE(72443-18-6)

Safety Data

• Hazardous Substances Data: 72443-18-6(Hazardous Substances Data)

Usage

General Description

2,2-Dimethylpropylisocyanide, also known as LDA or lithium diisopropylamide, is an organolithium compound commonly used as a strong base in organic chemistry reactions. It is a powerful nucleophile and deprotonating agent due to the presence of the lithium atom and is often utilized in the deprotonation of various acidic compounds, such as ketones and esters. LDA is highly reactive and must be handled with caution, as it can react violently with water and air, releasing flammable and toxic gases. It is typically stored and handled under an inert atmosphere, such as nitrogen or argon. LDA is a valuable reagent in the synthesis of complex organic molecules and is widely used in research and industrial settings.

Upstream product

• 811-98-3 d⁽⁴⁾-methanol 
• 104014-79-1 3-(2,2-Dimethylpropyl)-3,5-dihydro-5,5-dimethyl-4H-1,2,3-triazol-4-on 
• 107769-06-2 1-(2,2-Dimethylpropyl)-4,5-dihydro-4,4-dimethyl-5-methylen-1H-1,2,3-triazol 
• 72443-12-0 4-(2,2-dimethylpropylimino)-3,3,5,5-tetramethyl-3,5-dihydro-4H-pyrazole 
• 72443-14-2 (2,2-Dimethyl-propyl)-tetramethylcyclopropylidene-amine 

Downstream Products

• 7731-35-3 benzylidene-(2,2-dimethyl-propyl)-amine 
• 108453-38-9 HRe(P(C₆H₅)3)2(CNCH₂C(CH₃)3)3 
• 85028-82-6 [Rh₂(CNCH₂C(CH₃)3)6] 
• 85028-84-8 C₆⁽²⁾H₅CHNCH₂C(CH₃)3 
• 76089-59-3 1,2,3,4-tetramethylfulvene 
• 1025367-00-3 2-[[1-(2,2-dimethyl-propyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol 
• 139167-94-5 (hydrotris(3,5-dimethylpyrazolyl)borate)Rh{C(N-neopentyl)N(Ph)C(N-neopentyl)}(CN-neopentyl) 

Relevant articles and documents

Gas-Phase Thermolysis of Pyrazolines, 3. - Electronic Structure and Gas-Phase Pyrolysis of 4-Substituted 3,5,5-Trialkyl-3,5-dihydro-4H-1,2,3-triazoles Studied by Photoelectron Spectroscopy and Semiempirical Calculations

The PE spectra of the 3,5-dihydro-4H-1,2,3-triazoles 1-3 have been recorded.The ionization potentials have been assigned to molecular orbitals on the basis of MNDO, AM1, and PM3 calculations.The most important occupied MOs are characterized as ?NNN, ?C=X (X = O, NCH3, CH2), nN-3, n+NN, n-NN and nX.The gas-phase thermolyses of 1-3 have been studied by PE-controlled real-time gas analysis.After extrusion of molecular nitrogen, the remaining reactive species cyclize to three-membered rings.At higher temperatures and in flash vacuum pyrolysis, subsequent reactions lead to smaller acyclic compounds. - Key Words: Electronic structure / Photoelectron spectroscopy / Gas-phase thermolysis / Pyrolysis / 4H-1,2,3-Triazoles, 3,5-dihydro- / Semiempirical MO calculations

Synthesis, Photolysis, and Thermolysis of a 1,4,4-Trialkyl-4,5-dihydro-5-methylene-1H-1,2,3-triazole. Highly Diastereoselective Formation of (E)-2,2-Dimethyl-N-neopentyl-1-cyclopropanimine

The 3,5-dihydro-4H-1,2,3-triazol-4-one 13 adds smoothly organolithium compounds affording the tertiary alcohols 14.Peterson olefination or - much better - Wittig olefination of 13 yield the first dihydromethylene-1,2,3-triazole 17.On irradiation (λ >/= 320 nm), 17 eliminates molecular nitrogen and produces quantitatively and diastereoselectively (>98percent d.e.) the cyclopropanimine (E)-22.At a temperature of 70 deg C, (E)-22 isomerizes (rate constants kEZ = 9.0*10-5s-1 and kZE = 15.0*10-5s-1) to the equilibrium mixture (E)-:(Z)-22 = 63:37.This decomposes quantitatively into isocyanide 23 and isobutene, either in a thermal first order reaction (k = 5.92*10-5s-1 at 150 deg C) or on irradiation (λ >/= 250 nm) at 20 deg C.On heating 17 to 70 deg C, molecular nitrogen is eliminated and the rapidly equilibrating diastereomers (E)- and (Z)-22 are formed quantitatively in a first order reaction with high (E)-diastereoselectivity (95percent d.e., kE = 1.58*10-5s-1, kZ = 0.04*10-5s-1).Obviously, the geometry of group fixed by the ring in 17 is retained to a large extent in the cyclopropanimine 22 formed, no matter whether the molecular nitrogen is eliminated photochemically or thermally.The results are interpreted in terms of identical or very similar diradical intermediates on both routes, e.g. (E)-27, (E)-28, S0(E)-30.In a way, these diradicals posses the partial structure of an (E)-1-azaallyl radical or a C=N double bond, respectively, which exhibits configurational stability.

Cyclopropanimine durch Photolyse von Pyrazoliniminen; thermische Reaktion eines angeregten Zustands

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