999-78-0

Basic information

• Product Name: 4,4-Dimethyl-2-pentyne
• Synonyms: 4,4-DIMETHYL-2-PENTYNE;T-BUTYLMETHYLACETYLENE;TIMTEC-BB SBB008719;(tert-C4H9)CequivCCH3;1-tert-butyl-1-propyne;2,2-dimethyl-3-pentyne;2-pentyne,4,4-dimethyl-;4,4-dimethyl-pent-2-yne
• CAS NO: 999-78-0
• Molecular Formula: C₇H₁₂
• Molecular Weight: 96.17
• EINECS: -0
• Product Categories: organic compound
• Mol File: 999-78-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: -82.4°C
• Boiling Point: 83°C
• Flash Point: -10°C
• Appearance: colorless/liquid
• Density: 0.718
• Vapor Pressure: 85.6mmHg at 25°C
• Refractive Index: 1.4071
• Water Solubility: Immiscible with water.
• BRN: 1733540
• CAS DataBase Reference: 4,4-Dimethyl-2-pentyne(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4-Dimethyl-2-pentyne(999-78-0)
• EPA Substance Registry System: 4,4-Dimethyl-2-pentyne(999-78-0)

Safety Data

• Statements: 11
• Safety Statements: 9-16-33
• RIDADR: 3295
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 999-78-0(Hazardous Substances Data)

Usage

Uses

4,4-Dimethyl-2-pentyne is used in organometallic reactions for regioselectivity of its insertion into the Pd-C bond of cyclopalladated complexes. It is also used to prepare pyrimidine-dione by reacting with isocyanate in the presence of nickel/ N-heterocyclic carbene.

Synthesis Reference(s)

Tetrahedron Letters, 22, p. 2443, 1981 DOI: 10.1016/S0040-4039(01)92928-4

InChI:InChI=1/C7H12/c1-5-6-7(2,3)4/h1-4H3

Upstream product

• 145527-19-1 C₂₅H₂₇PS 
• 74-88-4 methyl iodide 
• 91229-76-4 W(CC(CH₃)3)(OC₆H₃(CH(CH₃)2)2)3 
• 75-05-8 acetonitrile 
• 999-79-1 4-chloro-4-methylpent-2-yne 
• 75-16-1 methylmagnesium bromide 
• 60-29-7 diethyl ether 

Downstream Products

• 676-97-1 methylphosphonic acid dichloroanhydride 
• 4707-95-3 tert-butyl phosphinyl dichloride 
• 29507-64-0 5-t-butyl-3H-1,2-dithiole-3-thione 
• 590-50-1 4,4-dimethyl-pentan-2-one 
• 564-04-5 2,2-dimethyl-3-pentanone 
• 64235-56-9 (E)-2,4,4-trimethyl-1-phenyl-2-penten-1-one 
• 125540-61-6 (Z)-2-tert-Butyl-1-phenyl-but-2-en-1-one 
• 125540-75-2 (Z)-2,4,4-Trimethyl-1-phenyl-pent-2-en-1-one 
• 92-52-4 biphenyl 
• 75909-62-5 2-t-butyl-3-methyl-1,4-naphthoquinone 
• 598-98-1 Methyl pivalate 
• 40898-19-9 4,4-dimethyl-2,3-pentanedione 
• 75-98-9 Trimethylacetic acid 
• 128075-71-8 2,2-dimethyl-1-(oxiran-2-yl)propan-1-one 

Relevant articles and documents

Properties and Reactivities of Zwitterionic Platinum(II)-ate Complexes Generated by Transforming Coordination of an Alkyne-Bisphosphine Ligand

Coordination of an alkyne-bisphosphine ligand with platinum(II) precursors produced a structural reorganization in the ligand backbone to form stable zwitterionic platinum(II) complexes bearing an anionic platinum center. The structural properties and reactivities of these complexes were investigated using X-ray crystallographic analyses, computational studies, and stoichiometric reactions involving oxidative addition and reductive elimination. These studies have shown that the enhanced nucleophilicity of the platinum center to alkyl halides promotes smooth oxidative addition and that the charge rebalance accelerates the dissociation of the halide anion from the platinum(IV) intermediate, which is essential in the carbon-carbon bond-forming step.

Thermal rearrangement of thiocarbonyl-stabilised triphenylphosphonium ylides leading to (Z)-1-diphenylphosphino-2-phenylsulfenylalkenes

While thermolysis of thiocarbonyl-stabilised phosphonium ylides generally results in extrusion of Ph3PS to give alkynes, those with a PCH function instead undergo a novel P to S transfer of a phenyl group to give (Z)-configured 1-phosphino-2-su