13183-68-1

Basic information

• Product Name: 2-METHYLPROPANE-2-D
• Synonyms: (CH3)3CD;Isobutane-d1;Propane-2-d, 2-methyl-;2-METHYLPROPANE-2-D;2-METHYLPROPANE-2-D1;2-METHYLPROPANE-2-D, 98 ATOM % D;2-Methylpropane-2-D1 (gas);isobutane-2-d
• CAS NO: 13183-68-1
• Molecular Formula: C₄H₁₀
• Molecular Weight: 59.13
• Mol File: 13183-68-1.mol

Chemical Properties

• Melting Point: −160 °C(lit.)
• Boiling Point: −12 °C(lit.)
• Flash Point: -83°C
• Appearance: /
• Density: 0.622 g/cm³
• Vapor Density: 2.01 (21 °C, vs air)
• Vapor Pressure: 1536 mm Hg ( 21 °C)
• Refractive Index: 1.352
• CAS DataBase Reference: 2-METHYLPROPANE-2-D(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLPROPANE-2-D(13183-68-1)
• EPA Substance Registry System: 2-METHYLPROPANE-2-D(13183-68-1)

Safety Data

• Hazard Codes: F,F+
• Statements: 11-12
• Safety Statements: 16-33-36-38
• RIDADR: UN 1969 2.1
• WGK Germany: 3
• Hazardous Substances Data: 13183-68-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H10/c1-4(2)3/h4H,1-3H3/i4H

Upstream product

• 507-20-0 tertiary butyl chloride 
• 75-28-5 Isobutane 
• 123499-10-5 (dideuteriomethylene)triphenylphosphorane 
• 594-19-4 tert.-butyl lithium 
• 67108-87-6 (η5-pentamethylcyclopentadienyl)2(zirconium)(D)(CH2CD(CH3)2) 
• 67108-86-5 (η5-pentamethylcyclopentadienyl)2(zirconium)(H)(iosbutyl)2 
• 677-22-5 tert-butylmagnesium chloride 

Downstream Products

• 34557-54-5 methane 
• 676-49-3 Monodeuteromethan 
• 19170-96-8 decadeuterioisobutane 
• 74-85-1 ethene 
• 2680-00-4 ethylene-d1 
• 75-28-5 Isobutane 
• 1333-74-0 hydrogen 
• 16873-17-9 deuterium 
• 2680-01-5 ethylene-d3 
• 683-73-8 Ethylene-d4 
• 34097-83-1 2-methylpentane-2d 
• 507-20-0 tertiary butyl chloride 
• 60640-37-1 1-chloro-2-deuterio-2-methyl-propane 

Relevant articles and documents

Interaction of t-butyllithium and triphenylmethylenephosphoranes

NMR experiments show that a directed ortho-metalation occurs at one of the aromatic rings of triphenylmethylenephosphoranes (Ph3P-CHR, R = H, Me) when the phosphorus ylide is treated with 1 equiv. t-BuLi. If pre- coordination of t-BuLi is inhibited by a sterically demanding and electron- withdrawing substituent (R = SiMe3) no metalation is observed. (C) 2000 Elsevier Science Ltd.

Synthesis of deuterium labeled isobutane: Isobutane-2-d1, isobutane-1-d9 and isobutane-d10

2-Methylpropane-2-d1 (isobutane-2-d1), 2-(methyl-d3)-propane-1,1,1,3,3,3-d6 (nonadeuterated isobutane) and 2-methylpropane-d10 (perdeuterated isobutane) were synthesized by using a combination of classical organic chemistry and recently developed H/D exchange processes on solid acids. Isobutane-2-d1 was synthesized from t-butyl chloride by Grignard synthesis with an overall yield of 27.0% (chemical purity: 99.9% and isotopic purity: 96.0%). Isobutane-1-d9 was prepared by H/D exchange of 2-methylpropane (isobutane) with a D2O exchanged zeolite. The deuteriated product was obtained with an overall yield of 80.0% (chemical purity: 99.9% and isotopic purity: 98.7%). Perdeuteriated isobutane was prepared by reacting isobutane-2-d1 with 98.0% deuteriated sulfuric acid and was obtained in a total yield of 98.0% (chemical purity: 99.8% and isotopic purity: 97.9%).

Activation of benzene carbon-hydrogen bonds via photolysis or thermolysis of (η5-C5Me5)2Zr(alkyl)H. Isolation of (η5-C5Me5)2Zr(C 6H5)H and its conversion to a complex containing a tetramethylfulvene ligand

A new high-yield synthesis of Cp*2ZrH2 (Cp* = η5-C5Me5) is described, and olefin insertion into its Zr-H bond is used to prepare several new Cp*2Zr(alkyl)H complexes. Photolysis or thermolysis of Cp*2Zr(alkyl)H in benzene yields the respective alkane by intramolecular reductive elimination of the cis alkyl and hydride ligands, as well as the benzene C-H bond activation product Cp*2Zr(C6H5)H. Photochemically induced reductive elimination is also observed for Cp*2Zr(C6H5)H and Cp*2ZrH2. Deuterium-labeling experiments show that hydrogen exchange between the hydride and Cp* methyl groups occurs in both Cp*2Zr(H)CH2CH(CH3)2 and Cp*2Zr(C6H5)H. An additional exchange process in Cp*2Zr(C6H5)H involves the hydride ligand and an ortho phenyl hydrogen atom. Thermolysis of Cp*2Zr(C6H5)H in benzene causes quantitative evolution of dihydrogen and reversibly forms the tetramethylfulvene complex Cp*(η6-C5Me4CH2)Zr(C 6H5). Reaction of this compound with iodine produces the Cp* ring substituted phenyl iodide Cp*(η5-C5Me4CH2I)Zr(C 6H5)I. Several of the transformations involving Cp*2Zr(C6H5)H are believed to proceed via β-hydrogen elimination from the phenyl group to yield a benzyne dihydride intermediate.

Secondary Hydrogen Isotope Effect in the Unimolecular Decomposition of 2-Methylpropane Radical Cations

The intensities of the mass spectral metastable peaks for loss of methane from 2-methylpropane-1,1,1,3,3,3-d6 reveal a strong secondary hydrogen isotope effect, in that the rate of loss of CH3D is approximately an order of magnitude greater than the rate of loss of CD3H, which in turn is several times greater than the rate of loss of CD4.This isotope effect is interpreted in terms of a nonclassical transition state involving a three-center bond.This nonclassical structure is analogous to the transition state containing a three-center two-electron bond, belived to be involved in the reaction of 2-methylpropane with superacids.Photoionization appearance energies, determined for the molecular and fragment ions from 2-methylpropane, 2-methylpropane-2-d1, and 2-methylpropane-1,1,1,3,3,3-d6, and detailed rate calculations provide support for the nonclassical structure.