73908-04-0

Basic information

• Product Name: 3-broMo-3-ethylpentane
• Synonyms: 3-broMo-3-ethylpentane
• CAS NO: 73908-04-0
• Molecular Formula: C₇H₁₅Br
• Molecular Weight: 179.098
• Mol File: 73908-04-0.mol

Chemical Properties

• Boiling Point: 55 °C(Press: 15 Torr)
• Appearance: /
• Density: 1.138±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 3-broMo-3-ethylpentane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-broMo-3-ethylpentane(73908-04-0)
• EPA Substance Registry System: 3-broMo-3-ethylpentane(73908-04-0)

Safety Data

• Hazardous Substances Data: 73908-04-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Bromo-3-ethylpentane is utilized as a reagent in various organic synthesis processes, serving as a key intermediate for the production of a range of chemical compounds. Its unique structure allows for versatile reactions and transformations, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Chemical Research:
In the field of chemical research, 3-broMo-3-ethylpentane is employed as a model compound to study various chemical reactions and mechanisms. Its predictable reactivity and structural features make it an ideal candidate for understanding reaction pathways and developing new synthetic methodologies.
Used in Laboratory Education:
3-Bromo-3-ethylpentane is also used in laboratory education to teach students about the properties and reactions of brominated alkanes. It provides a practical example of how functional groups and structural features influence the behavior of organic compounds, enhancing the learning experience in organic chemistry courses.
Used in Industrial Applications:
Although primarily used in research and synthesis, 3-broMo-3-ethylpentane may also find applications in specific industrial processes where its unique properties are required. These applications can include the production of specialty chemicals, materials, or as a component in the formulation of certain products.

Upstream product

• 17603-21-3 1,1-diethyl-propylium 
• 16799-08-9 1-(2-bromoethyl)-3-methylbenzene 
• 35354-15-5 2,2-diethylbutanoyl chloride 
• 597-49-9 3-ethylpentan-3-ol 

Downstream Products

• 17302-02-2 3,3-Diaethyl-hexan 
• 64277-86-7 4-(1,1-Diethyl-propyl)-benzoic acid methyl ester 
• 816-79-5 3-ethyl-2-pentene 
• 6299-66-7 4-ethylhexanoic acid 
• 4170-84-7 (1,1-diethyl-propyl)-benzene 
• 617-78-7 3-ethylpentane 
• 142-82-5 n-heptane 
• 1527-99-7 n-butyltrimethyltin 
• 10035-10-6 hydrogen bromide 
• 80025-09-8 (3,3-diethylpent-1-yn-1-yl)benzene 

Relevant articles and documents

Direct halogenation of alcohols with halosilanes under catalyst- and organic solvent-free reaction conditions

A chemoselective method for the direct halogenation of different types of alcohols with halosilanes under catalyst- and solvent-free reaction conditions (SFRC) is reported. Various primary, secondary and tertiary benzyl alcohols and tertiary alkyl alcohols were directly transformed to the corresponding benzyl and alkyl halides, respectively, using chlorotrimethylsilane (TMSCl) and bromotrimethylsilane (TMSBr).

Nucleophilic solvent participation in the solvolysis of tertiary bromoalkanes

The solvolysis of 2-bromo-2-methylpropane (1B), 2-bromo-2-methylbutane (2B), 2-bromo-2,3-dimethylbutane (3B), 2-bromo-2,3,3-trimethylbutane (4B), 3-bromo-3-methylpentane (5B), 3-bromo-2,3-dimethylpentane (6B), 3-bromo-2,2,3-trimethylpentane (7B), 3-bromo-3-ethylpentane (8B), 3-bromo-3-ethyl-2-methylpentane (9B) and 2-bromo-2,4,4-trimethylpentane (11B) in 15 to 21 solvents was studied, and correlation analyses by using the single- and dual-parameter Grunwald-Winstein equations (Eqns 1 and 2) were examined. Substrates 7B, 9B and 11B showed excellent linear relationship (R ≥ 0.997) in the logk - YBr plots and indicated limiting SN1 mechanism for the solvolysis. On the other hand, bromides 1B-6B and 8B gave linear correlations (R = 0.987-0.996) with the dual-parameter (YBr and NOTs) equation (2) only, which indicated the presence of significant nucleophilic solvent participation. Normal trends of reactivity due to the relief of B-strain could be found in the poorly nucleophilic trifluoroethanol. Similar to the corresponding chlorides, the overwhelming influence of nucleophilic solvent assistance results in the observed inverse order of reactivity: k(2B) > k(3B), k(5B) > k(6B) and k(8B) > k(9B).

Conversion of alcohols to bromides using a fluorous phosphine

Reaction of alcohols with the fluorous phosphine-carbon tetrabromide complex in toluene or in a two-phase toluene-FC-72 system afforded the corresponding bromides in good yields. The fluorous-phosphine oxide is readily separated by liquid-liquid extraction, providing an alternative to the homogeneous triphenylphosphine-carbon tetrachloride conversion, as well as to the polymer-supported phosphine method. The fluorous phosphine oxide could be reduced and the product reused.

Thermodynamic Stabilities of Phenonium Ions Based on Bromide-Transfer Equilibria in the Gas Phase

The thermodynamic stabilities of the phenonium (ethylenebenzenium) ion and ring-substituted derivatives were determined based on the bromide-transfer equilibria in the gas phase. It has been shown that the phenonium ion is 2.4 kcal mol-1 more stable than the t-butyl cation, and that the substituent effect on its stability can be correlated with the Yukawa-Tsuno equation with a ρ value of -12.6 and an r+ of 0.62. An r+ value smaller than unity of the α-cumyl(1-methyl-1-phenylethyl) cation suggested that π-delocalization in the phenonium ion is essentially less effective than through a benzylic π-interaction. On the other hand, the ρ value of -12.6 is distinctly larger than that for the ordinary benzylic carbocation systems, but is comparable to that of the benzenium ion. In addition, it has been found that the r+ value of the phenonium ions in the gas phase is in complete agreement with that for the aryl-assisted process in the acetolysis of 2-arylethyl toluenesulfonates. This suggests that the degree of π-delocalization of the positive charge is the same in the transition state and the intermediate cation. It is concluded that an r+ value of 0.6, which is ranked at a unique position in the continuous spectrum of the resonance demand, is characteristic of the bridged structure of the phenonium ion intermediate and the transition state.

DECOMPOSITION DES ESTERS DE LA N-HYDROXYTHIOPYRIDONE-2. SYNTHESE DE QUELQUES NOUVEAUX HALOGENURES SECONDAIRES ET TERTIAIRES ENCOMBRES.

Hindered α,α-disubstituted and α,α,α-trisubstituted acyl chlorides give with N-hydroxy-2-thiopyridone, the corresponding esters.The decomposition of this compound in tetrachloromethane or in bromotrichloromethane as solvent and halogen atom source results in the formation of new very hindered secondary R1R2CHX (R1 = iPr or tBu; R2 = iPr or tBu; X = Cl or Br) and tertiary R1R2R3CX (R1 = R2 = R3 = iPr; R1 = tBu, R2 = iPr, R3 = Et or Me, X = Cl) alkyl halides.

A Convenient Method for the Preparation of Highly Pure t-Alkyl Bromides and Iodides

Highly pure (99-100 percent) t-butyl and t-pentyl bromides and iodides, and 3-bromo-3-ethylpentane were readily prepared in 83-95 percent yields by the reactions of the corresponding alcohols with hydrobromic or hydroiodic acid, using lithium or calcium halide.The metal halides remarkably increased the yield and the purity of the products.