3725-05-1

Basic information

• Product Name: 2,5-dimethylhexa-1,5-dien-3-yne
• Synonyms: 1,5-Hexadien-3-yne, 2,5-dimethyl-; Hexa-1,5-diene-3-yne, 2,5-dimethyl-
• CAS NO: 3725-05-1
• Molecular Formula: C₈H₁₀
• Molecular Weight: 106.165
• Mol File: 3725-05-1.mol

Chemical Properties

• Boiling Point: 125.4°C at 760 mmHg
• Flash Point: 16.7°C
• Density: 0.794g/cm³
• Vapor Pressure: 14.8mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: 2,5-dimethylhexa-1,5-dien-3-yne(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-dimethylhexa-1,5-dien-3-yne(3725-05-1)
• EPA Substance Registry System: 2,5-dimethylhexa-1,5-dien-3-yne(3725-05-1)

Safety Data

• Hazardous Substances Data: 3725-05-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,5-dimethylhexa-1,5-dien-3-yne is used as a building block in organic synthesis for the production of various types of polymers and pharmaceuticals. Its unique structure allows for the creation of a wide range of organic compounds, making it a valuable component in the synthesis of complex molecules.
Used in Chemical Research:
Due to its reactivity and versatility, 2,5-dimethylhexa-1,5-dien-3-yne is also used in chemical research. Researchers can utilize this compound to study various chemical reactions and mechanisms, contributing to the advancement of knowledge in organic chemistry.
Used in Industrial Processes:
2,5-dimethylhexa-1,5-dien-3-yne is employed in industrial processes for the production of various chemical products. Its ability to form different types of organic compounds makes it a useful intermediate in the synthesis of a range of industrial chemicals.

Upstream product

• 70947-32-9 2,5-dibromo-2,5-dimethyl-3-hexyne 
• 104-15-4 toluene-4-sulfonic acid 
• 142-30-3 2,5-dihydroxy-2,5-dimethyl-3-hexyne 
• 5455-94-7 2,2,5,5-tetramethyltetrahydro-3-oxofuran 
• 86119-84-8 phosphoric acid 
• 7664-93-9 sulfuric acid 
• 67-56-1 methanol 
• 69895-45-0 4-dichloromethylene-3,3,5,5-tetramethyl-1-pyrazoline 

Downstream Products

• 592-13-2 2,5-dimethylhexane 
• 692-70-6 (E)-2,5-dimethylhex-3-ene 
• 27296-48-6 4-(1,1,4-trimethyl-pent-4-en-2-ynyl)-phenol 
• 56412-11-4 3,6-Dimethylthienol<3,2-b>thiophen 
• 2348-27-8 Hexaisopropenylbenzol 
• 293768-61-3 1-butyl-2-hex-1-ynyl-3-isopropenyl-5-methyl-benzene 
• 2696-26-6 2,5-dimethylhex-5-en-3-yn-2-ol 
• 1621434-15-8 1,2-di(prop-1-en-2-yl)-3-(4-methoxyphenyl)cyclobutene 

Relevant articles and documents

Double dehydro-diels-alder reactions of 1,5-dien-3-ynes

A study was conducted to demonstrate double dehydro-diels-alder reactions of 1,5-dien-3-ynes. It was demonstrated that the reaction proceeded through two concerted cycloadditions, the first of which was proposed to be reversible. Detailed analysis reveale

Keto ethers. IV. Products formed on reaction of dihydro-2,2,5,5-tetramethyl-3(2H)-furanone with strong acids

Reaction of tetrahydro-2,2,5,5-tetramethyl-3(2H)-furanone (1) with 96 or ca. 100percent sulfuric acid or hot polyphosphoric acid followed by aqueous quenching gave the following products: 2-hydroxy-2,5-dimethyl-4-hexen-3-one (3), 2,4,4-trimethyl-2-cyclopenten-1-one (7), 3,5,5-trimethyl-2-cyclopenten-1-one (8), tetrahydro-2,3,5,5-tetramethylfuran-2,3-diol (11), 2,5-dihydro-3,5,5-trimethyl-2-methylenefuran (17) and its dimer 20, 2,5-dihydro-2,3,5,5-tetramethyl-2-furanol (18), 4-hydroxy-2,4-dimethyl-2-pentenoic acid γ-lactone (22), 2,3,5-trimethyl-2-cyclopenten-1-one (23), and tetramethylfuran (25).In 96percent sulfuric acid the products arise by ring opening, ring opening followed by reclosure to carbocyclic products, methyl migration from C-2 to C-3 to give rearranged furan derivatives, and oxidation.In ca. 100percent sulfuric acid or hot polyphosphoric acid further methyl migrations can occur to give 23 and 25.

The Pyrolysis of 4-Alkylidene-3,3,5,5-tetramethyl-1-pyrazolines

The pyrolysis of 4-alkylidene-3,3,5,5-tetramethyl-1-pyrazolines normally gives alkylidene-2,2,3,3-tetramethylcyclopropanes and at higher temperature or longer reaction times conjugated dienes .In some cases interesting variations occur.Foe example, 3,3,5,5-tetramethyl-1-pyrazolin-4-ylidenemalonitrile (22) gives (eventually) 3-cyano-4-isopropenyl-5-methylpyridine (27) and in the dichloro-substituted series a rearrangement from 2,2-dichloro-3,3-dimethylisopropylidenecyclopropane (30) to 3,4-dichloro-3,5-dimethylhexa-2,4-diene (31) and a double HCl elimination to give 2,5-dimethylhexa-1,5-dien-3-yne (32) are observed.The kinetics of nitrogen elimination have been determined for ten differently substituted pyrazolines (33).The reactions have positive entropies of activation and hence seems to pass through a singlet rather than (as suggested in analogous systems) a triplet intermediate but it is difficult to be sure whether this is a TMM biradical (simultaneous cleavage of both C-N bonds) or a diazenyl biradical (sequential cleavage of the C-N bonds).It is, however, interesting to note that there is no correlation between the reaction rate and the radical-stabilizing ability of the substituents X and Y on the alkylidene group.This, in turn, suggests little or no rotation of the CMe2 groups at the transition state and possibly the formation of a bis-orthogonal TMM (47) or a monoorthogonal diazenyl biradical (48).