918-82-1

Basic information

• Product Name: 3,3-diMethylpent-1-yne
• Synonyms: 3,3-diMethylpent-1-yne
• CAS NO: 918-82-1
• Molecular Formula: C₇H₁₂
• Molecular Weight: 96.17018
• EINECS: -0
• Mol File: 918-82-1.mol

Chemical Properties

• Melting Point: -88.73°C (estimate)
• Boiling Point: 70°C
• Flash Point: °C
• Appearance: /
• Density: 0.7032
• Vapor Pressure: 132mmHg at 25°C
• Refractive Index: 1.3908
• CAS DataBase Reference: 3,3-diMethylpent-1-yne(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-diMethylpent-1-yne(918-82-1)
• EPA Substance Registry System: 3,3-diMethylpent-1-yne(918-82-1)

Safety Data

• Hazardous Substances Data: 918-82-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3,3-dimethylpent-1-yne is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, such as cross-coupling and addition reactions, which are crucial for constructing complex organic molecules and pharmaceutical compounds.
Used in Chemical Research:
In the field of chemical research, 3,3-dimethylpent-1-yne serves as a model compound to study the properties and reactivity of alkynes. Its unique structure allows researchers to investigate the effects of methyl group substitution on the triple bond's chemical behavior and to develop new synthetic methodologies.
Used in Industrial Production:
3,3-dimethylpent-1-yne is employed in the industrial production of various chemicals and materials. Its versatility in organic synthesis makes it a valuable intermediate in the synthesis of specialty chemicals, pharmaceuticals, and polymers, contributing to the development of new products and technologies.

InChI:InChI=1/C7H12/c1-5-7(3,4)6-2/h1H,6H2,2-4H3

Upstream product

• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 925-90-6 ethylmagnesium bromide 
• 6130-99-0 1,1-dichloro-3,3-dimethyl-pentane 
• 97-93-8 triethylaluminum 
• 6214-32-0 1-bromo-3-methylbuta-1,2-diene 
• 20669-04-9 3,3-dimethyl-2-pentanone 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 594-36-5 2-methyl-2-butylchloride 

Relevant articles and documents

Six- and eightfold palladium-catalyzed gross-coupling reactions of hexa- and octabromoarenes

Palladium-catalyzed sixfold coupling of hexabromobenzene (20) with a variety of alkenylboronates and alkenylstannanes provided hexaalkenylbenzenes 1 in up to 73% and 16 to 41% yields, respectively. In some cases pentaalkenylbenzenes 21 were isolated as the main products (up to 75%). Some functionally substituted hexaalkenylbenzene derivatives containing oxygen or sulfur atoms in each of their six arms have also been prepared (16 to 24% yield). The sixfold coupling of the less sterically encumbered 2, 3, 6, 7, 10, 11-hexabromotriphenylene (24) gave the desired hexakis(3,3-dimethyl-1-butenyl) triphenylene (25) in 93% yield. The first successful cross-coupling reaction of octabromonaphthalene (26) gave octakis-(3,3-dimethyl-1-butenyl)naphthalene (27) in 21% yield. Crystal structure analyses disclose that, depending on the nature of the substituents, the six arms are positioned either all on the same side of the central benzene ring as in 1a and 1i, making them nicely cup-shaped molecules, or alternatingly above and below the central plane las in 1h and 23. In 27, the four arms at C-1, 4, 6, 7 are down, while the others are up, or vice versa. Upon catalytic hydrogenation, 1a yielded 89% of hexakis(tert-butylethyl)benzene (23). Some efficient accesses to alkynes with sterically demanding substituents are also described. Elimination of phosphoric acid from the enol phosphate derived from the corresponding methyl ketones gave 1-ethynyladamantane (3b, 62% yield), 1-ethynyl-1-methylcyclohexane (3c, 85%) and 3,3-dimethylpentyne (3e, 65%). 1-(Trimethylsilyl)ethynylcyclopropane (7) was used to prepare 1-ethynyl-1-methylcyclopropane (3d) (two steps, 64% overall yield). The functionally substituted alkynes 3 f-h were synthesized in multistep sequences starting from the propargyl chloride 11, which was prepared in high yields from the dimethylpropargyl alcohol 10 (94%). The alkenylstannanes 19 were prepared by hydrostannation of the corresponding alkynes in moderate to high yields (42-97%), and the alkenylboronates 2 and 4 by hydroboration with catecholborane (27-96% yield) or pinacolborane (26-69% yield).

REACTIONS OF 3-ALKYL- AND 3,3-DIALKYL-1-BROMOALLENES WITH ORGANOCUPRATES: EFFECTS OF THE NATURE OF THE CUPRATE REAGENT ON THE REGIO- AND STEREOSELECTIVITY

Organocuprates induce 1,3- and direct substitution in 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes leading respectively to either terminal acetylenes or allenic hydrocarbons.The nature of the cuprate exerts a prominent role in determining both the regio- and the stereochemistry of these reactions.

MAIN GROUP METAL CHEMISTRY. REACTION OF 3,3-DIALKYL-1-BROMOALLENES WITH ALUMINIUM, ZINC, AND MAGNESIUM REAGENTS

The reactions between 1-bromo-3-methyl-1,2-pentadiene and isobutyl compounds of main group metals (Al, Zn, Mg) provide reduction, elimination, and alkylation products with chemo- and regioselectivity depending on the nature of the organometallic reagent.