2-Butyne

Base Information

• Chemical Name: 2-Butyne
• CAS No.: 503-17-3
• Molecular Formula: C4H6
• Molecular Weight: 54.0916
• European Community (EC) Number: 207-962-2
• UN Number: 1144
• UNII: LKE6D3018E
• DSSTox Substance ID: DTXSID3060116
• Nikkaji Number: J2.603D
• Wikipedia: 2-Butyne
• Wikidata: Q209336,Q83112587
• ChEMBL ID: CHEMBL119108
• Mol file: 503-17-3.mol

Synonyms:4-butyne;but-4-yne;dimethylacetylene

Chemical Property of 2-Butyne

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 745mmHg at 25°C
• Melting Point: -32 °C
• Boiling Point: 25.6°Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: 0.694g/cm³
• LogP: 1.02960
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 54.0469501914
• Heavy Atom Count: 4
• Complexity: 42.9
• Transport DOT Label: Flammable Liquid

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s): R12:Extremely flammable.; R36/37:Irritating to eyes and respiratory system.
• Hazard Codes: R12:Extremely flammable.; R36/37:Irritating to eyes and respiratory system.
• Statements: R12:Extremely flammable.; R36/37:Irritating to eyes and respiratory system.
• Safety Statements: S16:Keep away from sources of ignition - No smoking.; S23:Do not inhale gas/fumes/vapour/spray.; S29:Do not empty

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: CC#CC
• General Description: 2-Butyne, also known as Dimethylacetylene, is a linear alkyne with the molecular formula C₄H₆, featuring a triple bond between the second and third carbon atoms. It can be formed through the isomerization of but-1-yne on certain alkali-exchanged zeolites, such as CsNaX,9Cs, as demonstrated in IR studies. This transformation highlights its role in probing the basicity of zeolites, where it serves as a product of catalytic isomerization under specific conditions. Additionally, 2-butyne is referenced in the context of dimethylselenadiazole reactions, where dimethylacetylene (a synonym for 2-butyne) is produced alongside other compounds. Its structural simplicity and reactivity make it relevant in catalytic and synthetic chemistry.

Technology Process of 2-Butyne

There total 141 articles about 2-Butyne which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3,3'-dimethyl-3H,3'H-[3,3']bidiazirinyl → dimethylacetylene (503-17-3)

Guidance literature:

In chloroform; at 40 - 60 ℃;

DOI:10.1002/anie.200503124

Reference yield: 99.0%

1-Phenylprop-1-yne (673-32-5) → dimethylacetylene (503-17-3) + diphenyl acetylene (501-65-5)

Guidance literature:

With Mo(≡N)(OSiPh₃)₃(phen); manganese(ll) chloride; In toluene; at 80 ℃; for 3.5h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Molecular sieve;

Reference yield: 97.0%

(o-methoxyphenyl)-1-propyne (66021-98-5) → dimethylacetylene (503-17-3) + 2,2'-dimethoxytolane (5293-78-7)

Guidance literature:

With Mo(≡CPh)(OSiPh₃)₃.OEt₂; In toluene; at 20 ℃; for 2h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Molecular sieve;

upstream raw materials:

1-butylene

butene-2

but-1-yne

2,3-dibromobutane

Downstream raw materials:

7-acetoxy-2-(3,4-diacetoxy-phenyl)-chroman-4-one

1-Chloro-2,3-dimethyl-cycloprop-2-enecarbonyl chloride

Chloro-dimethyl-((E)-1-methyl-propenyl)-silane

1,2-dimethyl-3-trifluoromethyl-cyclopropene

Refernces

Reactions of alkynes with mononulear benzylidene complexes and with binuclear $um-benzylidene complexes of tungsten

10.1016/0304-5102(88)85100-9

The study investigates the reactions of benzylidene(pentacarbonyl)tungsten complexes, specifically (CO)5W=C(C6H4R-p)H (where R = H, Me), with various alkynes such as diethylaminopropyne (Et2NC2CMe) and 2-butyne. The benzylidene complexes act as highly reactive and electrophilic reagents. When reacting with diethylaminopropyne, the C≡C bond of the alkyne inserts into the W=C bond of the complex, forming a new complex (CO)5W=C(NEt2)-C(Me)=C(C6H4R-p)H. With 2-butyne, the reaction yields (CO)5W[MeC≡CMe] and various coupling products, but no polymerization occurs. However, when t-BuC≡CH is used in excess, rapid polymerization is observed, and a mechanism involving the initial formation of a vinylidene complex is proposed. The study also explores the thermolysis of terminal benzylidene complexes in inert solvents, which leads to the formation of benzylidene-bridged bis(pentacarbonyltungsten) complexes that can initiate the polymerization of 2-butyne. The research provides insights into the reactivity of benzylidene complexes and their potential as initiators for alkyne polymerization.