3,3-Dimethyl-1-Butyne

Base Information

• Chemical Name: 3,3-Dimethyl-1-Butyne
• CAS No.: 917-92-0
• Molecular Formula: C6H10
• Molecular Weight: 82.1454
• Hs Code.: 29012990
• European Community (EC) Number: 213-035-3
• UNII: PX4NL23U52
• DSSTox Substance ID: DTXSID70238671
• Nikkaji Number: J132.792E
• Wikidata: Q72469598
• ChEMBL ID: CHEMBL1908221
• Mol file: 917-92-0.mol

Synonyms:3,3-dimethyl-1-butyne;t-butyl acetylene

Chemical Property of 3,3-Dimethyl-1-Butyne

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 7.88 psi ( 20 °C)
• Melting Point: -78 °C
• Refractive Index: n20/D 1.374(lit.)
• Boiling Point: 37.7 °C at 760 mmHg
• Flash Point: -34 °C
• PSA: 0.00000
• Density: 0.668 g/cm³
• LogP: 1.66570
• Storage Temp.: 2-8°C
• Water Solubility.: Miscible with chloroform, benzene and toluene. Immiscible with water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 82.078250319
• Heavy Atom Count: 6
• Complexity: 73.9

Purity/Quality:

99% ^*data from raw suppliers

tert-Butylethyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F+, Xi
• Hazard Codes: F+,Xi
• Statements: 12-36/37/38
• Safety Statements: 3-16-26-33-7/9

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: CC(C)(C)C#C
• Uses: 3,3-Dimethyl-1-butyne is used as an active pharmaceutical intermediate for terbinafine. It is also used in the preparation of 2,2,7,7-tetramethyl-octa-3,5-diyne. Further, it is used in the synthesis of erythro and threo isomers of B-(3,3-dimethyl-1,2-dideuterio-1-butyl)-9-BBN by hydroboration-deuteronolysis-hydroboration sequence.

Technology Process of 3,3-Dimethyl-1-Butyne

There total 56 articles about 3,3-Dimethyl-1-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: 99.0%

2,2-dichloro-3,3-dimethylbutane (594-84-3) → 3,3-Dimethylbut-1-yne (917-92-0)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; In Petroleum ether; at 60 ℃; for 2h;

Reference yield: 91.0%

1,2-dibromo-3,3-dimethylbutane (640-21-1) → 3,3-Dimethylbut-1-yne (917-92-0)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; In Petroleum ether; at 60 ℃; for 2h;

Reference yield: 91.0%

2-cyclohexylacetylene (931-48-6) + N-benzyl-4,4-dimethylpent-2-yn-1-amine (1610010-33-7) → 3,3-Dimethylbut-1-yne (917-92-0) + N-benzyl-3-cyclohexylprop-2-yn-1-amine

Guidance literature:

With Lu(N(SiMe₃)2)3; In toluene; at 130 ℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;

DOI:10.1002/anie.201605822

upstream raw materials:

tert-butylethylene

1,1-dichloro-3,3-dimethylbutane

2,2-dichloro-3,3-dimethylbutane

2-chloro-3,3-dimethyl-1-butene

Downstream raw materials:

2,2,3,6,6-Pentamethyl-4-heptin-3-ol

4,4-dimethyl-1,1-diphenylpent-2-yn-1-ol

2,2-Dimethylbutane

Trimethylacetic acid

Refernces

• 1、 Evans, W. J.,Wajda, A. L.. "". . p. C6 - C8. Retrieved 1980.
• 2、 Laba,V.A. et al.. "". . . Retrieved 1977.
• 3、 Shao, Yinlin,Zhang, Fangjun,Zhang, Jie,Zhou, Xigeng. "Lanthanide-Catalyzed Reversible Alkynyl Exchange by Carbon–Carbon Single-Bond Cleavage Assisted by a Secondary Amino Group". supporting information. p. 11485 - 11489. Retrieved 2016/10/24.
• 4、 Capitta, Francesca,De Luca, Lidia,Porcheddu, Andrea. ""quick and click" assembly of functionalised indole rings via metal-promoted cyclative tandem reactions". . p. 59297 - 59301. Retrieved 2015/02/19.