107-54-0

Basic information

• Product Name: 3,5-DIMETHYL-1-HEXYN-3-OL
• Synonyms: SURFYNOL 61;DIMETHYL HEXYNOL;(+/-)-3,5-DIMETHYL-1-HEXYN-3-OL;3,5-DIMETHYL-1-HEXYN-3-OL;3,5-DIMETHYL-1-HEXYNE-3-OL;3,5-dimethyl-1-hexyl-3-ol;3,5-dimethyl-1-hexyn-3-o;Surfynol
• CAS NO: 107-54-0
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.2
• EINECS: 203-500-9
• Product Categories: Acetylenes;Acetylenic Alcohols & Their Derivatives;Alkynes;Organic Building Blocks;Terminal;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 107-54-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: -39°C (estimate)
• Boiling Point: 150-151 °C(lit.)
• Flash Point: 112 °F
• Appearance: clear colorless to yellowish liquid
• Density: 0.859 g/mL at 25 °C(lit.)
• Vapor Density: 4.34 (vs air)
• Vapor Pressure: 4.5 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.434(lit.)
• Storage Temp.: Flammables area
• PKA: 13.34±0.29(Predicted)
• Water Solubility: 11.6g/L at 20℃
• CAS DataBase Reference: 3,5-DIMETHYL-1-HEXYN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHYL-1-HEXYN-3-OL(107-54-0)
• EPA Substance Registry System: 3,5-DIMETHYL-1-HEXYN-3-OL(107-54-0)

Safety Data

• Hazard Codes: T
• Statements: 10-23/24/25-36
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 1986 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 107-54-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellowish liquid

Uses

3,5-Dimethyl-1-hexyn-3-ol may be used to synthesize:3,5-Dimethyl-1-phenyl-1-hexen-3-ol via one-pot palladium-mediated hydrostannylation/Stille cross-coupling.3,5-dimethyl-1-hexyn-3-acetate via esterification with acetic anhydride in a neutral ionic liquid (1-butyl-3-methylimidazolium tetrafluoroborate).3,5-Dimethyl-3-hydroxy-1-hexen-1-yl benzoate via anti-Markovnikov addition of benzoic acid.

General Description

Bimolecular rate constant for the reaction of the hydroxyl radical (OH) with 3,5-dimethyl-1-hexyn-3-ol has been been measured using the relative rate technique. Reaction of CO2 with 3,5-dimethyl-1-hexyn-3-ol catalyzed by CuCl in different ionic liquids and solvents has been investigated.

InChI:InChI=1/C8H14O/c1-5-8(4,9)6-7(2)3/h1,7,9H,6H2,2-4H3/t8-/m0/s1

Upstream product

• 60-29-7 diethyl ether 
• 108-10-1 4-methyl-2-pentanone 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 17963-43-8 3-Hydroxy-3,5-dimethyl-1-trimethylsilyl-heptin-⁽¹⁾ 
• 4301-14-8 acetylenemagnesium bromide 
• 74-86-2 acetylene 
• 1066-26-8 sodium acetylide 

Downstream Products

• 126-86-3 2,4,7,9-tetramethyl-5-decyne-4,7-diol 
• 3329-48-4 3,5-dimethyl-hex-1-en-3-ol 
• 1423-60-5 methyl ethynyl ketone 
• 108-10-1 4-methyl-2-pentanone 
• 67-64-1 acetone 
• 78-98-8 2-oxopropanal 
• 88245-74-3 (E)-3,5-dimethyl-3-hexen-1-yne 
• 51006-81-6 (Z)-3,5-dimethyl-3-hexen-1-yne 
• 1338443-12-1 (E)-1-(dimethyl(phenyl)silyl)-3,5-dimethylhex-1-en-3-ol 

Relevant articles and documents

Base-Catalyzed Borylation/B-O Elimination of Propynols and B2pin2 Delivering Tetrasubstituted Alkenylboronates

An efficient approach to tetrasubstituted alkenylboronates via a cascade borylation/B-O elimination of propynols and B2pin2 was disclosed. A series of tetrasubstituted alkenylboronates were readily furnished with this strategy in good yields, with further transformations leading to tetrasubstituted alkenes and β-diketones demonstrating the synthetic potential of the alkenylboronates constructed by this strategy as versatile intermediates in organic synthesis.

Method for the combined production of tetramethyldecyndiol and dimethylhexynyl alcohol

A method for co-producing tetramethyldecyndiol and dimethylhexynyl alcohol, using 4-methyl-2-pentanone and acetylene as raw material, potassium hydroxide as a catalyst, and organic solvent as a dispersant, first reacting 4-methyl-2-pentanone with acetylene at atmospheric pressure or low pressure at a lower temperature to form a dimethylhexynyl alcohol-potassium hydroxide complex, and then mixing it with 4-methyl-2-pentanone quickly reacts through a high-temperature reaction tube to generate tetramethyldyne glycol. After the reaction product is water-relieved of potassium hydroxide, each target product is collected by fractionation. The present invention has the characteristics of short reaction time, low catalyst consumption and easy recovery of products.

Alkynylation of aldehydes and ketones using the Bu4NOH/H 2O/DMSO catalytic composition: A wide-scope methodology

The Favorsky reaction of a wide range of aldehydes and ketones with alkynes has been implemented under mild conditions (5-20 C). Using a Bu 4NOH/H2O/DMSO catalytic system, propargylic alcohols are formed cleanly in 39-93% (mostly 72-93%) yields and with ca. 100% selectivity. The method is suitable for aliphatic, aromatic, and heteroaromatic aldehydes and ketones, and for aliphatic, aromatic, and functionalized acetylenes. Thus, this represents the most general and efficient protocol to achieve the Favorsky reaction. Copyright