19550-89-1

Basic information

• Product Name: 2,2-DIMETHYL-5-HEXEN-3-OL
• Synonyms: 2,2-DIMETHYL-5-HEXEN-3-OL
• CAS NO: 19550-89-1
• Molecular Formula: C₈H₁₆O
• Molecular Weight: 128.21
• Mol File: 19550-89-1.mol
• Article Data: 54

Chemical Properties

• Boiling Point: 166.5°Cat760mmHg
• Flash Point: 61.2°C
• Appearance: /
• Density: 0.834g/cm³
• Vapor Pressure: 0.592mmHg at 25°C
• Refractive Index: 1.437
• CAS DataBase Reference: 2,2-DIMETHYL-5-HEXEN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYL-5-HEXEN-3-OL(19550-89-1)
• EPA Substance Registry System: 2,2-DIMETHYL-5-HEXEN-3-OL(19550-89-1)

Safety Data

• Hazardous Substances Data: 19550-89-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 3497, 1982 DOI: 10.1016/S0040-4039(00)87651-0

InChI:InChI=1/C8H16O/c1-5-6-7(9)8(2,3)4/h5,7,9H,1,6H2,2-4H3

Upstream product

• 630-19-3 pivalaldehyde 
• 107-05-1 3-chloroprop-1-ene 
• 2245-30-9 1,2-epoxy-3,3-dimethylbutane 
• 1774-47-6 trimethylsulfoxonium iodide 
• 141398-74-5 5,5-dimethyl-4-(trimethylsilyloxy)hex-1-ene 
• 598-98-1 Methyl pivalate 
• 762-72-1 allyl-trimethyl-silane 
• 591-87-7 Allyl acetate 
• 1730-25-2 allylmagnesium bromide 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 18854-66-5 tris(allyl)aluminum 
• 3066-75-9 allyl diethyl phosphate 
• 2622-05-1 allylmagnesium bromide 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 122293-90-7 (R)-2,2-dimethyl-5-hexen-3-yl (R)-(+)-α-methoxy-α-(trifluoromethyl)phenylacetate 
• 596851-25-1 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-tert-butyl-but-3-enyl ester 
• 140135-84-8 1-t-butyl-3-butenyl benzoate 
• 1443336-57-9 (2,2-dimethylhex-5-en-3-yloxy)diphenylsilane 

Relevant articles and documents

Allylation of Aldehydes with Allyltin Compounds in Acidic Aqueous Media-A Catalytic Version

Allylation reaction of aldehydes with allyltributyltin was achieved using Sn catalysts in acidic aqueous media. Exclusive aldehyde selectivity was observed for competitive reactions of aldehydes and ketones with allyltributyltin in the presence of 5 mol%

Gold(I)-Catalyzed Intramolecular Dehydrative Amination of Sulfamate Esters Tethered to Allylic Alcohols: A Strategy for the Synthesis of Cyclic Sulfamidates

An efficient synthesis protocol for cyclic sulfamidates has been developed via catalytic intramolecular cyclizations of sulfamate esters tethered to allylic alcohols. The reactions proceed smoothly at room temperature in the presence of (IPr)AuCl (5 mol%) and AgBF4 (5 mol%). This protocol features good to excellent yields, high selectivity, broad substrate scope, and mild reaction conditions. This method is also applicable to the synthesis of a seven-membered sulfamidate. (Figure presented.).

Stereoselective Barbier-Type Allylations and Propargylations Mediated by CpTiCl3

CpTiCl2, prepared in situ by manganese reduction of CpTiCl3, is an excellent new system for the Barbier-type allylation and propargylation of carbonyl compounds. It can be used in catalytic amounts when combined with Et3N·HBr/TMSBr, which acts as a regenerating system. The high regio- and stereoselectivity shown by this system makes it useful for prenylation and crotylation processes in the synthesis of natural products.

Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction

The ruthenium-catalyzed allylation of aldehydes with allylic pro-nucleophiles has been demonstrated to be an efficient means to form carbon-carbon bonds under mild conditions. The evolution of this reaction from the initial serendipitous discovery to its general synthetic scope is detailed, highlighting the roles of water, CO, and amine in the generation of a more complete catalytic cycle. The use of unsymmetrical allylic pro-nucleophiles was shown to give preferential product formation through the modulation of reaction conditions. Both (E)-cinnamyl acetate and vinyl oxirane were efficiently used to form the anti-branched products (up to >20:1 anti/syn) and E-linear products (up to >20:1 E/Z) in high selectivity with aromatic, α,β-unsaturated, and aliphatic aldehydes, respectively. Attempts to render the reaction enantioselective are highlighted and include enantioenrichment of up to 75:25 for benzaldehyde.