1564-98-3

Basic information

• Product Name: 5-(3,3-Dimethyloxiranyl)-3-methyl-1-pentanol
• Synonyms: 3,7-Dimethyl-6,7-epoxy-1-octanol;3,7-Dimethyl-6,7-epoxyoctan-1-ol;3-Methyl-5-(3,3-dimethyloxiranyl)pentane-1-ol;5-(3,3-Dimethyloxiranyl)-3-methyl-1-pentanol
• CAS NO: 1564-98-3
• Molecular Formula: C₁₀H₂₀O₂
• Molecular Weight: 172.26
• Mol File: 1564-98-3.mol

Chemical Properties

• Boiling Point: 238.3°C at 760 mmHg
• Flash Point: 84.6°C
• Appearance: /
• Density: 0.935g/cm³
• Vapor Pressure: 0.00758mmHg at 25°C
• Refractive Index: 1.45
• CAS DataBase Reference: 5-(3,3-Dimethyloxiranyl)-3-methyl-1-pentanol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3,3-Dimethyloxiranyl)-3-methyl-1-pentanol(1564-98-3)
• EPA Substance Registry System: 5-(3,3-Dimethyloxiranyl)-3-methyl-1-pentanol(1564-98-3)

Safety Data

• Hazardous Substances Data: 1564-98-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-(3,3-Dimethyloxiranyl)-3-methyl-1-pentanol is used as a reagent in organic synthesis for the formation of carbon-carbon and carbon-oxygen bonds. Its ability to form these bonds makes it a valuable component in the creation of complex organic molecules.
Used in Pharmaceutical Production:
As an intermediate in the production of pharmaceuticals, 5-(3,3-Dimethyloxiranyl)-3-methyl-1-pentanol plays a crucial role in the synthesis of various medicinal compounds. Its unique structure allows it to be a key component in the development of new drugs and therapeutic agents.
Used in Fine Chemicals Industry:
5-(3,3-Dimethyloxiranyl)-3-methyl-1-pentanol is also utilized as an intermediate in the production of other fine chemicals. Its versatility and reactivity make it a valuable asset in the synthesis of specialty chemicals used in various applications.
Used in Fragrance and Flavor Industry:
Due to its unique structural properties, 5-(3,3-Dimethyloxiranyl)-3-methyl-1-pentanol has potential applications in the fragrance and flavor industry. Its distinct chemical composition may contribute to the creation of novel scents and flavors, enhancing the sensory experience in various products.

InChI:InChI=1/C10H20O2/c1-8(6-7-11)4-5-9-10(2,3)12-9/h8-9,11H,4-7H2,1-3H3

Upstream product

• 106-22-9 Citronellol 
• 67245-14-1 2,6-dimethyl-2,3-epoxy-8-(benzyloxy)octane 
• 31558-25-5 2,6-dimethyl-2,3,8-octanetriol 
• 86852-11-1 diethoxyltriphenylphosphorane 
• 94450-67-6 6-bromo-3,7-dimethyl-octane-1,7-diol 
• 61263-98-7 (+/-)-Methyl citronellate oxide 
• 5713-07-5 3,7-dimethyl-oct-7-en-1-ol 
• 1117-61-9 (3R)-citronellol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 20425-54-1 (R)-1-citronellyl acetate 
• 18951-85-4 (R)-citronellic acid 
• 25825-48-3 5-(3,3-dimethyloxiran-2-yl)-3-methylpentanal 

Downstream Products

• 70973-30-7 2,6-dimethyl-3,8-bis(trimethylsiloxy)octene 
• 22460-95-3 3,7-dimethyl-6-hydroxy-oct-7-en-1-ol 
• 84560-01-0 1-hydroxy-3,7-dimethyloctan-6-one 
• 121618-71-1 (+/-)-6,7-epoxy-3,7-dimethyloctyl-tert-butyldimethylsilylether 
• 98206-63-4 7-hydroxycitronellol 
• 70200-30-5 3,7-dimethyl-6,7-epoxyoctyl p-toluenesulfonate 
• 31558-25-5 2,6-dimethyl-2,3,8-octanetriol 
• 488820-83-3 (+/-)-7-azido-6-hydroxy-3,7-dimethyloctanol 
• 1787-98-0 6,7-epoxycitronellyl acetate 
• 488820-96-8 (+/-)-7-azido-6-hydroxy-3,7-dimethyloct-1-yl acetate 
• 488820-97-9 (+/-)-7-azido-6-hydroxy-3,7-dimethyloct-1-yl tert-butyldimethylsilyl ether 
• 26314-72-7 6-Oxo-6,7-dihydrocitronellol acetate 
• 796873-28-4 C₁₀H₂₀OS 

Relevant articles and documents

Aerobic Epoxidation of Olefins Catalyzed by Cobalt(II) Complex Using Propionaldehyde Diethyl Acetal as a Reductant

In the presence of bis(3-methyl-2,4-pentanedionato)cobalt(II) complex catalyst, various trisubstituted olefins are smoothly monooxygenated into the corresponding epoxides in high yields under neutral conditions by the combined use of molecular oxygen and propionaldehyde diethyl acetal.

NOVEL ORGANOLEPTIC COMPOUNDS

The present invention relates to novel compounds and their use as fragrance materials.

Unraveling the role of the lacunar Na7PW11O39 catalyst in the oxidation of terpene alcohols with hydrogen peroxide at room temperature

In this work, we have assessed the activity of various Keggin heteropolyacid (HPA) salts in a new one-pot synthesis route of valuable products, which were obtained from the oxidation of terpenic alcohols (i.e., aldehyde, epoxide, and diepoxide), using a green oxidant (i.e., hydrogen peroxide) at mild conditions (i.e., room temperature). Lacunar Keggin HPA sodium salts were the goal catalysts investigated in this reaction. Starting from the HPAs (H3PW12O40, H3PMo12O40, and H4SiW12O40), we synthesized lacunar sodium salts (Na7PW11O39, Na7PW11O39 and Na8SiW11O39) and a saturated salt (Na3PW12O40). All of them were investigated in oxidation reactions in a homogeneous phase with nerol as a model molecule. Na7PW11O39 was the most active and selective towards the oxidation products. All the catalysts were characterized by FT-IR, TG/DSC, BET, XRD, and SEM-EDS analyses and potentiometric titration. The main reaction parameters were assessed. Geraniol, α-terpineol, β-citronellol and borneol were also successfully oxidized. Special attention was dedicated to correlating the composition and properties of the catalysts with their activity.

Hydroxyl citronellol and preparation method thereof (by machine translation)

The invention provides hydroxyl citronellol and a preparation method thereof. The method has the advantages of high yield and less three wastes, overcomes a plurality of problems in the prior art, and has a good industrial prospect. (by machine translation)

One-pot synthesis at room temperature of epoxides and linalool derivative pyrans in monolacunary Na7PW11O39-catalyzed oxidation reactions by hydrogen peroxide

In this work, we describe a new one-pot synthesis route of valuable linalool oxidation derivatives (i.e., 2-(5-methyl-5-vinyltetrahydrofuran-2-yl propan-2-ol) (1a)), 2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol (1b) and diepoxide (1c), using a green oxidant (i.e., hydrogen peroxide) under mild conditions (i.e., room temperature). Lacunar Keggin heteropolyacid salts were the catalysts investigated in this reaction. Among them, Na7PW11O39 was the most active and selective toward oxidation products. All the catalysts were characterized by FT-IR, TG/DSC, BET, XRD analyses and potentiometric titration. The main reaction parameters were assessed. Special attention was dedicated to correlating the composition and properties of the catalysts and their activity.

Catalytic β-bromohydroxylation of natural terpenes: Useful intermediates for the synthesis of terpenic epoxides

In a one-step procedure, various β-bromoalcohols were synthesized from natural terpenes in good to excellent yields. Using different catalysts, the reaction was carried out at room temperature, with H2O as nucleophile and N-bromosuccinimide as a bromine source under mild reaction conditions. The synthesized β-bromoalcohols were subsequently converted in situ to the corresponding epoxides in good yields.

Oxidative Cleavage of Alkene C=C Bonds Using a Manganese Catalyzed Oxidation with H2O2 Combined with Periodate Oxidation

A one-pot multi-step method for the oxidative cleavage of alkenes to aldehydes/ketones under ambient conditions is described as an alternative to ozonolysis. The first step is a highly efficient manganese catalyzed epoxidation/cis-dihydroxylation of alkenes. This step is followed by an Fe(III) assisted ring opening of the epoxide (where necessary) to a 1,2-diol. Carbon–carbon bond cleavage is achieved by treatment of the diol with sodium periodate. The conditions used in each step are not only compatible with the subsequent step(s), but also provide for increased conversion compared to the equivalent reactions carried out on the isolated intermediate compounds. The described procedure allows for carbon–carbon bond cleavage in the presence of other alkenes, oxidation sensitive moieties and other functional groups; the mild conditions (r.t.) used in all three steps make this a viable general alternative to ozonolysis and especially for use under flow or continuous batch conditions.

A method for preparing cis- rose ether (by machine translation)

The invention discloses a preparation method of cis-rose oxide. The preparation method comprises the following steps: performing epoxidation, epoxy rearrangement and selective oxidation on citronellol serving as a starting material, and preparing allene by using a benzenesulfonohydrazine intermediate; and cyclizing the allene under an acid condition to obtain the cis-rose oxide. By adopting the preparation method, the defects of low yield, use of various toxic reagents and metal reagents, difficulty in operating in a reaction process and the like in the conventional synthesis route are overcome, meanwhile the reaction stereoselectivity is improved, and synthesis of the cis-rose oxide can be realized. In particular, the using amount of aluminum isopropoxide is reduced; acetone, p-benzoquinone and the like are taken as oxidants, so that the production cost can be lowered effectively, greater convenience is brought to application, and industrial large-scale production is facilitated; and meanwhile reactions in a plurality of steps are performed in the same reaction kettle in a one-pot reaction way, so that the reaction process is simplified greatly, the production cost is lowered, and industrial production is facilitated.

Selective catalytic oxidation of alcohols, aldehydes, alkanes and alkenes employing manganese catalysts and hydrogen peroxide

The manganese-containing catalytic system [MnIV,IV 2O3(tmtacn)2]2+ (1)/carboxylic acid (where tmtacn=N,N′,N′′-trimethyl-1,4,7-triazacyclononane), initially identified for the cis-dihydroxylation and epoxidation of alkenes, is applied for a wide range of oxidative transformations, including oxidation of alkanes, alcohols and aldehydes employing H2O2 as oxidant. The substrate classes examined include primary and secondary aliphatic and aromatic alcohols, aldehydes, and alkenes. The emphasis is not primarily on identifying optimum conditions for each individual substrate, but understanding the various factors that affect the reactivity of the Mn-tmtacn catalytic system and to explore which functional groups are oxidised preferentially. This catalytic system, of which the reactivity can be tuned by variation of the carboxylato ligands of the in situ formed [MnIII,III 2(O)(RCO2)2(tmtacn)2]2+ dimers, employs H2O2 in a highly atom efficient manner. In addition, several substrates containing more than one oxidation sensitive group could be oxidised selectively, in certain cases even in the absence of protecting groups. Copyright

Mild oxygen activation with isobutyraldehyde promoted by simple salts

Oxygen activation using an aldehyde as a sacrificial reductant and mediated by metalloporphyrins is a radical process with a variable induction period in which the macrocycle function is to generate the acyl radicals to initiate a chain mechanism. This function can be also efficiently promoted by simple metal salts, which leads to a very simple and practical oxidative system that is able to epoxidize alkenes in good yields.