13679-86-2

Basic information

• Product Name: FEMA 3759
• Synonyms: 2-ethenyltetrahydro-2-methyl-5-(1-methylethenyl)-Furan;2-Methyl-2-vinyl-5-isopropenyltetrahydrofuran;Tetrahydro-5-isopropenyl-2-methyl-2-vinylfuran;DEHYDROXY LINALOOL OXIDE;FEMA 3759;5-ISOPROPENYL-2-METHYL-2-VINYL TETRAHYDROFURAN;FURAN,2-ETHENYLTETRAHYDRO-2-METHYL-5-(1-METHYLETHENYL)-;2-Isopropenyl-5-methyl-5-vinyltetrahydrofuran (mixture of isomers)
• CAS NO: 13679-86-2
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 237-184-9
• Mol File: 13679-86-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 55°C/11mmHg(lit.)
• Flash Point: 52.1°C
• Appearance: /
• Density: 0.925g/cm³
• Vapor Pressure: 1.58mmHg at 25°C
• Refractive Index: 1.4500 to 1.4550
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: Chlorofom (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: FEMA 3759(CAS DataBase Reference)
• NIST Chemistry Reference: FEMA 3759(13679-86-2)
• EPA Substance Registry System: FEMA 3759(13679-86-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: UN 1993 3/PG III
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 13679-86-2(Hazardous Substances Data)

Usage

Description

5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran has a pungent, herbaceous, green, boldo-like camphoraceous, piney, terpene-like, and slightly cineol-like odor.

Chemical Properties

Different sources of media describe the Chemical Properties of 13679-86-2 differently. You can refer to the following data:
1. 5-Isopropenyl-2-methyl-2-vinyltetrahydrofuran has a pungent, herbaceous-green, bold-like camphoraceous, piney, terpene-like and slightly cineol-like odor.
2. A dehydrated linalool oxide, 2-methyl-2-vinyl-5-isopropenyltetrahydrofuran, occurs naturally; it has a minty eucalyptol odor and is used in perfumery.

Occurrence

Reported found in passion fruit, muscat grape, white wine, coffee, geranium oil, cognac, grapefruit juice, coriander seed, lemon balm, clary sage, and bitter orange peel oil.

InChI:InChI=1/C10H16O/c1-5-10(4)7-6-9(11-10)8(2)3/h5,9H,1-2,6-7H2,3-4H3

Upstream product

• 67-56-1 methanol 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 71328-53-5 5-(1'-bromo-1'-methyl) ethyl-2-methyl-2-vinyltetrahydrofurane 
• 97277-67-3 1-(5-ethynyl-5-methyl-2-tetrahydrofuranyl)-1-methylethanol 
• 74026-67-8 5-(3,3-Dimethyl-oxiranyl)-3-methyl-pent-1-yn-3-ol 
• 29171-20-8 3,7-dimethyloct-6-en-1-yn-3-ol 
• 60047-17-8 2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran 
• 97277-68-4 xanthate of 1-(5-ethenyl-5-methyl-2-tetrahydrofuranyl)-1-methylethanol 
• 118989-24-5 5-ethenyl-5-methyl-2-<1-methyl-1-(phenylseleno)ethyl>tetrahydrofuran 
• 74514-23-1 6-chloro-3,7-dimethylocta-1,7-dien-3-ol 
• 29414-55-9 6,7-epoxymyrcene 

Downstream Products

• 67304-14-7 2-methyl-2-vinyl-5-isopropylidenetetrahydrofuran 
• 19822-67-4 2,2,5-trimethylcyclohept-4-en-1-one 

Relevant articles and documents

CHLORATION ALLYLIQUE D'OLEFINES DE TYPE ISOPRENIQUE A L'AIDE DU CHLORURE DE SULFURYLE

Sulfuryl chloride is a convenient reagent for the allylic chlorination of olefins bearing an isopropenyl or isopropylidenyl moiety.The substitution occurs with good yields and with allylic rearrangement, giving in most cases a secondary chloride.

Simple synthesis of karahanaenone

Karahanaenone 1 has been prepared from linalool 3. Linalool 3 is cyclized to the corresponding tetrahydrofuran-type cyclic ethers 4a-c on treatment with PhSeCl, N-bromosuccinimide, and 3-chloroperbenzoic acid, respectively. 4a-c on further treatment with various reagents, provide allylic cyclic ether 6 which is converted to 1 via 2.

Synthesis of Karahanaenone

Karahanaenone (1) has been prepared from dehydrolinalyl acetate.Electrochemical epoxidation of dehydrolinalyl acetate provided the corresponding epoxide 6a (75percent) which was converted to keto acetate 7a (82percent) by an electrogenerated acid-catalyzed rearrangement.Hydrogenation followed by alkaline hydrolysis gave 6-hydroxy-2,6-dimethyl-7-octen-3-one (7c) (86percent), which was subjected to thermal dehydration at 200 deg C to give 1 (85percent) via Claisen type rearrangement of the intermediate 2-methyl-2-ethenyl-5-propylidenetetrahydrofuran (2).An alternative route to 1 via thermolysis of the xanthate of 1-(5-ethenyl-5-methyl-2-tetrahydrofuranyl)-1-methylethanol (10b) is also described.