51911-82-1

Basic information

• Product Name: 4,8-dimethylnona-1,3,7-triene
• Synonyms: 4,8-dimethylnona-1,3,7-triene;4,8-Dimethyl-1,3(E),7-nonatriene;1,3,7-Nonatriene, 4,8-dimethyl-;Einecs 257-509-8
• CAS NO: 51911-82-1
• Molecular Formula: C₁₁H₁₈
• Molecular Weight: 150.26062
• EINECS: 257-509-8
• Mol File: 51911-82-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 195.6°Cat760mmHg
• Flash Point: 60.4°C
• Appearance: /
• Density: 0.782g/cm³
• Vapor Pressure: 0.582mmHg at 25°C
• Refractive Index: 1.459
• CAS DataBase Reference: 4,8-dimethylnona-1,3,7-triene(CAS DataBase Reference)
• NIST Chemistry Reference: 4,8-dimethylnona-1,3,7-triene(51911-82-1)
• EPA Substance Registry System: 4,8-dimethylnona-1,3,7-triene(51911-82-1)

Safety Data

• Hazardous Substances Data: 51911-82-1(Hazardous Substances Data)

Usage

General Description

4,8-dimethylnona-1,3,7-triene, also known as DMNT or 4,8-dimethyl-1,3,7-nonatriene, is a naturally occurring volatile organic compound that is found in a variety of plants, particularly those in the Asteraceae family. It is a type of plant hormone that is released when the plant is damaged or under stress, and it serves as a signal to nearby plants to activate their own defense mechanisms. DMNT is also involved in the attraction of certain insects, particularly predators of the herbivores that are feeding on the plant. This chemical has been found to have antimicrobial and anti-insect properties, making it useful in plant defense mechanisms. It also has potential applications in agriculture and pest control.

InChI:InChI=1/C11H18/c1-5-7-11(4)9-6-8-10(2)3/h5,7-8H,1,6,9H2,2-4H3

Synthetic route

methyl magnesium iodide (917-64-6) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
With diethyl ether erhitzt den erhaltenen Alkohol mit Essigsaeureanhydrid auf 120-130grad;

Methyltriphenylphosphonium bromide (1779-49-3) + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
(i) PhLi, Et2O, (ii) /BRN= 1721871/; Multistep reaction;

3,6,6-trimethyl-(4at,8at)-hexahydro-3r,5c-ethano-pyrano[3,4-c]pyran-1,8-dione (5988-79-4, 93354-31-5) → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
copper at 190 - 210℃; for 8h;

methylmagnesium iodide + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) + diluted acid → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
Wasserabspaltung aus dem primaer gebildeten Alkohol;

methyl magnesium (1+); bromide + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) + diluted acid → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
infolge Wasserabspaltung dem primaer gebildeten Alkohol;

pinacolboratamethylenetriphenylphosphonium iodide + (E/Z)-3,7-dimethyl-2,6-octadienal (5392-40-5) → 4,8-dimethyl-1,3,7-nonatriene (51911-82-1)

Conditions	Yield
Stage #1: pinacolboratamethylenetriphenylphosphonium iodide With lithium hexamethyldisilazane In N,N,N,N,N,N-hexamethylphosphoric triamide at 0℃; for 2h; Stage #2: (E/Z)-3,7-dimethyl-2,6-octadienal In N,N,N,N,N,N-hexamethylphosphoric triamide at -78 - 20℃;	99 % Chromat.

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + cyclohex-1-en-1-yl trifluoromethane sulfonate (28075-50-5) → C17H28

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Reagent/catalyst; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	94%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (170011-47-9) → (E)-8-(4,8-dimethylnona-3,7-dien-2-yl)-1,4-dioxaspiro[4.5]dec-7-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	88%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + C13H23F3O4SSi → tert-butyl((3-((E)-4,8-dimethylnona-3,7-dien-2-yl)cyclohex-2-en-1-yl)oxy)dimethylsilane

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	85%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + N-(4-methylphenylsulfonyl)-4-[(trifluoromethanesulfonyl)oxy]-1,2,3,6-tetrahydropyridine (606926-42-5) → (E)-4-(4,8-dimethylnona-3,7-dien-2-yl)-1-tosyl-1,2,3,6-tetrahydropyridine

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	85%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + C9H13F3O5S → (E)-6,8,12-trimethyl-5-methylenetrideca-7,11-dien-1-yl acetate

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	85%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 1-cyclopentenyl triflate (28075-49-2) → (E)-1-(4,8-dimethylnona-3,7-dien-2-yl)cyclopent-1-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	83%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 5,6-dihydro-4-trifluoromethylsulfonyloxy-2H-pyran (188975-30-6) → (E)-4-(4,8-dimethylnona-3,7-dien-2-yl)-3,6-dihydro-2H-pyran

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	81%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 7-oxo-7-(p-tolylamino)hept-1-en-2-yl trifluoromethanesulfonate → (E)-7,9,13-trimethyl-6-methylene-N-(p-tolyl)tetradeca-8,12-dienamide

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	80%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene (77412-96-5) → 4-(tert-butyl)-1-((E)-4,8-dimethylnona-3,7-dien-2-yl)cyclohex-1-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	79%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + PhCH2CH2C(=CH2)OTf → (E)-(4,6,10-trimethyl-3-methyleneundeca-5,9-dien-1-yl)benzene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	79%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + methyl 6-(((trifluoromethyl)sulfonyl)oxy)hept-6-enoate → C19H32O2

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	79%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + C23H24F4O5S → (E)-7,9,13-trimethyl-6-methylenetetradeca-8,12-dien-1-yl 2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoate

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	74%

3,6-dihydro-2H-thiopyran-4-enol trifluoromethanesulfonate (181180-42-7) + 4,8-dimethyl-1,3,7-nonatriene (51911-82-1) → (E)-4-(4,8-dimethylnona-3,7-dien-2-yl)-3,6-dihydro-2H-thiopyran

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	72%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 4-phenylcyclohex-1-enyl trifluoromethanesulfonate (122948-47-4) → C23H32

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	72%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + ethyl 4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-enecarboxylate (122948-57-6) → ethyl 4-((E)-4,8-dimethylnona-3,7-dien-2-yl)cyclohex-3-ene-1-carboxylate

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	71%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 3,4-dihydro-1-naphthyl triflate (123994-49-0) → 4-((E)-4,8-dimethylnona-3,7-dien-2-yl)-1,2,3,8a-tetrahydronaphthalene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	71%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 1-cyclooctenyl triflate (28075-35-6) → (E)-1-(4,8-dimethylnona-3,7-dien-2-yl)cyclohept-1-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	69%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + hept-1-en-2-yl trifluoromethanesulfonate → (E)-2,6,8-trimethyl-9-methylenetetradeca-2,6-diene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	63%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + cyclohept-1-en-1-yl trifluoromethanesulfonate (28075-51-6) → (E)-1-(4,8-dimethylnona-3,7-dien-2-yl)cyclohept-1-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	62%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 7-hydroxyhept-1-en-2-yl trifluoromethanesulfonate → (E)-6,8,12-trimethyl-5-methylenetrideca-7,11-dien-1-ol

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	62%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 3-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate (109459-30-5) → 3-((E )-4,8-dimethylnona-3,7-dien-2-yl)cyclohex-2-en-1-ol

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	60%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + (4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-3,4,4a,5,6,7-hexahydronaphthalen-2-yl trifluoromethanesulfonate (1346777-33-0) → (2R,8R,8aS)-6-((E)-4,8-dimethylnona-3,7-dien-2-yl)-8,8a-dimethyl-2-(prop-1-en-2-yl)-1,2,3,7,8,8a-hexahydronaphthalene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	53%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + cyclododec-1-en-1-yl trifluoromethanesulfonate (58999-91-0, 58999-92-1) → 1-(4,8-dimethylnona-3,7-dien-2-yl)cyclododec-1-ene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	47%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + Acetic acid (8R,9S,10R,13S,14S)-10,13-dimethyl-3-trifluoromethanesulfonyloxy-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (81827-59-0) → (8R,9S,10R,13S,14S)-3-((E)-4,8-dimethylnona-3,7-dien-2-yl)-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylacetate

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C35H46NP; cesium fluoride In tetrahydrofuran; di-isopropyl ether at 0℃; for 48h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	46%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + methyl 2-diazo-3-oxo-3-(pyrrolidin-1-yl)propanoate (135747-07-8) → methyl 2-((E)-2,6-dimethylhepta-1,5-dienyl)-1-(pyrrolidin-1-ylcarbonyl)cyclopropanecarboxylate (1198573-97-5)

Conditions	Yield
With tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) In 1,2-dichloro-ethane at 25℃; for 16h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	45%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) + 3-acetoxy-3-(4-methoxyphenyl)prop-1-yne (99520-55-5) → (1E,4Z)-7-(4-methoxyphenyl)-6-methyl-6-(4-methylpent-3-enyl)cyclohepta-1,4-dienyl acetate

Conditions	Yield
With [{(2-biphenyl)-di-tBu-phosphine}Au]SbF6 In 1,2-dichloro-ethane at 25 - 120℃; for 12.5h; Cope rearrangement; stereoselective reaction;	37%

4,8-dimethyl-1,3,7-nonatriene (51911-82-1) → 5-allyl-1,5-dimethyl-cyclohexene

Conditions	Yield
With sulfuric acid

Upstream product

• 917-64-6 methyl magnesium iodide 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 5988-79-4 3,6,6-trimethyl-(4at,8at)-hexahydro-3r,5c-ethano-pyrano[3,4-c]pyran-1,8-dione 
• 689-67-8 pseudo-ionone 

Downstream Products

• 1603001-86-0 (E)-N-(4,8-dimethylnona-3,7-dien-2-yl)aniline 
• 1603002-29-4 (Z)-N-(4,8-dimethylnona-3,7-dien-2-yl)aniline 

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