Myrcene supplier | CasNO.123-35-3

Name
Myrcene
EINECS 204-622-5
CAS No. 123-35-3
Article Data120
CAS DataBase
Density 0.769 g/cm³
Solubility practically insoluble in water
Melting Point <-10 °C
Formula C₁₀H₁₆
Boiling Point 167 °C at 760 mmHg
Molecular Weight 136.237
Flash Point 44.4 °C
Transport Information UN 2319 3/PG 3
Appearance clear to pale yellow liquid
Safety 16-26-36-37/39
Risk Codes 10-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1,6-Octadiene,7-methyl-3-methylene-;2-Methyl-6-methylene-2,7-octadiene;3-Methylene-7-methyl-1,6-octadiene;7-Methyl-3-methylene-1,6-octadiene;NSC 406264;b-Geraniolene;b-Myrcene;
PSA 0.00000
LogP 3.47500

Synthetic route

: 71092-51-8
(2-methylene-3-butenyl)-trimethyltin

: 870-63-3
prenyl bromide

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran at 65℃;	94%

: 4075-28-9
2-chloromethyl-1,3-butadiene

: 35189-96-9
3-methyl-2-butenylmagnesium chloride

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 10h;	92%

: 141-12-8
neryl acetate

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 2-Propynylzinc bromide In tetrahydrofuran for 3h; Ambient temperature;	90%

: 59632-99-4
geranyl 2-tetrahydropyranyl ether

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 6h; Heating;	89%
With 18-crown-6 ether; potassium tert-butylate In tetrahydrofuran at 60℃; for 12h; Inert atmosphere;	73.1%

: 72106-90-2
O-(trans-3,7-dimethylocta-2,6-dien-1-yl)trimethylsilane

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
With tetrahydrofuran; lithium diisopropylamide at -78℃; for 5h;	85%

: 70473-31-3
neryl 2-tetrahydropyranyl ether

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 18h; Heating;	83%

: 2565-83-5, 72152-72-8, 2565-82-4
geraniol methyl ether

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
With potassium tert-butylate; 18-crown-6 ether In tetrahydrofuran for 2h; Heating;	76%

: 2565-83-5
(2Z)-1-methoxy-3,7-dimethylocta-2,6-diene

LIDAKOR: LIDAKOR

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
In tetrahydrofuran at -50℃; for 1h;	76%

: 37586-57-5
4-methyl-3-pentenylmagnesium bromide

: 89228-81-9
buta-2,3-dien-1-yl diethyl phosphate

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h; Ambient temperature;	75%

: 18172-67-3, 19902-08-0
beta-pinene

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 499-97-8
pseudolimonene

C: 5989-54-8
(-)-(S)-limonene

Conditions

Conditions	Yield
In ethanol at 400℃; under 91206.1 Torr; for 0.0194444h; Product distribution; Further Variations:; Temperatures;	A 72% B 8% C n/a

...Expand

: 2565-83-5, 72152-72-8, 2565-82-4
geraniol methyl ether

LIDAKOR: LIDAKOR

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
In tetrahydrofuran at -30℃; for 15h;	66%

: 79240-18-9
6-Methyl-2-(toluene-4-sulfonyl)-2-vinyl-hept-5-en-1-ol

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 2h; Heating;	62%

: 125061-34-9
4,4,4-Trifluoro-3-oxo-butyric acid (E)-3,7-dimethyl-octa-2,6-dienyl ester

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 118453-57-9
1,1,1-trifluoro-6,10-dimethyl-undeca-5,9-dien-2-one

Conditions

Conditions	Yield
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran Heating;	A n/a B 56%

: 40267-53-6
(E)-N,N-diethyl-3,7-dimethyl-2,6-octadienylamine

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
at 130℃; under 20 Torr; for 5h;	50%

: 2-(geranyloxy)-3,5,7-trimethyltropone

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 3338-55-4
(Z)-ocimene

C: 3779-61-1
trans ocimene

D: 2885-58-7
3,5,7-trimethyltropolone

Conditions

Conditions	Yield
at 180℃; pyrolysis;	A 30% B 8% C 49% D n/a
at 140℃; pyrolysis;	A 23% B 12% C 36% D n/a

...Expand

: 35162-74-4
geranyl phenyl sulfide

: 108-24-7
acetic anhydride

: 64-19-7
acetic acid

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 105-87-3
3,7-dimethyl-2E,6-octadien-1-yl acetate

C: 3338-55-4
(Z)-ocimene

Conditions

Conditions	Yield
With lithium acetate; copper diacetate; copper at 85 - 90℃;	A n/a B 43% C n/a

...Expand

: 136918-14-4
phthalimide

: (E)-7-methylocta-5,7-dien-1-yl 4-methylbenzenesulfonate

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
With 18-crown-6 ether In N,N-dimethyl-formamide at 100℃; for 16h;	43%

: 2565-83-5
(2Z)-1-methoxy-3,7-dimethylocta-2,6-diene

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
With potassium tert-butylate; 18-crown-6 ether In tetrahydrofuran for 7h; Heating;	35%

: 2-(geranyl-oxy)tropone

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 83849-32-5
5-(3,7-dimethyl-2,6-octadienyl)tropolone

C: 3-(1,5-dimethyl-1-vinyl-4-hexenyl)tropolone

Conditions

Conditions	Yield
at 140℃; for 2h; pyrolysis; Further byproducts given;	A 3 % Chromat. B 32% C 31%

...Expand

: 2-(geranyl-oxy)tropone

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 83849-32-5
5-(3,7-dimethyl-2,6-octadienyl)tropolone

C: 3-(1,5-dimethyl-1-vinyl-4-hexenyl)tropolone

D: 78-79-5
isoprene

Conditions

Conditions	Yield
at 140℃; for 2h; pyrolysis; Further byproducts given;	A 3 % Chromat. B 32% C 31% D 10 % Chromat.

...Expand

: 78-79-5
isoprene

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
	32%
	23%
In tetrahydrofuran	15%
With sodium; N-cyclohexyl-cyclohexanamine In tetrahydrofuran Mechanism; K, Li various dialkylamines;
In tetrahydrofuran at 10℃; Rate constant; Na, dicyclohexylamine;

: 85217-72-7
geranyl methyl carbonate

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 3338-55-4
(Z)-ocimene

Conditions

Conditions	Yield
With hexacarbonyl molybdenum In toluene at 110℃; for 72h;	A 7% B 31%

: 106-23-0, 26489-02-1
3,7-dimethyl-oct-6-enal

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 13877-91-3
3,7-Dimethyl-octa-1,3,6-trien

C: 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene

D: 586-67-4
3,8-p-Menthadien

E: 138-86-3
limonene.

Conditions

Conditions	Yield
With aluminum oxide; carbon dioxide In hexane at 190℃; Supercritical conditions;	A 15.8% B 6.2% C 11.9% D 30.8% E 5.2%

...Expand

: 3,5,7-trimethyl-2-(neryloxy)tropone

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 3338-55-4
(Z)-ocimene

C: 3779-61-1
trans ocimene

Conditions

Conditions	Yield
at 140℃;	A 29% B 9% C 27%
at 140℃; pyrolysis;	A 29% B 9% C 27%

...Expand

: 106-24-1
Geraniol

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 3338-55-4
(Z)-ocimene

C: 3779-61-1
trans ocimene

D: 586-62-9
Terpinolene

E: 138-86-3
limonene.

Conditions

Conditions	Yield
With tin(ll) chloride In dimethyl sulfoxide at 139.84℃; for 2h;	A 27% B 24% C 17% D 10% E 22%

...Expand

: 106-24-1
Geraniol

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
With copper(II) sulfate In neat (no solvent) at 125℃; under 25 Torr; for 1.5h;	25%
Multi-step reaction with 3 steps 1: 86 percent 2: NaI / acetone / 1 h / 0 - 2 °C 3: triethylamine / hexane / 6 h / 25 °C / Irradiation View Scheme
With bis(acetylacetonato)palladium(II); carbon monoxide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trifluoroacetic acid In toluene at 105℃; under 30003 Torr; for 18h; chemoselective reaction;
Multi-step reaction with 2 steps 1: Castellaniella defragrans linalool dehydratase isomerase / 20 h / Enzymatic reaction 2: Castellaniella defragrans linalool dehydratase isomerase / 20 h / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C 2: potassium tert-butylate; 18-crown-6 ether / tetrahydrofuran / 12 h / 60 °C / Inert atmosphere View Scheme

: 106-23-0, 26489-02-1
3,7-dimethyl-oct-6-enal

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 99-86-5
1-methyl-4-isopropyl-1,3-cyclohexadiene

C: 586-67-4
3,8-p-Menthadien

D: 500-00-5
3-p-menthene

: 491-07-6, 1074-95-9, 1196-31-2, 3391-87-5, 10458-14-7, 14073-97-3, 18309-28-9, 36977-92-1, 117773-78-1, 89-80-5
(+/-)-menthone

Conditions

Conditions	Yield
With aluminum oxide; carbon dioxide In hexane at 190℃; Supercritical conditions;	A 6.9% B 8.2% C 21.4% D 6.3% E 6.6%

...Expand

: 2-(geranyl-oxy)tropone

A: 123-35-3
7-methyl-3-methene-1,6-octadiene

B: 3338-55-4
(Z)-ocimene

C: 3779-61-1
trans ocimene

D: 3-(1,5-dimethyl-1-vinyl-4-hexenyl)tropolone

Conditions

Conditions	Yield
at 180℃; for 15h; Further byproducts given;	A 15% B 6% C 19% D n/a
at 180℃; for 0.25h; pyrolysis; Further byproducts given;	A 15% B 6% C 19% D n/a
at 180℃; for 15h; pyrolysis; Further byproducts given;	A 15 % Chromat. B 6 % Chromat. C 19 % Chromat. D n/a

...Expand

: 75-64-9
tert-butylamine

: 108-18-9
diisopropylamine

: 78-79-5
isoprene

: 123-35-3
7-methyl-3-methene-1,6-octadiene

Conditions

Conditions	Yield
	18.6%

...Expand

: 50-00-0
formaldehyd

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 141-97-9
ethyl acetoacetate

: ethyl 1-acetyl-4-(4-methylpent-3-en-1-yl)cyclohex-3-enecarboxylate

Conditions

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran at 70℃; for 48h; Diels-Alder Cycloaddition; Sealed tube;	100%

...Expand

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 292638-85-8
acrylic acid methyl ester

: 53311-89-0
1(4-methyl-3-pentenyl)-4-carbmethoxy-cyclohex-1-ene

Conditions

Conditions	Yield
With K10 supported ecological catalyst (0.1equiv. Zn) In toluene at 110℃; for 1h;	99%
silica gel at 100℃; for 4h;	60%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 1460-57-7
trans-1,2-cyclohexandiol

: (4aRS,8aSR)-6-(4-methylpent-3-en-1-yl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-4a,8a-diol

Conditions

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; 1,3-bis-(diphenylphosphino)propane In toluene at 130℃; for 48h; Inert atmosphere;	99%
With dodecacarbonyl-triangulo-triruthenium; 2,2'-bis(diphenylphosphino)biphenyl In toluene at 130℃; for 48h; Inert atmosphere; diastereoselective reaction;	84%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 1214-47-7
1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one

: (2-hydroxyphenyl)((1R,2R)-5-(4-methylpent-3-en-1-yl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-yl)methanone

Conditions

Conditions	Yield
Stage #1: 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one With borane-THF; (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; acetic acid In tetrahydrofuran at 20℃; for 1h; Diels-Alder Cycloaddition; Molecular sieve; Inert atmosphere; Stage #2: 7-methyl-3-methene-1,6-octadiene In tetrahydrofuran at 20℃; for 12h; Diels-Alder Cycloaddition; Molecular sieve; Inert atmosphere; enantioselective reaction;	99%
Stage #1: 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one With triphenylborane; (S)-2,15-dichlorotetraphenylene-1,16-diol In 1,2-dichloro-ethane at 100℃; for 2h; Diels-Alder Cycloaddition; Inert atmosphere; Schlenk technique; Sealed tube; Molecular sieve; Stage #2: 7-methyl-3-methene-1,6-octadiene In 1,2-dichloro-ethane at 30℃; Diels-Alder Cycloaddition; Inert atmosphere; Schlenk technique; Sealed tube; Molecular sieve; stereoselective reaction;	89%

Yield

Stage #1: 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one With borane-THF; (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; acetic acid In tetrahydrofuran at 20℃; for 1h; Diels-Alder Cycloaddition; Molecular sieve; Inert atmosphere;
Stage #2: 7-methyl-3-methene-1,6-octadiene In tetrahydrofuran at 20℃; for 12h; Diels-Alder Cycloaddition; Molecular sieve; Inert atmosphere; enantioselective reaction;

99%

Stage #1: 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one With triphenylborane; (S)-2,15-dichlorotetraphenylene-1,16-diol In 1,2-dichloro-ethane at 100℃; for 2h; Diels-Alder Cycloaddition; Inert atmosphere; Schlenk technique; Sealed tube; Molecular sieve;
Stage #2: 7-methyl-3-methene-1,6-octadiene In 1,2-dichloro-ethane at 30℃; Diels-Alder Cycloaddition; Inert atmosphere; Schlenk technique; Sealed tube; Molecular sieve; stereoselective reaction;

89%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 66560-19-8
ethyl 2-((2-oxo-2-phenylethyl)thio)acetate

: C14H22O2S

Conditions

Conditions	Yield
In dichloromethane at -10℃; for 0.5h; Inert atmosphere; UV-irradiation; Flow reactor; regioselective reaction;	99%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 2051-30-1
2,6-dimethyloctane

Conditions

Conditions	Yield
With nickel(II) bis(octanoate); hydrogen; 1,4-bis(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabuta-1,3-diene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 50℃; under 3040.2 Torr; for 24h; Reagent/catalyst;	98%
With cobalt In tetrahydrofuran Heating; High pressure;	79%
With 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthenecobalt(II) dibromide; hydrogen; lithium triethylborohydride In tetrahydrofuran at 20℃; under 7500.75 Torr; for 24h;	76%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 5535-48-8
PVS

: 73301-16-3
[4-(4-Methyl-pent-3-enyl)-cyclohex-3-enesulfonyl]-benzene

Conditions

Conditions	Yield
In benzene at 155℃; for 22h;	98%
With hydroquinone In benzene at 155℃; for 22h;	88.6%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 29414-55-9
6,7-epoxymyrcene

Conditions

Conditions	Yield
With dihydrogen peroxide; tungsten(VI) oxide; [CH3(n-C8H17)3N]+H2PO4- In toluene at 21℃; for 3h;	98%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 22℃; for 0.0833333h;	97%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 0.0833333h; cooling;	95.2%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 2083-32-1
3-(4-methylpent-3-en-1-yl)-2,5-dihydrothiophene-1,1-dioxide

Conditions

Conditions	Yield
Stage #1: 7-methyl-3-methene-1,6-octadiene With 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate In acetonitrile at 20℃; Inert atmosphere; Sealed tube; Stage #2: With boron trifluoride diethyl etherate In acetonitrile at 0 - 70℃; for 12h; Inert atmosphere; Sealed tube;	97%
With sodium metabisulfite; 1,1,1,3',3',3'-hexafluoro-propanol In water at 100℃; under 517.162 - 1034.32 Torr; for 14h; Reagent/catalyst; Sealed tube;	86%
With diethyl ether; sulfur dioxide at 100℃;

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 1439598-96-5
1-benzyl-3-hydroxy-5-methoxyindolin-2-one

: 1439599-39-9
(E)-1-benzyl-3-(3,7-dimethylocta-2,6-dien-1-yl)-3-hydroxy-5-methoxyindolin-2-one

Conditions

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; tricyclohexylphosphine In toluene at 110℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;	97%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 4180-23-8
E-1-(4'-methoxyphenyl)prop-1-ene

: (±)-(1S,2S)-4'-methoxy-2-methyl-4-(4-methylpent-3-en-1-yl)-1,2,3,6-tetrahydro-1,1'-biphenyl

Conditions

Conditions	Yield
With iron perchlorate hexahydrate In acetonitrile at 20℃; for 24h; Diels-Alder Cycloaddition; regioselective reaction;	97%
With C26H18N10Ru(2+)*2C32H12BF24(1-) In dichloromethane for 1.5h; Diels-Alder Cycloaddition; Irradiation;	88%
With 9-(2-trifluoromethylphenyl)-1,3,6,8-tetramethoxythioxanthylium trifluoromethanesulfonate In nitromethane at 20℃; for 1h; Diels-Alder Cycloaddition; UV-irradiation;	84%
With iron(III) chloride In dichloromethane; acetonitrile at 0℃; for 3h;	76%

: 67-56-1
methanol

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 76280-53-0
6-Bromo-7-methoxy-7-methyl-3-methylene-oct-1-ene

Conditions

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid In 1,4-dioxane Ambient temperature;	96%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 105-13-5
4-Methoxybenzyl alcohol

: 1072266-04-6
1-(4-methoxyphenyl)-2,7-dimethyl-3-methyleneoct-6-en-1-one

Conditions

Conditions	Yield
With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II); trifluoroacetic acid In toluene at -78 - 110℃; Inert atmosphere; regioselective reaction;	96%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 201230-82-2
carbon monoxide

: 100-51-6
benzyl alcohol

: C18H24O2

Conditions

Conditions	Yield
With dichloro(1,5-cyclooctadiene)palladium(II); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; under 30003 - 67506.8 Torr; for 20h; Inert atmosphere; Autoclave;	96%

...Expand

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 49633-28-5
1,2-bis-(p-methylphenylsulfonamido)-benzene

: 2-(6-methylhepta-1,5-dien-2-yl)-1,4-Ditosyl-1,2,3,4-tetrahydroquinoxaline

Conditions

Conditions	Yield
With oxygen; palladium diacetate In acetonitrile at 70℃; under 760.051 Torr; for 48h; Sealed tube; Molecular sieve; chemoselective reaction;	96%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 694-53-1
phenylsilane

: C16H24Si

Conditions

Conditions	Yield
With [(2,6-iPr2PhBDI)Mn(μ-H)]2 In benzene-d6 at 130℃; for 48h; Inert atmosphere;	96%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 58940-08-2
(1Z,5Z)-1,6-bis(4-methylpent-3-en-1-yl)cycloocta-1,5-diene

Conditions

Conditions	Yield
With [(MePI)FeCl(μ-Cl)]2; (butadiene)magnesium(THF)2 In neat (no solvent) at 23℃; for 3h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;	96%

: 186581-53-3, 908094-01-9
diazomethane

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 2-cyclopropyl-6-methyl-1,5-heptadiene

Conditions

Conditions	Yield
Stage #1: 7-methyl-3-methene-1,6-octadiene With benzophenone In diethyl ether at 20℃; Stage #2: diazomethane In diethyl ether at 20 - 35℃; for 1.5h;	95.19%

: 15321-51-4
diiron nonacarbonyl

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 33434-20-7
(η4-myrcene)tricarbonyliron

Conditions

Conditions	Yield
In benzene Sonication; addn. of 1.1 equivalents of Fe2(CO)9 to a soln. of the diene in benzene, sonication for 1h or until all solid Fe2(CO)9 had disappeared, concn. of the soln.;; chromatography (SiO2, eluation with petroleum ether/ether);	95%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 74-85-1
ethene

: 1215227-17-0
(Z)-2-methyl-6-(3-propenyl)-octa-2,6-diene

Conditions

Conditions	Yield
With CoCl2(1,4-bis(diphenylphosphino)butane); trimethylaluminum In dichloromethane; toluene at 0℃; under 760.051 Torr; for 6h; Reagent/catalyst; regioselective reaction;	95%
With C30H40FeN2 In pentane at 23℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	92%
With CoCl2(1,4-bis(diphenylphosphino)butane); trimethylaluminum In dichloromethane; toluene at 0℃; under 760.051 Torr; for 0.0833333h; Inert atmosphere;	97.1 mg

: 620-02-0
5-Methylfurfural

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: C16H22O2

Conditions

Conditions	Yield
With carbonyldihydridotris(triphenylphosphine)ruthenium(II); trifluoroacetic acid In toluene at 110℃; for 18h; Schlenk technique;	95%

: 300-57-2
allylbenzene

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: C19H26

Conditions

Conditions	Yield
With C37H47FeN5 at 23℃; for 48h; Diels-Alder Cycloaddition; stereoselective reaction;	95%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 65786-14-3, 16635-18-0
4-bromo-2'-hydroxylchalcone

: C25H27BrO2

Conditions

Conditions	Yield
Stage #1: 4-bromo-2'-hydroxylchalcone With (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; α,α,α-trifluorotoluene; triphenylborane at 100℃; for 1h; Stage #2: 7-methyl-3-methene-1,6-octadiene for 9h; Reflux; enantioselective reaction;	95%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 130-15-4
[1,4]naphthoquinone

: 2-(4-methyl-3-pentenyl)-anthraquinone

Conditions

Conditions	Yield
In toluene at 50℃; for 144h;	94%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 1366042-95-6
1-benzyl-3-hydroxy-5-methylindolin-2-one

: 1439599-37-7
(E)-1-benzyl-3-(3,7-dimethylocta-2,6-dien-1-yl)-3-hydroxy-5-methylindolin-2-one

Conditions

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; tricyclohexylphosphine In toluene at 110℃; for 48h; Inert atmosphere; Sealed tube; regioselective reaction;	94%

: 13803-39-9
5-phenylfuran-2-carbaldehyde

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: C21H24O2

Conditions

Conditions	Yield
With carbonyldihydridotris(triphenylphosphine)ruthenium(II); trifluoroacetic acid In toluene at 110℃; for 18h; Schlenk technique;	94%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 775-12-2
diphenylsilane

: (7-methyl-3-methyleneoct-6-en-1-yl)diphenylsilane

Conditions

Conditions	Yield
With C28H32N2; sodium triethylborohydride; iron(II) chloride In tetrahydrofuran at 20 - 40℃; for 2h; Inert atmosphere; Sealed tube; regioselective reaction;	94%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 3-(4'-methyl-3'-pentenyl)-2,5-dihydrothiophene 1-oxide

Conditions

Conditions	Yield
With naphthalene-1,8-trisulfide-2-oxide In chlorobenzene for 6h; Heating;	93%
With bicyclo[3.3.1]nonylidenebicyclo[3.3.1]nonanethiirane 1-oxide In toluene Cycloaddition; Heating;	68%
With dimethyl acetylenedicarboxylate In dichloromethane at 20℃; for 0.5h;	27%

: 123-35-3
7-methyl-3-methene-1,6-octadiene

: 135-19-3
β-naphthol

: 1039111-86-8
3',3'-dimethyl-1,2-dihydrospiro[benzo[f]chromene-3,1'-cyclohexane]

Conditions

Conditions	Yield
With [2,2]bipyridinyl; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 50℃; for 18h;	93%

Myrcene Chemical Properties

Molecule structure of Myrcene (CAS NO.123-35-3):

IUPAC Name: 7-Methyl-3-methylideneocta-1,6-diene
Molecular Weight: 136.23404 g/mol
Molecular Formula: C₁₀H₁₆
Density: 0.769 g/cm³
Melting Point: -1.00E+01 deg C
Boiling Point: 167 °C at 760 mmHg
Flash Point: 44.4 °C
Index of Refraction: 1.45
Molar Refractivity: 47.57 cm³
Molar Volume: 177 cm³
Polarizability: 18.85×10^-24 cm³
Surface Tension: 22.9 dyne/cm
Enthalpy of Vaporization: 38.69 kJ/mol
Vapour Pressure: 2.29 mmHg at 25 °C
Storage Temp.: 2-8 °C
Water Solubility: practically insoluble
XLogP3-AA: 4.3
Rotatable Bond Count: 4
Exact Mass: 136.125201
MonoIsotopic Mass: 136.125201
Heavy Atom Count: 10
Complexity: 145
Canonical SMILES: CC(=CCCC(=C)C=C)C
InChI: InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3
InChIKey: UAHWPYUMFXYFJY-UHFFFAOYSA-N
EINECS: 204-622-5
Product Categories: Aroma Chemicals

Myrcene Uses

Myrcene is used for synthetic perfume.

Myrcene Production

It is obtained from the essential oil of the plants bay, verbena, myrcia (from which is gets its name) and others. It can also be synthesized by the pyrolysis of pinene.

Myrcene Toxicity Data With Reference

1.	skn-rbt 500 mg/24H MOD	FCTXAV Food and Cosmetics Toxicology. 14 (1976),615.
2.	orl-rat LD50:>5 g/kg	FCTXAV Food and Cosmetics Toxicology. 14 (1976),615.
3.	skn-rbt LD50:>5 g/kg	FCTXAV Food and Cosmetics Toxicology. 14 (1976),615.

Myrcene Consensus Reports

Reported in EPA TSCA Inventory.

Myrcene Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 10-36/37/38
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 16-26-36-37/39
S16:Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: UN 2319 3/PG 3
WGK Germany: 2
RTECS: RG5365000
F: 10-23
HazardClass: 3.2
PackingGroup: III
Hazardous Substances Data: 123-35-3(Hazardous Substances Data)
Low toxicity by ingestion and skin contact. Experimental reproductive effects. A moderate skin and eye irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Myrcene Specification

Myrcene (CAS NO.123-35-3) is also named as 1,6-Octadiene, 7-methyl-3-methylene- ; 2-Methyl-6-methylene-2,7-octadiene ; 3-Methylene-7-methyl-1,6-octadiene ; 4-01-00-01108 (Beilstein Handbook Reference) ; 7-Methyl-3-methylene-1,6-octadiene ; AI3-00738 ; BRN 1719990 ; CCRIS 3725 ; FEMA No. 2762 ; HSDB 1258 ; Myrcene (natural) ; NSC 406264 . Myrcene (CAS NO.123-35-3) is colourless viscous liquid. It is unstable and may be inhibited by the addition of ca. 400 ppm tenox GT-1 or 1000 ppm BHT. Myrcene is flammable and incompatible with strong oxidizing agents, radical initiators. It is insoluble in water. The unsaturated aliphatic hydrocarbons, such as Myrcene, are generally much more reactive than the alkanes. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, compounds in this class can undergo very exothermic addition polymerization reactions. Many of these compounds undergo autoxidation upon exposure to the air to form explosive peroxides. Violent explosions have occurred at low temperatures in ammonia synthesis gas units. These explosions have been traced to the addition products of dienes and oxides of nitrogen, produced from the interaction of nitrogen oxide and oxygen. It may be harmful by inhalation, ingestion or skin absorption. The vapor of Myrcene may travel considerable distance to a source of ignition and flashback.

Product Name

Myrcene

Synthetic route

Myrcene Chemical Properties

Myrcene Uses

Myrcene Production

Myrcene Toxicity Data With Reference

Myrcene Consensus Reports

Myrcene Safety Profile

Myrcene Specification

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