Myrtenal supplier | CasNO.564-94-3

Name
(-)-MYRTENAL
EINECS
CAS No. 564-94-3
Article Data97
CAS DataBase
Density 1.061g/cm³
Solubility
Melting Point 53-54 °C
Formula C10H14 O
Boiling Point 215.7°Cat760mmHg
Molecular Weight 150.221
Flash Point 78.9°C
Transport Information
Appearance
Safety Poison by intravenous route. Moderately toxic by ingestion. Slightly toxic by skin contact. When heated to decomposition it emits acrid smoke and irritating vapors.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Norpinene-2-carboxaldehyde,6,6-dimethyl- (6CI,7CI,8CI); (?à)-Myrtenal; 6,6-Dimethyl-2-norpinene-2-carboxaldehyde;6,6-Dimethylbicyclo[3.1.1]-hept-2-ene-2-carboxaldehyde; Myrtenal; NSC 54384
PSA 17.07000
LogP 2.17770

Synthetic route

: 515-00-4
myrtenol

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With bromobenzene; sodium hydride; triphenylphosphine; palladium diacetate In tetrahydrofuran at 65℃; for 1h;	100%
With bromobenzene; sodium hydride; palladium diacetate; triphenylphosphine In tetrahydrofuran at 65℃; for 1h;	95%
With calcium hydride; oxygen; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper dichloride In acetonitrile at 25℃; for 3h;	93%

: 2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-[1,3]dioxolane

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With carbon tetrabromide In water; acetonitrile at 45℃; for 2h; sonication;	99%

: 80-56-8, 177698-18-9
Pinene

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With pentafluorobenzeneseleninic acid In benzene for 2h; Heating;	85%
With selenium(IV) oxide In 1,4-dioxane; ethanol at 60℃;	70%
With perfluorooctylselenic acid; iodosylbenzene In various solvent(s) Heating;	62%
With selenium(IV) oxide
With selenium(IV) oxide In 1,4-dioxane; ethanol at 65 - 95℃;

: 80-56-8, 177698-18-9
Pinene

A: 515-00-4
myrtenol

B: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With 2-(N-oxido)pyridineseleninic anhydride In dichloromethane at 20℃; for 18h;	A 57% B 28%

: 515-00-4
myrtenol

: 108-95-2
phenol

A: 514-99-8
7,7-dimethyl-2-(hydroxymethyl)bicyclo<3.1.1>heptane

B: 4-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)phenol

C: 3-(2-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methoxy)benzyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene

D: 1344744-38-2
4-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)-9-isopropyl-8,9,10,10a-tetrahydro-6H-benzo[c]chromene

E: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
Stage #1: myrtenol; phenol With aluminum isopropoxide at 160℃; Stage #2: With hydrogenchloride In water	A n/a B 1.5% C 12% D n/a E 6%

...Expand

: 75-09-2
dichloromethane

: 81971-91-7
peroxyde de t-butyle et de myrtenyle

: 3-dichloromethyl-2,10-epoxypinane

B: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With sodium carbonate at 110℃; for 12h;	A 10% B 6%

...Expand

: 177698-19-0
Beta-pinene

A: 24903-95-5
nopinone

B: 16812-40-1
pinocarvone

C: 515-00-4
myrtenol

D: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; titanium(IV) oxide In acetonitrile for 6h; Ambient temperature; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 177698-19-0
Beta-pinene

A: 16812-40-1
pinocarvone

B: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; sodium acetate; sodium chloride; palladium dichloride 1.) AcOH, reflux; 2.) CH3CN, irradiation λ=366 nm; Yield given. Multistep reaction. Yields of byproduct given;

: 177698-19-0
Beta-pinene

A: 58434-29-0
myrtenyl hydroperoxide

: 105815-51-8
7,7-Dimethyl-3-oxatricyclo<4.1.1.02,4>octane-2-methanol

C: 515-00-4
myrtenol

D: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; 5,15,10,20-tetraphenylporphyrin; Ti(O-t-Bu) In chloroform-d1 at 0℃; for 28h; Product distribution; Irradiation; other catalysts;	A 43 % Spectr. B 23 % Spectr. C 16 % Spectr. D 18 % Spectr.
With oxygen; 5,15,10,20-tetraphenylporphyrin; Ti(O-t-Bu) In chloroform-d1 at 0℃; for 28h; Irradiation;	A 43 % Spectr. B 23 % Spectr. C 16 % Spectr. D 18 % Spectr.

...Expand

: 80-56-8, 177698-18-9
Pinene

A: 16812-40-1
pinocarvone

: 33081-46-8
6,6-Dimethylspirobicyclo<3.1.1>heptan-3-ol-2,2'-oxirane

C: 28664-04-2
3-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-one

D: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; 5,15,10,20-tetraphenylporphyrin; titanium(IV) isopropylate In dichloromethane at 0℃; for 20h; Irradiation;	A 5 % Spectr. B 81 % Spectr. C 9 % Spectr. D 3 % Spectr.

...Expand

: 80-56-8, 177698-18-9
Pinene

A: 16812-40-1
pinocarvone

: 33081-46-8
6,6-Dimethylspirobicyclo<3.1.1>heptan-3-ol-2,2'-oxirane

C: 28664-04-2
3-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-one

: 32162-27-9
(1α,2β,4β,6α)-2,2,7-trimethyl-3-oxatricyclo[4.1.1.02,4]octane

E: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; thiamine diphosphate; bis(acetylacetonate)oxovanadium In dichloromethane at 0℃; Product distribution; Irradiation; other catalysts;	A 8 % Spectr. B 46 % Spectr. C 28 % Spectr. D 10 % Spectr. E 8 % Spectr.

...Expand

: 58434-29-0
myrtenyl hydroperoxide

A: 16812-40-1
pinocarvone

B: 547-61-5, 1674-08-4, 2158-49-8, 3917-59-7, 5947-36-4, 6712-79-4, 19889-99-7, 19894-98-5
pinocarveol

C: 515-00-4
myrtenol

D: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
In hexane at 40℃; for 3528h; Product distribution; isomerization reaction;

...Expand

: 22321-84-2, 51131-99-8, 51547-39-8, 75992-91-5, 129263-38-3
trans-pinocarveyl hydroperoxide

A: 16812-40-1
pinocarvone

B: 547-61-5, 1674-08-4, 2158-49-8, 3917-59-7, 5947-36-4, 6712-79-4, 19889-99-7, 19894-98-5
pinocarveol

C: 58434-29-0
myrtenyl hydroperoxide

D: 515-00-4
myrtenol

E: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With copper acetylacetonate Product distribution; Ambient temperature; other metal compounds; other hydroperoxide;

...Expand

: 515-00-4
myrtenol

A: 19250-17-0
myrtenic acid

B: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With chlorine dioxide In tetrachloromethane at 50℃; for 0.75h;	A 4 % Chromat. B 41 % Chromat.

dextrorotatory myrtenol: dextrorotatory myrtenol

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
d-myrtenal;

: 64-19-7
acetic acid

: 515-00-4
myrtenol

chromic acid: chromic acid

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

...Expand

: 80-56-8, 177698-18-9
Pinene

A: 4501-58-0, 23727-15-3, 91200-86-1, 91819-58-8
campholenyc aldehyde

B: 1686-14-2
α-pinene epoxide

C: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With 9,10-Dicyanoanthracene; oxygen In various solvent(s) Product distribution; Further Variations:; Reagents; Solvents; Oxidation; Irradiation;

...Expand

: 80-56-8, 177698-18-9
Pinene

A: 4501-58-0, 23727-15-3, 91200-86-1, 91819-58-8
campholenyc aldehyde

B: 547-61-5, 1674-08-4, 2158-49-8, 3917-59-7, 5947-36-4, 6712-79-4, 19889-99-7, 19894-98-5
pinocarveol

C: 1686-14-2
α-pinene epoxide

D: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With 9,10-Dicyanoanthracene; oxygen In acetonitrile Product distribution; Further Variations:; Solvents; Oxidation; Irradiation;

...Expand

: 177698-19-0
Beta-pinene

A: 16812-40-1
pinocarvone

: 1674-08-4
3-hydroxy-β-pinene

C: 515-00-4
myrtenol

D: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; Co-Fe3O4 at 60℃; under 760.051 Torr; for 7h; Product distribution; Further Variations:; Catalysts;

...Expand

: 177698-19-0
Beta-pinene

A: 547-61-5, 1674-08-4, 2158-49-8, 3917-59-7, 5947-36-4, 6712-79-4, 19889-99-7, 19894-98-5
pinocarveol

B: 515-00-4
myrtenol

C: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; oxygen; rose bengal; acetic anhydride In methanol at 20℃; for 4h; UV-irradiation;

...Expand

: 177698-19-0
Beta-pinene

A: 515-00-4
myrtenol

B: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; rose bengal In N,N-dimethyl-formamide at 20℃; for 4h; UV-irradiation;

: 177698-19-0
Beta-pinene

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; rose bengal; acetic anhydride In methanol at 20℃; for 4h; UV-irradiation;

: 80-56-8, 177698-18-9
Pinene

A: 80-57-9
verbenone

B: 1820-09-3, 1845-30-3, 5416-53-5, 13040-03-4, 18881-04-4, 19890-02-9, 22339-08-8, 80795-83-1, 473-67-6
Verbenol

C: 515-00-4
myrtenol

D: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; rose bengal In N,N-dimethyl-formamide at 20℃; for 4h; UV-irradiation;
With dihydrogen peroxide In acetonitrile at 60℃; for 24h; Temperature;	A 41 %Chromat. B 13 %Chromat. C 17 %Chromat. D 11 %Chromat.

...Expand

: 80-56-8, 177698-18-9
Pinene

A: 80-57-9
verbenone

B: 1820-09-3, 1845-30-3, 5416-53-5, 13040-03-4, 18881-04-4, 19890-02-9, 22339-08-8, 80795-83-1, 473-67-6
Verbenol

C: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; oxygen; rose bengal; acetic anhydride In methanol at 20℃; for 4h; UV-irradiation;

...Expand

: 177698-19-0
Beta-pinene

A: 16812-40-1
pinocarvone

: trans-pinocarveol

C: 515-00-4
myrtenol

D: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen at 60℃; under 760.051 Torr; for 6h; Neat (no solvent);

...Expand

: 80-56-8, 177698-18-9
Pinene

A: 80-57-9
verbenone

B: 1820-09-3, 1845-30-3, 5416-53-5, 13040-03-4, 18881-04-4, 19890-02-9, 22339-08-8, 80795-83-1, 473-67-6
Verbenol

C: 16812-40-1
pinocarvone

: trans-pinocarveol

E: 1686-14-2
α-pinene epoxide

F: 515-00-4
myrtenol

G: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen at 60℃; under 760.051 Torr; for 6h; Neat (no solvent);

...Expand

: 80-56-8, 177698-18-9
Pinene

A: 80-57-9
verbenone

B: 1820-09-3, 1845-30-3, 5416-53-5, 13040-03-4, 18881-04-4, 19890-02-9, 22339-08-8, 80795-83-1, 473-67-6
Verbenol

C: 16812-40-1
pinocarvone

: trans-pinocarveol

E: 515-00-4
myrtenol

F: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen at 60℃; under 3800.26 Torr; for 3.5h; Neat (no solvent); Autoclave;

...Expand

: 80-56-8, 177698-18-9
Pinene

A: 16812-40-1
pinocarvone

B: 547-61-5, 1674-08-4, 2158-49-8, 3917-59-7, 5947-36-4, 6712-79-4, 19889-99-7, 19894-98-5
pinocarveol

C: 22321-84-2
pinocarveyl hydroperoxide

D: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With 6,7-bis[3-(Nε-tert-butyloxycarbonyllysine methyl ester)]-1,3,5,8-tetramethyl-2,4-divinylporphyrin immobilized in silica gel In chloroform at 20℃; for 30h; Quantum yield; Time; Irradiation;

...Expand

: 80-56-8, 177698-18-9
Pinene

A: 16812-40-1
pinocarvone

: trans-pinocarveol

C: 22321-84-2
pinocarveyl hydroperoxide

D: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions

Conditions	Yield
With chlorophyll extract of fresh spinach leaves immobilized in silica gel In chloroform at 20℃; Reagent/catalyst; Irradiation;

...Expand

: 130827-43-9
(1S,2S)-1-phenyl-N2-methyl-1,2-propandiamine

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 130827-39-3, 130857-87-3, 130857-92-0
(1R,2R,3R,4S,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,5-dimethyl-4-phenyl-imidazolidine

Conditions

Conditions	Yield
In chloroform for 24h; Ambient temperature;	100%

: 130857-96-4
1R,2S-N,N-dimethyl-2-phenyl-3-methyl-1,3-diaminoethane

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 130827-41-7, 130857-89-5, 130857-95-3
(1S,2S,3R,4S,5R)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,3,4-trimethyl-5-phenyl-imidazolidine

Conditions

Conditions	Yield
In chloroform for 24h; Ambient temperature;	100%

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 4764-14-1
6,6-dimethylbicyclo<3.3.1>heptane-2-carboxaldehyde

Conditions

Conditions	Yield
With hydrogen; SC-1 Ni2B In methanol at 25℃; under 760 Torr; for 24h;	96%
With hydrido(triphenylphosphine)copper(I) hexamer; phenylsilane In toluene for 5h; Ambient temperature;	80%

: 67-64-1
acetone

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 56933-99-4
4-(6,6-dimethylbicyclo[3,1,1]hept-2-en-2-yl)-2-butanone

Conditions

Conditions	Yield
With Pd-MgO; hydrogen at 75℃; under 3750.38 Torr; for 3h;	95%

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 149-73-5
trimethyl orthoformate

: 1263208-49-6
2,2-dimethoxymethyl-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene

Conditions

Conditions	Yield
With 1-ethyl-3-methylimidazolium hydrogensulfate In methanol at 5 - 20℃; for 2h;	93%

: 504-02-9
1,3-cylohexanedione

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: C16H22O2

Conditions

Conditions	Yield
With ethylenediamine diacetic acid In neat (no solvent) at 20℃; for 0.5h; Knoevenagel Condensation; Green chemistry;	93%

: 676-58-4
methylmagnesium chloride

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 33829-99-1
1-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethanol

Conditions

Conditions	Yield
In tetrahydrofuran for 12h; Ambient temperature;	92%

: 542-92-7
cyclopenta-1,3-diene

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: (1R)-(-)-myrtenal

Conditions

Conditions	Yield
With pyrrolidine In methanol for 5h; Inert atmosphere; Schlenk technique;	90%

: 52509-14-5
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 124931-24-4
(E)-3-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)prop-2-enal

Conditions

Conditions	Yield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Sealed tube; Inert atmosphere; Stage #2: 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde In tetrahydrofuran at 20℃; for 6h; Sealed tube; Inert atmosphere;	90%

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 515-00-4
myrtenol

Conditions

Conditions	Yield
With lithium pyrrolidinoborohydride at 25℃;	89%
With LiPyrrBH3 In tetrahydrofuran at 25℃; for 3h;	89%
With sodium triphenyl boronhydride In tetrahydrofuran at 0℃; for 1h;	100 % Chromat.
With formic acid; iron(II) tetrafluoroborate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine In tetrahydrofuran at 60℃; for 2h; Schlenk technique; Inert atmosphere;	99 %Chromat.

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 22339-11-3
α-pinenyl bromide

Conditions

Conditions	Yield
Stage #1: 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 8h; Stage #2: With carbon tetrabromide; triphenylphosphine In tetrahydrofuran; dichloromethane at 0℃; for 0.5h;	84%

: 1123-49-5
3,5-dimethyl-4-nitroisoxazole

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 5-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)vinyl]-3-methyl-4-nitroisoxazole

Conditions

Conditions	Yield
With piperidine In ethanol at 65℃; for 2h;	81%

: (Z)-2-cyano-3-mercapto-3-(phenylamino)acrylamide

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 884536-72-5
(RR,RS)-5-cyano-2-(6',6'-dimethylbicyclo[3.1.1]hept-2'-en-2'-yl)-6-phenylamino-2,3-dihydro-1,3-thiazin-4(1H)-one

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 2h; Heating;	80%

: 6610-29-3
4-methylthiosemicarbazide

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: C12H19N3S

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 85℃;	80%

: 461-72-3
2,4-imidazolidinedione

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 5-[1-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-meth-(Z)-ylidene]-imidazolidine-2,4-dione

Conditions

Conditions	Yield
With sodium acetate on alumina for 0.0333333h; microwave irradiation;	76%

: 75-05-8
acetonitrile

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 324538-16-1
C12H17NO

Conditions

Conditions	Yield
With [2,6-(iPr2PO)2C6H3]NiCH2CN at 20℃; for 24h; Inert atmosphere;	73%

: 130827-42-8
(1R,2S)-1-phenyl-N2-methyl-1,2-propandiamine

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

A: 130827-39-3, 130857-87-3, 130857-92-0
(1R,2R,3S,4R,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,5-dimethyl-4-phenyl-imidazolidine

B: 130827-39-3, 130857-87-3, 130857-92-0
(1S,2S,3S,4R,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,5-dimethyl-4-phenyl-imidazolidine

Conditions

Conditions	Yield
In chloroform for 24h; Ambient temperature;	A 71% B 12%

...Expand

: 1875-48-5
N-aminophthalamide

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

A: 1445-69-8
2,3-dihydrophthalazine-1,4-dione

B: 121597-24-8
myrtenal phthaloylhydrazone

Conditions

Conditions	Yield
In ethanol for 2.5h; Heating;	A n/a B 67%

...Expand

: 64-18-6
formic acid

: 931-53-3
Cyclohexyl isocyanide

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 2-(cyclohexylamino)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-2-oxoethyl formate

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 48h; Passerini Condensation; Inert atmosphere;	66%

...Expand

: 64-18-6
formic acid

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 2-(tert-butylamino)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-2-oxoethyl formate

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 48h; Passerini Condensation; Inert atmosphere;	64%

...Expand

: N-Boc-(tri-n-butylstannyl)dimethylamine

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 1,1-dimethylethyl N-methyl-N-[(bicyclo[3.3.1](4,4-dimethyl-6-formyl)heptyl)methyl] carbamate

Conditions

Conditions	Yield
Stage #1: N-Boc-(tri-n-butylstannyl)dimethylamine With n-butyllithium In tetrahydrofuran at -78℃; for 0.283333h; Metallation; Stage #2: In tetrahydrofuran at -78 - -53℃; for 0.416667h; Transmetallation; Stage #3: 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde With chloro-trimethyl-silane In tetrahydrofuran at -78 - 20℃; Substitution;	62%

: 130857-97-5
(1S,2S)-1-phenyl-N1,N2-dimethyl-1,2-propandiamine

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

A: 130827-41-7, 130857-89-5, 130857-95-3
(1R,2R,3R,4S,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,3,4-trimethyl-5-phenyl-imidazolidine

B: 130827-41-7, 130857-89-5, 130857-95-3
(1R,2S,3R,4S,5S)-2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-1,3,4-trimethyl-5-phenyl-imidazolidine

Conditions

Conditions	Yield
In chloroform for 24h; Ambient temperature;	A 60% B 40%

...Expand

: 109-80-8
1.3-propanedithiol

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 69460-06-6
2-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-[1,3]dithiane

Conditions

Conditions	Yield
With TAFF In benzene for 3h; Heating;	60%

: 934-06-5
(S)-5-oxopyrrolidine-2-carbohydrazide

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: N'-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylene)-5-oxopyrrolidine-2-carbohydrazide

Conditions

Conditions	Yield
With hydrazine hydrate In water at 20℃; for 1h;	60%

: 64-18-6
formic acid

: 39546-47-9
p-chlorobenzylisocyanide

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: 2-(4-chlorobenzylamino)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-2-oxoethyl formate

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 48h; Passerini Condensation; Inert atmosphere;	57%

...Expand

: 51054-41-2
6,7-dimethoxy-1-cyanomethylene-1,2,3,4-tetrahydroisoquinoline

: 564-94-3
6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

: C22H24N2O2

Conditions

Conditions	Yield
With cerium(III) chloride In acetonitrile at 20℃; for 6h;	52%

Myrtenal Chemical Properties

Molecular Structure of Myrtenal (CAS NO.564-94-3):

EINECS: 209-274-8
IUPAC Name: 7,7-Dimethylbicyclo[3.1.1]hept-3-ene-4-carbaldehyde
Molecular Formula: C₁₀H₁₄O
Molecular Weight: 150.217560 g/mol
XLogP3-AA: 2.1
H-Bond Donor: 0
H-Bond Acceptor: 1
Canonical SMILES: CC1(C2CC=C(C1C2)C=O)C
InChI: InChI=1S/C10H14O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,6,8-9H,4-5H2,1-2H3
InChIKey: KMRMUZKLFIEVAO-UHFFFAOYSA-N
Index of Refraction: 1.561
Molar Refractivity: 45.86 cm³
Molar Volume: 141.4 cm³
Surface Tension: 40.2 dyne/cm
Density: 1.061 g/cm³
Flash Point: 78.9 °C
Enthalpy of Vaporization: 45.21 kJ/mol
Boiling Point: 215.7 °C at 760 mmHg
Vapour Pressure: 0.145 mmHg at 25 °C
Water Solubility: 215.9 mg/L at 25 °C
Refractive Index: n20/D 1.504
Storage Temp.: 2-8 °C

Myrtenal Toxicity Data With Reference

1.	orl-rat LD50:2300 mg/kg	FCTOD7 Food and Chemical Toxicology. 26 (1988),329.
2.	ivn-mus LD50:170 mg/kg	FCTOD7 Food and Chemical Toxicology. 26 (1988),329.
3.	skn-rbt LD50:>5 g/kg	FCTOD7 Food and Chemical Toxicology. 26 (1988),329.

Myrtenal Consensus Reports

Reported in EPA TSCA Inventory.

Myrtenal Safety Profile

Safety Information of Myrtenal (CAS NO.564-94-3):
Safety Statements: 23-24/25
S23:Do not breathe vapour
S24/25:Avoid contact with skin and eyes
WGK Germany: 2
RTECS: DT5180000
F: 10-23
Poison by intravenous route. Moderately toxic by ingestion. Slightly toxic by skin contact. When heated to decomposition it emits acrid smoke and irritating vapors.

Myrtenal Specification

Myrtenal with CAS Registry Number of 564-94-3 is clear colourless to yellow liquid, also known as 2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene ; 2-Norpinene-2-carboxaldehyde, 6,6-dimethyl- ; 6,6-Dimethyl-2-norpinene-2-carboxaldehyde ; 6,6-Dimethylbicyclo(3.1.1)hept-2-ene-2-carboxaldehyde ; Benihinal ; Bicyclo(3.1.1)hept-2-ene-2-carboxaldehyde, 6,6-dimethyl- ; FEMA No. 3395 ; NSC 54384 ; 2-Norpinene-2-carboxaldehyde, 6,6-dimethyl- (8CI) ; Pin-2-ene-1-carbaldehyde . Myrtenal is a kind of spice and can be used for synthesis of more valuable spices such as basil Draba .

Product Name

(-)-MYRTENAL

Synthetic route

Myrtenal Chemical Properties

Myrtenal Toxicity Data With Reference

Myrtenal Consensus Reports

Myrtenal Safety Profile

Myrtenal Specification

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