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564-94-3

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Basic Information
CAS No.: 564-94-3
Name: (-)-MYRTENAL
Article Data: 97
Molecular Structure:
Molecular Structure of 564-94-3 ((-)-MYRTENAL)
Formula: C10H14 O
Molecular Weight: 150.221
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
Density: 1.061g/cm3
Melting Point: 53-54 °C
Boiling Point: 215.7°Cat760mmHg
Flash Point: 78.9°C
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.
PSA: 17.07000
LogP: 2.17770
Related products
Synthetic route
515-00-4

myrtenol

564-94-3

6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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Chemistry

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

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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.

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 .