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13466-78-9

Basic Information
CAS No.: 13466-78-9
Name: Bicyclo[4.1.0]hept-3-ene,3,7,7-trimethyl-
Molecular Structure:
Molecular Structure of 13466-78-9 (Bicyclo[4.1.0]hept-3-ene,3,7,7-trimethyl-)
Formula: C10H16
Molecular Weight: 136.26
Synonyms: 3-Carene(8CI); (?à)-3-Carene; (?à)-D3-Carene; D3-Carene
EINECS:
Density: 0.857 g/mL at 25oC(lit.)
Melting Point: 25°C
Boiling Point: 168-169oC705 mm Hg(lit.)
Flash Point: 115 °F
Solubility:
Appearance:
Hazard Symbols: Xi
Risk Codes: R10;R38;R43;R52/53;
Safety: Mildly toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and fumes.
Transport Information:
PSA: 0.00000
LogP: 2.99870
Synthetic route
3479-89-8

3,7,7-trimethyl-cyclohepta-1,3,5-triene

A

2158-55-6

1,1,4-trimethylcycloheptane

B

554-61-0

2-carene

C

7348-54-1

1,5,5-trimethylcycloheptene

D

4755-36-6

1,4,4-trimethylcycloheptene

E

554-59-6

carane

F

13466-78-9

3-carene

Conditions
ConditionsYield
With hydrogen; platinum In hexane at 20 - 22℃; Product distribution; various amounts of hydrogen;A 59%
B 0.7%
C 27.1%
D 9.4%
E 1.8%
F 1.4%
554-61-0

2-carene

A

99-86-5

1-methyl-4-isopropyl-1,3-cyclohexadiene

B

99-87-6

4-methylisopropylbenzene

C

586-63-0

isoterpinolene

D

13466-78-9

3-carene

Conditions
ConditionsYield
thionin-supported zeolite Na-Y In hexane at 20℃; for 0.5h; Product distribution;A 25%
B 18%
C 40%
D 10%
3479-89-8

3,7,7-trimethyl-cyclohepta-1,3,5-triene

A

2158-55-6

1,1,4-trimethylcycloheptane

B

7348-54-1

1,5,5-trimethylcycloheptene

C

4755-36-6

1,4,4-trimethylcycloheptene

D

13466-78-9

3-carene

Conditions
ConditionsYield
With hydrogen; platinum In hexane at 20 - 22℃; Yield given. Further byproducts given;
With hydrogen; platinum In hexane at 20 - 22℃; Yield given. Further byproducts given. Title compound not separated from byproducts;
15103-32-9

4-hydroxymethyl-2-carene

A

554-61-0

2-carene

B

100102-73-6

3,4,7,7-tetramethyl-1,3,5-cycloheptatriene

C

103200-82-4, 106007-94-7

4-methyl-3(10),4-caradiene

D

13466-78-9

3-carene

Conditions
ConditionsYield
With potassium hydroxide at 250℃; Product distribution;A 2.6 % Chromat.
B 28.6 % Chromat.
C 11.9 % Chromat.
D 3.5 % Chromat.
With potassium hydroxide at 250℃;A 2.6 % Chromat.
B 28.6 % Chromat.
C 11.9 % Chromat.
D 3.5 % Chromat.

A

2517-19-3

3-caren-10-ol

B

3479-89-8

3,7,7-trimethyl-cyclohepta-1,3,5-triene

C

86361-47-9, 104048-19-3

cara-3(10),4-diene

D

13466-78-9

3-carene

Conditions
ConditionsYield
rhenium(VII) oxide on aluminum oxide at 150℃; for 1h; Product distribution; in sealed tube, other catalysts and reaction time tested;A 6.2 % Chromat.
B 8.8 % Chromat.
C 6.0 % Chromat.
D 6.2 % Chromat.
13466-78-9

3-carene

2225-98-1

3,4-epoxycarane

Conditions
ConditionsYield
With disodium hydrogenphosphate; 1,1,1,3',3',3'-hexafluoro-propanol; dihydrogen peroxide at 20℃; for 21h;98%
With 1-methyl-1H-imidazole; 3-Methylpyrazole; dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane at 10℃; for 4h;94%
With sodium dihydrogenphosphate; phosphoric acid; dihydrogen peroxide; methyl tri-n-octyl ammonium hydrogen sulfate; sodium tungstate; sodium sulfate In toluene at 70℃; for 4h;88%
62925-73-9

C6H4N2O4S3

13466-78-9

3-carene

131843-17-9

C16H20N2O4S3

Conditions
ConditionsYield
In diethyl ether for 5h; Ambient temperature;92%
13466-78-9

3-carene

554-59-6

carane

Conditions
ConditionsYield
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 12h; Reagent/catalyst;90%
With hydrogen; platinum In ethanol
53724-68-8

1-phenyl-5-tetrazolyl sulfenyl chlorides

13466-78-9

3-carene

3-chloro-4-(1-phenyltetrazolylthio)carane

Conditions
ConditionsYield
In 1,2-dichloro-ethane at -20 - 20℃; for 3h;88.2%
81290-20-2

(trifluoromethyl)trimethylsilane

13466-78-9

3-carene

8,8-difluoro-1,4,4-trimethyltricyclo[5.1.0.03,5]octane

Conditions
ConditionsYield
With sodium iodide In tetrahydrofuran at 120℃; under 6000.6 Torr; for 0.166667h; Inert atmosphere; Flow reactor;88%
13466-78-9

3-carene

(1R,3S)-1-[3-(2-hydroxyethyl)-2,2-dimethylcyclopropyl]2-propanone

Conditions
ConditionsYield
Stage #1: 3-carene With oxygen; ozone; acetic acid In dichloromethane at -4 - -2℃;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 3h;
85%
13466-78-9

3-carene

(3S,4S)-3,4-Dichloro-3,7,7-trimethyl-bicyclo[4.1.0]heptane

Conditions
ConditionsYield
With chloro-trimethyl-silane; tetradecyltrimethylammonium permanganate In dichloromethane at 0 - 3℃; for 1.5h;84%
13466-78-9

3-carene

Δ3-carene bromohydrin

Conditions
ConditionsYield
With N-Bromosuccinimide In water; acetone at 10℃;84%
Conditions
ConditionsYield
With diphenylphosphinic anhydride; dihydrogen peroxide; potassium carbonate In tetrahydrofuran at -5℃; for 20h;80%
With sodium hydroxide; dihydrogen peroxide; N-tosylimidazole In methanol for 3h;56%
13466-78-9

3-carene

108-95-2

phenol

10-isopropyl-1-methyl-2-oxatricyclo[7.3.1.0.3,8]trideca-3(8),4,6-triene

Conditions
ConditionsYield
With aluminium(III) phenoxide at 150 - 160℃;80%
67-56-1

methanol

13466-78-9

3-carene

A

3-methoxy-4,7,7-trimethyl-bicyclo[4.1.0]heptane

B

3-methoxy-3,7,7-trimethyl-bicyclo[4.1.0]heptane

Conditions
ConditionsYield
Stage #1: methanol; 3-carene With mercury(II) diacetate at 0℃;
Stage #2: With sodium In methanol at 0℃;
A n/a
B 80%
13466-78-9

3-carene

13124-69-1

4,7,7-trimethylbicyclo[4.1.0]heptan-3-one

Conditions
ConditionsYield
Stage #1: 3-carene With Acetoxyboran In tetrahydrofuran at 20℃; for 16h;
Stage #2: With pyridinium chlorochromate In dichloromethane for 1h; Heating;
79%
Conditions
ConditionsYield
With hydrogen; Cu + 6percent LiOH on aluminum γ-oxide at 260℃; under 11400 Torr; Further byproducts given. Yields of byproduct given;A 78%
B n/a
C n/a
D n/a
13466-78-9

3-carene

74-95-3

1,2-dibromomethane

35266-89-8

1,4,4-trimethyltricyclo<5.1.0.03,5>octane

Conditions
ConditionsYield
With acetyl chloride; copper(l) chloride; zinc In diethyl ether Heating;76%
13466-78-9

3-carene

cis-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol

Conditions
ConditionsYield
With potassium hydroxide; tetradecyltrimethylammonium permanganate In dichloromethane; tert-butyl alcohol at 30℃; for 1h;71%
13466-78-9

3-carene

A

4-hydroxy-3-hydroperoxycarene

B

57526-47-3

carane-3,4-diol

Conditions
ConditionsYield
With dihydrogen peroxide; magnesium sulfate; tert-butyl alcohol; tungsten boride In water at 25 - 40℃; for 25.5h;A 70.4%
B 21.7%
13466-78-9

3-carene

32543-81-0

1-((1R,3S,5S)-6,6-dimethylbicyclo[3.1.0]hexan-3-yl)ethan-1-one

Conditions
ConditionsYield
With thallium(III) nitrate In methanol Ambient temperature;70%
With thallium(III) nitrate In methanol Ambient temperature;70%
13466-78-9

3-carene

57526-47-3

carane-3,4-diol

Conditions
ConditionsYield
With dihydrogen peroxide; tert-butyl alcohol; tungsten In water at 25℃; for 25.5h;70%
With formic acid; dihydrogen peroxide hydroxylation;
With osmium(VIII) oxide In dichloromethane
Multi-step reaction with 2 steps
1: MCPA / H2O
2: H2SO4; water
View Scheme
13466-78-9

3-carene

A

2225-98-1

3,4-epoxycarane

B

2,2-dimethyl cyclohepta-3,5-diene-1-one

Conditions
ConditionsYield
With cobalt dichloride; oxygen; 2-ethoxycarbonyl-1-cyclopentanone In acetonitrile for 40h;A n/a
B 68%
With cobalt dichloride; oxygen; isobutyraldehyde In acetonitrileA 47%
B 35%
13292-87-0

dimethyl sulfide borane

13466-78-9

3-carene

B-methoxydiisocaranylborane

Conditions
ConditionsYield
In tetrahydrofuran (N2), BH3*SMe2 in THF cooled to 0°C in ice bath, carene added dropwise with stirring, maintained at 0°C for 20 h with stirring; crystals washed with ice-cold Et2O, solid taken up in THF, MeOH added dropwise at 0°C, mixture stirred at 0°C for 2 h, slowly warmed to room temp., stirred at 25°C for 1 h, solvent removed under vac.;68%
13466-78-9

3-carene

67670-71-7, 67670-72-8, 6617-34-1

(+/-)-Car-3-ene-2,5-dione

Conditions
ConditionsYield
With tert.-butylhydroperoxide; oxygen In acetonitrile at 70℃; for 2h; Green chemistry;61.2%
With tert.-butylhydroperoxide; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; water at 20℃; for 24h; Sealed tube; regioselective reaction;60%
With tert.-butylhydroperoxide; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -30 - 20℃; for 6h;35%
13466-78-9

3-carene

99265-61-9

2-(2,2-dimethyl-3-(2-oxopropyl)cyclopropyl)acetic acid

Conditions
ConditionsYield
With sodium periodate; ruthenium(III) trichloride hydrate In water; tert-butyl alcohol at 35 - 55℃; for 3.5h;59%
With sodium periodate; rhodium(III) chloride hydrate In water; tert-butyl alcohol at 35 - 55℃; for 3.5h; Inert atmosphere;59%
With sodium periodate; rhodium(III) chloride hydrate In water; tert-butyl alcohol at 45 - 55℃; for 3.5h; Temperature;

palladium dichloride

13466-78-9

3-carene

89606-45-1

Pd2Cl2(C10H15)2

Conditions
ConditionsYield
With potassium acetate In acetic acid equimolar amts., 55-60°C, 4 h;50%
13466-78-9

3-carene

2,2-dimethyl cyclohepta-3,5-diene-1-one

Conditions
ConditionsYield
With oxygen; isobutyraldehyde; (MeO2CCH(Bn)N=CH(C6H4O)-o)2Co In acetonitrile at 25℃;48%
13466-78-9

3-carene

A

1856-74-2

3-acetyl-6,6-dimethylbicyclo<3.1.0>hexane

94450-61-0

2α-Bromo-3β-hydroxy-3,7,7-trimethylbicyclo<4.1.0>heptane

Conditions
ConditionsYield
With N-Bromosuccinimide; N,N-dimethyl-formamide at 70℃; for 10h;A 25%
B 40%
13466-78-9

3-carene

C10H16O2

Conditions
ConditionsYield
With potassium permanganate; water In acetone at 5℃; for 12h; Temperature;40%
13466-78-9

3-carene

2158-55-6

1,1,4-trimethylcycloheptane

Conditions
ConditionsYield
With hydrogen; platinum on activated charcoal at 70℃; Product distribution; other temperature; other catalyst;37%
64-19-7

acetic acid

13466-78-9

3-carene

13837-89-3

C12H18O2

Conditions
ConditionsYield
With 2-[(phenylmethyl) thio]-5-methyl-1,3,4-thiadiazole; palladium diacetate; triethylamine; p-benzoquinone at 40℃; Inert atmosphere; Green chemistry; regioselective reaction;32%
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    3-Carene CAS NO.13466-78-9

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    3-CARENEC10H16 CAS NO.13466-78-9

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    Bicyclo[4.1.0]hept-3-ene,3,7,7-trimethyl-

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  • 3-CARENE CAS NO.: 13466-78-9

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    3-CARENE CAS NO.: 13466-78-9

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  • 13466-78-9

  • Casno:

    13466-78-9

    13466-78-9

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Chemistry

MF: C10H16
MW: 136.23
EINECS: 236-719-3
bp:  168-169 °C705 mm Hg(lit.)
density:  0.857 g/mL at 25 °C(lit.)
FEMA:  3821
refractive index : n20/D 1.474(lit.)
Fp:  115 °F
storage temp.:  Flammables area
Merck:  1836
The structure of  3-CARENE is:

           

Toxicity Data With Reference

1.   

skn-rbt 500 mg/24H

   FCTXAV    Food and Cosmetics Toxicology. 11 (1973),1053.
2.   

orl-rat LD50:4800 mg/kg

   FCTXAV    Food and Cosmetics Toxicology. 11 (1973),1053.

Consensus Reports

3-CARENE is reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes:  Xi,N 
RIDADR:  UN 2319 3/PG 3
WGK Germany:  2
RTECS:  FH8400000
HazardClass:  3.2
PackingGroup:  III
Mildly toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and fumes.

Standards and Recommendations

ACGIH TLV: TWA 20 ppm (sensitizer); Not Classifiable as a Human Carcinogen

Specification

1、Fire Fighting Measures  of  3-CARENE
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Flammable liquid and vapor. 
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
2、Handling and Storage of  3-CARENE
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. 
Storage: Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container. Flammables-area.