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Cinene
Cas No: 138-86-3
USD $ 1.0-2.0 / Metric Ton 1 Metric Ton 2 Metric Ton/Day Hangzhou Keyingchem Co.,Ltd Contact Supplier
Cinene
Cas No: 138-86-3
No Data 1 Metric Ton 100 Metric Ton/Year JINHUA HUAYI CHEMICAL CO., LTD. Contact Supplier
Dipentene Manufacturer/High quality/Best price/In stock
Cas No: 138-86-3
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality Dipentene supplier in China
Cas No: 138-86-3
No Data 1 Kilogram 30 Metric Ton/Month Simagchem Corporation Contact Supplier
Cinene CAS NO.138-86-3
Cas No: 138-86-3
USD $ 1.0-3.0 / Kilogram 1 Kilogram 10 Kilogram/Day Hebei yanxi chemical co.,LTD. Contact Supplier
Dipentene
Cas No: 138-86-3
No Data 1 Kilogram 10000 Metric Ton/Year Hefei TNJ chemical industry co.,ltd Contact Supplier
Cinene
Cas No: 138-86-3
No Data 1 Kilogram 20 Metric Ton/Month Henan Allgreen Chemical Co.,Ltd Contact Supplier
High Quality Dipentene
Cas No: 138-86-3
No Data 1 1 Ality Chemical Corporation Contact Supplier
DL-Limonene
Cas No: 138-86-3
No Data 1 Kilogram Unlimited Kilogram/Day Jiangxi LinQ Spices Co.,Ltd. Contact Supplier
DL-Limonene CAS: 138-86-
Cas No: 138-86-3
USD $ 1.0-1.0 / Kilogram 1 Kilogram 1000 Metric Ton/Year Henan Sinotech Import&Export Corporation Contact Supplier

138-86-3 Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 39, p. 1860, 1961 DOI: 10.1139/v61-249Tetrahedron Letters, 20, p. 3519, 1979 DOI: 10.1016/S0040-4039(01)95450-4

Health Hazard

Liquid irritates eyes; prolonged contact with skin causes irritation. Ingestion causes irritation of gastrointestinal tract.

Aroma threshold values

Detection: 4 to 229 ppb

Anticancer Research

Tested as promising antitumor molecules in induced tumor on rat tissues, D-limonenewas tested in preclinical studies in patients with advanced cancer. Limonene inhibitsthe activity of HMG-CoA reductase, subsequently reducing the possibility of cancergrowth. The mechanism of action involves the inhibition of prenyltransferases withthe activation of glutathione-S transferase and uridine diphospho-glucuronosyltransferase.More interest was pointed on the principal metabolite:perillyl alcohol which is more potent than limonene. The interest on perillyl alcoholis based on the necessity of a very high dosage of D-limonene in preclinical studies(about 1000 mg/kg/day in human mammary tumor) that can cause notably importantside effects. The more active perillyl alcohol and the less low active doseshypothesized this molecule as a clinical candidate (Pattanayak et al. 2009; Chenet al. 2013; Fontes et al. 2013; Rani and Sharma 2013).

Reactivity Profile

Cinene may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas.

Production Methods

Limonene occurs in the oil of many plants and is the main constituent (≤86%) of the terpenoid fraction of fruit, flowers, leaves, bark, and pulp from shrubs, annuals, or trees including anise, mint, caraway, polystachya, pine, lime, and orange oil. It occurs as a by-product in the manufacture of terpineol and in various synthetic products made from α-pinene or turpentine oil. It is found in the gas phase of tobacco smoke and has been detected in urban atmospheres.

Contact allergens

Limonene is a racemic form of dand l-limonene. d-Limonene is contained in Citrus species such as citrus, orange, mandarin, and bergamot. l-Limonene is contained in Pinus pinea. The racemic form (dand l-limonene) is also named dipentene.

Description

D-limonene, which is a volatile oil, constitutes approximately 98% of orange peel oil by weight and has moderately good knockdown activity against ectoparasites of companion animals. The insecticidal activity of both d-limonene and linalool is enhanced when synergized by piperonyl butoxide. Apart from toxicoses reported in cats (65), d-limonene generally has a high margin of safety.

Air & Water Reactions

Flammable. Insoluble in water.

Fire Hazard

Behavior in Fire: Containers may explode.

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

A skin irritant. Flammable when exposed to heat or flame; can react vigorously with oxidzing materials. When heated to decomposition it emits acrid smoke and irritating fumes.

Contact allergens

Dipentene corresponds to a racemic mixture of d-limonene and l-limonene. Dipentene can be prepared from wood turpentine or by synthesis. It is used as a solvent for waxes, rosin and gums, in printing inks, perfumes, rubber compounds, paints, enamels, and lacquers. An irritant and sensitizer, dipentene caused contact dermatitis mainly in painters, polishers, and varnishers

Uses

d-Limonene is a flavoring agent that is a liquid, colorless with a pleasant odor resembling mild citrus. It is miscible in alcohol, most fixed oils, and mineral oil; soluble in glycerin; and insoluble in water and propylene glycol. It is obtained from citrus oil. It is also termed d-p-mentha-1,8,diene and cinene.

Occurrence

It has been reported found in more than 300 essential oils in amounts ranging from 90 to 95% (lemon, orange, mandarin) to as low as 1% (palmarosa); the most widespread form is the d-limonene, followed by the racemic form and then l-limo nene. Also reported found in ginger, nutmeg, pepper, mace, hop oil, coriander seed, calamus, dill herb, caraway seed and rosemary.

Chemical Properties

Limonene (4R)-(+)-limonene and (4S)-(?)-limonene as well as the racemate (dipentene) occur abundantly in many essential oils.The(+) isomer is present in citrus peel oils at a concentration of over 90%; a low concentration of the (?) isomer is found in oils from the Mentha species and conifers. Limonene is a liquid with lemon-like odor. It is a reactive compound; oxidation often yields more than one product. Dehydrogenation leads to p-cymene. Limonene can be converted into cyclic terpene alcohols by hydrohalogenation, followed by hydrolysis. Nitrosyl chloride adds selectively to the endocyclic double bond; this reaction is utilized in the manufacture of (?)-carvone from (+)- limonene. (+)-Limonene is obtained in large amounts as a by-product in the production of orange juice; (?)-limonene is isolated in relatively small quantities from essential oils. Racemic limonenes, which are commercially available under the name dipentene, are formed as by-products in many acid-catalyzed isomerizations of α- and β-pinene. Distillation of the so-called dipentene fraction yields limonenes in varying degrees of purity. The limonenes are used as fragrance materials for perfuming household products and as components of artificial essential oils.

Taste threshold values

Taste characteristics at 30 ppm: sweet, orange, citrus and terpy.

Carcinogenicity

Induction of kidney neoplasias has been observed in male rats of strains that have significant concentrations of the protein a2u-globulin (158a). This protein is not expressed in females or species other than the rat; therefore, limonene carcinogenicity appears to be limited to the male of specific strains of this species. Subcutaneous injection of the compound or its hydroperoxide into C57BL/6 mice decreased the incidence of dibenzopyrene- induced tumors appreciably. Given orally either 15 min or 1 h prior to nitrosodiethylamine, D-limonene reduced forestomach tumor formation by about 60% and pulmonary adenoma formation by about 35%. Reduction of cancer incidence and metastasis by limonene has also been reported in other systems (158b).

Definition

ChEBI: A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.

Chemical Properties

d-, l- or dl-Limonene has a pleasant, lemon-like odor free from camphoraceous and turpentine-like notes. Limonene is the most important and widespread terpene; it is known in the d- and l- optically active forms and in the optically inactive dl-form (known as dipentene).

Chemical Properties

colourless or light yellow liquid

General Description

A colorless liquid with an odor of lemon. Flash point 113°F. Density about 7.2 lb /gal and insoluble in water. Hence floats on water. Vapors heavier than air. Used as a solvent for rosin, waxes, rubber; as a dispersing agent for oils, resins, paints, lacquers, varnishes, and in floor waxes and furniture polishes.

Preparation

d-Limonene may be obtained by steam distillation of citrus peels and pulp resulting from the production of juice and cold pressed oils, or from deterpenation of citrus oils; it is sometimes redistilled.

Uses

d-limonene is used for perfuming and to mask odor. It is a chemical constituent of citrus oil.

Uses

Limonene is an antioxidant and flavoring agent that occurs in lemons, oranges, and pineapple juice, being obtained from the oils. It is a colorless liquid which is insoluble in water and propylene glycol, very slightly soluble in glycerin, and miscible with alcohol, most fixed oils, and mineral oil. It prevents or delays enzymatic browning-type oxidation.
InChI:InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1

138-86-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (L0046)  (±)-Limonene  >95.0%(GC) 138-86-3 25mL 160.00CNY Detail
TCI America (L0046)  (±)-Limonene  >95.0%(GC) 138-86-3 500mL 585.00CNY Detail
Alfa Aesar (45805)  Dipentene, tech.    138-86-3 50ml 232.0CNY Detail
Alfa Aesar (45805)  Dipentene, tech.    138-86-3 250ml 433.0CNY Detail

138-86-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name limonene

1.2 Other means of identification

Product number -
Other names dycom

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:138-86-3 SDS

138-86-3Synthetic route

(−)-β-pinene
18172-67-3

(−)-β-pinene

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
7785-26-4

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene

B

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
In liquid sulphur dioxide Ambient temperature;A 97%
B 3%
In liquid sulphur dioxide Rate constant; Mechanism; Kinetics; Ambient temperature;A 97%
B 3%
Limonene oxide
1195-92-2

Limonene oxide

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With lithium; biphenyl In 1,2-dimethoxyethane for 4h; Heating; other solvents, other temperatures, other reaction times, other catalysts;96%
With lithium In tetrahydrofuran for 82h; Heating;86%
With isopropyl alcohol In toluene at 110℃; for 24h; Inert atmosphere; chemoselective reaction;68 %Chromat.
Conditions
ConditionsYield
With H2SiEt2; tris(pentafluorophenyl)borate In dichloromethane86%
With boron trifluoride diethyl etherate; sodium cyanoborohydride In tetrahydrofuran for 3h; Ambient temperature;50%
(2Z,6E)-3,7-dimethyl-8-trimethylsilyl-2,6-octadien-1-ol
79433-08-2

(2Z,6E)-3,7-dimethyl-8-trimethylsilyl-2,6-octadien-1-ol

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With titanium tetrachloride; N-methylaniline In dichloromethane at -23℃; for 1h;77%
(2Z,6E)-3,7-dimethyl-8-tributylstannyl-2,6-octadien-1-ol
79433-10-6

(2Z,6E)-3,7-dimethyl-8-tributylstannyl-2,6-octadien-1-ol

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With titanium tetrachloride; N-methylaniline In dichloromethane at -23℃; for 2h;73%
perillol
536-59-4

perillol

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With methanol; toluene-4-sulfonic acid at 25℃; for 18h; Inert atmosphere; Sealed tube; UV-irradiation;73%
limonene sulphide

limonene sulphide

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With biphenyl; lithium In 1,2-dimethoxyethane for 16h; Heating;71%
Beta-pinene
177698-19-0

Beta-pinene

B

1-methyl-4-isopropenylbenzene
1195-32-0

1-methyl-4-isopropenylbenzene

C

camphene
79-92-5

camphene

D

C20H32

C20H32

E

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With hydrogen at 140℃; for 4h; Temperature; Reagent/catalyst;A n/a
B n/a
C n/a
D 65.6%
E n/a
Geraniol
106-24-1

Geraniol

A

(Z)-ocimene
3338-55-4

(Z)-ocimene

B

trans ocimene
3779-61-1

trans ocimene

C

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With sesquiterpene synthases Cop4 from Coprinus cinereus In terpene synthase buffer at 25℃; for 18h; Enzymatic reaction;A 61%
B 9.1%
C 23.7%
Acetic acid (2Z,6E)-3,7-dimethyl-8-tributylstannanyl-octa-2,6-dienyl ester
79433-11-7

Acetic acid (2Z,6E)-3,7-dimethyl-8-tributylstannanyl-octa-2,6-dienyl ester

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With methylaluminium bis(trifluoroacetate) In hexane at 25℃; for 21h;51%
Conditions
ConditionsYield
Mechanism; Wolff-Kishner-red.;50%
Wolff-Kishner-red.;
(+)-α-pinene
7785-70-8

(+)-α-pinene

A

2,4,4,8-Tetramethyl-3-aza-bicyclo[3.3.1]nona-2,7-diene

2,4,4,8-Tetramethyl-3-aza-bicyclo[3.3.1]nona-2,7-diene

B

4-((1S,5R)-6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl)-benzonitrile

4-((1S,5R)-6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl)-benzonitrile

C

4-((1S,2S,5R)-4,6,6-Trimethyl-bicyclo[3.1.1]hept-3-en-2-yl)-benzonitrile

4-((1S,2S,5R)-4,6,6-Trimethyl-bicyclo[3.1.1]hept-3-en-2-yl)-benzonitrile

D

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With terephthalonitrile In acetonitrile Irradiation; Further byproducts given;A 21%
B n/a
C n/a
D 50%
α-terpinyl chloride
39864-10-3

α-terpinyl chloride

zinc diacetate
557-34-6

zinc diacetate

A

Terpinolene
586-62-9

Terpinolene

B

terpinyl acetate
80-26-2

terpinyl acetate

C

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With pyridine In dichloromethane at 40℃; for 80h; Product distribution; Heating; other solvents and temperatures;A n/a
B 48%
C n/a
With pyridine In dichloromethane at 40℃; for 80h; Heating; Yields of byproduct given;A n/a
B 48%
C n/a
(4-Isopropenyl-cyclohex-1-enylmethyl)-trimethyl-silane
82096-14-8

(4-Isopropenyl-cyclohex-1-enylmethyl)-trimethyl-silane

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With cesium fluoride In dimethyl sulfoxide at 100℃; for 0.5h;46%
Geraniol
106-24-1

Geraniol

A

3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

B

(Z)-ocimene
3338-55-4

(Z)-ocimene

C

trans ocimene
3779-61-1

trans ocimene

D

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With sesquiterpene synthases Cop6 from Coprinus cinereus In terpene synthase buffer at 25℃; for 18h; Enzymatic reaction;A 34.6%
B 9.2%
C 7.11%
D 45%
neryl chloride
20536-36-1

neryl chloride

A

Terpinolene
586-62-9

Terpinolene

B

α-terpinyl chloride
39864-10-3

α-terpinyl chloride

C

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With 1,3-bis[3,5-bis(trifluoromethyl)phenyl]urea; sodium hydrogencarbonate In chloroform-d1 at 25℃; for 24h; Inert atmosphere; Sealed tube;A 17.47%
B 43.15%
C 19.28%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

A

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

3,7-Dimethyl-octa-1,3,6-trien

B

Terpinolene
586-62-9

Terpinolene

C

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With rhenium(VII) oxide In toluene at 100℃; for 24h;A 32%
B 22%
C 43%
With sulfuric acid In toluene at 100℃; for 24h;A 11%
B 25%
C 20%
1,2,8,9-tetrabromo-p-menthane
4764-54-9

1,2,8,9-tetrabromo-p-menthane

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With sodium sulfide; Aliquat 336 In water; benzene for 1h; Ambient temperature;41%
Beta-pinene
177698-19-0

Beta-pinene

B

Terpinolene
586-62-9

Terpinolene

C

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

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

D

crithmene
99-85-4

crithmene

dl-camphene
565-00-4

dl-camphene

F

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
aluminum oxide at 232℃; Thermodynamic data; Mechanism; isomerization;A 27%
B n/a
C n/a
D n/a
E 38%
F n/a
With pyridine; aluminum oxide at 232℃; Thermodynamic data; Mechanism; isomerization, variation of partial pressure of pyridine;A 11%
B n/a
C n/a
D n/a
E 28%
F n/a
acetic acid
64-19-7

acetic acid

A

Terpinolene
586-62-9

Terpinolene

B

camphene
79-92-5

camphene

C

terpinyl acetate
80-26-2

terpinyl acetate

D

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With 1-(3-sulfonic acid)propyl-3-poly(ethylene glycol) octadecylamine polyoxyethylene ether tetrafluoroborate at 30℃; for 10h; Catalytic behavior; Concentration; Reagent/catalyst; Temperature; Time;A 13.99 %Chromat.
B 17.23 %Chromat.
C 35.7%
D 16.55 %Chromat.
terephthalonitrile
623-26-7

terephthalonitrile

methanol
67-56-1

methanol

(-)-α-pinene
7785-26-4

(-)-α-pinene

acetonitrile
75-05-8

acetonitrile

cis-6-(4-cyanophenyl)-4-(1-methoxy-1-methylethyl)-1-methylcyclohexene
122723-00-6, 122744-26-7

cis-6-(4-cyanophenyl)-4-(1-methoxy-1-methylethyl)-1-methylcyclohexene

trans-6-(4-cyanophenyl)-4-(1-methoxy-1-methylethyl)-1-methylcyclohexene
122723-00-6, 122744-26-7

trans-6-(4-cyanophenyl)-4-(1-methoxy-1-methylethyl)-1-methylcyclohexene

C

2,4,4,8-Tetramethyl-3-aza-bicyclo[3.3.1]nona-2,7-diene

2,4,4,8-Tetramethyl-3-aza-bicyclo[3.3.1]nona-2,7-diene

D

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With biphenyl at 10℃; for 72h; Mechanism; Irradiation; other monoterpenes;A 23%
B 28%
C 35%
D n/a
(-)-α-pinene
7785-26-4

(-)-α-pinene

acetonitrile
75-05-8

acetonitrile

A

2,4,4,8-Tetramethyl-3-aza-bicyclo[3.3.1]nona-2,7-diene

2,4,4,8-Tetramethyl-3-aza-bicyclo[3.3.1]nona-2,7-diene

B

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With terephthalonitrile; biphenyl In methanol for 72h; Irradiation;A 35%
B n/a
geranyl diphosphate

geranyl diphosphate

A

Beta-pinene
177698-19-0

Beta-pinene

C

Terpinolene
586-62-9

Terpinolene

D

crithmene
99-85-4

crithmene

E

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With SCO7700 protein; sodium chloride; magnesium chloride; 2,2'-piperazine-1,4-diyl-bis-ethanesulfonic acid In pentane at 30℃; for 18h; pH=7.0; Kinetics; Reagent/catalyst;A 23%
B 6%
C 29%
D 10%
E 32%

A

Terpinolene
586-62-9

Terpinolene

B

terpineol
98-55-5

terpineol

C

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 3.5h;A 32%
B 13%
C 27%
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 3.5h;A 25%
B 10%
C 32%
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 3.5h;A 31%
B 24%
C 21%
With iron(III) chloride adsorbed on silica gel In dichloromethane at 20℃; for 3.5h;A 23%
B 25%
C 30%
(-)-α-pinene
7785-26-4

(-)-α-pinene

A

(Z)-ocimene
3338-55-4

(Z)-ocimene

B

limonene.
138-86-3

limonene.

C

4E,6Z-alloocimene
7216-56-0

4E,6Z-alloocimene

Conditions
ConditionsYield
under 13 - 20 Torr; Inert atmosphere; Pyrolysis; Reflux;A 24.82%
B 30.92%
C 26.06%
3,7-dimethyl-oct-6-enal
106-23-0, 26489-02-1

3,7-dimethyl-oct-6-enal

A

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

7-methyl-3-methene-1,6-octadiene

B

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

3,7-Dimethyl-octa-1,3,6-trien

C

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

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

D

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

3,8-p-Menthadien

E

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
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%

A

Terpinolene
586-62-9

Terpinolene

B

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

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

C

camphene
79-92-5

camphene

D

crithmene
99-85-4

crithmene

E

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With Conventional beta-zeolite at 70℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Reflux;A 8.7%
B 7.2%
C 19.7%
D 4.4%
E 30.7%
With mesoporous beta type zeolite at 70℃; for 0.5h;
terephthalonitrile
623-26-7

terephthalonitrile

methanol
67-56-1

methanol

(-)-α-pinene
7785-26-4

(-)-α-pinene

cis-6-(4-cyanophenyl)-4-(1-methoxy-1-methylethyl)-1-methylcyclohexene
122723-00-6, 122744-26-7

cis-6-(4-cyanophenyl)-4-(1-methoxy-1-methylethyl)-1-methylcyclohexene

trans-6-(4-cyanophenyl)-4-(1-methoxy-1-methylethyl)-1-methylcyclohexene
122723-00-6, 122744-26-7

trans-6-(4-cyanophenyl)-4-(1-methoxy-1-methylethyl)-1-methylcyclohexene

C

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With biphenyl In acetonitrile for 72h; Irradiation;A 23%
B 28%
C n/a
Acetic acid (2Z,6E)-3,7-dimethyl-8-trimethylsilanyl-octa-2,6-dienyl ester
79433-09-3

Acetic acid (2Z,6E)-3,7-dimethyl-8-trimethylsilanyl-octa-2,6-dienyl ester

limonene.
138-86-3

limonene.

Conditions
ConditionsYield
With methylaluminium bis(trifluoroacetate) In hexane at 25℃; for 17h;28%
limonene.
138-86-3

limonene.

1-methyl-4-isopropenylbenzene
1195-32-0

1-methyl-4-isopropenylbenzene

Conditions
ConditionsYield
With n-butyllithium; potassium 2-methylbutan-2-olate Mechanism; 1) r.t., 17 h, 2) reflux, 6 h; further reagent: D2O;100%
Multi-step reaction with 3 steps
1: copper (II)-formate; nickel-formate / 175 °C
2: manganese (II)-acetate; lead (II)-acetate / 45 °C / Einleiten von Luft
3: charcoal / 53 Torr
View Scheme
Multi-step reaction with 3 steps
1: activated copper; nickel / 175 °C
2: manganese (II)-acetate; lead (II)-acetate / 45 °C / Einleiten von Luft
3: charcoal / 53 Torr
View Scheme
limonene.
138-86-3

limonene.

1,4-dimethyl but-2-enedioate
23055-10-9

1,4-dimethyl but-2-enedioate

C16H24O4

C16H24O4

Conditions
ConditionsYield
With iodine at 250℃; for 1h; Autoclave; Inert atmosphere;99.5%
limonene.
138-86-3

limonene.

p-menth-1-ene
61585-35-1

p-menth-1-ene

Conditions
ConditionsYield
With fac-[Mn(1,2-bis(di-isopropylphosphino)ethane)(CO)3(CH2CH2CH3)]; hydrogen In diethyl ether at 25℃; under 37503.8 Torr; for 24h;99%
With borohydride exchange resin-nickel boride In methanol for 1h; Heating;95%
With LaNi5 hydride In tetrahydrofuran; methanol for 11h; Ambient temperature;88%
limonene.
138-86-3

limonene.

4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

Conditions
ConditionsYield
With iron(III) chloride; sodium; ethylenediamine at 50 - 100℃; Inert atmosphere;99%
With hydrogen at 350℃; under 760.051 Torr;91%
With 5 weight% palladium(0) nanoparticles supported on mesoporous natural phosphate In neat (no solvent) for 24h; Reflux;88%
limonene.
138-86-3

limonene.

α-limonene diepoxide
96-08-2

α-limonene diepoxide

Conditions
ConditionsYield
With sodium percarbonate; acetic anhydride In acetic acid butyl ester at 60℃; for 12h; Product distribution / selectivity;99%
With dihydrogen peroxide; sodium acetate; acetic anhydride In toluene at 5 - 25℃; for 5h; Time; Temperature;92%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 15℃; for 1.83333h;86%
limonene.
138-86-3

limonene.

4-isopropenyl-1-methylcyclohexane
6252-33-1

4-isopropenyl-1-methylcyclohexane

Conditions
ConditionsYield
With C40H56N2RuSi4; hydrogen In toluene at 25℃; under 7600.51 Torr; for 6h; Schlenk technique; Autoclave;99%
With C40H56FeN2Si4(2-); hydrogen In 1,2-dimethoxyethane at 80℃; under 7600.51 Torr; for 10h; Schlenk technique; Autoclave;50%
limonene.
138-86-3

limonene.

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

4,4,5,5-tetramethyl-2-((R)-2-((S)-4-methylcyclohex-3-en-1-yl)propyl)-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-((R)-2-((S)-4-methylcyclohex-3-en-1-yl)propyl)-1,3,2-dioxaborolane

B

4,4,5,5-tetramethyl-2-((R)-2-((S)-4-methylcyclohex-3-en-1-yl)propyl)-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-((R)-2-((S)-4-methylcyclohex-3-en-1-yl)propyl)-1,3,2-dioxaborolane

Conditions
ConditionsYield
With C26H36CoN3O In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; Glovebox; enantioselective reaction;A 97%
B n/a
3-Mercaptopropyltriethoxysilane
14814-09-6

3-Mercaptopropyltriethoxysilane

limonene.
138-86-3

limonene.

(3-((2-(4-methylcyclohex-3-en-1-yl)propan-2-yl)thio)propyl)triethoxysilane

(3-((2-(4-methylcyclohex-3-en-1-yl)propan-2-yl)thio)propyl)triethoxysilane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 6.5h; Inert atmosphere;97%
With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 6h; Inert atmosphere;97%
With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 6h; Inert atmosphere;97%
3-Mercaptopropyltriethoxysilane
14814-09-6

3-Mercaptopropyltriethoxysilane

limonene.
138-86-3

limonene.

(3-((2-(4-methyl-3-((3-(triethoxysilyl)propyl)thio)cyclohexyl)propan-2-yl)thio)propyl)triethoxysilane

(3-((2-(4-methyl-3-((3-(triethoxysilyl)propyl)thio)cyclohexyl)propan-2-yl)thio)propyl)triethoxysilane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In toluene at 70℃; for 6h; Inert atmosphere;97%
limonene.
138-86-3

limonene.

Limonene oxide
1195-92-2

Limonene oxide

Conditions
ConditionsYield
With oxygen; manganese triacetate; pivalaldehyde In various solvent(s) at 25℃; for 1h;96%
With 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane; potassium hydroxide In acetonitrile at 20℃; for 0.833333h;96%
With oxygen; sodium hydrogencarbonate; isobutyraldehyde; RuCl2(biox)2 In dichloromethane at 25℃; for 8h;92%
1,3,3,5,5-hexamethyltrisiloxane
1189-93-1

1,3,3,5,5-hexamethyltrisiloxane

limonene.
138-86-3

limonene.

C26H52O2Si3

C26H52O2Si3

Conditions
ConditionsYield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 60℃; for 6h; Inert atmosphere;96%
chloroform
67-66-3

chloroform

limonene.
138-86-3

limonene.

4-(1-methyl-2,2-dichlorocyclopropyl)-7,7-dichloro-1-methylbicyclo<4.1.0>heptane
37608-28-9

4-(1-methyl-2,2-dichlorocyclopropyl)-7,7-dichloro-1-methylbicyclo<4.1.0>heptane

Conditions
ConditionsYield
With sodium hydroxide for 3h; Irradiation; ultrasound;95%
ethanol
64-17-5

ethanol

limonene.
138-86-3

limonene.

4-(2-ethoxypropan-2-yl)-1-methylcyclohex-1-ene
25571-13-5, 27153-54-4

4-(2-ethoxypropan-2-yl)-1-methylcyclohex-1-ene

Conditions
ConditionsYield
askanite-bentonite clay at 20℃; for 70h; Addition; Etherification;95%
3-mercaptopropionic acid
107-96-0

3-mercaptopropionic acid

limonene.
138-86-3

limonene.

3-((2-(4-methylcyclohex-3-en-1-yl)propan-2-yl)thio)propionic acid

3-((2-(4-methylcyclohex-3-en-1-yl)propan-2-yl)thio)propionic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol at 70℃; for 6h; Inert atmosphere;95%
C10H10BrNO2S2

C10H10BrNO2S2

limonene.
138-86-3

limonene.

C20H27NS

C20H27NS

Conditions
ConditionsYield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tert-dodecanethiol; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; Irradiation; chemoselective reaction;93%
tetraethylammonium acetate
1185-59-7

tetraethylammonium acetate

limonene.
138-86-3

limonene.

B

carvyl acetate
97-42-7

carvyl acetate

Conditions
ConditionsYield
With palladium diacetate; p-benzoquinone In chloroform at 20℃; Product distribution; Further Variations:; Reagents;A 90%
B 10%
Bromotrichloromethane
75-62-7

Bromotrichloromethane

limonene.
138-86-3

limonene.

4-(2-bromo-4,4,4-trichlorobutan-2-yl)-1-methylcyclohex-1-ene

4-(2-bromo-4,4,4-trichlorobutan-2-yl)-1-methylcyclohex-1-ene

Conditions
ConditionsYield
With disodium tetracarbonylferrate In tetrahydrofuran at 25℃; for 16h; Glovebox; Inert atmosphere;90%
With Benzoylformic acid In Petroleum ether for 18h; Sealed tube; Irradiation; Green chemistry;79%
limonene.
138-86-3

limonene.

(3R*)-6-oxo-3-(prop-1-en-2-yl)heptanal
7086-79-5

(3R*)-6-oxo-3-(prop-1-en-2-yl)heptanal

Conditions
ConditionsYield
With 1H-imidazole; sodium periodate; MnCl-TPP-(PEO750)4 In water; acetonitrile at 20℃; for 24h;89%
Stage #1: limonene. With ozone In methanol; dichloromethane at -78℃; for 2.5h; Inert atmosphere;
Stage #2: With dimethylsulfide In dichloromethane at -78 - 20℃; for 3h; Inert atmosphere;
80%
With oxygen; uranyl acetate In pyridine Irradiation;
Multi-step reaction with 2 steps
1: O2 / UO2(OAc)2*2H2O / pyridine / Irradiation
2: benzene / 30 h / Heating
View Scheme
trichloroacetonitrile
545-06-2

trichloroacetonitrile

limonene.
138-86-3

limonene.

(E)-1,1,1-Trichloro-4-(4-methyl-cyclohex-3-enyl)-pent-3-en-2-one
97963-00-3

(E)-1,1,1-Trichloro-4-(4-methyl-cyclohex-3-enyl)-pent-3-en-2-one

Conditions
ConditionsYield
With boron trichloride In dichloromethane at -78℃;89%
Hexafluoroacetone
684-16-2

Hexafluoroacetone

limonene.
138-86-3

limonene.

C13H16F6O
1146219-31-9

C13H16F6O

Conditions
ConditionsYield
With 3 Å molecular sieves at 100℃; for 0.166667h; Microwave irradiation;89%
isopropyl alcohol
67-63-0

isopropyl alcohol

limonene.
138-86-3

limonene.

4-(1-isopropoxy-1-methylethyl)-1-methyl-cyclohexene
27153-55-5

4-(1-isopropoxy-1-methylethyl)-1-methyl-cyclohexene

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane at 0 - 20℃; for 1.2h;87%
limonene.
138-86-3

limonene.

4-aminotiophenol
1193-02-8

4-aminotiophenol

4-((2-(4-methylcyclohex-3-en-1-yl)propan-2-yl)thio)aniline

4-((2-(4-methylcyclohex-3-en-1-yl)propan-2-yl)thio)aniline

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In ethanol at 70℃; for 12h; Inert atmosphere;87%
limonene.
138-86-3

limonene.

A

α-limonene diepoxide
96-08-2

α-limonene diepoxide

B

Limonene oxide
1195-92-2

Limonene oxide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; (dimethylammonium)[MoO3(Hbpdc)]*1.7H2O at 55℃; for 24h; Solvent; Temperature; Time; regioselective reaction;A n/a
B 86%
With tert.-butylhydroperoxide; C72H100Mo8N8O26 In decane; α,α,α-trifluorotoluene at 55℃; for 24h; regioselective reaction;A 76%
B 22%
Stage #1: limonene. With MoO(NtBu)(2,6-iPr2C6H3O)2py In toluene at 20℃; Inert atmosphere;
Stage #2: With tert.-butylhydroperoxide In decane; toluene at 90℃; for 4h; Inert atmosphere;
A 26%
B 58%
limonene.
138-86-3

limonene.

4-chlorobenzohydroximoyl chloride
28123-63-9

4-chlorobenzohydroximoyl chloride

5-methyl-5-[4'-methylcyclohex-3'-enyl]-3-parachlorophenyl-4,5-dihydroisoxazole

5-methyl-5-[4'-methylcyclohex-3'-enyl]-3-parachlorophenyl-4,5-dihydroisoxazole

Conditions
ConditionsYield
Stage #1: 4-chlorobenzohydroximoyl chloride With triethylamine
Stage #2: limonene. In dichloromethane at 20℃; for 72h;
85%
chloroform
67-66-3

chloroform

limonene.
138-86-3

limonene.

A

7,7-Dichloro-4-isopropenyl-1-methyl-bicyclo[4.1.0]heptane
83387-33-1

7,7-Dichloro-4-isopropenyl-1-methyl-bicyclo[4.1.0]heptane

B

4-(1-methyl-2,2-dichlorocyclopropyl)-7,7-dichloro-1-methylbicyclo<4.1.0>heptane
37608-28-9

4-(1-methyl-2,2-dichlorocyclopropyl)-7,7-dichloro-1-methylbicyclo<4.1.0>heptane

Conditions
ConditionsYield
With potassium hydroxide; 18-crown-6 ether In dichloromethane at 40℃; for 4h; Yields of byproduct given;A n/a
B 84%
With potassium hydroxide; p-t-butylcalix<6>arene derivative In dichloromethane at 40℃; for 4h;A 55%
B 17%
With potassium hydroxide; p-t-butylcalix<6>arene derivative In dichloromethane at 30℃; Rate constant; other catalyst;
Conditions
ConditionsYield
With formic acid; phosphoric acid In dichloromethane at 75℃;83%
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