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78-70-6 Usage

Chemical Synthesis

It can be prepared synthetically starting from myrcene or from dehydrolinalool; it can be obtained by fractional distilla tion and subsequent rectification from the oils of Cajenne rosewood (Licasia guaianensis, Ocotea caudata), Brazil rosewood (Ocotea parviflora), Mexican linaloe, shiu (Cinnamomum camphora Sieb. var. linalooifera) and coriander seeds (Coriandrum sativum L.).

Occurrence

The optically active forms (d- and l-) and the optically inactive form occur naturally in more than 200 oils from herbs, leaves, flowers and wood; the l-form is present in the largest amounts (80 to 85%) in the distillates from leaves of Cinnamomum camphora var. orientalis and Cinnamomum camphora var. occidentalis and in the distillate from Cajenne rosewood; it also has been reported in champaca, ylang-ylang, neroli, Mexican linaloe, bergamot and lavandin; a mixture of d- and l-linalool has been reported in Brazil rosewood (85%); the d-form has been found in palmarosa, mace, sweet orange-flower distillate, petitgrain, coriander (60 to 70%), marjoram and Orthodon linalooliferum (80%); the inactive form has been reported in clary sage, jasmine and Nectandra elaiophora. Also reported found in over 280 products including apple, citrus peel oils and juices, berries, grapes, guava, celery, peas, potato, tomato, cinnamon, cloves, cassia, cumin, ginger, mentha oils, mustard, nutmeg, pepper, thymus, cheeses, grape wines, butter, milk, rum, cider, tea, passion fruit, olive, mango, beans, coriander, cardamom and rice.

Uses

linalool is a fragrant component of both lavender and coriander. It can be incorporated into cosmetics for perfuming, deodorant, or odor-masking activity.

Metabolism

The metabolism of 14C-labelled linalool in the rat was studied by Parke, Rahman & Walker (1974a). An intragastric dose of 500 mg linalool/kg body weight was largely (93%) excreted within 72 hr in the urine (55%), faeces (23%) and expired air (15%). The radioactivity remaining after 72 hr was located mainly in the liver (0-5%), gut (0-6%), skin (0-8%) and skeletal muscle (1-2%). Rapid urinary excretion indicated that linalool was rapidly absorbed from the gut, while delay in excretion in the expired air suggested that linalool might enter intermediary metabolism and also be metabolized by conjugation in the bile and urine. Ip administration of 20 mg linalool indicated that enterohepatic circulation occurred, resulting in a short-term metabolic load on the liver and delayed faecal excretion. The metabolism of large doses in the rat, with rapid excretion of linalool and its metabolites, suggests no long-term hazard from tissue accumulation on chronic exposure to concentrations normally encountered in foods, although enterohepatic circulation might prolong the metabolic load on the liver over a relatively short period. A study of the effects of linalool and other terpenoids on hepatic drug-metabolizing enzymes suggested that these compounds induce the enzymes involved in their own metabolism. Linalool, which is metabolized by reduction and conjugation with glucuronic acid, increased the activity of 4-nitrobenzoate reductase but did not increase other enzymes studied (Parke & Rahman, 1969). Linalool can be metabolized by micro- organisms. l-Linalool was partially oxidized by incubation with Aspergillus nig er (Goto, 1967). The linalool content of grape essential oil decreased during must fermentation and wine formation (Rodopulo, Egorov, Bezzubov, Kormakova & Megrelidze, 1972). A strain of Pseudomonas pseudomallei, isolated from soil, metabolized linalool with the formation of camphor, 4-methyl-4-vinylbutyrolactone, 4-methyl- trans-3-hexenoic acid, and 2,6-dimethyl-6- hydroxy- trans-2,7-octadienoic acid (Mizutani, Hayashi, Ueda & Tatsumi, 1971).

Uses

1. It is used for the preparation of cosmetics, soaps, detergents, food and other flavors. 2. GB 276011996 states it is classified into food flavor allowed for temporary use. It is mainly used for the preparation of flavors or aromatic seasoning of pineapple, peach, and chocolate. 3. It is widely presented in flowers, fruits, stems, leaves, roots and green Rosa Chinensis viridiflora. It has a wide range of application, not only for all the floral flavors, such as sweet bean curd, jasmine, Convallaria majalis, lilac, etc., it can also be applied in fruit flavor type, Fen-flavor type, wood flavor type, aldehyde flavor type, oriental flavor type, amber scent type, chypre type, fern-type and other non-flower type of flavor. It can also be used in formulating orange leaf, bergamot, lavender, and some kinds of artificial oils such as hybrid lavender oil. It is mostly used in soap or flavor. It can be used for food flavor. 4. Linalool is a kind of important spices and is the blending raw materials for producing various kinds of artificial oil, also used extensively for the manufacturing of various esters of linalool. Linalool has an important position in the ester-type perfumes and other cosmetic formulations. Linalool can generate citral through oxidation and can also be used for the synthesis of many other kinds of spices.

Chemical Properties

It is colorless liquid with fragrance similar with bergamot. It is insoluble in water, but miscible with ethanol and ether.

Uses

Linalool is one of the allergens of Ylang-Ylang oil (extract from Cananga odorata).

Spices

Linalool is a kind of terpene alcohols and is one kind of famous perfume compounds. It is the mixture of two isomers (α-linalool and β-linalool). It is extracted from camphor oil (from camphor tree) or synthesized from the α-pinene or β-pinene contained in turpentine. It is colorless oily liquid with sweet and tender fresh flowers and a fragrance of Convallaria majalis. It is easily soluble in organic solvents such as ethanol, ethylene glycol and diethyl ether but insoluble in water and glycerol. It is easily subject to isomerization and is relatively stable in alkali. It has a density (25 ℃) of 0.860~0.867, the refractive index (20 ℃) of ??1.4610~1.4640, optical rotation (20 ℃) of ??-12 ° ~-18 °, the boiling point being 197~199 ℃, and the flash point (open ended) of 78 ℃. Linalool with alcohol content higher than 95% is an important spices for floral fragrance used for perfumes, soaps and other fragrance industry. It is also widely used in flowers oils of lending lily, lilac, sweet pea, and orange blossom as well as the compound perfume of amber incense, oriental fragrance, and aldehyde-type fragrance, cosmetics perfumes and food flavor. It can also be used as the spices of lemon, lime, orange, grape, apricot, pineapple, plum, peach, cardamom, cocoa, and chocolate. Drug containing 92.5% alcohol content is used as the raw material drugs in the pharmaceutical industry for producing isophytol which is an important intermediate in the preparation of vitamin E. It can also be used as raw material for producing valuable spices linalyl acetate and some other esters. Linalool belongs to open chain terpene tertiary alcohol. It has two double bonds. However, it contains an asymmetric carbon atom, so it has three kinds of optical isomers. In Nature, all three kinds of isomers are present with the amount of I-body being the highest, accounting for 70% to 80% of the total amount of the three. I-body is mostly presented in linalool oil (containing about 80 to 90%), champa, lavender oil, lime oil, neroli oil, clary sage oil, aloeswood oil, lemon oil, rose oil, cananga orodrata oil and some other kinds of essential oil; its d-body is mostly presented in coriander oil (containing about 60% to 70%), sweet orange oil, nutmeg oil, palmarosa oil and other kinds of essential oil; its dl-form is mainly presented in the essential oils of clary sage and jasmine. All the three kinds are transparent colorless oily liquid with lilies and citrus-like fragrance. In addition, because of the close distance between its hydroxy group and allyl group, its chemical nature is very influential. In the presence of sodium metal in ethanol solution, it can be easily be reduced to generate dihydro-myrcene; in the presence of a platinum catalyst or Raney nickel catalyst, it can be reduced to the tetrahydro linalool to become saturated alcohol. Owing that it is a kind of tertiary alcohol, in strongly acidic medium, it can subject to isomerization; in dilute acid medium, it undergoes dehydration to become esters. It is stable in alkaline medium. The LD50 of oral administration for Rat is 2790 mg /kg.

Uses

perfume use

Description

Linalool has a typical floral odor free from camphoraceous and terpenic notes.1 Synthetic linalool exhibits a cleaner and fresher note than the natural product. It can be prepared synthetically starting from myrcene or from dehydrolinalool.The optically active forms (d- and ι-) and the optically inactive form occur naturally in more than 2 0 0 oils from herbs, leaves, flowers, and wood; the ι-form is present in the largest amounts (80 - 85%) in the distillates from leaves of Cinnamomum cam phora var. orientalis and Cinnamomum camphora var. occidentalis and in the distillate from Cajenne rosewood; it also has been reported in: champaca, ylang-ylang, neroli, Mexican linaloe, ber gamot, lavandin, and others; a mixture of d- and ι-linalool has been reported in Brazil rosewood (85%); the d-form has been found in palmarosa, mace, sweet orange-flower distillate, petit grain, coriander (60 - 70%), marjoram, Orthodon linalooliferum (80%), and others; the inactive form has been reported in clary sage, jasmine, and Nectandra elaiophora.

Definition

ChEBI: A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.

Contact allergens

Linalool is a terpene chief constituent of linaloe oil,also found in oils of Ceylon cinnamon, sassafras,orange flower, bergamot, Artemisia balchanorum, ylang-ylang. This frequently used scented substance is a sensitizer by the way of primary or secondary oxida-tion products. As a fragrance allergen, linalool has to be mentioned by name in cosmetics within the EU

Chemical Properties

Linalool occurs as one of its enantiomers in many essential oils, where it is often the main component. (3R)- (?)-Linalool, for example, occurs at a concentration of 80–85% in Ho oils from Cinnamomum camphora; rosewood oil contains about 80%. (3S)-(+)- Linalool makes up 60–70% of coriander oil (“coriandrol”). Linalool is used frequently in perfumery for fruity notes and for many floral fragrance compositions (lily of the valley, lavender, and neroli). Because of its relatively high volatility, it imparts naturalness to top notes. Since linalool is stable in alkali, it can be used in soaps and detergents. Linalyl esters can be prepared from linalool.Most of the manufactured linalool is used in the production of vitamin E.

Pharmacology

l-Linalool showed no sedative action in the mouse motility test when injected ip at a dose of 100 mg/kg (Binet, Binet, Miocque, Roux & Bernier, 1972). but Wagner & Sprinkmeyer (1973) reported that linalool depressed spontaneous motility of mice at doses of 31-6 and 100 mg/kg. Linalool showed spasmolytic action against carbachol-, histamine- and barium chloride-induced contractions in isolated guinea-pig ileum, the ED50 being about 100-200 mg/litre (Wagner & Sprinkmeyer. 1973). and in the isolated rat duodenum, contractions caused by 0.05 /ig acetylcholine/ml were inhibited by 50% by 10 μg l-linalool/ml (Binet et al. 1972). Linalool showed slight papavarinelike and very slight atropine-like antispasmodic action on small intestine isolated from the mouse (Imaseki & Kitabatake, 1962). In studies carried out by Atanassova-Shopova et al. (1973), the ED50 for preventing tonic hyperextension of the hind limbs of rats from electric shock was found to be 135 mg/kg given ip. Linalool had a marked anticonvulsive and protective effect on pentylenetetrazol convulsions in mice at 150,175 and 200 mg/kg and in rats at 200 and 300 mg/kg. It showed a slight antistrychnine effect in mice at high and toxic doses (300 mg/kg), reduced motor activity of mice at 100 mg/kg, and at 50 mg/kg slightly decreased the motor activity of amphetamine- or caffeine-stimulated mice. The TD50 (neurotoxic dose) of linalool for influencing motor co-ordination of mice in the Rota-rod test was found to be 178 mg/kg. Linalool at doses of 50 or 100 mg/kg prolonged the narcotic effects of hexobarbitone, alcohol and chloral hydrate. The equilibrium and spontaneous or reflex activity of the goldfish, Carassium auratus, was disturbed by exposure to aquarium water containing a 0-13 ml/litre concentration of a suspension containing 1 ml linalool plus 9 ml of a 10% aqueous solution of Tween 80, and the agressiveness of the male fighting fish, Betta splendens, was only very slightly inhibited by exposure to aquarium water containing 0-3 ml of the same suspension of linalool/litre (Binet, 1972). Linalool and other terpene alcohols were found to be useful in man as sedatives and spasmolytics when administered in doses of 0.01-1 g, the effects having been tested in mice, goldfish, and rats (Laboratoires Meram, 1966). Linalool depressed frog-heart activity in doses above 0-2 mg/g (Lysenko, 1962). Vasodilation by direct action of linalool upon the blood vessels was demonstrated by Northover & Verghese (1962). An iv dose of 9.2 mg/kg was required to produce a 25% fall in systolic arterial blood pressure in the anaesthetized dog and a hypotensive response was also observed in the decerebrated and despinalized dog. A dose of 0.05 g in fluid perfusing the leg of an anaesthetized dog or the isolated ear of a rabbit produced a maximum increase of 120% or 90%, respectively, in venous outflow over pre-injection values. Linalool dilated the small blood vessels of the exposed mesorchium of the anaesthetized mouse, lowering the threshold for electronic stimulation. Incubation of human, bovine and canine aortae in 015 M-linalool failed to stabilize the structure of the aortic wall proteins against hydrothermal shrinkage (Milch, 1965). Linalool inhibited incorporation of acetic acid or mevalonic acid into total or digitonin-precipitable nonsaponifiable lipids by rat-liver homogenates (Gey, Pletscher, Isler, Riiegg, Saucy & Wiirsch, 1960).

Chemical Properties

Linalool has a typical pleasant floral odor, free from camphoraceous and terpenic notes. Synthetic linalool exhibits a cleaner and fresher note than the natural products.

Toxicity

Adl 0~0.5 mg/kg (FAO/WHO.1994). GRAS (FDA, §182.60, 2000). LD50 2790 (rat, oral administration).

Physical properties

Properties. Racemic linalool is, similarly to the individual enantiomers, a colorless liquid with a floral, fresh odor, reminiscent of lily of the valley. However, the enantiomers differ slightly in odor. Together with its esters, linalool is one of the most frequently used fragrance substances and is produced in large quantities. In the presence of acids, linalool isomerizes readily to geraniol, nerol, and α-terpineol. It is oxidized to citral, for example, by chromic acid. Oxidation with peracetic acid yields linalool oxides, which occur in small amounts in essential oils and are also used in perfumery. Hydrogenation of linalool gives tetrahydrolinalool, a stable fragrance material. Its odor is not as strong as, but is fresher than, that of linalool. Linalool can be converted into linalyl acetate by reaction with ketene or with an excess of boiling acetic anhydride.

Production method

1. The commercial linalool is mainly isolated from natural essential oils including aloeswood oil, rosewood oil, coriander oil, and linalyl oil. Using efficient distillation column for fractionation can produce crude product of linalool with secondary fractionation obtaining finished product with a content being higher than 90%. Synthetic linalool can use β-pinene as raw material with pyrolysis yielding myrcene. Treatment with hydrogen chloride generates a mixture comprising linalyl chloride. Linalyl chloride can have reaction with potassium hydroxide (or potassium carbonate) to generate linalool. 2. It is existed in free form in camphor oil: using acetyl boric anhydride converting the linalool contained in camphor oil into acidic borate ester, and then through distillation, re-crystallization, and saponification to obtain the finished product. 3. Use 6-methyl-5-hept-ene-2-ketone to have condensation reaction with sodium acetylide to obtain dehydrolinalool, further undergoing reduction reaction at wet ether solution with metal sodium to obtain the linalool.

Limited use

FEMA (mg/kg): Soft drinks 2.0; cold drink 3.6; candy 8.4; Bakery 9.6; pudding Class 2.3; gum 0.80 to 90; meat 40.

Lavender

Linalool is the major antimicrobial ingredient of lavender essential oils. It can inhibit the growth of 17 bacteria (including Gram-positive and Gram-negative bacteria) and 10 fungi. In vitro experiments show that the narrow-leaf lavender essential oils, at concentrations below 1%, can inhibit the newly penicillin I resistant Staphylococcus aureus and Enterococcus faecalis.

Content Analysis

Take 10 mL of sodium sulfate pre-dried sample and put it into a 125 mL of glass-stoppered Erlenmeyer flask pre-cooled by an ice bath. Add 20 mL of dimethylaniline (toluidine product) in cold oil and mix thoroughly. Add 8 mL of acetyl chloride and 5 mL of acetic anhydride, cool for several minutes, then place at room temperature for 30min, then immerse the flask in a water bath and maintained for 16h at 40 °C ± 1 °C; Apply ice-water for washing acetyl oil for three times with 75 mL each time. Then repeatedly wash with 25 mL of 5% sulfuric acid solution until the separated acid layer no longer exhibiting cloudy-like or doesn’t have further dimethylaniline odor coming out so that dimethylaniline was further removed. First apply 10 mL of 10% sodium carbonate solution for washing acetylated oil, followed by successive washing with water until washing to being neutral to litmus. After complete drying with anhydrous sodium sulfate, accurately weigh the acetylation oil of about 1.2g, and then measure it according to the "ester assay" (OT-18). Linalool (C10H18O) content (L) is calculated as follows; L = 7.707 (b-s) /W=0.021 (b-s) Where L--linalool content, %; b-the consumed volume of 0.5 mol/L of hydrochloric acid in blank test, Mi; s--the consumed volume of 0.5 mol/L of hydrochloric acid for titration of the sample solution, ml; IV-sample sample, g. Method II, measure the amount using non-polar column protocol based on the Gas Chromatography Method (GT-10-4). The above information is edited by the chemicalbook of Dai Xiongfeng.

Taste threshold values

Taste characteristics at 5 ppm: green, apple and pear with an oily, waxy, slightly citrus note.

Synthesis Reference(s)

Tetrahedron, 33, p. 579, 1977 DOI: 10.1016/S0040-4020(77)80019-7

Chemical Properties

liquid

Aroma threshold values

Detection: 4 to 10 ppb

Anticancer Research

Studies of antitumor activities and toxicity were done on solid S-180 tumor-bearingSwiss albino mice. It results in an induction of oxidative stress with an antitumoractivities result. In comparison with cyclophosphamide, antioxidant effects wereobserved in the liver and modulation of proliferation of spleen cells in tumor-bearingmice challenged with lipopolysaccharides, while both were seriously affected bycyclophosphamide (Costa et al. 2015).

Preparation

In the 1950s, nearly all linalool used in perfumery was isolated from essential oils, particularly from rosewood oil. Currently, this method no longer plays a commercial role. Since linalool is an important intermediate in the manufacture of vitamin E, several large-scale processes have been developed for its production. Preferred starting materials and/or intermediates are the pinenes and 6-methyl-5-hepten- 2-one. Most perfumery-grade linalool is synthetic. 1) Isolation from essential oils: Linalool can be isolated by fractional distillation of essential oils, for example, rosewood oil and coriander oil, of which Brazilian rosewood oil was the most important. 2) Synthesis from α-pinene: α-Pinene from turpentine oil is selectively hydrogenated to cis-pinane, which is oxidized with oxygen in the presence of a radical initiator to give a mixture of about 75% cis-pinane and 25% transpinane hydroperoxide.The mixture is reduced to the corresponding pinanols either with sodium bisulfite (NaHSO3) or with a catalyst. The pinanols can be separated by fractional distillation and are pyrolyzed to linalool: (?)-α- pinene yields cis-pinanol and (+)-linalool, whereas (?)-linalool is obtained from trans-pinanol. 3) Synthesis from ??-pinene: For a description of this route, see under Geraniol. Addition of hydrogen chloride to myrcene (obtained from β-pinene) results in a mixture of geranyl, neryl, and linalyl chlorides. Reaction of this mixture with acetic acid–sodium acetate in the presence of copper(I) chloride gives linalyl acetate in 75–80% yield. Linalool is obtained after saponification. 4) Synthesis from 6-methyl-5-hepten-2-one:The total synthesis of linalool starts with 6-methyl-5-hepten-2-one; several large-scale processes have been developed for synthesizing this compound: a. Addition of acetylene to acetone results in the formation of 2-methyl-3- butyn-2-ol, which is hydrogenated to 2-methyl-3-buten-2-ol in the presence of a palladium catalyst.This product is converted into its acetoacetate derivative with diketene or with ethyl acetoacetate. The acetoacetate undergoes rearrangement when heated (Carroll reaction) to give 6-methyl-5-hepten-2-one: b. In another process, 6-methyl-5-hepten-2-one is obtained by reaction of 2-methyl-3-buten-2-ol with isopropenyl methyl ether followed by a Claisen rearrangement: c. A third synthesis starts fromisoprene, which is converted into 3-methyl-2- butenyl chloride by addition of hydrogen chloride. Reaction of the chloride with acetone in the presence of a catalytic amount of an organic base leads to 6-methyl-5-hepten-2-one: d. In another process, 6-methyl-5-hepten-2-one is obtained by isomerization of 6-methyl-6-hepten-2-one.The latter can be prepared in two steps from isobutylene and formaldehyde. 3-Methyl-3-buten-l-ol is formed in the first step and is converted into 6-methyl-6-hepten-2-one by reaction with acetone. 6-Methyl-5-hepten-2-one is converted into linalool in excellent yield by base-catalyzed ethynylation with acetylene to dehydrolinalool. This is followed by selective hydrogenation of the triple bond to a double bond in the presence of a palladium carbon catalyst.

78-70-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (L0048)  Linalool  >96.0%(GC) 78-70-6 25mL 112.00CNY Detail
TCI America (L0048)  Linalool  >96.0%(GC) 78-70-6 500mL 398.00CNY Detail
Sigma-Aldrich (61706)  Linalool  certified reference material, TraceCERT® 78-70-6 61706-50MG 816.66CNY Detail
Sigma-Aldrich (51782)  Linalool  analytical standard 78-70-6 51782-1ML 1,349.01CNY Detail
Sigma-Aldrich (00350190)  Linalool  primary pharmaceutical reference standard 78-70-6 00350190-100MG 3,450.33CNY Detail

78-70-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name linalool

1.2 Other means of identification

Product number -
Other names LINALLOL

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:78-70-6 SDS

78-70-6Synthetic route

3-(tert-butyldimethylsiloxy)-3,7-dimethyl-1,6-octadiene
89155-68-0

3-(tert-butyldimethylsiloxy)-3,7-dimethyl-1,6-octadiene

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

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

Conditions
ConditionsYield
With iodine In methanol microwave irradiation;100%
With P(MeNCH2CH2)3N In dimethyl sulfoxide at 80℃; for 36h; desilylation;81%
<(dimethyl-1,5 ethyliden-1 hexen-4 yl-1)oxy> trimethyl silane
59632-77-8

<(dimethyl-1,5 ethyliden-1 hexen-4 yl-1)oxy> trimethyl silane

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

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

Conditions
ConditionsYield
With iodine In methanol microwave irradiation;100%
3,7-dimethyloct-6-en-1-yn-3-ol
29171-20-8

3,7-dimethyloct-6-en-1-yn-3-ol

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

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

Conditions
ConditionsYield
With hydrogen; PdAu in polystyrene-block-poly-4-vinylpyridine micelles In toluene at 90℃; under 760 Torr; for 0.316667h;99.8%
With hydrogen In toluene at 20℃; under 38002.6 Torr; for 12h; Autoclave; chemoselective reaction;99%
With quinoline; oct-1-ene; hydrogen; Lindlar's catalyst95%
(bicyclo<2.2.1>heptene-5 yle-2)-dimethyl-1,5 hexene-4 ol-1
86361-07-1

(bicyclo<2.2.1>heptene-5 yle-2)-dimethyl-1,5 hexene-4 ol-1

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

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

Conditions
ConditionsYield
at 550℃; under 0.01 Torr;98%
6-Methyl-hept-5-en-2-on
110-93-0

6-Methyl-hept-5-en-2-on

vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

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

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

Conditions
ConditionsYield
With zinc(II) chloride In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst; Solvent; Inert atmosphere; Cooling with ice;96.3%
With tetrahydrofuran
6-Methyl-hept-5-en-2-on
110-93-0

6-Methyl-hept-5-en-2-on

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

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

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

Conditions
ConditionsYield
With zinc(II) chloride In tetrahydrofuran at 20℃; for 5h; Reagent/catalyst; Solvent; Inert atmosphere; Cooling with ice;95.2%
With tetrahydrofuran; diethyl ether
In tetrahydrofuran at -78℃; Addition;
geraniol
624-15-7

geraniol

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

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

Conditions
ConditionsYield
With vanadia; triethylamine at 110 - 140℃; under 45.0045 Torr; for 48h; Temperature; Pressure; Reagent/catalyst;94.5%
2-[(1-ethenyl-1,5-dimethyl-4-hexen-1-yl)oxy]tetrahydro-2H-pyran
38844-76-7, 120414-17-7, 120414-18-8

2-[(1-ethenyl-1,5-dimethyl-4-hexen-1-yl)oxy]tetrahydro-2H-pyran

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

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

Conditions
ConditionsYield
bis(trimethylsilyl)sulphate In methanol; 1,2-dichloro-ethane for 0.333333h; Ambient temperature;94%
With bismuth(lll) trifluoromethanesulfonate In methanol; N,N-dimethyl-formamide at 110℃; for 22h;79%
linalyl benzoate
126-64-7

linalyl benzoate

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

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

Conditions
ConditionsYield
With sodium hydroxide In methanol; dichloromethane at 30℃; for 5.5h; Solvent;93%
Z-1-(phenylseleno)-3,7-dimethylocta-2,6-diene
350048-99-6

Z-1-(phenylseleno)-3,7-dimethylocta-2,6-diene

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

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

Conditions
ConditionsYield
With dihydrogen peroxide90%
Toluene-4-sulfonic acid 3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester

Toluene-4-sulfonic acid 3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester

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

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

Conditions
ConditionsYield
With aluminum oxide; tellurium(2-) for 2h;86%
With aluminum oxide; tellurium(2-) for 0.158333h; Product distribution; other reaction conditions, reaction time, reagent, solvent;83%
3,7-dimethyl-3-methylsulfanylmethoxy-octa-1,6-diene
59304-70-0

3,7-dimethyl-3-methylsulfanylmethoxy-octa-1,6-diene

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

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

Conditions
ConditionsYield
With trityl tetrafluoroborate In dichloromethane for 0.25h; Ambient temperature;80%
2-(4-methylpent-3-en-1-yl)-2-vinyloxirane
153079-55-1

2-(4-methylpent-3-en-1-yl)-2-vinyloxirane

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

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

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 16h; Reduction;78%
Nerol
106-25-2

Nerol

A

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

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

B

Geraniol
106-24-1

Geraniol

C

terpineol
98-55-5

terpineol

Conditions
ConditionsYield
With bis-trimethylsilanyl peroxide; bis(acetylacetonate)oxovanadium In dichloromethane at 25℃; for 7h;A 70%
B 11%
C 3%
bis(acetylacetonate)oxovanadium; bis-trimethylsilanyl peroxide In dichloromethane at 25℃; for 7h;A 70 % Chromat.
B 11 % Chromat.
C 3 % Chromat.
bis(acetylacetonate)oxovanadium; bis-trimethylsilanyl peroxide In dichloromethane at 25℃; for 7h; Product distribution;A 70 % Chromat.
B 11 % Chromat.
C 3 % Chromat.
methyl geranyl selenide

methyl geranyl selenide

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

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

Conditions
ConditionsYield
With Benzyl phenyl selenoxide; potassium carbonate; potassium dioxotetrahydroxoosmate(VI); 1,4-bis(9-O-dihydroquinidine)phthalazine In tert-butyl alcohol at 20℃; for 7h;70%
3,7-dimethyl-6-(phenylthio)octa-1,6-dien-3-ol
477482-29-4

3,7-dimethyl-6-(phenylthio)octa-1,6-dien-3-ol

(1RS,2SR)-1,2-dimethyl-3-(methylethylidene)-cyclopentan-1-ol

(1RS,2SR)-1,2-dimethyl-3-(methylethylidene)-cyclopentan-1-ol

(1RS,2RS)-1,2-dimethyl-3-(methylethylidene)-cyclopentan-1-ol

(1RS,2RS)-1,2-dimethyl-3-(methylethylidene)-cyclopentan-1-ol

C

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

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

Conditions
ConditionsYield
With n-butyllithium; 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium In tetrahydrofuran at -20℃; for 5h;A 10%
B 70%
C 18%
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

Nerol
106-25-2

Nerol

C

terpineol
98-55-5

terpineol

Conditions
ConditionsYield
With bis-trimethylsilanyl peroxide; bis(acetylacetonate)oxovanadium In dichloromethane at 25℃; for 7h;A 68%
B 8%
C 2%
bis(acetylacetonate)oxovanadium; bis-trimethylsilanyl peroxide In dichloromethane at 25℃; for 7h;A 68 % Chromat.
B 8 % Chromat.
C 2 % Chromat.
bis(acetylacetonate)oxovanadium; bis-trimethylsilanyl peroxide In dichloromethane at 25℃; for 7h; Product distribution;A 68 % Chromat.
B 8 % Chromat.
C 2 % Chromat.
phenyliodnane

phenyliodnane

((E)-3,7-Dimethyl-octa-2,6-dienyltellanyl)-benzene
172215-49-5

((E)-3,7-Dimethyl-octa-2,6-dienyltellanyl)-benzene

A

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

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

B

N-[3,7-dimethyl-1,6-octadien-3-yl]toluenosulfonamide
172215-51-9

N-[3,7-dimethyl-1,6-octadien-3-yl]toluenosulfonamide

Conditions
ConditionsYield
In ethanol at 25℃; for 20h;A 10%
B 68%
((E)-3,7-Dimethyl-octa-2,6-dienyltellanyl)-benzene
172215-49-5

((E)-3,7-Dimethyl-octa-2,6-dienyltellanyl)-benzene

A

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

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

B

N-[3,7-dimethyl-1,6-octadien-3-yl]toluenosulfonamide
172215-51-9

N-[3,7-dimethyl-1,6-octadien-3-yl]toluenosulfonamide

Conditions
ConditionsYield
With [N-(p-tolylsulfonyl)imino]phenyliodinane In ethanol at 25℃; for 20h;A 12%
B 68%
3,7-Dimethyl-octa-2,6-dienyl-phenylsulfoxid
31236-12-1

3,7-Dimethyl-octa-2,6-dienyl-phenylsulfoxid

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

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

Conditions
ConditionsYield
With sodium thiophenolate In methanol 1.) reflux, 7 h, dark, 2.) room temperature, 18 h;66%
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

Conditions
ConditionsYield
With germacrene A synthase from Nostoc sp. PCC7120 (NS1) In terpene synthase buffer at 25℃; for 18h; Enzymatic reaction;A 66%
B 25%
C 9%
(2R*,3R*)-2,3-epoxy-3,7-dimethyl-6-octenyl acetate
50727-95-2

(2R*,3R*)-2,3-epoxy-3,7-dimethyl-6-octenyl acetate

A

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

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

B

Nerol
106-25-2

Nerol

Conditions
ConditionsYield
With tellurium; lithium triethylborohydride In tetrahydrofuran for 0.25h; Ambient temperature;A 62%
B 5.5%
With tellurium; lithium triethylborohydride In tetrahydrofuran for 0.25h; Product distribution; Mechanism; Ambient temperature; other reducing Te agent; various time; also in the presence of fluoride ion;A 62%
B 5.5%
phenyliodnane

phenyliodnane

((Z)-3,7-Dimethyl-octa-2,6-dienyltellanyl)-benzene
172215-50-8

((Z)-3,7-Dimethyl-octa-2,6-dienyltellanyl)-benzene

A

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

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

B

N-[3,7-dimethyl-1,6-octadien-3-yl]toluenosulfonamide
172215-51-9

N-[3,7-dimethyl-1,6-octadien-3-yl]toluenosulfonamide

Conditions
ConditionsYield
In ethanol at 25℃; for 20h;A 12%
B 59%
((Z)-3,7-Dimethyl-octa-2,6-dienyltellanyl)-benzene
172215-50-8

((Z)-3,7-Dimethyl-octa-2,6-dienyltellanyl)-benzene

A

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

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

B

N-[3,7-dimethyl-1,6-octadien-3-yl]toluenosulfonamide
172215-51-9

N-[3,7-dimethyl-1,6-octadien-3-yl]toluenosulfonamide

Conditions
ConditionsYield
With [N-(p-tolylsulfonyl)imino]phenyliodinane In ethanol at 25℃; for 20h;A 12%
B 59%
(1,5-dimethyl-1-vinylhex-4-enyloxy)triethylsilane
89984-47-4

(1,5-dimethyl-1-vinylhex-4-enyloxy)triethylsilane

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

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

Conditions
ConditionsYield
10percent Pd/C In methanol for 70h; Heating;56%
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%
{Co(C5H5N)((CH3)2CCHCH2CH2C(CH3)(CHCH2)OO)(CH3C(NOH)C(CH3)NO)2}

{Co(C5H5N)((CH3)2CCHCH2CH2C(CH3)(CHCH2)OO)(CH3C(NOH)C(CH3)NO)2}

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

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

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate In methanol redn. of the Co compd. in methanolic NaOH with NaBH4;40%
linalool acetate
115-95-7

linalool acetate

A

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

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

B

Geraniol
106-24-1

Geraniol

C

terpineol
98-55-5

terpineol

Conditions
ConditionsYield
for 36h; fermentation with cultures of Papaver bracteatum;A 24%
B 14%
C 4.5%
2,3-epoxygeranial
16996-12-6

2,3-epoxygeranial

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

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

Conditions
ConditionsYield
With hydrazine In acetonitrile at 0℃;23%
Geraniol
106-24-1

Geraniol

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

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

Conditions
ConditionsYield
With PDS; PS-TEMPO; Ag-Al2O3 In water; toluene at 80℃; for 2.5h; Product distribution / selectivity;20%
With water at 200℃;
With hydrogenchloride entsteht Chlorid,durch Digerieren mit alkoh.Kali;
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

acetic anhydride
108-24-7

acetic anhydride

linalool acetate
115-95-7

linalool acetate

Conditions
ConditionsYield
With magnesium(II) perchlorate at 20℃; for 3h;100%
With Tri-n-octylamine; dmap at 125℃; for 13 - 16h; Product distribution / selectivity; Heating / reflux;95%
With chloro-trimethyl-silane for 0.166667h; Ambient temperature; neat or in dichloromethane solution;90%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

1-Methyl-2-cyclopenten-1-ol
40459-88-9

1-Methyl-2-cyclopenten-1-ol

Conditions
ConditionsYield
With Grubbs catalyst first generation In dichloromethane at 20℃; for 1h;100%
With second generation Grubbs' catalyst analogue In dichloromethane at 20℃; for 0.1h;94%
With Grubbs catalyst first generation In chloroform at 20℃; Alkene (Olefin) Metathesis; Inert atmosphere;79%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

A

1-Methyl-2-cyclopenten-1-ol
40459-88-9

1-Methyl-2-cyclopenten-1-ol

B

isobutene
115-11-7

isobutene

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst second generation at 20℃; for 0.75h; Neat (no solvent); Inert atmosphere;A 100%
B n/a
With C35H46Cl2N2ORu In benzene-d6 at 60℃; Catalytic behavior; Reagent/catalyst; Sealed tube;
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

1,3,3-trimethyl-2-chloromethylcyclohexene

1,3,3-trimethyl-2-chloromethylcyclohexene

Conditions
ConditionsYield
Stage #1: 3,7-dimethylocta-1,6-dien-3-ol With thionyl chloride; sodium hydroxide In water; 1,2-dichloro-ethane at 40 - 45℃; for 3h;
Stage #2: With sulfuric acid In water; 1,2-dichloro-ethane at 70 - 75℃; for 5h; Solvent; Reagent/catalyst; Temperature;
99.1%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

chloroform
67-66-3

chloroform

5-(2,2-Dichlor-3,3-dimethylcyclopropyl)-3-methyl-1-penten-3-ol
64670-24-2

5-(2,2-Dichlor-3,3-dimethylcyclopropyl)-3-methyl-1-penten-3-ol

Conditions
ConditionsYield
With potassium hydroxide; tert-butylammonium hexafluorophosphate(V) In benzene at 20℃; for 7h;99%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride Ambient temperature;
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

dihydrolinalool
18479-51-1

dihydrolinalool

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 18h;99%
With oxygen; 5-ethyl-10-methyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]pteridin-5-ium perchlorate; hydrazine hydrate; phenol In acetonitrile at 25 - 30℃; for 5h; chemoselective reaction;96%
With iron(III) chloride hexahydrate; hydrazine hydrate In ethanol at 20℃; for 24h;95%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

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

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

linalool acetate
115-95-7

linalool acetate

Conditions
ConditionsYield
With Cp*2Sm(THF)2; cyclohexanone oxime acetate In toluene at 50℃; for 15h;99%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

trimethylsilylazide
4648-54-8

trimethylsilylazide

<(dimethyl-1,5 ethyliden-1 hexen-4 yl-1)oxy> trimethyl silane
59632-77-8

<(dimethyl-1,5 ethyliden-1 hexen-4 yl-1)oxy> trimethyl silane

Conditions
ConditionsYield
tetrabutylammomium bromide at 70℃; for 3h;99%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

tert-butyldimethylsilyl N-phenylbenzimidate
404392-70-7

tert-butyldimethylsilyl N-phenylbenzimidate

3-(tert-butyldimethylsiloxy)-3,7-dimethyl-1,6-octadiene
89155-68-0

3-(tert-butyldimethylsiloxy)-3,7-dimethyl-1,6-octadiene

Conditions
ConditionsYield
With pyridinium triflate In tetrahydrofuran at 25℃; for 0.5h;99%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

3-(tert-butyldimethylsiloxy)-3,7-dimethyl-1,6-octadiene
89155-68-0

3-(tert-butyldimethylsiloxy)-3,7-dimethyl-1,6-octadiene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 3h;98.5%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

2,2-bis(4-dimethylsilylphenoxy)-4,4,6,6-bis[spiro(2’,2’’-dioxy-1’,1’’-biphenyl)]cyclotriphosphazene

2,2-bis(4-dimethylsilylphenoxy)-4,4,6,6-bis[spiro(2’,2’’-dioxy-1’,1’’-biphenyl)]cyclotriphosphazene

C60H74N3O8P3Si2

C60H74N3O8P3Si2

Conditions
ConditionsYield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 90℃; chemoselective reaction;98%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-(tert-butyldimethylsiloxy)-3,7-dimethyl-1,6-octadiene
89155-68-0

3-(tert-butyldimethylsiloxy)-3,7-dimethyl-1,6-octadiene

Conditions
ConditionsYield
With pyridine In dichloromethane at 25℃; under 11250900 Torr; for 24h;97%
With iodine In 1,2-dichloro-ethane at 71 - 72℃; for 0.0333333h; microwave irradiation;92%
With P(MeNCH2CH2)3N at 80℃; for 24h;90%
With pyridine In dichloromethane at 25℃; under 7500600 Torr; for 24h; Product distribution; other pressures, other time;79%
N-ethyl-N,N-diisopropylamine at 100℃; for 40h;53%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

4-(allyloxy)-4-oxobutanoic acid
3882-09-5

4-(allyloxy)-4-oxobutanoic acid

Succinic acid 1,5-dimethyl-1-vinylhex-4-enyl ester prop-1-ynyl ester

Succinic acid 1,5-dimethyl-1-vinylhex-4-enyl ester prop-1-ynyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; under 11250900 Torr; for 24h;97%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

C22H31NOSi
404392-72-9

C22H31NOSi

(1,5-dimethyl-1-vinyl-hex-4-enyloxy)-triisopropyl-silane

(1,5-dimethyl-1-vinyl-hex-4-enyloxy)-triisopropyl-silane

Conditions
ConditionsYield
With pyridinium triflate In tetrahydrofuran at 50℃; for 14h;97%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

triethylsilyl chloride
994-30-9

triethylsilyl chloride

(1,5-dimethyl-1-vinylhex-4-enyloxy)triethylsilane
89984-47-4

(1,5-dimethyl-1-vinylhex-4-enyloxy)triethylsilane

Conditions
ConditionsYield
With 1-methyl-1H-imidazole-3-oxide for 8h; Heating;97%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

hexakis((4-dimethylsilyl)phenoxy)cyclotriphosphazene

hexakis((4-dimethylsilyl)phenoxy)cyclotriphosphazene

C108H174N3O12P3Si6

C108H174N3O12P3Si6

Conditions
ConditionsYield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 90℃; regioselective reaction;97%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

Linalool oxide
15249-34-0

Linalool oxide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In chlorobenzene at 80℃; for 5h;96%
With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In decane; benzene for 5h; Heating;62%
With Fusarium concentricum In dimethyl sulfoxide at 28 - 30℃; for 120h; Microbiological reaction;42%
piperidine
110-89-4

piperidine

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

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

C15H29NO

C15H29NO

Conditions
ConditionsYield
With 2,4,6-Triisopropylthiophenol; [Ir(2-(2,4-difluorophenyl)-5-(methyl)pyridinyl)2(4,4′-bis(tert-butyl)bipyridine)]*PF6 In toluene at 20℃; Irradiation; regioselective reaction;96%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

A

Linalool oxide
15249-34-0

Linalool oxide

B

6,7-epoxylinalool
15249-35-1

6,7-epoxylinalool

Conditions
ConditionsYield
With monoperoxyphthalic acid; sodium hydrogencarbonate In water at 1 - 3℃; for 1h; Yields of byproduct given;A n/a
B 95%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

6,7-epoxylinalool
15249-35-1

6,7-epoxylinalool

Conditions
ConditionsYield
With dihydrogen peroxide; formamide In methanol; water at 50℃; for 3h;95%
With sodium peroxoborate tetrahydrate; Biliton; acetonitrile In water at 20℃; for 9h;84%
With dihydrogen peroxide; ethyl cyanoformate In acetonitrile Ambient temperature;82%
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

N-trimethylsilylaniline
3768-55-6

N-trimethylsilylaniline

<(dimethyl-1,5 ethyliden-1 hexen-4 yl-1)oxy> trimethyl silane
59632-77-8

<(dimethyl-1,5 ethyliden-1 hexen-4 yl-1)oxy> trimethyl silane

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 0.0833333h;95%
With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 5℃; for 0.0166667h;
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

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

(+/-)-2,6,6-trimethylbicyclo<3.2.0>heptan-endo-2-ol
92471-17-5

(+/-)-2,6,6-trimethylbicyclo<3.2.0>heptan-endo-2-ol

Conditions
ConditionsYield
With copper (I) trifluoromethane sulfonate benzene In diethyl ether for 14h; Irradiation;94%
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