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Cas Database

65253-04-5

65253-04-5

Identification

  • Product Name:(-)-8-Phenylmenthol

  • CAS Number: 65253-04-5

  • EINECS:

  • Molecular Weight:232.366

  • Molecular Formula: C16H24O

  • HS Code:29061900

  • Mol File:65253-04-5.mol

Synonyms:(1R,2S,5R)-5-Methyl-2-(2-phenylpropan-2-yl)cyclohexan-1-ol;(R)-8-Phenylmenthol;(?)-Phenmenthol;(1R,2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanol;ZINC02539581;AC1MBFYC;LT03210883;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:(-)-8-Phenylmenthol
  • Packaging:1g
  • Price:$ 360
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:(-)-8-Phenylmenthol >98.0%(GC)
  • Packaging:200mg
  • Price:$ 79
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(?)-8-Phenylmenthol 98%
  • Packaging:1g
  • Price:$ 346
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(?)-8-Phenylmenthol 98%
  • Packaging:250mg
  • Price:$ 89.1
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  • Manufacture/Brand:Crysdot
  • Product Description:(1R,2S,5R)-5-Methyl-2-(2-phenylpropan-2-yl)cyclohexanol 95+%
  • Packaging:1g
  • Price:$ 325
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  • Manufacture/Brand:Chem-Impex
  • Product Description:(-)-8-Phenylmenthol,≥98%(GC) ≥98%(GC)
  • Packaging:200MG
  • Price:$ 89.69
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:(-)-8-PHENYLMENTHOL 95.00%
  • Packaging:1G
  • Price:$ 956.26
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:(-)-8-PHENYLMENTHOL 95.00%
  • Packaging:250MG
  • Price:$ 650.03
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  • Manufacture/Brand:Alichem
  • Product Description:(1R,2S,5R)-5-Methyl-2-(2-phenylpropan-2-yl)cyclohexanol
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  • Price:$ 344.5
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  • Manufacture/Brand:AK Scientific
  • Product Description:(-)-8-Phenylmenthol
  • Packaging:200mg
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Relevant articles and documentsAll total 46 Articles be found

Diastereoselective sulfa-Michael reactions controlled by a biomass-derived chiral auxiliary

Klepp, Julian,Podversnik, Harald,Puschnig, Johannes,Wallace, Andrew,Greatrex, Ben W.

supporting information, p. 3894 - 3903 (2019/06/18)

A family of chiral auxiliaries derived from the lignocellulosic biomass pyrolysis product levoglucosenone (LGO) has been screened in the sulfa-Michael reaction. When promoted by inorganic bases with potassium counterions, the auxiliary with geminal benzyl substituents showed diastereoselectivity up to 90:10 for a broad range of α,β-unsaturated esters.

Diastereoselective photocycloaddition reactions of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furans governed by chiral auxiliaries and hydrogen bonding interactions

Maeda, Hajime,Koshio, Norihiro,Tachibana, Yuko,Chiyonobu, Kazuhiko,Konishi, Gen-ichi,Mizuno, Kazuhiko

, p. 7 - 17 (2017/09/12)

By using chiral auxiliaries and hydrogen bonding interactions, we have developed diastereoselective photocycloaddition of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furan derivatives. In photoreactions of (?)-menthyl 2-naphthalenecarboxylate with furan and 3-furanmethanol, respective maximum 48% and 40% diastereomeric excesses (d.e.) are observed. In photoreactions of di-8-phenyl-(?)-menthyl 2,3-naphthalenedicarboxylate with 3-furanmethanol, maximum 67% d.e. is obtained. Use of solvents of low polarity, low temperatures and low furan concentration leads to increased diastereoselectivities. Variable-temperature (VT) NMR and fluorescence quenching studies indicate that hydrogen bonding interactions between the carbonyl oxygen of naphthalenecarboxylic acid esters and the OH group in 3-furanmethanol take place in both the ground and excited states. The results of computational studies show that geometries of C2 symmetric naphthalenedicarboxylate reactants are important in governing the high diastereoselectivity in the photoreactions of 2,3-naphthalenedicarboxylates.

Method for Highly Enantioselective Ligation of Two Chiral C(sp3) Stereocenters

Bhimireddy, Eswar,Corey

supporting information, p. 11044 - 11047 (2017/08/22)

A method is described for the joining of two α-lithiated C(sp3) stereocenters efficiently and with retention of configuration. The key step involves the effective removal of two electrons from a chiral organocuprate R2CuLi, by i-propyl 2,4-dinitrobenzoate to form a Cu(III) complex that undergoes at -90 °C accelerated reductive elimination enantioselectively and exclusively without the formation of free radicals.

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

Letzel, Matthias C.,Sch?fer, Hans J.,Fr?hlich, Roland

, p. 33 - 42 (2017/02/15)

Diastereoselective radical coupling was achieved with chiral auxiliaries. The radicals were generated by anodic decarboxylation of five malonic acid derivatives. These were prepared from benzyl malonates and four menthol auxiliaries. Coelectrolyses with 3,3-dimethylbutanoic acid in methanol at platinum electrodes in an undivided cell afforded hetero-coupling products in 22-69% yield with a diastereoselectivity ranging from 5 to 65% de. Electrolyses without a coacid led to diastereomeric homo-coupling products in 21-50% yield with ratios of diastereomers being 1.17:2.00:0.81 to 7.03:2.00. The stereochemistry of the new stereogenic centers was confirmed by X-ray structure analysis and 13C NMR data.

Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol

Crossley, Steven W. M.,Martinez, Ruben M.,Guevara-Zuluaga, Sebastián,Shenvi, Ryan A.

, p. 2620 - 2623 (2016/06/15)

Hydrogen atom transfer (HAT) circumvents a disfavored Friedel-Crafts reaction in the derivatization of the inexpensive monoterpene isopulegol. A variety of readily prepared aryl and heteroaryl sulfonates undergo a formal hydroarylation to form 8-arylmenthols, privileged scaffolds for asymmetric synthesis, as typified by 8-phenylmenthol. High stereoselectivity is observed in related systems. This use of HAT significantly extends the chiral pool from the inexpensive monoterpene isopulegol.

Process route upstream and downstream products

Process route

(1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate
71804-27-8

(1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

Conditions
Conditions Yield
With potassium hydroxide; In ethanol; Ambient temperature;
100%
With potassium hydroxide; In ethanol; water; Reflux; Schlenk technique; Inert atmosphere;
99%
With water; potassium hydroxide; In ethanol; for 2h; Reflux;
97%
With lithium aluminium tetrahydride;
95%
With potassium hydroxide; In ethanol; water; for 2h; Reflux;
27%
With potassium hydroxide; In ethanol; Heating;
(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (2R)-4,4-dimethyl-2-phenylpentanoate

(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (2R)-4,4-dimethyl-2-phenylpentanoate

(2R)-4,4-dimethyl-2-phenylpentanol

(2R)-4,4-dimethyl-2-phenylpentanol

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 60h; Inert atmosphere;
93%
83%
C<sub>31</sub>H<sub>36</sub>O<sub>2</sub>S

C31H36O2S

(S)-3-phenyl-3-(phenylthio)propan-1-ol

(S)-3-phenyl-3-(phenylthio)propan-1-ol

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; for 20h; Inert atmosphere; Schlenk technique;
20 mg
93%
(-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon
97371-54-5

(-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

Conditions
Conditions Yield
With sodium; In isopropyl alcohol; toluene; for 1h; Heating;
48%
With sodium; isopropyl alcohol; In toluene; for 8h; optical yield given as %de; diastereoselective reaction; Reflux; Inert atmosphere;
36%
(S)-Hydroxy-(1R,3aR,6aR)-1,3a,6,6a-tetrahydro-pentalen-1-yl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(S)-Hydroxy-(1R,3aR,6aR)-1,3a,6,6a-tetrahydro-pentalen-1-yl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

(S)-(1R,3aR,6aR)-1-(1,3a,6,6a-Tetrahydro-pentalen-1-yl)-ethane-1,2-diol
104393-65-9

(S)-(1R,3aR,6aR)-1-(1,3a,6,6a-Tetrahydro-pentalen-1-yl)-ethane-1,2-diol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran;
95%
83%
(S)-Hydroxy-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(S)-Hydroxy-(1S,3aS,6aS)-1,3a,6,6a-tetrahydro-pentalen-1-yl-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

(S)-(1S,3aS,6aS)-1-(1,3a,6,6a-Tetrahydro-pentalen-1-yl)-ethane-1,2-diol
104393-66-0

(S)-(1S,3aS,6aS)-1-(1,3a,6,6a-Tetrahydro-pentalen-1-yl)-ethane-1,2-diol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran;
95%
83%
(2R,6R)-2-(l-phenmenthyloxy)-6-phenyl-4-<(tert-butyldimethylsilyl)-oxy>-2H(5,6)-dihydropyran
104130-23-6

(2R,6R)-2-(l-phenmenthyloxy)-6-phenyl-4-<(tert-butyldimethylsilyl)-oxy>-2H(5,6)-dihydropyran

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

(R)-2-phenyl-2,3-dihydro-4H-pyran-4-one
88198-68-9

(R)-2-phenyl-2,3-dihydro-4H-pyran-4-one

Conditions
Conditions Yield
With trifluoroacetic acid; In dichloromethane; 0 deg C, 1 h; room temperature, 2 h;
85%
87%
C<sub>25</sub>H<sub>36</sub>O<sub>2</sub>

C25H36O2

((1R,2S)-1,2-dimethylcyclohex-3-enyl)methanol
162868-74-8

((1R,2S)-1,2-dimethylcyclohex-3-enyl)methanol

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
5.9 mg
10.7 mg
(-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]piperidine-2-carboxylate
1427281-87-5

(-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1S)-1-phenylethyl]piperidine-2-carboxylate

(-)-(2S,4R)-2-(hydroxymethyl)-1-[(1S)-1-phenylethyl]piperidin-4-ol
1427281-91-1

(-)-(2S,4R)-2-(hydroxymethyl)-1-[(1S)-1-phenylethyl]piperidin-4-ol

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Inert atmosphere;
0.181 g
0.23 g
(-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1R)-1-phenylethyl]piperidine-2-carboxylate
1427281-89-7

(-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1R)-1-phenylethyl]piperidine-2-carboxylate

(-)-(2S,4R)-2-(hydroxymethyl)-1-[(1R)-1-phenylethyl]piperidin-4-ol
1427281-93-3

(-)-(2S,4R)-2-(hydroxymethyl)-1-[(1R)-1-phenylethyl]piperidin-4-ol

(-)-8-phenylmenthol
65253-04-5

(-)-8-phenylmenthol

Conditions
Conditions Yield
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Inert atmosphere;
0.196 g
0.27 g

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