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Cas Database

5240-32-4

5240-32-4

Identification

  • Product Name:Cyclohexanol,1-ethynyl-, 1-acetate

  • CAS Number: 5240-32-4

  • EINECS:226-040-0

  • Molecular Weight:166.22

  • Molecular Formula: C10H14 O2

  • HS Code:2915390090

  • Mol File:5240-32-4.mol

Synonyms:Cyclohexanol,1-ethynyl-, acetate (6CI,7CI,8CI,9CI); 1-Acetoxy-1-ethynylcyclohexane;1-Ethynylcyclohexanol acetate; 1-Ethynylcyclohexyl acetate; ENT 7068; NSC 22257

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Safety information and MSDS view more

  • Signal Word:No signal word.

  • Hazard Statement:none

  • 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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Relevant articles and documentsAll total 56 Articles be found

Enhancing the Catalytic Activity of 4-(Dialkylamino)pyridines by Conformational Fixation

Heinrich, Markus R.,Klisa, Heike Sabine,Mayr, Herbert,Steglich, Wolfgang,Zipse, Hendrik

, p. 4826 - 4828 (2003)

Six times more active than DMAP (1), the tricyclic DMAP analogue 2 catalyzes the acetylation of a tertiary alcohol with acetic anhydride. The experimental results can be rationalized by quantum chemical calculations.

Development of a triazinedione-based dehydrative condensing reagent containing 4-(dimethylamino)pyridine as an acyl transfer catalyst

Liu, Jie,Fujita, Hikaru,Kitamura, Masanori,Shimada, Daichi,Kunishima, Munetaka

supporting information, p. 4712 - 4719 (2021/06/11)

A new triazinedione-based reagent, (N,N′-dialkyl)triazinedione-4-(dimethylamino)pyridine (ATD-DMAP) was developed for the operationally simple dehydrative condensation of carboxylic acids. This reagent comprises an ATD core and DMAP as the leaving group, which is liberated into the reaction system to accelerate acyl transfer reactions. Upon adding ATD-DMAP to a mixture of carboxylic acids and alcohols in the presence of an amine base, the corresponding esters were formed rapidly at room temperature. Moreover, dehydrative condensation between carboxylic acids and amines using ATD-DMAP proceeded in high yield.

Regioselective Synthesis of Multifunctional Allylic Amines; Access to Ambiphilic Aziridine Scaffolds

McLaughlin, Mark G.,Roberts, Dean D.

supporting information, p. 4463 - 4467 (2021/06/28)

We describe, for the first time, a highly regioselective hydrosilylation of propargylic amines. The reaction utilizes a PtCl2/XantPhos catalyst system to deliver hydrosilanes across the alkyne to afford multifunctional allylic amines in high yields. The reaction is tolerant to a wide variety of functional groups and provides high value intermediates with two distinct functional handles. The synthetic applicability of the reaction has been shown through the synthesis of diverse ambiphilic aziridines.

Enhancing catalytic activity of pyridines: Via para -iminophosphorano substituents

Charlton, Grant D.,Dyker, C. Adam,Richard, Nicholas A.

, p. 9167 - 9171 (2021/11/13)

Four pyridines decorated with π-donating iminophosphorano substituents (R3PN-) in the 4-position were assessed as acylation catalysts. These catalysts display high sensitivity to the groups at phosphorus, with activities that are well correlated to the corresponding Hammett-type substituent constants (σp+), and can achieve superior activity over the most active dialkylamino-substituted pyridines. Iminophosphorano-substituted pyridines represent an easily accessible, tunable, and highly active class of nucleophilic organocatalysts. This journal is

Synthesis and evaluation of 1,1,7,7-tetramethyl-9-azajulolidine (TMAJ) as a highly active derivative of N,N-dimethylaminopyridine

Tsutsumi, Tomohiro,Saitoh, Arisa,Kasai, Tomoyo,Chu, MengYue,Karanjit, Sangita,Nakayama, Atsushi,Namba, Kosuke

supporting information, (2020/05/28)

1,1,7,7-Tetramethyl-9-azajulolidine (TMAJ), which theoretical studies have suggested as a highly active DMAP analog, was synthesized for the first time. The catalytic activity of TMAJ was confirmed by the acetylation reactions of various tert-alcohols. TMAJ showed much higher catalytic activity than DMAP and one of the highest activity levels among the conventional DMAP analogs. These experimental results were in good agreement with the previous theoretical studies.

Synthesis of 1,2-Dihydro-Substituted Aniline Analogues Involving N -Phenyl-3-aza-Cope Rearrangement Using a Metal-Free Catalytic Approach

Alduhaish, Osamah,Varala, Ravi,Adil, Syed Farooq,Khan, Mujeeb,Siddiqui, Mohammed Rafiq H.,Alwarthan, Abdulrhman,Alam, M. Mujahid

, (2020/10/02)

An efficient metal-free domino reaction leading to structural/electronically divergent 1,2-dihydropyridines from easily accessible propargyl vinyl anilines via N-phenyl 3-aza-Cope sigmatropic rearrangement is reported with good to excellent yields using 1,2-dichlorobenzene as solvent under thermal conditions. Spirocyclic substitution is also tolerated under the present optimized conditions.

Process route upstream and downstream products

Process route

acetic anhydride
108-24-7

acetic anhydride

1-Ethynylcyclohexan-1-ol
78-27-3

1-Ethynylcyclohexan-1-ol

1-acetoxy-1-ethynyl cyclohexane
5240-32-4

1-acetoxy-1-ethynyl cyclohexane

Conditions
Conditions Yield
indium(III) chloride; In acetonitrile; at 20 ℃; for 0.5h;
100%
With magnesium(II) perchlorate; at 20 ℃; for 0.5h;
100%
tetrafluoroboric acid; silica gel; at 20 ℃; for 6h;
96%
With scandium tris(trifluoromethanesulfonate); In acetonitrile; at -20 ℃; for 0.5h;
95%
With magnesium(II) perchlorate; for 1h;
95%
With iron(III) p-toluenesulfonate hexahydrate; In acetonitrile; at 0 ℃; for 5h;
95%
CoCl2; In acetonitrile; at 80 ℃; for 2h;
93%
With bismuth oxide perchlorate; at 20 ℃; for 0.5h;
93%
With magnesium bis(trifluoromethane solfonyl)imide; at 20 ℃; for 1h;
92%
ruthenium trichloride; In acetonitrile; at 20 ℃; for 7h;
92%
copper(II) bis(tetrafluoroborate); at 20 ℃; for 0.25h;
90%
With zirconium(IV) chloride; In acetonitrile; at 20 ℃; for 1.5h;
90%
With perchloric acid; In acetonitrile; at 20 ℃; for 0.25h;
90%
With lithium perchlorate; at 25 ℃; for 48h;
89%
With ruthenium trichloride; at 40 ℃; for 3h; Inert atmosphere; Ionic liquid;
87%
With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
85%
With magnesium(II) perchlorate; at 0 - 20 ℃; for 1h; Inert atmosphere;
85%
With tributylphosphine; triethylamine; for 1h; Ambient temperature;
65%
With 3-(N-Me-4-aminoPy)propyl functionalysed mesoporous silica; triethylamine; In benzene; at 60 ℃; for 6h;
54%
With graphite oxide; In acetonitrile; at 20 ℃; for 24h; Green chemistry;
40%
With sulfuric acid;
With phosphoric acid;
Heating;
bismuth(lll) trifluoromethanesulfonate; In acetonitrile; at 25 ℃; for 4h;
94 % Chromat.
With triethylamine; 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; In chloroform-d1; at 20 ℃;
With bismuth(lll) trifluoromethanesulfonate; In water; acetonitrile; at 25 ℃; for 4h;
94 % Chromat.
With triethylamine; dmap; In chloroform-d1; at 23 ℃;
With triethylamine; In dichloromethane; at 25 ℃; for 3h;
In water; at 200 ℃; for 0.00275h; under 37503.8 Torr;
86 % Chromat.
With dmap; triethylamine; In dichloromethane; at 22 - 25 ℃; for 40h;
With triethylamine; dmap; In chloroform-d1; at 23 ℃; Kinetics;
With triethylamine; 1-(4-acetyl-3,4-dihydro-2H-pyrido[3,4-b]pyrazin-1-yl)ethanone; In chloroform-d1; at 23 ℃; Kinetics;
With triethylamine; 1,4-diethyl-1,2,3,4-tetrahydro-pyrido[3,4-b]pyrazine; In chloroform-d1; at 23 ℃; Kinetics;
With triethylamine; 1,4-dimethyl-1,2,3,4-tetrahydro-pyrido[3,4-b]pyrazine; In chloroform-d1; at 23 ℃; Kinetics;
With triethylamine; 5,10-diethyl-5,5a,6,7,8,9,9a,10-octahydropyrido[3,4-b]quinoxaline; In chloroform-d1; at 23 ℃; Kinetics;
With triethylamine; 1-(5-ethyl-5a,6,7,8,9,9a-hexahydro-5H-pyrido[3,4-b]quinoxalin-10-yl)ethanone; In chloroform-d1; at 23 ℃; Kinetics;
With triethylamine; 1-ethyl-4-methyl-2,3-diphenyl-1,2,3,4-tetrahydropyrido[3,4-b]pyrazine; In chloroform-d1; at 23 ℃; Kinetics;
With triethylamine; 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; In chloroform-d1; at 23 ℃; Kinetics;
With triethylamine; 4-pyrrolidin-1-ylpyridine; In chloroform-d1; at 23 ℃; Kinetics;
With 2-(3-hexylpyridin-4-yl)-1,1,3,3-tetramethylguanidine; triethylamine; In chloroform-d1; at 23 ℃; Reagent/catalyst; Solvent; Kinetics;
With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
563 mg
With 5-ethyl-10-hexyl-5,5a,6,7,8,9,9a,10-octahydropyrido[3,4-b]quinoxaline; triethylamine; In chloroform-d1; at 20 ℃; Reagent/catalyst; Kinetics; Inert atmosphere;
With pyridine;
With 1,6-diethyl-2,3,5,6-tetrahydro-1H,4H-1,3a,6,8-tetraaza-phenalene; triethylamine; In chloroform-d1; at 23 ℃; Reagent/catalyst; Solvent; Kinetics;
With 4-(N-ethyl-N-methylamino)pyridine; triethylamine; In chloroform-d1; at 23 ℃; Reagent/catalyst; Kinetics;
With 1,4-diethyl-1,2,3,4-tetrahydropyrazino[2,3-d]pyridazine; triethylamine; In benzene-d6; at 35 ℃; Solvent; Concentration; Reagent/catalyst; Catalytic behavior;
acetic anhydride; 1-Ethynylcyclohexan-1-ol; With triethylamine; In dichloromethane; at 0 ℃; for 0.25h; under 760.051 Torr;
With dmap; In dichloromethane; at 0 - 20 ℃; for 4h; under 760.051 Torr;
1.67 g
With 1,1,7,7-tetramethyl-9-azajulolidine; triethylamine; In chloroform-d1; at 20 ℃; for 1.5h; Reagent/catalyst; Time; Inert atmosphere;
With dmap; triethylamine; In dichloromethane; at 20 ℃;
With dmap; triethylamine; In dichloromethane;
With 4-(Triphenylphosphoranylidenamino)pyridin; triethylamine; In chloroform-d1; at 20 ℃; Reagent/catalyst;
1-Ethynylcyclohexan-1-ol
78-27-3

1-Ethynylcyclohexan-1-ol

acetyl chloride
75-36-5

acetyl chloride

1-acetoxy-1-ethynyl cyclohexane
5240-32-4

1-acetoxy-1-ethynyl cyclohexane

Conditions
Conditions Yield
1-Ethynylcyclohexan-1-ol; With pyridine; dmap; In dichloromethane; at 0 ℃; for 0.0833333h;
acetyl chloride; In dichloromethane; at 25 ℃; for 7h;
47%
With dmap; triethylamine; In dichloromethane; at 0 ℃; for 5h;
1-Ethynylcyclohexan-1-ol
78-27-3

1-Ethynylcyclohexan-1-ol

acetic acid
64-19-7,77671-22-8

acetic acid

1-acetoxy-1-ethynyl cyclohexane
5240-32-4

1-acetoxy-1-ethynyl cyclohexane

Conditions
Conditions Yield
With perchloric acid; at 20 ℃; for 6h;
90%
With 4-methyl-morpholine; C16H20N5O2(1+)*Cl(1-); In dichloromethane; at 20 ℃; for 30h; Molecular sieve;
64%
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; Inert atmosphere;
Isopropenyl acetate
108-22-5

Isopropenyl acetate

1-Ethynylcyclohexan-1-ol
78-27-3

1-Ethynylcyclohexan-1-ol

1-acetoxy-1-ethynyl cyclohexane
5240-32-4

1-acetoxy-1-ethynyl cyclohexane

Conditions
Conditions Yield
With Cp*2Sm(THF)2; cyclohexanone oxime acetate; In toluene; at 25 ℃; for 15h;
99%
acetic anhydride
108-24-7

acetic anhydride

1-Ethynylcyclohexan-1-ol
78-27-3

1-Ethynylcyclohexan-1-ol

propargyl bromide
106-96-7

propargyl bromide

1-acetoxy-1-ethynyl cyclohexane
5240-32-4

1-acetoxy-1-ethynyl cyclohexane

Conditions
Conditions Yield
acetic anhydride; 1-Ethynylcyclohexan-1-ol; In dichloromethane; at 0 ℃;
propargyl bromide; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 1.25h;
With water; potassium carbonate; In dichloromethane; for 1.5h;
Acetyl bromide
506-96-7

Acetyl bromide

[[(1-ethynylcyclohexyl)oxy]methyl]-benzene
58348-17-7

[[(1-ethynylcyclohexyl)oxy]methyl]-benzene

1-acetoxy-1-ethynyl cyclohexane
5240-32-4

1-acetoxy-1-ethynyl cyclohexane

Conditions
Conditions Yield
With lithium bromide; In dichloromethane; at 30 - 35 ℃; for 3h; Inert atmosphere;
44%
Bromo-acetic acid 1-ethynyl-cyclohexyl ester
99187-41-4

Bromo-acetic acid 1-ethynyl-cyclohexyl ester

1-oxa-4-methylspiro<4.5>dec-3-en-2-one
4243-31-6

1-oxa-4-methylspiro<4.5>dec-3-en-2-one

1-acetoxy-1-ethynyl cyclohexane
5240-32-4

1-acetoxy-1-ethynyl cyclohexane

4-Methylene-1-oxa-spiro[4.5]decan-2-one
93423-70-2

4-Methylene-1-oxa-spiro[4.5]decan-2-one

7-Bromo-4-methyl-1-oxa-spiro[4.5]dec-3-en-2-one
132994-92-4

7-Bromo-4-methyl-1-oxa-spiro[4.5]dec-3-en-2-one

Conditions
Conditions Yield
With 2,4,6-trimethyl-pyridine; benzophenone; In methanol; isopropyl alcohol; Irradiation;
22%
69%
With 2,4,6-trimethyl-pyridine; benzophenone; In methanol; isopropyl alcohol; Title compound not separated from byproducts; Irradiation;
69%
22%
4 % Chromat.
With 2,4,6-trimethyl-pyridine; benzophenone; In methanol; isopropyl alcohol; Title compound not separated from byproducts; Irradiation;
69%
22%
acetic anhydride
108-24-7

acetic anhydride

1-Ethynylcyclohexan-1-ol
78-27-3

1-Ethynylcyclohexan-1-ol

acetyl chloride
75-36-5

acetyl chloride

1-acetoxy-1-ethynyl cyclohexane
5240-32-4

1-acetoxy-1-ethynyl cyclohexane

Conditions
Conditions Yield
In pyridine; for 1h; Heating;
85.5%
1-acetoxy-1-ethynyl cyclohexane
5240-32-4

1-acetoxy-1-ethynyl cyclohexane

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium amide; diethyl ether / nachfolgend Einleiten von Acetylen unter Druck
With diethyl ether; sodium amide;
Multi-step reaction with 2 steps
1: sodium amide; diethyl ether / nachfolgend Einleiten von Acetylen unter Druck
With diethyl ether; sodium amide;
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere
1.2: 1.5 h / -70 - 20 °C / Inert atmosphere
1.3: 0 °C
2.1: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere
3.1: chloro(triphenylphosphine)gold(I); F5Sb*AgF; water / 1,4-dioxane / 24 h / 20 °C / Inert atmosphere
With dmap; n-butyllithium; chloro(triphenylphosphine)gold(I); F5Sb*AgF; water; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran / 1.5 h / -70 °C / Inert atmosphere
1.2: 1.5 h / -70 - 20 °C / Inert atmosphere
1.3: 0 °C
2.1: methanol; potassium carbonate / 12 h / 20 °C / Inert atmosphere
3.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
With methanol; dmap; n-butyllithium; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / 760.05 Torr
1.2: 1.5 h / -78 °C / 760.05 Torr
2.1: potassium carbonate / methanol / 1 h / 760.05 Torr
3.1: triethylamine / dichloromethane / 0.25 h / 0 °C / 760.05 Torr
3.2: 4 h / 0 - 20 °C / 760.05 Torr
With n-butyllithium; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane;
1-((trimethylsilyl)ethynyl)cyclohexyl acetate
80511-85-9

1-((trimethylsilyl)ethynyl)cyclohexyl acetate

acetic acid 1-acetyl-cyclohexyl ester
52789-73-8

acetic acid 1-acetyl-cyclohexyl ester

1-acetoxy-1-ethynyl cyclohexane
5240-32-4

1-acetoxy-1-ethynyl cyclohexane

Conditions
Conditions Yield
With chloro(triphenylphosphine)gold(I); F5Sb*AgF; water; In 1,4-dioxane; at 20 ℃; for 24h; regioselective reaction; Inert atmosphere;
79 %Spectr.
21 %Spectr.

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