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591-49-1

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591-49-1 Usage

Chemical Properties

colourless liquid

Physical properties

Clear, colorless, very flammable, watery liquid with a characteristically unpleasant, aromatic hydrocarbon-type odor.

Uses

1-Methyl-1-cyclohexene (2,3,4,5-Tetrahydrotoluene) was used to study the secondary organic aerosol (SOA) yields from the ozonolysis of cycloalkenes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 917, 1980 DOI: 10.1021/jo01293a030

General Description

1-Methyl-1-cyclohexene (2,3,4,5-Tetrahydrotoluene) is a sterically hindered, unactivated alkene.

Environmental fate

Photolytic. Atkinson (1985) reported a rate constant of 9.45 x 10-11 cm3/molecule?sec for the reaction of 1-methylcyclohexene with OH radicals in the atmosphere.

Purification Methods

Free it from hydroperoxides by passing through a column containing basic alumina or refluxing with cupric stearate, filter and fractionally distil it from sodium. [Vogel J Chem Soc 1332 1938, Cope et al. J Am Chem Soc 79 4729 1957, Beilstein 5 III 197, 5 VI 245.]

Check Digit Verification of cas no

The CAS Registry Mumber 591-49-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 1 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 591-49:
(5*5)+(4*9)+(3*1)+(2*4)+(1*9)=81
81 % 10 = 1
So 591-49-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H12/c1-7-5-3-2-4-6-7/h5H,2-4,6H2,1H3

591-49-1 Well-known Company Product Price

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  • Alfa Aesar

  • (L15014)  1-Methyl-1-cyclohexene, 96%   

  • 591-49-1

  • 5g

  • 188.0CNY

  • Detail
  • Alfa Aesar

  • (L15014)  1-Methyl-1-cyclohexene, 96%   

  • 591-49-1

  • 25g

  • 701.0CNY

  • Detail

591-49-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-METHYL-1-CYCLOHEXENE

1.2 Other means of identification

Product number -
Other names 1-Methylcyclohexene-1

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:591-49-1 SDS

591-49-1Synthetic route

methylenecyclohexane
1192-37-6

methylenecyclohexane

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

Conditions
ConditionsYield
In water Ambient temperature;99%
With Grotjahn’s catalyst In [(2)H6]acetone at 70℃; for 1h; Reagent/catalyst; Inert atmosphere; Glovebox;98%
With (μ-Cl)2Ni2(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)2 In dichloromethane at 20℃; for 3h;79%
cis-methyl-2 phenylacetoxy cyclohexane
42288-78-8, 42288-79-9

cis-methyl-2 phenylacetoxy cyclohexane

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

3-methyl-1-cyclohexene
591-48-0

3-methyl-1-cyclohexene

C

carbon dioxide
124-38-9

carbon dioxide

D

methyl cyclohexane
82166-21-0

methyl cyclohexane

Conditions
ConditionsYield
In pentane Irradiation; Further byproducts given;A 1.4%
B 13%
C 97%
D 6.7%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

cyclohexanone
108-94-1

cyclohexanone

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

Conditions
ConditionsYield
Stage #1: methyl magnesium iodide; cyclohexanone In diethyl ether
Stage #2: With iodine In toluene Heating;
95%
Yield given. Multistep reaction;
2) dehydration; Yield given. Multistep reaction;
methylmagnesium chloride
676-58-4

methylmagnesium chloride

cyclohexanone
108-94-1

cyclohexanone

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

Conditions
ConditionsYield
Stage #1: methylmagnesium chloride; cyclohexanone In tetrahydrofuran at -10 - 0℃; for 0.5h; Inert atmosphere;
Stage #2: With toluene-4-sulfonic acid In 1,2-dichloro-ethane Reflux;
92%
1-Methylcyclohexanol
590-67-0

1-Methylcyclohexanol

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

Conditions
ConditionsYield
With phosphoric acid at 110 - 120℃;91%
With aluminum(III) sulfate; iodine
With aluminum(III) sulfate; toluene-4-sulfonic acid
1-Methylcyclohexanol
590-67-0

1-Methylcyclohexanol

acetic anhydride
108-24-7

acetic anhydride

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

1-acetoxy-1-methyl-cyclohexane
16737-30-7

1-acetoxy-1-methyl-cyclohexane

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In acetonitrile at -20℃; for 5h;A 9%
B 91%
1-Methylcyclohexanol
590-67-0

1-Methylcyclohexanol

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

1-acetoxy-1-methyl-cyclohexane
16737-30-7

1-acetoxy-1-methyl-cyclohexane

Conditions
ConditionsYield
With acetic anhydride; scandium tris(trifluoromethanesulfonate) In acetonitrile at -20℃; for 5h;A 9%
B 91%
methylenecyclohexane
1192-37-6

methylenecyclohexane

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

methyl cyclohexane
82166-21-0

methyl cyclohexane

Conditions
ConditionsYield
With ammonium hypophosphorous acid; palladium on activated charcoal In benzene for 3h;A n/a
B 87%
2-methyl-1,7-octadiene
13151-07-0

2-methyl-1,7-octadiene

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

Conditions
ConditionsYield
With trans-dichlorobis(2,6-dibromphenoxy)oxotungsten(VI); tetraethyllead(IV) In various solvent(s) at 90℃; for 2h;84%
1-(N,N-Dichloroamino)-1-methylcyclohexane
57337-77-6

1-(N,N-Dichloroamino)-1-methylcyclohexane

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

methylenecyclohexane
1192-37-6

methylenecyclohexane

Conditions
ConditionsYield
In neat (no solvent) at 210℃; Product distribution; var. reactor materials;A 80%
B 20%
all-cis-1,3-bis(methansulfonyloxy)-2-methylcyclohexan

all-cis-1,3-bis(methansulfonyloxy)-2-methylcyclohexan

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

Conditions
ConditionsYield
With tetra-n-propylammonium bromide In N,N-dimethyl-formamide electrochemical reduction (Pt-electrode);73%
1,2-epoxy-1-methylcyclohexane
1713-33-3

1,2-epoxy-1-methylcyclohexane

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II); diethylzinc In tetrahydrofuran; hexane Inert atmosphere;72%
With trifluoroacetic acid; selenobenzamide In dichloromethane at 0℃; for 0.0833333h; Mechanism; With other reagents are dicussed.;51 % Chromat.
With trifluoroacetic acid; selenobenzamide In dichloromethane at 0℃; for 0.0833333h; With other reagents are discussed.;51 % Chromat.
3-methylcyclohex-2-en-1-ol
21378-21-2

3-methylcyclohex-2-en-1-ol

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

Conditions
ConditionsYield
With methanol; toluene-4-sulfonic acid at 25℃; for 18h; Inert atmosphere; Sealed tube; UV-irradiation;71%
2,5-dihydrotoluene
4313-57-9

2,5-dihydrotoluene

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

3-methyl-1-cyclohexene
591-48-0

3-methyl-1-cyclohexene

C

4-methylcyclohexene
591-47-9

4-methylcyclohexene

D

methyl cyclohexane
82166-21-0

methyl cyclohexane

Conditions
ConditionsYield
With hydrogen; bis(acetylacetonate)nickel(II); triphenylphosphine In toluene at 40℃; for 8h; Yields of byproduct given;A 67%
B n/a
C n/a
D 2%
With hydrogen; bis(acetylacetonate)nickel(II); triphenylphosphine In toluene at 40℃; under 760 Torr; for 8h; Product distribution; Mechanism; different 1,4-cyclohexadienes and reaction times;A 67%
B n/a
C n/a
D 2%
toluene
108-88-3

toluene

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

2,5-dihydrotoluene
4313-57-9

2,5-dihydrotoluene

C

3-methyl-1-cyclohexene
591-48-0

3-methyl-1-cyclohexene

Conditions
ConditionsYield
With lithium; ethylenediamine; isopropyl alcohol at 85 - 95℃; for 0.333333h;A n/a
B 67%
C n/a
4-methyl-1,2-diazaspiro<2.5>oct-1-ene
14359-89-8

4-methyl-1,2-diazaspiro<2.5>oct-1-ene

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

3-methyl-1-cyclohexene
591-48-0

3-methyl-1-cyclohexene

Conditions
ConditionsYield
With β‐cyclodextrin for 2h; Irradiation;A 66%
B 34 % Chromat.
With alpha cyclodextrin for 2h; Irradiation;A 72 % Chromat.
B 28 % Chromat.
1-Methylcyclohexanol
590-67-0

1-Methylcyclohexanol

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

1-acetoxy-1-methyl-cyclohexane
16737-30-7

1-acetoxy-1-methyl-cyclohexane

C

1'-methylcyclohexyl 3-oxobutanoate
91328-33-5

1'-methylcyclohexyl 3-oxobutanoate

D

dimethylglyoxal
431-03-8

dimethylglyoxal

Conditions
ConditionsYield
With acetic anhydride; cobalt(II) chloride In acetonitrile at 80℃; for 12h;A 10%
B 65%
C 19%
D n/a
1-Methylcyclohexanol
590-67-0

1-Methylcyclohexanol

acetic anhydride
108-24-7

acetic anhydride

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

1-acetoxy-1-methyl-cyclohexane
16737-30-7

1-acetoxy-1-methyl-cyclohexane

C

1'-methylcyclohexyl 3-oxobutanoate
91328-33-5

1'-methylcyclohexyl 3-oxobutanoate

D

dimethylglyoxal
431-03-8

dimethylglyoxal

Conditions
ConditionsYield
With cobalt(II) chloride In acetonitrile at 80℃; for 12h;A 10%
B 65%
C 19%
D n/a
4-methyl-N'-(2-methylcyclohexylidene)benzenesulfonohydrazide
52826-41-2

4-methyl-N'-(2-methylcyclohexylidene)benzenesulfonohydrazide

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

Conditions
ConditionsYield
With tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃;54%
With tetrabutylammonium perchlorate; oxygen In dimethyl sulfoxide for 12h; Ambient temperature; electrolysis;46.6%
carbon monoxide
201230-82-2

carbon monoxide

2-methyl-1-cyclohexenyl triflate
32363-21-6

2-methyl-1-cyclohexenyl triflate

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

2-methylcyclohex-1-ene-1-carbaldehyde
54625-15-9

2-methylcyclohex-1-ene-1-carbaldehyde

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; lithium chloride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃;A 8 % Chromat.
B 53%
1-chloroacetophenone
532-27-4

1-chloroacetophenone

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

4a-methyl-1,2,3,4,4a,9,10,10aβ-octahydro-9-phenanthrone
60795-74-6, 60795-83-7, 84711-03-5, 84711-04-6, 134930-34-0

4a-methyl-1,2,3,4,4a,9,10,10aβ-octahydro-9-phenanthrone

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In acetonitrile for 1h; Irradiation;A n/a
B 45%
1-methoxy-5-methyl-cyclohexa-1,4-diene
13697-84-2

1-methoxy-5-methyl-cyclohexa-1,4-diene

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

3-methyl-1-cyclohexene
591-48-0

3-methyl-1-cyclohexene

C

1-methoxy-5-methyl-bicyclo<3.1.0>hexane
88739-07-5

1-methoxy-5-methyl-bicyclo<3.1.0>hexane

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc In diethyl ether at -35℃;A n/a
B n/a
C 40%
With hydrogenchloride; amalgamated zinc In diethyl ether at -35℃;
cis-trans-1,3-bis(methansulfonyloxy)-2-methylcyclohexan

cis-trans-1,3-bis(methansulfonyloxy)-2-methylcyclohexan

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

endo-6-Methylbicyclo<3.1.0>hexan
90271-67-3

endo-6-Methylbicyclo<3.1.0>hexan

Conditions
ConditionsYield
With tetra-n-propylammonium bromide In N,N-dimethyl-formamide electrochemical reduction (Pt-electrode);A 40%
B 9%
bicyclo[4.1.0]heptane
286-08-8

bicyclo[4.1.0]heptane

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

3-methyl-1-cyclohexene
591-48-0

3-methyl-1-cyclohexene

C

Cycloheptene
628-92-2

Cycloheptene

Conditions
ConditionsYield
With iodine In dichloromethane for 8h; Irradiation;A 7%
B 39%
C 0.2%
With iodine In dichloromethane for 8h; Product distribution; Quantum yield; Irradiation; different reaction circumstances;
4-methyl-cyclohex-3-enecarbaldehyde
7560-64-7

4-methyl-cyclohex-3-enecarbaldehyde

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

para-xylene
106-42-3

para-xylene

C

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

D

toluene
108-88-3

toluene

Conditions
ConditionsYield
With palladium on carbon at 300℃; under 760.051 Torr; Inert atmosphere;A n/a
B n/a
C 22%
D 27%
1-methyl-4,5-threo-bis(benzenesulphonyl)cyclohexene

1-methyl-4,5-threo-bis(benzenesulphonyl)cyclohexene

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

Conditions
ConditionsYield
With ammonia; lithium23%
methanol
67-56-1

methanol

2-methyl-1-iodo-1-cyclohexene
40648-08-6

2-methyl-1-iodo-1-cyclohexene

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

1-chloro-2-methylcyclohexene
16642-49-2

1-chloro-2-methylcyclohexene

Conditions
ConditionsYield
at 40℃; for 10h; Irradiation;A 12%
B 21%
C7H12Pt(Cl)4
108296-73-7

C7H12Pt(Cl)4

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

3-methyl-1-cyclohexene
591-48-0

3-methyl-1-cyclohexene

C

Cycloheptene
628-92-2

Cycloheptene

D

4-methylcyclohexene
591-47-9

4-methylcyclohexene

E

methylenecyclohexane
1192-37-6

methylenecyclohexane

Conditions
ConditionsYield
With potassium cyanide In diethyl ether Refluxing in ether for 1 h, evapn. of ether in vac., treating of residue with aq. KCN.; Extg. with CHCl3, NMR, MS. Further products.;A 13.6%
B 10%
C 2.8%
D 4.3%
E 9.8%
cis-methyl-2 phenylacetoxy cyclohexane
42288-78-8, 42288-79-9

cis-methyl-2 phenylacetoxy cyclohexane

A

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

B

3-methyl-1-cyclohexene
591-48-0

3-methyl-1-cyclohexene

C

methyl cyclohexane
82166-21-0

methyl cyclohexane

D

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

Conditions
ConditionsYield
In pentane Irradiation; Further byproducts given;A 1.4%
B 13%
C 6.7%
D 2.7%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

1,2-epoxy-1-methylcyclohexane
1713-33-3

1,2-epoxy-1-methylcyclohexane

Conditions
ConditionsYield
With tris(1,4-dihydro-2-methyl-4-oxo-1-(2-phenylethyl)-3-pyridinolato)iron(III); oxygen; isobutyraldehyde In 1,2-dichloro-ethane at 60℃; for 22h;100%
With tert.-butylhydroperoxide; C14H25Cl2MoO6P In 2,2,4-trimethylpentane; dichloromethane at 19.9℃; for 24h;100%
With sodium persulfate; water at 20℃; for 12h; Reagent/catalyst;100%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

methyl cyclohexane
82166-21-0

methyl cyclohexane

Conditions
ConditionsYield
With hydrogen In neat (no solvent) at 70℃; for 5h; Catalytic behavior; Flow reactor;100%
With C40H56N2RuSi4; hydrogen In toluene at 25℃; under 760.051 Torr; for 3h; Schlenk technique;99%
With C40H56FeN2Si4(2-); hydrogen In 1,2-dimethoxyethane at 80℃; under 7600.51 Torr; for 2h; Schlenk technique; Autoclave;99%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

propionaldehyde
123-38-6

propionaldehyde

(methyl-2' cyclohexyl)-1 propanone-1
85995-78-4

(methyl-2' cyclohexyl)-1 propanone-1

Conditions
ConditionsYield
With dibenzoyl peroxide at 90℃; for 10h;100%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

propargyl alcohol
107-19-7

propargyl alcohol

2-Bromo-1-methyl-1-prop-2-ynyloxy-cyclohexane
118616-30-1

2-Bromo-1-methyl-1-prop-2-ynyloxy-cyclohexane

Conditions
ConditionsYield
With N-Bromosuccinimide at 0℃; for 1h;100%
triethylsilane
617-86-7

triethylsilane

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

triethyl(cis-2-methylcyclohexyl)silane

triethyl(cis-2-methylcyclohexyl)silane

Conditions
ConditionsYield
With C14H26B22Cl22Zn at 20℃; for 0.25h; Inert atmosphere; Glovebox;100%
With fluorotris(pentafluorophenyl)phosphonium tetrakis(pentafluorophenyl)borate In dichloromethane at 20℃; for 1h; Inert atmosphere;96%
With C33H36F5N2Zn(1+)*C24BF20(1-) In dichloromethane-d2 at 20℃; for 14h;
With C29H42AlN2(1+)*C24BF20(1-) In chlorobenzene at 20℃; for 0.166667h;82 %Spectr.
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

1-bromo-1-methylcyclohexane
931-77-1

1-bromo-1-methylcyclohexane

Conditions
ConditionsYield
With (R)-2,6-di([1,1'-biphenyl]-4-yl)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine-4-oxide; boron tribromide In dichloromethane-d2 at 20℃; for 1h;99%
With hydrogen bromide In water at 45℃; for 48h;68.7%
With hydrogen bromide; acetic acid; diphenylamine
With hydrogen bromide; acetic acid
With hydrogen bromide; silica gel In water at 0 - 20℃; for 48h; Reagent/catalyst;98 %Spectr.
ammonia borane complex
10043-11-5

ammonia borane complex

1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

aminodi-2-methylcyclohexylborane

aminodi-2-methylcyclohexylborane

Conditions
ConditionsYield
In tetrahydrofuran Reflux; Inert atmosphere;97%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

2-methoxy-1,4-benzoquinone
2880-58-2

2-methoxy-1,4-benzoquinone

3-Methoxy-5a-methyl-5a,6,7,8-tetrahydro-dibenzofuran-2-ol
137123-26-3

3-Methoxy-5a-methyl-5a,6,7,8-tetrahydro-dibenzofuran-2-ol

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane 1.) -78 deg C, 1 h, 2.) -78 deg C to r.t., 12 h;96.6%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

6-oxoheptanoic acid
3128-07-2

6-oxoheptanoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; 12-tungstophosphoric acid/Al/C In tert-butyl alcohol at 60℃; for 24h;96%
With tris(cetylpyridinium) 12-tungstophosphate; dihydrogen peroxide In tert-butyl alcohol for 24h; Heating;90%
With tert.-butylhydroperoxide; indium(III) chloride In water at 90℃; for 8.2h;84%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

[Chloro-(3,4-dichloro-phenylsulfanyl)-methyl]-trimethyl-silane
114124-63-9

[Chloro-(3,4-dichloro-phenylsulfanyl)-methyl]-trimethyl-silane

1,2-Dichloro-4-[2-methyl-cyclohex-(E)-ylidenemethylsulfanyl]-benzene

1,2-Dichloro-4-[2-methyl-cyclohex-(E)-ylidenemethylsulfanyl]-benzene

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at -20℃; for 0.5h;96%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

1-(2-methyl-2-cyclohexen-1-yl)octan-1-one

1-(2-methyl-2-cyclohexen-1-yl)octan-1-one

Conditions
ConditionsYield
With 2,6-Dibromopyridine; aluminum (III) chloride In dichloromethane at 20℃; for 3h; Inert atmosphere;96%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

1,2-dibromo-1-methylcyclohexane
56860-91-4

1,2-dibromo-1-methylcyclohexane

Conditions
ConditionsYield
With bromine In dichloromethane at 0 - 20℃; for 0.5h;95%
With chloroform; bromine
With 4DABCO*6HBr*4Br2 In chloroform for 0.5h;95 % Chromat.
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

acetic anhydride
108-24-7

acetic anhydride

1-(2-methyl-cyclohex-2-enyl)-ethanone
15564-32-6

1-(2-methyl-cyclohex-2-enyl)-ethanone

Conditions
ConditionsYield
With hydrogenchloride; silver hexafluoroantimonate In acetic acid for 12h; Ambient temperature;95%
ethylaluminum dichloride In dichloromethane at 25℃; for 1h;55%
With tin(IV) chloride
With zinc(II) chloride
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

N-(4-methylphenylaminothio)phthalimide
118622-94-9

N-(4-methylphenylaminothio)phthalimide

N-(4-methylphenyl)-2-methylenecyclohexane-1-sulfenamide

N-(4-methylphenyl)-2-methylenecyclohexane-1-sulfenamide

Conditions
ConditionsYield
With triethylamine In acetone at 20℃;95%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

cis-2-acetoxy-1-methylcyclohexanol

cis-2-acetoxy-1-methylcyclohexanol

Conditions
ConditionsYield
With water; iodine In acetic acid at 90℃; for 2.5h;95%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

(1RS,2SR)-2-bromo-1-fluoro-1-methylcyclohexene
122540-68-5, 130721-14-1, 141038-94-0

(1RS,2SR)-2-bromo-1-fluoro-1-methylcyclohexene

Conditions
ConditionsYield
With N-Bromosuccinimide; 1-ethyl-3-methylimidazolium oligo hydrogenfluoride In dichloromethane at 20℃; for 1h;95%
With N-Bromosuccinimide; 3-ethyl-1-methyl-imidazorium oligo hydrogen fluoride In dichloromethane at 20℃; for 1h;95%
With N-Bromosuccinimide; 3-ethyl-1-methylimidazolium oligo hydrogen fluoride In dichloromethane at 20℃; for 1h;95%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

p-methylphenacyl chloride
4209-24-9

p-methylphenacyl chloride

4a,6-Dimethyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one
145474-36-8

4a,6-Dimethyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In benzene for 1h; Irradiation;95%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate

4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate

2-methylene-1-[4-acetamido(2,2,6,6-tetramethylpiperidin-1-yl)oxy]cyclohexane

2-methylene-1-[4-acetamido(2,2,6,6-tetramethylpiperidin-1-yl)oxy]cyclohexane

Conditions
ConditionsYield
Stage #1: 1-methylcyclohex-1-ene; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In acetonitrile at 20℃; for 1.5h;
Stage #2: With sodium carbonate
95%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

trans-2-bromo-1-methylcyclohexanol

trans-2-bromo-1-methylcyclohexanol

Conditions
ConditionsYield
With water In acetone at 20℃; for 0.0833333h;95%
1-methylcyclohex-1-ene
591-49-1

1-methylcyclohex-1-ene

1,2-dichloro-1-methylcyclohexane
69954-99-0

1,2-dichloro-1-methylcyclohexane

Conditions
ConditionsYield
With manganese(IV) oxide; acetyl chloride; manganese(ll) chloride In N,N-dimethyl-formamide at 30℃; for 2h;94%
With ; calcium chloride In acetic acid Heating;74%
With diethyl ether; chlorine
With molybdenum(V) chloride In dichloromethane at -78℃;
With 1-nitrocyclohexene; titanium tetrachloride In dichloromethane at 25℃; for 0.5h;21 % Chromat.

591-49-1Relevant articles and documents

Role of hydrogenolysis and nucleophilic substitution in hydrodenitrogenation over sulfided NiMo/γ-Al2O3

Prins,Rota

, p. 195 - 199 (2001)

The HDS of cyclohexanethiol and 2-methylcyclohexanethiol was studied over a sulfided NiMO/γ-Al2O3 catalyst. About 66% of the thiols reacted by elimination to (methyl)cyclohexene and 33% by hydrogenolysis of the C-S bond to (methyl)cyclohexane. These values were slightly lower than those for the selectivity to methylcyclohexene and slightly higher than those for the selectivity to methylcyclohexane in the HDN of 2-methylcyclohexylamine. HDN occurred predominantly in aliphatic molecules that contained H atoms in the β position relative to the nitrogen atom by elimination of ammonia. Part of the remaining HDN occurred by nucleophilic substitution of the amine by H2S, followed by elimination of H2S from the resulting thiol and, to a lesser extent, by C-S bond hydrogenolysis, the rest of the remaining HDN occurred by direct hydrogenolysis of the C-N bond.

Influence of noble metals (Pd, Pt) on the performance of Ru/Al2O3 based catalysts for toluene hydrogenation in liquid phase

Suppino, Raphael Soeiro,Landers, Richard,Cobo, Antonio José Gomez

, p. 41 - 49 (2016)

Catalytic hydrogenation of aromatic compounds is of great interest due to environmental aspects and the wide range of industrial processes involving such reaction. In this context, the present work aims to study the influence of Pd or Pt addition on the performance of Ru/Al2O3 based catalysts for toluene hydrogenation in liquid phase. For this, catalysts were prepared by wet impregnation from chlorinated precursors and reduced in liquid phase by formaldehyde (H2CO). After impregnation, a part of the catalysts were activated ex situ at 573?K or in situ at 523?K under H2. The studied solids were characterized by N2 physisorption, SEM?+?EDX, TEM, XPS and TPR techniques. Catalytic tests were conducted in a slurry Parr reactor at 373?K under constant H2 pressure of 5?MPa. Results show that solids reduction by H2CO led to metallic species, while the activation treatments form oxides and decrease the catalytic activity. The initial reaction rate of non-activated monometallic catalysts follows the order: Ru/Al2O3???Pd/Al2O3?≈?Pt/Al2O3. A synergistic effect on the activity of Ru/Al2O3 based catalysts is induced by the Pt addition.

Kinetic investigation of the effect of nickel and fluorine on the HDN of methylcyclohexylamine over WS2/Al2O3 catalysts

Sun, Mingyong,Prins, Roel

, p. 138 - 144 (2001)

The effects of incorporation of nickel and fluorine in WS2/Al2O3 catalysts on the kinetics of the hydrodenitrogenation of methylcyclohexylamine were investigated. The catalysts were prepared from ammonium tetrathiotungstat

Electrocatalytic hydrogenation of toluene using a proton exchange membrane reactor: Influence of catalyst materials on product selectivity

Fukazawa, Atsushi,Takano, Ken,Matsumura, Yoshimasa,Nagasawa, Kensaku,Mitsushima, Shigenori,Atobe, Mahito

, p. 897 - 899 (2018)

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Method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins

-

Paragraph 0054-0066, (2021/02/06)

The invention discloses a method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins, wherein the method comprises the steps: carrying out hydrocarbylation reaction on the non-terminal olefins and sulfoxide in the presence of ferric salt and hydrogen peroxide, carrying out one-pot reaction on disubstituted non-terminal olefins to generate the trisubstituted olefins, and carrying out one-pot reaction on the trisubstituted non-terminal olefins to generate the tetrasubstituted olefins. In the method, sulfoxide is simultaneously used as a hydrocarbylation reagent and a solvent of olefins, and one more hydrocarbyl substituent is added to a reaction product compared with a double-bond carbon atom of a reactant, so that an olefin carbon chain isincreased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.

Influence of Intracrystalline Ionic Strength in MFI Zeolites on Aqueous Phase Dehydration of Methylcyclohexanols

Milakovi?, Lara,Hintermeier, Peter H.,Liu, Yue,Baráth, Eszter,Lercher, Johannes A.

supporting information, p. 24806 - 24810 (2021/09/08)

The impact of the concentration of hydrated hydronium ions and in turn of the local ionic strength in MFI zeolites has been investigated for the aqueous phase dehydration of 4-methylcyclohexanol (E1 mechanism) and cis-2-methylcyclohexanol (E2 mechanism). The E2 pathway with the latter alcohol led to a 2.5-fold higher activity. The catalytic activity normalized to the hydronium ions (turnover frequency, TOF) passed through a pronounced maximum, which is attributed to the increasing excess chemical potential of the alcohols in the pores, increasing in parallel with the ionic strength and the additional work caused by repulsive interactions and charge separation induced by the bulky alcohols. While the maximum in rate observed is invariant with the mechanism or substitution, the reaction pathway is influencing the activation parameters differently.

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