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100-50-5 Usage

Chemical Properties

slightly yellowish-green liquid

Uses

Cyclohex-3-ene-1-carbaldehyde can be used as coupled exposure to ingredients of cosmetic products.

Synthesis Reference(s)

Journal of the American Chemical Society, 92, p. 3126, 1970 DOI: 10.1021/ja00713a034The Journal of Organic Chemistry, 52, p. 5293, 1987 DOI: 10.1021/jo00232a049

General Description

A colorless liquid. Flash point 135°F. Less dense than water and slightly soluble in water. Hence floats on water. Irritates skin, eyes and mucous membranes. Used to make fabrics water resistant, and to make other chemicals.

Air & Water Reactions

Flammable. Slightly soluble in water.

Reactivity Profile

3-Cyclohexene-1-carboxaldehyde is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Flammable

Safety Profile

Moderately toxic by ingestion, inhalation, and sh contact. Corrosive. An eye, skin, and mucous membrane irritant. Flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

Check Digit Verification of cas no

The CAS Registry Mumber 100-50-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 100-50:
(5*1)+(4*0)+(3*0)+(2*5)+(1*0)=15
15 % 10 = 5
So 100-50-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H10O/c8-6-7-4-2-1-3-5-7/h1-2,6-7H,3-5H2/t7-/m0/s1

100-50-5 Well-known Company Product Price

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  • Alfa Aesar

  • (L04894)  3-Cyclohexene-1-carboxaldehyde, 98%   

  • 100-50-5

  • 50ml

  • 771.0CNY

  • Detail

100-50-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Cyclohexene-1-carboxaldehyde

1.2 Other means of identification

Product number -
Other names 3-cyclohexene carboxaldehyde

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:100-50-5 SDS

100-50-5Synthetic route

buta-1,3-diene
106-99-0

buta-1,3-diene

acrolein
107-02-8

acrolein

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With erbium(III) triflate at 20℃; for 2h; Diels-Alder reaction; Ionic liquid; regioselective reaction;99%
In 1,4 dimethylcyclohexane at 150℃; under 30003 Torr; for 3h; Solvent; Temperature; Inert atmosphere; Autoclave;90%
K10-Fe(III) In dichloromethane at 20℃; for 6h;83%
2-(3-cyclohexenyl)-1,3-dithiane
53178-49-7

2-(3-cyclohexenyl)-1,3-dithiane

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With silica gel; copper(II) nitrate In tetrachloromethane for 0.416667h; Ambient temperature;97%
With p-benzoquinone; sodium iodide In water; acetonitrile at 100℃; for 72h;74 %Chromat.
cyclohex-3-enylmethanol
72581-32-9, 1679-51-2

cyclohex-3-enylmethanol

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With titanium(IV) oxide; oxygen at 29.84℃; under 760.051 Torr; for 24h; Sealed tube; Irradiation;96%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; periodic acid In dichloromethane at 20℃; for 2h;78%
With tetrabutylammomium bromide; dihydrogen peroxide; [Ru3O(OAc)6(MeOH)3](1+)*AcO(1-) In dichloromethane at 20℃; for 24h;45%
In dichloromethane
2-Cyclohex-3-enyl-[1,3]dithiolane

2-Cyclohex-3-enyl-[1,3]dithiolane

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With silica gel; copper(II) nitrate In tetrachloromethane for 1h; Ambient temperature;96%
3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With LaNi5 hydride In tetrahydrofuran; methanol for 8h; Mechanism; Ambient temperature; other alkynes, alkenes, aldehydes, ketones; other rare earth alloys; var. reaction time and temp.;91%
4-(chloromethyl)cyclohex-1-ene
2555-08-0

4-(chloromethyl)cyclohex-1-ene

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With 4Na(1+)*6H(1+)*NiMo6O24(10-)=Na4H6NiMo6O24; oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 12h; Irradiation;87%
2-Allyl-hex-5-enal
151259-43-7

2-Allyl-hex-5-enal

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
Cl2(PCy3)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC6H5 In benzene at 20℃; for 1h;82%
norborn-2-ene
498-66-8

norborn-2-ene

cis-7-iodobicyclo[2.2.1]heptan-exo-2-ol

cis-7-iodobicyclo[2.2.1]heptan-exo-2-ol

B

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With hypoiodous acid; acetone at -40 - 20℃;A 72%
B n/a
vinyl-2 dihydro-2,3 4H-pyranne
3236-44-0

vinyl-2 dihydro-2,3 4H-pyranne

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With diethylaluminium chloride; triphenylphosphine In dichloromethane at 25℃; for 1h;61%
With diethylaluminium chloride; triphenylphosphine In dichloromethane at 25℃; for 1h;61%
In hexane at 410℃;
norborn-2-ene
498-66-8

norborn-2-ene

A

Norbornan-2-on
497-38-1

Norbornan-2-on

B

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

C

exo-2,3-epoxynorbornane
278-74-0, 3146-39-2, 57378-36-6

exo-2,3-epoxynorbornane

D

exo-2,3-epoxynorbornane
844874-18-6

exo-2,3-epoxynorbornane

Conditions
ConditionsYield
With iodosylbenzene; TFTEP*FeCl In dichloromethane at 0℃; Yields of byproduct given;A 3.9%
B 0.3%
C n/a
D n/a
With iodosylbenzene; OEP*FeCl In dichloromethane at 0℃; Yield given. Yields of byproduct given;A 1.6%
B 0.2%
C n/a
D n/a
With iodosylbenzene; TFTEP*MnCl In dichloromethane at 0℃; Yield given. Yields of byproduct given;A 0.8%
B 0.2%
C n/a
D n/a
buta-1,3-diene
106-99-0

buta-1,3-diene

A

acrolein
107-02-8

acrolein

B

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With oxygen; bis(ethylene)rhodium acetylacetonate In toluene at 80℃; under 37503 Torr; for 1h;A 1%
B 0.3%
With oxygen; bis(ethylene)rhodium acetylacetonate In toluene at 80℃; under 37503 Torr; for 1h;A 1%
B 0.3%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

cyclohex-3-enyl magnesium (1+); bromide

cyclohex-3-enyl magnesium (1+); bromide

toluene
108-88-3

toluene

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
beim kurzen Kochen des Reaktionsprodukts mit verd. Schwefelsaeure;
Cyclohex-3-enylmethylnitrit
50552-13-1

Cyclohex-3-enylmethylnitrit

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
In benzene for 10h; Irradiation;
norborn-2-ene
498-66-8

norborn-2-ene

A

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

B

exo-2,3-epoxynorbornane
278-74-0, 3146-39-2, 57378-36-6

exo-2,3-epoxynorbornane

C

exo-2,3-epoxynorbornane
844874-18-6

exo-2,3-epoxynorbornane

Conditions
ConditionsYield
With iodosylbenzene; Mn(III)(SAP)NCS In acetonitrile Product distribution; other alkenes, var. additives (surfactants), var. pyridine concentrations;
With iodosylbenzene; Mn(T4PyP)OAc In acetonitrile at 30℃; var. olefins; other catalyst;
norborn-2-ene
498-66-8

norborn-2-ene

A

Norbornan-2-on
497-38-1

Norbornan-2-on

B

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

C

exo-2,3-epoxynorbornane
844874-18-6

exo-2,3-epoxynorbornane

Conditions
ConditionsYield
With pyrimido<5.4-g>pteridine 10-oxide In acetonitrile Product distribution; Mechanism; Ambient temperature; Irradiation;A 4 % Chromat.
B n/a
C 42 % Chromat.
Bicyclo<3.1.1>hept-2-en-exo-6-ol
111292-74-1

Bicyclo<3.1.1>hept-2-en-exo-6-ol

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With sodium hydroxide
carbon monoxide
201230-82-2

carbon monoxide

cyclohexa-1,4-diene
1165952-92-0

cyclohexa-1,4-diene

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With rhodium (triphenylphosphine)acetylacetonatecarbonyl; hydrogen; triphenylphosphine at 80℃; under 7600 Torr; for 3h;71 % Spectr.
With hydrogen; rhodium 1.) from -196 deg C to RT, 2.) toluene, 50 deg C, 48 h, 70 atm; Yield given. Multistep reaction;
carbon monoxide
201230-82-2

carbon monoxide

cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

A

1-cyclohexene-1-carboxaldehyde
1192-88-7

1-cyclohexene-1-carboxaldehyde

B

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With triphenyl phosphite; acetylacetonatobis(triphenylphosphite)rhodium; hydrogen at 80℃; under 7600 Torr; for 3h; Title compound not separated from byproducts;A 31 % Spectr.
B 42 % Spectr.
With rhodium (triphenylphosphine)acetylacetonatecarbonyl; hydrogen; triphenylphosphine at 80℃; under 7600 Torr; for 3h; Title compound not separated from byproducts;A 43 % Spectr.
B 30 % Spectr.
bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With acetic acid at 250℃;
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

magnesium compound of 4-bromo-cyclohexene-(1)

magnesium compound of 4-bromo-cyclohexene-(1)

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With toluene Behandeln des Reaktionsproduktes mit verd. Schwefelsaeure;
carbon monoxide
201230-82-2

carbon monoxide

cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

A

1,4-cyclohexanedicarboxaldehyde
33424-83-8

1,4-cyclohexanedicarboxaldehyde

B

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

C

cis/trans-1,3-cyclohexanedicarboxaldehyde
55309-54-1

cis/trans-1,3-cyclohexanedicarboxaldehyde

D

cyclohex-2-enecarbaldehyde
42540-33-0

cyclohex-2-enecarbaldehyde

Conditions
ConditionsYield
With Rh4(CO)14; hydrogen In hexane at 19.85℃; Product distribution; Hydroformylation; reaction was studied by in-situ high-pressure IR spectroscopy;
Copper(I) trifluoromethanethiolate
3872-23-9

Copper(I) trifluoromethanethiolate

exo-2,3-epoxynorbornane
844874-18-6

exo-2,3-epoxynorbornane

A

Norbornan-2-on
497-38-1

Norbornan-2-on

B

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

3-(trifluoromethylthio)-2-norbornanol

3-(trifluoromethylthio)-2-norbornanol

Conditions
ConditionsYield
In toluene at 100 - 110℃; Title compound not separated from byproducts;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
Stage #1: 4-ethenylcyclohexene With cis-[Ru(2,9-Me2phen)2(OH2)2](PF6)2 In acetonitrile at 55℃; for 0.5h;
Stage #2: With dihydrogen peroxide In acetonitrile for 8h;
cyclohex-3-enylmethanol
72581-32-9, 1679-51-2

cyclohex-3-enylmethanol

A

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

B

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With peracetic acid; dihydrogen peroxide; palladium on activated charcoal In dichloromethane; water at 59.84℃; for 1h;
With peracetic acid; dihydrogen peroxide; Mn(III)AlPO-5 In dichloromethane; water at 89.84℃; for 1h;
cyclohex-3-enylmethanol
72581-32-9, 1679-51-2

cyclohex-3-enylmethanol

A

3,4-epoxycyclohexane-1-carboxaldehyde

3,4-epoxycyclohexane-1-carboxaldehyde

B

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With peracetic acid; dihydrogen peroxide; palladium on activated charcoal In water; acetonitrile at 59.84℃; for 1h;
acrolein dimer
100-73-2

acrolein dimer

A

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

B

P2O5

P2O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) NaH, DMSO / 1) 25 deg C, 15 min., DMSO; 2) 25 deg C, 1 h
2: 61 percent / Et2AlCl, PPh3 / CH2Cl2 / 1 h / 25 °C
View Scheme
cyclohex-3-enylmethanol
72581-32-9, 1679-51-2

cyclohex-3-enylmethanol

A

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

B

RCu(CN)ZnI, (table I. entry 11)

RCu(CN)ZnI, (table I. entry 11)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaNO2, H2SO4 / H2O / -10 °C
2: benzene / 10 h / Irradiation
View Scheme
ethyl-3-cyclohexene-1-carboxylate
15111-56-5

ethyl-3-cyclohexene-1-carboxylate

A

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

B

RCu(CN)ZnI, (table I. entry 11)

RCu(CN)ZnI, (table I. entry 11)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LiAlH4 / diethyl ether / Heating
2: NaNO2, H2SO4 / H2O / -10 °C
3: benzene / 10 h / Irradiation
View Scheme
benzylamine
100-46-9

benzylamine

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Benzyl-cyclohex-3-en-(E)-ylidenemethyl-amine

Benzyl-cyclohex-3-en-(E)-ylidenemethyl-amine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 2h; Heating;100%
3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

1,2,5,6-tetrahydrobenzoic acid
4771-80-6

1,2,5,6-tetrahydrobenzoic acid

Conditions
ConditionsYield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃;96%
3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

cyclohex-3-enylmethanol
72581-32-9, 1679-51-2

cyclohex-3-enylmethanol

Conditions
ConditionsYield
Stage #1: 3-Cyclohexene-1-carboxaldehyde With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;
Stage #2: With sodium hydroxide In water at 0℃; for 12h; Inert atmosphere;
99%
With 1-Methylpyrrolidine; C13H12MnN3O5; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 24h; Autoclave; Glovebox;98%
With dmap; formic acid; hexarhodium hexadecacarbonyl; carbon monoxide In tetrahydrofuran at 30℃; under 3800 Torr; for 5h;93%
3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

3-cyclohexene-1-carboxylic acid 3-cyclohexen-1-ylmethyl ester
2611-00-9

3-cyclohexene-1-carboxylic acid 3-cyclohexen-1-ylmethyl ester

Conditions
ConditionsYield
With trimethylaluminum; isopropyl alcohol; 2,7-dimethyl-1,8-biphenylenediol In hexane; toluene at 21℃; for 0.25h; Tishchenko reaction;99%
With (2,7-dimethyl-1,8-biphenylenedioxy)-bis(diisopropoxyaluminum) In toluene at 21℃; for 0.25h; Dimerization; Tishchenko reaction;98%
i-PrOAl 1,1'-biphenyl-2-oxy-2'-perfluorooctanesulfonamide In toluene at 20℃; for 0.5h; Tishchenko reaction;95%
N-allyl-N-phenylamine
589-09-3

N-allyl-N-phenylamine

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

N-<(1-allyl-3-cyclohexenyl)methylene>aniline
100747-84-0

N-<(1-allyl-3-cyclohexenyl)methylene>aniline

Conditions
ConditionsYield
With Pd(PPh3); trifluoroacetic acid In benzene at 80℃; for 20h;99%
3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

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

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

C13H23BO3

C13H23BO3

Conditions
ConditionsYield
With FeBr2*2THF; C30H46N4Si2(2+) In acetonitrile at 20℃; for 12h; Glovebox; Inert atmosphere; Sealed tube;99%
With C14H24N4Si(1+)*I(1-) In benzene-d6 at 24℃; for 0.166667h; Catalytic behavior; Inert atmosphere; Schlenk technique; regioselective reaction;86%
With [((2,6-(i-Pr)2C6H3)NC(=CH2)CH=C(Me)N(2,6-(i-Pr)2C6H3))Ge] In benzene-d6 at 60℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; chemoselective reaction;98 %Spectr.
With C18H21La In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
With tris(η5-methylcyclopentadienyl)lanthanum(III) In tetrahydrofuran at 20℃; for 0.166667h; Catalytic behavior; Schlenk technique; Glovebox; Inert atmosphere; chemoselective reaction;99 %Spectr.
phenyl selenocyanate
2179-79-5

phenyl selenocyanate

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

(1R,4R,5R)-4-Phenylselanyl-6-oxa-bicyclo[3.2.1]octane-7-carbonitrile

(1R,4R,5R)-4-Phenylselanyl-6-oxa-bicyclo[3.2.1]octane-7-carbonitrile

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane for 0.166667h; Ambient temperature;98%
benzylamine
100-46-9

benzylamine

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

(E)-N-(cyclohex-3-en-1-ylmethylene)-1-phenylmethanamine

(E)-N-(cyclohex-3-en-1-ylmethylene)-1-phenylmethanamine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane for 0.5h; Ambient temperature;98%
In toluene at 110 - 115℃; Dean-Stark;
methyldiphenylsilane
776-76-1

methyldiphenylsilane

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

(cyclohex-3-enylmethoxy)-methyl-diphenyl-silane

(cyclohex-3-enylmethoxy)-methyl-diphenyl-silane

Conditions
ConditionsYield
With (triphenylphosphine)copper(I) hydride hexamer In toluene at 20℃; for 2h;98%
3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

3-cyclohexene-1-carbonitrile
100-45-8

3-cyclohexene-1-carbonitrile

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid In acetonitrile for 16h; Reflux;97%
With ammonium acetate; acetic acid; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate at 70℃; for 12h; Inert atmosphere;94%
Stage #1: 3-Cyclohexene-1-carboxaldehyde With hydroxylamine hydrochloride; triethylamine In acetonitrile at 80℃;
Stage #2: With phthalic anhydride In acetonitrile at 25 - 80℃; for 18h;
64%
Multi-step reaction with 2 steps
1: 94 percent / hydroxylamine hydrochloride, sodium acetate / H2O / 2 h / 45 °C
2: 77 percent / acetic acid anhydride / 1 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: acetylhydroxamic acid; boron trifluoride diethyl etherate / methanol / Reflux
2: bismuth(lll) trifluoromethanesulfonate / acetonitrile / 8 h / Reflux
View Scheme
3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

A

toluene
108-88-3

toluene

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
With palladium/alumina; hydrogen In hexane at 325℃; Flow reactor; Green chemistry;A 3.6%
B 96.4%
With hydrogen In hexane at 325℃; Flow reactor; Green chemistry;A 83.4%
B 16.4%
In octane at 300℃; for 1h; Reagent/catalyst; Temperature;A 82%
B 10%
In octane at 200℃; for 1h;A 25%
B 44%
ethylene glycol
107-21-1

ethylene glycol

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

2-(3-cyclohexenyl)-1,3-dioxolane
28193-08-0

2-(3-cyclohexenyl)-1,3-dioxolane

Conditions
ConditionsYield
With Envirocat EPZ10 supported reagent for 0.0333333h; microwave irradiation;96%
With KU-2 cation exchanger H(1+) In toluene at 130℃;87%
With ammonium chloride; benzene
With ammonium chloride; benzene
allyl bromide
106-95-6

allyl bromide

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

α-(2-propenyl)-3-cyclohexen-1-methanol
91055-81-1

α-(2-propenyl)-3-cyclohexen-1-methanol

Conditions
ConditionsYield
With tin; hydrogen bromide In diethyl ether; water Ambient temperature;96%
With manganese; cyclopentadienyl titanium(IV) trichloride; trimethylsilyl bromide; triethylamine hydrobromide In tetrahydrofuran Inert atmosphere;90%
(i) Mg, (ii) /BRN= 774001/; Multistep reaction;
With magnesium In diethyl ether
Malonic acid monomethyl ester
16695-14-0

Malonic acid monomethyl ester

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

(propene-2 oate de methyle) yl-4 cyclohexene trans
124939-60-2

(propene-2 oate de methyle) yl-4 cyclohexene trans

Conditions
ConditionsYield
With piperidine In pyridine RT, overnight, reflux, 2 h;96%
3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

1,2-di(cyclohex-3-en-1-yl)ethane-1,2-diol

1,2-di(cyclohex-3-en-1-yl)ethane-1,2-diol

Conditions
ConditionsYield
With chloro-trimethyl-silane; zinc; bis(cyclopentadienyl)vanadium dichloride In tetrahydrofuran at 20℃; for 13h; Reduction;96%
With samarium; trimethylsilyl bromide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;64%
tert-butyldiphenylsilane
33729-92-9

tert-butyldiphenylsilane

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

4-(((tert-butyldiphenylsilyl)oxy)methyl)cyclohexene

4-(((tert-butyldiphenylsilyl)oxy)methyl)cyclohexene

Conditions
ConditionsYield
With (triphenylphosphine)copper(I) hydride hexamer In toluene at 40℃; for 6h;96%
2-bromoprop-1-ene
557-93-7

2-bromoprop-1-ene

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

4-(1'-hydroxy-2'-methylprop-2-enyl)cyclohexene
139021-69-5

4-(1'-hydroxy-2'-methylprop-2-enyl)cyclohexene

Conditions
ConditionsYield
Stage #1: 2-bromoprop-1-ene With lithium In diethyl ether at -30 - 20℃; for 1.75h; Inert atmosphere;
Stage #2: 3-Cyclohexene-1-carboxaldehyde In diethyl ether at -30 - 20℃; for 1.75h; Inert atmosphere;
Stage #3: With water; ammonium chloride In diethyl ether Cooling with ice;
96%
1-methylindole
603-76-9

1-methylindole

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

3-(3-cyclohexen-1-ylmethyl)-1-methyl-1H-indole

3-(3-cyclohexen-1-ylmethyl)-1-methyl-1H-indole

Conditions
ConditionsYield
With indium(III) tris[bis(trifluoromethanesulfonyl)amide]; methyldiphenylsilane In 1,4-dioxane at 50℃; for 24h; Inert atmosphere; Schlenk technique;96%
cyclopentanone
120-92-3

cyclopentanone

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

2,5-bis(1,2,5,6-tetra-hydro-benzylidene)-cyclopentanone

2,5-bis(1,2,5,6-tetra-hydro-benzylidene)-cyclopentanone

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 25℃; for 3h;96%
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

1,2,5,6-tetrahydrobenzaldehyde diethyl acetal
6314-88-1

1,2,5,6-tetrahydrobenzaldehyde diethyl acetal

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol Heating;95%
With Amberlyst 15 at 4℃; for 1h;93%
With ethanol; ammonium chloride
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

cyclohex-3-enyl(trimethylsilyloxy)acetonitrile
85906-00-9

cyclohex-3-enyl(trimethylsilyloxy)acetonitrile

Conditions
ConditionsYield
niobium pentafluoride at 20℃; for 0.166667h;95%
With N-methyl-2-indolinone In dichloromethane at 20℃; for 0.166667h;90%
With zinc(II) iodide
methyl cyanoformate
17640-15-2

methyl cyanoformate

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

1-cyano-1-(4'-cyclohexenyl)-1-(methoxycarbonyloxy)methane

1-cyano-1-(4'-cyclohexenyl)-1-(methoxycarbonyloxy)methane

Conditions
ConditionsYield
With diisopropylamine In tetrahydrofuran Addition;95%
Dimethylphenylsilane
766-77-8

Dimethylphenylsilane

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

(cyclohex-3-enylmethoxy)-dimethyl-phenyl-silane

(cyclohex-3-enylmethoxy)-dimethyl-phenyl-silane

Conditions
ConditionsYield
With (triphenylphosphine)copper(I) hydride hexamer In toluene at 20℃; for 2h;95%
malononitrile
109-77-3

malononitrile

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

recorcinol
108-46-3

recorcinol

2-amino-4-(cyclohex-3-enyl)-7-hydroxy-4H-chromene-3-carbonitrile

2-amino-4-(cyclohex-3-enyl)-7-hydroxy-4H-chromene-3-carbonitrile

Conditions
ConditionsYield
Stage #1: malononitrile; 3-Cyclohexene-1-carboxaldehyde With morpholine In ethanol for 0.25h;
Stage #2: recorcinol In ethanol at 20℃; for 72h;
95%
4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
1539-32-8

4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester

buta-1,3-diene
106-99-0

buta-1,3-diene

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

C14H24O

C14H24O

Conditions
ConditionsYield
With chromium dichloride; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In tetrahydrofuran at 20℃; for 24h; Irradiation; diastereoselective reaction;95%
3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In water at 45℃; for 2h;94%
With hydroxylamine hydrochloride; sodium acetate In methanol Ambient temperature;92%
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water for 3h; Ambient temperature;90%

100-50-5Relevant articles and documents

SELECTIVE HYDROFORMYLATION OF CYCLODIENES TO CYCLOALKENECARBOXALDEHYDES USING CATALYSTS DERIVED DIRECTLY FROM Rh VAPOUR AND CYCLODIENES

Salvadori, Piero,Vitulli, Giovanni,Raffaelli, Andrea,Lazzaroni, Raffaello

, p. 351 - 356 (1983)

Cocondensation of Rh atoms with cyclodienes at liquid nitrogen temperature yields Rh complexes, thermally stable in excess of the ligand, which are good catalysts for the selective hydroformylation of cyclodienes to cycloalkenecarboxaldehydes.

Visible-Light-Driven Photocatalytic Oxidation of Organic Chlorides Using Air and an Inorganic-Ligand Supported Nickel-Catalyst Without Photosensitizers

Yu, Han,Wang, Jingjing,Zhai, Yongyan,Zhang, Mengqi,Ru, Shi,Han, Sheng,Wei, Yongge

, p. 4274 - 4279 (2018)

Engineering photoredox-triggered chemical transformation via visible light has been an emerging area in organic synthesis. However, most of the well-established photocatalysts are based upon either transition metal complexes involved with noble metals and organic ligands or photosensitive organic dyes, the development of pure inorganic molecular photocatalysts that could provide better stability and durability is greatly retarded. Herein we discover that the Anderson polyoxometalate (POM) Na4[NiMo6O18(OH)6] (1), which consists of pure inorganic framework built from a central NiII core supported by six MoVIO6 inorganic scaffold/ligands, can be used as a powerful photocatalyst. Upon irradiation with visible light (>400 nm), the compound can catalyze, in high efficiency, a wide range of reactions, including the oxidative cross-coupling reaction of chlorides with amines, as well as oxidation of chlorides using molecular oxygen, affording various imines, aldehydes, and ketones, respectively in high selectivity and good yields. Owing to the robust inorganic framework, this catalyst exhibits excellent stability during the catalysis and reusability with little loss of the catalytic activity, thus providing an alternative without use of complicated organic ligands and expensive noble metal-based photosensitizers.

Studies on Transition-Metal Oxo and Nitrido Complexes. Part 10. New Oxo-Ruthenium and Oxo-Osmium Pyridine Complexes, and Use of the Former as Catalysts for Oxidation of Alcohols

El-Hendawy, Ahmed M.,Griffith, William P.,Taha, Fatma I.,Moussa, Mahmoud N.

, p. 901 - 906 (1989)

The new complexes trans-(2+), trans-(2+), trans- (M=Ru or Os; X=Cl or Br; py= pyridine) and trans- are reported.Both tans-(2+) and trans- in CH2Cl2 are efficient oxidants for primary alcohols to aldehydes and secondary alcohols to ketones, and function catalytically, with N-methylmorpholine N-oxide (mmo) or n4> as co-oxidants.A simple preparation of trans- and the isolation of , , and OsO2L2(O2C6H10)> (L=pyridine N-oxide) are also reported. Complexes were characterised by Raman, i.r. and (1)H n.m.r.spectroscopy.

Rhodium-Catalyzed C,C-Double Bond Cleavage by Molecular Oxygen

Boennemann, Helmut,Nunez, Washington,Rohe, Dieter M. M.

, p. 177 - 185 (1983)

Acetylacetonatorhodiumolefin systems, allylrhodium complexes, or (Ph3P)3RhCl catalyzed the conversion of alkenes and molecular oxygen to carbonyl compounds via C=C-bond cleavage.For example, 2,3-dimethyl-2-butene was transformed into acetone.Butadiene and isoprene also undergo oxidative C=C-bond cleavage to form acrylaldehyde and related compounds.

Alkene Epoxidations Catalyzed by Iron(III), Manganese(III), and Chromium(III) Porphyrins. Effects of Metal and Porphyrin Substituents on Selectivity and Regiochemistry of Epoxidation

Traylor, Teddy G.,Miksztal, Andrew R.

, p. 7443 - 7448 (1989)

The products of epoxidation of norbornene, cyclohexene, and adamantylideneadamantane with pentafluoroiodobenzene using as catalysts variously substituted tetraphenylporphyrin complexes of chloroiron(III), chloromanganese(III), and chlorochromium(III) have been determined.All catalysts afforded the epoxide from adamantylideneadamantane, suggesting that the metallacycle intermediate, impossible in this case, is not required for epoxidation.The ratios of exo- to endo-epoxynorbornanes obtained from norbornene varied from about 1E3 for electropositively substituted Cr(III) complexes gradually through the Mn(III) and Fe(III) series to a value of about 6 for electronegatively substituted iron(III) porphyrins.Mechanisms ranging from limiting electrophilic addition to limiting electron transfer are proposed to account for these changes.The electronegatively substituted iron porphyrins show a greater tendency toward epoxidation rather than allylic oxidation and show more selectivity for cis-alkenes.

Selective catalytic oxidation of alcohols using hydrogen peroxide

Wynne,Lloyd,Witsil,Mushrush,Stalick

, p. 588 - 592 (2000)

-

-

Garin

, p. 4071 (1969)

-

Reduction of Organic Compounds with Rare-Earth Intermetallics Containing Absorbed Hydrogen

Imamoto, Tsuneo,Mita, Takeshi,Yokoyama, Masataka

, p. 5695 - 5699 (1987)

The hydrogenation of organic compounds with rare-earth intermetallic hydrides has been investigated.Alkynes,alkenes,aldehydes,ketones,nitriles,imines, and nitro compounds are hydrogenated in excellent yields with LaNi5H6 or LaNi4.5Al0.5H5 at 0-60 deg C.The present hydrogenation method has the following characteristic features. (1) The intermetallic compounds (alloys) are not poisoned by compounds containing an amino group or a halogen atom. (2) The alloys can be used repeatedly without decrease in activity. (3) The reaction conditions are mild, and selective hydrogenations of some organic functional groups can be achieved.The reaction mechanism of this hydrogenation is briefly discussed in terms of stereochemistry and H/D exchange reactions.

Rhodium complex catalyzed hydroformylation reactions of linear and cyclic mono- and diolefins

Trzeciak, Anna M.,Ziolkowski, Jozef J.

, p. 213 - 216 (1994)

The hydroformylation reactions of cyclopentene, cyclohexene, 4-vinylcyclohexene, cycloheptene and cyclooctene, catalyzed with a Rh(acac)2/P(OPh)3 (I) system at 80 deg C and 10 atm (CO+H2), have been studied.Only cyclopentene and 4-vinylcyclohexene undergo hydroformylation at 1 atm and 40 deg C.The hydroformylation of some cyclic dienes; (1,3- and 1,4-cyclohexadienes, 1,3- and 1,5-cyclooctadienes and 1,3-cyclopentadiene), at 10 atm and 80 deg C, was investigated in two catalytic systems: (I) and Rh(acac) (CO) (PPh3) / PPh3 (II).The main reaction products of cyclohexadienes and pentadiene (at 80 deg C, 10 atm) are unsaturated monoaldehydes.In hydroformylation of 1,5-cyclooctadiene the main product is formylcyclooctane.Key words: Rhodium; Olefins; Hydroformylation

The Cycloaddition of the 1,3-Butadiene Radical Cation with Acrolein and Methyl Vinyl Ketone

Castle, Lyle W.,Gross, M. L.

, p. 637 - 646 (1989)

The 1,3-butadiene radical cation reacts with acrolein and methyl vinyl ketone to produce 'stable' adducts.The nature of the reaction and the structures of the adducts were investigated by collisional activation decomposition (CAD) combined with tandem mas

-

Werstink,Kadai

, p. 3350,3357 (1972)

-

A high-performance selective oxidation system for the facile production of fine chemicals

Raja, Robert,Thomas, John Meurig,Greenhill-Hooper, Mike,Doukova, Violeta

, p. 1924 - 1926 (2007)

MnIIIAlPO-5 and CrVIAlPO-5 redox (microporous) catalysts are effective, in the presence of dissolved acetylperoxyborate (APB) under mild conditions (333-373 K), and much superior to the titanosilicate, TS-1 (also a single-site heterogeneous catalyst), in the selective oxidation of primary, secondary, benzylic and other unsaturated alcohols, p-cymene, methyl cyclohexene and other speciality organics which are of value in the fine-chemical and pharmaceutical industries. The Royal Society of Chemistry.

Cyclohexyldimethanol synthetic method, catalyst and use thereof (by machine translation)

-

Paragraph 0059-0061; 0065-0067, (2018/05/16)

The present invention provides a method for synthesis of cyclohexane dimethanol, comprises the following steps: under the action of catalyst, cyclohexene formaldehyde by the hydroformylation reaction and hydrogenation reaction to make said cyclohexyldimet

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