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432-25-7

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432-25-7 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 432-25-7 differently. You can refer to the following data:
1. Colourless Oil
2. 2,6,6-Trimethyl-1,2-cyclohexen-1-carboxaldehyde has a camphoraceous odor for a 50/50 mixture of isomers.

Occurrence

Reported found in tea, apricot, melon, tomato, tomato paste, ginger, rum, Japanese plum, plumcot, mango, apple brandy, calamus, buckwheat, Bourbon vanilla, cape gooseberry and maté.

Uses

beta-Cyclocitral is used as flavoring agent, nutrient, stabilizers, surfactants and emulsifiers.

Definition

ChEBI: A monoterpenoid formally derived from citral by cyclisation. It is a volatile compound produced by a cyanobacteria.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2072, 1947 DOI: 10.1021/ja01200a519Synthesis, p. 781, 1975

Check Digit Verification of cas no

The CAS Registry Mumber 432-25-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,3 and 2 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 432-25:
(5*4)+(4*3)+(3*2)+(2*2)+(1*5)=47
47 % 10 = 7
So 432-25-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h7H,4-6H2,1-3H3

432-25-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • Alfa Aesar

  • (B25700)  beta-Cyclocitral, 90+%   

  • 432-25-7

  • 10g

  • 896.0CNY

  • Detail
  • Alfa Aesar

  • (B25700)  beta-Cyclocitral, 90+%   

  • 432-25-7

  • 50g

  • 2758.0CNY

  • Detail

432-25-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name β-cyclocitral

1.2 Other means of identification

Product number -
Other names 2,6,6-Trimethyl-1-cyclohexene-1-carboxaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:432-25-7 SDS

432-25-7Synthetic route

(E)-β-ionone
79-77-6

(E)-β-ionone

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
Stage #1: (E)-β-ionone With ozone In methanol at -78℃; for 2.5h;
Stage #2: With zinc In water; acetic acid
93%
Stage #1: (E)-β-ionone With oxygen; ozone In methanol at -30℃; for 6h;
Stage #2: With acetic acid; zinc In methanol at -30 - 25℃; for 1.5h; Further stages.;
65%
(i) O3, MeOH, (ii) Zn, AcOH; Multistep reaction;
(E)-3-(2,6,6-Trimethyl-cyclohex-1-enyl)-acrylic acid methyl ester

(E)-3-(2,6,6-Trimethyl-cyclohex-1-enyl)-acrylic acid methyl ester

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
Stage #1: (E)-3-(2,6,6-Trimethyl-cyclohex-1-enyl)-acrylic acid methyl ester With ozone In methanol at -78℃; for 2.5h;
Stage #2: With acetic acid; zinc In water
93%
(8,8-dimethyl-4-methylene)-1-oxaspiro<2.5>octane
54345-56-1

(8,8-dimethyl-4-methylene)-1-oxaspiro<2.5>octane

B

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 3h; Heating;A 7%
B 91%
With toluene-4-sulfonic acid In benzene for 3h; Heating; Yield given. Yields of byproduct given;
oxime 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde
73661-48-0

oxime 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With manganese(IV) oxide In hexane for 0.25h;91%
β-cyclogeraniol
472-20-8

β-cyclogeraniol

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With fluorosulfonyl fluoride; potassium carbonate; dimethyl sulfoxide at 20℃; for 12h; chemoselective reaction;90%
With aluminum isopropoxide at 70 - 100℃; under 12 Torr; anschliessend Erhitzen mit 4-Methoxy-benzaldehyd unter 14 Torr auf 140-160grad;
2,2,6-trimethyl-1-cyclohexenylcarbonitrile
57524-14-8

2,2,6-trimethyl-1-cyclohexenylcarbonitrile

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene; benzene at 0℃; for 2h;90%
With diisobutylaluminium hydride In hexane; benzene for 2h; Ambient temperature;70%
4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one
79-77-6

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
Stage #1: 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one With ozone In methanol at 30 - 40℃; under 4500.45 Torr;
Stage #2: In methanol Product distribution / selectivity; Steam distillation;
80%
β-carotene
161023-01-4

β-carotene

A

2,2,6-trimethylcyclohexan-1-one
2408-37-9

2,2,6-trimethylcyclohexan-1-one

B

(E)-β-ionone
79-77-6

(E)-β-ionone

C

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With oxygen In ethyl acetate at 80℃; Catalytic behavior;A n/a
B 62%
C n/a
2,2-dimethyl-6-methylenecyclohexane-1-carbaldehyde
432-23-5, 4350-73-6

2,2-dimethyl-6-methylenecyclohexane-1-carbaldehyde

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃; Inert atmosphere;60%
5,5-dimethyl-1,4,5,6,7,8-hexahydro-2,3-benzodioxine
433267-90-4

5,5-dimethyl-1,4,5,6,7,8-hexahydro-2,3-benzodioxine

A

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

B

157552-28-8

"iso"-β-cyclocitral

C

4,4-dimethyl-1,3,4,5,6,7-hexahydroisobenzofurane

4,4-dimethyl-1,3,4,5,6,7-hexahydroisobenzofurane

Conditions
ConditionsYield
With triphenylphosphine In cyclohexane for 1h; Heating;A n/a
B n/a
C 15%
ethanol
64-17-5

ethanol

sodium ethanolate
141-52-6

sodium ethanolate

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
unter Kuehlung;
(E/Z)-3,7-dimethyl-2,6-octadienal
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
Reaktion ueber mehrere Stufen;
With aniline
2-cyano-5,9-dimethyl-deca-2,4,8-trienoic acid
1856-67-3

2-cyano-5,9-dimethyl-deca-2,4,8-trienoic acid

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
Reaktion ueber mehrere Stufen;
(+/-)-α-cyclogeraniol
6627-74-3

(+/-)-α-cyclogeraniol

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid; benzene unter Kuehlung;
(+/-)-α-cyclogeranic acid
564-24-9

(+/-)-α-cyclogeranic acid

B

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
Ueberfuehrung in das Diphenylamidin, Reduktion mit Natrium und Alkohol, Behandeln mit verd. Mineralsaeuren;
(+/-)-α-cyclogeranic acid
564-24-9

(+/-)-α-cyclogeranic acid

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
Reaktion ueber mehrere Stufen;
2,6,6-trimethyl-cyclohex-1-enecarboxylic acid
471-90-9

2,6,6-trimethyl-cyclohex-1-enecarboxylic acid

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
Reaktion ueber mehrere Stufen;
Ueberfuehrung in das Diphenylamidin, Reduktion mit Natrium und Alkohol und Behandeln mit Mineralsaeuren;
(1R,6S)-2,2,6-trimethylcyclohexyl carbaldehyde
4350-74-7, 13155-57-2

(1R,6S)-2,2,6-trimethylcyclohexyl carbaldehyde

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With chloroform; bromine; calcium carbonate anschl. mit N,N-Diaethyl-anilin;
hydroxy-(2,6,6-trimethyl-cyclohex-1-enyl)-acetic acid
412035-49-5

hydroxy-(2,6,6-trimethyl-cyclohex-1-enyl)-acetic acid

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With lead(IV) acetate; acetic acid
N-(3,7-dimethyl-octa-2,6-dienylidene)-aniline
72429-03-9

N-(3,7-dimethyl-octa-2,6-dienylidene)-aniline

B

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With diethyl ether; sulfuric acid at -20 - -15℃;
N-(3,7-dimethyl-octa-2,6-dienylidene)-aniline
72429-03-9

N-(3,7-dimethyl-octa-2,6-dienylidene)-aniline

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With sulfuric acid
β-ionone
79636-77-4

β-ionone

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With ozone In methanol; dichloromethane
(8,8-dimethyl-4-methylene)-1-oxaspiro<2.5>octane
54345-56-1

(8,8-dimethyl-4-methylene)-1-oxaspiro<2.5>octane

B

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

C

2,2-dimethyl-6-methylenecyclohexane-1-carbaldehyde
432-23-5, 4350-73-6

2,2-dimethyl-6-methylenecyclohexane-1-carbaldehyde

Conditions
ConditionsYield
With titanium tetrachloride In diethyl ether for 2h; Product distribution; Ambient temperature; various Lewis acids investigated;
beta-carotene
7235-40-7

beta-carotene

A

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

B

trans/cis-15,15'-epoxy-β-carotene

trans/cis-15,15'-epoxy-β-carotene

C

5,6-epoxy-5,6-dihydro-β,β-carotene
1923-89-3

5,6-epoxy-5,6-dihydro-β,β-carotene

Conditions
ConditionsYield
With oxygen In benzene at 30℃; for 24h; Yield given. Further byproducts given. Yields of byproduct given;

A

(+/-)-α-cyclogeranic acid
564-24-9

(+/-)-α-cyclogeranic acid

B

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

C

2,6,6-trimethyl-cyclohex-1-enecarboxylic acid
471-90-9

2,6,6-trimethyl-cyclohex-1-enecarboxylic acid

Conditions
ConditionsYield
With Rexyn 201 (OH form) In methanol Yield given. Yields of byproduct given;
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With potassium hydroxide In methanol for 0.666667h; Ambient temperature;4 g
With potassium hydroxide In methanol at 20℃;
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

B

(E)-β-ionone
79-77-6

(E)-β-ionone

C

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

D

2E,4E-2-methyl-6-oxo-2,4-heptadienal
129454-99-5

2E,4E-2-methyl-6-oxo-2,4-heptadienal

E

4-ethoxyretinoic acid
129454-95-1

4-ethoxyretinoic acid

trans-5,8-epoxy-5,8-dihydroretinoic acid
3012-76-8, 112018-12-9, 129520-10-1, 129520-11-2

trans-5,8-epoxy-5,8-dihydroretinoic acid

Conditions
ConditionsYield
With oxygen In ethanol; water at 85.5℃; under 760 Torr; for 8h; Product distribution; Kinetics; Thermodynamic data; ΔE(excit.); different ratios of O2, solvent, reaction times and temperatures;
4,8,8-trimethyl-1-oxaspiro[2.5]oct-4-ene
72008-24-3

4,8,8-trimethyl-1-oxaspiro[2.5]oct-4-ene

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: 80 percent / MgBr2 / diethyl ether / 0.75 h / Ambient temperature
2: 4 g / KOH / methanol / 0.67 h / Ambient temperature
View Scheme
(2,2-dimethyl-6-methylenecyclohexyl)methanol
472-19-5, 4352-33-4

(2,2-dimethyl-6-methylenecyclohexyl)methanol

A

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

B

2,2-dimethyl-6-methylenecyclohexane-1-carbaldehyde
432-23-5, 4350-73-6

2,2-dimethyl-6-methylenecyclohexane-1-carbaldehyde

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 0.75h; Ambient temperature; Yield given. Yields of byproduct given;
4,8,8-trimethyl-1-oxaspiro[2.5]oct-4-ene
72008-24-3

4,8,8-trimethyl-1-oxaspiro[2.5]oct-4-ene

B

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Conditions
ConditionsYield
With aluminum isopropoxide at 130℃; for 3h; Yield given. Yields of byproduct given;
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

β-cyclogeraniol
472-20-8

β-cyclogeraniol

Conditions
ConditionsYield
Stage #1: 2,6,6-trimethylcyclohex-1-enecarbaldehyde With sodium tetrahydroborate In methanol at 0℃; Inert atmosphere;
Stage #2: With water In methanol
100%
With sodium cyanoborohydride In methanol at -10℃; for 2h;99%
With sodium tetrahydroborate; cerium(III) chloride In methanol at 4℃;97%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

1-(2,2,6-trimethyl-cyclohex-1-enyl)-prop-2-en-1-ol
51768-87-7

1-(2,2,6-trimethyl-cyclohex-1-enyl)-prop-2-en-1-ol

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.0833333h;100%
In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;76%
7-bromoisoquinoline
58794-09-5

7-bromoisoquinoline

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

isoquinolin-7-yl(2,6,6-trimethylcyclohex-1-enyl)methanol

isoquinolin-7-yl(2,6,6-trimethylcyclohex-1-enyl)methanol

Conditions
ConditionsYield
Stage #1: 7-bromoisoquinoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran; hexane at -78 - 20℃;
100%
Stage #1: 7-bromoisoquinoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran; hexane at -78℃; for 1h;
100%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

1-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2-propyn-1-ol
103149-95-7

1-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2-propyn-1-ol

Conditions
ConditionsYield
In tetrahydrofuran at -30 - 20℃; for 1.25h; Inert atmosphere;98%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

oxime 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde
73661-48-0

oxime 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol Reflux;98%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

methyllithium
917-54-4

methyllithium

α,2,6,6-tetramethyl-1-cyclohexene-1-methanol
54345-61-8

α,2,6,6-tetramethyl-1-cyclohexene-1-methanol

Conditions
ConditionsYield
In diethyl ether at -10℃; for 0.5h;97%
95%
bromobenzene
108-86-1

bromobenzene

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

(2,6,6-trimethylcyclohex-1-enyl)phenylmethanol
911850-37-8

(2,6,6-trimethylcyclohex-1-enyl)phenylmethanol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;97%
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran for 0.25h; Inert atmosphere;
Stage #3: With water In tetrahydrofuran
92%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

1-bromo-2,4,5-trimethoxybenzene
20129-11-7

1-bromo-2,4,5-trimethoxybenzene

(2,4,5-trimethoxyphenyl)(2,6,6-trimethylcyclohex-1-enyl)methanol
1148136-45-1

(2,4,5-trimethoxyphenyl)(2,6,6-trimethylcyclohex-1-enyl)methanol

Conditions
ConditionsYield
Stage #1: 1-bromo-2,4,5-trimethoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran for 0.25h; Inert atmosphere;
Stage #3: With water In tetrahydrofuran
97%
3-methyl-but-1-yne
598-23-2

3-methyl-but-1-yne

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

1-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-4-methyl-2-pentyn-1-ol
103149-97-9

1-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-4-methyl-2-pentyn-1-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;96%
1-bromo-3,4-diisopropoxy-5-isopropyl-2-methoxybenzene
883745-86-6

1-bromo-3,4-diisopropoxy-5-isopropyl-2-methoxybenzene

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

(3,4-diisopropoxy-5-isopropyl-2-methoxyphenyl)-(2,6,6-trimethylcyclohex-1-enyl)methanol
883745-87-7

(3,4-diisopropoxy-5-isopropyl-2-methoxyphenyl)-(2,6,6-trimethylcyclohex-1-enyl)methanol

Conditions
ConditionsYield
Stage #1: 1-bromo-3,4-diisopropoxy-5-isopropyl-2-methoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran; hexane at -78 - 0℃;
96%
1-bromo-3-isopropyl-2-methoxy-4,5-methylenedioxybenzene
1148136-34-8

1-bromo-3-isopropyl-2-methoxy-4,5-methylenedioxybenzene

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

(±)-(7-isopropyl-6-methoxybenzo[d][1,3]dioxol-5-yl)(2,6,6-trimethylcyclohex-1-en-1-yl)methanol
1148136-35-9

(±)-(7-isopropyl-6-methoxybenzo[d][1,3]dioxol-5-yl)(2,6,6-trimethylcyclohex-1-en-1-yl)methanol

Conditions
ConditionsYield
Stage #1: 1-bromo-3-isopropyl-2-methoxy-4,5-methylenedioxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran for 0.25h; Inert atmosphere;
Stage #3: With water In tetrahydrofuran
96%
Stage #1: 1-bromo-3-isopropyl-2-methoxy-4,5-methylenedioxybenzene With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran; cyclohexane at -78℃; for 1.08333h; Inert atmosphere; Schlenk technique;
61%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

but-2-enyl ethyl carbonate
121725-70-0

but-2-enyl ethyl carbonate

C14H24O
1293996-62-9

C14H24O

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; tertiary butyl chloride; triphenylphosphine; palladium dichloride In tetrahydrofuran at 20℃; for 16h; Barbier reaction; Inert atmosphere; regioselective reaction;96%
furan
110-00-9

furan

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

(furan-2-yl)(2,6,6-trimethylcyclohex-1-enyl)methanol

(furan-2-yl)(2,6,6-trimethylcyclohex-1-enyl)methanol

Conditions
ConditionsYield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78 - 20℃;95%
para-bromotoluene
106-38-7

para-bromotoluene

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

(2,6,6-trimethylcyclohex-1-enyl)(p-tolyl)methanol
911850-40-3

(2,6,6-trimethylcyclohex-1-enyl)(p-tolyl)methanol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;95%
2-bromoanisole
578-57-4

2-bromoanisole

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

(2-methoxyphenyl)-(2,6,6-trimethyl-cyclohex-1-enyl)-methanol
1148136-37-1

(2-methoxyphenyl)-(2,6,6-trimethyl-cyclohex-1-enyl)-methanol

Conditions
ConditionsYield
Stage #1: 2-bromoanisole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran for 0.25h; Inert atmosphere;
Stage #3: With water In tetrahydrofuran
95%
Stage #1: 2-bromoanisole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran; hexane at -78℃;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane at 0℃;
88%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

(E)-3-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-propensaeure-ethylester
80922-54-9

(E)-3-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2-propensaeure-ethylester

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In 1,4-dioxane at 20℃; for 0.5h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In 1,4-dioxane at 100℃; for 16h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
94%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.25h; Horner-Wadsworth-Emmons Olefination;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran; hexane at 0 - 20℃; Horner-Wadsworth-Emmons Olefination; diastereoselective reaction;
94%
With sodium hydride 1.) dioxane, 30 min, room temp.; 2.) 15h, 100 degC; Yield given. Multistep reaction;
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

allyl bromide
106-95-6

allyl bromide

1-(2,2,6-trimethylcyclohex-1-ene-yl)but-3-en-1-ol
28897-21-4

1-(2,2,6-trimethylcyclohex-1-ene-yl)but-3-en-1-ol

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; chloro-trimethyl-silane; bis(cyclopentadienyl)titanium (III) chloride In tetrahydrofuran at 20℃; for 6h; Barbier type allylation; Inert atmosphere;94%
With ammonium chloride; zinc In tetrahydrofuran; water72%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

1-bromo-2-methoxy-4,5-methylenedioxybenzene
10022-35-2

1-bromo-2-methoxy-4,5-methylenedioxybenzene

(2-methoxy-4,5-methylenedioxyphenyl)-(2,6,6-trimethylcyclohex-1-enyl)methanol
1148136-48-4

(2-methoxy-4,5-methylenedioxyphenyl)-(2,6,6-trimethylcyclohex-1-enyl)methanol

Conditions
ConditionsYield
Stage #1: 1-bromo-2-methoxy-4,5-methylenedioxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran for 0.25h; Inert atmosphere;
Stage #3: With water In tetrahydrofuran
94%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

1-(2,2,6-trimethylcyclohex-1-ene-yl)but-3-en-1-ol
28897-21-4

1-(2,2,6-trimethylcyclohex-1-ene-yl)but-3-en-1-ol

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; chloro-trimethyl-silane; bis(cyclopentadienyl)titanium (III) chloride In tetrahydrofuran at 20℃; for 6h; Barbier type allylation; Inert atmosphere;94%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

methyl-triphenylphosphonium iodide
2065-66-9

methyl-triphenylphosphonium iodide

1,3,3-trimethyl-2-vinylcyclohexene
5293-90-3

1,3,3-trimethyl-2-vinylcyclohexene

Conditions
ConditionsYield
Stage #1: methyl-triphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -50 - 20℃;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran; hexane at -50 - 20℃; for 8h; Wittig Olefination;
94%
Stage #1: methyl-triphenylphosphonium iodide With n-butyllithium In tetrahydrofuran; hexane for 0.5h; Inert atmosphere;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran; hexane for 0.666667h; Inert atmosphere;
71%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

dimethyl 2-methyl-4-acetoxy-2-butenylphosphonate

dimethyl 2-methyl-4-acetoxy-2-butenylphosphonate

3-methyl-5-acetoxy-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene
3917-38-2

3-methyl-5-acetoxy-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at -10 - 0℃; for 2h; Inert atmosphere;93.5%
1-Bromo-2,4-dimethoxybenzene
17715-69-4

1-Bromo-2,4-dimethoxybenzene

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

(2,4-dimethoxyphenyl)(2,6,6-trimethylcyclohex-1-enyl)methanol
1148136-41-7

(2,4-dimethoxyphenyl)(2,6,6-trimethylcyclohex-1-enyl)methanol

Conditions
ConditionsYield
Stage #1: 1-Bromo-2,4-dimethoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 2,6,6-trimethylcyclohex-1-enecarbaldehyde In tetrahydrofuran for 0.25h; Inert atmosphere;
Stage #3: With water In tetrahydrofuran
93%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

C17H21IN2
1191275-65-6

C17H21IN2

Conditions
ConditionsYield
With indium(III) chloride In water at 20℃; for 4 - 6h;93%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

1-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-4,4-dimethyl-2-pentyn-1-ol
103149-98-0

1-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-4,4-dimethyl-2-pentyn-1-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;92.8%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

C25H26O2P(1+)*Br(1-)

C25H26O2P(1+)*Br(1-)

3-methyl-5-acetoxy-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene
3917-38-2

3-methyl-5-acetoxy-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene

Conditions
ConditionsYield
With sodium ethanolate In N,N-dimethyl-formamide at 0 - 5℃; for 2h; Time; Inert atmosphere;92.7%
2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

2-ethynyl-1,3,3-trimethyl-1-cyclohexene
1892-05-3

2-ethynyl-1,3,3-trimethyl-1-cyclohexene

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 6h; Colvin Alkyne Synthesis;92%
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h;89%
With lithium diisopropyl amide In tetrahydrofuran at -78 - 25℃; Condensation;74%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

2-(4'-aminophenyl)ethyl alcohol
104-10-9

2-(4'-aminophenyl)ethyl alcohol

C19H26N2O
1191275-69-0

C19H26N2O

Conditions
ConditionsYield
With indium(III) chloride In water at 20℃; for 4 - 6h;92%
tryptamine
61-54-1

tryptamine

2,6,6-trimethylcyclohex-1-enecarbaldehyde
432-25-7

2,6,6-trimethylcyclohex-1-enecarbaldehyde

C20H26N2
1612226-09-1

C20H26N2

Conditions
ConditionsYield
With choline chloride–urea at 80℃; for 2h; Pictet-Spengler Synthesis; Green chemistry;92%

432-25-7Relevant articles and documents

Synthesis of chlorins and bacteriochlorins from cycloaddition reactions with porphyrins

Cavaleiro, José A. S.,Monteiro, Carlos J. P.,Moura, Nuno M. M.,P. M. S. Neves, M. Gra?a,Tomé, Augusto C.

, (2022/02/10)

Chlorins and bacteriochlorins are reduced porphyrin-type derivatives displaying characteristic structural, physical, and chemical features. Such features make chlorins and bacteriochlorins key “players” in several fields, and specifically in medicine as p

An unexpected generation of magnetically separable Se/Fe3O4 for catalytic degradation of polyene contaminants with molecular oxygen

Chen, Xingyu,Mao, Jingfei,Liu, Chuang,Chen, Chao,Cao, Hongen,Yu, Lei

supporting information, p. 3205 - 3208 (2020/08/12)

Selenization of Fe2O3 with NaHSe led to Se/Fe3O4. The unexpected generation of Fe3O4 attributed to the reduction conditions of the reaction, and the resulted magnetic features of the materi

Kinetics of β-Carotene Oxidation in the Presence of Highly Active Forms of μ-Carbido Diiron(IV) Tetraphenylporphyrinate

Simonova,Zaitseva,Tyulyaeva, E. Yu.,Zdanovich,Koifman

, p. 2128 - 2134 (2018/10/24)

Abstract: The oxidative destruction of β-carotene in the presence of highly oxidized forms of μ-carbido-bis[(5,10,15,20-tetraphenyl-21H,23H-porphyrinato)iron(IV)] (1 → 3) or its analog with axially coordinated imidazole (2 → 4) obtained under the action of tert-butyl hydroperoxide tBuOOH was studied by spectrophotometry. It was found that compound 3 is the oxo form of compound 1 singly oxidized at the macrocyclic ligand (π radical cation) under the action of which β-carotene is oxidized with a rate constant k = 3.3 L2 mol–2 s–1. A?conclusion is drawn that short-lived compound 4 has unique EAS and is capable of oxidizing tBuOOH to form O2, which makes it possible to consider it the model of peroxidase. The value of k for the reaction with the participation of β-carotene and compound 4 (k = 10.3 L2 mol–2 s–1) is three times higher than that with the participation of compound 3. If a new portion of β-carotene is added, the process of its oxidative destruction in the presence of compounds 3 or 4 occurs without additives of the dimeric complex and peroxide. A?possible nature of compound 4 is discussed, as well as the influence of N-base in the coordination sphere of the complex on the nature of active intermediates and the rate of β-carotene decomposition.

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