2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde supplier

Name
2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde
EINECS 207-454-0
CAS No. 472-66-2
Article Data15
CAS DataBase
Density 0.879 g/cm³
Solubility
Melting Point
Formula C₁₁H₁₈O
Boiling Point 243.3 °C at 760 mmHg
Molecular Weight 166.263
Flash Point 76.8 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms (2,6,6-Trimethyl-1-cyclohexenyl)acetaldehyde;2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde;2-(2,6,6-Trimethylcyclohex-1-enyl)acetaldehyde;b-Apo-8-carotenal;b-Cyclohomocitral;b-Homocyclocitral;
PSA 17.07000
LogP 3.10200

Synthetic route

: 86558-54-5, 86558-55-6
2-((E)-2-Methoxy-vinyl)-1,3,3-trimethyl-cyclohexene

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
With perchloric acid In tetrahydrofuran for 0.5h; Ambient temperature;	94%

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

: 2032-35-1
Bromoacetaldehyde diethyl acetal

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
Stage #1: Bromoacetaldehyde diethyl acetal With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 3.25h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In tetrahydrofuran at 10 - 15℃; for 3h;	93.7%

: 4360-63-8
2-bromomethyl-1,3-dioxolane

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

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
Stage #1: 2-bromomethyl-1,3-dioxolane With iodine; magnesium In 2-methyltetrahydrofuran at 30 - 40℃; for 3.25h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In 2-methyltetrahydrofuran at 10 - 15℃; for 3h;	93.1%

: 7252-83-7
1-bromo-2,2-dimethoxyethane

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

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
Stage #1: 1-bromo-2,2-dimethoxyethane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 3.25h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In tetrahydrofuran at 10 - 15℃; for 3h; Temperature; Solvent;	92.8%

: 97-97-2
chloroacetaldehyde dimethyl acetal

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

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
Stage #1: chloroacetaldehyde dimethyl acetal With iodine; magnesium In ethylene dibromide at 30 - 45℃; for 3.41667h; Inert atmosphere; Stage #2: 2,2,6-trimethylcyclohexan-1-one In ethylene dibromide at 10 - 15℃; for 3h;	90.7%

: 1-((E)-2-Methoxy-vinyl)-6,6-dimethyl-cyclohexene

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
With perchloric acid In diethyl ether for 5h;	78.9%

: 128463-60-5
α--2,6,6,-trimethyl-1-cyclohexenemethanol

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
With formic acid for 0.166667h; Ambient temperature;	75%

: 408511-80-8
1-ethoxyethynyl-2,2,6-trimethyl-cyclohexanol

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
With quinoline; Petroleum ether bei partieller Hydrierung an bleihaltigem Palladium, anschl. mit wss. H2SO4;

: 87570-49-8, 100678-90-8
2-acetoxyvinylidene-1,1,3-trimethyl-cyclohexane

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
With hydrogenchloride; water

: 41613-59-6
1-ethynyl-2,2,6-trimethyl-1-cyclohexanol

: 75-08-1
ethanethiol

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
In tetrachloromethane (i) AIBN, (irradiation), (ii) CF3CO2H; Multistep reaction;

: 41613-59-6
1-ethynyl-2,2,6-trimethyl-1-cyclohexanol

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
With vanadium tri-n-propoxide; benzoic acid; triphenylhydroxysilane In various solvent(s) at 140 - 150℃;	81 % Turnov.

: 41613-59-6
1-ethynyl-2,2,6-trimethyl-1-cyclohexanol

A: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

B: 100513-69-7
α-(2,6,6-Trimethyl-1-cyclohexenyl)acetaldehyd

Conditions

Conditions	Yield
tetrabutoxytitanium; p-Toluic acid; copper(l) chloride In 1,2-dichloro-benzene at 130℃; for 4h; Title compound not separated from byproducts;

: 14393-45-4
(E)-3-(2,6,6-trimethylcyclohex-1-enyl)acrylic acid

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
With hydrogenchloride; diphenyl phosphoryl azide; triethylamine 1) dioxan, RT, 1 h, 2.) reflux, 15 min; Yield given. Multistep reaction;

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

: 1216963-74-4
lithium acetylide-ethylenediamine complex

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
(i), (ii) Ph3SiOH, (iii) (Ph3SiO)3VO; Multistep reaction;

1-acetoxy-2-<2,6,6-trimethyl-cyclohex-1-enyl>-ethene: 1-acetoxy-2-<2,6,6-trimethyl-cyclohex-1-enyl>-ethene

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
With methanol; water; sodium hydrogencarbonate

1-ethoxy-2-<2,6,6-trimethyl-cyclohex-1-enyl>-ethene: 1-ethoxy-2-<2,6,6-trimethyl-cyclohex-1-enyl>-ethene

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
With ethanol; water; toluene-4-sulfonic acid

: 79-77-6
(E)-β-ionone

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / NaOH, Br2 / H2O; dioxane / 4 h / Ambient temperature 2: 1.) Et3N, diphenyl phosphoryl azide, 2.) 0.5 N aq. HCl / 1) dioxan, RT, 1 h, 2.) reflux, 15 min View Scheme

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

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: s-BuLi / 1.) THF, hexane, from -70 deg C to -25 deg C, 2.) -25 deg C, 0.5 h 2: 75 percent / 90percent aq. formic acid / 0.17 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 61 percent / tetrahydrofuran / 1 h / Ambient temperature 2: 94 percent / 60percent perchloric acid / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

: 87570-48-7
acetic acid-(1-ethynyl-2,2,6-trimethyl-cyclohexyl ester)

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc oxide; silicon oil / 200 °C / Erhitzen unter vermindertem Druck 2: HCl; water View Scheme

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 149-73-5
trimethyl orthoformate

: 86558-53-4
Dimethoxy-2',2' ethyl-2 trimethyl-1,3,3 cyclohexene-1

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 24h; Ambient temperature;	100%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: C11H19NO

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol; water Reflux;	100%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 269057-55-8
2,2-dideutero-2-(2,6,6-trimethylcyclohex-1-en-1-yl)ethanal

Conditions

Conditions	Yield
With water-d2; sodium hydride In pyridine at 25℃; for 4h; deuteration;	99.9%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 57576-15-5
(2,6,6-trimethylcyclohex-1-enyl)acetonitrile

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide at 100℃;	97%
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; sodium acetate / methanol; water / Reflux 2: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / tetrahydrofuran; ethyl acetate / 20 °C / Inert atmosphere View Scheme

: 123-75-1
pyrrolidine

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 93178-30-4
1-<2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl>pyrrolidine

Conditions

Conditions	Yield
In toluene at 60℃; for 1h;	96%
In toluene at 60℃; for 1h;	88%

: 401-78-5
3-bromo-1-trifluoromethylbenzene

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 1441167-69-6
1-(3-(trifluoromethyl)phenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol

Conditions

Conditions	Yield
Stage #1: 3-bromo-1-trifluoromethylbenzene With iodine; magnesium In tetrahydrofuran for 0.0833333h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In tetrahydrofuran at -78 - 20℃; for 2h;	90%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 472-65-1
2,4,4-trimethyl-3-(2'-hydroxymethyl)-2-cyclohexene

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;	85%
With lithium aluminium tetrahydride In diethyl ether Heating;
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In diethyl ether
With sodium tetrahydroborate In methanol Inert atmosphere;

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 18162-48-6
tert-butyldimethylsilyl chloride

: tert-butyl-dimethyl-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-vinyloxy]-silane

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran	85%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: C13H13NOS2

: (1R,4S,7R,8S,11S)-11-methyl-8-(2′,6′,6′-trimethylcyclohexenemethyl)-4-phenyl-9-oxa-2,10-dithia-5-azatricyclo[5,2,2,01,5]undecan-6-one

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at -40 - 0℃; for 10h; diastereoselective reaction;	85%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 15356-74-8, 17092-92-1, 19432-05-4, 81800-41-1
(+/-)-dihydroactinidiolide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 17h; Heating;	83%
Multi-step reaction with 2 steps 1: 81 percent / m-CPBA (50-60percent), p-TsOH / CHCl3 / 1 h / Ambient temperature 2: 83 percent / silica gel / Heating; Irradiation; microwave irradiation (1.0 kW), 5-10 min View Scheme

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 61668-14-2
S-benzyl malonic acid half thioester

: S-benzyl (E)-4-(2,6,6-trimethylcyclohex-1-enyl)but-3-enethioate

Conditions

Conditions	Yield
With 5-methoxy-1H-benzimidazole; ytterbium(III) triflate In tetrahydrofuran at 25℃; for 16h; Doebner-Knoevenagel condensation;	82%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 29951-40-4
(+/-)-aeginetolide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid In chloroform for 1h; Ambient temperature;	81%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 123-38-6
propionaldehyde

: C14H24O2

Conditions

Conditions	Yield
With water; sodium hydroxide In N,N-dimethyl-formamide at 30℃; Solvent; Temperature; Reagent/catalyst; Concentration; Aldol Condensation;	81%

: 1073-06-9
3-fluorobromobenzene

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 1441167-61-8
1-(3-fluorophenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol

Conditions

Conditions	Yield
Stage #1: 3-fluorobromobenzene With iodine; magnesium In tetrahydrofuran for 0.0833333h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In tetrahydrofuran at -78 - 20℃; for 2h;	75%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

A: 15356-74-8, 17092-92-1, 19432-05-4, 81800-41-1
(+/-)-dihydroactinidiolide

: 19432-07-6, 29951-40-4, 53537-93-2, 70561-84-1, 114247-76-6
(+/-) aeginetolide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In tetrachloromethane at 0 - 30℃; for 3h; Yields of byproduct given;	A n/a B 73%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: phenylbis[(trifluoromethyl)sulfonyl]amine

: 303779-99-9
(E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate

Conditions

Conditions	Yield
Stage #1: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: phenylbis[(trifluoromethyl)sulfonyl]amine In tetrahydrofuran; hexane at -78℃; Cooling; stereoselective reaction;	73%

: 108-37-2
1-bromo-3-chlorobenzene

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 1441167-65-2
1-(3-chlorophenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol

Conditions

Conditions	Yield
Stage #1: 1-bromo-3-chlorobenzene With iodine; magnesium In tetrahydrofuran for 0.0833333h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In tetrahydrofuran at -78 - 20℃; for 2h;	72%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

A: 186451-82-1
2,4,4-trimethyl-3-(2-oxoethyl)-2-cyclohexen-1-one

B: (3-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-acetaldehyde

Conditions

Conditions	Yield
With pyridine N-oxide; selenium(IV) oxide In 1,4-dioxane at 80℃; for 4h;	A 15% B 64%

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 303779-99-9
(E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate

Conditions

Conditions	Yield
Stage #1: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 20℃; for 0.5h;	58%

: 375-72-4
Nonafluorobutanesulfonyl fluoride

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 475673-41-7
(E)-2-(2,6,6-trimethylcyclohexen-1-yl)ethenyl nonafluorobutanesulfonate

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 1h; Heating;	52%
With potassium tert-butylate In tetrahydrofuran for 1h; Heating;	52%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 4-fluoro-3-trifluoromethylbenzyl bromide

: 1441167-75-4
2-(4-fluoro-3-(trifluoromethyl)phenyl)-1-(2,6,6-trimethylcyclohex-1-enyl)ethanol

Conditions

Conditions	Yield
Stage #1: 4-fluoro-3-trifluoromethylbenzyl bromide With magnesium In diethyl ether for 1.25h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In diethyl ether at -78 - 20℃; for 1h;	42%

: 105529-58-6
4-bromo-2-fluoro-1-(trifluoromethoxy)benzene

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 1441167-79-8
1-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-(2,6,6-trimethylcyclohex-1-enyl)ethanol

Conditions

Conditions	Yield
Stage #1: 4-bromo-2-fluoro-1-(trifluoromethoxy)benzene With magnesium In diethyl ether for 0.666667h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In diethyl ether at -78 - 20℃; for 1h;	42%

: 472-66-2
(2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde

: 620-13-3
1-bromomethyl-3-methyl-benzene

: 1441167-71-0
2-m-tolyl-1-(2,6,6-trimethylcyclohex-1-enyl)ethanol

Conditions

Conditions	Yield
Stage #1: 1-bromomethyl-3-methyl-benzene With magnesium In diethyl ether for 1.33333h; Reflux; Stage #2: (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde In diethyl ether at -78 - 20℃; for 1h;	41%

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde Specification

This chemical is called 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde, and it can also be named as beta-Homocyclocitral. With the molecular formula of C₁₁H₁₈O, its molecular weight is 166.26. The CAS registry number of this chemical is 472-66-2.

Other characteristics of the 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde can be summarised as followings: (1)ACD/LogP: 3.94; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.94; (4)ACD/LogD (pH 7.4): 3.94; (5)ACD/BCF (pH 5.5): 581.21; (6)ACD/BCF (pH 7.4): 581.21; (7)ACD/KOC (pH 5.5): 3313.69; (8)ACD/KOC (pH 7.4): 3313.69; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 17.07 ?2; (13)Index of Refraction: 1.45; (14)Molar Refractivity: 50.8 cm3; (15)Molar Volume: 189 cm3; (16)Polarizability: 20.14 10-24cm3; (17)Surface Tension: 25.8 dyne/cm; (18)Density: 0.879 g/cm3; (19)Flash Point: 76.8 °C; (20)Enthalpy of Vaporization: 48.03 kJ/mol; (21)Boiling Point: 243.3 °C at 760 mmHg; (22)Vapour Pressure: 0.0324 mmHg at 25°C.

Production method of this chemical: The 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde could be obtained by the reactant of 2-(2-methoxy-vinyl)-1,3,3-trimethyl-cyclohexene. This reaction needs the reagent of 60percent perchloric acid, and the solvent of tetrahydrofuran. The yield is 94 %. In addition, this reaction should be taken for 30 minutes at ambient temperature.

Uses of this chemical: The 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde could react with pyrrolidine, and obtain the 1-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]pyrrolidine. This reaction needs the solvent of toluene. The yield is 96 %. In addition, this reaction should be taken for 1 hour at the temperature of 60 °C.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.InChI: InChI=1/C11H18O/c1-9-5-4-7-11(2,3)10(9)6-8-12/h8H,4-7H2,1-3H3
2.Smiles:C=1(C(CCCC1C)(C)C)CC=O

Product Name

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde

Synthetic route

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde Specification

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