Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodic acid In N,N-dimethyl-formamide at 20℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; | 99% |
With 5-nitro-3-oxo-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl acetate In N,N-dimethyl-formamide at 60℃; for 24h; Reagent/catalyst; | 98% |
With N-Bromosuccinimide; β‐cyclodextrin In methanol; water; acetone at 20℃; for 8h; | 96% |
Conditions | Yield |
---|---|
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 1.5h; | 98% |
With 4Na(1+)*6H(1+)*NiMo6O24(10-)=Na4H6NiMo6O24; oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 12h; Irradiation; | 91% |
With sodium nitrate; acetic acid In water for 8h; Reflux; | 83% |
With potassium hydroxide; cetyltrimethylammonim bromide; potassium nitrate In water for 7.5h; pH=10 - 11; Reflux; | 82% |
With (NH4)4[ZnMo6O18(OH)6]; oxygen In water; acetonitrile at 60℃; under 760.051 Torr; for 12h; | 81% |
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trimethyl-benzene With titanium tetrachloride In dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: Dichloromethyl methyl ether In dichloromethane at 0℃; for 0.75h; Inert atmosphere; regioselective reaction; | 96% |
With silver trifluoromethanesulfonate In dichloromethane at -78℃; for 0.333333h; Inert atmosphere; | 69% |
With dichloromethane; titanium tetrachloride |
2,4,6-trimethylbenzaldehyde oxime
mesytaldehyde
Conditions | Yield |
---|---|
With chromium trioxide-kieselghur reagent In dichloromethane for 3h; Reflux; | 92% |
With 2-iodoxybenzoic acid; β‐cyclodextrin In water; acetone at 20℃; for 12h; | 90% |
With iodobenzene; β‐cyclodextrin; potassium bromide In water; acetone at 20℃; for 12h; | 90% |
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In dichloromethane at -10℃; for 0.333333h; Stage #2: 1,3,5-trimethyl-benzene In dichloromethane at -5℃; for 6.16667h; Solvent; Reflux; | 90.3% |
mesytaldehyde
Conditions | Yield |
---|---|
With water at 20℃; | 89% |
Conditions | Yield |
---|---|
With sodium periodate In N,N-dimethyl-formamide at 150℃; for 0.833333h; | 87% |
With sodium periodate; N,N-dimethyl-formamide at 150℃; for 0.833333h; | 87% |
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 65℃; for 2.5h; | 80% |
With potassium hydroxide; 2-nitropropane In isopropyl alcohol at 40 - 45℃; for 0.333333h; | 75% |
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 60℃; |
mesytaldehyde
Conditions | Yield |
---|---|
With Bromoform; potassium tert-butylate In hexane at -78℃; for 3h; | 87% |
Multi-step reaction with 2 steps 1: chloroform; water / 24 h / 20 °C 2: air / 20 °C View Scheme |
Dichloromethyl methyl ether
1,3,5-trimethyl-benzene
A
mesytaldehyde
B
1-(dichloromethyl)-2,4,6-trimethylbenzene
C
3-dichloromethyl-2,4,6-trimethylbenzaldehyde
D
1,3-bis(dichloromethyl)mesitylene
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 20 - 25℃; for 0.25h; Further byproducts given; | A 84% B 3 % Chromat. C 3 % Chromat. D 1 % Chromat. |
With titanium tetrachloride In dichloromethane for 0.25h; Ambient temperature; Yields of byproduct given; | A 84% B n/a C n/a D n/a |
With aluminium trichloride In dichloromethane at 20 - 25℃; for 0.25h; Further byproducts given; | A 55 % Chromat. B 10% C 10 % Chromat. D 25 % Chromat. |
Conditions | Yield |
---|---|
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 3.5h; Reagent/catalyst; Schlenk technique; Inert atmosphere; | A 79% B 65% |
2,4,6-trimethylbenzyl mercaptan
mesytaldehyde
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; tetrakis(pyridine)silver(II) peroxodisulfate; oxygen In N,N-dimethyl-formamide at 23℃; under 760.051 Torr; Irradiation; | 76% |
2,4,6-trimethylphenyl bromide
N,N-dimethyl-formamide
mesytaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,4,6-trimethylphenyl bromide With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃; | 75% |
1-(2,4,6-trimethylphenyl)prop-2-en-1-ol
A
mesytaldehyde
B
E-3-(2,4,6-trimethylphenyl)propenal
Conditions | Yield |
---|---|
With periodic acid; pyridinium chlorochromate In acetonitrile at 0 - 20℃; for 2h; stereoselective reaction; | A 12% B 74% |
2,4,6-trimethylbenzaldehyde azine
mesytaldehyde
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In water; acetonitrile at 50℃; for 18h; Oxidation; | 71% |
N,N,N',N'-tetraformylhydrazine
1,3,5-trimethyl-benzene
A
mesytaldehyde
B
2,4,6-trimethylbenzaldehyde azine
Conditions | Yield |
---|---|
Stage #1: N,N,N',N'-tetraformylhydrazine; 1,3,5-trimethyl-benzene With aluminium trichloride In 1,2-dichloro-ethane at -11 - 0℃; for 18h; Stage #2: With water | A 21% B 68% |
Conditions | Yield |
---|---|
With aluminium trichloride In chlorobenzene at -15 - -7℃; for 16h; Formylation; | 67% |
3-pyridinecarboxylic acid ethyl ester
A
mesytaldehyde
B
ethyl 4-chloronicotinate
Conditions | Yield |
---|---|
With (trichloromethyl)mesitylene In chloroform for 576h; Ambient temperature; | A n/a B 64% |
Conditions | Yield |
---|---|
With α,α,α,2,4,6-hexachlorotoluene In chloroform for 720h; Ambient temperature; | A 64% B 49% |
Conditions | Yield |
---|---|
With 3-Methylpyridine In chloroform for 720h; Ambient temperature; | A 64% B 49% |
Conditions | Yield |
---|---|
With 1,2,3,4-tetrahydroisoquinoline In acetonitrile at 20℃; Green chemistry; | 63% |
1,3-dichloro-2,4,6-trimethylbenzene
N,N-dimethyl-formamide
A
mesytaldehyde
B
2,4,6-trimethylisophthalic dialdehyde
Conditions | Yield |
---|---|
Stage #1: 1,3-dichloro-2,4,6-trimethylbenzene With naphthalene; lithium In diethyl ether at 20℃; for 4.55h; Stage #2: N,N-dimethyl-formamide In diethyl ether at 20℃; Cooling with ice; | A 12% B 61% |
Dichloromethyl methyl ether
dimesitylmethane
A
mesytaldehyde
B
2,4,6-trimethyl-3-(chloromethyl)benzaldehyde
C
3-chloromethyl-2,4,6-trimethylbenzylidene dichloride
D
dimesitylmethane-3,3'-dicarbaldehyde
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane for 0.25h; Further byproducts given; | A 20 % Chromat. B 10 % Chromat. C 10 % Chromat. D 60% |
trifluoromethanesulphonyloxy-methylene-N,N-dimethyliminium trifluoromethanesulphonate
1,3,5-trimethyl-benzene
mesytaldehyde
Conditions | Yield |
---|---|
at 125℃; for 96h; | 60% |
Conditions | Yield |
---|---|
With rhodium(III) chloride trihydrate; hydrogen; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 90℃; under 7500.75 Torr; for 12h; Autoclave; | 60% |
Conditions | Yield |
---|---|
With aluminum (III) chloride In chlorobenzene at -12 - 18℃; for 22h; | 57% |
Conditions | Yield |
---|---|
With trifuran-2-yl-phosphane; palladium diacetate In tetrahydrofuran; toluene at 0℃; for 15h; Schlenk technique; | 57% |
2-(2,4,6-trimethylphenyl)-2-hydroxyacetonitrile
A
mesytaldehyde
B
mesitylenecarboxylic acid
Conditions | Yield |
---|---|
Stage #1: 2-hydroxy-2-(2,4,6-trimethylphenyl)acetonitrile With (η(6)-benzene)chloro[1,2-bis(diphenylphosphino)ethane]ruthenium(II) chloride In benzene at 120℃; for 24h; Inert atmosphere; Schlenk technique; Stage #2: With water In dichloromethane; ethyl acetate; benzene for 24h; | A 40% B 55% |
Conditions | Yield |
---|---|
With polymer(resin Amberlyst A-26)-supported tetracarbonylhydridoferrate anion In dichloromethane for 1h; Heating; | 53% |
With Pd-BaSO4; xylene Hydrogenation; | |
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal In ethyl acetate at 25℃; under 760 Torr; for 2h; Yield given; | |
With triethylsilane; bis-triphenylphosphine-palladium(II) chloride; (Z)-N,N-diisopropyl-2-styrylbenzamide In tetrahydrofuran at 65℃; for 24h; Inert atmosphere; chemoselective reaction; |
Conditions | Yield |
---|---|
With V2O5/TiO2; dihydrogen peroxide In water; acetonitrile at 30℃; for 4h; Sealed tube; | 52% |
Conditions | Yield |
---|---|
In benzene for 10h; Heating; | 100% |
Conditions | Yield |
---|---|
With lithium tetrafluoroborate at 25℃; for 3h; | 100% |
With iodine In chloroform at 20℃; for 0.166667h; | 90% |
mesytaldehyde
acetylenemagnesium bromide
1-(2,4,6-trimethylphenyl)prop-2-yn-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 2h; | 100% |
Conditions | Yield |
---|---|
In water at 20℃; Inert atmosphere; | 100% |
mesytaldehyde
1-propynylmagnesium bromide
chloromethyl methyl ether
Conditions | Yield |
---|---|
Stage #1: mesytaldehyde; 1-propynylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 1.5h; Schlenk technique; Inert atmosphere; Stage #2: chloromethyl methyl ether In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere; | 100% |
mesytaldehyde
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: mesytaldehyde In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With trimethylamine-N-oxide; sodium formate; C34H44FeN4O4(2+)*2I(1-) In water at 80℃; for 24h; Inert atmosphere; Schlenk technique; | 99% |
With sodium formate; N-tosylethylenediamine; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] at 80℃; for 0.7h; | 97% |
With formic acid; C20H29ClIrN4(1+)*Cl(1-) In water at 80℃; for 0.25h; chemoselective reaction; | 97% |
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In methanol at 25℃; under 760.051 Torr; for 0.833333h; | 99% |
Clemensen redn.; | |
With [Ru(OH2)3(4'-phenyl-2,2':6',2''-terpy)](OTf)2; hydrogen In sulfolane; water at 175℃; under 56887.8 Torr; for 3h; | 8 %Chromat. |
Conditions | Yield |
---|---|
With C32H39Br2MgN2(1-)*C16H32LiO4(1+) In chloroform-d1 at 20℃; for 0.5h; Inert atmosphere; Glovebox; | 99% |
With [[{(2,6-iPr2C6H3N)P(Ph2)}2N]AlMe]+[MeB(C6F5)3]- In neat (no solvent) at 25 - 28℃; for 0.0833333h; chemoselective reaction; | 98% |
With C29H38AlN4O2(1+)*CF3O3S(1-) at 20℃; for 0.333333h; Catalytic behavior; Inert atmosphere; Schlenk technique; | 95% |
Conditions | Yield |
---|---|
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 tris[2-(4,6-difluorophenyl)pyridinato-C2,N]-iridium(III); oxygen In acetonitrile at 20℃; Irradiation; Sealed tube; Green chemistry; chemoselective reaction; | 90% |
mesytaldehyde
α-fluoro-α-(phenylselanyl)acetic acid ethyl ester
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethylpiperidinyl-lithium; methanesulfonyl chloride In tetrahydrofuran at -78℃; | 99% |
mesytaldehyde
(trifluoromethyl)trimethylsilane
Conditions | Yield |
---|---|
With dmap; tetrabutylammonium tricarbonylnitrosylferrate In tetrahydrofuran at 30℃; for 14h; Schlenk technique; Inert atmosphere; Sealed tube; | 99% |
With 4 A molecular sieve In dimethyl sulfoxide at 20℃; for 0.25h; | 100 % Spectr. |
With cesium fluoride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; |
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In methanol at 23℃; for 12h; | 99% |
With CSA In methanol at 20℃; for 12h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
Stage #1: methyl 1-(1-ethynyl)-2-naphthoate With n-butyllithium Stage #2: mesytaldehyde Further stages.; | 99% |
Conditions | Yield |
---|---|
With zinc In dimethyl sulfoxide for 2h; Barbier Coupling Reaction; Milling; | 99% |
With water; tin(ll) chloride at 20℃; for 2h; | 97% |
With ammonium chloride; zinc In tetrahydrofuran at 20℃; for 1h; | 92% |
Stage #1: allyl bromide With magnesium In tetrahydrofuran for 8h; Sealed tube; Inert atmosphere; Stage #2: mesytaldehyde In tetrahydrofuran Sealed tube; Inert atmosphere; |
mesytaldehyde
(R,R)-1,2-diphenylethylenediamine
(1R,2R)-1,2-diphenyl-N1-(2,4,6-trimethylbenzylidene)ethane-1,2-diamine
Conditions | Yield |
---|---|
In water at 20℃; for 16h; | 99% |
mesytaldehyde
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
4,4,5,5-tetramethyl-2-((2,4,6-trimethylbenzyl)oxy)-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With C45H69NdO3*2C4H8O In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; | 99% |
With [Ag((cyclohexyl)3P)(HMDS)] In benzene-d6 at 20℃; for 8h; Inert atmosphere; | 97% |
With C19H25AsN2O In benzene-d6 at 20℃; for 0.5h; Inert atmosphere; Glovebox; Schlenk technique; | 90% |
Conditions | Yield |
---|---|
With titanium(IV) tetrabutoxide; triethylsilyl chloride In dichloromethane at 20℃; | A n/a B 99% |
Conditions | Yield |
---|---|
With carbon dioxide In ethanol at 20℃; under 760.051 Torr; for 18h; Sealed tube; | 99% |
With sodium hydrogensulfite In water; ethyl acetate at 40℃; for 20h; Inert atmosphere; Schlenk technique; Sealed tube; |
mesytaldehyde
Conditions | Yield |
---|---|
In ethanol for 2h; Reflux; | 99% |
mesytaldehyde
N-methylhydroxyamine hydrochloride
C-mesityl-N-methylnitrone
Conditions | Yield |
---|---|
With triethylamine In chloroform for 22h; | 98% |
Conditions | Yield |
---|---|
Stage #1: 1-ethynylnaphthalene With n-butyllithium Stage #2: mesytaldehyde Further stages.; | 98% |
mesytaldehyde
Chloroiodomethane
2-chloro-1-(2,4,6-trimethylphenyl)ethanol
Conditions | Yield |
---|---|
With methyllithium In tetrahydrofuran at -40℃; Flow reactor; | 98% |
Stage #1: Chloroiodomethane With TurboGrignard In tetrahydrofuran at -20℃; for 0.000277778h; Flow reactor; Stage #2: mesytaldehyde In tetrahydrofuran at -20℃; for 0.000444444h; Flow reactor; | 95% |
Conditions | Yield |
---|---|
With cerium(III) chloride heptahydrate In ethanol at 20℃; for 0.0166667h; Green chemistry; diastereoselective reaction; | 98% |
With water; acetic acid In neat (no solvent) at 20℃; for 0.0833333h; Green chemistry; stereoselective reaction; | 94% |
mesytaldehyde
Diphenylphosphine oxide
(2,4,6-trimethylbenzoyl)diphenylphosphine oxide
Conditions | Yield |
---|---|
Stage #1: mesytaldehyde; Diphenylphosphine oxide In dichloromethane for 6h; Green chemistry; Stage #2: With ammonium metavanadate; dihydrogen peroxide at 8 - 20℃; for 5.5h; Reagent/catalyst; Green chemistry; | 98% |
mesytaldehyde
C6H5NHBO2C2(CH3)4
N-(2,4,6-trimethylbenzylidene)aniline
Conditions | Yield |
---|---|
In benzene-d6 at 25℃; for 1h; Inert atmosphere; Schlenk technique; | 98% |
mesytaldehyde
acetophenone
(E)-1-phenyl-3-[(2,4,6-trimethylphenyl)]prop-2-en-1-one
Conditions | Yield |
---|---|
Stage #1: mesytaldehyde; acetophenone With potassium hydroxide In ethanol; water at 20℃; for 12h; Claisen Schmidt condensation; Stage #2: With hydrogenchloride In ethanol; water pH=3 - 4; | 97% |
With sodium hydroxide In ethanol; water at 20℃; for 0.0833333h; | 72% |
With sodium hydroxide at 0℃; | |
Stage #1: acetophenone With sodium hydroxide In ethanol; water at 0 - 20℃; for 1.33333h; Stage #2: mesytaldehyde In ethanol; water at 20℃; |
The IUPAC name of Mesityl aldehyde is 2,4,6-trimethylbenzaldehyde. With the CAS registry number 487-68-3, it is also named as 2-Mesitylenecarboxaldehyde; Benzaldehyde, 2,4,6-trimethyl-. The product's categories are aromatic aldehydes & derivatives (substituted), benzaldehyde and aromatics. It is light yellow liquid which is soluble in benzene and toluene. It is sensitive to air. So it should be stored in a tightly closed container which is placed in a cool, dry, well-ventilated area away from incompatible substances.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.02; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.02; (4)ACD/LogD (pH 7.4): 3.02; (5)#H bond acceptors: 1; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 1; (8)Index of Refraction: 1.546; (9)Molar Refractivity: 47.48 cm3; (10)Molar Volume: 149.9 cm3; (11)Polarizability: 18.82×10-24 cm3; (12)Surface Tension: 35.2 dyne/cm; (13)Enthalpy of Vaporization: 47.85 kJ/mol; (14)Vapour Pressure: 0.0357 mmHg at 25°C; (15)Rotatable Bond Count: 1; (16)Tautomer Count: 4; (17)Exact Mass: 148.088815; (18)MonoIsotopic Mass: 148.088815; (19)Topological Polar Surface Area: 17.1; (20)Heavy Atom Count: 11.
Preparation of Mesityl aldehyde: It can be obtained by 2,4,6-trimethyl-benzoyl chloride. This reaction needs reagent palladium-barium sulfate and xylene by Hydrogenation.
Uses of Mesityl aldehyde: It can be used in organic synthesis, and also can be used as medicine and other fine chemical products. It can reacts with 2,3-dihydro-furan to get endo-7-(2,4,6-Trimethylphenyl)-2,6-dioxabicyclo[3.2.0]heptan. This reaction needs reagent K2CO3 and solvent benzene at temperature of 6-8 °C and irradiation. The reaction time is 8.5 hours. The yield is 97%.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
People can use the following data to convert to the molecule structure.
1. SMILES: O=Cc1c(C)cc(C)cc1C;
2. InChI: InChI=1/C10H12O/c1-7-4-8(2)10(6-11)9(3)5-7/h4-6H,1-3H3.
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