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697-82-5 Usage

Description

2,3,5-Trimethylphenol is an organic compound with the chemical formula C9H12O. It is a white crystalline solid that is soluble in organic solvents and has a characteristic aromatic smell. It is a derivative of phenol, with three methyl groups attached to the benzene ring at the 2nd, 3rd, and 5th positions.

Uses

Used in Pharmaceutical Industry:
2,3,5-Trimethylphenol is used as an intermediate in the synthesis of tretinoin, a medication used to treat acne and other skin conditions. It is also used in the production of other pharmaceutical compounds.
Used in Organic Synthesis:
2,3,5-Trimethylphenol is used as a building block in the synthesis of various organic compounds, including dyes, resins, and polymers. Its reactivity and functional groups make it a versatile compound for use in chemical reactions.
Used in Chemical Research:
2,3,5-Trimethylphenol is used as a reference compound in chemical research, particularly in studies involving the synthesis and characterization of new compounds. Its well-defined structure and properties make it a useful tool for understanding reaction mechanisms and developing new synthetic methods.

Preparation

2,3,5-trimethylphenol can be synthesized from 1,2,4-trimethylbenzene.

Purification Methods

Crystallise the phenol from water or pet ether. [Beilstein 6 IV 3248.]

Check Digit Verification of cas no

The CAS Registry Mumber 697-82-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,9 and 7 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 697-82:
(5*6)+(4*9)+(3*7)+(2*8)+(1*2)=105
105 % 10 = 5
So 697-82-5 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O/c1-6-4-7(2)8(3)9(10)5-6/h4-5,10H,1-3H3

697-82-5 Well-known Company Product Price

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  • Alfa Aesar

  • (A10745)  2,3,5-Trimethylphenol, 98+%   

  • 697-82-5

  • 25g

  • 134.0CNY

  • Detail
  • Alfa Aesar

  • (A10745)  2,3,5-Trimethylphenol, 98+%   

  • 697-82-5

  • 100g

  • 500.0CNY

  • Detail
  • Alfa Aesar

  • (A10745)  2,3,5-Trimethylphenol, 98+%   

  • 697-82-5

  • 1000g

  • 4014.0CNY

  • Detail
  • Sigma-Aldrich

  • (34308)  2,3,5-Trimethylphenol  PESTANAL®, analytical standard

  • 697-82-5

  • 34308-250MG

  • 329.94CNY

  • Detail

697-82-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,3,5-trimethylphenol

1.2 Other means of identification

Product number -
Other names 2,3,5-Trimethylphenol

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:697-82-5 SDS

697-82-5Synthetic route

O-(4-Nitrobenzyl)-2,3,5-trimethylphenol

O-(4-Nitrobenzyl)-2,3,5-trimethylphenol

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With indium; ammonium chloride In ethanol for 18h; Debenzylation; Heating;100%
With indium; ammonium chloride In methanol for 18h; Heating;100%
1,2,5-Trimethyl-3-trityloxy-benzene

1,2,5-Trimethyl-3-trityloxy-benzene

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With tetrahydrofuran; titanium(III) chloride; lithium for 14h; Heating;92%
2,3,5-Trimethyl-(4-methylphenylsulfonyloxy)benzene
312609-91-9

2,3,5-Trimethyl-(4-methylphenylsulfonyloxy)benzene

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With titanium(III) chloride; lithium In tetrahydrofuran at 25℃; for 18h; Substitution;91%
2,4,6-trimethylpyrylium tetrafluoroborate
773-01-3

2,4,6-trimethylpyrylium tetrafluoroborate

dimethylsulfoxonium methylide
70775-39-2, 5367-24-8

dimethylsulfoxonium methylide

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
In tetrahydrofuran; dimethyl sulfoxide 1.) -5 deg C, 1 h, 2.) room temperature, 7 h;80%
methanol
67-56-1

methanol

2,3-Dimethylphenol
526-75-0

2,3-Dimethylphenol

A

2,3,6-trimethylphenol
2416-94-6

2,3,6-trimethylphenol

B

2,3,4-trimethylphenol
526-85-2

2,3,4-trimethylphenol

C

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
Pd-containing mordenite at 350℃;A 80%
B 5%
C 5%
methanol
67-56-1

methanol

3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

A

3,4,5-trimethylphenol
527-54-8

3,4,5-trimethylphenol

B

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
Pd-containing mordenite at 350℃;A 6%
B 70%
1,2,4-Trimethylbenzene
95-63-6

1,2,4-Trimethylbenzene

A

2,4-dimethylbenzyl alcohol
16308-92-2

2,4-dimethylbenzyl alcohol

B

Trimethylhydroquinone
700-13-0

Trimethylhydroquinone

C

2,4,5-trimethylphenol
496-78-6

2,4,5-trimethylphenol

D

2,3,6-trimethylphenol
2416-94-6

2,3,6-trimethylphenol

E

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

F

2,5-dimethylbenzyl alcohol
53957-33-8

2,5-dimethylbenzyl alcohol

Conditions
ConditionsYield
With glucose dehydrogenase; D-glucose; P450 BM3 R47S, Y51W, A330F, I401M mutant; NADPH; catalase; ascorbic acid In aq. phosphate buffer; dimethyl sulfoxide pH=7.5; Catalytic behavior; Enzymatic reaction;A 25%
B 23%
C 28%
D 5%
E 8%
F 9%
formaldehyd
50-00-0

formaldehyd

3,5-dimethyl-2-cyclohexen-1-one
1123-09-7

3,5-dimethyl-2-cyclohexen-1-one

diethyl amine hydrochloride
660-68-4

diethyl amine hydrochloride

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With hydrogenchloride; ethanol Behandeln des Reaktionsprodukts mit HCl in Aether und Erhitzen der erhaltenen Hydrochloride unter vermindertem Druck auf 200-235grad;
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

A

3,4,5-trimethylphenol
527-54-8

3,4,5-trimethylphenol

B

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With bromine; 1,2,4-Trichlorobenzene
3,5-dimethyl-2-piperidin-1-ylmethyl-phenol
68097-90-5

3,5-dimethyl-2-piperidin-1-ylmethyl-phenol

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With calcium hydroxide
With 1,4-dioxane; copper oxide-chromium oxide at 165℃; Hydrogenolyse;
2-(Morpholinomethyl)-3,5-dimethylphenol
14944-83-3

2-(Morpholinomethyl)-3,5-dimethylphenol

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With 1,4-dioxane; copper oxide-chromium oxide at 165℃; Hydrogenolyse;
2-methylmethoxybenzene
578-58-5

2-methylmethoxybenzene

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With aluminium trichloride at 100℃;
3,4,5-trimethylphenol
527-54-8

3,4,5-trimethylphenol

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With aluminium trichloride at 100℃;
2-chloro-3,5,6-trimethylphenol
90416-29-8

2-chloro-3,5,6-trimethylphenol

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With sodium hydroxide; aluminum nickel
2,3,5-trimethylaniline
767-77-1

2,3,5-trimethylaniline

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
Diazotization;
With sulfuric acid; sodium nitrite 1.) 0 deg C, 1 h, 2.) reflux, 2 h; Yield given. Multistep reaction;
2-Dimethylaminomethyl-3,5-dimethyl-phenol
63487-28-5

2-Dimethylaminomethyl-3,5-dimethyl-phenol

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With 1,4-dioxane; copper oxide-chromium oxide at 165℃; Hydrogenolyse;
Trimethylhydroquinone
700-13-0

Trimethylhydroquinone

acetic anhydride
108-24-7

acetic anhydride

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With hydrogen iodide; acetic acid at 150℃;
4-Hexadecyloxy-2,3,6-trimethyl-phenol
103045-07-4

4-Hexadecyloxy-2,3,6-trimethyl-phenol

acetic anhydride
108-24-7

acetic anhydride

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With hydrogen iodide; acetic acid at 150℃;
dihydroisophorone
873-94-9

dihydroisophorone

A

3,4,5-trimethylphenol
527-54-8

3,4,5-trimethylphenol

B

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With sulfuric acid at 20℃;
methanol
67-56-1

methanol

3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Conditions
ConditionsYield
With activated bauxit at 450℃; under 12503.6 Torr;
methanol
67-56-1

methanol

3,5-Dimethylphenol
108-68-9

3,5-Dimethylphenol

A

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

B

2,3,5,6-tetramethylphenol
527-35-5

2,3,5,6-tetramethylphenol

C

pentamethylphenol
2819-86-5

pentamethylphenol

Conditions
ConditionsYield
at 450℃; under 7355.08 - 12503.6 Torr; Leiten ueber aktivierten Bauxit;
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

(2,3,5-Trimethyl-phenoxy)-acetic acid methyl ester
95450-49-0

(2,3,5-Trimethyl-phenoxy)-acetic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In butanone for 5.5h; Heating;100%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

2,3,5-Trimethylphenyl trifluoromethanesulfonate
209684-76-4

2,3,5-Trimethylphenyl trifluoromethanesulfonate

Conditions
ConditionsYield
In pyridine at 0 - 20℃; for 1h;100%
With triethylamine In toluene at 20℃; Flow reactor;
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

methyl iodide
74-88-4

methyl iodide

2,3,5-trimethylanisole
20469-61-8

2,3,5-trimethylanisole

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide for 10h; Ambient temperature;99.8%
With sodium hydride In dimethyl sulfoxide for 10h;98%
Stage #1: 2,3,5-trimethylphenol With sodium hydride In tetrahydrofuran at 0℃; for 1h;
Stage #2: methyl iodide In tetrahydrofuran at 0℃; for 3h;
92%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

C18H23O2PS2
1394064-56-2

C18H23O2PS2

Conditions
ConditionsYield
With tetraphosphorus decasulfide for 0.0694444h; Microwave irradiation;99.3%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

2,3,5-trimethylanisole
20469-61-8

2,3,5-trimethylanisole

Conditions
ConditionsYield
With dimanganese decacarbonyl at 180℃; for 1h; Reagent/catalyst;99%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

triethylamine
121-44-8

triethylamine

C18H23O2PS2*C6H15N
1394064-58-4

C18H23O2PS2*C6H15N

Conditions
ConditionsYield
Stage #1: 2,3,5-trimethylphenol With tetraphosphorus decasulfide In chloroform at 35℃;
Stage #2: triethylamine In chloroform
98%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

propionic acid
802294-64-0

propionic acid

2-ethyl-3,5,7,8-tetramethyl-4H-chromen-4-one

2-ethyl-3,5,7,8-tetramethyl-4H-chromen-4-one

Conditions
ConditionsYield
With titanium tetrachloride In neat (no solvent) at 100℃; for 5h; Inert atmosphere;98%
benzofuran-2-ylmethyl acetate
62452-62-4

benzofuran-2-ylmethyl acetate

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

C18H18O2

C18H18O2

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate; XPhos In tetrahydrofuran; acetonitrile at 120℃; Inert atmosphere; regioselective reaction;98%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

2,3,5-Trimethyl-1-(2-methyl-2-propenyloxy)benzene
142874-36-0

2,3,5-Trimethyl-1-(2-methyl-2-propenyloxy)benzene

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide; acetone Heating;97%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

2,3,5-Trimethyl-1,4-benzoquinone
935-92-2

2,3,5-Trimethyl-1,4-benzoquinone

Conditions
ConditionsYield
With titanium superoxide; dihydrogen peroxide; acetic acid In water at 50℃; for 2h;96%
With oxygen In water; acetonitrile at 40℃; under 15001.5 Torr; for 1h; Green chemistry;94%
With 5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrin; oxygen In chloroform; acetonitrile for 24h; Product distribution; Further Variations:; Reagents; Irradiation;93%
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

O-(4-Nitrobenzyl)-2,3,5-trimethylphenol

O-(4-Nitrobenzyl)-2,3,5-trimethylphenol

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 3h;96%
2-methyl-3-bromo-1-propene
1458-98-6

2-methyl-3-bromo-1-propene

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

2,3,5-Trimethyl-1-(2-methyl-2-propenyloxy)benzene
142874-36-0

2,3,5-Trimethyl-1-(2-methyl-2-propenyloxy)benzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 15h;96%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 15h;96%
trimethylsilyl isothiocyanate
2290-65-5

trimethylsilyl isothiocyanate

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

2,3,5-trimethyl-4-thiocyanatophenol
196944-10-2

2,3,5-trimethyl-4-thiocyanatophenol

Conditions
ConditionsYield
With 1-chloro-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one In dichloromethane at 20℃; for 1h;96%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

allyl bromide
106-95-6

allyl bromide

1,2,5-trimethyl-3-(prop-2-en-1-yloxy)benzene
53546-78-4

1,2,5-trimethyl-3-(prop-2-en-1-yloxy)benzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;95%
With potassium carbonate; acetone
With sodium hydroxide In N,N-dimethyl-formamide
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

4-bromo-2,3,5-trimethylphenol

4-bromo-2,3,5-trimethylphenol

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol; dichloromethane for 0.333333h;95%
With 1-butyl-3-methylimidazolium tribromide at -10℃;86%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

Bromo-acetic acid 2,3,5-trimethyl-phenyl ester
110699-68-8

Bromo-acetic acid 2,3,5-trimethyl-phenyl ester

Conditions
ConditionsYield
With pyridine In diethyl ether for 1h; Ambient temperature;94%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

2,3,5-trimethylcyclohexanol
116-02-9

2,3,5-trimethylcyclohexanol

Conditions
ConditionsYield
With potassium hydroxide; Raney Ni-Al; water at 90℃; for 20h;91.2%
With nickel at 155℃; Hydrogenation;
With nickel; sodium(2,3,5-(methyl)3phenoxide) at 170℃; under 95616 - 110326 Torr; Hydrogenation;
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

4-iodo-2,3,5-trimethyl-phenol
7282-02-2

4-iodo-2,3,5-trimethyl-phenol

Conditions
ConditionsYield
With iodine; oxygen; copper(II) nitrate In water at 80℃; under 760.051 Torr; for 3h; Green chemistry; regioselective reaction;91%
With hydrogenchloride; potassium iodate; potassium iodide In methanol at 20℃; for 0.5h;62.2%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Bromoacetaldehyde diethyl acetal
2032-35-1

Bromoacetaldehyde diethyl acetal

1-(2,2-diethoxyethoxy)-2,3,5-trimethylbenzene

1-(2,2-diethoxyethoxy)-2,3,5-trimethylbenzene

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl acetamide at 20℃; Heating;91%
2,2-(dimethyl)-2-phenylacetaldehyde
3805-10-5

2,2-(dimethyl)-2-phenylacetaldehyde

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydrobenzofuran
142874-60-0

2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydrobenzofuran

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In toluene at 110℃; for 1h;90%
2-chloroethyl ethyl ether
628-34-2

2-chloroethyl ethyl ether

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

1-(2-ethoxyethoxy)-2,3,5-trimethylbenzene
865138-71-2

1-(2-ethoxyethoxy)-2,3,5-trimethylbenzene

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20 - 70℃; for 48h;90%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

4,4-dimethoxy-3,5-dimethylcyclohexa-2,5-dien-1-one
116760-59-9

4,4-dimethoxy-3,5-dimethylcyclohexa-2,5-dien-1-one

5-methoxy-2',3',4,6,6'-pentamethyl-[1,1'-biphenyl]-2,4'-diol

5-methoxy-2',3',4,6,6'-pentamethyl-[1,1'-biphenyl]-2,4'-diol

Conditions
ConditionsYield
With methanesulfonic acid at 20℃; regioselective reaction;90%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Propiolic acid
471-25-0

Propiolic acid

5,7,8-trimethyl-2H-chromen-2-one
40662-19-9

5,7,8-trimethyl-2H-chromen-2-one

Conditions
ConditionsYield
With C62H54Cl2N4Pd2; trifluoroacetic acid at 20℃; for 12.0833h; Cooling with ice; regioselective reaction;90%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

7-(4-fluorophenyl)-7-hydroxyheptanoic acid
103187-28-6

7-(4-fluorophenyl)-7-hydroxyheptanoic acid

7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoic acid
121099-61-4

7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoic acid

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 60℃; for 6h;89%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

ethyl 2-(2,3,5-trimethylphenyl)oxypropionate
156462-53-2

ethyl 2-(2,3,5-trimethylphenyl)oxypropionate

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl-formamide; acetone Heating;89%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

1-(3-methoxyphenyl)-2-(2,3,5-trimethylphenoxy)ethanone
820258-31-9

1-(3-methoxyphenyl)-2-(2,3,5-trimethylphenoxy)ethanone

Conditions
ConditionsYield
88%
2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

propionic acid
802294-64-0

propionic acid

2,3,5-trimethylphenyl propionate

2,3,5-trimethylphenyl propionate

Conditions
ConditionsYield
With tin(IV) chloride In neat (no solvent) at 100℃; for 8h; Inert atmosphere; chemoselective reaction;88%

697-82-5Relevant articles and documents

REARRANGEMENT OF DIMETHYLPHENYLACYLATES USING ZEOLITES

-

Page/Page column 9-10; 14, (2021/08/14)

The present invention relates to a Fries rearrangement of specific dimethylphenylacylates to form the desired respective hydroxyaryl ketones having two methyl groups bound to the aromatic ring. It has been found that the process is surprisingly very specific in view of the number and position of the methyl group(s) bound to the aromatic ring.

An Enzymatic Route to α-Tocopherol Synthons: Aromatic Hydroxylation of Pseudocumene and Mesitylene with P450 BM3

Dennig, Alexander,Weingartner, Alexandra Maria,Kardashliev, Tsvetan,Müller, Christina Andrea,Tassano, Erika,Schürmann, Martin,Ruff, Anna Jo?lle,Schwaneberg, Ulrich

, p. 17981 - 17991 (2017/11/29)

Aromatic hydroxylation of pseudocumene (1 a) and mesitylene (1 b) with P450 BM3 yields key phenolic building blocks for α-tocopherol synthesis. The P450 BM3 wild-type (WT) catalyzed selective aromatic hydroxylation of 1 b (94 %), whereas 1 a was hydroxylated to a large extent on benzylic positions (46–64 %). Site-saturation mutagenesis generated a new P450 BM3 mutant, herein named “variant M3” (R47S, Y51W, A330F, I401M), with significantly increased coupling efficiency (3- to 8-fold) and activity (75- to 230-fold) for the conversion of 1 a and 1 b. Additional π–π interactions introduced by mutation A330F improved not only productivity and coupling efficiency, but also selectivity toward aromatic hydroxylation of 1 a (61 to 75 %). Under continuous nicotinamide adenine dinucleotide phosphate recycling, the novel P450 BM3 variant M3 was able to produce the key tocopherol precursor trimethylhydroquinone (3 a; 35 % selectivity; 0.18 mg mL?1) directly from 1 a. In the case of 1 b, overoxidation leads to dearomatization and the formation of a valuable p-quinol synthon that can directly serve as an educt for the synthesis of 3 a. Detailed product pattern analysis, substrate docking, and mechanistic considerations support the hypothesis that 1 a binds in an inverted orientation in the active site of P450 BM3 WT, relative to P450 BM3 variant M3, to allow this change in chemoselectivity. This study provides an enzymatic route to key phenolic synthons for α-tocopherols and the first catalytic and mechanistic insights into direct aromatic hydroxylation and dearomatization of trimethylbenzenes with O2.

Selective oxidation of pseudocumene and 2-methylnaphthalene with aqueous hydrogen peroxide catalyzed by γ-Keggin divanadium-substituted polyoxotungstate

Zalomaeva, Olga V.,Evtushok, Vasiliy Yu.,Maksimov, Gennadii M.,Kholdeeva, Oxana A.

, p. 210 - 216 (2015/09/01)

The catalytic performance of a γ-Keggin divanadium-substituted phosphotungstate, (Bu4N)4[γ-PW10O38V2(μ-O)(μ-OH)], has been evaluated in the selective oxidation of 1,2,4-trimethylbenzene (pseudocumene, PC) and 2-methylnaphthalene with the green oxidant, 35% aqueous hydrogen peroxide. Under conditions of H2O2 deficiency ([PC]/[H2O2] = 17-22), PC oxidation proceeded with unusually high chemo- and regioselectivity, producing exclusively 2,4,5-trimethylphenol (2,4,5-TMP) and 2,3,5-TMP in a molar ratio of 7.3/1 and a yield of 73% based on the oxidant. Isomeric 2,3,6-trimethylphenol was found in trace amounts. Under conditions of H2O2 excess ([H2O2]/[PC] = 8), 2,3,5-trimethyl-1,4-benzoquinone (TMBQ, vitamin E key intermediate) formed with 41% selectivity at 41% substrate conversion. Atypical regioselectivity was also found in the oxidation of 2-methylnaphthalene which gave predominantly 6-methyl-1,4-naphthoquinone (6-MNQ) rather than isomeric 2-MNQ. The ratio between the isomers could be altered by varying the catalyst and oxidant amounts.

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