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99-94-5 Usage

Uses

Different sources of media describe the Uses of 99-94-5 differently. You can refer to the following data:
1. p-Toluic Acid is used as a reagent in the synthesis of several organic compounds including that of 2-aryl-1,3,4-oxadiazole derivatives which are potential antibacterial agents. Also used in the synthesis of 4-(bromomethyl) benzoic acid.
2. Intermediates of Liquid Crystals

Chemical Properties

colourless crystals or white crystalline powder. Slightly soluble in water; soluble in alcohol and ether. Combustible.

Definition

ChEBI: A methylbenzoic acid in which the methyl substituent is located at position 4.

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 4024, 1972 DOI: 10.1021/ja00766a069The Journal of Organic Chemistry, 37, p. 2564, 1972 DOI: 10.1021/jo00981a010

Reactivity Profile

p-Toluic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in p-Toluic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. p-Toluic acid is incompatible with strong oxidizers. p-Toluic acid is also incompatible with strong bases. .

Fire Hazard

Flash point data for p-Toluic acid are not available; however, p-Toluic acid is probably combustible.

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise the acid from water, water/EtOH (1:1), MeOH/water or *benzene. [Beilstein 9 IV 1724.] Aromatic acid impurities (to <0.05%) can be removed via the (±)--methylbenzylamine salt as described for 2,4-dichlorobenzoic acid [Ley & Yates Organic Process Research & Development 12 120 2008]. The S-benzylisothiuronium salt has m 164o (from aqueous EtOH).

Check Digit Verification of cas no

The CAS Registry Mumber 99-94-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 99-94:
(4*9)+(3*9)+(2*9)+(1*4)=85
85 % 10 = 5
So 99-94-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10)/p-1

99-94-5 Well-known Company Product Price

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  • CAS number
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  • Detail
  • Alfa Aesar

  • (A11506)  p-Toluic acid, 98%   

  • 99-94-5

  • 250g

  • 393.0CNY

  • Detail
  • Alfa Aesar

  • (A11506)  p-Toluic acid, 98%   

  • 99-94-5

  • 1000g

  • 986.0CNY

  • Detail
  • Alfa Aesar

  • (A11506)  p-Toluic acid, 98%   

  • 99-94-5

  • 5000g

  • 4269.0CNY

  • Detail
  • Sigma-Aldrich

  • (41768)  p-Toluicacid  analytical standard

  • 99-94-5

  • 41768-100MG

  • 600.21CNY

  • Detail

99-94-5SDS

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 p-toluic acid

1.2 Other means of identification

Product number -
Other names Benzoic acid, 4-methyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Functional fluids (open systems),Intermediates
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:99-94-5 SDS

99-94-5Synthetic route

4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With oxygen; potassium hydroxide In methanol; water at 50℃; under 760.051 Torr; for 4h;100%
With oxygen; potassium hydroxide In toluene at 100℃; under 760.051 Torr; for 12h;99%
With periodic acid; pyridinium chlorochromate In acetonitrile98%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With phosphate-buffered silica gel supported KMnO4 In cyclohexane at 65℃;100%
With periodic acid; tripropylammonium fluorochromate (VI) In acetonitrile at 0℃; for 1.5h;100%
With [Cu2C6H4(CHNCH2CH2N(CH2C5H4N)2)2](2+)*2ClO4(1-)=C36H38Cu2N8(ClO4)2; oxygen In acetone at -90.16℃;100%
methanol
67-56-1

methanol

1-pyrenylmethyl p-toluate
111077-41-9

1-pyrenylmethyl p-toluate

A

methyl 1-pyrenylmethyl ether
91385-15-8

methyl 1-pyrenylmethyl ether

B

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
for 0.5h; Irradiation;A 95%
B 100%
for 0.5h; Product distribution; Irradiation; recovery of carboxylic acids from their 1-pyrenylmethyl esters;A 95%
B 100%
for 2h; Quantum yield; Irradiation;A n/a
B 80%
carbon monoxide
201230-82-2

carbon monoxide

4-tolyl iodide
624-31-7

4-tolyl iodide

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With potassium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 25℃; under 760 Torr; for 4h;100%
With potassium hydroxide; amphiphilic resin-supported phosphine-palladium; water at 25℃; under 760 Torr; for 12h; Product distribution; Further Variations:; Reagents; hydroxycarbonylation;100%
With dichloro bis(acetonitrile) palladium(II); sodium dodecyl-sulfate; potassium carbonate In water; toluene; butan-1-ol at 50℃; under 760 Torr; for 4h;92%
4-methyl-benzoic acid 4-nitro-benzyloxymethyl ester

4-methyl-benzoic acid 4-nitro-benzyloxymethyl ester

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran Product distribution;100%
p-methylbenzyltri-n-butyl-stannane
74260-32-5

p-methylbenzyltri-n-butyl-stannane

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With C2H2Cl2F3O2V; oxygen In tert-butyl alcohol at 50℃; for 36h;100%
Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 42h; Heating;100%
With [hydroxy(tosyloxy)iodo]benzene; water In dimethyl sulfoxide at 20℃; for 24h;82%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

dimethyl zinc(II)
544-97-8

dimethyl zinc(II)

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane for 2h; Heating;100%
N,4-dimethyl-N-tosylbenzamide

N,4-dimethyl-N-tosylbenzamide

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 85℃; for 12h;100%
para-xylene
106-42-3

para-xylene

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; water at 20℃; for 10h; Inert atmosphere;99%
With N-hydroxy-tetrahydrophthalimide; oxygen; nitric acid at 50℃; under 750.075 - 1500.15 Torr; for 25h; Autoclave; Green chemistry;91.16%
With MoO(O2)(8-quinolinolate)2; dihydrogen peroxide In acetonitrile for 6h; Oxidation; Heating;88%
para-methylacetophenone
122-00-9

para-methylacetophenone

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With oxygen; copper(II) nitrate In acetonitrile at 120℃; under 4500.45 Torr; for 10h;99%
With copper(II) nitrate trihydrate; oxygen In acetonitrile at 120℃; under 4500.45 Torr; for 10h; Autoclave;97%
With sodium hydroxide; sodium bromite; sodium bromide In water for 6h; Ambient temperature;96%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With hydrogen In ethanol at 100℃; under 2250.23 Torr; for 3h; Catalytic behavior; Inert atmosphere;99%
With W-7 Raney-Nickel In ethanol for 5h; Heating;89%
4,4'-dimethylbenzaldazine
4702-76-5, 139030-29-8

4,4'-dimethylbenzaldazine

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 60h; Heating;99%
With [bis(acetoxy)iodo]benzene In tetrahydrofuran at 20℃; for 4h; Green chemistry;72%
carbon dioxide
124-38-9

carbon dioxide

5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane
380481-66-3

5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; 5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane With [Ni(N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(allyl)Cl]; potassium tert-butylate In toluene at 100℃; under 760.051 Torr; for 15h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In water; ethyl acetate; toluene at 20℃;
99%
Stage #1: carbon dioxide; 5,5-dimethyl-2-(4-methylphenyl)-1,3,2-dioxaborinane With potassium tert-butylate; silver(I) acetate; triphenylphosphine In tetrahydrofuran at 70℃; under 15201 Torr; for 16h; Inert atmosphere; Autoclave;
Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;
83%
p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With oxygen; sodium methylate; silver trifluoromethanesulfonate In tetrahydrofuran; methanol at 37℃; under 760.051 Torr; for 12h; Sealed tube;99%
Stage #1: 1,2-di-p-tolylethane-1,2-diol With 2,3,4,5,6-pentamethyliodobenzene; oxygen; isobutyraldehyde In 1,2-dichloro-ethane under 760.051 Torr; for 24h;
Stage #2: With sodium chlorite; 2-methyl-but-2-ene In aq. phosphate buffer; 1,2-dichloro-ethane; tert-butyl alcohol at 25℃; for 14h;
80%
With oxygen In dichloromethane at 20℃; under 760.051 Torr; for 12h; Irradiation;78%
Stage #1: 1,2-di-p-tolylethane-1,2-diol With oxygen; sodium t-butanolate In tetrahydrofuran at 20℃; under 760.051 Torr; for 5h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=1; chemoselective reaction;
60%
para-xylene
106-42-3

para-xylene

A

terephthalic acid
100-21-0

terephthalic acid

B

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

C

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

D

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With hydrogen bromide; oxygen; acetic acid; cobalt(II) acetate; manganese(II) acetate In water at 190℃; under 16501.7 Torr; for 1h; Product distribution / selectivity;A 98.1%
B 0.2%
C 0.4%
D 0.4%
With oxygen; acetic acid; palladium diacetate; antimony(III) acetate In water at 182 - 195℃; under 16501.7 - 20929.4 Torr; for 1 - 1.5h; Product distribution / selectivity;A 50.3%
B 7.2%
C 6.4%
D 6.2%
With hydrogen bromide; oxygen; acetic acid; zirconium oxyacetate; cobalt(II) acetate In water at 190℃; under 16501.7 Torr; for 1h; Product distribution / selectivity;A 4.9%
B 3%
C 1.9%
D 36.9%
formic acid
64-18-6

formic acid

4-tolyl iodide
624-31-7

4-tolyl iodide

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;98%
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere; Sealed tube;82%
4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With iron(III) sulfate; water In toluene at 110℃; for 1.5h; Ionic liquid;97%
With iodine; aluminium In acetonitrile at 80℃; for 18h;96%
With potassium hydroxide In methanol at 35℃; for 0.5h;90%
carbon monoxide
201230-82-2

carbon monoxide

para-bromotoluene
106-38-7

para-bromotoluene

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 1h; Irradiation;97%
With sodium hydroxide; tetrabutylammomium bromide; dicobalt octacarbonyl In water; benzene at 65℃; under 760 Torr; for 1.5h; Irradiation;97%
With palladium diacetate; caesium carbonate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In water; N,N-dimethyl-formamide at 80℃; under 2068.65 Torr; Inert atmosphere;77%
4-Methyl-benzoic acid (E)-3-phenyl-allyl ester

4-Methyl-benzoic acid (E)-3-phenyl-allyl ester

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With Montmorillonite K-10 clay; methoxybenzene for 0.333333h; Dealkylation; Microwave irradiation;97%
With methoxybenzene In toluene for 15h; Heating;10%
4,4'-dimethylbenzoin
1218-89-9

4,4'-dimethylbenzoin

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII); magnesium sulfate In acetonitrile for 3h; Heating;97%
With sodium hypochlorite In acetonitrile at 20℃; for 5h;85%
With diphenyl diselenide; dihydrogen peroxide In water; acetonitrile at 20℃; for 24h;85%
With graphitic carbon nitride; oxygen; acetic acid In water; acetonitrile at 100℃; under 2250.23 Torr; for 16h; Autoclave; Irradiation; Green chemistry;69 %Chromat.
1-(4-methoxyphenyl)-2-(4-methylphenyl)ethanone
57297-25-3

1-(4-methoxyphenyl)-2-(4-methylphenyl)ethanone

A

p-Toluic acid
99-94-5

p-Toluic acid

B

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

Conditions
ConditionsYield
With oxygen; potassium hydroxide at 20℃; Schlenk technique; chemoselective reaction;A 93%
B 97%
1-phenyl-2-p-tolylethanone
2430-99-1

1-phenyl-2-p-tolylethanone

A

p-Toluic acid
99-94-5

p-Toluic acid

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With 5% active carbon-supported ruthenium; water; oxygen; calcium oxide at 100℃; for 24h; Overall yield = 56.7 mg;A 80%
B 97%
C8H12O4

C8H12O4

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 95℃; for 7h; Reagent/catalyst;97%
para-xylene
106-42-3

para-xylene

A

terephthalic acid
100-21-0

terephthalic acid

B

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; nitric acid at 110℃; under 760.051 Torr; for 6h; Ionic liquid;A 96%
B 3%
Stage #1: para-xylene With N-hydroxyphthalimide; cobalt(II) phthalocyanine; μ-oxo[manganese(III) tetraphenylporphine]2; oxygen at 120℃; under 3750.38 Torr;
Stage #2: With N-hydroxyphthalimide; cobalt(II) phthalocyanine; μ-oxo[manganese(III) tetraphenylporphine]2; oxygen; acetic acid at 232℃; under 16501.7 Torr; for 1.5h; Temperature; Pressure; Reagent/catalyst;
A 90%
B 9.7%
With chromium(VI) oxide; periodic acid In acetonitrile at 20℃; for 1h;A 6%
B 86%
4-Methylbenzyl chloride
104-82-5

4-Methylbenzyl chloride

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With sodium hydroxide In water; tert-butyl alcohol at 70℃; Ni-anode, 16 mA/cm2;96%
With 4 Angstroem MS; methyl tri-n-octyl ammonium hydrogen sulfate; sodium tungstate at 90℃; for 18h;68%
p-tolualdehyde p-toluenesulfonylhydrazone
40739-81-9

p-tolualdehyde p-toluenesulfonylhydrazone

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 18h; Heating;96%
tert-butyl 4-methylbenzoate
13756-42-8

tert-butyl 4-methylbenzoate

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With aluminium(III) iodide In acetonitrile at 80℃; for 18h;96%
With 1,1,3,3-Tetramethyldisiloxane; pyrographite; palladium dichloride In 1,2-dimethoxyethane at 25 - 40℃; for 6h;95%
With toluene-4-sulfonic acid for 0.0666667h; microwave irradiation;93%
With (μ3,η2,η3,η5-acenaphthylene)Ru3(CO)7; Dimethylphenylsilane In 1,2-dimethoxyethane at 40℃; for 7h; Inert atmosphere;93%
With high-silica Hβ-75 zeolite In water at 130℃; for 24h; Reagent/catalyst;88%
methyl 3-(4-methylphenyl)-3-oxopropanedithioate
83392-35-2

methyl 3-(4-methylphenyl)-3-oxopropanedithioate

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 100℃; for 10h; Reflux; chemoselective reaction;96%
N-methoxy-4-methylbenzamide
25563-06-8

N-methoxy-4-methylbenzamide

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
With tert.-butylnitrite; water at 29℃; for 0.583333h;96%
methanol
67-56-1

methanol

p-Toluic acid
99-94-5

p-Toluic acid

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With sulfuric acid for 4h; Reflux;100%
With sulfuric acid Fischer-Speier esterification method; Reflux;100%
p-Toluic acid
99-94-5

p-Toluic acid

4-bromomethylbenzoic Acid
6232-88-8

4-bromomethylbenzoic Acid

Conditions
ConditionsYield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 6h; Reflux;100%
With sodium bromate; sodium hydrogensulfite In water; ethyl acetate90%
With dihydrogen peroxide; bromine In dichloromethane; water for 4h; Reflux;87%
p-Toluic acid
99-94-5

p-Toluic acid

4-methyl-3-sulfobenzoic acid
62454-72-2

4-methyl-3-sulfobenzoic acid

Conditions
ConditionsYield
With chlorosulfonic acid at 90℃; for 4h;100%
With sulfuric acid at 160 - 170℃; for 4h;71%
With sulfuric acid at 150 - 160℃;
With sulfuric acid at 150℃;
With sulfur trioxide
p-Toluic acid
99-94-5

p-Toluic acid

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Reflux;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 35℃; for 1h;100%
Stage #1: p-Toluic acid With N,N-dimethyl-formamide In dichloromethane at 0℃; for 0.0833333h;
Stage #2: With oxalyl dichloride In dichloromethane at 20℃; for 12h;
100%
p-Toluic acid
99-94-5

p-Toluic acid

2,4,6-trimethylaniline
88-05-1

2,4,6-trimethylaniline

N-(2,4,6-trimethylphenyl)-4-methylbenzamide
86489-65-8

N-(2,4,6-trimethylphenyl)-4-methylbenzamide

Conditions
ConditionsYield
With diphosphorus tetraiodide In tetrachloromethane; dichloromethane Heating;100%
2,2'-dimethoxy-1,1'-binaphthyl
75685-01-7

2,2'-dimethoxy-1,1'-binaphthyl

p-Toluic acid
99-94-5

p-Toluic acid

6,6'-bis(4-methylbenzoyl)-2,2'-dimethoxy-1,1'-binaphthyl

6,6'-bis(4-methylbenzoyl)-2,2'-dimethoxy-1,1'-binaphthyl

Conditions
ConditionsYield
With methanesulfonic acid; phosphorus pentoxide at 60℃; for 24h; Friedel-Crafts acylation;100%
p-Toluic acid
99-94-5

p-Toluic acid

(2S)-2-[(1,1-dimethylethoxycarbonyl)amino]-3-[(4-methylbenzoyl)amino]propionic acid benzyl ester
847495-03-8

(2S)-2-[(1,1-dimethylethoxycarbonyl)amino]-3-[(4-methylbenzoyl)amino]propionic acid benzyl ester

Conditions
ConditionsYield
Stage #1: 3-amino-(2S)-[(1,1-dimethylethoxycarbonyl)amino]-propionic acid benzyl ester With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In DMF (N,N-dimethyl-formamide) at 20℃; for 0.166667h;
Stage #2: p-Toluic acid With 4-methyl-morpholine In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 3h;
100%
Stage #1: 3-amino-(2S)-[(1,1-dimethylethoxycarbonyl)amino]-propionic acid benzyl ester With N,N,N',N'-tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: p-Toluic acid With 4-methyl-morpholine In N,N-dimethyl-formamide at 0 - 20℃; for 3h;
100%
p-Toluic acid
99-94-5

p-Toluic acid

methyl iodide
74-88-4

methyl iodide

4-methyl-benzoic acid methyl ester
99-75-2

4-methyl-benzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h;
With N'',N'''''-1,8-naphthalenediyl bis[N,N,N',N'-tetramethyl]guanidine In N,N-dimethyl-formamide at 20℃; Kinetics;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere; Sealed tube;
n-heptan1ol
111-70-6

n-heptan1ol

p-Toluic acid
99-94-5

p-Toluic acid

1-heptyl 4-methylbenzoate

1-heptyl 4-methylbenzoate

Conditions
ConditionsYield
With Candida antarctica lipase B immobilised in a macroporous DVB crosslinked polymer (Novozym 435) In cyclohexane at 80℃; for 24h; Enzymatic reaction;100%
With 25 wtpercent H3PO4/ZrO2-TiO2 at 130℃; for 1.75h; Neat (no solvent); chemoselective reaction;80%
4-benzylpyperidine
31252-42-3

4-benzylpyperidine

p-Toluic acid
99-94-5

p-Toluic acid

(4-benzylpiperidin-1-yl)(p-tolyl)methanone

(4-benzylpiperidin-1-yl)(p-tolyl)methanone

Conditions
ConditionsYield
Stage #1: p-Toluic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 20℃; for 0.166667h;
Stage #2: 4-benzylpyperidine at 20℃; for 1h;
100%
tetramethyl ammoniumhydroxide
75-59-2

tetramethyl ammoniumhydroxide

p-Toluic acid
99-94-5

p-Toluic acid

tetramethyl-ammonium; 4-methyl-benzoate

tetramethyl-ammonium; 4-methyl-benzoate

Conditions
ConditionsYield
With water In ethanol at 0 - 20℃; for 0.0833333h;100%
p-Toluic acid
99-94-5

p-Toluic acid

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
With ammonium acetate; water; hydrogen bromide; oxygen; manganese(II) acetate; cobalt(II) diacetate tetrahydrate; 1-n-butyl-3-methylimidazolim bromide; acetic acid; 3-butyl-1-methylimidazolium acetate at 215℃; under 30753.1 Torr; for 3h; Inert atmosphere;99.1%
With ammonium acetate; water; hydrogen bromide; oxygen; manganese(II) acetate; cobalt(II) diacetate tetrahydrate; 1-n-butyl-3-methylimidazolim bromide; acetic acid; 3-butyl-1-methylimidazolium acetate at 215℃; under 30753.1 Torr; for 3h; Inert atmosphere;99.1%
With oxovanadium(IV) sulfate; hydrogen bromide; oxygen; acetic acid In water at 100℃; under 750.075 Torr; for 20h;97%
p-Toluic acid
99-94-5

p-Toluic acid

benzylamine
100-46-9

benzylamine

N-benzyl-4-methylbenzamide
5436-83-9

N-benzyl-4-methylbenzamide

Conditions
ConditionsYield
With borane-ammonia complex In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux;99%
With Bromotrichloromethane; 4-(diphenylphosphino)-benzyltrimethylammonium bromide; triethylamine In tetrahydrofuran at 60℃; for 6h; Inert atmosphere;98%
Stage #1: p-Toluic acid With N-chlorobenzotriazole; triphenylphosphine In dichloromethane for 0.25h;
Stage #2: benzylamine With triethylamine In dichloromethane at 20℃; for 0.75h;
95%
p-cresol
106-44-5

p-cresol

p-Toluic acid
99-94-5

p-Toluic acid

4-methylphenyl 4-methylbenzoate
15024-08-5

4-methylphenyl 4-methylbenzoate

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran at 65℃; for 16h; Product distribution; Further Variations:; Solvents; Mitsunobu reaction;99%
With trifluoromethylsulfonic anhydride; triethylamine; Triphenylphosphine oxide In 1,2-dichloro-ethane at 25℃; for 0.25h;88%
p-Toluic acid
99-94-5

p-Toluic acid

aniline
62-53-3

aniline

4-methyl-N-phenylbenzamide
6833-18-7

4-methyl-N-phenylbenzamide

Conditions
ConditionsYield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;99%
Stage #1: p-Toluic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 20℃; for 0.166667h;
Stage #2: aniline at 20℃; for 1h;
97%
With (3-{[(cyclohexylimino)methylidene]amino}propyl)oxy linked polystyrene resin In dichloromethane; N,N-dimethyl-formamide for 0.0833333h; Flow reactor;96%
p-Toluic acid
99-94-5

p-Toluic acid

<α,α-2H2>-4-methylbenzyl alcohol
40662-66-6

<α,α-2H2>-4-methylbenzyl alcohol

Conditions
ConditionsYield
With lithium aluminium deuteride In tetrahydrofuran for 24h; Heating;99%
With lithium aluminium deuteride In diethyl ether at 20℃; for 3h;90%
p-Toluic acid
99-94-5

p-Toluic acid

p-toluic hydrazide
3619-22-5

p-toluic hydrazide

Conditions
ConditionsYield
Stage #1: p-Toluic acid With sulfuric acid In ethanol for 6h; Reflux;
Stage #2: With hydrazine hydrate; sodium hydrogencarbonate; acetic acid Reflux;
99%
With acetic acid; acetic acid hydrazide for 0.1h; Microwave irradiation;85%
With hydrazine hydrate for 0.0472222h; Microwave irradiation;85%

99-94-5Relevant articles and documents

Synthesis, O2-binding ability and catalytic oxidation performance of cobalt(II) complexes with dihydroxamic acid functionalized N-pivot lariat ethers

Wei, Xing-Yue,Wang, Xing-Min,Li, Ning,Qin, Sheng-Ying

, p. 100 - 102 (2015)

Novel Co(II) complexes with dihydroxamic acids functionalized N-pivot lariat ether CoL1-CoL4 were synthesized and characterized. Their oxygenation constants (ln KO2) and thermodynamic parameters (ΔH°, ΔS°) were measured. And their catalytic performance in oxidation of p-xylene to p-toluic acid (PTA) was investigated. The enhancement of O2-binding and catalytic oxidation activity by the oxa aza crown ether ring of the cobalt complexes were discussed.

Correlation of Intermolecular Acyl Transfer Reactivity with Noncovalent Lattice Interactions in Molecular Crystals: Toward Prediction of Reactivity of Organic Molecules in the Solid State

Krishnaswamy, Shobhana,Shashidhar, Mysore S.

, p. 3952 - 3959 (2018)

Intermolecular acyl transfer reactivity in several molecular crystals was studied, and the outcome of the reactivity was analyzed in the light of structural information obtained from the crystals of the reactants. Minor changes in the molecular structure resulted in significant variations in the noncovalent interactions and packing of molecules in the crystal lattice, which drastically affected the facility of the intermolecular acyl transfer reactivity in these crystals. Analysis of the reactivity vs crystal structure data revealed dependence of the reactivity on electrophile···nucleophile interactions and C-H···π interactions between the reacting molecules. The presence of these noncovalent interactions augmented the acyl transfer reactivity, while their absence hindered the reactivity of the molecules in the crystal. The validity of these correlations allows the prediction of intermolecular acyl transfer reactivity in crystals and co-crystals of unknown reactivity. This crystal structure-reactivity correlation parallels the molecular structure-reactivity correlation in solution-state reactions, widely accepted as organic functional group transformations, and sets the stage for the development of a similar approach for reactions in the solid state.

Ordered mesoporous V2O5/WO3 composite catalysts for efficient oxidation of aryl alcohols

Skliri, Euaggelia,Lykakis, Ioannis N.,Armatas, Gerasimos S.

, p. 46170 - 46178 (2014)

Multicomponent mesoporous metal oxides show promise in the area of heterogeneous catalysis due to the synergetic interactions between the framework components and the high internal surface area. In this study, we present the synthesis of ordered mesoporous tungsten(vi) oxide-vanadium oxide (V2O5) nanocomposite frameworks via a two-step wet chemical deposition and nanocasting process and demonstrate that they exhibit high catalytic activity and stability for the oxidation of aryl alcohols, using tert-butyl hydroperoxide (t-BuOOH) as oxidant. X-ray diffraction, transmission electron microscopy and nitrogen porosimetry results indicate that the template-free materials possess a 3D mesoscopic structure of discernible domains of parallel-arranged nanorods and have an internal pore surface with narrow mesopores. The chemical composition and molecular structure of the mesoporous matrix were determined with elemental X-ray microanalysis (EDS), diffuse reflectance ultraviolet-visible (UV-vis) and Raman spectroscopy. Our catalytic results indicate that a small addition of V2O5 into the lattice of WO3 has a beneficial effect on the catalytic performance. Thus, the 4% V2O5-loaded WO3 catalyst shows a large improvement in the oxidation of various para-substituted aryl alcohols with respect to the pure mesoporous WO3, giving good-to-high yields (ca. 80-100%) of the target products within 1-4 h reaction time.

Effects of ligand composition on the oxidative carbonylation of toluene to toluic acid catalyzed by Rh(III) complexes

Zakzeski, Joseph,Behn, Andrew,Head-Gordon, Martin,Bell, Alexis T.

, p. 11098 - 11105 (2009)

Experimental and theoretical studies were conducted to investigate the influence of anionic ligands (e.g., CF3COO-, CH 3SO3-) on the catalytic activity and selectivity of Rh(III) in the oxidative carb

Gram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading

Chen, Cheng,Cheng, Hua,Verpoort, Francis,Wang, Zhi-Qin,Wu, Zhe,Yuan, Ye,Zheng, Zhong-Hui

, (2021/12/13)

Acceptorless dehydrogenative coupling (ADC) of alcohols and water/hydroxides is an emergent and graceful approach to produce carboxylic acids. Therefore, it is of high demand to develop active and practical catalysts/catalytic systems for this attractive transformation. Herein, we designed and fabricated a series of cyclometallated N-heterocyclic carbene-Ru (NHC-Ru) complexes via ligand tuning of [Ru-1], the superior complex in our previous work. Gratifyingly, gram-scale synthesis of carboxylic acids was efficiently enabled at an ultralow Ru loading (62.5 ppm) in open air. Moreover, effects of distinct ancillary NHC ligands and other parameters on this catalytic process were thoroughly studied, while further systematic studies were carried out to provide rationales for the activity trend of [Ru-1]-[Ru-7]. Finally, determination of quantitative green metrics illustrated that the present work exhibited superiority over representative literature reports. Hopefully, this study could provide valuable input for researchers who are engaging in metal-catalyzed ADC reactions.

One-step solvent-free aerobic oxidation of aliphatic alcohols to esters using a tandem Sc-Ru?MOF catalyst

Feng, Tingkai,Li, Conger,Li, Tao,Zhang, Songwei

supporting information, p. 1474 - 1480 (2022/03/08)

Esters are an important class of chemicals in industry. Traditionally, ester production is a multi-step process involving the use of corrosive acids or acid derivatives (e.g. acid chloride, anhydride, etc.). Therefore, the development of a green synthetic protocol is highly desirable. This work reports the development of a metal-organic framework (MOF) supported tandem catalyst that can achieve direct alcohol to ester conversion (DAEC) using oxygen as the sole oxidizing agent under strictly solvent-free conditions. By incorporating Ru nanoparticles (NPs) along with a homogeneous Lewis acid catalyst, scandium triflate, into the nanocavities of a Zr MOF, MOF-808, the compound catalyst, Sc-Ru?MOF-808, can achieve aliphatic alcohol conversion up to 92% with ester selectivity up to 91%. A mechanistic study reveals a unique “via acetal” pathway in which the alcohol is first oxidized on Ru NPs and rapidly converted to an acetal on Sc(iii) sites. Then, the acetal slowly decomposes to release an aldehyde in a controlled manner for subsequent oxidation and esterification to the ester product. To the best of our knowledge, this is the first example of DAEC of aliphatic alcohols under solvent-free conditions with high conversion and ester selectivity.

Cleavage of Carboxylic Esters by Aluminum and Iodine

Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan

, p. 4254 - 4261 (2021/03/09)

A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.

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