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Product Details
Chinese factory supply p-Toluic acid 99-94-5 in stock with high standard
- Molecular Formula:C8H8O2
- Molecular Weight:136.15
- Appearance/Colour:colourless crystals or white crystalline powder
- Vapor Pressure:0.00248mmHg at 25°C
- Melting Point:179 °C
- Refractive Index:1.5120 (estimate)
- Boiling Point:275.3 °C at 760 mmHg
- PKA:4.36(at 25℃)
- Flash Point:124.7 °C
- PSA：37.30000
- Density:1.151 g/cm3
- LogP:1.69320
p-Toluic acid(Cas 99-94-5) Usage
|
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). |
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 Relevant articles
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...
-
Lebedev et al.
, (1972)
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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 ...
An efficient aerobic oxidation for p-xylene to p-toluic acid by unsymmetrical Schiff base manganese(III) complexes with pendant benzo-10-aza-crown ether or morpholino-groups
Li, Jian-Zhang,Yang, Zhu-Zhu,He, Xi-Yang,Zeng, Jun,Qin, Sheng-Ying
, p. 581 - 584 (2010)
Unsymmetrical Schiff base Mn(III) comple...
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 s...
-
Feifer,Welstead
, p. 2567 (1961)
-
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 wer...
A Sustainable Route to a Terephthalic Acid Precursor
Banella, Maria Barbara,Gioia, Claudio,Vannini, Micaela,Colonna, Martino,Celli, Annamaria,Gandini, Alessandro
, p. 942 - 945 (2016)
A new synthetic pathway for the producti...
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 (A...
Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process
Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun
supporting information, p. 2020 - 2024 (2022/03/31)
A visible-light-promoted atomic substitu...
Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate**
Pfennig, Victoria S.,Villella, Romina C.,Nikodemus, Julia,Bolm, Carsten
supporting information, (2022/01/22)
A one-pot, three-step protocol for the p...
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 chemica...
99-94-5 Process route
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106-42-3
para-xylene
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100-21-0
terephthalic acid
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-
99-94-5
p-Toluic acid
| Conditions | Yield |
|---|---|
|
With
N-hydroxyphthalimide; oxygen; nitric acid;
at 110 ℃;
for 6h;
under 760.051 Torr;
Ionic liquid;
|
96% 3% |
|
para-xylene;
With
N-hydroxyphthalimide; cobalt(II) phthalocyanine; μ-oxo[manganese(III) tetraphenylporphine]2; oxygen;
at 120 ℃;
under 3750.38 Torr;
With
N-hydroxyphthalimide; cobalt(II) phthalocyanine; μ-oxo[manganese(III) tetraphenylporphine]2; oxygen; acetic acid;
at 232 ℃;
for 1.5h;
under 16501.7 Torr;
Temperature;
Pressure;
Reagent/catalyst;
|
9.7% 90% |
|
With
chromium(VI) oxide; periodic acid;
In
acetonitrile;
at 20 ℃;
for 1h;
|
86% 6% |
|
With
oxygen;
N-hydroxyphthalimide; cobalt(II) acetate;
In
acetic acid;
at 100 ℃;
for 1h;
under 44475.9 Torr;
Product distribution / selectivity;
|
26% 71% |
|
With
oxygen; acetic acid;
hydrogen bromide; cobalt(II) acetate; manganese(II) acetate;
In
water;
at 200 ℃;
for 0.0833333h;
under 33718.9 - 49647.5 Torr;
Product distribution / selectivity;
Inert atmosphere;
|
70% 7.5% |
|
With
oxygen;
N-hydroxymaleimide; cobalt(II) acetate;
In
acetic acid;
at 60 ℃;
for 1h;
under 44475.9 Torr;
Product distribution / selectivity;
|
32% 65% |
|
With
sodium ortho-iodobenzenesulfonate; Oxone; tetra(n-butyl)ammonium hydrogensulfate;
In
acetonitrile;
at 60 ℃;
for 24h;
|
65% 32% |
|
With
water; ozone;
In
acetonitrile;
for 20h;
Reagent/catalyst;
Irradiation;
|
65% 32% |
|
para-xylene;
With
5,10,15,20-tetraphenyl-21H,23H-porphine cobalt(II); oxygen;
at 200 ℃;
for 0.5h;
under 19502 Torr;
With
5,10,15,20-tetraphenyl-21H,23H-porphine cobalt(II); oxygen; acetic acid;
at 186 ℃;
for 1.4h;
under 18001.8 Torr;
Temperature;
Pressure;
Reagent/catalyst;
|
65.6% 34.3% |
|
With
nitric acid; 1-n-butyl-3-methylimidazolium methanesulfonate;
In
water;
for 144h;
Heating / reflux;
|
61% 8% |
|
With
air;
cobalt(II) bromide;
In
various solvent(s);
at 150 ℃;
for 4h;
under 15001.2 Torr;
Product distribution;
other catalyst, time, temperature, solvent.;
|
52.9% 38.2% |
|
With
anthracene; oxygen; acetic acid;
hydrogen bromide; cobalt(II) acetate; manganese(II) acetate;
In
water;
at 170 ℃;
for 1h;
under 21446.5 Torr;
Product distribution / selectivity;
|
44% 29% |
|
With
dihydrogen peroxide;
hydrogen bromide; copper(ll) bromide;
In
water;
at 380 ℃;
under 187519 Torr;
Product distribution / selectivity;
Condensed phase;
|
16.2% 38% |
|
With
tert.-butylhydroperoxide;
mesoporous chromosilicate (Cr-MCM-41);
In
methanol;
for 20h;
Heating;
|
5% 35% |
|
With
air; silica supported 3<(2-hydroxybenzylidene)aminopropyl>(triethoxy)silane Cr(III);
at 130 ℃;
for 24h;
|
5% 29% |
|
With
dihydrogen peroxide;
hydrogen bromide; copper(ll) bromide;
In
water;
at 380 ℃;
under 187519 Torr;
Product distribution / selectivity;
Condensed phase;
|
20.8% 26.1% |
|
With
nitric acid; 1-n-butyl-3-methylimidazolium methanesulfonate;
In
water;
for 24 - 120h;
Heating / reflux;
|
24% 3% |
|
With
oxygen; acetic acid;
hydrogen bromide; cobalt(II) acetate; manganese(II) acetate;
In
water;
at 170 ℃;
for 1h;
under 21446.5 Torr;
Product distribution / selectivity;
|
24% 22% |
|
With
potassium permanganate;
2,3,5-triphenyl-2H-tetrazolium chloride;
In
water; nitrobenzene;
at 95 ℃;
for 1.25h;
|
27 % Spectr. 27 % Spectr. |
|
With
N-hydroxyphthalimide; oxygen; cobalt acetylacetonate;
In
acetic acid;
at 100 ℃;
for 6h;
|
15 % Turnov. 78 % Turnov. |
|
With
potassium permanganate;
2,3,5-triphenyl-2H-tetrazolium chloride;
In
water; nitrobenzene;
at 95 ℃;
for 1.25h;
|
10 % Spectr. 51 % Spectr. |
|
With
N-hydroxyphthalimide; oxygen; cobalt acetylacetonate;
In
acetic acid;
at 100 ℃;
for 12h;
|
23 % Turnov. 68 % Turnov. |
|
With
oxygen; acetic acid; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione;
cobalt(II) acetate;
at 100 ℃;
under 760 Torr;
Further Variations:;
Reagents;
Product distribution;
|
|
|
With
oxygen;
cobalt(II) acetate; cerium(III) acetate;
In
water;
at 130 ℃;
for 6h;
Product distribution / selectivity;
|
|
|
With
oxygen; acetic acid;
diacetoxy-platinum; tetrakis(acetato)dimolybdenum(II);
In
water;
for 1h;
under 10501.1 Torr;
Product distribution / selectivity;
|
|
|
With
N-hydroxy-1,8-naphthalenedicarboximide; oxygen; cobalt(II) acetate; manganese(II) acetate; acetic acid;
at 99.84 ℃;
for 24h;
under 750.075 Torr;
|
|
|
With
oxygen; acetic acid;
cobalt(II) acetate; manganese(II) acetate;
In
water;
at 120 - 160 ℃;
under 750.075 - 2250.23 Torr;
Product distribution / selectivity;
|
|
|
With
air;
cobalt(II) acetate; manganese(II) acetate;
In
water; acetic acid;
at 128 - 130 ℃;
|
|
|
With
oxygen;
1-hydroxy-pyrrolidine-2,5-dione; cobalt(II) acetate; manganese(II) acetate;
In
water;
at 150 ℃;
for 5h;
under 3750.38 Torr;
Product distribution / selectivity;
|
|
|
With
N-hydroxyphthalimide; oxygen; acetic acid;
at 89.84 ℃;
for 3h;
under 15001.5 Torr;
Autoclave;
|
|
|
With
oxygen; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione; acetone oxime;
at 80 ℃;
for 13h;
Ionic liquid;
|
|
|
With
manganese(IV) oxide; oxygen; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione;
at 80 ℃;
for 15h;
Ionic liquid;
|
|
|
With
5,10,15,20-tetrakis(4-methylphenyl)porphyrinatocopper(II); C36H24MnN8; oxygen; cobalt(II) diacetate tetrahydrate;
at 180 ℃;
under 15001.5 Torr;
Pressure;
Temperature;
Reagent/catalyst;
|
|
|
With
1-hydroxy-pyrrolidine-2,5-dione; oxygen; cobalt(II) diacetate tetrahydrate;
In
acetonitrile;
at 60 ℃;
for 12h;
under 760.051 Torr;
Time;
Green chemistry;
|
|
|
With
tert.-butylhydroperoxide;
In
water;
at 80 ℃;
for 12h;
Sealed tube;
|
|
|
With
ozone;
In
water; acetonitrile;
at 20 ℃;
for 20h;
pH=4.5;
UV-irradiation;
Green chemistry;
|
|
|
With
oxygen; Co(3+)*C9H3O6(3-); 2,6-dihydroxypyrrolo[3,4-f]isoindolo-1,3,5,7(2H,6H)tetrone;
In
acetonitrile;
at 100 ℃;
for 12h;
under 22502.3 Torr;
Temperature;
Autoclave;
|
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622-96-8
4-methylethylbenzene
-
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86561-30-0,19759-40-1
1-(4-methylphenyl)ethyl acetate
-
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100-21-0
terephthalic acid
-
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99-94-5
p-Toluic acid
-
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122-00-9
para-methylacetophenone
| Conditions | Yield |
|---|---|
|
With
oxygen;
cobalt(II) bromide;
In
acetic acid;
at 140 ℃;
for 2.41667h;
under 7500.6 Torr;
Product distribution;
other time, other catalysator;
|
42.7 % Chromat. 26.9 % Chromat. 5.1 % Chromat. 0.8 % Chromat. |
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122-00-9
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-
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-
99-75-2
4-methyl-benzoic acid methyl ester