HuagongsheHuagongshe Chemistry Print Report · For research reference only
P-Toluic Acid
4-METHYLBENZOIC ACID · PTLA · 4-TOLUIC ACID · p-Tolylcarboxylic acid · p-toluic · para-Toluic acid · P-METHYLBENZOIC ACID · BENZOIC ACID, 4-METHYL-
Identifiers & Physical Properties
| CAS No. | 99-94-5 |
|---|---|
| Molecular formula | C8H8O2 |
| Average molar mass | 136.15 g/mol |
| Monoisotopic mass | 136.0524295 g/mol |
| SMILES | Cc1ccc(C(=O)O)cc1 |
| InChIKey | LPNBBFKOUUSUDB-UHFFFAOYSA-N |
| PubChem CID | 7470 |
| ChEMBL | CHEMBL21708 |
| ChEBI | CHEBI:36635 |
| EC No. | 202-803-3 |
| DTXSID | DTXSID6021618 |
Chemical & Physical Properties
| XLogP | 2.3 |
|---|---|
| Topological polar surface area | 37.3 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 123 |
| Chemical classes | Other Classes -> Organic Acids |
| SpringerMaterials Properties | Boiling point |
| LogP (partition coefficient) | 2.272.43 |
| Solubility | less than 1 mg/mL at 66 °F (NTP, 1992)0.34 mg/mL at 25 °C0.3g/l<0.1 g/100 mL at 19 ºC |
| Boiling point | 525 to 527 °F at 760 mmHg (NTP, 1992)274-275 °C (lit.) |
| Melting point | 356 to 360 °F (NTP, 1992)181 °C177-180 °C (lit.) |
| Vapor pressure | 0.0061 [mmHg]0.02 hPa (70 °C) |
| Physical Description | P-toluic acid is a white powder. Sublimes. (NTP, 1992)Dry PowderWhite solid[CAMEO] White to yellow-brown solid[OECD SIDS] White powder[Alfa Aesar MSDS] |
| Density | 1,06 g/cm3 |
| Bulk density | 700kg/m3 |
| Refractive index | 1.5120 (estimate) |
| Flash point | 181°C |
| Storage conditions | Store below +30°C. |
| Physical state | Powder |
| pKa (acidity coefficient) | 4.36(at 25℃) |
| Color | White to slightly yellow-cream |
| pH | 3.73(1 mM solution)3.2(10 mM solution)2.69(100 mM solution) |
| Specific heat capacity | Cp(crystal): 1.24 J/(g·K), at 25℃ |
| Merck | 14,9535 |
| BRN | 507600 |
| Henry's law constant | 2.7×102 mol/(m3Pa) at 25℃, Wang et al. (2017) |
| Stability | Stable. Incompatible with strong oxidizing agents, strong bases. |
| InChI | 1S/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10) |
| InChIKey | LPNBBFKOUUSUDB-UHFFFAOYSA-N |
| SMILES | Cc1ccc(cc1)C(O)=O |
| LogP (partition coefficient) | 2.44 |
| CAS DataBase Reference | 99-94-5(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | A26GBX5SSV |
| NIST Chemistry Reference | Benzoic acid, 4-methyl-(99-94-5) |
| EPA Substance Registry System | Benzoic acid, 4-methyl- (99-94-5) |
| UNSPSC Code | 12352106 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H317 |
| GHS precautionary statements | P261-P272-P280-P302+P352-P333+P313-P362+P364 |
| Hazard symbols | Xn |
| Risk statements (R) | 22 |
| Safety statements (S) | 22-24/25 |
| Water hazard class (WGK) | 1 |
| RTECS number | XU1575000 |
| Autoignition temperature | 570 °C |
| TSCA inventory status | TSCA listed |
| Customs code | 29163900 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Skin Sens. 1 |
| Toxicity | LD50 orally in Rabbit: 400 mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 2.8% (5 of 180) of reports.WarningH315 (10.6%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 180 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Benzoic acid, 4-methyl-Benzoic acid, 4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 20-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/251264-Methylbenzoic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Fire hazards | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Health hazards | SYMPTOMS: Symptoms of exposure to this compound may include skin and eye irritation. |
| Hazards summary | May cause skin and eye irritationHarmful by ingestion, inhalation, and skin absorption[NTP] A skin sensitizer in human volunteers[OECD SIDS] An irritantHarmful by ingestion[Alfa Aesar MSDS] See Methyl 4-methylbenzoate and Phenylacetic acid. |
| Reactive group | Acids, Carboxylic |
| 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 waterthose 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 it 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 reactionslike other acids, they often catalyze (increase the rate of) chemical reactions. This chemical is incompatible with strong oxidizers. It is also incompatible with strong bases. (NTP, 1992). |
| Air and Water Reactions | Fine dust dispensed in air in sufficient concentrations, and in the presence of an ignition source is a potential dust explosion hazard. (NTP, 1992). Insoluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (10.6%) |
| Fire fighting | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992) |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Nonfire spill response | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Adverse effects | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| RAIS Toxicity Values | 0.005PPRTV Current0.05 |
| EPA Provisional Peer-Reviewed Toxicity Values | p-Toluic Acid5 x 10^-3 mg/kg-day5 x 10^-2 mg/kg-dayPDF DocumentInadequate information to assess carcinogenic potential2017 |
| Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06 | 3.20e+024.10e+039.00e+011.00e+032.30e-025.00e-03 |
| Hazard Quotient Level 3 or Cancer Risk Level 1E-04 | 9.50e+021.20e+042.70e+021.00e+035.00e-03Volatile |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | XU1575000 |
| Customs code | 29163900 |
| Toxicity | LD50 orally in Rabbit: 400 mg/kg |
| Risk statements (R) | 22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 22-24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H317 |
| REACH registrations | Active |
| Hazard class | Skin Sens. 1 |
| Autoignition temperature | 570 °C |
| GHS precautionary statements | P261-P272-P280-P302+P352-P333+P313-P362+P364 |
Applications & Uses
Uses
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.
Uses
Intermediates of Liquid Crystals
Uses
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.