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m-Toluylsure

3-Methylbenzoic acid

HCID 7418
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Grundinformationen

CAS
99-04-7
Standard-SMILES
Cc1cccc(C(=O)O)c1
InChIKey
GPSDUZXPYCFOSQ-UHFFFAOYSA-N
Summenformel
C8H8O2
Durchschnittliche Molmasse
136,15 g/mol
Monoisotopische Masse
136,05242949

Überblick

M-toluic acid appears as white to yellowish crystals or mostly yellow flaky solid (with some white flakes). Has a floral-honey odor. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
3-Methylbenzoic acid
IUPAC
3-methylbenzoic acid
Lokaler Name
m-Toluylsure
Englischer Name
m-Toluic acid
Summenformel
C8H8O2
Molmasse
136.15

Namen und Synonyme

3-Methylbenzoic acidM-TOLUIC ACID99-04-7m-Toluylic acid3-Toluic acidBenzoic acid, 3-methyl-meta-Toluic acidm-Methylbenzoic acidbeta-Methylbenzoic acidbeta-Bethylbenzoic acidDTXSID10216171UA7K8EEXT
Weitere Namen anzeigen
3-Methylbenzoicm-toluicm-toluicaciMETA-TOLUATEm-Tlouicacidmeta-toluicacid
NSC-2214DTXCID401617CHEBI:10589RefChem:800396202-723-93-Methyl-Benzoic Acidb-Bethylbenzoate3-methyl-benzoate

Datenbank-Bezeichner

CAS
99-04-7
PubChem CID
7418
DTXSID
DTXSID1021617
ChEMBL
CHEMBL67450
ChEBI
CHEBI:10589
UNII
1UA7K8EEXT
EC Number
202-723-9
Nikkaji
J47.804K

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,4
Polarare Oberfläche (TPSA)
37,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
10
Formalladung
0
Komplexität
131

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Organic Acids

Industrial compound

SpringerMaterials PropertiesBoiling point
LogP2.32
Density1.054 at 234 °F (NTP, 1992) - Denser than water; will sink
Solubilityless than 1 mg/mL at 66 °F (NTP, 1992)
Boiling Point504 °F at 760 mmHg (sublimes) (NTP, 1992)
Melting Point232 to 235 °F (NTP, 1992)
Vapor Pressure · 2 Einträge

1 mmHg at 207 °F (NTP, 1992)

0.00014 [mmHg]

Physical Description · 3 Einträge

M-toluic acid appears as white to yellowish crystals or mostly yellow flaky solid (with some white flakes). Has a floral-honey odor. (NTP, 1992)

Dry Powder

White to yellowish or yellow solid with a sweet floral odor; [CAMEO] Light yellow powder; [Sigma-Aldrich MSDS]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 22.9% (32 of 140) of reports.

Danger

H302 (34.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 140 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Benzoic acid, 3-methyl-

Benzoic acid, 3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 3-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)

REACH registered substance: m-toluic acid (EC: 202-723-9)

3-Methylbenzoic acid: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure may include irritation of the skin and eyes.
Hazards Summary · 1 Eintrag

Causes muscle weakness, respiratory depression, and nausea in oral lethal-dose studies of mice; [RTECS] Not considered a skin irritant; Potential sensitizer; Oral repeated dose study of rats produced changes in hematology and increased relative pituitary weight in males and increased relative and absolute liver weights (with corresponding histopathology) in females at 1,000 mg/mg/day (histological changes also observed in 300 mg/kg/day females); No evidence of reproductive or developmental toxicity; [OECD SIDS: m-Toluic acid - 2003] Harmful by ingestion; [Sigma-Aldrich MSDS] Search for (99-04-7[EC/RN Number]) AND (allergic OR dermatitis OR sensitizer OR sensitization): no results; [PubMed]

Chemie und Industrie

Verwendung und Herstellung

UsesUsed primarily as an intermediate for the insect repellent DEET; About 1% used to make a plastic stabilizer; [OECD SIDS: m-Toluic acid - 2003]
U.S. Production2023: 1,000,000 - <8,500,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 Einträge

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Benzoic acid, 3-methyl-: ACTIVE

Anwendungen · 2 Einträge

Beschreibungm-toluic acid (MTA) , also known as 3-Methylbenzoic acid or m-Toluate, is a benzoic acid derivative having a floral honey odour. Benzoic acids are organic Compounds containing a benzene ring which bears at least one carboxyl group. Benzoic acid occurs naturally in many plants and its name was also derived from a plant source i.e. Gum benzoin. Although it is used as precursor to plasticizers, preservatives such as sodium benzoate, it also has wide application in many pharmaceutical preparations meant for treatment of fungal skin diseases, topical antiseptics, expectorants, analgesics and decongestants. The benzoic acid derivatives are also very useful due to their bacteriostatic and fragrant properties. MTA is used as intermediate in various chemical reactions, MTA is used as a chemical intermediate in manufacturing of insect repellent and plastic stabilizer in the chemical industry. It is also used in the production of various chemicals like 3-carboxybenzaldehyde, 3-benzoylphenylacetic acid, 3-methylbenzophenone, and N,N-diethyl- 3-methylbenzamide etc.. It is a main component of N,N-diethylm-toluamide, commonly known as DEET, which is first insect repellent that can be applied to skin or clothing and provide protection against mosquitoes and other biting insects.

Verwendenm-Toluic acid is used as a reagent in the preparation of hybrid molecules containing oxadiazole and thiadiazole bearing Schiff base moiety as it has antitumor activities.

Vor- und nachgelagerte Produkte

Zugehörige Reaktionen

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Collision Cross Section131.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID1021617]

Physikochemische Eigenschaften

Schmelzpunkt
107 · 107-113 °C (lit.)
Siedepunkt
263 °C · 263 °C (lit.)
Dichte
1.054 g/mL · 1.054 g/mL at 25 °C (lit.)
Dampfdruck
0.019 Pa · 0.019Pa at 25℃
Brechungsindex
1.509 · 1.509
Flammpunkt
150 °C · 150 °C
storage temp.
30 °C · Store below +30°C.
Löslichkeit
Soluble in alcohol and ether.
pka
4.27 · 4.27(at 25℃)
Aggregatzustand
Crystalline Solid
Farbe
Slightly yellow to beige-yellow
Geruch (Odor)
Floral-honey odor
PH
3.69 · 3.69(1 mM solution);3.15(10 mM solution);2.64(100 mM solution);
Wasserlöslichkeit
0.1 g/100 · <0.1 g/100 mL at 19 ºC
Spezifische Wärmekapazität
1.2 J/ · Cp(crystal): 1.2 J/(g·K), at 25℃
Merck
14 · 14,9535
BRN
970526 · 970526
Henry's Law Constant
6.6 · 6.6×100 mol/(m3Pa) at 25℃, Mackay et al. (2006)
Stabilität
Stable. Combustible. Incompatible with strong oxidizing agents.
InChI
1S/C8H8O2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3,(H,9,10)
InChIKey
GPSDUZXPYCFOSQ-UHFFFAOYSA-N
SMILES
Cc1cccc(c1)C(O)=O
LogP
2.37 · 2.37
CAS Datenbank
99 · 99-04-7(CAS DataBase Reference)
NIST chemische Informationen
3 · Benzoic acid, 3-methyl-(99-04-7)
EPA chemische Informationen
m-Toluic acid (99-04-7)
Reactive GroupAcids, Carboxylic
Reactivity Profile · 1 Eintrag

M-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 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 reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. This chemical is incompatible with strong oxidizers. (NTP, 1992)

Air and Water ReactionsFine 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 CategoriesAcute Tox. 4 (34.3%)

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

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 · 1 Eintrag

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) · 1 Eintrag

RECOMMENDED RESPIRATOR: Where the neat test chemical is stored, weighed and diluted, wear an 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)

Toxikologische Informationen

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
29163900
RTECS-Nr.
XU1200000
risk_code
22
Toxizität
LD50 orally in Rabbit: 7000 mg/kg
hazard_code
Xn
safety_code
22-24/25-36
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Eye Irrit. 2
Selbstentzündungstemperatur
500 °C

Vorgelagerte Rohstoffe

1,3-Dibenzyl-2-oxoimidazolidin-4,5-dicarbonsurem-Xylol2-Bromo-3-methylbenzoic acidα-3-DimethylbenzylalkoholLithium formate hydrate3-Methylbenzylalkohol

Nachgelagerte Produkte

Methyl 3-((pyrrolidin-1-yl)methyl)benzoate3-(4-Methylpiperazin-1-ylmethyl)benzoic acid3-FormylbenzoesureMethyl 3-(morpholinomethyl)benzoate ,98%3-Benzoylphenylessigsure3-Methylbenzophenon3-(Bromomethyl)benzoic acidN,N-Diethyl-m-toluamid2-Amino-5-chloro-3-methylbenzoic acid6-Nitro-p-toluylsure4-Nitro-m-toluylsureEthyl-m-toluatBenzoic acid, 2,6-diiodo-3-methyl-2-Iodo-5-methylbenzoic acidMethyl 3-methyl-4-nitrobenzoate

Ergänzende Hinweise

DefinitionChEBI: M-toluic acid is a methylbenzoic acid carrying a methyl substituent at position 3. It has a role as a human xenobiotic metabolite. It is a conjugate acid of a m-toluate.