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m-トルイル酸

3-Methylbenzoic acid

HCID 7418
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
99-04-7
標準SMILES
Cc1cccc(C(=O)O)c1
InChIKey
GPSDUZXPYCFOSQ-UHFFFAOYSA-N
分子式
C8H8O2
平均分子量
136.15 g/mol
単同位体質量
136.05242949

概要

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)

名称と識別子

優先名称
3-Methylbenzoic acid
IUPAC
3-methylbenzoic acid
現地名
m-トルイル酸
英語名
m-Toluic acid
分子式
C8H8O2
分子量
136.15

名称と別名

3-Methylbenzoic acidM-TOLUIC ACID99-04-7m-Toluylic acid3-Toluic acidBenzoic acid, 3-methyl-meta-Toluic acidm-Methylbenzoic acidbeta-Methylbenzoic acidbeta-Bethylbenzoic acidDTXSID10216171UA7K8EEXT
名称をさらに表示
m-トルイル酸3-メチル安息香酸mトルイル酸M-メチル安息香酸3メチル安息香酸M‐トルイル酸3-Methylbenzoicm-toluicm-toluicaciMETA-TOLUATEm-Tlouicacidmeta-toluicacid
NSC-2214DTXCID401617CHEBI:10589RefChem:800396202-723-93-Methyl-Benzoic Acidb-Bethylbenzoate3-methyl-benzoate

データベース識別子

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

物性

構造計算による物性

XLogP
2.4
極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
1
重原子数
10
形式電荷
0
複雑度
131

実験および物理化学的性質

Chemical Classes · 2 件

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 件

1 mmHg at 207 °F (NTP, 1992)

0.00014 [mmHg]

Physical Description · 3 件

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]

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

物理化学的性質

融点
107 · 107-113 °C (lit.)
沸点
263 °C · 263 °C (lit.)
比重(密度)
1.054 g/mL · 1.054 g/mL at 25 °C (lit.)
蒸気圧
0.019 Pa · 0.019Pa at 25℃
屈折率
1.509 · 1.509
闪点
150 °C · 150 °C
貯蔵温度
30 °C · Store below +30°C.
溶解性
アルコールおよびエーテルに可溶。
酸解離定数(Pka)
4.27 · 4.27(at 25℃)
外見
結晶性固体
色
わずかに黄色からベージュがかった黄色
臭い (Odor)
Floral-honey odor
PH
3.69 · 3.69(1 mM solution);3.15(10 mM solution);2.64(100 mM solution);
水溶解度
0.1 g/100 · <0.1 g/100 mL で 19 ºC
比熱容量
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)
安定性
安定。可燃性。強力な酸化剤とは相容れない。
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 データベース
99 · 99-04-7(CAS DataBase Reference)
NISTの化学物質情報
3 · Benzoic acid, 3-methyl-(99-04-7)
EPAの化学物質情報
m-Toluic acid (99-04-7)

化学的性質

化学的特性White to yellowish crystals. Ionization constant 5.3 × 105. Slightly soluble in water; soluble in alcohol and ether. Combustible.

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 4 件

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 件

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]

Reactive GroupAcids, Carboxylic
Reactivity Profile · 1 件

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%)

安全と保護具

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

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 件

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 件

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)

毒性情報

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.

安全データ

wgk
3
tsca
TSCA listed
rtecs
XU1200000
毒性
LD50 orally in Rabbit: 7000 mg/kg
hs_code
29163900
risk_code
22
化審法
(3)-1285
hazard_code
Xn
safety_code
22-24/25-36
自然発火温度
500 °C
Hazard Classifications
Eye Irrit. 2
ストレージクラス
11 - Combustible Solids

化学と産業

用途と製造

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 件

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Benzoic acid, 3-methyl-: ACTIVE

応用分野 · 3 件

説明m-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.

使用m-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.

一般的な説明White to yellowish crystals or mostly yellow flaky solid (with some white flakes). Has a floral-honey odor.

調製方法 · 1 件

純化方法Crystallise the acid from water. [Beilstein 9 IV 1712.] 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 140o (from aqueous EtOH).

上流・下流製品情報

上流原料

1,3-ジベンジル-2-オキソイミダゾリジン-4,5-ジカルボン酸m-キシレン2-ブロモ-3-メチル安息香酸 臭化物α,3-ジメチルベンジルアルコールぎ酸 リチウム 一水和物3-メチルベンジル アルコール

下流製品

3-(ピロリジン-1-イルメチル)安息香酸メチル3-(4-メチルピペラジン-1-イルメチル)安息香酸m-カルボキシベンズアルデヒドMethyl 3-(morpholinomethyl)benzoate ,98%m-ベンゾイルフェニル酢酸3-メチルベンゾフェノン3-(ブロモメチル)安息香酸N,N-ジエチル-m-トルアミド2-アミノ-5-クロロ-3-メチル安息香酸3-メチル-6-ニトロ安息香酸3-メチル-4-ニトロ安息香酸3-メチル安息香酸エチルBenzoic acid, 2,6-diiodo-3-methyl-2-ヨード-5-メチル安息香酸3-メチル-4-ニトロ安息香酸メチル

補足説明

定義ChEBI: 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.

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