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3-ヒドロキシ-2-ナフトエ酸

3-Hydroxy-2-naphthoic acid

HCID 7104
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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
92-70-6
標準SMILES
O=C(O)c1cc2ccccc2cc1O
InChIKey
ALKYHXVLJMQRLQ-UHFFFAOYSA-N
分子式
C11H8O3
平均分子量
188.18 g/mol
単同位体質量
188.04734412

概要

3-Hydroxy-2-naphthoate is a naphthoic acid.

名称と識別子

優先名称
3-Hydroxy-2-naphthoic acid
IUPAC
3-hydroxynaphthalene-2-carboxylic acid
現地名
3-ヒドロキシ-2-ナフトエ酸
英語名
3-Hydroxy-2-naphthoic acid
分子式
C11H8O3
分子量
188.18

名称と別名

3-Hydroxy-2-naphthoic acid92-70-6BON acidDeveloper BONBONA2-Naphthalenecarboxylic acid, 3-hydroxy-C.I. Developer 202-Naphthoic acid, 3-hydroxy-Miketazol Developer ONSNaphthol B.O.N.B.o.n. acidC.I. Developer 8
名称をさらに表示
3-ヒドロキシ-2-ナフトエ酸3-ヒドロキシ-2-ナグタレンカルボン酸3ヒドロキシ2ナフトエ酸2-ヒドロキシ-3-ナフトエ酸3-ヒドロキシ-2-ナフタレンカルボン酸β-ヒドロキシナフトエ酸3‐ヒドロキシ‐2‐ナフトエ酸ボン酸デベロッパーボン2-ヒドロキシナフタレン-3-カルボン酸3-ヒドロキシナフタレン-2-カルボン酸β-オキシナフトエ酸2-ナフトール-3-カルボン酸ナフトールB.O.N.ミケタゾールデベロッパーONS2-ヒドロキシ-3-ナフタレンカルボン酸3-ヒドロキシ-2-ナフトエ酸標準品BON2-HYDROXY-3-NAPHTHOIC ACID3-hydroxy-2-naphthoicacideveloper8naphtholbondeveloperboncideveloper20
3-Naphthol-2-carboxylic acidNaphthol bonbeta-Oxynaphthoic acid3-HYDROXY-2-NAPHTHALENECARBOXYLIC ACIDDeveloper 82-Hydroxy-3-naphthalenecarboxylic acidCI Developer 20beta-Hydroxynaphthoic acid

データベース識別子

CAS
92-70-6
PubChem CID
7104
DTXSID
DTXSID3026560
ChEMBL
CHEMBL229301
ChEBI
CHEBI:80383
UNII
C7S9D784HX
EC Number
202-180-8
Nikkaji
J4.659K

物性

構造計算による物性補完中

XLogP
2.9
極性表面積
57.5 Ų
水素結合供与体数
2
水素結合受容体数
3
回転可能結合数
1
重原子数
14
形式電荷
0
複雑度
227

実験および物理化学的性質

Chemical ClassesOther Classes -> Naphthoic Acids
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 2 件

log Kow = 3.05

3.4-3.59

Color/Form · 2 件

Very pale yellow crystals

Yellow rhombic leaflets

Solubility · 4 件

Sol in benzene, chloroform, alkaline soln; freely soluble in alcohol and ether

SOL IN TOLUENE

0.1 wt% in water at 25 °C

Solubility in water, g/100ml: 0.047 (very poor)

Flash Point>150 °C c.c.
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point · 3 件

222-223 °C

Lemon to greenish yellow, odorless powder, MP: 218 °C (minimum) /Commercial product, 98% purity/

220 °C

Vapor Pressure · 2 件

0.00000054 [mmHg]

Vapor pressure, Pa at 25 °C: (negligible)

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 · 6 件

This chemical does not meet GHS hazard criteria for 0.5% (1 of 209) of reports.

Danger

H302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P330, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 209 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 4 件

Chemical: 2-Naphthalenecarboxylic acid, 3-hydroxy-

2-Naphthalenecarboxylic acid, 3-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Naphthalenecarboxylic acid, 3-hydroxy- 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: 21-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14175

3-Hydroxy-naphthalene-2-carboxylic acid: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire.
Hazards Summary · 1 件

Emergency medical treatment: irritants; [HSDB] Cause severe damage to eyes in animal studies; Causes skin necrosis after occlusive exposure for 24 hours to the 10-12% solution; Positive for sensitization in a guinea pig maximization test after open epicutaneous challenge. Negative results in patch testing 36 humans volunteers; Evidence of liver and kidney injury in high-dose animal studies; [OECD SIDS: 3-Hydroxy-2-naphthoic acid - 2004] An irritant; [MSDSonline]

TSCA Requirements · 2 件

化学と産業

薬理情報

Metabolism/MetabolitesThe fission product, resulting from the oxidative metabolism of phenanthrene by pseudomonas aeruginosa was converted by enzymes through 2-hydroxy-3-naphthaldehyde into 2-hydroxy-3-naphthoic acid.

用途と製造

Uses · 5 件

Used as a chemical intermediate for dyes and pigments; Has been used as a gallbladder stimulant; [HSDB] Used as intermediate for insecticides and pharmaceuticals; [eChemPortal: SIDSUNEP]

DYES & PIGMENTS

CHEM INT FOR DYES-EG, PIGMENT REDS 57:1, 52:1, 48:2, 48:1

CHEM INT FOR P-(NAPHTHYLAMINO)PHENOL-INT FOR SULFUR DYES

MEDICATION

U.S. Imports · 2 件

(1979) 5.99X10+8 G (PRINCIPAL CUSTOMS DISTRICTS)

(1981) 5.04X10+8 G (PRINCIPAL CUSTOMS DISTRICTS)

U.S. Production · 3 件

2023: 1,000,000 - <8,500,000 lb

(1977) AT LEAST 4.54X10+8 G

(1981) PROBABLY GREATER THAN 2.27X10+6 G

Consumer UsesPigment
Industry UsesPigment
Methods of ManufacturingOBTAINED BY ACTION OF CARBON DIOXIDE ON SODIUM SALT OF BETA-NAPHTHOL UNDER PRESSURE @ 280-290 °C
Formulations/PreparationsBy treating sodium-2-naphtholate with carbon dioxide under pressure.
General Manufacturing Information · 5 件

Synthetic Dye and Pigment Manufacturing

2-Naphthalenecarboxylic acid, 3-hydroxy-: ACTIVE

Absorption of polar bioactive substances from the GI tract is enhanced by including a hydroxyaromatic acid adjuvant in the formulation.

Hydroxyaryl acids incorporated into suppositories to enhance the absorption rate of the rectally delivered drugs. /Hydroxylaryl acids/

関連反応

100 件
反応記録を作成
HRID 27836 の反応式
HRID 27836生成物としてuspto-grants-1980_09
HRID 46947 の反応式
HRID 46947反応物としてuspto-grants-1979_11
HRID 67193 の反応式
HRID 67193生成物としてuspto-grants-1982_08
HRID 67194 の反応式
HRID 67194反応物としてuspto-grants-1982_08
HRID 67195 の反応式
HRID 67195生成物としてuspto-grants-1982_08
HRID 83107 の反応式
HRID 83107反応物としてuspto-grants-2014_09
HRID 108237 の反応式
HRID 108237生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 109724 の反応式
HRID 109724反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
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化合物ノート

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Physical Description · 3 件

Dry Powder; CBI

Pale yellow solid; [Merck Index] Pale yellow crystalline solid; [MSDSonline]

YELLOW CRYSTALS.

Dissociation ConstantspKa = 2.79
Collision Cross Section135.6 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID3026560]

物理化学的性質

融点
218 · 218-221 °C(lit.)
沸点
283.17 °C · 283.17°C (rough estimate)
比重(密度)
1.43 g/cm3 · 1.43 g/cm3 (23℃)
屈折率
1.716 · 1.7160 (estimate)
闪点
150 °C · >150°C
貯蔵温度
Sealed in dry,Room Temperature
溶解性
0.072 g/l · 0.072g/l 実質的に不溶
酸解離定数(Pka)
3.02 · 3.02±0.30(Predicted)
外見
微結晶性粉末
色
黄色からベージュブラウン
由来生物
human blood
水溶解度
実質的に不溶
Merck
14 · 14,4835
BRN
744100 · 744100
Henry's Law Constant
7 · 7.0×103 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C11H8O3/c12-10-6-8-4-2-1-3-7(8)5-9(10)11(13)14/h1-6,12H,(H,13,14)
InChIKey
ALKYHXVLJMQRLQ-UHFFFAOYSA-N
SMILES
OC(=O)c1cc2ccccc2cc1O
CAS データベース
92 · 92-70-6(CAS DataBase Reference)
NISTの化学物質情報
2 · 2-Naphthalenecarboxylic acid, 3-hydroxy-(92-70-6)
EPAの化学物質情報
3 · 3-Hydroxy-2-naphthoic acid (92-70-6)
化学的性質 · 1 件

化学的特性yellow to beige-brown fine crystalline powder. 3 -Hydroxy-2-naphthoic acid [92-70-6], BON acid, C11H8O3, Mr 188.17, mp 222℃, forms pale yellow crystals from aqueous ethanol. Alkaline solutions have a green fluorescence. Aqueous ferric chloride produces a blue color, and warming with CHCl3– NaOH results in a green color. Oxidation with alkaline permanganate gives 2-carboxyphenylglyoxylic acid and then phthalic acid. Dry distillation produces dibenzoxanthone. Bromination gives the 4,7-dibromo derivative; nitration, the 4-nitro derivative; and sulfonation with oleum, the 5,7-disulfonic acid derivative.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3-Hydroxy-2-naphthoic acid is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Chemical DangersDecomposes on heating. This produces irritating fumes. Reacts with strong oxidants.
Hazard Classes and Categories · 3 件

Acute Tox. 4 (99.5%)

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

安全と保護具

Fire FightingUse water spray, foam, dry powder.
First Aid Measures · 4 件

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Seek medical attention if you feel unwell.

Safe StorageSeparated from strong oxidants. Store in an area without drain or sewer access.
Cleanup MethodsWaste water treatment: ion exchange: adsorption on Amberlite XAD-2: 39% retention, influent: 0.6 ppm.
Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 件

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment.

Eye PreventionWear safety goggles.
Fire PreventionNO open flames.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT DISPERSION OF DUST!
Ingestion PreventionDo not eat, drink, or smoke during work.

毒性情報

Ecotoxicity ValuesLC50 Brachydanio rario /(Zebra fish)/ 50-71 mg/L/48-96 hr
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a measured log Kow of 3.05(2) and a regression-derived equation(3), indicates that 3-hydroxy-2-naphthalenecarboxylic acid is expected to have low mobility in soil(SRC). The pKa of 3-hydroxy-2-naphthalenecarboxylic acid is 2.79(4), which indicates that this compound will exist primarily as an anion in moist soil and the mobility of anions is usually much greater than neutral species(5). Volatilization of 3-hydroxy-2-naphthalenecarboxylic acid from moist soil surfaces is not expected to be an important fate process since anions do not volatilize. 3-Hydroxy-2-naphthalenecarboxylic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.4X10-7 mm Hg(SRC), determined from a fragment constant method(6). The results of a single screening study using an activated sludge inoculum(7) suggest that 3-hydroxy-2-naphthalenecarboxylic acid is biodegraded slowly in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a measured log Kow of 3.05(2) and a regression-derived equation(3), indicates that 3-hydroxy-2-naphthalenecarboxylic acid is expected to adsorb to suspended solids and sediment(SRC). The pKa of 3-hydroxy-2-naphthalenecarboxylic acid is 2.79(4), which indicates that this compound will exist primarily as an anion in water and may not absorb to suspended solids and sediments as much as the neutral species (SRC). Volatilization from water surfaces is not expected to be an important environmental fate process since anions do not volatilize(SRC). According to a classification scheme(5), BCF values of 6.7 or lower measured in carp(6), suggest bioconcentration in aquatic organisms is low(SRC). A 1.3% of its theoretical BOD in 2 weeks using an activated sludge inoculum and the Japanese MITI test(6) suggests that 3-hydroxy-2-naphthalenecarboxylic acid is biodegraded slowly in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-hydroxy-2-naphthalenecarboxylic acid, which has an estimated vapor pressure of 5.4X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 3-hydroxy-2-naphthalenecarboxylic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 16 hours(SRC), calculated from its rate constant of 2.4X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase 3-hydroxy-2-naphthalenecarboxylic acid may be removed from the air by wet and dry deposition(SRC). 3-Hydroxy-2-naphthalenecarboxylic acid absorbs light in the environmental UV spectrum(4) and may be capable of undergoing photolysis, but the rate of this reaction is not known(SRC).

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.
Exposure RoutesThe substance can be absorbed into the body through the skin and by ingestion.
Signs and Symptoms · 4 件

Sore throat. Cough.

Redness. Pain.

Redness. Pain. Burns.

Sore throat. Nausea. Vomiting. Diarrhoea.

ICSC Environmental DataThe substance is harmful to aquatic organisms.
Soil Adsorption/Mobility · 1 件

The Koc of 3-hydroxy-2-naphthalenecarboxylic acid is estimated as 1,100(SRC), using a measured log Kow of 3.05(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3-hydroxy-2-naphthalenecarboxylic acid is expected to have low mobility in soil. The pKa of 3-hydroxy-2-naphthalenecarboxylic acid is 2.79(4), indicating that this compound will exist as an anion in moist soils(SRC) and the mobility of anions is usually much greater than neutral species(5).

Artificial Pollution Sources3-Hydroxy-2-naphthalenecarboxylic acid's production and use in dyes and pigments(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 2 件

THE BIODEGRADABILITY OF ORG SUBSTANCES IN WASTEWATER BY ACTIVATED-SLUDGE WAS DETERMINED. BETA-HYDROXYNAPHTHOIC ACID WAS RESISTANT TO DEGRADATION.

3-Hydroxy-2-naphthalenecarboxylic acid, present at 100 mg/l, reached 1.3% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1).

Environmental Bioconcentration · 1 件

The BCF values of 3-hydroxy-2-naphthalenecarboxylic acid at water concentrations of 0.1 and 1.0 mg/l were 6.7 or lower, measured in carp over an 6 week exposure period(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for 3-hydroxy-2-naphthalenecarboxylic acid is estimated as 1.4X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 3-hydroxy-2-naphthalenecarboxylic acid is expected to be essentially nonvolatile from water surfaces(2). Furthermore, 3-hydroxy-2-naphthalenecarboxylic acid is a weak acid with pKa of 2.79(2), indicating that this compound will exist as an anion in the environment, and anions do not volatilize from water or soil surfaces(SRC). 3-Hydroxy-2-naphthalenecarboxylic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.4X10-7 mm Hg(SRC), determined from a fragment constant method(4).

Non-Human Toxicity Excerpts · 3 件

/LABORATORY ANIMALS: Acute Exposure/ ... Irritating to rabbit eyes but not to rabbit skin. /Commercial product, 98% purity/

/LABORATORY ANIMALS: Acute Exposure/ Acute effects on skin: moderate irritant on guinea pig skin, not sensitizer. /from table/

/ALTERNATIVE IN VITRO TESTS/ In rat liver mitochondrial preparations in the absence of phosphate acceptor, uncoupling activities for beta-hydroxynaphthoic acid was greater than that of salicylic acid.

法規制情報

TSCA Requirements · 2 件

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3-Hydroxy-2-naphthoic acid is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

安全データ

wgk
1
tsca
TSCA listed
rtecs
QL1755000
毒性
The acute oral LD50 of 3-Hydroxy-2-naphthoic acid in rats was 823-1040 mg/kg bw.
hs_code
29182910
risk_code
22-36-36/37/38
化審法
(4)-398
安衛法
変異原性物質
hazard_code
Xn,Xi
safety_code
26-37/39
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 3Eye Dam. 1STOT SE 3
ストレージクラス
11 - Combustible Solids
有毒物質データの
92-70-6(Hazardous Substances Data)

Oral formulatons for improved absorption of beta-lactam antibiotics such as penicillins, cephalosporins, etc, comprise hydroxyaryl acids as adjuvants.

応用分野 · 3 件

用途有機合成原料。

用途染料中間体

使用3-Hydroxy-2-naphthoic acid is mainly used as intermediate for the production of dyes and pigments. Further uses are as intermediate for insecticides and pharmaceuticals (ECB, 2000).

調製方法

純化方法Crystallise it from water or acetic acid. The S-benzyisothiuronium salt has m 216-217o (from EtOH). It forms many metal complex salts. [Beilstein 10 H 333, 10 III 1084.]

上流・下流製品情報

上流原料

Double sodium salt水和物炭酸水素ナトリウム2-ナフトール3-ヒドロキシ-2-ナフトエ酸メチル3,3'-(エチレンビスオキシ)ビストルエンエチレン グリコール ジフェニル エーテルベンジルトリメチルアンモニウムクロリドカリウムヒドロキシド

下流製品

7-ブロモ-N-(2-メトキシフェニル)-3-ホスホノオキシ-2-ナフタレンカルボアミド3-ヒドロキシ-2-ナフトアニリドLithol rubilie BK4-[(5-クロロ-4-メチル-2-スルホフェニル)アゾ]-3-ヒドロキシ-2-ナフタレンカルボン酸/カルシウム,(1:1)リソールルビンBCA3-ヒドロキシ-3'-ニトロ-2-ナフトアニリドN-(2,3-ジヒドロ-2-オキソ-1H-ベンゾイミダゾール-5-イル)-3-ヒドロキシ-4-[[2-メトキシ-5-[(フェニルアミノ)カルボニル]フェニル]アゾ]-2-ナフタレンカルボアミド2,3-ジアミノナフタレン3-アミノ-2-ナフトール3-ヒドロキシ-2'-メチル-2-ナフトアニリド6-ヒドロキシ-2-ナフトエ酸6-アセトキシ-2-ナフトエ酸3-メトキシ-2-ナフトエ酸N-(4-メトキシ-2-メチルフェニル)-3-ヒドロキシ-2-ナフタレンカルボアミド3-(アセチルオキシ)-N-(4-クロロフェニル)-2-ナフタレンカルボアミド