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β-옥시나프토에산

3-Hydroxy-2-naphthoic acid

HCID 7104
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
92-70-6
표준 SMILES
O=C(O)c1cc2ccccc2cc1O
InChIKey
ALKYHXVLJMQRLQ-UHFFFAOYSA-N
분자식
C11H8O3
평균 분자량
188.18 g/mol
단동위원소 질량
188.04734412

개요

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

이름 및 식별자

우선 이름
3-Hydroxy-2-naphthoic acid
IUPAC
3-hydroxynaphthalene-2-carboxylic acid
현지명
β-옥시나프토에산
영어명
3-Hydroxy-2-naphthoic acid
분자식
C11H8O3
분자량
188.18

이름 및 동의어

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
이름 더 보기
3-하이드록시-2-나프토산3-히드록시-2-나프토산β-옥시나프토에산3-하이드록시-2-나프토익산3-하이드록시-2-나프토산2-하이드록시-3-나프토익산2-하이드록시-3-카르복시나프탈렌베타-옥시나프토익산베타-하이드록시나프토익산BON2-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

데이터베이스 식별자

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

물성

구조 계산 물성보충 중

XLogP
2.9
극성 표면적
57.5 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
3
회전 가능 결합 수
1
무거운 원자 수
14
형식 전하
0
복잡도
227

실험 및 물리화학적 성질

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

log Kow = 3.05

3.4-3.59

Color/Form · 2건

Very pale yellow crystals

Yellow rhombic leaflets

Solubility · 4건

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 · 3건

222-223 °C

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

220 °C

Vapor Pressure · 2건

0.00000054 [mmHg]

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

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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

유해성 정보

Regulatory Information · 4건

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 · 1건

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 · 2건

화학 및 산업

약리 정보

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.

용도 및 제조

Uses · 5건

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 · 2건

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

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

U.S. Production · 3건

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 · 5건

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/

관련 반응

100건
반응 기록 만들기
HRID 27836 반응식
HRID 27836생성물로uspto-grants-1980_09
HRID 46947 반응식
HRID 46947반응물로uspto-grants-1979_11
HRID 67193 반응식
HRID 67193생성물로uspto-grants-1982_08
HRID 67194 반응식
HRID 67194반응물로uspto-grants-1982_08
HRID 67195 반응식
HRID 67195생성물로uspto-grants-1982_08
HRID 83107 반응식
HRID 83107반응물로uspto-grants-2014_09
HRID 108237 반응식
HRID 108237생성물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 109724 반응식
HRID 109724반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
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Physical Description · 3건

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]

물리화학적 성질

녹는점
218 · 218-221 °C(lit.)
끓는 점
283.17 °C · 283.17°C (rough estimate)
밀도
1.43 g/cm3 · 1.43 g/cm3 (23℃)
굴절률
1.716 · 1.7160 (estimate)
인화점
150 °C · >150°C
저장 조건
Sealed in dry,Room Temperature
용해도
0.072 g/l · 0.072g/l 거의 불용성
산도 계수 (pKa)
3.02 · 3.02±0.30(Predicted)
물리적 상태
미세 결정성 분말
색상
노란색에서 베이지색 갈색
생물학적 소스
human blood
수용성
실질적으로 불용성
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
NIST
2 · 2-Naphthalenecarboxylic acid, 3-hydroxy-(92-70-6)
EPA
3 · 3-Hydroxy-2-naphthoic acid (92-70-6)
화학적 성질 · 1건

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 · 3건

Acute Tox. 4 (99.5%)

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

안전 및 보호

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

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 · 1건

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 · 1건

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.

독성 정보

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

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 · 4건

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 · 1건

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 · 2건

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 · 1건

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 · 1건

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 · 3건

/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.

규제 정보

TSCA Requirements · 2건

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.

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
QL1755000
독성
The acute oral LD50 of 3-Hydroxy-2-naphthoic acid in rats was 823-1040 mg/kg bw.
HS 번호
29182910
risk_code
22-36-36/37/38
hazard_code
Xn,Xi
safety_code
26-37/39
기존화학 물질
KE-20709
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 3Eye Dam. 1STOT SE 3
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
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.

응용 분야

용도3-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).

상·하류 제품 정보

상류 원료

Double sodium salt물중탄산나트륨(중조)2-나프톨Methyl 3-hydroxy-2-naphthoate1,2-비스(3-메틸페녹시)에탄1,2-디페녹시에탄염화트리메틸벤질암모늄수산화칼륨

하류 제품

Naphthol as-bi phosphate나프톨 AS (R)Lithol rubilie BKC.I. 색소 적색 48/2C.I. 색소 적색 57 칼슘 염3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamidePigment Red 1762,3-나프탈렌디아민3-Amino-2-naphthol나프톨 AS-D6-히드록시-2-나프토산6-아세톡시-2-나프토산3-METHOXY-2-NAPHTHOIC산Naphthol as-lt나프톨AS-E아세테이트