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3-클로로벤조 산

3-Chlorobenzoic Acid

HCID 447
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인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
535-80-8
표준 SMILES
O=C(O)c1cccc(Cl)c1
InChIKey
LULAYUGMBFYYEX-UHFFFAOYSA-N
분자식
C7H5ClO2
평균 분자량
156.56 g/mol
단동위원소 질량
155.9978071

개요

Crystals or fluffy white powder. (NTP, 1992)

이름 및 식별자

우선 이름
3-Chlorobenzoic Acid
IUPAC
3-chlorobenzoic acid
현지명
3-클로로벤조 산
영어명
3-Chlorobenzoic acid
분자식
C7H5ClO2
분자량
156.57

이름 및 동의어

3-chlorobenzoic acid535-80-8m-chlorobenzoic acidBenzoic acid, 3-chloro-Benzoic acid, m-chloro-Acido m-clorobenzoicoDTXSID902477002UOJ7064KNSC-8443DTXCID904770CHEBI:49410RefChem:93507
이름 더 보기
3-클로로벤조산3-클로로벤조산m-Chlorobenzoic3-chlorobenzoic3-CHLOROBENZOATE3-Chlorbenzoesαure3-ChlorobenzoiAKOS BBS-00003733m-Chlorbenzoesαure3-chloro-benzoicaci
208-618-4800-980-7MCBA3-chloro-benzoic acidMFCD00002491meta-chlorobenzoic acid3-cholro-benzoate3-cholro-benzoic acid

데이터베이스 식별자

CAS
535-80-8
PubChem CID
447
DTXSID
DTXSID9024770
ChEMBL
CHEMBL20563
ChEBI
CHEBI:49410
UNII
02UOJ7064K
EC Number
208-618-4
Nikkaji
J43.164H

물성

구조 계산 물성

XLogP
2.7
극성 표면적
37.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
1
무거운 원자 수
10
형식 전하
0
복잡도
136

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Benzoic Acid Derivatives
SpringerMaterials PropertiesChemical shift
LogP · 2건

2.68

2.51

Density · 2건

1.496 at 77 °F (NTP, 1992) - Denser than water; will sink

1.496 AT 25 °C/4 °C

Color/Form · 2건

CRYSTALS

PRISMS FROM WATER

Solubility · 6건

less than 1 mg/mL at 67.1 °F (NTP, 1992)

SOL IN 2850 PARTS COLD WATER; MORE SOL IN HOT WATER.

SLIGHTLY SOL IN BENZENE, CARBON SULFIDE, PETROLEUM ETHER, CARBON TETRACHLORIDE; MORE SOL IN HOT BENZENE.

SLIGHTLY SOL IN ALCOHOL AND ETHER.

450 mg/l at 15 °C in water.

0.45 mg/mL

Boiling Point · 2건

Sublimes (NTP, 1992)

Sublimes

Melting Point · 3건

316 °F (NTP, 1992)

158 °C

158 °C

Vapor Pressure0.00233 [mmHg]

안전 및 규제

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

GHS 분류

GHS Classification · 5건

This chemical does not meet GHS hazard criteria for 4.3% (3 of 70) of reports.

Warning

H315 (95.7%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 70 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 2건

Chemical: Benzoic acid, 3-chloro-

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

Fire HazardsFlash point data for this compound are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Exposure to this compound may result in eye and skin irritation.
Hazards SummaryA skin irritant; [HSDB] A skin, eye, mucous membrane, and upper respiratory tract irritant; [CAMEO] An irritant; [MSDSonline]
Reactive GroupAcids, Carboxylic
Reactivity ProfileM-CHLOROBENZOIC ACID is incompatible with strong oxidizing agents. (NTP, 1992)
Atmospheric Standards · 1건

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Chlorobenzoic acid is produced, as an intermediate or final product, by process units covered under this subpart. /Chlorobenzoic acid/

화학 및 산업

약리 정보

Metabolism/Metabolites · 4건

YIELDS M-CHLOROBENZOYL-BETA-D-GLUCURONIC ACID IN RABBIT; YIELDS 3-CHLOROCATECHOL IN PSEUDOMONAS; YIELDS 5-CHLORO-1,2-DIHYDRO-1,2-DIHYDROXYBENZOIC ACID IN ALCALIGENES. /FROM TABLE/

YIELDS M-CHLOROHIPPURIC ACID IN RABBIT. /FROM TABLE/

IN PRESENCE OF 500 MG GLUCOSE, BACTERIA FROM SEWAGE TREATMENT PLANT EFFLUENT COMPLETELY DEGRADED 100 MG M-CHLOROBENZOIC ACID/500 ML MEDIUM DURING 7 DAYS. 1ST METAB WAS 3-CHLOROCATECHOL, WHICH WAS CONVERTED INTO 2-HYDROXY-3-CHLOROMUCONIC SEMIALDEHYDE, WHICH WAS IN TURN FURTHER DECOMP.

Plasmid pJP4 permits its host bacterium, strain JMP134, to degrade and utilize as sole sources of carbon and energy 3-chlorobenzoate and 2,4-dichlorophenoxyacetic acid. Mutagenesis of pJ4 by transposons Tn5 and Tn1771 enabled localization of five genes for enzymes involved in these catabolic pathways. Four of the genes, tfdB, tfdC, tfdD, and tfdE, encoded 2,4-dichlorophenol, hydroxylase, dichlorocatechol 1,2-dioxygenase, chloromuconate cycloisomerase, and chlorodienelactone hydrolase, respectively. No function has been assigned to the fifth gene, trans-chlorodiene lactone isomerase, although it may encode a trans-chlorodiene lactone isomerase. Inactivation of genes dichlorocatechol 1,2-dioxygenase, chloromuconate cycloisomerase, and chlorodienelactone hydrolase which encode the transformation of dichlorocatechol to chloromaleylacetic acid, prevented host strain JMP134 from degrading both 3-chlorobenzoate and 2,4-dichlorophenoxyacetic acid, which indicates that the pathways for these two substrates utilize common enzyme for the dissimilation of chlorocatechols. Studies with cloned catabolic genes from pJP4 indicated that whereas all essential steps in the degradation of 2,4-dichlorophenoxyacetic acid are plasmid encoded, the conversion of 3-chlorobenzoate to chlorocatechol is specified by chromosomal genes.

Cellular LocationsMembrane

용도 및 제조

Uses · 5건

Used as a chemical intermediate (dyes, fungicides, and pharmaceuticals) and as a preservative for adhesives and paints; Not commercially produced in the US; [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

CHEM INT, EG, FOR ITS ESTER & PEROXY DERIVS

관련 반응

280건
반응 기록 만들기
HRID 9921 반응식
HRID 9921반응물로uspto-grants-2006_08
HRID 14752 반응식
HRID 14752반응물로uspto-grants-2010_06
HRID 23844 반응식
HRID 23844반응물로uspto-grants-2005_02
HRID 28211 반응식
HRID 28211생성물로uspto-grants-1980_09
HRID 36967 반응식
HRID 36967반응물로uspto-grants-1995_05
HRID 67861 반응식
HRID 67861반응물로uspto-grants-1982_08
HRID 67869 반응식
HRID 67869반응물로uspto-grants-1982_08
HRID 67873 반응식
HRID 67873반응물로uspto-grants-1982_08
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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Physical Description · 3건

Crystals or fluffy white powder. (NTP, 1992)

Solid; [Merck Index] White powder; [MSDSonline]

Solid

Ionization Efficiency · 6건

Negative

0.48

10.5

Agilent XCT

Electrospray ionization

ammonia (10nM)

Dissociation ConstantsPKA 3.82

물리화학적 성질

녹는점
153 · 153-157 °C (lit.)
끓는 점
274 · 274-276°C
밀도
1.496 · 1.496
굴절률
1.5812 · 1.5812 (estimate)
인화점
150 °C · 150 °C
저장 조건
30 °C · Store below +30°C.
용해도
0.45 g/L · 0.45g/L
물리적 상태
결정성 분말
산도 계수 (pKa)
3.82 · 3.82(at 25℃)
색상
흰색에서 베이지색
수용성
19.5 · 19.5&C에서 <0.1g/100mL
Merck
14 · 14,2123
BRN
907218 · 907218
Henry's Law Constant
5.7 · 5.7×101 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
안정성
피부, 눈, 호흡기 자극제.
InChI
1S/C7H5ClO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H,9,10)
InChIKey
LULAYUGMBFYYEX-UHFFFAOYSA-N
SMILES
OC(=O)c1cccc(Cl)c1
NIST
3 · Benzoic acid, 3-chloro-(535-80-8)
EPA
m-Chlorobenzoic acid (535-80-8)

화학적 성질

white to light yellow crystal powder

Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesSkin Irrit. 2 (95.7%)
Skin, Eye, and Respiratory IrritationsSKIN IRRITANT. /FROM TABLE/

안전 및 보호

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

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 · 1건

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) · 1건

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)

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: If released to soil, m-chlorobenzoic acid is expected to biodegrade under both aerobic and anaerobic conditions although there may be a lengthy lag period before this process ensues(1-4). Its estimated Henry's Law constant, 3.88X10-8 atm-cu m/mol(5,SRC), and its estimated vapor pressure, 8.475X10-5 mm Hg at 25 °C(5-7,SRC) indicate that it is not expected to volatilize from either moist or dry soil to the atmosphere(SRC). Estimated soil adsorption coefficients of 152 and 684(6-8,SRC) indicate that m-chlorobenzoic acid will display moderate to high mobility in soil(9). The pKa of m-chlorobenzoic acid, 3.81 at 25 °C(10), indicates that it will be predominately dissociated in moist soil under the typical pH's found in the environment(SRC).

AQUATIC FATE: If released to water, m-chlorobenzoic acid is expected to biodegrade under both aerobic and anaerobic conditions although there may be a lengthy lag period before ths process ensues(1-3). Its estimated Henry's Law constant, 3.88X10-8 atm-cu m/mol(4,SRC), indicate that it is not expected to volatilize from water to the atmosphere(SRC). The half-life for volatilization from a model river 1 m deep, flowing as 1 m/sec with a wind speed of 3 m/sec is 1180 days(5,SRC). Estimated soil adsorption coefficients of 152 and 684(5-7,SRC) indicate that m-chlorobenzoic acid will not adsorb to sediment and suspended organic matter(SRC). The pKa of m-chlorobenzoic acid, 3.81 at 25 °C(8), indicates that it wil be predominately dissociated in water under the typical pH's found in the environment(SRC).

ATMOSPHERIC FATE: If released to the atmosphere, m-chlorobenzoic acid may undergo a gas-phase reaction with photochemically produced hydroxyl radicals. An estimated rate constant of 4.23X10-13 cu cm/molc-sec(1,SRC) translates to a half-life of 38 days(SRC) for this process using an average atmospheric hydroxyl radical concn of 5X10+5 molc/cu cm(1). The water solubility of m-chlorobenzoic acid, 450 mg/L at 25 °C(2), indicates that it may also undergo atmospheric removal by wet deposition processes(SRC).

Effluent Concentrationsm-Chlorobenzoic acid was qualitatively detected in 1 of 46 U.S. industrial effluent samples(1). It was detected in chlorinated municipal sewage effluent at a concn of 0.6 ppb(2).
Soil Adsorption/Mobility · 1건

Estimated soil adsorption coefficients of 152 and 684(1,SRC) obtained from m-chlorobenzoic acid's water solubility, 450 mg/l at 25 °C(2), and octanol/water partition coefficient, 2.68(3), respectivley can be obtained using an appropriate regression equation. These values indicate that it will display moderate to high mobility in soil(4).

Natural Pollution Sourcesm-Chlorobenzoic acid is an anthropogenic compound and it is not known to occur in nature. (SRC)
Artificial Pollution Sources · 1건

m-Chlorobenzoic acid is used as a dye intermediate(1) and may be released to the environment as a fugitive emission during its production, formulation an use(SRC). It may also enter the environment in industrial effluent(2) or as a result of the chlorination of municipal wastewater(3).

Environmental Biodegradation · 5건

CONJUGATIVE PLASMID PAC25, CHARACTERIZED IN A STRAIN OF P PUTIDA, SPECIFIES BIODEGRADATION OF 3-CHLOROBENZOIC ACID BY A MODIFIED ORTHO PATHWAY THAT INVOLVES MALEYLACETATE, BUT NOT BETA-KETOADIPATE, AS AN INTERMEDIATE.

In a survey of standardized tests, m-chlorobenzoic acid was found to biodegrade in the coupled units tests, the Zahn-Wellens test, the MITI test, the Sturm test, the AFNOR test, the OECD screening test and the trickling filter test but not in the closed bottle test(1-4). m-Chlorobenzoic acid was found to biodegrade when inoculated with a primary sewage sludge seed under anaerobic conditions(5). In a screening test, m-chlorobenzoic acid at a concn of 50 ppmC underwent 68% mineralization in 10 weeks after a lag period of 5 weeks and 47% mineralization in 10 weeks after a lag period of 8 weeks in 2 different 10% primary anaerobic digester sludges; it was listed as a compound partially mineralized in 10% of sludge secondary digester and completely mineralized in a 10% sludge from a primary digester(6,7). m-Chlorobenzoic acid displayed a 12 day lag period in a continuous flow through bioreactor using a sewage sludge seed(8).

m-Chlorobenzoic acid underwent 105% theoretical gas production after a 29 day lag period when inoculated with a primary digester sludge under anaerobic conditions, time not stated(1). It underwent 68% and 47% theoretical methane production after 5 and 8 weeks, respectively, when incubated with two different municipal digester seeds under anaerobic conditions(2). Incubation of m-chlorobenzoic acid with organisms isolated from sewage resulted in 16% release of chlorine in 2 days when the inocula was acclimated to benzoic acid, 14% to biphenyl, 23% to sodium citrate, 8.6% to sucrose, and 0.8% to the raw sewage itself(3). Sewage sludge adapted to benzoic acid and 3- or 4- hydroxyl benzoate was found to quantitatively reduce m-chlorobenzoic acid at a concn of 313 mg/L to methane under anaerobic conditions although the unadapted sludge could not(4). m-Chlorobenzoic acid at a concn ranging from 20-800 uM displayed a lag period ranging from 71-170 days when incubated with anaerobic lake sediment(5). It was found to biodegrade when incubated with 5 different anaerobic river sediments after a lag period ranging from 4-6 months(6).

m-Chlorobenzoic acid was listed as a compound amenable to biodegradation under both aerobic(1-2) and anaerobic conditions(2). Pure culture aerobic degradation of m-chlorobenzoic acid produced 3-hydroxybenzoic acid and, subsequently, 2,5-dihyroxybenzoic acid(3). m-Chlorobenzoic acid was shown to undergo 21% degradation in 3 days, 28% in 1 week, 32% in 2 weeks, 38% in 5 weeks, and 59% in 10 weeks using a mixed culture soil sample under aerobic conditions(4). m-Chlorobenzoic acid, at a concn of 100 mg/L underwent oxidation, as measured by oxygen uptake, when inoculated with microorganisms isolated from soil, compost, or mud obtained from a catalytic cracking plant waste lagoon(5). It underwent 100% removal after 96 hrs when incubated with a mixed microbial seed under aerobic conditions(6).

Environmental Bioconcentration · 1건

Estimated bioconcentration factors of 20 and 64(1,SRC) obtained from m-chlorobenzoic acid's water solubility, 450 mg/L at 25 °C(2), and octanol/water partition coefficient, 2.68(3), respectively, can be obtained using an appropriate regression equation. These values indicate that it will not bioconcentrate in fish and aquatic organisms(SRC).

Volatilization from Water/Soil · 1건

An estimated Henry's Law constant of 3.88X10-8 atm-cu m/mol(1,SRC), indicates that m-chlorobenzoic acid will not volatilize from either water or moist soil(SRC). Based on this value, the estimated half-life for volatilization from a model river 1 m deep, flowing at 1 m/sec and a wind speed of 3 m/sec is 1180 days(2,SRC). An estimated vapor pressure of 8.475X10-5 mm Hg at 25 °C(2,SRC) obtained from its water solubility, 450 mg/L at 15 °C(3) and an estimated Henry's Law constant indicates that m-chlorobenzoic acid is not expected to volatilize from dry soil to the atmosphere(SRC).

Non-Human Toxicity Excerpts · 3건

M-CHLOROBENZOIC ACID WAS NOT MUTAGENIC IN EITHER THE SISTER CHROMATID EXCHANGE OR SALMONELLA TYPHIMURIUM HISTIDINE REVERSION MUTAGENESIS ASSAYS.

HOG KIDNEY D-AMINO ACID OXIDASE WAS INHIBITED COMPETITIVELY WITH RESPECT TO THE SUBSTRATE BY 5 META SUBSTITUTED BENZOIC ACIDS.

AROMATIC CARBOXYLATES WERE COMPETITIVE INHIBITORS OF L-AMINO ACID OXIDASE.

Environmental Abiotic Degradation · 1건

An estimated rate constant for the gas-phase reaction of m-chlorobenzoic acid with photochemically produced hydroxyl radicals of 4.23X10-13 cu cm/molc-sec(1,SRC) translates to a half-life of 38 days(SRC) using an average atmospheric hydroxyl radical concn of 5X10+5 molc/cu cm(1).

Probable Routes of Human ExposureOccupational exposure to m-chlorobenzoic acid may occur by dermal contact during its production, formulation or use(SRC). The general population may be exposed by ingestion of contaminated drinking water(1,SRC).
Environmental Water ConcentrationsDRINKING WATER: m-Chlorobenzoic acid has been qualitatively detected in U.S. drinking water supplies(1).

규제 정보

Atmospheric Standards · 1건

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Chlorobenzoic acid is produced, as an intermediate or final product, by process units covered under this subpart. /Chlorobenzoic acid/

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
DG4975990
HS 번호
29163900
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36-37/39
자연 발화 온도
>500 °C
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
535-80-8(Hazardous Substances Data)

Intermediate for the preparation of dyes, fungicides, pharmaceuticals, and other chemicals; preserative for adhesives and paints. /Chlorobenzoic acid/

Used as a dye intermediate.

U.S. Imports(1978) 1.64X10+6 G (UNSPECIFIED ISOMER)
U.S. Production · 2건

(1979) NOT PRODUCED COMMERCIALLY IN USA

(1981) NOT PRODUCED COMMERCIALLY IN USA

Methods of Manufacturing... BY CATALYTIC OXIDN OF 1-CHLORO-3-ETHYLBENZENE; BY CHLORINATION OF BENZOIC ACID; BY THE VON RICHTER REACTION FROM 1-CHLORO-4-NITROBENZENE & ALCOHOLIC POTASSIUM CYANIDE.
General Manufacturing InformationBenzoic acid, 3-chloro-: ACTIVE
응용 분야 · 2건

용도A Pseudomonas species which utilized 3-chlorobenzoic acid as a carbon source converted this compound to 3-hydroxybenzoic and 2, 5-dihydroxybenzoic acids. A methanogenic consortium able to use 3-chlorobenzoic acid as its sole energy and carbon source was enriched from anaerobic sewage sludge. A Pseudomonas putida strain 87 capable of assimilating 3-chlorobenzoic acid as a sole source of carbon and energy (3Cba+) was isolated. coupling of 3-chlorobenzoic acid with phenylboronic acid proceeds at room temperature using 0.5 % Pd and at 100°C using 0.1 % Pd to provide the coupled product in 97 % yeild.

일반 설명Crystals or fluffy white powder.

상·하류 제품 정보

상류 원료

2-Amino-5-chlorobenzoic acid염화은3,5-Dichlorobenzoic acid클로로(3-)티오펜m-Chlorotrichlorotoluene

하류 제품

(S)-3-아미노퀴누클리딘이염산염6-Chloroisobenzofuran-1(3H)-onem-클로로벤조일클로라이드5-Chloro-2-hydroxybenzoic acid2,3-디클로로벤조익산ISOVALERIC ANHYDRIDE3-(3-클로로-페닐)-3-옥소-프로피온산에틸에스테르Methyl 3-chlorobenzoate2,3'-Dichloroacetophenone3-Chlorobenzyl alcohol3-클로로-N,N-디에틸벤자미드

For more Environmental Biodegradation (Complete) data for M-CHLOROBENZOIC ACID (6 total), please visit the HSDB record page.