기본 정보
- 표준 SMILES
Nc1ccc(Cl)c([N+](=O)[O-])c1- InChIKey
FOHHWGVAOVDVLP-UHFFFAOYSA-N- 분자식
- C6H5ClN2O2
- 평균 분자량
- 172.57 g/mol
- 단동위원소 질량
- 172.00395508
개요
intermediate in manufacture of pigments
이름 및 식별자
- 우선 이름
- 4-Chloro-3-nitroaniline
- IUPAC
- 4-chloro-3-nitroaniline
- 현지명
- 4- 클로로 -3- 니트로 아닐린
- 영어명
- 4-Chloro-3-nitroaniline
- 분자식
- C6H5ClN2O2
- 분자량
- 172.57
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
635-22-3- PubChem CID
- 12477
- DTXSID
DTXSID7052319- ChEMBL
CHEMBL3560892- UNII
- B13U77ZL3A
- EC Number
- 211-231-3
- Nikkaji
- J1.714K
물성
구조 계산 물성
- XLogP
- 2.1
- 극성 표면적
- 71.8 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 11
- 형식 전하
- 0
- 복잡도
- 159
실험 및 물리화학적 성질
LogP
log Kow = 2.06
2.06
Color/Form
Yellow to tan powder
Yellow needles or prisms from water; needles from petroleum ether
Solubility
Soluble in ether, chloroform; very soluble in ethanol; slightly soluble in ligroin
Partially sol in hot water
물리화학적 성질
- 녹는점
- 99 · 99-101 °C (lit.)
- 끓는 점
- 200 °C · 200°C (rough estimate)
- 밀도
- 1.561 · 1.5610 (rough estimate)
- 굴절률
- 1.587 · 1.5870 (estimate)
- 저장 조건
- Keep in dark place,Sealed in dry,Room Temperature
- 산도 계수 (pKa)
- 1.87 · 1.87±0.10(Predicted)
- 물리적 상태
- powder to crystal
- 색상
- 흰색에서 노란색, 주황색으로
- BRN
- 1309394 · 1309394
- Henry's Law Constant
- 1.8 · 1.8×103 mol/(m3Pa) at 25℃, HSDB (2015)
- InChI
- InChI=1S/C6H5ClN2O2/c7-5-2-1-4(8)3-6(5)9(10)11/h1-3H,8H2
- InChIKey
- FOHHWGVAOVDVLP-UHFFFAOYSA-N
- SMILES
- C1(N)=CC=C(Cl)C([N+]([O-])=O)=C1
- NIST
- 4 · Benzenamine, 4-chloro-3-nitro-(635-22-3)
- EPA
- 4 · 4-Chloro-3-nitroaniline (635-22-3)
화학적 성질
ochre powder
안전 및 규제
GHS 분류
GHS Classification
Danger
H300 (95.6%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
TSCA Requirements
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importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Benzenamine, 4-chloro-3-nitro- is included on this list. Effective date 10/4/82; Sunset date 10/4/92.
DOT Emergency Guidelines
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Chloronitroanilines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chloronitroanilines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Chloronitroanilines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Chloronitroanilines/
For more DOT Emergency Guidelines (Complete) data for 4-CHLORO-3-NITROANILINE (8 total), please visit the HSDB record page.
Shipment Methods and Regulations
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Shipping Name/ Number DOT/UN/NA/IMO
UN 2237; Chloronitroanilines
IMO 6.1; Chloronitroanilines
안전 및 보호
Fire Fighting Procedures
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.
Disposal Methods
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.
Preventive Measures
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Do not use water.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment.
독성 정보
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 300(SRC), determined from a log Kow of 2.06(2) and a regression-derived equation(3), indicates that 4-chloro-3-nitroaniline is expected to have moderate mobility in soil(SRC). Volatilization of 4-chloro-3-nitroaniline from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.6X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 4-Chloro-3-aniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-4 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2007); however, based on similarly structured 4-chloro-2-nitroaniline which exhibited 0% theoretical BOD using the Japanese MITI test(6), 4-chloro-3-nitroaniline is expected to be resistant to biodegradation in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 300(SRC), determined from a log Kow of 2.06(2) and a regression-derived equation(3), indicates that 4-chloro-3-nitroaniline is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 5.6X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5) According to a classification scheme(6), an estimated BCF of 8(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2007); however, based on similarly structured 4-chloro-2-nitroaniline which exhibited 0% theoretical BOD using the Japanese MITI test(8), 4-chloro-3-nitroaniline is expected to be resistant to biodegradation in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-chloro-3-nitroaniline, which has an estimated vapor pressure of 4.8X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-chloro-3-nitroaniline 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 5.8 days(SRC), calculated from its rate constant of 2.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 4-Chloro-3-nitroaniline does contain chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(3).
Soil Adsorption/Mobility
The Koc of 4-chloro-3-nitroaniline is estimated as 300(SRC), using a log Kow of 2.06(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-chloro-3-nitroaniline is expected to have moderate mobility in soil. However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC). The log Koc of 4-chloro-3-nitroaniline was measured as 2.29 in Yangtze river sediment (37.1% sand, 49.3% silt, 13.6% clay, 1.28% organic carbon, pH 7.44)(6). The log Koc was also measured as 3.53 in modified clay(7). These values give Koc values of 195 and 3,400, respectively.
TSCA Test Submissions
Subchronic toxicity was evaluated in 4 groups of male Sprague-Dawley rats (5/group/dose level) ingesting 4-chloro-3-nitroaniline via the diet at nominal doses of 0, 8.7, 87 or 698 mg/kg/day, (at percentage rates equal to 0, 0.01, 0.1 or 1% respectively) for 14 days. Effects at the 1% dose group included a decrease in food consumption and weight gain, a severe decrease in testes weight, erythrocyte concentration, liver and spleen weight, a slight decrease in kidney weight, and a moderate decrease in blood glucose concentration. There was a severe increase in heinz body count, hemoglobin concentration, and red blood cell count, with a slight increase in blood urea nitrogen concentration. There was also severe degeneration of sperm in the testes and epididymides. Effects at the 0.1% dose level included a slight increase in heinz bodies, and liver weights, and minor anisocytosis, macrocytosis and/or polychromasia were present in 5/5 rats. All other parameters were normal. No compound related effects were seen in the 0.01 and 0% dose groups.
Environmental Biodegradation
AEROBIC: No biodegradation data were found for 4-chloro-3-nitroaniline(SRC< 2007); however based on similarly structured 4-chloro-2-nitroaniline data, 4-chloro-3-nitroaniline is expected to be resistant to biodegradation(SRC). 4-Chloro-2-nitroaniline exhibited 0% theoretical BOD using the Japanese MITI test(1).
Environmental Bioconcentration
An estimated BCF of 8 was calculated in fish for 4-chloro-3-nitroaniline(SRC), using a log Kow of 2.06(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/Soil
The Henry's Law constant for 4-chloro-3-nitroaniline is estimated as 5.6X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-chloro-3-nitroaniline is expected to be essentially nonvolatile from water surfaces(2). 4-Chloro-3-nitroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-4 mm Hg(SRC), determined from a fragment constant method(3).
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ 4-Chloro-3-nitroaniline was given to groups of 20 male and 20 female rats by gavage at doses of 3.6, 18, or 90 mg/kg in a 10% corn oil suspension. Doses were administered 5 days per week for 90 days. The high dose resulted in reduced body weight gain in males, reduced feed consumption and fluctuating feed consumption in both sexes, slight hemolytic anemia with Heinz bodies in both sexes, enlargement of the spleen due to congestion, hemosiderosis, and increased extramedullary hematopoiesis in both sexes, inflammatory changes in the splenic capsules of two females, hemosiderin pigmentation of the liver in both sexes, bone marrow hyperplasia in both sexes, increased liver weight in females, and testicular atrophy. The middle dose produced a fluctuating feed consumption pattern in males, Heinz bodies in both sexes, very slight anemia in females, splenic hemosiderosis in males, slightly increased splenic extramedullary hematopoiesis in females, hemosiderin pigmentation of the liver in males, and possibly increased liver weight in females, and inflammatory changes in the splenic capsule of one male. The low dose produced Heinz bodies in males and possibly females although the Heinz body counts of females were not statistically significant. The primary toxicologic damage produced by 4-chloro-3-nitroaniline is hemolytic or Heinz body anemia and testicular atrophy. Thus the toxicity of 4-chloro-3-nitroaniline is similar to that of other aromatic nitro and amino chemicals.
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of 4-chloro-3-nitroaniline with photochemically-produced hydroxyl radicals has been estimated as 2.7X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-Chloro-3-nitroanline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 4-Chloro-3-nitroaniline does contain chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(2).
규제 정보
TSCA Requirements
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. Benzenamine, 4-chloro-3-nitro- is included on this list. Effective date 10/4/82; Sunset date 10/4/92.
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- BX1750000
- ridadr
- UN 2237 6.1/PG 3
- HS 번호
- 29214210
- risk_code
- 26/27/28-33-51/53
- hazard_code
- T+,N,T
- safety_code
- 28-36/37-45-61-28A
- 포장분류
- III
- 위험 등급
- 6.1
- 위험 참고 사항
- Very Toxic
- Hazard Classifications
- Acute Tox. 2 DermalAcute Tox. 2 InhalationAcute Tox. 4 OralAquatic Chronic 2STOT RE 2
- 스토리지 클래스
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- 유해 물질 데이터
- 635-22-3(Hazardous Substances Data)
화학 및 산업
용도 및 제조
Uses
Used as an intermediate in the manufacture of azo dyes, pharmaceuticals, and other organic compounds; [Hawley]
Intermediate in the manufacture of azo dyes, pharmaceuticals and other organic compounds.
응용 분야
용도Intermediate in the manufacture of azo dyes, pharmaceuticals, and other organic compounds.
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