4-フルオロアニリン

4-Fluoroaniline

HCID 9731CAS 371-40-4

基本情報

標準SMILES
Nc1ccc(F)cc1
InChIKey
KRZCOLNOCZKSDF-UHFFFAOYSA-N
分子式
C6H6FN
平均分子量
111.12 g/mol
単同位体質量
111.04842741

概要

4-fluoroaniline is a light-colored oily liquid. Mixture of three isomers. Insoluble in water and denser than water. Contact may cause irritation to skin, eyes, and mucous membranes. May be toxic by ingestion. Used to make other chemicals.

名称と識別子

優先名称
4-Fluoroaniline
IUPAC
4-fluoroaniline
現地名
4-フルオロアニリン
英語名
4-Fluoroaniline
分子式
C6H6FN
分子量
111.12

名称と別名

4-FLUOROANILINE371-40-4p-Fluoroaniline4-Fluorobenzenamine1-Amino-4-fluorobenzeneBenzenamine, 4-fluoro-p-FluorophenylamineAniline, p-fluoro-para-FluoroanilineDTXSID9022027CHEBI:28546NSC-579
名称をさらに表示
4-フルオロアニリン1-フルオロ-4-アミノベンゼン4-フルオロフェニルアミンp-フルオロアニリン4-フルオロベンゼンアミン1-アミノ-4-フルオロベンゼン4フルオロアニリン4‐フルオロアニリン4-フルオロアニリン, 0.2 mg/mL in CH2Cl24-フルオロアニリン, 2.0 mg/mL in CH2Cl2NSC 579uoroaniLAKOS 911494-fluoro-anilinp-fluoro-anilin
60HI1G076ZDTXCID602027FluoroanilinesRefChem:99000206-735-54-FluoronanilineAniline, 4-fluoro-4-Fluoranilin

データベース識別子

CAS
371-40-4、87686-42-8
PubChem CID
9731
DTXSID
DTXSID9022027
ChEMBL
CHEMBL32014
ChEBI
CHEBI:28546
UNII
60HI1G076Z
EC Number
206-735-5
Nikkaji
J33.843E

物性

構造計算による物性

XLogP
1.1
極性表面積
26 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
0
重原子数
8

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
PFASPFAS -> Suspected persistent, mobile, toxic (PMT) PFAS or PFAS-like compounds
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
LogP · 2 件

log Kow = 1.15

1.18

Density · 3 件

1.1725 at 68 °F (USCG, 1999) - Denser than water; will sink

1.1725 at 20 °C/4 °C

1.1725 @ 20°C

物理化学的性質

融点
-1.9 °C · -1.9 °C
沸点
187 °C/767 · 187 °C/767 mmHg (lit.)
比重(密度)
1.173 g/mL · 1.173 g/mL at 25 °C (lit.)
屈折率
20 · n20/D 1.539(lit.)
闪点
165 °F · 165 °F
貯蔵温度
2 · 2-8°C

化学的性質

化学的特性4-Fluoroaniline is a light yellow to gold-coloured liquid.It is easy to oxidize and turn red in air.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 0.5% (1 of 204) of reports.

Danger

H302 (98%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 204 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

危険有害性情報

Regulatory Information · 4 件

Chemical: Benzenamine, 4-fluoro-

Benzenamine, 4-fluoro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 4-fluoro- 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: 29-04-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/12126

4-Fluoroaniline: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelPoison
Fire Hazards · 2 件

Special Hazards of Combustion Products: Irritating and toxic hydrogen fluoride and oxides of nitrogen may form in fires. (USCG, 1999)

· Combustible material: may burn but does not ignite readily.

Health Hazards · 2 件

Inhalation or ingestion causes bluish tint to fingernails, lips and ears indicative of cyanosis; headache, drowsiness, and nausea, followed by unconsciousness. Liquid can be absorbed through skin and cause similar symptoms. Contact with eyes causes irritation. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards Summary · 1 件

A mutagen and severe skin and eye irritant; Causes flaccid paralysis and methemoglobinemia in lethal-dose studies of rats; [RTECS] Emergency treatment: Methemoglobinemia; [HSDB] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; May induce methemoglobinemia; Effects in high-dose animal studies include methemoglobinemia; [MSDSonline]

DOT ID and Guide2941 153

安全と保護具

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 件

INHALATION: Remove victim from exposure immediately; if needed, administer oxygen; refer to physician.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 1 件

Suitable extinguishing media: For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Special protective equipment for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

毒性情報

Ecotoxicity ValuesLC50; Species: Pimephales promelas (Fathead Minnow) age 26-34 day juvenile; Conditions: freshwater, flow through, 25 °C, pH 7.8, hardness 45 mg/L CaCO3, alkalinity 42 mg/L CaCO3; Concentration: 16900 ug/L for 96 hr /> or =95% purity/
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 113(SRC), determined from a structure estimation method(2), indicates that 4-fluoroaniline is expected to have high mobility in soil(SRC). The pKa of 4-fluoroaniline is 4.65(3), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. 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). 4-Fluoroaniline has been observed to bind rapidly with soil in herbicide degradation studies(6). Volatilization of 4-fluoroaniline from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.1X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 4-Fluoroaniline is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.75 mm Hg at 20 °C(7). Limited biodegradation data indicate that 4-fluoroaniline is biodegradable(8,9), but its rate and relative environmental importance is not certain(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 113(SRC), determined from a structure estimation method(2), indicates that 4-fluoroaniline is expected to adsorb to suspended solids and sediment(SRC). The pKa of 4-fluoroaniline is 4.65(3), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. Anilines may bind strongly to humus or organic matter due to the high reactivity of the aromatic amino group(4,5), suggesting some adsorption to suspended solids and sediment may occur(SRC). Volatilization from water surfaces is expected(6) based upon an estimated Henry's Law constant of 6.1X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(6), volatilization half-lives for a model river and model lake are 6.4 and 50 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 3(SRC), from its log Kow of 1.15(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 4-Fluoroaniline absorbs at wavelengths >290 nm(8) and, therefore, may be susceptible to direct photolysis(SRC). Aromatic amines are susceptible to photosensitized degradation in natural waters exposed to sunlight due to reaction with OH and RO2 radicals(9); therefore, indirect photolysis may have some environmental importance in natural water(SRC). 4-Fluoroaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-fluoroaniline, which has a vapor pressure of 0.75 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-fluoroaniline 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 11 hours(SRC), calculated from its rate constant of 3.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 4-Fluoroaniline absorbs at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Ecotoxicity Excerpts · 1 件

/OTHER TERRESTRIAL SPECIES/ ... In the present study, earthworms (Eisenia veneta) were exposed to three different model xenobiotics by a standard filter paper contact test, and toxicant-induced biochemical changes were then investigated by characterizing the changes in endogenous metabolites visible in 600-MHz 1H NMR spectra of tissue extracts. The NMR spectral intensities were converted to discrete numerical values and tabulated in order to provide data matrices suitable for multivariate analysis. Principal component analysis showed that changes had occurred in the biochemical profiles relative to the undosed controls. ... The 4-fluoroaniline-treated worms showed a decrease in maltose concentrations, and 3,5-difluoroaniline exerted the same effect as 2-fluoro-4-methylaniline but to a lesser extent. These changes could potentially be used as novel biomarkers of xenobiotic toxicity and could be used to determine the mechanism of action of other toxic chemicals.

Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 4-fluoroaniline can be estimated to be 113(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4-fluoroaniline is expected to have high mobility in soil. The pKa of 4-fluoroaniline is 4.65(4), indicating that this compound is a weak base and will exist predominantly in the non-ionized form in the environment. However, anilines (aromatic amines) 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). In aerobic soil degradation studies, 4-fluoroaniline that was formed as a principal metabolite of herbicide degradation, was observed to bind rapidly to soil(6).

Artificial Pollution Sources · 1 件

4-Fluoroaniline's production and use as an intermediate in the manufacture of herbicides(1) may result in its release to the environment through various waste streams(SRC). 4-Fluoroaniline has been identified as a principal soil degradation product of the herbicides Sniper and Paragon (active ingredient)(2) which will result in its direct release to the environment(SRC).

安全データ

wgk
1
tsca
TSCA listed
rtecs
BY1575000
ridadr
UN 2941
hs_code
29214210
risk_code
22-34-36/38-33-23/24/25

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

The in vitro hydroxylation-defluorination of p-fluoroaniline was carried out by liver microsomes from the rabbit, rat, sheep, cow, pig, man and pigeon, but not by microsomes prepared from trout.

p-Fluoroaniline is defluorinated notably in vivo in rats, clearly evidenced by the increase in urinary fluoride.

Possible methods for monitoring exposure to 2,4-difluoroaniline and 4-fluoroaniline were studied in rats. Wistar rats were given 1.0, 0.25, and 0.13 millimoles per 0.1 kilogram 2,4-difluoroaniline or 4-fluoroaniline. Blood samples were taken at 1 hr before and 1, 2, 4, 6, 8, and 24 hr after dosing. Methemoglobin was calculated from absorbance at 630 nm before and after adding potassium cyanide to lysed blood. Urinary metabolites were isolated as cetylpyridinium salts from rats similarily dosed with 4-fluoroaniline and 2,4,-difluoroaniline. Analysis of urinary metabolites confirmed that these were the o-sulfates of 2-amino-5-aminophenol and 2-amino-3,5-difluorophenol. The excretion of the urinary conjugated aminophenols after oral dosing with these cmpd was rapid and only low concentrations were detected the second day after dosing. About 39% of 4-fluoroanilne and 13% of 2,4-difluoroaniline were accounted by these metabolites.

The regioselectivity and metabolism of monofluoroanilines were studied in-vivo and in-vitro. Male Wistar-rats were administered 0 or 50 mg/kg 2-fluoroaniline, 3-fluoroaniline, or 4-fluoroaniline orally. Urine samples were collected 24 hours later and analyzed for metabolites by fluorine-19 nuclear magnetic resonance spectroscopy. Liver microsomes prepared from male Wistar-rats that had been pretreated with the cytochrome-P-450 (P450) inducers were fortified with P450 and incubated with 0 or 10 millimolar 2-fluoroaniline, 3-fluoroaniline, or 4-fluoroaniline for 10 minutes. The incubates were analyzed for metabolites. Frontier electron densities of occupied and unoccupied orbitals of 2-fluoroaniline, 3-fluoroaniline, and 4-fluoroaniline were calculated by a computerized semiempirical molecular orbital technique. 3-Fluoro-4-acetamidophenylsulfate, 3-fluoro-4-aminophenylsulfate, and 3-fluoro-4-acetamidophenylglucuronide were the major 2-fluoroaniline urinary metabolites. 2-Fluoro-4-acetamidophenylsulfate, 4-fluoro-2-aminophenylsulfate, 2-fluoro-4-aminophenylsulfate, and the fluoride-ion (F-) were the major metabolites of 3-fluoroaniline. 5-Fluoro-2-aminophenylsulfate and fluoride-ion were the major metabolites of 4-fluoroaniline. In-vitro, 3-fluoro-4-aminophenol was the major 2-fluoroaniline metabolite. 3-Fluoroaniline was converted primarily to 4-aminophenol and 4-fluoro-2-aminophenol. 4-Fluoroaniline was converted primarily to 5-fluoro-2-aminophenol and F-. In microsomes from rats pretreated with the P450 inducers, 3-fluoroaniline underwent hydroxylation primarily in the para position, the extent of hydroxylation being similar for all pretreatment conditions. Ortho hydroxylation at the C6 position occurred under all pretreatment conditions but to a much smaller extent. Ortho hydroxylation at the C2 position occurred only in microsomes from rats pretreated with 3MC and isosafrole. Frontier electron densities in the highest occupied molecular orbital (HOMO) and the orbital just below it (HOMO-1) were highest in the C4 position followed by the C6 and C2 positions. /The investigators/ conclude that the regioselectivity in the hydroxylation of 3-fluoroaniline can be explained by higher electron densities in the HOMO and HOMO-1 orbitals of the C4 and C6 carbons and the low density at the C2 position. P450 catalyzed hydroxylation of monofluoroanilines apparently involves electrophilic attack of a charged iron/oxygen species derived from P450 on a specific carbon atom of the aromatic ring.

For more Metabolism/Metabolites (Complete) data for 4-FLUOROANILINE (6 total), please visit the HSDB record page.

用途と製造

Uses · 4 件

Used as an intermediate in the manufacture of herbicides, plant growth regulators, dyes, and para-Fluorophenol; [HSDB]

Intermediate in manufacture of herbicides and plant growth regulators.

Preparation of para-fluorophenol

4-Fluoroaniline is an intermediate for liquid crystal polymers

U.S. Production · 2 件

2023: 78,500 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#4149]

Industry UsesIntermediate
Methods of ManufacturingPrepared by reduction of 1-fluoro-4-nitrobenzene by Raney nickel; ... by sulfurated sodium borohydride.
Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information · 2 件

All Other Basic Organic Chemical Manufacturing

Benzenamine, 4-fluoro-: ACTIVE

応用分野 · 4 件

用途医薬?農薬?染料中間体

用途有機合成原料。

使用4-Fluoroaniline is a degradation product of Ezetimibe (E975000). 4-Fluoroaniline is used as an analytical reagent in the enzymic detection of glucose.

一般的な説明4-fluoroaniline is a light-colored oily liquid. Mixture of three isomers. Insoluble in water and denser than water. Contact may cause irritation to skin, eyes, and mucous membranes. May be toxic by ingestion. Used to make other chemicals. The barriers to inversion and internal rotation of the NH2 group in 4-fluoroaniline has been investigated by far infrared gas spectra.

上流・下流製品情報

下流製品

補足説明 · 1 件

定義ChEBI: 4-fluoroaniline is a primary arylamine that is the derivative of aniline in which the hydrogen at position 4 has been substituted by fluorine. It is used as an intermediate in the manufacture of pharmaceuticals, herbicides and plant growth regulators. It is a primary arylamine and a fluoroaniline.

関連反応

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