化工社化工社 化学情報印刷レポート · 研究参考用
フタルイミド
フタルイミド · o-フタルイミド · イソインドリ-1,3-ジオン · 1,3-ジヒドロ-2H-イソインドール-1,3-ジオン · 2H-イソインドール-1,3-ジオン · 1H-イソインドール-1,3(2H)-ジオン · イソインドリン-1,3-ジオン · フタルイミド標準品
識別子と物理属性
| CAS No. | 85-41-6 |
|---|---|
| 分子式 | C8H5NO2 |
| 平均分子量 | 147.13 g/mol |
| 単同位体質量 | 147.0320284 g/mol |
| SMILES | O=C1NC(=O)c2ccccc21 |
| InChIKey | XKJCHHZQLQNZHY-UHFFFAOYSA-N |
| PubChem CID | 6809 |
| ChEMBL | CHEMBL277294 |
| ChEBI | CHEBI:38817 |
| EC No. | 201-603-3 |
| DTXSID | DTXSID3026514 |
| 現地名 | フタルイミド |
化学・物理的性質
| XLogP | 1.1 |
|---|---|
| 極性表面積 | 46.2 |
| 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 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 190 |
| 物質分類 | Nitrogen Compounds -> Other Nitrogen RingsPhthalate |
| pH | HAS SLIGHTLY ACIDIC PROPERTIES3.8 (0.6g/l, H2O) |
| 農薬 | Environmental transformation -> Pesticide transformation products (metabolite, successor) |
| LogP（分配係数） | log Kow = 1.151.04 |
| Color/Form | MONOCLINIC PRISMS FROM WATER OR BY SUBLIMATIONNEEDLES FROM WATER, PRISMS FROM ACETIC ACIDLEAFLETS (SUBLIMATION)White crystalline leaflets |
| 溶解度 | less than 1 mg/mL at 67.1 °F (NTP, 1992)FREELY SOL IN AQ ALKALI HYDROXIDESALMOST INSOL IN BENZENE, PETROLEUM ETHERFAIRLY SOL IN BOILING ACETIC ACIDSATURATED AQ SOLN CONTAINS 0.036 G @ 25 °C, 0.07 G @ 40 °C, ABOUT 0.4 G @ BOILING POINT100 G OF BOILING ALCOHOL DISSOLVES 5 G PHTHALIMIDEWater solubility = 360 mg/l水: わずかに溶ける(lit.)<0.1 g/100 mL で 19.5 ºC |
| 沸点 | Sublimes (NTP, 1992)366 °C |
| Decomposition | WHEN PHTHALIMIDE IS HEATED IT EMITS TOXIC VAPORS. |
| 融点 | 460 °F (NTP, 1992)238 °C232-235 °C(lit.) |
| 蒸気圧 | 0.00000001 [mmHg]0.001Pa at 25℃ |
| Physical Description | Phthalimide is a white to light tan powder. Slightly acidic. (NTP, 1992)Dry PowderCBIWhite solid[Hawley] White to light tan solid[CAMEO] White crystalline powder[Alfa Aesar MSDS] |
| Ionization Efficiency | Negative0.0510.5Agilent XCTElectrospray ionizationammonia (10nM) |
| 密度 | 1.21 |
| 屈折率 | 1.4700 (estimate) |
| 引火点 | 165 °C |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | 8.3(at 25℃) |
| 外観・状態 | 結晶フレーク |
| 色 | 白色～やや黄色 |
| Merck | 14,7373 |
| BRN | 118522 |
| ヘンリー定数 | 9.9×102 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)8(11)9-7/h1-4H,(H,9,10,11) |
| InChIKey | XKJCHHZQLQNZHY-UHFFFAOYSA-N |
| SMILES | O=C1NC(=O)c2ccccc12 |
| LogP（分配係数） | 1.15 |
| CAS データベース | 85-41-6(CAS DataBase Reference) |
| NISTの化学物質情報 | Phthalimide(85-41-6) |
| EPAの化学物質情報 | Phthalimide (85-41-6) |
化学的特性
white to slightly yellowish crystalline flakes
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 98.2% (111 of 113) of all reports.Not ClassifiedAggregated GHS information provided per 113 reports by companies from 3 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Chemical: 1H-Isoindole-1,3(2H)-dione1H-Isoindole-1,3(2H)-dione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Isoindole-1,3(2H)-dione 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: 29-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13146Phthalimide: Does not have an individual approval but may be used under an appropriate group standard |
| 火災危険 | Literature sources indicate that this compound is combustible. (NTP, 1992) |
| 健康有害性 | ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. (NTP, 1992) |
| 有害性の概要 | Highly irritating to skin, eyes, and upper respiratory tractNo teratogenic effects observed in rabbits at doses of 150mg/kg on days 7-12 of pregnancyEmergency treatment: Phthalimide fungicidesPhthalimide fungicides include Captan and Captafol that are of low order of acute toxicity. Both are skin sensitizers that in animal experiments can cause cancer and liver, reproductive, and developmental toxicity. [HSDB] Not irritating to skin and mildly irritating to eyes of rabbitsIn 4-week inhalation study of rats, no gross, hematological, or histopathological findingsNo evidence of mutagenicityOf about twelve studies, only two produced any evidence of teratogenicity[IUCLID] Not teratogenic in rabbits at 150 mg/kg/dayRabbits are very sensitive to teratogenic effects of thalidomide (suspected human teratogen), of which phthalimide is a residue[REPROTOX] An irritantCan be absorbed through skin[Alfa Aesar MSDS] See Captan and Captafol. See N-(Cyclohexylthio)phthalimide. |
| 反応性グループ | Amides and Imides |
| Reactivity Profile | PHTHALIMIDE is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). This chemical forms salts with bases. (NTP, 1992) |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Not Classified |
| Skin, Eye, and Respiratory Irritations | ...IT ACTS AS STRONG SKIN, EYE & UPPER RESP TRACT IRRITANT. |
| 消火 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| 応急処置 | 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. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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. |
| 処分方法 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Personal Protective Equipment (PPE) | 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) |
| 生態毒性値 | Cotton seedlings were used in phytotoxicity screening of phthalimide and 15 N-substituted derivatives. The seedlings were severely injured. To determine the target of this phytotoxicity ATPase isolated from wheat seedling roots was incubated with the phthalimides. Most of the phtha1imides had no significant irihibitory effect on ATPase activity. Further studies in which diamine oxidase iso1ated from wheat root tissues was incubated with the herbicides produced a good correlation between phytotoxic injury and degree of DAO inhibition. Since it is known that amine oxidases are involved in the biosynthesis of the plant hormnone indoleacetate it is suggested that these DAO inhibitors act by affecting plant growth regulation. |
| 環境中動態 | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 100(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that phthalimide should have high mobility in soil(SRC). The adsorptivity of phthalimide is expected to be sensitive to pH since phthalimide has a pKa of 8.3(9). Volatilization of phthalimide should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1X10-8 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 1X10-8 mm Hg(5,SRC). Phthalimide may not be susceptible to direct photolysis on soil surfaces based on its lack of absorption of light at wavelengths >290 nm(6,SRC). According to two activated sludge biodegradation studies, phthalimide will biodegrade rapidly in soil(7,8).AQUATIC FATE: An estimated Koc value of 100(SRC), determined from an experimental log Kow(1) and a recommended regression-derived equation(2), indicates that phthalimide should not adsorb to suspended solids and sediment(SRC) in the water(2,SRC). The adsorptivity of phthalimide is expected to be sensitive to pH since phthalimide has a pKa of 8.3(8). Phthalimide will be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). An estimated BCF value of 4.4(2,SRC), from an experimental log Kow(1), suggests that phthalimide will not bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(4). The half-lives for the base-catalyzed hydrolysis of phthalimide have been determined to be 1.6 days at a pH of 7, and 4 hours at a pH of 8(5,SRC). According to two activated sludge biodegradation studies, phthalimide will biodegrade rapidly in water(6,7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phthalimide, which has an estimated vapor pressure of 1X10-8 mm Hg at 25 °C(2,SRC) will exist primarily in the particulate phase in the ambient atmosphere. Vapor-phase phthalimide 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 about 2.6 days(3,SRC). Particulate-phase phthalimide may be physically removed from the air by wet and dry deposition(SRC). |
| Effluent Concentrations | Phthalimide was listed as a contaminant found in advanced treatment water in a survey of US cities, including Orange County,CA, on 1/27/76(1). |
| Soil Adsorption/Mobility | The Koc of phthalimide is estimated as approximately 100(SRC), using an experimental log Kow of 1.15(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that phthalimide should have high mobility in soil(SRC). The adsorptivity of phthalimide is expected to be sensitive to pH since phthalimide has a pKa of 8.3(4). |
| TSCA Test Submissions | The ability of phthalimide to induce specific locus mutations at the TK locus in cultured L5178Y mouse lymphoma cells (Mouse Lymphoma Mutagenicity Assay) was evaluated in the presence and absence of mouse liver S-9 metabolic activation. Based on preliminary toxicity tests, 5 nonactivated cultures treated with 65, 130, 260, 520 and 1040ug/ml were cloned, producing a range of 295.7 - 171.5% relative growth. Five S-9 activated cultures treated with the same concentrations were cloned, producing a range of 648.9 - 142.9% relative growth. None of the cultures produced mutant frequencies significantly greater than the solvent control (DMSO).The mutagenicity of phthalimide was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538 (Ames Test) and in Saccharomyces cerevisiae tester strain D4, both in the presence and absence of Aroclor-induced rat liver S-9 fraction. Phthalimide, diluted with DMSO, was tested at concentrations up to 500ug/plate using the Overlay Method. Phthalimide did not cause a positive response in any of the tester strains with or without metabolic activation.Subchronic toxicity was evaluated in groups of 5 male and 5 female Sprague-Dawley rats receiving once daily 6 hour exposures to heated phthalimide dust at concentrations of 51, 154 or 523 mg/m3, 5 days a week for 4 weeks. Mortality, changes in body weight, or abnormal behavioral reactions were not observed in any animal at any dose level during the treatment period. Phthalimide did not induce changes in the following parameters at any dose level when treated animals were compared to controls: erythrocyte and leukocyte countshemoglobinhematocritcorpuscular volumehemoglobin concentrationblood levels of urea nitrogen, alkaline phosphatase, glutamic pyruvic transaminase, and glucoseurine levels of glucose, albumin, and microscopic elementsurine pH. Lung weights were statistically significantly (test not specified, p < 0.05) lower in females in the 51 and 154 mg/m3 dose groups, while decreases were observed in lung weights (p < 0.01) and lung to body weight ratios (p < 0.05) in the 523 mg/m3 dose group females. The weights of the brain, gonads, heart, kidneys, liver, and spleen were not statistically significantly (p > 0.05) changed in any animal at any dose level compared to controls. Gross necropsy with histopathological examination of brain, gonads, heart, kidneys, liver, lung, spleen, lymph node, pituitary gland, and urinary bladder did not reveal any pathology in the 523 mg/m3 dose groupa single renal cortical adenoma observed in one male in the 523 mg/m3 dose group was not attributed to the effect of the test article. |
| Human Toxicity Excerpts | ...IT ACTS AS STRONG SKIN, EYE & UPPER RESP TRACT IRRITANT.... N-sulfinyl phthalimide fungicides are widely used agricultural products with low acute toxicity. /Phthalimides/ |
| Artificial Pollution Sources | Phthalimide's production and use in the production of phthalocyanine dyes(1), in the synthesis of primary amines and amino acids in the form of its sodium or potassium salt(1), as synthetic indigo via anthranilic acid(2), as a fungicide(2), in organic synthesis(2) and as a laboratory reagent(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | PHTHALIMIDES WERE EASILY DECOMPOSED BY TEST ACTIVATED-SLUDGE.Using activated sludge which was daily used in operating a joint wastewater treatment plant, phthalimide was easily biodegraded according to COD and TOC removal of 63 and 88 percent, respectively(1). Using adapted activated sludge as the inoculum, phthalimide degraded 96.2 percent based on COD removal at a biodegradation rate of 20.8 mg COD/g-hour(2). |
| Environmental Bioconcentration | An estimated BCF value of 4.4 was calculated for phthalimide(SRC), using an experimental log Kow of 1.15(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will not be an important fate process(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for phthalimide is estimated as 1X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that phthalimide will be essentially nonvolatile from water surfaces(2,SRC). Phthalimide's vapor pressure, 1X10-8 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil should not occur(SRC). |
| Non-Human Toxicity Excerpts | SINGLE ADMIN MORE SENSITIVE METHOD TO DETECT TERATOGENICITY. MATERNAL MORTALITY OR FETAL RESORPTION PREDOMINANT RESULTS OF REPEATED ADMIN OF TOXIC LEVELS.... Was noted not teratogenic in rabbits when used in amounts of 150 mg/kg on days 7 through 12 of pregnancy.The mouse limb bud micromass assay is one of many short-term tests proposed as preliminary screens for potential developmental toxicity. Previous efforts to validate this assay have used too few "nonteratogens." The purpose of this study was to examine additional compounds, most of which, based on the literature were perceived to have low potential for developmental toxicity in vivo. In addition a method of data analysis was sought that would identify selective developmental toxins in the micromass assay i.e. those that are effective at dosages not maternally toxic. The concentration of each of 23 compounds that produced a 50% inhibition of radiolabeled thymidine and sulfate incorporation was determined and used to calculate a thymidine/sulfate ratio. The thymidine/sulfate ratio may be a useful measure of developmental hazard since thymidine incorporation measures toxicity toward a general cell function (DNA synthesis) and sulfate incorporation measures mainly toxicity toward a developmentally specific cell activity (chondroitin sulfate synthesis). All compounds tested produced thymidine/sulfate ratios of less than 2.0. Since 22 of these 23 compounds are classified as nonteratogens or nonselective developmental toxins in vivo a low thymidine/sulfate ratio in this in vitro assay system nay be capable of discriminating potential for developmental hazard in vivo.An in vitro teratogen assay has been developed that uses Drosophila embryo cell cultures. The endpoints selected in assessing the teratogenic potential of any agent (physical or chemical) involves detection of interference with normal muscle and/or neuron differentiation, induction of heat shock (stress) proteins, and inhibition of normal neurotransmitter levels. Current studies involve use of reporter gene technology (protein fusions) to identify teratogenicity. Results so far suggest that the Drosophila assay is capable of accurately establishing if a particular agent tested can act as a teratogen by a variety of appropriate endpoints (morphological, biochemical, molecular). Furthermore, this assay can be used not only as a teratogen screen, but also in mechanistic studies of abnormal development, gene involvement in teratogenic resistance, and the possible role of heat shock proteins in preventing birth defects.Glutamate neurotoxicity is correlated with an increase of cytosolic free calcium(2+) some cell systems activation of calcium(2+) dependent endonucleases or formation of free radicals can damage DNA and activate the chromatin bound enzyme poly(A~P-ribose) polymerase. We have investigated whether poly(ADP-ribose) may be Involved In glutamate neurotoxicity in vitro. Cerebellar granule cells at 12 days in culture when treated with a toxic dose of glutamate (100 uM) showed a rapid and transient increase of polyADP-ribose immunoreactivity. Cellular immunostaining was heterogeneous and returned to control levels after washout of glutamate. In the same cell preparations glutamate elicited a marked increase in enzyme protein immunoreactivity which persisted at later times. Non-toxic doses of glutamate did not affect immunostaining. In another set of experiments, poly(ADP-ribose) mRNA was increased 30 min after glutamate. In order to investigate the role of poly(ADP-ribose) in glutamate-mediated neurotoxicity structurally different inhibitors of poly(ADP-ribose) (3-aminobenzamide, benzamide, 3-aminophthalhydrazide) and their inactive analogues benzoic acid and phthalimide) were tested in this model. Addition of the inhibitors to cultures 60 min before and during the 30 min of glutamate treatment prevented neuronal death by 60-100%, assessed 24 hr later. Glutamate-induced calcium(2+) influx was not affected. Inactive analogues failed to afford neuroprotection. These data indicate that not only is poly(ADP-ribose) activated by the early possib1y calcium(2+)-mediated mechanisms initiated by glutamate but that it might also actively contribute to the subsequent neuronal death. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of phthalimide with photochemically produced hydroxyl radicals has been estimated as 6.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 2.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The rate constant for the base-catalyzed hydrolysis of phthalimide has been determined to be 4.8 l/mole-sec(2). This corresponds to a half-life of approximately 1.6 days at a pH of 7, and 4 hours at a pH of 8(2,SRC). Phthalimide may not be susceptible to direct photolysis based on its lack of absorption of light at wavelengths >290 nm(3,SRC). |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | TI3920000 |
| 毒性 | LD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rabbit > 7940 mg/kg |
| 税関コード | 29251995 |
| 危険文句（R） | 20/21/22-36/37/38-40 |
| 化審法 | (5)-79 |
| 安全措置（S） | 22-24/25 |
| 自然発火温度 | >500 °C |
| 貯蔵分類 | 13 - Non Combustible Solids |
| 有害物質データ | 85-41-6(Hazardous Substances Data) |
用途
解説
1,2-benzenedicarboximide．C8H5NO2(147.13)．フタルイミドは，無水フタル酸をアンモニアあるいは炭酸アンモニウムなどと加熱して，イミド化によってつくられる．また，フタルアミドやフタル酸アンモニウムから脱水によっても得られる．昇華性針状晶．融点233～235 ℃．熱酢酸，アルカリ水溶液などに可溶，ベンゼン，エタノールなどに難溶．难溶于水，但溶于热乙醇（乙醇）。它具有弱酸性，以盐的形式很好地溶解在碱性水溶液中。NHの水素はプロトン性が強く，容易にN-アルカリ金属塩をつくる．これにハロゲン化アルキルを反応させると，種々のN-アルキル誘導体をつくることができ，このことは第一級アミンの合成に利用される．酰亚胺基的氢原子在乙醇中与氢氧化钾反应，被取代生成邻苯二甲酰亚胺钾。由卤代烷作用产生的N-烷基邻苯二甲酰亚胺可水解合成伯胺（加布里埃尔合成）。また，次亜塩素酸を作用させると，ベックマン転位反応によりアントラニル酸になる．染料，顔料の原料として用いられる．森北出版「化学辞典（第2版）
用途
フタル酸類は合成樹脂のモノマーとして利用されたり、特にエステル体の一部は、熱可塑性樹脂の可塑剤として30%?70%w/wほど添加される。
用途
合成インジゴ、殺菌剤
用途
有機合成原料。
一般的な説明
White to light tan powder. Slightly acidic.
使用用途
フタルイミドは、有機合成原料として用いられています。 その他、アミノ酸やフタロシアニン色素などの合成中間体として用いられたり、殺菌剤や酸化反応、光反応の阻害剤としても使用されます。
製法・合成法
純化方法
Crystallise the imide from EtOH (20mL/g) (charcoal), or sublime it. For potassium phthalimide see entry in “Metal-organic Compounds”, Chapter 5. [Beilstein 21/10 V 270.]