化工社化工社 化学情報印刷レポート · 研究参考用
2,4-ジニトロアニリン
2,4-ジニトロアニリン · 2,4-ジニトロベンゼンアミン · (2,4-ジニトロフェニル)アミン · 2，4ジニトロアニリン」 · ２，４ジニトロアニリン · ジニトロアニリン · 2,4‐ジニトロアニリン · 2,4-Dinitroaniline,~99%
識別子と物理属性
| CAS No. | 97-02-9 |
|---|---|
| 分子式 | C6H5N3O4 |
| 平均分子量 | 183.12 g/mol |
| 単同位体質量 | 183.02800564 g/mol |
| SMILES | Nc1ccc([N+](=O)[O-])cc1[N+](=O)[O-] |
| InChIKey | LXQOQPGNCGEELI-UHFFFAOYSA-N |
| PubChem CID | 7321 |
| ChEMBL | CHEMBL354318 |
| ChEBI | CHEBI:34242 |
| EC No. | 202-553-5 |
| DTXSID | DTXSID1021823 |
| 現地名 | 2,4-ジニトロアニリン |
化学・物理的性質
| XLogP | 1 |
|---|---|
| 極性表面積 | 118 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 5 |
| 回転可能結合数 | 0 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 221 |
| 物質分類 | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| SpringerMaterials Properties | Chemical shift |
| LogP（分配係数） | 1.84 (estimated)1.9 |
| 臭い | Musty odor |
| 密度 | 1.615 at 59 °F (USCG, 1999) - Denser than waterwill sink1.615 g/ml @ 14 °C1.62 g/cm³1.615 @25 °C1,61 g/cm3 |
| Color/Form | YELLOW NEEDLES FROM DIL ACETONE, GREENISH-YELLOW PLATES FROM ALCOHOL. |
| 溶解度 | less than 0.1 mg/mL at 73 °F (NTP, 1992)SOL IN HOT HYDROCHLORIC ACIDPRACTICALLY INSOL IN COLD WATERVERY SPARINGLY SOL IN BOILING WATER5.8 PARTS SOL IN 100 PARTS 88% ALCOHOL @ 18 °C1 PART SOL IN 132.6 PARTS OF 95% ALCOHOL @ 21 °CSolubility in water: noneDMSO (Slightly), Methanol (Slightly)0.06g/L（20℃） |
| 引火点 | 435 °F (NTP, 1992)223 °C435 °F (CLOSED CUP)222-224 °C c.c. |
| 沸点 | 56.7 °C316.77°C (rough estimate) |
| Decomposition | WHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES. |
| 融点 | 349 to 352 °F (NTP, 1992)187.5-188 °C187-188 °C177 °C |
| 蒸気密度 | 6.31 (NTP, 1992) - Heavier than airwill sink (Relative to Air)6.31 (AIR= 1) |
| 蒸気圧 | <0.001 hPa ( 25 °C) |
| 屈折率 | 1.6910 (estimate) |
| 貯蔵条件 | Flammables area |
| pKa（酸解離定数） | pK1:-14.25(+1) (25°C) |
| 外観・状態 | 結晶性粉末 |
| 色 | 黄色から黄緑色または黄褐色 |
| pH | 7 (1g/L in H2O) |
| Merck | 14,3270 |
| BRN | 982999 |
| ヘンリー定数 | 6.5×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定。酸化剤と相容れない。高温で激しく分解することがある。 |
| InChI | 1S/C6H5N3O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H,7H2 |
| InChIKey | LXQOQPGNCGEELI-UHFFFAOYSA-N |
| SMILES | Nc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O |
| CAS データベース | 97-02-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzenamine, 2,4-dinitro-(97-02-9) |
| EPAの化学物質情報 | 2,4-Dinitroaniline (97-02-9) |
化学的特性
yellow crystalline solid
安全性と法規制
| GHS 分類 | DangerH300: 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)H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral] |
|---|---|
| 規制情報 | Chemical: Benzenamine, 2,4-dinitro-2,4-Dinitroaniline: HSNO Approval: HSR004142 Approved with controls |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Special Hazards of Combustion Products: Vapors and combustion gases are irritatingCombustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 火災の可能性 | SLIGHT, WHEN EXPOSED TO HEAT OR FLAME. |
| 健康有害性 | May cause headache, nausea, stupor. Irritating to skin and mucous membrane. (USCG, 1999) |
| 有害性の概要 | A skin, eye, and respiratory tract irritantCan induce methemoglobinemiaMay be absorbed through skin[ICSC] A skin, eye, and respiratory tract irritantOral administration to rats induces methemoglobinemia (weak effect)Inhalation of 17 mg/m3/4hr/day in the first week of pregnancy caused increased embryo mortality and decreased embryo length in ratsEmergency treatment: AnilineAniline can induce methemoglobinemia and secondary hemolytic anemia and liver damage. [HSDB] ExplosiveA skin and mucous membrane irritant[CAMEO] Very toxic by inhalation, ingestion, and skin contact[eChemPortal: ESIS] An irritantCan be absorbed through skinMay induce methemoglobinemia[Alfa Aesar MSDS] |
| 反応性グループ | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| EC 分類 | Symbol: T+, NR: 26/27/28-33-51/53S: (1/2)-28-36/37-45-61 |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: II |
| TSCA 要件 | 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, 2,4-dinitro- is included on this list.Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329. |
| Reactivity Alerts | Explosive |
| Reactivity Profile | 2,4-DINITROANILINE may decompose violently at elevated temperatures. This compound can react with oxidizing materials, i.e. chlorine/hydrochloric acid. (NTP, 1992). In mixture with powdered charcoal ignited upon heating, [Cahiers, 1980, (99), 278]. |
| 消火 | Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothingUse water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| 応急処置措置 | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention . |
| 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. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| 安全保管 | Separated from strong oxidants and food and feedstuffs. Well closed. |
| 消火手順 | WATER, CARBON DIOXIDE, DRY CHEMICALUse water spray, dry chemical, foam, or carbon dioxide. Water or foam may cause frothing. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. /Nitropropanes/ |
| 保管条件 | Store in a cool, dry, well ventilated location. Separate from acids and oxidizing materials. Detached storage must be used.MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS ... SHOULD BE STORED IN A COOL WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, & SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED ... . |
| 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. |
| 漏出処分 | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. 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. |
| Preventive Measures | SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. |
| 生態毒性値 | LC50 Pimephales promelas (fathead minnow) 14.2 mg/l/96 hr (Confidence limit 13.5 to 15.0 mg/l). Affected fish lost schooling behavior and swam near the tank surface with half being hyperactive and half hypoactive. They had increased respiration and hemorrhaging, were darkly colored, and lost equilibrium prior to death. |
| 環境中動態 | TERRESTRIAL FATE: When released to soil, 2,4-dinitroaniline may undergo covalent chemical bonding with humic materials which can result in its chemical alteration to a latent form and tight adsorption. When covalently bound in this latent form, leaching in soil systems is not generally expected to occur. This covalent bonding proceeds in two stepsa rapid and reversible bonding followed by a slower and much less reversible reaction(1,SRC). Leaching in soil may be possible prior to the occurrence of the slower bonding reaction. In the absence of covalent bonding, moderate leaching may be possible (estimated Koc value of 240)(3,4,SRC). Although one biological screening study showed no biodegradation in river and sea water(2), insufficient data are available to assess the relative importance of biodegradation of 2,4-dinitroaniline in soil(SRC).AQUATIC FATE: By analogy to the aromatic amine chemical class(2), 2,4-dinitroaniline in the water column may be susceptible to photooxidation via hydroxyl and peroxy radicals(SRC). Aromatic amines have also been shown to undergo covalent bonding with humic materials in the water column and in sediment(1)partitioning from the water column to sediment and suspended material may therefore be important(SRC). Although one biological degradation study found evidence of no microbial degradation(3), insufficient data are available to assess the relative importance of biodegradation of 2,4-dinitroaniline in water. An estimated BCF value of 15(4,SRC) suggests that it will not bioconcentrate significantly in aquatic organisms(SRC). Aquatic hydrolysis and volatilization do not appear to be environmentally important(SRC).ATMOSPHERIC FATE: Based upon an estimated vapor pressure of 5.94X10-7 mm Hg at 25 °C(1), 2,4-dinitroaniline may exist in both the vapor and the particulate-phase in the ambient atmosphere(2,SRC). It is degraded relatively rapidly in the vapor phase in an average ambient atmosphere by reaction with photochemically produced hydroxyl radicals at an estimated half-life of about 17.7 hr(3,SRC). |
| 有害作用 | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| 暴露経路 | The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion. |
| Signs and Symptoms | Cough. Sore throat.MAY BE ABSORBED! Redness. Pain. |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | Aromatic amines have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solutionthe initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinonethese processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(3). In the absence of covalent bonding, a Koc of approximately 240 can be estimated for 2,4-dinitroaniline based on an estimated log Kow of 1.84(2) and a recommended regression-derived equation(1,SRC)this Koc value suggests medium soil mobility(4). |
| Artificial Pollution Sources | 2,4-Dinitroaniline may be released to the environment during its production and use in the preparation of azo dyes(1,SRC). |
| Environmental Biodegradation | 2,4-Dinitroaniline at an initial concn of 100 ppm showed no biodegradation in river and sea water after 3 days using a cultivation test method(1). |
| Environmental Bioconcentration | Based on an estimated log Kow of 1.84(2), the bioconcentration factor (BCF) for 2,4-dinitroaniline can be estimated to be about 15 from a recommended regression-derived equation(1,SRC). This BCF value suggests that bioconcentration in aquatic organisms may not be significant(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 2,4-dinitroaniline can be estimated to be approximately 1.51X10-10 atm-cu m/mole at 25 °C using a chemical structure estimation method(2,SRC). This value of Henry's Law constant suggests that 2,4-dinitroaniline is essentially nonvolatile from water(1). |
| Non-Human Toxicity Excerpts | 2,4-DINITROANILINE ADMIN ORALLY TO RATS SHOWED LOW TOXICITY. AFFECTED NERVOUS SYSTEM, CAUSED WEAK MET- & SULF-HEMOGLOBINEMIA, & DECR LEVEL OF THIOL GROUPS IN BLOOD.THE DNA DAMAGE INDUCED BY IN VIVO ADMINISTRATION OF 2,4-DINITROANILINE WAS DETERMINED ... . THE TARGET ORGANS FOR ULTIMATE CARCINOGENS PRODUCED IN MICE APPEAR TO BE THE LIVER AND THE KIDNEY. THE VALUES OBTAINED AFTER TREATMENT WITH 2,4-DINITROANILINE FALL IN THE RANGE OF CONTROL MICE.INHALATION OF 17 MG 2,4-DINITROANILINE/CU M FOR 4 HR/DAY WITHIN THE 1ST 19 OR 7 DAYS OF PREGNANCY INCREASED THE MORTALITY OF RAT EMBRYOS FROM 9.9 TO 18.8 AND 25.3%, RESPECTIVELY, AND DECREASED THE EMBRYO LENGTH ON THE 20TH DAY OF PREGNANCY FROM 29.0 TO 24.9 AND 25.2 MM, RESPECTIVELY. THE 7-DAY EXPOSURE ALSO DECREASED THE ALPHA2-GLOBULIN PERCENTAGE FROM 18.6 TO 14.2%. ...TWO FRAME-SHIFT HISTIDINE MUTANTS (TA1537 AND TA98) AND 2 BASE-PAIR SUBSTITUTED HISTIDINE MUTANTS (TA1535 AND TA100) OF SALMONELLA TYPHIMURIUM WERE EMPLOYED. BOTH THE SPOT TEST AND PLATE-INCORPORATION ASSAY INDICATED THAT /2,4-DINITROANILINE/ WAS MUTAGENIC WITH THREE OF THE TEST STRAINS. ...For more Non-Human Toxicity Excerpts (Complete) data for 2,4-DINITROANILINE (6 total), please visit the HSDB record page. |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | BX9100000 |
| 輸送番号（UN） | UN 1596 (DINITROANILINES) |
| PRTR法 | 第二種指定化学物質 |
| 税関コード | 29214210 |
| 危険文句（R） | 26/27/28-33-51/53 |
| 化審法 | (3)-403 |
| 安衛法 | 変異原性物質 |
| 消防法 | 危-5-II |
| 危険表示 | T+,N |
| 安全措置（S） | 28-36/37-45-61-28A |
| 危険等級 | 6.1Acute Tox. 1 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralAquatic Chronic 2STOT RE 2 |
| 包装等級 | II |
| 自然発火温度 | >365°C |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 有害物質データ | 97-02-9(Hazardous Substances Data) |
用途
用途
顔料、染料の合成中間体
用途
有機合成原料(染料、顔料)。
一般的な説明
Yellow powder or crystals with a musty odor. Sinks in water.
製法・合成法
調製方法
2,4-Dinitrochlorobenzene is aminated with aqueous ammonia initially at 70 ℃; then the temperature is allowed to rise gradually to 120 ℃ to complete the reaction. Only a low-pressure autoclave is required, compared with the amination of 2- chloro- and 4- chloronitrobenzene.
純化方法
Crystallise the nitroaniline from boiling EtOH by adding one-third volume of H2O and cooling slowly. Dry it on a steam oven. The N-acetyl derivative has m 180o. [Beilstein 12 IV 1689.]