化工社化工社 化学情報印刷レポート · 研究参考用
N,N-ジメチル-4-ニトロソアニリン
N,N-ジメチル-4-ニトロソアニリン · p-ニトロソ-N,N-ジメチルアニリン · N,N-ジメチル-4-ニトロソベンゼンアミン · ウルトラブリリアントブルーP · アクセレリン · NDMA【ジメチルニトロソアニリン】 · N,N-ジメチル-p-ニトロソアニリン · 4-ニトロソ-N,N-ジメチルアニリン
識別子と物理属性
| CAS No. | 138-89-6 |
|---|---|
| 分子式 | C8H10N2O |
| 平均分子量 | 150.18 g/mol |
| 単同位体質量 | 150.07931295 g/mol |
| SMILES | CN(C)c1ccc(N=O)cc1 |
| InChIKey | CMEWLCATCRTSGF-UHFFFAOYSA-N |
| PubChem CID | 8749 |
| ChEMBL | CHEMBL1569493 |
| ChEBI | CHEBI:59990 |
| EC No. | 205-343-1 |
| DTXSID | DTXSID7025138 |
| 現地名 | N,N-ジメチル-4-ニトロソアニリン |
化学・物理的性質
| XLogP | 1.8 |
|---|---|
| 極性表面積 | 32.7 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 1 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 128 |
| 物質分類 | Nitrogen Compounds -> Other Aromatics (Nitrogen)Reactive agents - 1st degree |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| 密度 | 1.145 (NTP, 1992) - Denser than waterwill sink1.145 @ 20 °C1,15 g/cm3 |
| Color/Form | GREEN PLATES OR LEAFLETSGREENISH-YELLOW SOLID |
| 溶解度 | less than 0.1 mg/mL at 70 °F (NTP, 1992)INSOL IN WATERSOL IN ALC, ETHERSOL IN FORMAMIDEInsoluble in watersoluble in Chloroform, Methanol |
| 融点 | 198.5 to 200.3 °F (NTP, 1992)92.5-93.5 °C85-87 °C(lit.) |
| 蒸気圧 | 0.4 [mmHg] |
| Physical Description | P-nitrosodimethylaniline appears as a dark green crystalline solid. Insoluble in water. Harmful if ingested.Green solid[Merck Index] Green crystalline powder[MSDSonline] |
| Collision Cross Section | 128.4 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID7025138] |
| 沸点 | 271.72°C (rough estimate) |
| 屈折率 | 1.6180 (estimate) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | powder to crystal |
| pKa（酸解離定数） | -0.90±0.12(Predicted) |
| 色 | Yellow to Brown to Dark green |
| Merck | 14,6638 |
| BRN | 607293 |
| 安定性 | 安定。強力な酸化剤、強力な還元剤、強酸、酢酸、無水酢酸とは相容れない。とても燃えやすい |
| InChI | 1S/C8H10N2O/c1-10(2)8-5-3-7(9-11)4-6-8/h3-6H,1-2H3 |
| InChIKey | CMEWLCATCRTSGF-UHFFFAOYSA-N |
| SMILES | N(C)(C)c1ccc(cc1)N=O |
| CAS データベース | 138-89-6(CAS DataBase Reference) |
| EPAの化学物質情報 | N,N-Dimethyl-p-nitrosoaniline (138-89-6) |
化学的特性
green crystalline powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 2.2% (1 of 45) of reports.DangerH251 (97.8%): Self-heatingmay catch fire [Danger Self-heating substances and mixtures]P235, P261, P264, P264+P265, P270, P271, P272, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, P407, P410, P413, P420, 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. |
|---|---|
| 規制情報 | Chemical: Benzenamine, N,N-dimethyl-4-nitroso-N,N-Dimethyl-4-nitrosoaniline: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| 輸送ラベル（DOT） | Spontaneously Combustible |
| 火災危険 | Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:· Flammable/combustible material. |
| 火災の可能性 | MODERATE, WHEN EXPOSED TO HEAT OR FLAME |
| 健康有害性 | Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:· Fire will produce irritating, corrosive and/or toxic gases. |
| 有害性の概要 | An irritant and sensitizing agent, but not known to cause methemoglobinemia[HSDB] Oral LD50 (mammals) = 650 mg/kgEffects after feeding rats lethal doses include somnolence, convulsions, and hematuria[RTECS] May spontaneously combust on contact with air[CAMEO] An irritantToxic if swallowedMay cause skin sensitization[Aldrich MSDS] |
| 輸送番号・ガイド（DOT） | 1369 135 |
| 反応性グループ | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| Reactivity Alerts | Pyrophoric |
| Reactivity Profile | P-NITROSODIMETHYLANILINE has a delayed violent reaction with acetic anhydride. (NTP, 1992) |
| DOT Hazard Classification | p-NitrosodimethylanilineUN1369Div 4.2 Spontaneously combustible material (49 eCFR § 173.124)PG II: the degree of danger presented by the material is medium |
| Air and Water Reactions | Susceptible to spontaneous combustion upon exposure to air. Insoluble in water. |
| 消火 | Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]: |
| 漏出応急措置 | · 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. |
| 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.General First Aid: |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| 保管条件 | ...KEEP ALL FLAMMABLES AWAY FROM AREA WHERE OXIDIZING AGENTS ARE STORED. STORAGE AREA SHOULD BE KEPT COOL & VENTILATED, & SHOULD BE FIREPROOF. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]: |
| Preventive Measures | ...CARE MUST ALWAYS BE TAKEN TO PREVENT ESCAPE OF VAPOR OR PARTICLES INTO ATMOSPHERE & TO PREVENT CONTAMINATION OF SKIN OR CLOTHING OF OPERATOR BY DIRECT CONTACT WITH CHEMICAL. /AROMATIC AMINES/ |
| Isolation and Evacuation | Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:Immediate precautionary measure |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]: |
| Emergency Response Planning Guidelines | · DO NOT USE WATER, CO2 OR FOAM ON MATERIAL ITSELF. |
| 有害作用 | Neurotoxin - Other CNS neurotoxin |
| Human Toxicity Excerpts | ...APPARENTLY NOT METHEMOGLOBIN FORMER, BUT IS HIGHLY IRRITATING TO SKIN BOTH AS PRIMARY IRRITANT & SENSITIZING AGENT. |
| Non-Human Toxicity Excerpts | P-NITROSODIMETHYLANILINE ADMIN TO NZR RATS & NZO MICE @ 300 MG/L DRINKING WATER OVER 1ST HALVES OF LIFESPAN, AVG AMT ACTUALLY CONSUMED 1.2 G/RAT & 262 MG/MOUSE. SIGNIFICANT INCREASES OCCURRED IN TUMORS OF LUNGS, KIDNEY & MALIGNANT LYMPHOMA IN RATS, & IN TUMORS OF LUNGS, DUODENUM & MALIGNANT LYMPHOMA IN MICE.THE EFFECTS OF A SINGLE SC INJECTION OF P-NITROSODIMETHYLANILINE (I) ON MALE RATS WERE STUDIED BY THE USE OF URINARY ENZYME MEASUREMENTS. ALKALINE PHOSPHATASE IN URINE WAS ELEVATED 48 HOURS AFTER I. ACID PHOSPHATASE AND MURAMIDASE ACTIVITIES IN URINE WERE SIGNIFICANTLY ELEVATED SOON AFTER THE ADMIN OF I AND REMAINED ABOVE THE NORMAL LEVELS LESS THAN OR EQUAL TO 120 HOURS AFTER I. URINE VOLUME AND PROTEIN LEVELS WERE MARKEDLY REDUCED. PROTEIN IN SERUM WAS REDUCED WHILE KIDNEY AND LIVER PROTEINS WERE RAISED. THE SIGNIFICANCE OF INTERACTION OF THE BIOTRANSFORMATION PRODUCTS OF I WITH THE RENAL SYSTEM IS DISCUSSED.AFTER THE APPLICATION OF 25 GAMMA P-NITROSODIMETHYLANILINE (I) TO EPILATED GUINEA PIG SKIN, THE ANIMAL INITIALLY BECAME MILDLY SENSITIVE TO THE COMPOUND, BUT 1-2 WEEKS LATER THE GUINEA PIG BECAME INSENSITIVE TO SC INJECTED I 500 GAMMA IN COMPLETE ADJUVANT. THE SHORTER THE INTERVAL BETWEEN THE TOPICAL APPLICATION OF I AND ITS INJECTION IN ADJUVANT, THE GREATER THE SENSITIVE REACTION, INDICATED BY THE DEGREE OF ERYTHEMA. ONE DAY AFTER A SENSITIZING INJECTION, SOME MEASURE OF INSENSITIVITY WAS INDUCED BY TOPICAL APPLICATION OF THE SENSITIZER. THEREFORE, UNRESPONSIVENESS AND SENSITIZATION DEVELOPED OVER THE SAME PERIOD OF TIME AFTER THE INITIAL TOPICAL APPLICATION OF SENSITIZER.N,N-Dimethyl-p-nitrosoaniline was found to be positive when tested for mutagenicity using the Salmonella/microsome preincubation assay, using the standard protocol approved by the National Toxicology Program (NTP). N,N-Dimethyl-p-nitrosoaniline was tested in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 1.000, 3.300, 5.000, 8.000,l 10.000, 33.000, 50.000, 100.000, 200.000, and 333.000 ug/plate. The compound was positive in strains TA100 and TA98 with and without activation. The lowest positive dose tested was 8.000 ug/plate in strain TA100 without activation. |
| F | 4.7-8-9 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | BX7175000 |
| 輸送番号（UN） | UN 1369 |
| 毒性 | LD50 orally in Rabbit: 65 mg/kg |
| 税関コード | 2921 42 00 |
| 危険文句（R） | 11-25-36/37/38-43 |
| 消防法 | 危-5-II |
| 危険表示 | F,T |
| 安全措置（S） | 16-26-36/37-45 |
| 危険等級 | 4.2Acute Tox. 3 OralEye Irrit. 2Self-heat. 1Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| 包装等級 | II |
| 貯蔵分類 | 4.2 - Pyrophoric and self-heating hazardous materials |
| 有害物質データ | 138-89-6(Hazardous Substances Data) |
用途
用途
有機化合物製造、加硫促進剤
使用
manufacture of organic Compounds; accelerator in vulcanizing; in printing fabrics.
一般的な説明
A dark green crystalline solid. Insoluble in water. Harmful if ingested.
製法・合成法
純化方法
Recrystallise the nitroso-aniline from pet ether or CHCl3/CCl4 and dry it in air. Alternatively suspend it in H2O, heat to boiling and add HCl until it dissolves. Filter, cool and collect the hydrochloride [42344-05-8] with m 177o after recrystallisation from H2O containing a small amount of HCl. The hydrochloride (e.g. 30g) is made into a paste with H2O (100mL) in a separating funnel. Add cold aqueous 2.5 NaOH or Na2CO3 to a pH of ~ 8.0 (green color due to the free base) and extract with toluene, CHCl3 or Et2O. Dry the extract (K2CO3), filter, distil off the solvent, cool the residue and collect the crystalline free base. Recrystallise it as above and dry it in air. [Beilstein 12 IV 1558.]