化工社化工社 化学情報印刷レポート · 研究参考用
4-ニトロベンジル クロリド
4-ニトロベンジル クロリド · 1-(クロロメチル)-4-ニトロベンゼン · 4-(クロロメチル)-1-ニトロベンゼン · 4-ニトロ-1-(クロロメチル)ベンゼン · 1-ニトロ-4-(クロロメチル)ベンゼン · p-ニトロベンジルクロリド · 4-ニトロベンジルクロリド · α-クロロ-p-ニトロトルエン
識別子と物理属性
| CAS No. | 100-14-1 |
|---|---|
| 分子式 | C7H6ClNO2 |
| 平均分子量 | 171.58 g/mol |
| 単同位体質量 | 171.00870611 g/mol |
| SMILES | O=[N+]([O-])c1ccc(CCl)cc1 |
| InChIKey | KGCNHWXDPDPSBV-UHFFFAOYSA-N |
| PubChem CID | 7482 |
| ChEMBL | CHEMBL176410 |
| ChEBI | CHEBI:87406 |
| EC No. | 202-822-7 |
| DTXSID | DTXSID4025745 |
| 現地名 | 4-ニトロベンジル クロリド |
化学・物理的性質
| XLogP | 2.5 |
|---|---|
| 極性表面積 | 45.8 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 138 |
| 物質分類 | Nitrogen Compounds -> Nitros, Aromatic |
| SpringerMaterials Properties | Density |
| 密度 | 1.5647 (NTP, 1992) - Denser than waterwill sink1.3246 (rough estimate) |
| Color/Form | Plates or needles from alcohol |
| 溶解度 | Insoluble (NTP, 1992)Sol in alcohol, ether, acetone, benzeneクロロホルム：可溶50mg/mL、透明～微かにかすむ、微黄色 |
| 沸点 | 230 °C @760 [mm Hg]112 °C (0.6 mmHg) |
| 融点 | 159.8 °F (EPA, 1998)71 °C |
| 蒸気圧 | 0.05 [mm Hg] @25 °C |
| 屈折率 | Index of refraction: 1.5647 at 62 °C1.5647 (estimate) |
| Physical Description | Benzene, 1-(chloromethyl)-4-nitro- is a solid. (EPA, 1998)Plates or needles from alcohol[HSDB] |
| Other Experimental Properties | UV: 6794 (Sadtler Research Laboratories Spectral Collection) /Benzyl chloride, 2-nitro/ |
| 外観・状態 | 結晶針または粉末 |
| 色 | ライトイエロー |
| BRN | 387187 |
| 安定性 | 安定。 強力な酸化剤、塩基、アミン、湿気、アルコールとは相容れない。 鋼に対して腐食性。 水とゆっくり反応する。 可燃性。 |
| InChI | 1S/C7H6ClNO2/c8-5-6-1-3-7(4-2-6)9(10)11/h1-4H,5H2 |
| InChIKey | KGCNHWXDPDPSBV-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)c1ccc(CCl)cc1 |
| CAS データベース | 100-14-1(CAS DataBase Reference) |
| NISTの化学物質情報 | 4-Nitrobenzyl chloride(100-14-1) |
| EPAの化学物質情報 | 1-(Chloromethyl)-4-nitrobenzene (100-14-1) |
化学的特性
white to light yellow crystal powde
安全性と法規制
| GHS 分類 | DangerH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 48 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302: Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | 4-Nitrobenzyl chloride: Does not have an individual approval but may be used under an appropriate group standard |
| 輸送ラベル（DOT） | Corrosive |
| 火災危険 | Incompatible with sodium hydroxide. (EPA, 1998) |
| 健康有害性 | Poisonous if swallowed or dust is inhaled. (EPA, 1998) |
| 有害性の概要 | Poisonous by ingestion and inhalation[CAMEO] CorrosiveCauses burnsA lachrymatorMay cause pneumonitis and pulmonary edema after inhalation of high concentrations[MSDSonline] |
| 反応性グループ | Halogenated Organic Compounds |
| Reactivity Profile | Incompatible with sodium hydroxide. [EPA, 1998]. A halogenated aromatic nitro compound. Aromatic nitro compounds range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups. |
| Air and Water Reactions | May react slowly with water. (NTP, 1992) |
| CERCLA 報告数量 | Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Benzene, 1-(chloromethyl)-4-nitro- is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500/10,000 lbs. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute toxicity (Oral) - Category 4 |
| 消火 | Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing. |
| 応急処置 | Signs and Symptoms of Acute Benzene, 1-(Chloromethyl)-4-Nitro-Exposure: Signs and symptoms of acute exposure to benzene, 1-(chloromethyl)-4-nitro- may be severe and include cyanosis (blue tint to the skin and mucous membranes), tachycardia (rapid heart rate), hypotension (low blood pressure), and cardiac arrhythmias. Respiratory depression and respiratory failure may also occur. Headache, lethargy, weakness, vertigo (dizziness), severe depression, and coma may be noted. GI symptoms include nausea and vomiting. Urine and vomitus may have the odor of bitter almonds. |
| 非火災時の漏出対応 | Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. If water pollution occurs, notify appropriate authorities. Do not touch spilled materialstop leak if you can do so without risk. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Protective Action Criteria (PAC) | 0.18 [mg/m3]2.0 [mg/m3]12 [mg/m3] |
| Personal Protective Equipment (PPE) | For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998) |
| 有害作用 | Dermatotoxin - Skin burns. |
| Non-Human Toxicity Excerpts | The mutagenicity of 24 benzyl derivatives, containing a variety of substituents & leaving groups, were assayed in strain TA100 using Ames plate incorporation assay. P-nitrobenzyl chloride (12000 revertants/umole) was mutagenic. It was also mutagenic in strain TA98 (700 revertants/umole), but not in strain TA98NR (a strain deficient in nitro reducatase activity). This study suggests that nitrobenzyl derivatives were mutagenic due to nitro reductive metabolism.Benzyl chloride, benzyl bromide, p-methylbenzyl chloride, & p-nitrobenzyl chloride were used to study chem reactivity with 4-(p-nitrobenzyl)pyridine & guanosine in vitro, in relation to mutagenic potency in Salmonella typhimurium & sister chromatid exchange (SCE) induction in CHO cells. Benzyl bromide was most reactive, followed by p-methylbenzyl chloride, benzyl chloride, & p-nitrobenzyl chloride. The order of mutagenicity was p-nitrobenzyl chloride much greater than benzyl bromide which was greater than benzyl chloride which was similar or equal to p-methylbenzyl chloride. They caused base-pair mutations only. The order of SCE-inducing ability decreased as follows: benzyl bromide greater than benzyl chloride which was similar or equal to p-nitrobenzyl chloride which was similar or equal to p-methylbenzyl chloride. The high mutagenicity of p-nitrobenzyl chloride in bacteria may be due to reactions other than direct aralkylation. |
| Toxicity Data | LCLo (rat) = 280 mg/m3/4h |
| F | 4.8-19-21 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | XS9093000 |
| 輸送番号（UN） | UN 3261 8/PG 2 |
| 税関コード | 29049090 |
| 危険文句（R） | 22-34-36 |
| 化審法 | (3)-449 |
| 消防法 | 危険物第5類 |
| 危険表示 | C |
| 安全措置（S） | 26-36/37/39-45-27 |
| 危険等級 | 8Acute Tox. 4 OralSkin Corr. 1B |
| 包装等級 | II |
| 貯蔵分類 | 8A - Combustible corrosive hazardous materials |
| 有害物質データ | 100-14-1(Hazardous Substances Data) |
用途
用途
有機合成原料 (NITE総合検索 (ACCESS ON JAN. 2011)
使用
4-Nitrobenzyl chloride was used to prepare unsymmetrically N,N′-bis(substituted) 4,13-diaza-18-crown-6-ether derivatives.
一般的な説明
Solid.
製法・合成法
調製方法
Chlorination of 4-nitrotoluene at 190 ℃ without catalyst gives 4-Nitrobenzyl chloride. The alternative process of nitration of benzylchloride coproduces 2-nitrobenzyl chloride and requires a difficult separation stage.
純化方法
Crystallise the chloride from CCl4, dry diethyl ether, or n-heptane, and dry it under vacuum. IRRITANT.[Beilstein 5 IV 856.]