HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
α-Chlor-4-nitrotoluol
1-(Chloromethyl)-4-nitrobenzene · P-NITROBENZYL CHLORIDE · p-nitrochloride · AKOS BBS-00003951 · Nitrochlorobenzyl · Nitrobenzylchloride · Nitrobenzyl chlorid · 4-NITROBENZYL CHLORIDE
Identifikatoren & physikalische Daten
| CAS No. | 100-14-1 |
|---|---|
| Summenformel | C7H6ClNO2 |
| Durchschnittliche Molmasse | 171,58 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | α-Chlor-4-nitrotoluol |
Chemische & physikalische Eigenschaften
| XLogP | 2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 45,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 138 |
| Stoffklassen | Nitrogen Compounds -> Nitros, Aromatic |
| SpringerMaterials Properties | Density |
| Dichte | 1.5647 (NTP, 1992) - Denser than waterwill sink1.3246 (rough estimate) |
| Color/Form | Plates or needles from alcohol |
| Löslichkeit | Insoluble (NTP, 1992)Sol in alcohol, ether, acetone, benzenechloroform: soluble50mg/mL, clear to very slightly hazy, faintly yellow |
| Siedepunkt | 230 °C @760 [mm Hg]112 °C (0.6 mmHg) |
| Schmelzpunkt | 159.8 °F (EPA, 1998)71 °C |
| Dampfdruck | 0.05 [mm Hg] @25 °C |
| Brechungsindex | 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/ |
| Aggregatzustand | Crystalline Needles or Powder |
| Farbe | Light yellow |
| BRN | 387187 |
| Stabilität | Stable. Incompatible with strong oxidizing agents, bases, amines, moisture, alcohols. Corrodes steel. Reacts slowly with water. Combustible. |
| 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 Datenbank | 100-14-1(CAS DataBase Reference) |
| NIST chemische Informationen | 4-Nitrobenzyl chloride(100-14-1) |
| EPA chemische Informationen | 1-(Chloromethyl)-4-nitrobenzene (100-14-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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] |
|---|---|
| Regulatorische Informationen | 4-Nitrobenzyl chloride: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | Incompatible with sodium hydroxide. (EPA, 1998) |
| Gesundheitsgefahren | Poisonous if swallowed or dust is inhaled. (EPA, 1998) |
| Gefahrenübersicht | Poisonous by ingestion and inhalation[CAMEO] CorrosiveCauses burnsA lachrymatorMay cause pneumonitis and pulmonary edema after inhalation of high concentrations[MSDSonline] |
| Reaktive Gruppe | 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-Meldepflichtmengen | 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 |
| Brandbekämpfung | 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. |
| Erste Hilfe | 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. |
| Freisetung ohne Brand | 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) |
| Unerwünschte Wirkungen | 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 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3261 8/PG 2 |
| Zollcode | 29049090 |
| RTECS-Nr. | XS9093000 |
| R-Sätze (R) | 22-34-36 |
| Gefahrensymbole | C |
| Sicherheitshinweise (S) | 26-36/37/39-45-27 |
| Gefahrenklasse | 8Acute Tox. 4 OralSkin Corr. 1B |
| Verpackungsgruppe | II |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
| Gefahrstoffdaten | 100-14-1(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
4-Nitrobenzyl chloride was used to prepare unsymmetrically N,N′-bis(substituted) 4,13-diaza-18-crown-6-ether derivatives.