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α-Chlor-4-nitrotoluol

4-Nitrobenzyl chloride

HCID 7482
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Grundinformationen

CAS
100-14-1
Standard-SMILES
O=[N+]([O-])c1ccc(CCl)cc1
InChIKey
KGCNHWXDPDPSBV-UHFFFAOYSA-N
Summenformel
C7H6ClNO2
Durchschnittliche Molmasse
171,58 g/mol
Monoisotopische Masse
171,00870611

Überblick

Benzene, 1-(chloromethyl)-4-nitro- is a solid. (EPA, 1998)

Namen und Bezeichner

Bevorzugter Name
4-Nitrobenzyl chloride
IUPAC
1-(chloromethyl)-4-nitrobenzene
Lokaler Name
α-Chlor-4-nitrotoluol
Englischer Name
4-Nitrobenzyl chloride
Summenformel
C7H6ClNO2
Molmasse
171.58

Namen und Synonyme

4-Nitrobenzyl chloride100-14-11-(Chloromethyl)-4-nitrobenzenep-Nitrobenzyl chlorideBenzene, 1-(chloromethyl)-4-nitro-alpha-Chloro-p-nitrotoluenep-(Chloromethyl)nitrobenzene4-(Chloromethyl)nitrobenzeneDTXSID40257454-nitrophenylmethyl chlorideToluene, alpha-chloro-p-nitro-3BLD9LVT3X
Weitere Namen anzeigen
p-nitrochlorideAKOS BBS-00003951NitrochlorobenzylNitrobenzylchlorideNitrobenzyl chloridà-chloro-4-nitrotolueneα-Chloro-4-nitrotoluene
BENZENE, 1-CHLOROMETHYL-4-NITRO-NSC-9803DTXCID105745CHEBI:87406para-nitrobenzyl chlorideRefChem:525941202-822-7alpha-Chloro-4-nitrotoluene

Datenbank-Bezeichner

CAS
100-14-1
PubChem CID
7482
DTXSID

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,5
Polarare Oberfläche (TPSA)
45,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
11
Formalladung
0
Komplexität
138

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Nitros, Aromatic
SpringerMaterials PropertiesDensity
Density1.5647 (NTP, 1992) - Denser than water; will sink
Color/FormPlates or needles from alcohol
Solubility · 2 Einträge

Insoluble (NTP, 1992)

Sol in alcohol, ether, acetone, benzene

Boiling Point230 °C @760 [mm Hg]
Melting Point · 3 Einträge

159.8 °F (EPA, 1998)

71 °C

71 °C

Vapor Pressure0.05 [mm Hg] @25 °C
Refractive IndexIndex of refraction: 1.5647 at 62 °C
Physical Description · 2 Einträge

Benzene, 1-(chloromethyl)-4-nitro- is a solid. (EPA, 1998)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H302 (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.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Gefahrenhinweise

Regulatory Information4-Nitrobenzyl chloride: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelCorrosive
Fire HazardsIncompatible with sodium hydroxide. (EPA, 1998)
Health HazardsPoisonous if swallowed or dust is inhaled. (EPA, 1998)
Hazards SummaryPoisonous by ingestion and inhalation; [CAMEO] Corrosive; Causes burns; A lachrymator; May cause pneumonitis and pulmonary edema after inhalation of high concentrations; [MSDSonline]
Reactive GroupHalogenated Organic Compounds
Reactivity Profile · 1 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites4-nitrobenzyl chloride has known human metabolites that include 4-nitrobenzyl-glutathione and S-(4-Nitrobenzyl)glutathione.

Verwendung und Herstellung

U.S. Exports(1987) No Data
U.S. Imports(1987) No Data
U.S. Production(1987) No Data
General Manufacturing InformationBenzene, 1-(chloromethyl)-4-nitro-: ACTIVE

Anwendungen

Verwenden4-Nitrobenzyl chloride was used to prepare unsymmetrically N,N′-bis(substituted) 4,13-diaza-18-crown-6-ether derivatives.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

4-[(4-Methylpiperazin-1-yl)methyl]aniline1-Methyl-4-(4-nitrobenzyl)piperazineα-Chlor-2,4-dinitrotoluol1-(4-Nitrophenyl)methyl-1,2,4-triazole6-((4-Nitrobenzyl)thio)-9-β-D-ribofuranosylpurin(4-Nitrophenyl)methanesulfonyl chloride

Zugehörige Reaktionen

145
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 26402
HRID 26402als Eduktuspto-grants-1979_04
Reaktionsgleichung von HRID 35862
HRID 35862als Eduktuspto-grants-1995_05
Reaktionsgleichung von HRID 37313
HRID 37313als Eduktuspto-grants-1995_05
Reaktionsgleichung von HRID 43057
HRID 43057als Eduktuspto-grants-2013_09
Reaktionsgleichung von HRID 65070
HRID 65070als Eduktuspto-grants-1986_09
Reaktionsgleichung von HRID 83641
HRID 83641als Eduktuspto-grants-2014_09
Reaktionsgleichung von HRID 90151
HRID 90151als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 97362
HRID 97362als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
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Weitere Aktionen
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DTXSID4025745
ChEMBL
CHEMBL176410
ChEBI
CHEBI:87406
UNII
3BLD9LVT3X
EC Number
202-822-7
Nikkaji
J4.978F

Plates or needles from alcohol; [HSDB]

Other Experimental PropertiesUV: 6794 (Sadtler Research Laboratories Spectral Collection) /Benzyl chloride, 2-nitro/

Physikochemische Eigenschaften

Schmelzpunkt
71 °C · 71 °C
Siedepunkt
112 °C · 112 °C (0.6 mmHg)
Dichte
1.3246 · 1.3246 (rough estimate)
Brechungsindex
1.5647 · 1.5647 (estimate)
Löslichkeit
50 mg/mL, · chloroform: soluble50mg/mL, clear to very slightly hazy, faintly yellow
Aggregatzustand
Crystalline Needles or Powder
Farbe
Light yellow
BRN
387187 · 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 · 100-14-1(CAS DataBase Reference)
NIST chemische Informationen
4 · 4-Nitrobenzyl chloride(100-14-1)
EPA chemische Informationen
1 · 1-(Chloromethyl)-4-nitrobenzene (100-14-1)
Air and Water ReactionsMay react slowly with water. (NTP, 1992)
CERCLA Reportable Quantities · 1 Eintrag

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 · 2 Einträge

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

Sicherheit und Schutzausrüstung

Fire FightingKeep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing.
First Aid · 1 Eintrag

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.

Nonfire Spill ResponseKeep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. If water pollution occurs, notify appropriate authorities. Do not touch spilled material; stop leak if you can do so without risk.
Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Protective Action Criteria (PAC) · 3 Einträge

0.18 [mg/m3]

2.0 [mg/m3]

12 [mg/m3]

Personal Protective Equipment (PPE) · 1 Eintrag

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)

Toxikologische Informationen

Adverse EffectsDermatotoxin - Skin burns.
Non-Human Toxicity Excerpts · 2 Einträge

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 DataLCLo (rat) = 280 mg/m3/4h

Regulatorische Informationen

CERCLA Reportable Quantities · 1 Eintrag

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.

Sicherheitsdaten

F
4.8-19-21
wgk
3
tsca
TSCA listed
ridadr
UN 3261 8/PG 2
hs_code
29049090
RTECS-Nr.
XS9093000
risk_code
22-34-36
hazard_code
C
safety_code
26-36/37/39-45-27
hazard_class
8
packing_group
II
Speicherklasse
8A - Combustible corrosive hazardous materials
Giftige Stoffe Daten
100-14-1(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 OralSkin Corr. 1B
p-Aminobenzylchloride
4-Amino-N,N-dimethylbenzylamin

Ergänzende Hinweise

DefinitionChEBI: A C-nitro compound that is nitrobenzene in which the hydrogen at position 4 is replaced by a chloromethyl group.