2,3,4-Trichloronitrobenzene

HCID 28697CAS 17700-09-3

Substructure search Find similar structures

Basic information

Standard SMILES: O=[N+]([O-])c1ccc(Cl)c(Cl)c1Cl
InChIKey: BGKIECJVXXHLDP-UHFFFAOYSA-N
Molecular formula: C6H2Cl3NO2
Average molar mass: 226.4 g/mol
Monoisotopic mass: 224.91511134

Overview

2,3,4-trichloronitrobenzene appears as needles or light yellow fluffy solid. (NTP, 1992)

Names & identifiers

Preferred name: 2,3,4-Trichloronitrobenzene
IUPAC: 1,2,3-trichloro-4-nitrobenzene
English name: 2,3,4-TRICHLORONITROBENZENE
Molecular formula: C6H2Cl3NO2
Molecular weight: 226.44

Names & synonyms

1,2,3-Trichloro-4-nitrobenzene2,3,4-TRICHLORONITROBENZENE17700-09-32,3,4-Trichloro-1-nitrobenzeneBenzene, 1,2,3-trichloro-4-nitro-4-Nitro-1,2,3-trichlorobenzeneBenzene, 4-nitro-1,2,3-trichloro-DTXSID0026202EINECS 241-705-5NSC 91490BRN 22119511-Nitro-2,3,4-trichlorobenzene

Show more names

TIMTEC-BB SBB009919Anagrelide Impurity 131,2,3-Trichloronitrobenzene2,3,4-Trichloroniteobenzene4-nitro-1,2,3-trichlorobenze4-nitro-1,2,3-trichloro-benzen

NSC-91490339A4728AKDTXCID8062022-05-00-00186 (Beilstein Handbook Reference)TRICHLORONITROBENZENE, 2,3,4-RefChem:4417242,3,4Trichloronitrobenzene1Nitro2,3,4trichlorobenzene

Database identifiers

CAS: 17700-09-3、29595-61-7
PubChem CID: 28697
DTXSID: DTXSID0026202
ChEMBL: CHEMBL354330
UNII: 339A4728AK
EC Number: 241-705-5、249-716-7
Nikkaji: J141.353H

Properties

Computed structural properties

XLogP: 3.6
Topological polar surface area: 45.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 12
Formal charge: 0
Complexity: 184

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Nitros, Aromatic

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy

LogP3.54

Solubilityless than 1 mg/mL at 73 °F (NTP, 1992)

Melting Point131 to 133 °F (NTP, 1992)

Vapor Pressure0.000792 [mmHg]

Physicochemical properties

Melting point: 53 · 53-56 °C(lit.)
Boiling point: 296.2 · 296.2±35.0 °C(Predicted)
Density: 1.7193 · 1.7193 (rough estimate)
refractive index: 1.63 · 1.6300 (estimate)
Flash point: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
form: powder to crystal
color: White to Light yellow to Green
Water Solubility: 26.04 mg/L · 26.04mg/L(20 ºC)
BRN: 2211951 · 2211951
Henry's Law Constant: 1.1 · 1.1×100 mol/(m3Pa) at 25℃, Zhang et al. (2010)
InChI: InChI=1S/C6H2Cl3NO2/c7-3-1-2-4(10(11)12)6(9)5(3)8/h1-2H
InChIKey: BGKIECJVXXHLDP-UHFFFAOYSA-N
SMILES: C1(Cl)=CC=C([N+]([O-])=O)C(Cl)=C1Cl
CAS DataBase Reference: 17700 · 17700-09-3(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 339 A4728AK · 339A4728AK
EPA Substance Registry System: 1 · 1,2,3-Trichloro-4-nitrobenzene (17700-09-3)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302+H312+H332-H315-H319-H335
Precautionary statements: 261 · P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn
Risk Statements: 20 · 20/21/22-36/37/38
Safety Statements: 26 · 26-37/39-36/37
RIDADR: 1578 · UN 1578 6.1/PG 2
WGK Germany: 3 · 3
RTECS: 6612000 · DA6612000
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29049095 · 29049095
Storage Class: 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Toxicity: 410 mLg/plate · mic-sat 410 mLg/plate MUREAV 116,217,1983
Limited Quantities: 0.5 Kg · 0.5 Kg (solid)
Excepted Quantities: Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 45.7% (37 of 81) of reports.

Warning

H302 (54.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 81 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

DOT LabelPoison

Fire HazardsFlash point data for this compound are not available. It is probably combustible. (NTP, 1992)

Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Hazards SummaryA skin and eye irritant; May induce methemoglobinemia; Readily absorbed through skin; [IUCLID] A skin and strong eye irritant; Harmful by ingestion, inhalation, and skin absorption; May induce methemoglobinemia; [Sigma-Aldrich MSDS]

Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Reactivity Profile2,3,4-TRICHLORONITROBENZENE is incompatible with strong bases and strong oxidizing agents.

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992)

First Aid · 1 item

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.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol 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.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
rtecs: DA6612000
ridadr: UN 1578 6.1/PG 2
hs_code: 29049095
Toxicity: mic-sat 410 mLg/plate MUREAV 116,217,1983
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 26-37/39-36/37
hazard_class: 6.1
Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group: III
target organs: Respiratory system
Hazard statements: H302+H312+H332-H315-H319-H335
Limited Quantities: 0.5 Kg (solid)
Excepted Quantities: Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338

Chemistry & industry

Applications · 2 items

Uses2,3,4-Trichloronitrobenzene is a useful synthetic intermediate that is mainly used as the starting material in the synthesis of third generation quinolone antibacterial drugs, such as Lomefloxacin (L469415, HCl) and Ofloxacin (O245750). 2,3,4-Trichloronitrobenzene is also used as the starting material in the synthesis of Aclonifen (A190200); a compound used as a pesticide and herbicide.

General DescriptionNeedles or light yellow fluffy solid.