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2,4,5-Trichloronitrobenzene

HCID 6983
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
89-69-0
Standard SMILES
O=[N+]([O-])c1cc(Cl)c(Cl)cc1Cl
InChIKey
IBRBMZRLVYKVRF-UHFFFAOYSA-N
Molecular formula
C6H2Cl3NO2
Average molar mass
226.4 g/mol
Monoisotopic mass
224.91511134

Overview

Prisms or needles in alcohol; yellow powder. (NTP, 1992)

Names & identifiers

Preferred name
2,4,5-Trichloronitrobenzene
IUPAC
1,2,4-trichloro-5-nitrobenzene
English name
1,2,4-Trichloro-5-nitrobenzene
Molecular formula
C6H2Cl3NO2
Molecular weight
226.44

Names & synonyms

2,4,5-TRICHLORONITROBENZENE1,2,4-Trichloro-5-nitrobenzene89-69-0Benzene, 1,2,4-trichloro-5-nitro-1-Nitro-2,4,5-trichlorobenzene5-Nitro-1,2,4-trichlorobenzene2,4,5-trichloro-1-nitrobenzene3,4,6-TrichloronitrobenzeneMFCD00007072DTXSID50262030YFY8PZD2M1,4,5-Trichloro-2-nitrobenzene
Show more names
2,4,5-TrichloronitroBifeprunox Impurity 522,3-DICHLOROANISOLE PESTANAL1,2,4-trichloro-5-nitro-benzen
NSC-50660NSC-56980NSC-609752,5-TrichloronitrobenzeneWLN: WNR BG DG EG1,4-Trichloro-5-nitrobenzeneBenzene,2,4-trichloro-5-nitro-2,4,5-Trichloronitrobenzene- 13C6

Database identifiers

CAS
89-69-0
PubChem CID
6983
DTXSID
DTXSID5026203
ChEMBL
CHEMBL1323107
UNII
0YFY8PZD2M
EC Number
201-931-7
Nikkaji
J2.838J

Properties

Computed structural propertiesFilling in

XLogP
3.5
Topological polar surface area
45.8 Ų
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 PropertiesBoiling point
LogP3.48
Density1.79 at 73 °F (NTP, 1992) - Denser than water; will sink
Solubilityless than 1 mg/mL at 61 °F (NTP, 1992)
Flash Pointgreater than 230 °F (NTP, 1992)
Boiling Point · 2 items

550 °F at 760 mmHg (NTP, 1992)

208 °C @760 [mm Hg]

Melting Point · 2 items

135 to 136 °F (NTP, 1992)

57 °C

Vapor Pressure0.000792 [mmHg]
Physical Description · 2 items

Prisms or needles in alcohol; yellow powder. (NTP, 1992)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 48.1% (37 of 77) of reports.

Danger

H301 (49.4%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 77 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationTP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.
DOT LabelPoison
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Exposure to this compound may cause eye and skin irritation. Absorption into the body leads to the formation of methemoglobin which in sufficient concentration causes cyanosis.
Hazards Summary · 1 item

An irritant; May induce methemoglobinemia; [NTP] May cause irritation; May induce methemoglobinemia; Toxic by ingestion; Harmful by inhalation and skin absorption; [Sigma-Aldrich MSDS] See Pentachloronitrobenzene and 2,3,4,5-Tetrachloronitrobenzene.

Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Reactivity Profile2,4,5-TRICHLORONITROBENZENE is incompatible with strong bases and strong oxidizing agents. (NTP, 1992).

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzene, 1,2,4-trichloro-5-nitro-: ACTIVE
Applications · 2 items

Uses2,4,5-Trichloronitrobenzene, is one of the by-products of Lindane (L465990) production, that can be used for agricultural crop protection. It is also used as an intermediate for the synthesis of various chemical compounds, such as a new class of 1H-benzimidazolecarboxamidines, acting as antibacterial and antifungal agents.

General DescriptionPrisms or needles in alcohol; yellow powder.

Upstream & downstream products

Upstream raw materials

1,2,4-Trichlorobenzene

Downstream products

2,4-Difluoro-5-chloronitrobenzeneQuintozine2,3,4,5-Tetrachloronitrobenzene4,5-Dichloro-2-nitroaniline2,4,5-Trichloroaniline

Related reactions

51 records
New reaction record
HRID 4238 reaction equation
HRID 4238As reactantuspto-grants-1988_02
HRID 46849 reaction equation
HRID 46849As reactantuspto-grants-1979_11
HRID 67806 reaction equation
HRID 67806As productuspto-grants-1982_08
HRID 67808 reaction equation
HRID 67808As productuspto-grants-1982_08
HRID 87105 reaction equation
HRID 87105As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 134916 reaction equation
HRID 134916As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 169008 reaction equation
HRID 169008As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 248797 reaction equation
HRID 248797As reactantuspto-grants-1993_05
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Compound notes

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Yellow solid; [CAMEO] Light yellow solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
52 · 52-57 °C
Boiling point
288 °C · 288 °C
Density
1.79 · 1.79
refractive index
1.63 · 1.6300 (estimate)
Flash point
170 °C · 170 °C
storage temp.
2 · 2-8°C
form
powder to crystal
color
2 · Prisms from EtOH or CS2
Water Solubility
27 mg/L · 27 mg/L (20 ºC)
CAS DataBase Reference
89 · 89-69-0(CAS DataBase Reference)
FDA UNII
0 YFY8PZD2M · 0YFY8PZD2M
NIST Chemistry Reference
1 · Benzene, 1,2,4-trichloro-5-nitro-(89-69-0)
EPA Substance Registry System
2 · 2,4,5-Trichloronitrobenzene (89-69-0)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
501 · P501-P270-P264-P301+P312+P330
Hazard Codes
N-Xn,N,Xn
Risk Statements
50 · 50/53-20/21/22
Safety Statements
61 · 61-60-36/37-28-25
RIDADR
3077 · 3077
RTECS
2275000 · DC2275000
Hazard Note
Harmful
TSCA
TSCA listed
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
29392900 · 29392900
Toxicity
1070 mg/kg · LDLo orl-mus: 1070 mg/kg AECTCV 14,111,85
Air and Water Reactions
Insoluble in water.
Hazard Classes and CategoriesAcute Tox. 3 (49.4%)

Safety & protection

Fire FightingFires involving this compound can be controlled using 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: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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)]:
Protective Action Criteria (PAC) · 3 items

2.3 [mg/m3]

25 [mg/m3]

150 [mg/m3]

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

tsca
TSCA listed
rtecs
DC2275000
ridadr
3077
hs_code
29392900
Toxicity
LDLo orl-mus: 1070 mg/kg AECTCV 14,111,85
risk_code
50/53-20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
N-Xn,N,Xn
hazard_note
Harmful
safety_code
61-60-36/37-28-25
hazard_class
6.1(b)
packing_group
III
Hazard statements
H302
Precautionary statements
P501-P270-P264-P301+P312+P330