HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

1,3,5-Trichlorobenzene

HCID 7950
New noteNew reactionRequest quotes
Print preview

Completing data — refresh the page later to see the latest

Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
108-70-3
Standard SMILES
Clc1cc(Cl)cc(Cl)c1
InChIKey
XKEFYDZQGKAQCN-UHFFFAOYSA-N
Molecular formula
C6H3Cl3
Average molar mass
181.4 g/mol
Monoisotopic mass
179.93003314

Overview

1,3,5-trichlorobenzene appears as white to off-white crystals. (NTP, 1992)

Names & identifiers

Preferred name
1,3,5-Trichlorobenzene
IUPAC
1,3,5-trichlorobenzene
English name
1,3,5-Trichlorobenzene
Molecular formula
C6H3Cl3
Molecular weight
181.45

Names & synonyms

1,3,5-TRICHLOROBENZENE108-70-3s-Trichlorobenzenesym-TrichlorobenzeneBenzene, 1,3,5-trichloro-1,3,5-TRICHLORO-BENZENEDTXSID8026195Symmetrical trichlorobenzene2HS4M0BX3CAI3-220311,3,5-TrichlorbenzolNSC-4389
Show more names
TCBTrichlorobenzene1,3,5-TCB1.3.5-Tric1,3,5-TrichL1,3,5-Trichlorobenze
DTXCID506195CHEBI:49916RefChem:412633203-608-6C6H3Cl3Anagrelide Impurity 13MFCD0000058563697-19-8

Database identifiers

CAS
108-70-3、63697-19-8
PubChem CID
7950
DTXSID
DTXSID8026195
ChEMBL
CHEMBL44228
ChEBI
CHEBI:49916
UNII
2HS4M0BX3C
EC Number
203-608-6
Nikkaji
J2.427I

Properties

Computed structural propertiesFilling in

XLogP
4.2
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
9
Formal charge
0
Complexity
63.3

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
SolventsSolvents -> Chlorinated Aromatics
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 2 items

log Kow = 4.19

4.15

Density · 2 items

1.456 g/cu cm at 20 °C (liquid)

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.0

Viscosity0.841 mPa.s at 70 °C
Color/Form · 3 items

Needles

White crystals

Long needles

Solubility · 5 items

less than 0.1 mg/mL at 67.1 °F (NTP, 1992)

Soluble in chloroform

Sparingly sol in alcohol; freely sol in ether, benzene, petroleum ether, carbon disulfide, glacial acetic acid

In water, 6.01 mg/L at 25 °C

Solubility in water, g/100ml at 25 °C: 0.0006

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 · 6 items

This chemical does not meet GHS hazard criteria for 7.8% (4 of 51) of reports.

Warning

H302 (88.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]

Hazard information

Regulatory Information · 6 items

Chemical: Benzene, 1,3,5-trichloro-

Hazard Traits - Bioaccumulation; Environmental Persistence

Benzene, 1,3,5-trichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,3,5-trichloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 22-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34071

Benzene, 1,3,5-trichloro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialModerate when exposed to heat or flame.

Chemistry & industry

Pharmacology

Biological Half-LifeApproximate half-life of 1,3,5-trichlorobenzene is 8.5 days.
Metabolism/Metabolites · 5 items

1,3,5-Trichlorobenzene is metabolized to chlorobenzene and 2,4,6-tichlorophenol in rabbits ... . /From table/

In metabolic studies with rabbits using each of the 3 isomeric trichlorobenzenes at 0.5 g/kg ... 1,3,5-trichlorobenzene was least rapidly metabolized. ... Practically no ethereal sulfate or mercapturic acid /was formed/, & only phenol formed was 2,4,6-trichlorophenol.

... Five days after the oral administration of 1,3,5-trichlorobenzene to rabbits, 9% ... of the administered /cmpd/ was excreted as monophenols.

Im injection of approx 50 mg/kg trichlorobenzene to hens resulted in polychlorobenzenes in the yolk in amounts of 2.5 to 6.1% of the admin dose. The egg white contained almost no residue. 1,3,5-Trichlorobenzene was metabolized to 2,4,6-trichlorophenol.

Trichlorobenzene is absorbed via oral, inhalation, and dermal routes. It is believed to be metabolized via cytochrom p-450 enzymes into metabolites that include phenols, mercapturic acid, and catechols.(T38)

Absorption, Distribution and Excretion · 4 items

... 1,3,5-Trichlorobenzene was admin orally to rats at 2 mg/kg, and ... /appeared/ in fat at greater concentration than in liver, kidneys, heart, or blood.

... Five days after the oral administration of 1,3,5-trichlorobenzene to rabbits, 9% ... of the administered /cmpd/ was excreted as monophenols.

All three isomers of trichlorobenzene are absorbed from the gastrointestinal tract, intact skin, and lung.

The tissue distribution and elimination of 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene were examined in male Sprague Dawley rats. Fasted animals were given single doses of 10 mg/kg of the (14)C labeled isomers by gavage. Serial sacrifices were performed at 0.5, 1, and 24 hr and 1, 2, 7, 14, 28, and 56 days post administration. Radioassays utilized the liver, kidneys, spleen, brain, pancreas, lung, heart, thigh muscle, skin, perirenal fat, testes, bladder, adrenals, epididymis, seminal vesicles, prostate, gastrointestinal tract, blood, and salivary glands. The data for each tissue was fitted to a linear compartmental pharmacokinetic model. The amount of (14)C excreted in urine and feces was determined daily for 1,2,3-trichlorobenzene and 1,3,5-trichlorobenzene isomers. Radioactivity from the labeled isomers appeared in the blood and tissues within 30 min of administration, peaked at approximately 4 hr, and slowly declined to background levels. Radioactivity attributed to 1,2,4-trichlorobenzene dropped to background levels after 28 days. The bladder, kidney, fat, skin, liver, and adrenals showed high 1,2,4-trichlorobenzene activity up to 24 hr post treatment. Radioactivity due to 1,2,3-trichlorobenzene dropped to background levels after 56 days for liver, fat, and skin and 28 days for the other tissues. The highest 1,2,3-trichlorobenzene concentrations were found in liver, fat, kidney, and bladder. Significant levels of radioactivity from 1,3,5-trichlorobenzene remained in the tissues after 56 days for all tissues examined. Approximately 85% of the 1,3,5-trichlorobenzene and 92% of the 1,2,3-trichlorobenzene were excreted within 24 hr of dosing. Compartmental analysis showed 1,3,5-trichlorobenzene to have the highest values for the linear coefficients of exponential decay.

Related reactions

29 records
New reaction record
HRID 8401 reaction equation
HRID 8401As reactantuspto-grants-2006_08
HRID 8402 reaction equation
HRID 8402As reactantuspto-grants-2006_08
HRID 131148 reaction equation
HRID 131148As reactantuspto-grants-2008_06
HRID 246049 reaction equation
HRID 246049As reactantuspto-grants-2014_02
HRID 310028 reaction equation
HRID 310028As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 358926 reaction equation
HRID 358926As reactantuspto-grants-1991_03
HRID 365964 reaction equation
HRID 365964As reactantuspto-grants-2000_10
HRID 365965 reaction equation
HRID 365965As reactantuspto-grants-2000_10
Page 1 of 4

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes
Flash Point · 4 items

224.6 °F (NTP, 1992)

107 °C

107 °C /closed cup/

107 °C

Boiling Point · 4 items

407.1 °F at 760 mmHg (NTP, 1992)

208 °C

1,3,5-Trichlorobenzene forms azeotropes with percentages of the following compounds yielding boiling points as listed: 50% camphor, bp 210.5 °C; 43% caproic acid, bp 204.0 °C; 60% m-Cresol, bp 200.5 °C; 40% p-Cresol, bp 200.2 °C; 35% N-Ethylaniline, bp 203.0 °C; Methone (% NA), bp 209.5 °C; 95% Phenol, bp 181.3 °C; p-Toluidine (% NA), bp 199.0. /From table/

208 °C

DecompositionThe substance decomposes on burning producing toxic and corrosive fumes.
Melting Point · 3 items

145 to 147 °F (NTP, 1992)

62.8 °C

63 °C

Physicochemical properties

Melting point
63 °C · 63 °C
Boiling point
208 °C · 208 °C(lit.)
Density
1.4528 · 1.4528 (estimate)
vapor pressure
0.58 at · 0.58 at 25 °C (quoted, Mackay et al., 1982)
refractive index
1.5693 · 1.5693 (estimate)
Flash point
260 °F · 260 °F
storage temp.
0 · 0-6°C
solubility
Soluble in benzene, ether, ligroin (Weast, 1986), glacial acetic acid, carbon disulfide, and petroleum ether (Windholz et al., 1983)
form
powder or crystals
color
Off-White
Water Solubility
Insoluble in water.
Merck
14 · 14,9632
BRN
1635233 · 1635233
Henry's Law Constant
1.83 · 1.83, 2.04, 2.64, 4.49, and 5.24 at 2.0, 6.0, 10.0, 18.0, and 25.0 °C, respectively (EPICS-SPME, Dewulf et al., 1999)
Stability
Stable. Incompatible with acids, strong oxidizing agents.
InChI
1S/C6H3Cl3/c7-4-1-5(8)3-6(9)2-4/h1-3H
InChIKey
XKEFYDZQGKAQCN-UHFFFAOYSA-N
SMILES
Clc1cc(Cl)cc(Cl)c1
LogP
4.19 · 4.190
CAS DataBase Reference
108 · 108-70-3(CAS DataBase Reference)
FDA UNII
2 HS4M0BX3C · 2HS4M0BX3C
NIST Chemistry Reference
1 · Benzene, 1,3,5-trichloro-(108-70-3)
EPA Substance Registry System
1 · 1,3,5-Trichlorobenzene (108-70-3)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07,GHS08,GHS09
Signal word
Warning
Hazard statements
302 · H302-H316-H320-H373-H335-H336-H410
Precautionary statements
501 · P501-P273-P260-P270-P271-P264-P391-P314-P337+P313-P305+P351+P338-P332+P313-P301+P312+P330-P304+P340+P312-P403+P233-P405
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn,Xi
Risk Statements
20 · 20/21/22-36/37/38-38-22-52/53
Safety Statements
26 · 26-36-36/37-61
RIDADR
2321 · UN 2321 (TRICHLOROBENZENES, LIQUID)
WGK Germany
3 · 3
RTECS
2100100 · DC2100100
Hazard Note
Harmful/Irritant
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29039990 · 29039990
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2
Hazardous Substances Data
108 · 108-70-3(Hazardous Substances Data)
Toxicity
200 μg/L · Drinking water standard: No MCLGs or MCLs have been proposed, however, a DWEL of 200 μg/L was recommended (U.S. EPA, 2000).
REACH Registrations
Active
Health Hazards
SYMPTOMS: Symptoms of exposure to this compound include skin, eye and mucous membrane irritation; and hair loss.
Hazards SummaryDanger of cutaneous absorption; [MAK] A skin, eye, and respiratory tract irritant; [ICSC] Causes liver and kidney changes in high-dose animal studies: [HSDB] An irritant; [MSDSonline]
Reactive GroupAryl Halides
Special Reports · 3 items

USEPA; Ambient Water Quality Criteria Doc: Chlorinated Benzenes (1980) EPA 440/5-80-028.

USEPA; Health Assessment Document: Chlorinated Benzenes (1985) EPA-600/8-84-015.

Bobra A et al; Quantitative Structure-Activity Relationships for the Acute Toxicity of Chlorobenzenes to Daphnia magna; Environ Toxicol Chem 4 (3): 297- 305 (1985). The relationships between physical-chemical properties of aqueous solubility, octanol/water partition coefficient, vapor pressure, boiling and melting point, and Henry's Law constants are discussed and illustrated for the chlorobenzenes.

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,3,5-Trichlorobenzene is included on this list. Effective date 10/4/82; Sunset date: 10/4/92.

Reactivity ProfileCan react vigorously with oxidizing materials. (NTP, 1992).
Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Trichlorobenzenes are produced, as an intermediate or final product, by process units covered under this subpart. /The standards apply to all of the isomers and mixtures./

Chemical DangersDecomposes on burning. This produces toxic and corrosive fumes. Reacts with oxidants.
DOT Emergency Guidelines · 5 items

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Trichlorobenzenes, liquid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. ... Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Trichlorobenzenes, liquid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 m (150 ft) for liquids and at least 25 m (75 ft) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Trichlorobenzenes, liquid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Trichlorobenzenes, liquid/

For more DOT Emergency Guidelines (Complete) data for 1,3,5-TRICHLOROBENZENE (8 total), please visit the HSDB record page.

Safety & protection

Fire Fighting · 2 items

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

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

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.

Safe StorageSeparated from strong oxidants. Keep in a well-ventilated room.
Exposure Control and Personal Protection0.5 [ppm]
Fire Fighting Procedures · 2 items

Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.

Water, foam, carbon dioxide, dry chemical.

Storage ConditionsIn general it is unsafe to store oxidizers close to liquids of low flash point. ... Keep all flammables away from an area where oxidizing agents are stored. This storage area should be kept cool and ventilated, and should be fireproof.
Cleanup Methods · 2 items

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

Land spill. Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. Apply universal gelling agent to immobilize spill. Apply appropriate foam to diminish vapor and fire hazard. Water spill. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. Air spill. Apply water spray or mist to knock down vapors. Combustion products include corrosive or toxic vapors.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: You should dampen the solid spill material with acetone, then 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 adsorbent 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.

Disposal Methods · 2 items

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

The following wastewater treatment technology has been investigated for 1,3,5-trichlorobenzene: biological treatment.

Spillage Disposal · 1 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Preventive Measures · 2 items

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. ... Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.

Toxicology

Body Burden · 1 item

1,3,5-Trichlorobenzene has been detected in human blood samples (whole blood) in Canada at a concentration of 4.02 ng/g(1) and in 19% of human adipose tissue at a mean concentration of 126 ng/g(2). Combined trichlorobenzene and tetrachlorobenzene isomers were detected in human adipose tissue in Slovenia at a concentration of 60 ng/g and in human hair samples at 40 ng/g(3). 1,3,5-Trichlorobenzene was detected in human milk in Yugoslavia at concentrations of 0-3 ppb(4) and human milk in Canada at avg concentrations of 0.04 ng/g (whole milk) and 1.4 ng/g (milk fat)(5).

Health EffectsHigh levels of trichlorobenzene may damage the liver, kidney, and thyroid. (A153)
Ecotoxicity Values · 4 items

LD50; Species: Oncorhynchus mykiss (Rainbow trout weight 9.1-43.2 g, length 7.6-9.6 cm); Conditions: freshwater, gavage, 13.3-14.1 °C, pH 8.04-8.21, alkalinity 86 mg/L CaCO3, dissolved oxygen 8.0-10.0 mg/L; Concentration: 39.6 mmol/kg /formulated product/

LD50; Species: Oncorhynchus mykiss (Rainbow trout weight 9.0-30.4 g, length 7.0-9.9 cm); Conditions: freshwater, ip, 13.9-16.2 °C, pH 8.00-8.25, alkalinity 86 mg/L CaCO3, dissolved oxygen 9.1-9.8 mg/L; Concentration: 30.5 mmol/kg /formulated product/

LC50; Species: Poecilia reticulata (guppy); Concentration: 3.3 ppm for 14 days /Conditions of bioassay not specified/

EC50; Species: Tetrahymena pyriformis (Ciliate); Conditions: static, 30 °C; Concentration: 30000 ug/L for 24 hr /formulated product/

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 2.8(2) to 3.82(3), indicate that 1,3,5-trichlorobenzene is expected to have low to no mobility in soil(SRC). Volatilization of 1,3,5-trichlorobenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.89X10-3 atm-cu m/mole(4). However, adsorption to soil is expected to attenuate volatilization(SRC). 1,3,5-Trichlorobenzene is expected to biodegrade slowly in soil with biodegradation half-lives ranging from several weeks to months(5-7).

AQUATIC FATE: Based on a classification scheme(1), log Koc values of 2.8(2) to 3.82(3), indicate that 1,3,5-trichlorobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 1.89X10-3 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 4.6 hours and 5.5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 50 days if adsorption is considered(6). According to a classification scheme(7), BCFs of 150(8) to 14,000(9), suggest bioconcentration in aquatic organisms is high to very high(SRC). 1,3,5-Trichlorobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Biodegradation of 1,3,5-trichlorobenzene is expected to occur slowly, with half-lives ranging from several weeks to months(10-12).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3,5-trichlorobenzene, which has a vapor pressure of 0.24 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3,5-trichlorobenzene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 24 days(SRC), calculated from its rate constant of 6.8X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,3,5-Trichlorobenzene has been shown to be susceptible to direct photolysis by sunlight(4).

Food Survey Values · 1 item

1,3,5-Trichlorobenzene was detected in corn oil at 0.7 ppm and sunflower oil at 0.02 ppm(1). 1,3,5-Trichlorobenzene was detected in leafy vegetables at a concentration of 0.28 ng/g, in fruit at 0.12 ng/g and in eggs/meat at 0.7 ng/g(2). 1,3,5-Trichlorobenzene was detected (concentration in ug/kg) in potato cores (0.0090), potato peels (0.0140), inner part of onions (0.0304), outer onion (0.0488), pea seeds (0.0391) and pea pods (0.159)(3).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Inhalation (T38) ; oral (T38) ; dermal (T38)

Milk Concentrations · 1 item

1,3,5-Trichlorobenzene was detected in human milk in Yugoslavia at concentrations of 0-3 ppb(1) and human milk in Canada at average concentrations of 0.04 ng/g (whole milk) and 1.4 ng/g (milk fat)(2). 1,3,5-Trichlorobenzene was detected in milk at concentrations of 1.2 ng/g(3).

Toxicity SummaryTrichlorobenzene may uncouple mitochondrial oxidative phosphorylation, inducing potassium ion release and inhibiting respiratory control. It's metabolites may covalently bind to cellular proteins and alkylate DNA. (A154, A155)
Ecotoxicity Excerpts · 1 item

/AQUATIC SPECIES/ A test was developed using Tetrahymena pyriformis in order to determine the toxicity of various chemicals. Precultured Tetrahymena pyriformis was exposed for 24 hr at 30 °C to various concn of chemicals, and the number of Tetrahymena pyriformis surviving was then counted. The concn of the chemical, at which the proliferation of Tetrahymena pyriformis was restricted to one-half of the blank test (EC50), was determined. The method, applied to 57 chemicals /including 1,3,5-trichlorobenzene/, demonstrated that it could be used to detect the chemicals at low concn rapidly and with ease. The EC50 values showed a good relationship with 48 hr LC50 values for Himedaka (Oryzias latipes), and could be explained on the basis of the partition coefficient between water and n-octanol.

Animal ConcentrationsSamples of Arctic fox (Alopex lagopus) muscle and liver taken from Barrow, AK, Holman, NT, and Arviat, NU had total chlorobenzene concentrations of 4.2-17.6 ng/g (wet weight), of which 1,3,5-trichlorobenzene is included(1).
Signs and Symptoms · 3 items

Cough. Sore throat.

Redness. Pain.

Trichlorobenzene irritates the eyes and respiratory tract. (T20)

Regulatory information

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,3,5-Trichlorobenzene is included on this list. Effective date 10/4/82; Sunset date: 10/4/92.

Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Trichlorobenzenes are produced, as an intermediate or final product, by process units covered under this subpart. /The standards apply to all of the isomers and mixtures./

Clean Water Act RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Chlorinated benzenes (other than dichlorobenzenes)/
State Drinking Water Guidelines(ME) MAINE 40 ug/l
Federal Drinking Water GuidelinesEPA 40 ug/l

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
DC2100100
ridadr
UN 2321 (TRICHLOROBENZENES, LIQUID)
hs_code
29039990
Toxicity
Drinking water standard: No MCLGs or MCLs have been proposed, however, a DWEL of 200 μg/L was recommended (U.S. EPA, 2000).
risk_code
20/21/22-36/37/38-38-22-52/53
Signal word
Warning
Symbol(GHS)
GHS07,GHS08,GHS09
hazard_code
Xn,Xi
hazard_note
Harmful/Irritant
safety_code
26-36-36/37-61
hazard_class
6.1
Storage Class
11 - Combustible Solids
packing_group
III
Hazard statements
H302-H316-H320-H373-H335-H336-H410
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 2
Precautionary statements
P501-P273-P260-P270-P271-P264-P391-P314-P337+P313-P305+P351+P338-P332+P313-P301+P312+P330-P304+P340+P312-P403+P233-P405
Hazardous Substances Data
108-70-3(Hazardous Substances Data)

Uses & manufacturing

Uses · 6 items

Used as a solvent (degreasing and dyes), dielectric fluid, lubricant additive, emulsifier, and chemical intermediate; [HSDB]

Metal Degreasing [Category: Clean]

Component in trichlorobenzene mixture as dye solvent, degreasing solvent, dielectric fluid, and as lubricant additive

/Manufactured/ and /used/ as an industrial chemical, chemical intermediate, solvent and emulsifier.

1,3,5-Trichlorobenzene is used ... as a termite preparation and insecticide ... /and is/ found as /an/ unintended by-product of the manufacture of mono- and dichlorobenzenes. /SRP: Former use/

Trichlorobenzene is used as a solvent in chemical manufacturing, as well as in dyes, dielectric fluid, synthetic transformer oils, lubricants, heat-transfer medium, and insecticides. (T39)

U.S. Exports(1983) 275,689 pounds
U.S. Imports · 2 items

(1972) 1.3X10+6 G (Principal customs distributors)

(1975) 1.5X10+7 G (Principal customs distributors)

U.S. Production · 3 items

2023: 16,335 lb

(1972) Not produced commercially in US

(1975) Not produced commercially in US

Industry UsesProcessing aids not otherwise specified
Methods of Manufacturing · 3 items

... By Sandmeyer reaction on 3,5-dichloroaniline, by reaction of benzene-1,3,5-trisulfonic acid derivatives with phosgene, by vapor phase chlorination of 1,3-dichlorobenzene, and by chlorination of 3,5-dichloronitrobenzene or 1-bromo-3,5-dichlorobenzene at 300 - 400 °C. The proportion of the 1,3,5-isomer in a mixture can be raised by isomerization of the other trichlorobenzenes with aluminum chloride or by reacting tetrachlorobenzenes and higher chlorobenzenes with alkali metal amides. Total isomerization is reported to occur when SbF5 - HF is used as a catalyst system. The three trichlorobenzenes can be separated by distillation and crystallization.

Prepared from 2,4,6-trichloroaniline by diazotization and treatment with alcohol ... .

Diazotization of 2,4,6-trichloroaniline, followed by treatment with a reducing agent such as hypophosphorous acid.

General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

Benzene, 1,3,5-trichloro-: ACTIVE

Applications · 5 items

DescriptionTrichlorobenzenes (TCBs) are synthetic chemicals that occur in three different isomeric forms. The three chlorinated cyclic aromatic isomers are 1,2,3-trichlorobenzene (1,2,3-TCB), 1,2,4-trichlorobenzene (1,2,4-TCB), and 1,3,5-trichlorobenzene (1,3,5-TCB). 1,2,4-TCB is one of the 188 chemicals designated as a hazardous air pollutant under the Clean Air Act.

Uses1,3,5-Trichlorobenzene is used for someof these applications plus as a termite preparation and insecticide. These compounds are found as unintended by-products of the manufacture of the mono- and dichlorobenzenes.

UsesTrichlorobenzenes are primarily used as solvents in chemical manufacturing industries. 1,2,4-Trichlorobenzene is economically the most important isomer. 1,2,4-Trichlorobenzene is used as a solvent in chemical reactions to dissolve oils, waxes, and resins. Furthermore, it is also used as a dye carrier. 1,2,3- Trichlorobenzene is used as an intermediate for pesticides production, pigments, and dyes. 1,3,5-Trichlorobenzene is not marketed commercially and has very limited use as a chemical intermediate. Besides, trichlorobenzenes can also be used as degreasing agents, as septic tanks and drain cleaners, and as an ingredient in wood preservatives and abrasive formulations. Other minor uses include metal work, anticorrosive paint, and corrosion inhibitor in sprays. In the past, mixed isomers of trichlorobenzenes were used to control termites; however, their use has been discontinued.

Uses1,3,5-Trichlorobenzene is an isomer of 1,2,4-Trichlorobenzene (T774220) which is a solvent in various organic chemical reactions.

General DescriptionWhite to off-white crystals.

Upstream & downstream products

Upstream raw materials

2,4,6-Trichloroaniline1,2,3-Trichlorobenzene1,2,4-Trichlorobenzeneethyl 2-methoxyacrylate1,3-Dibromo-5-chlorobenzene2,2',4,4',6,6'-Hexachlorobiphenyl2,4,6-TrichloroiodobenzenePentachlorobenzene1,2,3,5-TetrachlorobenzeneLindane1-Bromo-3,5-dichlorobenzene

Downstream products

2,4,6-Trichlorobenzoic acid1,2,3-Trichlorobenzene1,2,4-Trichlorobenzene3,5-Dichloroaniline3',5'-Dichloro-2,2,2-trifluoroacetophenone3,5-Dichlorophenol

Additional notes

DefinitionChEBI: 1,3,5-trichlorobenzene is a trichlorobenzene carrying chloro substituents at positions 1, 3 and 5.