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Home > Encyclopedia > 2-Chloro-4-nitrotoluene

2-Chloro-4-nitrotoluene

2-Chloro-4-nitrotoluene structure

2-Chloro-4-nitrotoluene 

structure
  • CAS No:

    121-86-8

  • Formula:

    C7H6ClNO2

  • Chemical Name:

    2-Chloro-4-nitrotoluene

  • Synonyms:

    Benzene,2-chloro-1-methyl-4-nitro-;Toluene,2-chloro-4-nitro-;2-Chloro-1-methyl-4-nitrobenzene;2-Chloro-4-nitrotoluene;3-Chloro-4-methylnitrobenzene;2-Chloro-4-nitro-1-methylbenzene;1-Chloro-2-methyl-5-nitrobenzene;4-Nitro-2-chlorotoluene;2-Chloro-4-nitrophenylmethane;NSC 60111;3-Chloro-4-methyl-1-nitrobenzene;1-Methyl-2-chloro-4-nitrobenzene

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

LIGHT YELLOW CRYSTALLINE POWDER


2-chloro-4-nitrotoluene is a nitrotoluene that is p-nitrotoluene in which one of the hydrogens that is ortho to the methyl group has been replaced by a chlorine. A pale yellow crystalline compound that is insoluble in water but dissolves in most organic solvents, it is used in the manufacture of dyes. It is a member of monochlorobenzenes and a nitrotoluene.

2-Chloro-4-nitrotoluene Basic Attributes

171.58

171.58

1817924

204-501-7

9T26LNR6T8

60111

DTXSID3026984

NEEDLES FROM ALCOHOL

29049090

Characteristics

45.8

3.247 (est)

light yellow crystalline powder

1.3246 (rough estimate)

68 °C

260 °C @ Press: 760 Torr

150 °C

1.5470 (estimate)

H2O: 49 mg/L (20 ºC);acetonitrile: soluble

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

0.0243mmHg at 25°C

Oral-rat LD50: 3020 mg/kg

Combustible, decomposes toxic chloride, nitrogen oxide gas when burning

Safety Information

III

6.1

UN 3457 6.1/PG 3

2

22-36/37/38-20/21/22-52/53

36/37/39-26-61

XS9100000

Xn,N

The warehouse is ventilated, low-temperature and dry; stored and transported separately from food raw materials and oxidants

Stable under normal temperatures and pressures.

P305 + P351 + P338

H302-H319

|Warning|H302 (82.98%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P391, and P501|Aggregated GHS information provided by 47 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. 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. /Chloronitrotoluenes; Chloronitrotoluenes, liquid; Chloronitrotoluenes, solid/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chloronitrotoluenes; Chloronitrotoluenes, liquid; Chloronitrotoluenes, solid/|/GUIDE 152: SUBSTANCES - TOXIC (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 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Chloronitrotoluenes; Chloronitrotoluenes, liquid; Chloronitrotoluenes, solid/|/GUIDE 152: SUBSTANCES - TOXIC (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. /Chloronitrotoluenes; Chloronitrotoluenes, liquid; Chloronitrotoluenes, solid/|For more DOT Emergency Guidelines (Complete) data for 2-CHLORO-4-NITROTOLUENE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The major hazards encountered in the use and handling of 2-chloro-4-nitrotoluene stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal contact), exposure to this crystalline substance may occur from its production and use as a dye intermediate. Effects from exposure may include headache, weakness, dizziness, nausea, tachycardia, and methemoglobinemia. In activities and situations where over-exposure may occur, wear a positive pressure self-contained breathing apparatus and protective clothing. If contact should occur, immediately flush exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. Contaminated clothing and shoes should be removedat the site. While 2-chloro-4-nitrotoluene does not ignite easily, it may burn with the production of irritating or poisonous gases. For fires involving 2-chloro-4-nitrotoluene, extinguish with dry chemical, CO2, water spray, fog, or regular foam. For small dry spills, use a clean shovel (liquid solutions are taken up with sand or other noncombustible absorbent) and place into a clean, dry, loosely covered container for later disposal. Large liquid spills and runoff from fire control water should be diked far ahead for later disposal.

Toxicity

moderately toxic

Persons with blood disorders may be at increased risk from exposure. /Nitrotoluene/

2-Chloro-4-nitrotoluene may be released to the environment during its production and use as a dye intermediate(1,SRC).

TERRESTRIAL FATE: The estimated Koc of approximately 1,391(1,SRC) indicates that 2-chloro-4-nitrotoluene would probably have slow soil mobility(2,SRC). No data are available regarding biodegradation or other chemical processes in soil(SRC).|AQUATIC FATE: If released to water, volatilization may be a significant loss process; however, the reaction may be slow (half-life of 32 hrs from a model river)(1,SRC). Based on the estimated Koc of about 1,391, 2-chloro-4-nitrotoluene may partition from the water column to sediment(SRC). Based on an estimated BCF of 173(1,SRC), 2-chloro-4-nitrotoluene may bioconcentrate in aquatic organisms(SRC). Photolysis in water may be significant; 2-chloro-4-nitrotoluene does absorb UV light >290 nm(2). However, no rate data were located. Hydrolysis is not expected to be an important fate process in aquatic systems(SRC).|ATMOSPHERIC FATE: Vapor-phase 2-chloro-4-nitrotoluene is degraded slowly in the ambient atmosphere by reaction with photochemically formed hydroxyl radicals; the half-life for this reaction in typical air can be estimated to be about 48 days(1,SRC). Photolysis in air may be significant; 2-chloro-4-nitrotoluene does absorb UV light >290 nm(2). However, no rate data were located.

The rate constant for the vapor-phase reaction of 2-chloro-4-nitrotoluene with photochemically produced hydroxyl radicals has been estimated to be 3.35X10-13 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 48 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Photolysis may be significant; 2-chloro-4-nitrotoluene does absorb UV light >290 nm(2). However, no rate data were located. Halogenated aromatics and nitro aromatics are generally resistant to hydrolysis(3); therefore, hydrolysis is not expected to be significant(SRC).

Based on an estimated log Kow of 3.247(2), the bioconcentration factor (BCF) for 2-chloro-4-nitrotoluene can be estimated to be about 173 from a recommended regression-derived equation(1,SRC). This BCF value suggests that bioconcentration in aquatic organisms may be important(SRC).

Based on an estimated log Kow of 3.247(2) and a recommended regression derived equation(1), a Koc value of 1,390 can be estimated for 2-chloro-4-nitrotoluene(SRC). This Koc value suggests low soil mobility(3).

The Henry's Law constant for 2-chloro-4-nitrotoluene can be estimated to be approximately 4.06X10-5 atm-cu m/mole at 25 °C using a chemical structure estimation method(2,SRC). This value of Henry's Law constant suggests that volatilization from water may be slow but possibly significant(1). Based on this value, the volatilization half-life of 2-chloro-4-nitrotoluene from a model river 1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec has been estimated to be approximately 32 hrs(1,SRC).

Workers involved in the use of 2-chloro-4-nitrotoluene as a dye intermediate may be exposed through inhalation of vapors or through eye and skin contact(1,SRC).

Drug Information

... The onset of symptoms of methemoglobinemia is insidious and may be delayed up to 4 hours; headache is commonly the first symptom and may become quite intense as the severity of methemoglobinemia progresses. ... Cyanosis develops early in the course of intoxication, first the lips, the nose, and the ear lobes, and is usually recognized by fellow workers ... Until the methemeglobinemia concentration approaches approximately 40%, the individual usually feels well, has no complaints, and will insist that nothing is wrong. ... Over 40% ... weakness and dizziness; at up to 70% ... there may be ataxia, dyspnea on mild exertion, tachycardia, nausea, vomiting, and drowsiness. /Nitrotoluene/

2-Chloro-4-nitrotoluene Use and Manufacturing

Methods of Manufacturing

The preparation method is to add p-nitrotoluene to the reaction kettle, and then add the catalyst anhydrous ferric chloride and iodine, start stirring, heat the reaction material to 55~70℃, pass chlorine gas for reaction, and use gas phase for sampling Chromatographic tracking analysis, reaching the end point, stopping the ventilation of chlorine, keeping it for 1h, then washing with water, leaving it to separate into layers, to obtain 3-chloro-4-methylnitrobenzene, and crystallization to obtain the finished product.

Uses

2-Chloro-4-nitrotoluene is a substituted toluene used in the preparation of wide range of compounds such as herbicides, analgesics and

Benzene, 2-chloro-1-methyl-4-nitro-: INACTIVE

DETERMINATION OF 2-CHLORO-4-NITROTOLUENE IN AIR BY THIN LAYER CHROMATOGRAPHY.

Computed Properties

Molecular Weight:171.58
XLogP3:3.4
Hydrogen Bond Acceptor Count:2
Exact Mass:171.0087061
Monoisotopic Mass:171.0087061
Topological Polar Surface Area:45.8
Heavy Atom Count:11
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Nitric acid

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