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Home > Encyclopedia > N-(2-Chlorophenyl)thiourea

N-(2-Chlorophenyl)thiourea

N-(2-Chlorophenyl)thiourea structure

N-(2-Chlorophenyl)thiourea 

structure
  • CAS No:

    5344-82-1

  • Formula:

    C7H7ClN2S

  • Chemical Name:

    N-(2-Chlorophenyl)thiourea

  • Synonyms:

    Thiourea,N-(2-chlorophenyl)-;Urea,1-(o-chlorophenyl)-2-thio-;Thiourea,(2-chlorophenyl)-;N-(2-Chlorophenyl)thiourea;(o-Chlorophenyl)thiourea;1-(2-Chlorophenyl)-2-thiourea;1-(2-Chlorophenyl)thiourea;1-(o-Chlorophenyl)thiourea;2-Chlorophenylthiourea;NSC 1165

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

white crystals or powder


Thiourea, (2-chlorophenyl)- appears as needles or plates. Used as an herbicide. Not registered as a pesticide in the U.S. (EPA, 1998)


Thiourea, (2-chlorophenyl)- appears as needles or plates. Used as an herbicide. Not registered as a pesticide in the U.S. (EPA, 1998)

N-(2-Chlorophenyl)thiourea Basic Attributes

186.66

186.66

776946

226-291-6

NEP40W9Y41

1165

2811|2588

DTXSID4063799

NEEDLES OR PLATES

2930909090

Characteristics

70.1

1.20 (Estimated)

Thiourea, (2-chlorophenyl)- appears as needles or plates. Used as an herbicide. Not registered as a pesticide in the U.S. (EPA, 1998)

1.441g/cm3

146 °C

293.1ºC at 760mmHg

131.1ºC

1.727

Sol in alcohol, benzene

The Henry's Law Constant for 2-chlorophenylthiourea can be estimated to be less than 1X10-7 atm-cu m/mole at 25 °C.

No rapid reaction with air. No rapid reaction with water.

Amides and Imides

When heated to decomposition it emits very toxic fumes of chlorides, nitrogen oxides, and sulfur oxides. [EPA, 1998]. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.

Safety Information

II

6.1

2811

28-43-38

45-28A-1-36/37/39-28-22

YS7100000

T+

P261, P264, P270, P272, P280, P301+P310, P302+P352, P321, P330, P332+P313, P333+P313, P362, P363, P405, P501

H300

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P026, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A potential candidate for rotary kiln incineration at a temperature range of 820 to 1600 °C and residence times of seconds for liquids and gases, and hours for solids.

When heated to decomposition it emits very toxic fumes of chlorides, nitrogen oxides, and sulfur oxides. (EPA, 1998)

|Danger|H300 (97.73%): Fatal if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P310, P302+P352, P321, P330, P332+P313, P333+P313, P362, P363, P405, and P501|Aggregated GHS information provided by 44 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: 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. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

(Non-Specific -- Thiourea) Do not touch spilled material; stop leak if you can do it without risk. Small spills: take up with sand or other noncombustible absorbent material and place into containers for later disposal. Small dry spills: with clean shovel place material into clean, dry container and cover; move containers from spill area. Large spills: dike far ahead of spill for later disposal. (EPA, 1998)

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)

P026; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

P026; As stipulated in 40 CFR 261.33, when 1-(o-chlorophenyl)thiourea, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Toxicity

2-Chlorophenylthiourea is not manufactured or used as end-product industrially in the USA(1).

TERRESTRIAL FATE: 2-Chlorophenylthiourea may undergo significant covalent bonding with humic materials in soil which would result in significant adsorption and a chemical conversion to a latent form. If bonding does not occur, significant leaching is possible. Direct photolysis on soil surfaces exposed to sunlight may be possible since 2-chlorophenylthiourea weakly absorbs sunlight. No data are available regarding biodegradation or other chemical degradation processes in soil. (SRC)|AQUATIC FATE: Aquatic volatilization and bioconcentration are not expected to be important with respect to 2-chlorophenylthiourea. 2-Chlorophenylthiourea may undergo significant covalent bonding with humic materials in natural water which would result in significant adsorption and a chemical conversion to a latent form. If bonding does not occur, sorption to humic material in suspended solids and sediments will not be important. Direct photolysis may be possible since 2-chlorophenylthiourea weakly absorbs sunlight. No data are available regarding biodegradation or other chemical degradation processes in water. (SRC)|ATMOSPHERIC FATE: When released to the atmosphere in the vapor-phase, 2- chlorophenylthiourea will degrade rapidly (estimated half-life of 4.3 hr) by reaction with photochemically produced hydroxyl radicals. However, the vapor pressure of 2-chlorophenylthiourea may be low enough to permit a significant fraction of the 2-chlorophenylthiourea released to air to exist in the adsorbed-particulate phase rather than in the vapor-phase. Physical removal from the atmosphere may be possible via wet and dry deposition. (SRC)

The rate constant for the vapor-phase reaction of 2-chlorophenylthiourea with photochemically produced hydroxyl radicals has been estimated to be 89.2X10-12 cu cm/molecule-sec at 25 °C(1,SRC); assuming an average atmospheric hydroxyl radical concn of 5X10+5 molecules/cu cm, the half-life for this reaction is estimated to be 4.3 hours(1,SRC). 2-Chlorophenylthiourea (in a methanol solvent) absorbs UV light in the region between 290-320 nm(1); although the absorbance is relatively weak, there may be a potential for direct photolysis in the environment(SRC).

Based on an estimated log Kow of 1.20(1), the BCF for 2-chlorophenylthiourea can be estimated to be 4.8 from a recommended regression-derived equation(2,SRC). This indicates that environmental bioconcentration is not significant(SRC).

Based on an estimated log Kow of 1.20(1), the Koc for 2-chlorophenylthiourea can be estimated to range from 11-107 using various regression-derived equations(2,SRC); these Koc estimations indicate high to very high soil mobility(3). Although high soil mobility can be predicted from the log Kow value, 2-chlorophenylthiourea may undergo significant adsorption in soil due to a covalent bonding with humic materials(SRC). Secondary amines (such as N-methylaniline) have been observed to undergo covalent bonding with humates(4) an initial rapid (and reversible) bonding phase is followed by a slow reaction (that is not readily reversible) in which the amine compound is chemically altered to yield an amino-substituted quinone(4). This covalent bonding process represents a mechanism in which aromatic amines may be converted to latent form in the biosphere(4).

The Henry's Law Constant for 2-chlorophenylthiourea can be estimated to be less than 1X10-7 atm-cu m/mole at 25 °C using a structure activity relationship estimation method(1,SRC). A Henry's Law Constant of this magnitude indicates that a compound will not volatilize from water(2).

There are no data available which suggest that the general population is exposed to 2-chlorophenylthiourea(SRC).

Drug Information

High oral toxicity. (EPA, 1998)

Note: No information on specific clinical effects of exposure was available. Signs and Symptoms of Thiourea, (2-Chlorophenyl)- Exposure: Signs and symptoms of acute exposure to thiourea, (2-chlorophenyl)-may include dizziness, weakness, headache, and nausea. Esophageal or gastrointestinal tract irritation or burns may also develop. Emergency Life-Support Procedures: Acute exposure to thiourea, (2-chlorophenyl)- may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to thiourea, (2-chlorophenyl)-. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to thiourea, (2-chlorophenyl)-. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove and isolate contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with soap and water. 6. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support to all victims. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. DO NOT induce vomiting or attempt to neutralize! 4. Transport to a health care facility. (EPA, 1998)

In the manufacture of rubber, irritant contact dermatitis may occur from a variety of acids, alkalies, detergents, and solvents used in the process. Allergic contact dermatitis occurs not infrequently and is almost always due to an organic accelerator or antioxidant. While the list of potential sensitizing accelerators and antioxidants is enormous, common allergens include ... thioureas. /Thioureas/

N-(2-Chlorophenyl)thiourea Use and Manufacturing

Methods of Manufacturing

The preparation method is to add o-chloroaniline and water into the reaction pot, then add sulfuric acid dropwise, the temperature is controlled not higher than 50 ℃, react for about 0.5h, then stir for 0.5h, then add ammonium thiocyanate, stir and heat up and reflux for 20h , The reaction is over, filtered and dried to obtain the product.

Uses

O-chlorophenyl thiourea is an intermediate of the herbicide herbicide.

Thiourea, N-(2-chlorophenyl)-: ACTIVE|2-Chlorophenylthiourea is not manufactured or used as end-product industrially in the USA.

Computed Properties

Molecular Weight:186.66
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:186.0018471
Monoisotopic Mass:186.0018471
Topological Polar Surface Area:70.1
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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