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Home > Encyclopedia > N,N′-Diethylthiourea

N,N′-Diethylthiourea

N,N′-Diethylthiourea structure

N,N′-Diethylthiourea 

structure
  • CAS No:

    105-55-5

  • Formula:

    C5H12N2S

  • Chemical Name:

    N,N′-Diethylthiourea

  • Synonyms:

    Thiourea,N,N′-diethyl-;Urea,1,3-diethyl-2-thio-;N,N′-Diethylthiourea;1,3-Diethylthiourea;1,3-Diethyl-2-thiourea;Pennzone E;U 15030;N,N′-Diethylthiocarbamide;Thiate H;Accel EUR;Nocceler EUR;NSC 3507;Robac DETU;Rhenogran DETU;Sanceler EUR;Diethylthiourea;Accelerator DETU;Accelerator EUR;27598-95-4

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

white to buff-coloured solidChEBI: Thiourea in which each nitogen carries an ethyl substituent.Buff solid or white powder.


Buff solid or white powder. (NTP, 1992)|DryPowder; PelletsLargeCrystals


Buff solid or white powder. (NTP, 1992)|N,N'-diethylthiourea is thiourea in which each nitrogen carries an ethyl substituent. It has a role as an allergen.

N,N′-Diethylthiourea Basic Attributes

132.23

132.23

773905

203-308-5

J2RDK7O9MZ

3507

DTXSID8020466

BUFF SOLID

29309070

Characteristics

56.2

0.6

Buff solid or white powder. (NTP, 1992)

1,12 g/cm 3

68-71 °C

Decomposes (NTP, 1992)

186 °C

1.5300 (estimate)

H2O: 38 g/L (20 ºC)

Store below +30°C.

1.56mmHg at 25°C

Henry's Law constant of 6.85X10-8 atm-cu m/mole at 25 °C (est)

Decomposes

This material may be sensitive to exposure to air. (NTP, 1992). Slightly soluble in water.

Amides and Imides

N,N'-DIETHYLTHIOUREA is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Safety Information

1759

2

22-40-45-20/21/22

45-36/37-53-24/25

YS9800000

Xn,T

Stable. May be air sensitive. Incompatible with strong oxidizing agents.

P260-P280-P301 + P312 + P330-P305 + P351 + P338 + P310

H302 + H312-H317-H318-H372-H412

DHEW/NCI; Bioassay of N,N-Diethylthiourea for Possible Carcinogenicity (1979) Technical Rpt Series No. 149 DHEW Pub No. (NIH) 79-1705

Flash point data are not available for this chemical, but it is probably combustible. (NTP, 1992)

|Danger|H302 (92.03%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P322, P330, P333+P313, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 280 companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, and P501

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

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 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% 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 60-70% 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. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere and store it under refrigerated temperatures. (NTP, 1992)

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

Toxicity

The effects of combined administration of three carcinogens in male F344 rats were investigated. The analysis of additive or synergistic effects was performed by comparing data for simultaneous and individual treatment at dose levels of one third of the reported TD50 values in rats. 2,4-Diaminoanisole sulfate, N,N'-diethylthiourea, and 4,4'-thiodianiline were administered alone or in combination in the diet at 610, 200, and 46 ppm levels, respectively, for a 52 wk period. The resultant incidence of thyroid adenocarcinomas in the combined treatment group was significantly higher than those in each individual treatment groups, 18/18 versus 0/21 (2,4-diaminoanisole sulfate), 1/21 (N,N'-diethylthiourea), and 2/20 (4,4'-thiodianiline). Hepatocellular carcinomas occurred in 9/18 and lung adenomas in 6/18 of those receiving the combined treatment. Hepatocellular carcinomas occurred in 3/20 and lung adenomas in 4/20 treated with 4,4'-thiodianiline. It was concluded that the three carcinogens exert apparent synergism in thyroid carcinogenesis when administered simultaneously.

LD50 Rat oral 316 mg/kg|LD50 Mouse oral 681 mg/kg

A bioassay for the possible carcinogenicity of N,N'-diethylthiourea was conducted using Fischer 344 rats and B6C3F1 mice. N,N'-Diethylthiourea was admin in the feed, at either of two concn, to groups of 50 males and 50 females of each species. Twenty animals of each sex and species, except for 19 male mice, were placed on test as controls. The high and low dietary concn of N,N'-diethylthiourea were, respectively, 250 and 125 ppm for rats and 500 and 250 ppm for mice. The cmpd was admin in the diet for 103 wk, followed by an observation period of 1 wk for all dosed groups. ... Adequate numbers of animals in all dose groups survived sufficiently long to be at risk from late developing tumors. ... Under the conditions of this bioassay, N,N'-diethylthiourea was carcinogenic to Fischer 344 rats, causing follicular cell carcinomas of the thyroid in males and follicular cell neoplasms of the thyroid in females. There was no evidence for the carcinogenicity of the compound in B6C3F1 mice. ... Levels of Evidence of Carcinogenicity: Male Rats: Positive; Female Rats: Positive; Male Mice: Negative; Female Mice: Negative.

Since N,N-diethylthiourea is used as a corrosion inhibitor in metal pickling solutions and as an accelerator for rubber processing(1), release to the environment may occur during waste disposal from its production and use(SRC).

TERRESTRIAL FATE: The estimated Koc(1,SRC) indicates that N,N-diethylthiourea may be highly mobile in soil(3). The estimated low value for Henry's Law constant(3) suggests that volatilization of N,N-diethylthiourea from moist soil would not be important(SRC).|AQUATIC FATE: Thiourea was found to be stable towards hydrolysis and photolysis(1). Therefore, hydrolysis and photolysis of N,N-diethylthiourea, which is structurally similar to thiourea, may not be important(SRC). Based on the estimated low value of 49(2,SRC) for Koc, adsorption of N,N-diethylthiourea to suspended solids and sediment should not be important and N,N-diethylthiourea should be present mostly in the aquatic phase in water(SRC). The estimated BCF value of 2(2,SRC) indicates that N,N-diethylthiourea would not bioconcentrate in aquatic organisms in water. Based on the estimated value of Henry's Law constant of 6.85X10-8 atm-cu m/mole at 25 °C(3) and the volatility characteristics associated with H(2), volatilization of N,N-diethylthiourea from water would not be important(SRC).|ATMOSPHERIC FATE: Based on an estimation method(1), the rate constant for the reaction of vapor-phase N,N-diethylthiourea with photochemically generated hydroxyl radicals in the atmosphere is 1.06X10-10 cu cm/molecule-sec. Assuming the daily average concn of hydroxyl radicals in the atmosphere of 5X10+5/cu cm(2), the half-life for the reaction would be 4 hrs. Based on a water solubility of 4555 mg/l(SRC) estimated from the experimental log Kow value of 0.57(3) and a regression equation(4), wet deposition may partly remove N,N-diethylthiourea from the atmosphere(SRC). If present in particulate form, N,N-diethylthiourea may also be removed from the atmosphere by dry deposition(SRC).

In tests to assess the environmental hazard of chemicals, thiourea was found to be stable towards hydrolysis and photolysis(1). Therefore, hydrolysis and photolysis of N,N-diethylthiourea, which is structurally similar to thiourea, may not be important(SRC). Based on an estimation method, the rate constant for the reaction of vapor-phase N,N-diethylthiourea with hydroxyl radicals has been estimated to be 1.06X10-10 cu cm/molecule-sec(2,SRC). Assuming the daily average concn of hydroxyl radicals in the atmosphere of 5X10+5/cu cm(3), the half-life for this reaction has been estimated to be 4 hrs(SRC).

Based on a log Kow value of 0.57(1), the BCF for N,N-diethylthiourea can be estimated to be 2 from a regression-derived equation(2). Thus bioconcentration should not be important in aquatic organisms(SRC).

Based upon an experimental value of 0.57 for log Kow(1), the Koc for N,N-diethylthiourea can be estimated to be 49 from a linear regression-derived equation(2,SRC). This estimated Koc suggests that N,N-diethylthiourea will be highly mobile in soil(3,SRC).

The Henry's Law constant for N,N-diethylthiourea can be estimated to be approximately 6.85X10-8 atm-cu m/mole at 25 °C using a chemical structure estimation method(1,SRC). Based on this value and the volatility characteristics associated with Henry's Law constant(2), N,N-diethylthiourea should be less volatile than water(SRC).

Since N,N'-diethylthiourea is used as a corrosion inhibitor in metal pickling solutions and as an accelerator for rubber processing(1), the probable routes of exposure are inhalation of dust and skin absorption of the compound during its production, use and disposal(SRC).|... IT HAS BEEN PRESENT IN ... EPISODES OF SEVERE SUPERFICIAL KERATITIS IN WORKMEN. ... IN MFR OF SYNTH RUBBER, 32 PATIENTS DEVELOPED PAIN, PHOTOPHOBIA, & BLURRING OF VISION ASSOC WITH PUNCTATE EPITHELIAL EROSIONS AFTER WORKING IN PRESENCE OF BLOWING AGENT KNOWN AS GENITRON CR & DIETHYLTHIOUREA.|... MEN ... EXPOSED TO ATMOSPHERE OF LARGE CUPRONICKEL EVAPORATOR WHICH HAD BEEN TREATED WITH SOLN OF SULFAMIC ACID CONTAINING SMALL AMT OF DIETHYLTHIOUREA ... DEVELOPED PAINFUL, SLOW-HEALING SUPERFICIAL KERATITIS SEVERAL HR AFTER EXPOSURE. WHETHER DIETHYLTHIOUREA OR ITS DECOMP PRODUCTS WERE RESPONSIBLE WAS NOT CERTAIN ... .|NIOSH (NOES Survey 1981-1983) has statistically estimated that 7,761 workers are potentially exposed to N,N-diethylthiourea in the USA(1).

Drug Information

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

DIETHYLTHIOUREA HAS BEEN SHOWN TO BE POTENT SKIN SENSITIZER, BUT WHETHER THIS HAS ANY RELATIONSHIP TO POSSIBLE KERATITIS REMAINS TO BE DETERMINED.|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/|Case reports of contact and photocontact sensitivity to dimethylthiourea were described. Four patients, a 24 yr old female textile worker, a 30 yr old female textile cutter, a 35 yr old female textile worker, and a 40 yr old male employed as a draftsman in an architectural firm, developed recurrent itchy dermatitis on the eyelids, nostrils and mouth, which spread to other locations such as the neck and hands. The draftsman became light sensitive, even to exposure to neon light, with episodes occurring soon after he returned to work and continuing for several wk. The patients were patch tested with dimethylthiourea and other thiourea agents which were used in diazo sensitized papers which they used in their work. The three female patients showed contact allergic sensitization to dimethylthiourea. The draftsman showed contact and photocontact allergic sensitization to thiourea. The 24 yr old female patient showed cross sensitization to diethylthiourea and ethylbutylthiourea. All patients changed their jobs. It was concluded that skin problems of these patients have been primarily induced by airborne contact with the allergens.

N,N′-Diethylthiourea Use and Manufacturing

Methods of Manufacturing

Derived from the reaction of ethylamine and carbon disulfide.

Uses

This product is a thiourea accelerator. This type of accelerator is generally obtained by the reaction of amine carbon disulfide. The most commonly used varieties are ethylene thiourea (NA-22) and N,N~"-di-n-butyl thiourea (DBTU )Wait. This kind of accelerator has low promotion efficiency and poor scorch resistance, so it is rarely used for diene rubber, but in some special cases, such as sulphur donor vulcanizing agent such as qiulan mother sulfide At that time, it has the role of active agent. Thiourea accelerators have a unique effect on the vulcanization of neoprene, and they can produce chloroprene vulcanizates with good properties such as tensile strength, hardness, and compression set. Compared with NA-22, diethylthiourea has faster scorch and vulcanization, but the vulcanization flatness is better. The product is easy to disperse and does not spray frost. When the dosage is large, it can be vulcanized at high temperature and high speed, especially suitable for the continuous vulcanization of extruded products. This product is also an accelerator for butyl rubber and a curing agent for EPDM rubber. It can activate thiazole and sulfenamide accelerators in natural rubber and butyl aniline, and has antioxidant effects on natural rubber, chloroprene rubber, nitrile rubber and styrene butadiene rubber. Diethylthiourea is also used to formulate corrosion inhibitor Rodine 31A


Accelerator


Plastic and rubber products not covered elsewhere

Production

(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS|(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

All other chemical product and preparation manufacturing|Thiourea, N,N'-diethyl-: ACTIVE

SALTING OUT CHROMATOGRAPHY APPLIED TO SEPARATION & ANALYSIS OF MIXT OF THIOUREAS & THIOACETAMIDE BY HPLC. THIS METHOD WAS APPLIED TO FIELD SOIL SAMPLES CONTAINING 1,3-DIETHYL-2-THIOUREA.

Computed Properties

Molecular Weight:132.23
XLogP3:0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:132.07211956
Monoisotopic Mass:132.07211956
Topological Polar Surface Area:56.2
Heavy Atom Count:8
Complexity:64.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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