102-06-7NC(=Nc1ccccc1)Nc1ccccc1OWRCNXZUPFZXOS-UHFFFAOYSA-N1,3-diphenylguanidine is a white to cream-colored chalky powder. Bitter taste and slight odor.
Plastics & Rubber -> Rubber Additives
Rubber
log Kow = 2.89 /Estimated/
1.69
2.85
1.13 at 68 °F (NTP, 1992) - Denser than water; will sink
1.13 g/cu cm at 20 °C
1.19 g/cm³
1.13 @ 20°C
Monoclinic needles (crystalized from alcohol and toluene)
White powder
less than 1 mg/mL at 70 °F (NTP, 1992)
Soluble in ethanol, carbon tetrachloride, chloroform, toluene; very soluble in ethyl ether.
In water, 1,000 mg/L at 25 °C
Solubility in water at 20 °C: poor
29.5 [ug/mL] (The mean of the results at pH 7.4)
安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Danger
H301 (34%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Chemical: Guanidine, N,N'-diphenyl-
Guanidine, N,N'-diphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Guanidine, N,N'-diphenyl- 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)
REACH registered substance: 1,3-diphenylguanidine (EC: 203-002-1)
Diphenylguanidine: Does not have an individual approval but may be used under an appropriate group standard
This chemical is combustible. (NTP, 1992)
Combustible.
SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and respiratory tract. Other symptoms include tearing, reddening and swelling of the skin and eyes; skin sensitization (with possible blistering) and dermatitis. Inhalation may result in runny nose, dry throat, sneezing, coughing and chest discomfort. Ingestion may result in nausea, vomiting and diarrhea. Conjunctivitis may occur. Eye contact may also cause punctuate corneal epithelial defects and edema of the lids and conjunctiva.
/Following a single iv dose of 15.5 umol/kg (14C)-DPG to rats/ ... the nature of the (14C)-DPG derived radioactivity excreted in urine and bile was examined by direct HPLC analysis. Bile contained only small amounts of parent compound at all time points examined. Most of the radioactivity in bile (95%) was in the form of a major metabolite (Peak II) of DPG with traces of another metabolite (Peak I). The major metabolite (Peak II) excreted in bile was resistant to hydrolysis by arylsulfatase, by strong acid, or by strong base. However, incubation of this metabolite with b-glucuronidase resulted in near complete hydrolysis to yield metabolite V. It is believe that this metabolite (Peak II) is in the form of a glucuronide, the position of glucuronidation has not been determined.
/Following a single iv dose of 15.5 umol/kg (14C)-DPG to rats/ ... DPG-derived radioactivity excreted in feces was primarily (94%) in the form of metabolite V. Therefore, it appears that the glucuronide present in bile (Peak II) was subsequently hydrolysed in the intestine, most probably by intestinal flora, to release metabolite V which accounted for most of the radioactivity excreted in feces. HPLC analysis of urine indicated that around 28% of the radioactivity excreted in urine was in the form of parent compound. The major metabolite (Peak II) in urine accounted for approximately 37% of the total radioactivity. Treatment of this metabolite with b -glucuronidase resulted in its hydrolysis t o yield metabolite V.
/Following a single iv dose of 15.5 umol/kg (14C)-DPG to rats/ ... Comparison of excretion in bile versus feces indicates that as much as 30% of the total dose is reabsorbed from the intestine after excretion in bile. Since most of this material is metabolite V, reabsorption from the intestine and reconjugation may account for most of the metabolite II excreted in urine. Two other metabolites were detected in urine. Metabolite III which eluted from the column shortly after peak II accounted for approximately 32% of the radioactivity while the unconjugated metabolite V accounted only for 3% of the radioactivity.
/Following a single iv dose of 15.5 umol/kg (14C)-DPG to rats/ ... radioactivity extracted from lung, skin, and adipose tissue at the 45-min and 2-hr time points was present only in the form of the parent compound. The radioactivity extracted from other tissues at the 24-hr time point was insufficient for accurate metabolite determination.
現在のフィルター条件では反応記録がありません。
読み込み中…
102-06-7DTXSID3025178CHEMBL77675CHEBI:144319388 °F (NTP, 1992)
170 °C
Decomposes >338 °F (NTP, 1992)
170 °C (decomposes)
When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
170 °C
化学的特性1,3-diphenylguanidine is a white or cream powder with a slight odour and bitter taste. slightly soluble in water, soluble in ethanol, chloroform, hot benzene, hot toluene, easily soluble in dilute inorganic acids. Used as medium speed accelerator for natural rubber and synthetic rubber, mainly used in the manufacture of tires, rubber plates, rubber shoes and other rubber industrial products.
A mild eye irritant; May affect human reproduction, based on animal studies; [ICSC] Based on animal studies, a mild eye irritant, but not a skin irritant; Metabolized quickly and eliminated in urine and feces; Has effects on liver and nervous system in feeding studies; Not genotoxic; Not teratogenic; Fetotoxic at maternotoxic doses; [Reference #2]
DHHS/NTP; NTP Technical Report on Toxicity Studies of 1.3-Diphenylguanidine Administered in Feed to F344/N Rats and B6C3F1 Mice. Toxicity Rpt Series No. 42 NIH Publication No. 95-3993 (1995)
The U.S. high production volume (HPV) chemicals are those which are manufactured in or imported into the United States in amounts equal to or greater than one million pounds per year. Robust Summaries include health effects, ecotoxicity data, and environmental fate information for selected chemicals. EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Available from: http://www.epa.gov/chemrtk/viewsrch.htm on 1,3-Diphenylguanidine as of November 3, 2004.
1,3-DIPHENYLGUANIDINE behaves as an amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. This chemical is incompatible with strong oxidizers. (NTP, 1992)
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
In case of fire in the surroundings, use appropriate extinguishing media.
Fresh air, rest.
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.
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.
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.
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
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.
EC50 Daphnia magna (Water flea; immobilization)17 mg/L 48 hr /Conditions of bioassay not specified in source examined/
LC50 Oryzias latipes (Medaka) 10 mg/L 48 hr Static or semi-static
LC50 Lepomis macrochirus (Bluegill) 9.6 mg/L 96 hr, Static
LC50 Oncorhynchus mykiss (Rainbow trout) 11 mg/L 96 hr, Static
LC50 Pimephales promelas (Fathead minnow) 4.2 mg/L 96 hr, Static
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5,900(SRC), determined from a structure estimation method(2), indicates that N,N'-diphenylguanidine is expected to be immobile in soil(SRC). Volatilization of N,N'-diphenylguanidine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.1X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(3). N,N'-Diphenylguanidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.4X10-6 mm Hg(SRC), determined from a fragment constant method(4). N,N'-diphenylguanidine reached 0% of its theoretical BOD in 2 weeks using an activated sludge and the Japanese MITI test(5), indicating that biodegradation in soil is not an important environmental fate process(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5,900(SRC), determined from a structure estimation method(2), indicates that N,N'-diphenylguanidine is expected to adsorb to suspended solids and sediment(SRC). The pKa of N,N'-diphenylguanidine is 10.12(3), indicating that this compound will primarily exist in cation form in the environment and cations generally adsorb more strongly to suspended solids and sediment than their neutral counterparts(4). N,N'-Diphenylguanidine will exist almost entirely as a cation at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(5), BCFs of <2 and <20(6) suggest the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation rates of 18% and 9% in river water and sea water, respectively, after a 3-day cultivation period(7), indicates that biodegradation in water may not be an important environmental fate process(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N'-diphenylguanidine, which has an estimated vapor pressure 8.4X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases. Vapor-phase N,N'-diphenylguanidine 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 4.5 hours(SRC), calculated from its rate constant of 8.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase N,N'-diphenylguanidine may be removed from the air by wet and dry deposition(SRC).
Redness. Pain.
Abdominal pain.
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=102-06-7]
Using a structure estimation method based on molecular connectivity indices(1), the Koc for N,N'-diphenylguanidine can be estimated to be 5,900(SRC). According to a classification scheme(2), this estimated Koc value suggests that N,N'-diphenylguanidine is expected to be immobile in soil. The pKa of N,N'-diphenylguanidine is 10.12(3), indicating that this compound will primarily exist in the protonated form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(4).
/SIGNS AND SYMPTOMS/ Occupational accidental exposure of workers to /n,n'-diphenylguanidine/ (DPG) can cause burning of the eyelids, reddening of the eyes, a bitter taste in the mouth and a painful sensation in the esophagus; flabbiness of the gums and a reduction in the acidity of the gastric juice, tending to achylia, were also reported.
/HUMAN EXPOSURE STUDIES/ /Investigators/ ... found that Spanish agricultural workers with a contact dermatitis had a significantly higher sensitization to 1,3-diphenylguanidine than a contact dermatitis control group working in another profession (11.76% versus 5.32%). The authors attributed this to possible cross-reactions with pesticides, as some of these substances (e.g. Cyprex) are guanidine derivatives and others (e.g. the cyanamides) possess a similar chemical structure.
/HUMAN EXPOSURE STUDIES/ Patch testing of 49 human volunteers with 70 % /n,n'-diphenylguanidine/ (DPG) in petrolatum produced no positive reactions following initial application; 19 of the 49 subjects displayed positive reactions during subsequent exposures. Two subjects displayed positive reactions upon rechallenge 2 weeks later.
/SIGNS AND SYMPTOMS/ Occupational allergic dermatosis was observed in rubber workers and was caused by rubber additives such as diphenylguanidine.
/SIGNS AND SYMPTOMS/ Workers (29-58 years old) occupationally exposed for 3-15 years to /n,n'-diphenylguanidine/ DPG were /examined/; 30 % of the examined subjects different complaints were reported, mostly gastritis, cholangitis, cholecystitis, neurological disturbances and dermatitis; beside these symptoms in some patients bronchial asthma, rhinitis, neuropathy, polyathritis, hypertonia and lithiasis were diagnosed and the liver function was disturbed: changes in the protein metabolism and increased bilirubin levels.
N,N'-Diphenylguanidine, present at 100 mg/L, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1). N,N'-Diphenylguanidine present at 20 mg/L in river water or sea water was 18% and 9% degraded, respectively, after a 3-day cultivation period(2). Therefore this compound is not expected to biodegrade rapidly.
The enzymic C-oxygenation of N,N'-diphenylguanidine (DPG) to N-(4-hydroxyphenyl)-N'-phenylguanidine (4HPG)... is reported. ...Rat and rabbit liver homogenates (9000 g supernatant and microsomes) were used as enzyme source. The enzymic oxygenations were both O2 and NADPH dependent. NADPH could not be replaced by hydrogen peroxide.
6MRZ85RNHQ
DIPHENYLGUANIDINE
Established Pharmacologic Class [EPC] - Standardized Chemical Allergen
Physiologic Effects [PE] - Increased Histamine Release
Physiologic Effects [PE] - Cell-mediated Immunity
Chemical Structure [CS] - Allergens
A chronic experiment with rabbits established that diphenylguanidine after entering the blood is absorbed by all body tissues with its predominant location in the kidneys and liver.
/1,3-Diphenylguanidine/ (DPG) is rapidly absorbed and distributed throughout the body tissues: 30 min after administration of 100 mg DPG/kg bw, the substance was found in the blood; in an hour it was discovered in all the visceral organs; after 24 hours, it was found in the urine. DPG excretion with the urine had ceased on the day 6.
Major organ and tissue volumes were sampled for radioactive content at various time points following iv administration of a 15.15-umol/kg (14C)-/n,n'-diphenylguanidine/ (DPG) dose. Initially the highest concentration (% total dose/g tissue) of DPG-derived radioactivity was observed in liver followed by kidney and lung. The peak concentration in liver was reached in 45 min after administration whereas the DPG-derived radioactivity in other tissues with the possible exception of testes and adipose tissues showed a decline. The concentration of DPG-derived radioactivity in liver was higher than in other tissues at every time point examined. At 24 hr post-exposure the concentration of DPG in liver was 5-10 times higher than in most other tissues. Interestingly, the brain and most lean tissues contained similar concentrations of DPG-derived radioactivity at comparable time points.
The distribution of radioactivity in rat tissues at various time points following a single iv dose of (14C)-DPG of 15.15 umol/kg is presented. DPG-derived radioactivity was readily cleared from all tissues so that within 24 hr after exposure the total tissue burden was approximately 10-fold lower than that observed at the earliest time point, 15 min.
For more Absorption, Distribution and Excretion (Complete) data for N,N'-DIPHENYLGUANIDINE (9 total), please visit the HSDB record page.
Used as a vulcanization accelerator, an activator for other rubber accelerators, and a primary material for standardizing acids; [HSDB] Formerly was contained in Carbamix used to patch test for allergic contact dermatitis; Workers may be exposed to rubber items in homemaking and in the metal, health, laboratory, and building industries; [Kanerva, p. 1789]
Primary material for standardizing acids; free base and phthalate as accelerators for vulcanization of rubber.
Vulcanization accelerator for natural and synthetic rubbers.
Activator for other rubber accelerators.
(1979) No Data
(1981) No Data
(1979) 1.76X10+8 GRAMS (PRINCPL CUSTMS DISTS)
(1981) 8.88X10+8 GRAMS (PRINCPL CUSTMS DISTS)
2023: 2,500,000 - <4,000,000 lb
Guanidine, N,N'-diphenyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1981) PROBABLY GREATER THAN 4.54X10+5 GRAMS
The expected production volume of 1,3-Diphenylguanidine in year 2000 is ... 2400 tonnes/year in the USA.
Treatment of aniline with cyanogen chloride.
... DPG ... /is/ prepared by reaction of cyanogen chloride with aniline ... in a molar ratio of 1:2.
Reaction of cyanogen chloride with an aqueous solution of aniline followed by neutralization with sodium hydroxide; reaction of N,N'-diphenylthiourea with ammonium hydroxide in the presence of a catalyst, eg, potassium hydroxide & lead oxide
Other (requires additional information)
Guanidine, N,N'-diphenyl-: ACTIVE
Promoted lettuce seed germination.
The expected production volume of 1,3-Diphenylguanidine in year 2000 is 2400 tonnes/year in Europe, 2400 tonnes/year in the USA, an amount of 5300 tonnes/year for Asia and 11100 tonnes per year for the world.
用途有機合成原料、ゴムの加硫加速剤。
用途有機ゴム薬品(加硫促進剤)
使用1,3-Diphenylguanidine is used as pharmaceutical intermediate.
一般的な説明White to cream-colored chalky powder. Bitter taste and slight odor.
純化方法1,3-Diphenylguanidine [102-06-7] M 211.3, m 148o, 10.12. Crystallise it from toluene,
定義ChEBI: 1,3-diphenylguanidine is guanidine carrying a phenyl substituent on each of the two amino groups. It is used as an accelerator in the rubber industry. It has a role as an allergen.