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1,3-Diphenylguanidine(CAS No. 102-06-7)

1,3-Diphenylguanidine C13H13N3 (cas 102-06-7) Molecular Structure

102-06-7 Structure

Identification and Related Records

【Name】
1,3-Diphenylguanidine
【CAS Registry number】
102-06-7
【Synonyms】
N,N-diphenylguanidine (sym.)
DPG
Accelerator D
N,N-Diphenylguanidine
Melaniline
Dephenyl Guanidine
sym-diphenylguanidine
n,n'-diphenylguanidine
vanaxdpg
timtec-bbsbb000514
1,3-difenylguanid
1,3-diphenyl-guanidin
acceleratord
acceleratord
akrochemdpg
denax
denaxdpg
dfg
dpg accelerator
dpgaccelerator
dwufenyloguanidyna
dynamine
guanidine, 1,3-diphenyl-
n,n'-diphenyl-guandine
n,n'-diphenyl-guanidin
nci-c60924
【EINECS(EC#)】
203-002-1
【Molecular Formula】
C13H13N3 (Products with the same molecular formula)
【Molecular Weight】
211.26
【Inchi】
InChI=1/C13H13N3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H,(H3,14,15,16)
【InChIKey】
OWRCNXZUPFZXOS-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC=C(C=C1)NC(=NC2=CC=CC=C2)N
【MOL File】
102-06-7.mol

Chemical and Physical Properties

【Appearance】
White to cream-colored chalky powder
【Density】
1.13
【Melting Point】
146-151℃
【Boiling Point】
338.5 °C at 760 mmHg
【Vapour】
1.7E-05mmHg at 25°C
【Flash Point】
158.5 °C
【Water】
slightly soluble
【Solubilities】
slightly soluble in water
【Color/Form】
Monoclinic needles (crystalized from alcohol and toluene)
White powder
【Stability】
Stable. Combustible. Incompatible with strong oxidizing agents. Moisture sensitive.
【HS Code】
29252000
【Storage temp】
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
【Spectral properties】
MAXIMUM ABSORPTION (ALCOHOL): 251 NM (LOG E= 4.4), 286 NM SHOULDER (LOG E= 1.1)
IR: 8143 (Sadtler Research Laboratories IR Grating Collection)
UV: 396 (Sadtler Research Laboratories Spectral Collection)
NMR: 97 (Sadtler Research Laboratories Spectral Collection)
MASS: 69986 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
【Computed Properties】
Molecular Weight:211.26242 [g/mol]
Molecular Formula:C13H13N3
XLogP3-AA:2.4
H-Bond Donor:2
H-Bond Acceptor:1
Rotatable Bond Count:3
Tautomer Count:2
Exact Mass:211.110947
MonoIsotopic Mass:211.110947
Topological Polar Surface Area:50.4
Heavy Atom Count:16
Formal Charge:0
Complexity:225
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:2
Feature 3D Cation Count:1
Feature 3D Ring Count:2
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:6

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22;R36/37/38;R51/53;R62
【Safety Statements 】
S26;S36/37/39;S61
【HazardClass】
9
【Safety】

Poison by ingestion and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:?HarmfulXn,DangerousN
Risk Statements?:?
R22:Harmful if swallowed.;
R36/37/38:Irritating to eyes, respiratory system and skin.;
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.;
R62:Possible risk of impaired fertility.;
Safety Statements?:?
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.;
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.;
S61:Avoid release to the environment. Refer to special instructions / Safety data sheets.;
RIDADR: UN 3077 9/PG 3

【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
1,3-diphenylguanidine is irritating to the eye and non-irritating to the skin.
【Transport】
UN 3077
【Other Preventative Measures】
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.
【Protective Equipment and Clothing】
1,3-diphenylguanidine is irritating to the eye and non-irritating to the skin.
【Specification】

?1,3-Difenylguanid , with CAS number of 102-06-7, can be called 1,3-Diphenylguanidine ; Dwufenyloguanidyna ; Diphenylguanidine ; DPG accelerator ; Guanidine, N,N'-diphenyl- ; Guanidine, 1,3-diphenyl- ; N,N'-Diphenylguanidine ; s-Diphenylguanidine ; Vulkazit .?It is a white to cream-colored chalky powder. Bitter taste and slight odor.?1,3-Difenylguanid (CAS NO.102-06-7) 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. Besides?1,3-Difenylguanid (CAS NO.102-06-7) is incompatible with strong oxidizers.

【Octanol/Water Partition Coefficient】
log Kow = 2.89 /Estimated/
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

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
U.S. Exports

(1979) ND
(1981) ND
U.S. Imports

(1979) 1.76X10+8 GRAMS (PRINCPL CUSTMS DISTS)
(1981) 8.88X10+8 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production

This chemical is listed as a High Production Volume (HPV) (65FR81686; http://www.epa.gov/opptintr/chemrtk/hpvchmlt.htm). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438; http://www.epa.gov/oppt/iur/index.htm).
(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.
【Usage】

Primary material for standardizing acids, free base & phthalate as accelerators for vulcanization of rubber.

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
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. [Kazarinova NF et al; Gig Sanit 4: 63 (1975)] PubMed Abstract
/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.
Clearance of DPG-derived radioactivity from the tissues followed a biphasic curve. The initial phase of the curve was rapid and accounted for a major portion of the dose. The second component was much slower. The rapid and relatively nonspecific distribution of DPG from blood to the other tissues is well illustrated by the amount of DPG in muscle. Muscle accounts for approximately 50% of the tissue volume of the rat, has no apparent affinity for DPG, and contained approximately 40%, of the DPG dose within 15 min after an iv administration.
One, three, or nine daily doses of (14C)-DPG were administered to groups of three rats each. Rats were sacrificed 24 hr after the last dose. Results of these studies indicated that most DPG-derived radioactivity was readily cleared from all tissues assayed and that DPG concentrations in all tissues except liver were as low or lower after nine daily doses as compared to a single dose. However, a minor portion of the dose in liver was cleared more slowly than observed for other tissues and the concentration of DPG-derived radioactivity in liver increased significantly relative to other tissues as the number of doses increased. Extraction and analysis of the persistent radioactivity from liver demonstrated that it represented metabolites II and III. An analysis for radioactivity covalently bound to liver macromolecules proved negative. Therefore, the mechanism which accounts for the slower clearance of this minor component from liver is unknown.
Total excretion of [14C]DPG-derived radioactivity was determined by daily collection of urine and feces from each animal held from 1 to 3 days. Approximately equal amounts of radioactivity were excreted in both urine and feces and the relative amounts of excretion by these routes were not affected by the dose in the range studied or the route of administration. Approximately 80% of the radioactivity is excreted in urine and feces 24 hr after an iv dose and total excretion approaches 100% in 3 days.
The importance of the feces as a route of DPG elimination indicated that much of the DPG-derived radioactivity might be eliminated in bile. The elimination of DPG in bile was studied by cannulating the common bile duct of anesthetized rats. Approximately 50% of the injected dose was excreted within 2 hr and up to 75% of the total dose excreted in 6 hr. These results indicate that DPG excretion in feces (55% in 3 days) accounts for only a portion of the DPG excreted in bile. That portion of the DPG-derived radioactivity excreted in bile and not excreted in feces most probably undergoes extensive enterohepatic recirculation and is subsequently excreted in urine.
...1,3-Diphenylguanidine (DPG), ...was studied in adult female Sprague-Dawley rats. DPG shows 10% penetration through clipped back skin of rats in 5 days. The first-order dermal absorption rate constant as determined by least square method was 0.021 +/- 0.002 d-1 (T1/2 = 33.6 days). Approximately 13% of the absorbed dose remained in the body in 5 days. Retention in skin, muscle, liver, intestine and fat contributed most to the body burden of DPG-derived radioactivity in 5 days. All tissues showed tissue to blood ratios >1, with liver and intestine ratios of 26 at 5 days. Approximately 61% of the absorbed dose was eliminated into urine and 27% into feces in 5 days... . Within 72 hr, approximately 50% of the DPG-derived radioactivity excreted in the urine was parent compound. After 72 hr, the DPG-derived radioactivity in the urine was present in the form of a single metabolite, and no parent compound was detected. No parent compound was detected in feces. Two metabolites, neither of which occurred in urine, were detected in feces. [Shah PV et al; J Toxicol Environ Health 15 (5): 623-33 (1985)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
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
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 deg 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 deg 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).

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