1H-1,2,4-Triazole
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1H-1,2,4-Triazole
structure -
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CAS No:
288-88-0
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Formula:
C2H3N3
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Chemical Name:
1H-1,2,4-Triazole
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Synonyms:
1H-1,2,4-Triazole;s-Triazole;4H-1,2,4-Triazole;NSC 83128;3,4-Diazapyrrole;116421-29-5;288-89-1;25167-73-1;27236-77-7;1001118-18-8
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CAS No:
Description
white crystalline powder and flakes
DryPowder|BROWN SOLID IN VARIOUS FORMS WITH CHARACTERISTIC ODOUR.
1H-1,2,4-triazole is a 1,2,4-triazole. It is a tautomer of a 3H-1,2,4-triazole and a 4H-1,2,4-triazole.
1H-1,2,4-Triazole Basic Attributes
69.06530
69.07
206-022-9
10MS0Y1RDI
0682
83128
DTXSID6027131
Needles from benzene/ethanol
2933990090
Characteristics
41.57000
-0.6
1.1 g/cm3
120 °C
270-280 °C
140ºC
1.534
Solubility in water, g/100ml at 20°C: 125
Store at 0-5ºC
0.0203mmHg at 25°C
LD50 orally in Rabbit: 1650 mg/kg LD50 dermal Rabbit 3129 - 4200 mg/kg
May explode on heating.
Henry's Law constant = 1.5X10-6 atm-cu m/mol at 25 °C (est)
When heated to decomposition it emits toxic vapors of NOx|Hydroxyl radical reaction rate constant = 1.0X10-13 cu cm/molec-sec at 25 °C (est)
490 °C
Dust explosion possible if in powder or granular form, mixed with air.
Safety Information
2
R22; R36; R63
S36/37
XZ3806000
Xn
Separated from strong oxidants and strong acids. Store in an area without drain or sewer access.
P201, P202, P264, P270, P280, P281, P301+P312, P305+P351+P338, P308+P313, P330, P337+P313, P405, P501
H302
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material.
Reacts with strong acids and strong oxidants.
European Commission, ESIS; IUCLID Dataset, 1,2,4-Triazole (288-88-0) (2000 CD-ROM edition) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.[Available from, as of September 23, 2010: http://esis.jrc.ec.europa.eu/]
Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P280, P281, P301+P312, P305+P351+P338, P308+P313, P330, P337+P313, P405, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 599 companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P264, P270, P280, P281, P301+P312, P305+P351+P338, P308+P313, P312, P330, P337+P313, P405, and P501
Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Eye protection: Safety glasses|Personal protection: particulate filter adapted to the airborne concentration of the substance.|Protective gloves. Safety goggles.
Combustible
Finely dispersed particles form explosive mixtures in air.|May explode on heating.
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.|Powder, water spray, foam, carbon dioxide.
Accidental Release Measures. Personal precautions: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation. Environmental precautions: Do not let product enter drains. Methods for cleaning up: Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal.|Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|Handle with gloves. Choose body protection according to the amount and concentration of the dangerous substance at the work place.|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|If inhaled, move person into fresh air. If not breathing give artificial respiration Consult a physician. In case of skin contact, wash off with soap and plenty of water. Consult a physician. In case of eye contact, rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed, never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.|Prevent deposition of dust; closed system, dust explosion-proof electrical equipment and lighting.
Causes respiratory tract irritation, skin irritation. and eye irritation.|A skin and eye irritant.
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Separated from strong oxidants and strong acids. Store in an area without drain or sewer access.
A harmful concentration of airborne particles can be reached quickly when dispersed.
The substance is irritating to the eyes.
Animal tests show that this substance possibly causes toxicity to human reproduction or development.
NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
See EFFECTS OF LONG-TERM OR REPEATED EXPOSURE. PREVENT DISPERSION OF DUST! AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!
Use local exhaust or breathing protection.
Protective gloves.
Wear safety goggles.
Toxicity
LD50 Rat oral 1750 mg/kg|LD50 Rat oral 1650 mg/kg bw|LD50 Rat male dermal 4200 mg/kg bw|LD50 Rat female dermal 3129 mg/kg bw|LD50 Mouse oral 1350 mg/kg
1H-1,2,4-Triazole's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a structure estimation method(2), indicates that 1H-1,2,4-triazole is expected to have very high mobility in soil(SRC). Volatilization of 1H-1,2,4-triazole from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1H-1,2,4-Triazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.6 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC, 2010).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a structure estimation method(2), indicates that 1H-1,2,4-triazole is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.5X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 20 and 150 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of -0.58(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1H-1,2,4-Triazole is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data in water were not available(SRC, 2010).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1H-1,2,4-triazole, which has an estimated vapor pressure of 0.6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1H-1,2,4-triazole 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 160 days(SRC), calculated from its rate constant of 1.0X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1H-1,2,4-Triazole contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of 1H-1,2,4-triazole with photochemically-produced hydroxyl radicals has been estimated as 1.0X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 160 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1H-1,2,4-Triazole is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 1H-1,2,4-Triazole contains chromophores that absorb at wavelengths >290 nm(2) and therefore may be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for 1H-1,2,4-triazole(SRC), using a log Kow of -0.58(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1H-1,2,4-triazole can be estimated to be 5(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1H-1,2,4-triazole is expected to have very high mobility in soil.
The Henry's Law constant for 1H-1,2,4-triazole is estimated as 1.5X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1H-1,2,4-triazole is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 20 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 150 days(SRC). 1H-1,2,4-triazole's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1H-1,2,4-Triazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.6 mm Hg(SRC), determined from a fragment constant method(3).
According to the 2006 TSCA Inventory Update Report, the number of workers reasonably likely to be exposed in the industrial manufacturing, processing, and use for 1H-1,2,4-triazole is 1000 or greater persons; the data may be greatly underestimated(1).|Occupational exposure to 1H-1,2,4-triazole may occur through inhalation and dermal contact with this compound at workplaces where 1H-1,2,4-triazole is produced or used. (SRC)
Drug Information
After a single oral administration of 1 mg/kg bw (test substance (14)C-labeled) to male rats (strain not given), approx 100% of the (14)C activity was absorbed from the digestive tract.|8 hr after a single iv administration of 1 mg/kg bw (test substance (14)C-labeled) to male rats (strain not given), approx 50% of the applied radioactivity was detectable in the body of the animals (gastrointestinal tract not considered). 3 days after the application approx 1.5% of the applied activity could be found, and after 6 days the (14)C-activity was no longer measurable (detection limit 0.3%).|Following a single oral or iv administration of 1 mg/kg bw (test substance (14)C-labeled) to male rats (strain not given), approx. 0.1% of the (14)C-activity was exhaled within 30 hr.|1H-1,2,4-Triazole (14)C-labeled was administered to male rats orally (dose: 1 mg/kg bw) or iv (doses: 0.1, 1, 10, 100 mg/kg bw). Within 48 hr after the single application 92-94% of the (14)C-activity was excreted with the urine and 3-5% with the feces, regardless whether the substance was applied orally or iv.|For more Absorption, Distribution and Excretion (Complete) data for 1H-1,2,4-Triazole (6 total), please visit the HSDB record page.
Fresh air, rest.
Remove contaminated clothes. Remove contaminated clothes. 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.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/SIGNS AND SYMPTOMS/ May be harmful if inhaled. Causes respiratory tract irritation. May be harmful if absorbed through skin. Causes skin irritation. Causes eye irritation. Harmful if swallowed.|/SIGNS AND SYMPTOMS/ Effects of short-term exposure: The substance is irritating to the eyes.
1,2,4-triazole
The substance can be absorbed into the body in hazardous amounts by ingestion. The substance can be absorbed into the body by inhalation and through the skin.
Redness. Pain.
1H-1,2,4-Triazole Use and Manufacturing
In the 1L added three-opening bottle 52.9g (0.24 muM) trimethyl protoiodide sulphone, 2.15g (0.014 muM) L - menthol, 6.3g (0.024 muM) triphenylphosphine, 9.6g (0.48 muM) LiOH, 350gTHF, nitrogen protection, stirring cooling to -20 C, dropwise 64.8g compound III of the tetrahydrofuran solution, then completing, -20 C insulation 20h, sampling HPLC detection, compound III 0.03%, compound compound IV 99.8%, ee value 99.3%. The temperature to 20 C, adding 16.5g (0.24 muM) 1, 2, 4 - triazole, thermal insulation 1h, adding 300g water, for 300g * 2 ethyl acetate extraction twice, combined with the organic phase, the organic phase is used for the 300g saturated sodium chloride washing, and organic 20g dried with anhydrous sodium sulfate 2h, filtering to remove the drying agent, the organic phase PH=8, to the organic adds by drops 50g methanesulfonic acid adjusting PH to strongly acidic, a large number of solid precipitation, filtering to obtain yellow solid 78.6g, HPLC purity 99%, yield 89.7%. Taking 23g the above yellow solid, adding 100g THF, stirring cooling to -10 C, solid not soluble, dropping 19.3g triethylamine, dropped exothermic, needs to control the dripped under for the -5 C, dropwise 10.8g a chloride, heat release during the dropping, temperature control of the -5 C, then completing insulation 1h, system by large floc, the heat preservation finishes, no raw material remaining TLC ((Rf raw material=0.6, Rf (reaction solution)=0.7, developing solvent: toluene: ethanol=4:1, volume ratio)), to the system adds by drops 40g 10% of sodium hydroxide solution, canada finishes clear system, thermal insulation 0.5h, liquid, organic uses 80g saturated sodium chloride wash, liquid, organic phase turns on lathe does (0.09 mpa, 50 C) get 18g yellow solid, solid then 20% ethanol solution of recrystallized a, shall be 13.4g white needle crystal compound V, HPLC purity 99.8%, ee value 99.1%, the overall yield 71% (calculated to lactic acid methyl ester).In the 1L added three-opening bottle 52.9g (0.24 muM) trimethyl protoiodide sulphone, 2.15g (0.014 muM) L - menthol, 6.3g (0.024 muM) triphenylphosphine, 9.6g (0.48 muM) LiOH, 350gTHF, nitrogen protection, stirring cooling to -20 C, dropwise 64.8g compound III of the tetrahydrofuran solution, then completing, -20 C insulation 20h, sampling HPLC detection, compound III 0.03%, compound compound IV 99.8%, ee value 99.3%. The temperature to 20 C, adding 16.5g (0.24 muM) 1, 2, 4 - triazole, thermal insulation 1h, adding 300g water, for 300g * 2 ethyl acetate extraction twice, combined with the organic phase, the organic phase is used for the 300g saturated sodium chloride washing, and organic 20g dried with anhydrous sodium sulfate 2h, filtering to remove the drying agent, the organic phase PH=8, to the organic adds by drops 50g methanesulfonic acid adjusting PH to strongly acidic, a large number of solid precipitation, filtering to obtain yellow solid 78.6g, HPLC purity 99%, yield 89.7%. Taking 23g the above yellow solid, adding 100g THF, stirring cooling to -10 C, solid not soluble, dropping 19.3g triethylamine, dropped exothermic, needs to control the dripped under for the -5 C, dropwise 10.8g a chloride, heat release during the dropping, temperature control of the -5 C, then completing insulation 1h, system by large floc, the heat preservation finishes, no raw material remaining TLC ((Rf raw material=0.6, Rf (reaction solution)=0.7, developing solvent: toluene: ethanol=4:1, volume ratio)), to the system adds by drops 40g 10% of sodium hydroxide solution, canada finishes clear system, thermal insulation 0.5h, liquid, organic uses 80g saturated sodium chloride wash, liquid, organic phase turns on lathe does (0.09 mpa, 50 C) get 18g yellow solid, solid then 20% ethanol solution of recrystallized a, shall be 13.4g white needle crystal compound V, HPLC purity 99.8%, ee value 99.1%, the overall yield 71% (calculated to lactic acid methyl ester).
1,2,4-Triazole is one of a pair of isomeric chemical compounds with molecular formula C2H3N3, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,4-Triazole is a basic aromatic heterocycle. 1,2,4-Triazole derivatives find use in a wide variety of applications, most notably as antifungals such as fluconazole and itraconazole.1,2,4-Triazoles can be prepared using the Einhorn–Brunner reaction or the Pellizzari reaction.Unsubstituted 1,2,4-triazole can be prepared from thiosemicarbazide by acyation with formic acid and subsequent cyclization of 1-formyl-3-thiosemicarbazide into 1,2,4-triazole-3(5)-thiol; oxydation of thiol by nitric acid yelds 1,2,4-triazole.The ring structure appears in certain N-heterocyclic carbenes.
Adhesives and sealant chemicals
Adhesives and sealants
1,000,000 - 10,000,000 lb|1H-1,2,4-Triazole 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).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7610]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1H-1,2,4-Triazole. Aggregated National Production Volume: 1 to < 10 million lbs.
Adhesive manufacturing|1H-1,2,4-Triazole: ACTIVE
Environmental transformation -> Pesticide transformation products (metabolite, successor)
1,2,4 triazole is a known environmental transformation product of Bitertanol, Cyproconazole, Difenoconazole, Epoxiconazole, Fenbuconazole, Fluquinconazole, Paclobutrazol, Penconazole, Prothioconazole, Tebuconazole, and Triadimenol.
Computed Properties
Molecular Weight:69.07
XLogP3:-0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:69.032697108
Monoisotopic Mass:69.032697108
Topological Polar Surface Area:41.6
Heavy Atom Count:5
Complexity:28.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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