1,2,4-トリアゾール

1H-1,2,4-Triazole

HCID 9257CAS 288-88-0

基本情報

標準SMILES
c1nc[nH]n1
InChIKey
NSPMIYGKQJPBQR-UHFFFAOYSA-N
分子式
C2H3N3
平均分子量
69.07 g/mol
単同位体質量
69.03269711

名称と識別子

優先名称
1H-1,2,4-Triazole
IUPAC
1H-1,2,4-triazole
現地名
1,2,4-トリアゾール
英語名
1,2,4-Triazole
分子式
C2H3N3
分子量
69.07

名称と別名

1,2,4-TRIAZOLE1H-1,2,4-Triazole288-88-0Pyrrodiazoles-TriazoleDTXSID602713110MS0Y1RDINSC-83128DTXCID207131CHEBI:35550RefChem:908322CHEBI:35560
名称をさらに表示
1,2,4-トリアゾール1,2,4‐トリアゾ-ル1H-1,2,4-トリアゾール1,2,4-1H-トリアゾール1,2,4-1H-トリアゾール(片状)1,2,4‐1H‐トリアゾールCS_MET-13576A-250MG_1,2,4-トリアゾール1H-1,2,4-トリアゾール標準品TRIAZOLETA-4TRIAZOLE(1,2,4-)
206-022-94H-1,2,4-triazole63598-71-01,2,4-1H-TriazoleMFCD000052281H-1,2,4-triazol1,2,4 triazole1,2,4-triazol

データベース識別子

CAS
288-88-0、63598-71-0
PubChem CID
9257
DTXSID
DTXSID6027131
ChEMBL
CHEMBL15571
ChEBI
CHEBI:35550
UNII
10MS0Y1RDI
EC Number
206-022-9
Nikkaji
J5.455K

物性

構造計算による物性

XLogP
-0.6
極性表面積
41.6 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
0
重原子数
5

実験および物理化学的性質

LogP · 2 件

log Kow = -0.58

-0.6

Density640 kg/m³
Color/FormNeedles from benzene/ethanol
Solubility · 2 件

Soluble in water, ethanol

Solubility in water, g/100ml at 20 °C: 125

Flash Point · 2 件

170 °C closed cup

170 °C c.c.

Boiling Point · 2 件

260 °C (decomposes)

260 °C

物理化学的性質

融点
119 · 119-121 °C (lit.)
沸点
260 °C · 260 °C (lit.)
比重(密度)
1.15 g/cm3 · 1.15 g/cm3 (130℃)
蒸気圧
0.215 Pa · 0.215Pa at 20℃
屈折率
1.4854 · 1.4854 (estimate)
闪点
140 °C · 140 °C

化学的性質

化学的特性white crystalline powder and flakes

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral];H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation];H360FD: May damage fertility; May damage the unborn child [Danger Reproductive toxicity]

P203, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P405, and P501 (click each P-code to see the statement)

Danger

危険有害性情報

Regulatory Information · 6 件

Chemical: 1H-1,2,4-Triazole

Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient

Regulation (EC) No 1107/2009 (amended)

1H-1,2,4-Triazole is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-1,2,4-Triazole 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)

1,2,4-Triazole is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

Status: Active Update: 26-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13353

Other Safety InformationIMAP assessments - 1H-1,2,4-Triazole: Human health tier II assessment
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
Fire PotentialCombustible
Hazards SummaryAn eye irritant; Can be absorbed through skin; Animal tests show that this substance possibly causes toxicity to human reproduction or development. [ICSC] An eye irritant; [eChemPortal: ERMA; ESIS] An irritant; [MSDSonline]
EC ClassificationSymbol: Xn; R: 22-36-63; S: (2)-36/37

安全と保護具

Fire FightingUse water spray, powder, foam, carbon dioxide.
First Aid Measures · 4 件

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.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

Safe StorageSeparated from strong oxidants and strong acids. Store in an area without drain or sewer access.
Fire Fighting Procedures · 2 件

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.

Storage Conditions · 2 件

Keep container tightly closed in a dry and well-ventilated place.

Separated from strong oxidants, and strong acids. Store in an area without drain or sewer access.

Cleanup Methods · 2 件

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.

毒性情報

Environmental Fate · 3 件

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).

Adverse Effects · 1 件

Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

Exposure RoutesThe 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.
Signs and SymptomsRedness. Pain.
ICSC Environmental DataThe substance is harmful to aquatic organisms. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.
Soil Adsorption/Mobility · 1 件

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.

法規制情報

Regulatory Information · 6 件

Chemical: 1H-1,2,4-Triazole

Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient

Regulation (EC) No 1107/2009 (amended)

1H-1,2,4-Triazole is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-1,2,4-Triazole 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)

1,2,4-Triazole is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

Status: Active Update: 26-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13353

安全データ

wgk
2
tsca
TSCA listed
rtecs
XZ3806000
毒性
LD50 orally in Rabbit: 1650 mg/kg LD50 dermal Rabbit 3129 - 4200 mg/kg
hs_code
29339990
risk_code
22-36-63-34

化学と産業

薬理情報

Absorption, Distribution and Excretion · 5 件

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.

用途と製造

Uses · 2 件

Used in organic synthesis; [IUCLID]

Intermediate

U.S. Production · 4 件

2023: 5,500,000 - <7,000,000 lb;2022: 7,000,000 - <8,500,000 lb;2021: 4,000,000 - <5,500,000 lb;2020: 4,000,000 - <5,500,000 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#7598]

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.

Consumer UsesIntermediate
Industry UsesIntermediate
Methods of Manufacturing1,2,4-Triazole is made by reaction between hydrazine and formamide. Distillation.
Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
応用分野 · 3 件

解説環内に窒素原子3個をもつ5員環芳香族化合物の総称。1,2,3-トリアゾールと1,2,4-トリアゾールの2種類の環異性体がある。環異性体とは、同じ分子式をもっているが環のヘテロ原子の位置が異なる化合物をいう(図A)。トリアゾールのそれぞれの環異性体には、さらに水素原子がどの窒素原子上に結合しているかという点で異なる互変異性体の存在が可能である。1,2,3-トリアゾールでは1-位置のN上にHがある1H-1,2,3-トリアゾールと、2-位置のN上にHがある2H-1,2,3-トリアゾールの2種類の互変異性体がある(図A)。しかし、実際には水素原子が速やかに窒素原子上を移動するので、これらの互変異性体を別々に分けとることはできない。 1,2,3-トリアゾールは融点23℃、沸点203℃で、甘味のある結晶であり、水、エタノール(エチルアルコール)によく溶ける。医薬品などに広く応用されている。1,2,3-トリアゾールは置換アルキン(R2C≡CH)とアジド化合物(N≡N+N-R1)の[3+2]付加により合成される。この反応をフイスゲン(Huisgen)反応という。しかしこの反応は、触媒を使わないと進行が遅いうえ、異性体混合物(1,4-付加物と1,5-付加物の混合物)を生成するという欠点があった。この反応を銅(Ⅰ)触媒の存在下で行うと、反応は非常に速く進行して選択的に1,4-付加物だけを与えることが、K·B·シャープレスらにより発見された。この改良により、この反応の応用範囲が広まり、代表的なクリック反応として知られるようになった(図B)。さらに、ルテニウム触媒を用いる1,2,3-トリアゾールの合成法も開発された。 1,2,4-トリアゾールは融点120℃、沸点260℃の無色の針状結晶であり、水、エタノールによく溶ける。1,2,4-トリアゾールにも1H-1,2,4-トリアゾールと4H-1,2,4-トリアゾールの2種類の互変異性体がある(図A)。[廣田 穰][参照項目] | 互変異性 | シャープレス | 複素環式化合物 "トリアゾールの異性体〔図A〕 "1,2,3-トリアゾールの合成〔図B〕小学館 日本大百科全書(ニッポニカ) )

用途1,2,4-トリアゾール(1,2,4-Triazole)はトリアゾールと呼ばれるC2H3N3という分子式を持つ化合物の1つで、炭素原子2個と窒素原子1個からなる五員環を持つ。1,2,4-トリアゾールは芳香族性を持つ複素環式化合物である。 フルコナゾールやイトラコナゾールなどの抗真菌薬の骨格となっている。

使用1,2,4-Triazole is present in a large variety of fungicides as C14-demethylase-inhibitors. In addition they are used in synthetic chemical reactions such as the design and preparation of ghrelin receptor ligand antagonists, like JMV 2959.

調製方法 · 1 件

純化方法Crystallise 1,2,4-triazole from EtOH, H2O, EtOAc (m 120.5-121o), or EtOH/*C6H6. The hydrochloride has m 170o, and the picrate has m 163-164o (from H2O or CHCl3). [Barszcz et al. J Chem Soc, Dalton Trans 2025 1986]. [Beilstein 26 H 13, 26 II 6, 26 III/IV 35.]

上流・下流製品情報

サプライヤー13 社

郑州汇聚化工有限公司0371-53399770 18037166334 · [email protected]
毕佳索(上海毕得医药科技股份有限公司)400-6005915 · [email protected]
Aladdin Scientific[email protected]
上海相辉医药科技有限公司13761987713; 13761987713 · [email protected]
台州南峰药物研究所[email protected] 18616377689 · [email protected]
補足説明 · 1 件

定義1,2,4-triazole is a chemical substance with molecular formula C2H3N3, molecular weight 69.07 and CAS No. 288-88-0. Colorless acicular crystal, soluble in water and ethanol. 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. Triazole is an aromatic five membered heterocyclic compound. Its unique structure is conducive to the formation of a variety of non covalent bonds and is easy to promote the binding of proteins, enzymes and receptors, thus showing a wide range of biological pharmacological activities, such as anticancer, antispasmodic, antibacterial, anti HIV. In particular, 1,2,3-triazole has strong thermal stability and acid-base stability, and is not sensitive to redox, hydrolysis and enzymatic degradation. It is often used as a pharmacodynamic group in drug synthesis.

関連反応

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