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ベンゾイミダゾール

Benzimidazole

HCID 5798
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
51-17-2
標準SMILES
c1ccc2[nH]cnc2c1
InChIKey
HYZJCKYKOHLVJF-UHFFFAOYSA-N
分子式
C7H6N2
平均分子量
118.14 g/mol
単同位体質量
118.05309819

概要

Benzimidazole appears as white tabular crystals. (NTP, 1992)

名称と識別子

優先名称
Benzimidazole
IUPAC
1H-benzimidazole
現地名
ベンゾイミダゾール
英語名
Benzimidazole
分子式
C7H6N2
分子量
118.14

名称と別名

BENZIMIDAZOLE51-17-21H-BenzimidazoleBenzoimidazole1,3-BenzodiazoleBenziminazole3-Azaindoleo-BenzimidazoleBenzoglyoxalineAzindole1,3-DiazaindeneN,N'-Methenyl-o-phenylenediamine
名称をさらに表示
ベンゾイミダゾール1,3-ベンゾジアゾール1H-ベンゾイミダゾールN,N'-メテニル-o-フェニレンジアミンベンゾグリオキサリンo-フェニレンホルムアミジンアジンドールベンズイミダゾール1H-ベンズイミダゾール1H-BENZO[D]IMIDAZOLEBenzimidazolBZI1H-BenzoimidazoleTIMTEC-BB SBB004294
NSC 759DTXSID8024573NSC-759E24GX49LD8CHEBI:41275DTXCID704573RefChem:5589CHEBI:36622

データベース識別子

CAS
51-17-2
PubChem CID
5798
DTXSID
DTXSID8024573
ChEMBL
CHEMBL306226
ChEBI
CHEBI:41275
UNII
E24GX49LD8
EC Number
200-081-4
Nikkaji
J2.303E

物性

構造計算による物性補完中

XLogP
1.3
極性表面積
28.7 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
0
重原子数
9
形式電荷
0
複雑度
103

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
pHWeak base
SpringerMaterials PropertiesSchoenflies notation
Pesticides · 2 件

Pesticides -> Fungicides

Environmental transformation -> Pesticide transformation products (metabolite, successor)

LogPlog Kow= 1.32
Color/Form · 3 件

RHOMBIC, BIPYRAMIDAL PLATES IN WATER

Tabular crystals

Othrorombic and monoclinic modifications

Solubility · 4 件

less than 1 mg/mL at 63 °F (NTP, 1992)

Freely soluble in alcohol, sparingly soluble in ether. Practically insoluble in benzene, petroleum ether. One gram dissolves in 2 g boiling xylene. Soluble in aqueous solutions of acids and strong alkalis.

In water, 2.01X10+3 mg/l @ 30 °C

>17.7 [ug/mL] (The mean of the results at pH 7.4)

Boiling Point · 3 件

greater than 680 °F at 760 mmHg (NTP, 1992)

>360 °C

>360 °C

Decomposition

安全と法規制

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。

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 3.9% (6 of 153) of reports.

Warning

H302 (92.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 153 reports by companies from 5 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 3 件

Chemical: 1H-Benzimidazole

Status: Active Update: 09-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/17477

1H-Benzimidazole: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits highly toxic fumes. (NTP, 1992)
Hazards SummaryMay be an irritant; [MSDSonline]
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity Profile · 1 件

An amine. Neutralizes acids to form salts plus water. These acid-base reactions are exothermic. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. May be shock sensitive.

Air and Water ReactionsInsoluble in water.

化学と産業

薬理情報

Mechanism of ActionBenzimidazole prevent tubulin polymerization or spindle movement and their administration can result in aneuploidy.
Metabolism/Metabolites · 3 件

5-HYDROXYBENZIMIDAZOLE IS A MAJOR URINARY METABOLITE OF BENZIMIDAZOLE IN RAT.

SIXTY DAYS AFTER TREATMENT WITH BENZIMIDAZOLE, MELON PLANTS CONTAINED METABOLITES 2-AMINOBENZONITRILE, O-PHENYLENEDIAMINE, ANILINE

Thiabendazole ... Is excreted in the urine as 5-hydroxythiabendazole, conjugated either as the glucuronide or as the sulfate. /Benzimidazoles/

MeSH Pharmacological ClassificationAgents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.
Absorption, Distribution and Excretion · 1 件

Benzimidazoles have only limited solubility in water; consequently, minor differences in solubility tend to have a major effect on absorption. Thiabenzole is rapidly absorbed after oral ingestion ... Most of the drug is excreted in the urine ... as 5-hydroxythiabendazole ... . In contrast tablet forms of mebendazole are poorly and erratically absorbed ... And is extensively metabolized. ... Like mebendazole, albendazole is variably and erratically absorbed after oral administration, although its absorbtion may be increased when it is given with a fatty meal.

用途と製造

Uses · 3 件

The benzimidazoles are a group of systemic fungicides; [HSDB] Classification: agricultural chemical, anthelmintic, anti-infective agent, and experimental pesticide; [ChemIDplus]

Farming (Pesticides) [Category: Industry]

A group of systemic fungicides /Benzimidazoles/

Methods of ManufacturingPrepd by reaction of o-phenylenediamine with formic acid: Wundt, Ber 11, 826 (1878); Wagner, Millett, Org Syn Coll Vol II, 65 (1943).

関連反応

522 件
反応記録を作成
HRID 4310 の反応式
HRID 4310生成物としてuspto-grants-1988_02
HRID 5038 の反応式
HRID 5038反応物としてuspto-grants-1993_09
HRID 7124 の反応式
HRID 7124反応物としてuspto-grants-2006_08
HRID 7126 の反応式
HRID 7126反応物としてuspto-grants-2006_08
HRID 7190 の反応式
HRID 7190反応物としてuspto-grants-2006_08
HRID 16135 の反応式
HRID 16135反応物としてuspto-grants-2010_06
HRID 23311 の反応式
HRID 23311反応物としてuspto-grants-2005_02
HRID 26699 の反応式
HRID 26699反応物としてuspto-grants-1979_04
1 / 66 ページ

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
DANGEROUS; WHEN HEATED TO DECOMPOSITION, IT EMITS HIGHLY TOXIC FUMES.
Melting Point · 2 件

338 to 342 °F (NTP, 1992)

170.5 °C

Vapor Pressure0.0000764 [mmHg]
Physical Description · 2 件

Benzimidazole appears as white tabular crystals. (NTP, 1992)

Solid; Soluble in hot water; [Merck Index] Slightly water solubility = 2 g/L at 20 deg C; [ChemIDplus] Off-white or tan powder; [MSDSonline]

物理化学的性質

融点
169 · 169-171 °C (lit.)
沸点
360 °C · 360 °C
比重(密度)
1.1151 · 1.1151 (rough estimate)
屈折率
1.55 · 1.5500 (estimate)
闪点
360 °C · 360°C
貯蔵温度
30 °C · Store below +30°C.
溶解性
2 g中1g可溶 · キシレン:2g中1g可溶(煮沸)(点灯)
外見
結晶性粉末または結晶
酸解離定数(Pka)
5.532 · 5.532(at 25℃)
色
ベージュからブラウン
水溶解度
難溶性
Merck
14 · 14,1081
BRN
109682 · 109682
Henry's Law Constant
2.7 · 2.7×101 mol/(m3Pa) at 25℃, HSDB (2015)
安定性
安定。可燃性。強力な酸化剤とは相容れない。
InChI
1S/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)
InChIKey
HYZJCKYKOHLVJF-UHFFFAOYSA-N
SMILES
c1ccc2[nH]cnc2c1
LogP
1.32 · 1.320
CAS データベース
51 · 51-17-2(CAS DataBase Reference)
NISTの化学物質情報
1 H-Benzimidazole · 1H-Benzimidazole(51-17-2)
EPAの化学物質情報
Benzimidazole (51-17-2)
化学的性質 · 1 件

化学的特性Benzimidazole is a sheet-like white crystal, with a temperature of 170 ℃, soluble in water and ethanol. Usually used as template compound in the preparation of molecularly imprinted polymer via electropolymerization and electrodeposition of pyrrole on a pencil graphite electrode,and also used in the preparation of benzimidazolium surfactant, 1-hexadecyl-1H-benzimidazole.

Hazard Classes and Categories
Acute Tox. 4 (92.8%)

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

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.

Nonfire Spill Response · 1 件

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.

Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal Protective Equipment (PPE) · 1 件

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

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 108(SRC), determined from a structure estimation method(2), indicates that benzimidazole is expected to have high mobility in soil(SRC). Volatilization of benzimidazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.7X10-7 atm-cu m/mole, using a fragment constant estimation method(3). Benzimidazole is not expected to volatilize from dry soil surfaces, based upon an estimated vapor pressure of 7.6X10-5 mm Hg(SRC), determined from a fragment constant method(4). There is no information on benzimidazole migration in soil, but benzimidazole-based fungicides Benlate and thiabendazole TBZ did not migrate any appreciable distance in soils(5). These fungicides applied to soil surfaces at 100 ug/g did not move more than 25 mm into the soil(5). Benzimidazole was inhibitory to individual strains of soil bacteria that could degrade benzimidazole-based fungicides(6); furthermore, benzimidazole did not support the growth of mixed cultures of microbes that could grow on benzimidazole-based fungicides(7). In contrast, in soil, repeated applications of benzimidazole led to its enhanced degradation(8). These findings suggest that benzimidazole degradation in soils is cometabolic, and that isolation of the appropriate pure cultures that perform the cometabolism has not yet been achieved(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 110(SRC), determined from an estimation method(2), indicates that benzimidazole is not expected to adsorb to suspended solids and sediment in water(SRC). At low pHs, when benzimidazole (pKa = 5.3(8)) exists in a primarily protonated form, it is expected to adsorb to suspended solids and sediments. Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.7X10-7 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 2.1(SRC), from a log Kow of 1.32(6) suggests the potential for bioconcentration in aquatic organisms is low. Benzimidazole is degraded in soils(7), and therefore biodegradation in water may be an important fate process.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzimidazole, which has an estimated vapor pressure of 7.6X10-5 mm Hg at 25 °C(2), is expected to exist in the both the vapor and particulate phases in the ambient atmosphere. Vapor-phase benzimidazole 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 3.6 hours(SRC), calculated from its rate constant of 3.6X10-11 cu cm/molecule-sec at 25 °C(3). Particulate-phase benzimidazole may be removed from the air by wet and dry deposition(SRC). Benzimidazole absorbs light at 245, 271 and 278 nm, and therefore, has little potential for direct photolysis at environmental wavelengths (>290 nm).

Soil Adsorption/Mobility · 1 件

The Koc of benzimidazole is estimated as 110(SRC), using a log Kow of 1.32(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that benzimidazole is expected to have high mobility in neutral and basic soils. Benzimidazole's pKa of 5.3(4) indicates that it will be in the protonated form in acidic environments, and will tend to adsorb to soil particles and clays.

Artificial Pollution SourcesBenzimidazole's production and use as an intermediate in the synthesis of fungal pesticides(1) may result in its release to the environment through various waste streams.
Environmental Biodegradation · 1 件

AEROBIC: No wastewater degradation data for benzimidazole are available(1). Using several different water and soils as sources of inocula, and using benzimidazole as a sole carbon and energy source, no pure cultures of benzimidazole-degraders were found; furthermore, the compound did not support the growth of any bacteria that grew on benzimidazole-based fungicides(2,3). Pseudomonads and Bacillus species (both of which could degrade benzimidazole-based fungicides) were completely inhibited by benzimidazole at concentrations ranging from 500 to 1000 ug/ml, respectively(2). However, in the aerobic soil environment, benzimidazole (10 ug/g) was completely degraded in 10 days when the soils had been pre-exposed to the compound(4). This suggests that benzimidazole biodegradation is cometabolic, and likely occurs in soils as well as in natural waters.

Environmental Bioconcentration · 1 件

An estimated BCF of 2.1 was calculated for benzimidazole(SRC), using a log Kow of 1.32(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.

Volatilization from Water/Soil · 1 件

The Henry's Law constant for benzimidazole is estimated as 3.7X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that benzimidazole is expected to be nonvolatile from water surfaces(2). This Henry's Law constant indicates that benzimidazole is essentially non-volatile(SRC) from moist soils. Benzimidazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.6X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 5 件

...PHENOXYPROPANEDIOL...CAUSED REVERSIBLE FLACCID PARALYSIS IN ANIMALS. ...SIMILAR EFFECTS /FROM/ BENZIMIDAZOLE.../REPORTED/

BENZIMIDAZOLE DID NOT INDUCE REVERSION RESPONSE IN ESCHERICHIA COLI A 46. SALMONELLA TYPHIMURIUM G 46 DISPLAYED A MUTAGENIC RESPONSE. TRANSITION IN VITRO AS WELL AS IN VIVO.

BENZIMIDAZOLE NON-TOXIC TO LUMBRICUS TERRESTRIS WHEN ADMIN ORALLY.

AT CONCN OF 8.5X10-4 MMOLAR BENZIMIDAZOLE FAILED TO STIMULATE TOBACCO CALLUS GROWTH OR SHOOT FORMATION /IN VITRO/. CONCN OF 0.85 MMOLAR & 1.7 MMOLAR INHIBITED KINETIN-DEPENDENT CALLUS GROWTH, WHEREAS LOWER CONCN HAD NO EFFECT.

For more Non-Human Toxicity Excerpts (Complete) data for BENZIMIDAZOLE (6 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of benzimidazole with photochemically-produced hydroxyl radicals has been estimated as 3.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.6 hours(SRC) at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Benzimidazole is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3).

Probable Routes of Human ExposureOccupational exposure to benzimidazole may occur through inhalation and dermal contact with this compound at workplaces where benzimidazole is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 件

Benzimidazole's production and use as a chemical intermediate in the production of agricultural fungicides may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 7.6X10-5 mm Hg at 25 °C indicates benzimidazole will exist in both vapor and particulate phases in the ambient atmosphere. Vapor-phase benzimidazole will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 3.6 hours. Particulate-phase benzimidazole will be removed from the atmosphere by wet and dry deposition. Benzimidazole has little potential for direct photolysis at environmental wavelengths (>290 nm) since it does not absorb light. If released to soil, benzimidazole is expected to have high mobility based upon an estimated Koc of 110. However, a pKa value of 5.3 at 25 °C suggests that at low pH, the protonated form will exist, and will adsorb to organic carbon and clay more strongly than its neutral counterpart. The un-ionized form of benzimidazole will be unlikely to volatilize from soils based upon an estimated Henry's Law constant of 3.7X10-7 atm-cu m/mole and estimated vapor pressure of 7.6X10-5 mm Hg at 25 °C. Benzimidazole is not readily metabolized by isolated soil microbial strains that metabolize benzimidazole-based fungicides, and is inhibitory to some microbes at concentrations ranging from 500 to 1000 ug/g. Hydrolysis of benzimidazole is not expected to occur due to the lack of hydrolyzable functional groups. If released into water, benzimidazole is not expected to adsorb to suspended solids and sediments, based upon its estimated Koc of 108. However, under acidic conditions, due to a pKa of 5.3, adsorption to suspended solids and sediments may occur. The biodegradation of benzimidazole in aquatic systems has not been demonstrated, but it is degraded in soils, which suggests that it will be degraded in waters as well. Volatilization from water surfaces is not expected to be an important fate process, based upon this compound's estimated Henry's Law constant. An estimated BCF of 2.1 suggests the potential for bioconcentration in aquatic organisms is very low. Occupational exposure to benzimidazole may occur through inhalation and dermal contact with this compound at workplaces where benzimidazole is produced or used. (SRC)

Non-Human Toxicity Values · 3 件

LD50 Rat ip 385 mg/kg

LD50 Mouse oral 2910 mg/kg

LD50 Mouse iv 280 mg/kg

安全データ

wgk
3
tsca
TSCA listed
rtecs
DD5425000
毒性
LD50 oral in mouse: 2910mg/kg
hs_code
29339990
risk_code
36/37/38
化審法
(5)-3548
hazard_code
Xi
hazard_note
Irritant
safety_code
37/39-26-24/25
Hazard Classifications
Acute Tox. 4 Oral
ストレージクラス
11 - Combustible Solids
有毒物質データの
51-17-2(Hazardous Substances Data)
Use Classification
Environmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information · 3 件

1H-Benzimidazole: ACTIVE

EFFECTIVE AGENT TO PREVENT TOXIC EFFECT OF AIR POLLUTANTS, SUCH AS OXIDANTS, ON PLANTS.

Not currently registered

応用分野 · 3 件

解説1H-benzimidazole.C7H6N2(118.13).ベンゾイミダゾールは,o-フェニレンジアミンにクロロホルムとアルコール性カリとの作用,またはギ酸と塩酸とともに煮沸することによって得られる.無色の板状晶.融点170 ℃,沸点 > 360 ℃.pKa 5.48.λmax 243,275 nm(ε 6166,3802).エタノール,塩酸,アルカリ水溶液に可溶,冷水,エーテル,ベンゼンに難溶.過マンガン酸カリウムで酸化すると,シュウ酸と少量のイミダゾールジカルボン酸とが得られる.森北出版「化学辞典(第2版)

用途有機合成原料、生理作用研究用。

一般的な説明White tabular crystals.

調製方法

純化方法It crystallises from water or aqueous EtOH (charcoal) and is dried at 100o for 12hours. [Beilstein 23 H 131, 23/6 V 196.]

上流・下流製品情報

上流原料

1,2-フェニレンジアミン1H-Benzimidazole, 1-(phenylmethyl)-1-tosyl-1H-benzo[d]imidazoleN,N-ジエチルホルムアミド2-アミノベンズイミダゾール

下流製品

1H-イミダゾール-4,5-ジカルボン酸2-Acetylbenzimidazole2-(4-チアゾリル)ベンゾイミダゾール2-[2-ヒドロキシ-3-[[(2,3-ジヒドロ-2-オキソ-1H-ベンゾイミダゾール)-5-イル]カルバモイル]-1-ナフチルアゾ]安息香酸ブチル2-[2-ヒドロキシ-3-[[(2,3-ジヒドロ-2-オキソ-1H-ベンゾイミダゾール)-5-イル]カルバモイル]-1-ナフチルアゾ]安息香酸メチルオキサトミドイミダゾールオメプラゾールドンペリドン6-ブロモベンゾイミダゾール5-ニトロベンズイミダゾール1-エチル-1H-ベンゾイミダゾール1-(4-nitrophenyl)-1H-benzimidazole