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ピロール

ピロール 化学構造式
109-97-7
CAS番号.
109-97-7
化学名:
ピロール
别名:
ピロール;ジビニレンイミン;モノピロール;1H-ピロール;アゾール;イミドール;ピロール標準品;ピロル;ピロール, 98+%;ピロール, 50 µg/mL in Toluene
英語化学名:
Pyrrole
英語别名:
AZOLE;Pyrrol;PYRROLE;Pyrrhol;Parzate;IMIDOLE;Pyrroline;FEMA 3386;1H-PYRROLE;Monopyrrole
CBNumber:
CB3852794
化学式:
C4H5N
分子量:
67.09
MOL File:
109-97-7.mol

ピロール 物理性質

融点 :
-23 °C
沸点 :
131 °C(lit.)
比重(密度) :
0.967 g/mL at 25 °C(lit.)
蒸気密度:
2.31 (vs air)
蒸気圧:
8.7 hPa (20 °C)
FEMA :
3386 | PYRROLE
屈折率 :
n20/D 1.508(lit.)
闪点 :
92 °F
貯蔵温度 :
0-6°C
溶解性:
60g/l
酸解離定数(Pka):
15(at 25℃)
外見 :
Liquid
色:
Clear almost colorless to brownish
PH:
>6 (10g/l, H2O, 20℃)
爆発限界(explosive limit):
3.10-14.8%(V)
水溶解度 :
60 g/L (20 ºC)
Sensitive :
Air & Light Sensitive
Merck :
14,8014
JECFA Number:
1314
BRN :
1159
安定性::
Stable. Incompatible with strong acids, strong oxidizing agents. Combustible.
InChIKey:
KAESVJOAVNADME-UHFFFAOYSA-N
CAS データベース:
109-97-7(CAS DataBase Reference)
NISTの化学物質情報:
Pyrrole(109-97-7)
EPAの化学物質情報:
1H-Pyrrole(109-97-7)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  T
Rフレーズ  10-20-25-41
Sフレーズ  26-37/39-45-39-24-16
RIDADR  UN 1992 3/PG 3
WGK Germany  2
RTECS 番号 UX9275000
8-10-23
自然発火温度 550 °C
TSCA  Yes
国連危険物分類  3
容器等級  III
HSコード  29339900
有毒物質データの 109-97-7(Hazardous Substances Data)
毒性 LD50 orally in Rabbit: 137 mg/kg
消防法 危-4-2-III
化審法 (5)-100
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H226 引火性の液体および蒸気 引火性液体 3 警告
H301 飲み込むと有毒 急性毒性、経口 3 危険 P264, P270, P301+P310, P321, P330,P405, P501
H311 皮膚に接触すると有毒 急性毒性、経皮 3 危険 P280, P302+P352, P312, P322, P361,P363, P405, P501
H318 重篤な眼の損傷 眼に対する重篤な損傷性/眼刺激 性 1 危険 P280, P305+P351+P338, P310
H331 吸入すると有毒 急性毒性、吸入 3 危険 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H332 吸入すると有害 急性毒性、吸入 4 警告 P261, P271, P304+P340, P312
注意書き
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P233 容器を密閉しておくこと。
P240 容器を接地すること/アースをとること。
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P270 この製品を使用する時に、飲食または喫煙をしないこ と。
P271 屋外または換気の良い場所でのみ使用すること。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。

ピロール 価格 もっと(34)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01ACSH-229N ピロール
Pyrrole
109-97-7 100mg ¥5500 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01ACSH-229S ピロール
Pyrrole, 50 ug/mL in Toluene
109-97-7 1mL ¥5500 2018-12-26 購入
東京化成工業 P0574 ピロール >99.0%(GC)
Pyrrole >99.0%(GC)
109-97-7 100mL ¥9500 2018-12-04 購入
東京化成工業 P0574 ピロール >99.0%(GC)
Pyrrole >99.0%(GC)
109-97-7 25mL ¥3500 2018-12-04 購入
関東化学株式会社(KANTO) 15771-2A ピロール 99%
Pyrrole 99%
109-97-7 25g ¥3300 2018-12-13 購入

ピロール 化学特性,用途語,生産方法

外観

無色~褐色, 澄明の液体

溶解性

水に微溶 (8g/100g水, 25℃)。有機溶媒に可溶。エタノール及びジエチルエーテルに溶け、水にほとんど溶けない。

用途

亜セレン酸、ケイ酸の検出試薬。亜セレン酸により酸化されてピロール青の濃青色を呈する。リン酸、鉄(3)を共存させ、これを酸化触媒として用いた場合、限界濃度0.1ppm。ケイ酸、モリブデン酸アンモニウム、硫酸の混合溶液は試薬と反応して青色を呈する。

用途

有機合成、腐食防止剤、ポリマーの製造、電解質、溶剤。

使用上の注意

不活性ガス封入

化学的特性

colourless to brown liquid with chloroform odour

化学的特性

Six π-electrons are distributed over the five ring atoms of pyrrole. Delocalization of these electrons stabilizes the ring and the lone pair of electrons on the nitrogen atom, which is responsible for the usual basicity of nitrogen compounds, is involved in the electron cloud, and is not available for sharing. Hence, pyrrole is an extremely weak base and the pyrrolic nitrogen is not readily susceptible to electrophilic enzymic attack (Damani, 1985). There is a high electron density, however, at all positions of the ring, which causes pyrrole to be reactive toward electrophilic substitution. In general, electrophilic substitution reactions on the neutral molecule occur preferentially at the C-2 or C-5 positions (Jones and Bean, 1977; Damani and Crooks, 1982).

化学的特性

Pyrrole has a sweet, warm-ethereal odor reminiscent of chloroform

天然物の起源

The pyrrole ring is the basic unit of the porphyrin system which occurs, for example, in chlorophyll and in hemoglobin. Other pyrrole-based natural products include pigments such as bilirubin and biliverdin, which are degradative products from porphyrins (Sundberg, 1984).
Pyrrole has been found in surface waters and in filtrates from cultures of the blue-green algae, Anabaenaflos aquae. The presence of pyrrole and other organic nitrogen compounds in natural waters is of environmental concern because they may exert significant chlorine demand. Pyrrole is also a precursor to trihalomethane formation (Ram and Morris, 1980).
At ambient temperature, pyrrole can be volatilized from shale oil wastewaters. Concentrations of approximately 3 g/m3 have been measured indoors in air at an oil shale wastewater facility (Hawthorne and Sievers, 1984). Pyrrole has been identified in tobacco smoke, although not in tobacco itself (Johnstone and Plim-mer, 1959); in cigarette smoke (Schumacher et al 1977); in cigar butt aroma (Peck et al 1969); and in Cannabis smoke condensate (Jones and Foote, 1975).
Pyrrole was found to be naturally occurring in foods; in fact, it is on the Food and Drug Administration GRAS (Generally Recognized As Safe) list, with an average usage level of 3 p.p.m. in flavoring formulations (Maga, 1981). Pyrrole is a volatile constituent of roasted coffee (Gianturco et al 1966), roasted peanuts (Walradt et al 1971), and fried chicken (Tang et al 1983). It has also been identified in beef aroma (MacLeod and Coppock, 1976) and is a constituent of cocoa aroma (Marion et al 1967). It should be noted that all the foods listed have undergone some degree of thermal treatment; pyrrole was not present in the fresh, raw foods. In model system studies, pyrrole was among the resulting compounds when hydroxyproline and glucose were heated under nitrogen at temperatures ranging from 120° to 200°C. Large amounts of pyrrole were found, as well, when casein and collagen were pyrolyzed and when proline underwent high temperature pyrolysis (Maga, 1981).

使用

Commercial applications of this compoundare very limited. It is used in organic synthesis.Pyrrole is formed by heating albumin orby pyrolysis of gelatin.

使用

Manufacture of pharmaceuticals.

調製方法

Pyrrole originally was prepared industrially by fractional distillation of coal tar, bone oil or other protein material, and purified through formation of its potassium derivative (Runge, 1834; Michelman, 1925). Later it was produced by heating ammonium mucate with glycerol or mineral oil (Blicke and Powers, 1927; McElvain and Bollinger, 1941). It is now manufactured by addition of ammonia to either acetylene or butadiene. Good yields of pyrrole also may be obtained from the reaction of ammonia with the corresponding heterocyclic compound (furan) in a vapor-phase process at 480° to 500°C, using alumina as a catalyst (Thompson, 1972) or by catalytic reaction of furan with ammonia over a molybdenum or vanadium oxide catalyst at 350-400°C (Bishop and Denton, 1950).

定義

ChEBI: A tautomer of pyrrole that has the double bonds at positions 2 and 4.

定義

pyrrole: An organic nitrogencontainingcompound that formspart of the structure of porphyrins.

製造方法

By fractional distillation of bone oil (bone oil is obtained by destructive distillation of animal bone) and subsequent purification via the corresponding potassium salt; by thermal decomposition of ammonium mucate in glycerol or mineral oil.

Aroma threshold values

Detection: 20 to 49.6 ppm

危険性

Moderate fire risk. Toxic by ingestion and inhalation.

健康ハザード

Pyrrole is harmful if swallowed, inhaled, or absorbed through the skin. Its vapor or mist is irritating to the eyes, mucous membranes and upper respiratory tract (Lenga, 1985; Sax, 1984). Although no cases of occupational disease due to pyrrole have been reported, it has a depressant action on the central nervous system and, in severe intoxication, it is injurious to the liver. Tests indicate that it has moderate cumulative toxicity (Parmegianni, 1983).

健康ハザード

The toxicity data on pyrrole are scant. Itis moderately toxic on test animals. Theroutes of exposure are inhalation of vapors,ingestion, and skin absorption. Vapors arean irritant to the eyes and respiratory tract.The lethal doses in rabbits by oral anddermal routes are within the range 150 and250 mg/kg, respectively.

火災危険

Combustible liquid; flash point (closed cup) 39°C (102°F); vapor forms explosive mixtures with air; LEL and UEL values are not available. Heating with strong oxidizers can be violent.

工業用途

Pyrrole is a five-member nitrogen heterocyclic ring that contains two carbon-carbon double bond configurations which gives the solvent a pronounced aromatic character. Pyrrole is an intermediate in the synthesis of a variety of commercial chemical derivatives. Pyrrole has only limited solubility in water but are miscible with many organic solvents.Pyrrole when freshly distilled is a colorless liquid, but the solvent can rapidly acquire a brown coloration due to air oxidation. Prolonged standing in the air will promote slow polymerization of the pyrrole to give a dark brown polymer. Pyrrole has a viscosity of 1.31 centipoise and a medium surface tension value of 37.1 dynes/cm.
pyrrole is used as a chemical intermediate in the preparation of electrically conducting polypyrrole by means of an electrochemical polymerization process. Pyrrole has few other industrial uses.

工業用途

Pyrrole is used to a limited extent as a solvent for polymeric esters, but its primary value lies in its function as a chemical intermediate. It is used in the synthesis of non-heterocyclic compounds (Kozikowski, 1984) and its derivatives have been used in the manufacture of dyes, herbicides, perfumes, and as cross-linking agents for curing resins (Thompson, 1972). Derivatives of pyrrole are utilized in pharmaceutical applications, particularly as anti-inflammation drugs and drugs with central nervous system activity, including antihypertensive effects (Sundberg, 1984); and as antimicrobial agents (Freeman, 1975), such as fungicides (Zirngibl, 1983) and bactericides (Bailey and Johnson, 1973; Bailey et al 1973; Sundberg, 1984). Polymers of pyrrole have been used in the preparation of photoconductive materials. The main utility of poly(pyrrole) has been for the modification of electrode surfaces, although numerous other applications can be envisioned (Heilmann and Rasmussen, 1984).

安全性プロファイル

Poison by ingestion, subcutaneous, and intraperitoneal routes. Flammable liquid when exposed to heat or flame; can react with oxilzing materials. To fight fire, use foam, CO2, dry chemical. Violent reaction with 2-nitrobenzaldehyde. When heated to decomposition it emits highly toxic fumes of NOx.

代謝

Reports concerning the metabolites formed following administration of pyrrole have been somewhat confusing. Saccardi (1919a, 1920) observed that administration of pyrrole orally and by injection resulted in the formation of melanin in the urine of rabbits, but not of dogs. Unchanged pyrrole was also found in the urine of rabbits after injection of pyrrole (Saccardi, 1919b). Shimizu (1921) isolated methylpyridine from the urine of rabbits and dogs given pyrrole and suggested that pyrrole could be converted to pyridine derivatives in vivo. The transformations in the body and the excretion products in the urine are, however, in question (Fairhall, 1969). Novello (1927) injected rabbits subcutaneously with 0.5 g doses of pyrrole hydrochloride and attempted to detect acetyl or methyl derivatives, but was unsucessful. Approximately 40-50% of the nitrogen of the injected pyrrole was excreted as urea. By the process of elimination, Novello (1927) concluded that the nitrogen not accounted for as urea nitrogen was excreted as unchanged pyrrole. It did not appear that the pyrrole was oxidized to a secondary or tertiary alcohol because there was no rise in ethereal sulfate or conjugated glucuronic acid excretion. Kusui (1935) injected frogs with pyrrole and noted that although the urine smelled of pyrrole, no free base could be isolated. Damani and Crooks (1982) have suggested that pyrrole may be a likely substrate for hydroxylation at C-2 and C-5, leading to ring opened products. They have not, however, studied the biotransformation of pyrrole, but based their hypothesis on studies of the metabolism of indole.
Pyrrole may affect the biotransformation of other compounds. Bernheim et al (1938) observed that pyrrole acted as a catalyst for the oxidation of amines and certain non-natural amino acids and catalyzed the formation of methemoglobin from hemoglobin. On the other hand, pretreatment of rats with 100 mg/kg pyrrole inhibited markedly the metabolism of dimethylnitrosamine in terms of both C02 excretion and decline in blood dimethylnitrosamine concentration (Phillips et al 1982).

純化方法

Dry pyrrole with NaOH, CaH2 or CaSO4. Fractionally distil it under reduced pressure from CaH2. Store it under nitrogen as it turns brown in air. Redistil it immediately before use. The picrate forms orange-red crystals with m 69o(dec). [Beilstein 20 H 4, 20 I 3, 20 II 3, 20 III/IV 61, 20/5 V 3.]

ピロール 上流と下流の製品情報

原材料

準備製品


ピロール 生産企業

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109-97-7(ピロール)キーワード:


  • 109-97-7
  • PYRROLE
  • 1-Aza-2,4-cyclopentadiene
  • Divinyleneimine
  • Monopyrrole
  • Parzate
  • Pyrrhol
  • Pyrrol
  • 4-methyl(di-pyrrol-2-yl-methtyl)pyridinium iodide
  • Pyrrole, 98+%
  • Azole, Divinylenimine, Imidole
  • Pyrrole, 99%, extra pure
  • Imidole 1H-Pyrrole
  • Pyrrole, extra pure, 99% 100GR
  • Pyrrole, extra pure, 99% 25GR
  • Pyrroline
  • 1H-PYRROLE
  • AZOLE
  • FEMA 3386
  • FEMA NUMBER 3386
  • IMIDOLE
  • DIVINYLENIMINE
  • PYRROLE PHARMA GRADE
  • PYRROLE 98+% FCC
  • Pyrrole,>97%
  • Pyrrole, extra pure, 99%
  • PYRROLE,REAGENT
  • ACETYL PYRROLE, 2-(SG)
  • PYRROLE FOR SYNTHESIS
  • Pyrrole reagent grade, 98%
  • Azole Divinylenimi Imidole 1H-Pyrrolene
  • ピロール
  • ジビニレンイミン
  • モノピロール
  • 1H-ピロール
  • アゾール
  • イミドール
  • ピロール標準品
  • ピロル
  • ピロール, 98+%
  • ピロール, 50 µg/mL in Toluene
  • ピロール (導電性ポリマー研究用試薬)
  • 導電性ポリマー研究用試薬
  • 機能性材料
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