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피롤

피롤
피롤 구조식 이미지
카스 번호:
109-97-7
한글명:
피롤
동의어(한글):
피롤
상품명:
Pyrrole
동의어(영문):
AZOLE;Pyrrol;PYRROLE;Pyrrhol;Parzate;IMIDOLE;Pyrroline;FEMA 3386;1H-PYRROLE;Monopyrrole
CBNumber:
CB3852794
분자식:
C4H5N
포뮬러 무게:
67.09
MOL 파일:
109-97-7.mol

피롤 속성

녹는점
-23 °C
끓는 점
131 °C(lit.)
밀도
0.967 g/mL at 25 °C(lit.)
증기 밀도
2.31 (vs air)
증기압
8.7 hPa (20 °C)
FEMA
3386 | PYRROLE
굴절률
n20/D 1.508(lit.)
인화점
92 °F
저장 조건
0-6°C
용해도
60g/l
산도 계수 (pKa)
15(at 25℃)
물리적 상태
Liquid
색상
Clear almost colorless to brownish
수소이온지수(pH)
>6 (10g/l, H2O, 20℃)
폭발한계
3.10-14.8%(V)
수용성
60 g/L (20 ºC)
감도
Air & Light Sensitive
Merck
14,8014
JECFA Number
1314
BRN
1159
안정성
Stable. Incompatible with strong acids, strong oxidizing agents. Combustible.
InChIKey
KAESVJOAVNADME-UHFFFAOYSA-N
CAS 데이터베이스
109-97-7(CAS DataBase Reference)
NIST
Pyrrole(109-97-7)
EPA
1H-Pyrrole(109-97-7)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T
위험 카페고리 넘버 10-20-25-41
안전지침서 26-37/39-45-39-24-16
유엔번호(UN No.) UN 1992 3/PG 3
WGK 독일 2
RTECS 번호 UX9275000
F 고인화성물질 8-10-23
자연 발화 온도 550 °C
TSCA Yes
위험 등급 3
포장분류 III
HS 번호 29339900
유해 물질 데이터 109-97-7(Hazardous Substances Data)
독성 LD50 orally in Rabbit: 137 mg/kg
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H226 인화성 액체 및 증기 인화성 액체 구분 3 경고
H301 삼키면 유독함 급성 독성 물질 - 경구 구분 3 위험 P264, P270, P301+P310, P321, P330,P405, P501
H311 피부와 접촉하면 유독함 급성 독성 물질 - 경피 구분 3 위험 P280, P302+P352, P312, P322, P361,P363, P405, P501
H318 눈에 심한 손상을 일으킴 심한 눈 손상 또는 자극성 물질 구분 1 위험 P280, P305+P351+P338, P310
H331 흡입하면 유독함 급성 독성 물질 흡입 구분 3 위험 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H332 흡입하면 유해함 급성 독성 물질 흡입 구분 4 경고 P261, P271, P304+P340, P312
예방조치문구:
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P233 용기를 단단히 밀폐하시오. 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 보관하시오.
P240 용기와 수용설비를 접지 및 접합시키시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P271 옥외 또는 환기가 잘 되는 곳에서만 취급하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P303+P361+P353 피부(또는 머리카락)에 묻으면 오염된 모든 의복은 벗거나 제거하시오 피부를 물로 씻으시오/샤워하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P370+P378 화재 시 불을 끄기 위해 (Section 5. 폭발, 화재시 대처방법의 적절한 소화제)을(를) 사용하시오.
P405 밀봉하여 저장하시오.
P403+P235 환기가 잘 되는 곳에 보관하고 저온으로 유지하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

피롤 C화학적 특성, 용도, 생산

화학적 성질

colourless to brown liquid with chloroform odour

화학적 성질

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).

화학적 성질

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

출처

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).

용도

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

용도

Manufacture of pharmaceuticals.

정의

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

생산 방법

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).

정의

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

제조 방법

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

위험도

Moderate fire risk. Toxic by ingestion and inhalation.

건강위험

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.

건강위험

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).

화재위험

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.

공업 용도

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.

공업 용도

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).

Safety Profile

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.

신진 대사

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).

Purification Methods

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.]

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