피롤
피롤 · 1H-PYRROLE · AZOLE · Pyrroline · Pyrrol · IMIDOLE · FEMA 3386 · Parzate
식별자 및 물리적 특성
| CAS No. | 109-97-7 |
|---|---|
| 분자식 | C4H5N |
| 평균 분자량 | 67.09 g/mol |
| 단동위원소 질량 | 67.04219916 g/mol |
| SMILES | c1cc[nH]c1 |
| InChIKey | KAESVJOAVNADME-UHFFFAOYSA-N |
| PubChem CID | 8027 |
| ChEMBL | CHEMBL16225 |
| ChEBI | CHEBI:19203 |
| EC No. | 203-724-7 |
| DTXSID | DTXSID5021910 |
| 현지명 | 피롤 |
화학 및 물리적 성질
| XLogP | 0.7 |
|---|---|
| 극성 표면적 | 15.8 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 0 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 5 |
| 형식 전하 | 0 |
| 복잡도 | 22.8 |
| 물질 분류 | Nitrogen Compounds -> Pyrroles |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| LogP(분배 계수) | log Kow = 0.75 |
| 냄새 | Agreeable empyreumatic odor resembling that of chloroform프로필렌 글리콜 중 0.10%. 달콤하고 따뜻하고 고소하고 천상의 |
| 맛 | Burning, pungent taste |
| 식품 첨가물 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 밀도 | 0.9698 @ 20 °C0.955-0.9750.9698 @ 20°C0.967 g/mL at 25 °C (lit.) |
| 향미제 | EU Flavoring substances |
| Viscosity | 4.1123X10-3 Pa.s @ 249.74K |
| Color/Form | Colorless liquid when freshYellowish or brown oil |
| 용해도 | Soluble in alcohol, ether and dilute acids. Also soluble in most organic chemicals.Water solubility: 4.5X10+4 mg/l @ 25 °C45 mg/mL at 25 °CSoluble in most fixed oilsSlightly soluble in waterSoluble (in ethanol)60g/L |
| 인화점 | 102 °F (39 °C) (CLOSED CUP)92 °F |
| 녹는점 | -23 °C (lit.) |
| 끓는 점 | 131 °C (lit.) |
| 증기 밀도 | 2.31 (vs air) |
| 증기압 | 8.7 hPa (20 °C) |
| FEMA | 3386 | PYRROLE |
| 굴절률 | n20/D 1.508(lit.) |
| 저장 조건 | Store at +2°C to +8°C. |
| pKa(산도 계수) | 15(at 25℃) |
| 물리적 상태 | 액체 |
| 색상 | 투명한 거의 무색~갈색 |
| pH | >6 (10g/l, H2O, 20℃) |
| 향취 유형 | 견과류 |
| 생물학적 소스 | synthetic |
| 폭발한계 | 3.10-14.8%(V) |
| 용해도 | 60g/L(20℃) |
| 비열 | Cp(liquid): 1.9 J/(g·K), at 25℃ |
| JECFA Number | 1314 |
| Merck | 14,8014 |
| BRN | 1159 |
| 헨리 상수 | 5.5×10-1 mol/(m3Pa) at 25℃, Hawthorne et al. (1985) |
| 유전율 | 7.5(17℃) |
| 안정성 | 안정적인. 강산, 강산화제와 호환되지 않습니다. 타기 쉬운. |
| 주요 응용 | 향료 및 향 |
| InChI | 1S/C4H5N/c1-2-4-5-3-1/h1-5H |
| InChIKey | KAESVJOAVNADME-UHFFFAOYSA-N |
| SMILES | c1cc[nH]c1 |
| LogP(분배 계수) | 0.85 |
| 표면장력 | 36.6mN/m at 20°C |
| NIST | Pyrrole(109-97-7) |
| EPA | 1H-Pyrrole (109-97-7) |
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).
안전 및 규제
| GHS 분류 | WarningH226 (10.7%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P317, P303+P361+P353, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1442 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H226: Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| 규제 정보 | Chemical: 1H-PyrroleCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 22-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/310751H-Pyrrole: Does not have an individual approval but may be used under an appropriate group standard |
| 화재 가능성 | Flammable liquid when exposed to heat or flame ... |
| 유해성 요약 | A CNS depressantMay cause liver injuryEffects of high doses administered by IP injection in dogs include convulsions and liver injury[HSDB] Safe when used as a flavoring agent in food[JECFA] Causes convulsions and muscle contractions in oral lethal-dose studies of rabbits[RTECS] |
| NFPA Hazard Classification | 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Hazard Classes and Categories | Flam. Liq. 3 (10.7%)Flammable liquids - Category 3 |
| Critical Temperature and Pressure | Critical temperature: 366.75 °CCritical pressure: 6.21X10+6 Pa |
용도
일반 설명
Pyrrole is one of the flavor compounds that is formed in thermally processed foods due to the Maillard reaction.
제조 및 합성 방법
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.
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).