이미다졸

이미다졸
이미다졸 구조식 이미지
카스 번호:
288-32-4
한글명:
이미다졸
동의어(한글):
이미다졸;1,3-디아졸(1,3-DIAZOLE)이미나졸(IMINAZOLE)미아졸(MIAZOLE)피프로(B)-모나졸(PYRRO(B)-MONAZOLE)1,3-디아자-2,4-시클로펜타디엔(1,3-DIAZA-2,4-CYCLOPENTADIENE)글리옥살린(GLYOXALIN)이미다졸(IMIDAZOL)이무텍스(IMUTEX)1H-이미다졸;글리옥살린;1,3-디아졸;이미나졸;미아졸;글리옥살린;이무텍스;피프로(B)-모나졸;1,3-다이아자-2,4-싸이클로펜타디엔;1,3-다이아졸;1H-이미다졸(9CI);마이아졸;메탄이미다마이드, N,N'-1,2-에텐다일-;이미다졸(8CI)
상품명:
Imidazole
동의어(영문):
1H-IMIDAZOLE;Imidazol;IMZ;IMD;GLYOXALINE;LMIDAZOLE;IMINAZOLE;GLYOXALIN;Imidazoie;1H-Imidazol
CBNumber:
CB6460617
분자식:
C3H4N2
포뮬러 무게:
68.08
MOL 파일:
288-32-4.mol
MSDS 파일:
SDS

이미다졸 속성

녹는점
88-91 °C(lit.)
끓는 점
256 °C(lit.)
밀도
1.01 g/mL at 20 °C
증기압
<1 mm Hg ( 20 °C)
굴절률
1.4801
인화점
293 °F
저장 조건
Store below +30°C.
용해도
H2O: 0.1 M at 20 °C, 투명, 무색
물리적 상태
수정 같은
산도 계수 (pKa)
6.953(at 25℃)
Specific Gravity
1.03
색상
하얀색
냄새
아민 같은
pH 범위
9.5 - 11
수소이온지수(pH)
9.5-11.0 (25℃, 50mg/mL in H2O)
수용성
633g/L(20℃)
감도
Hygroscopic
최대 파장(λmax)
λ: 260 nm Amax: 0.10
λ: 280 nm Amax: 0.10
Merck
14,4912
BRN
103853
Dielectric constant
23.0(Ambient)
안정성
안정적인. 산, 강한 산화제와 호환되지 않습니다. 습기로부터 보호하십시오.
InChIKey
RAXXELZNTBOGNW-UHFFFAOYSA-N
LogP
-0.02 at 25℃
CAS 데이터베이스
288-32-4(CAS DataBase Reference)
NIST
1H-Imidazole(288-32-4)
EPA
Imidazole (288-32-4)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 C,Xi,T
위험 카페고리 넘버 36/38-63-34-22-20/21/22-61
안전지침서 26-36/37/39-45-22-36-27-53
유엔번호(UN No.) UN 2923 8/PG 3
WGK 독일 1
RTECS 번호 NI3325000
자연 발화 온도 480 °C
TSCA Yes
위험 등급 8
포장분류 III
HS 번호 29332990
유해 물질 데이터 288-32-4(Hazardous Substances Data)
독성 LD50 in mice (mg/kg): 610 i.p.; 1880 orally (Nishie)
기존화학 물질 KE-20937
그림문자(GHS): GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 GHS hazard pictograms P264, P270, P301+P312, P330, P501
H314 피부에 심한 화상과 눈에 손상을 일으킴 피부부식성 또는 자극성물질 구분 1A, B, C 위험 GHS hazard pictograms P260,P264, P280, P301+P330+ P331,P303+P361+P353, P363, P304+P340,P310, P321, P305+ P351+P338, P405,P501
예방조치문구:
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P301+P312 삼켜서 불편함을 느끼면 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.
NFPA 704
1
3 0

이미다졸 C화학적 특성, 용도, 생산

물성

글리옥살에 폼알데하이드와 암모니아를 반응시켜 얻는, 무색 고체. 강한 염기성을 띠며, 물, 알코올에 잘 녹는다. 화학식은 C3H4N2. [비슷한 말] 글리옥살린.

개요

Imidazole group denotes a heterocyclic organic compound whose molecule contains a five-membered hetero-aromatic ring of two non-adjacent nitrogen atoms, that a carbon atom is placed between two nitrogen atoms. Imidazole is the universally used trivial name for 1,3-azole. Earlier given names were glyoxaline and iminazole. The importance of this aromatic ring system is reflected by its presence in naturally occurring histidine, histamine and the purines, and in several classes of pharmaceuticals. Imidazole can act as a base and as a weak acid. It exists in two tautomeric forms with the hydrogen atom taking position between the two nitrogen atoms.

화학적 성질

Imidazole is a moderately strong base (pKb= 7.0), and a weak acid (pKa= 14.9). Imidazoles substituted with electron-withdrawing groups are stronger acids than imidazole itself; e.g., 4(5)-nitroimidazole has a pKa of 9.3. Imidazole is stable at 400°C, possesses considerable aromatic character, and undergoes the usual electrophilic aromatic substitution reactions. Nitration and sulfonation require, however, far more drastic conditions than the corresponding reactions with benzene. Other substitution reactions of imidazole include halogenation, hydroxymethylation, coupling with aromatic diazonium salts, and carboxylation.

역사

Imidazole[288-32-4] was first synthesized in 1858 by Debus from ammonia and glyoxal; it was originally named glyoxalin. The name imidazole was introduced by Hantzsch. Industrial production of imidazole began in the 1950s; a wide range of derivatives is now available in industrial quantities.

주요 응용

Imidazole is a versatile heterocycle used in the preparation of various biologically active compounds such as the amino acid histidine and is present in many antifungal medication. It is also used ext ensively as a corrosion inhibitor on transition metals such as copper.It is used in organic synthesis and as an antiirradiationagent.
Imidazole has been used:
in the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein.
in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography.
as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cell.

제조 방법

Imidazole is formed by reacting glyoxal with formaldehyde in the presence of ammonium acetate in acetic acid. The driving energy is microwave radiation. More generally, this reaction is used to produce substituted imidazoles.
synthesis of Imidazole
Although there had been discoveries of various derivatives of imidazole in 1840, it was first reported in 1858. The synthesis process of imidazole follows the reaction between formaldehyde in ammonia and glyoxal. This process gives low yield of imidazole but it is still used to form imidazole with C-substitution (Wolkenberg et al., 2004).

정의

ChEBI: Imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. It is an important pharmacophore in drug discovery. Imidazole is used as a Karl Fischer reagent in analytical chemistry and a reagent in synthetic organic chemistry.

일반 설명

Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.

건강위험

It is less toxic relative to pyrrole and otherfive-membered heterocyclic compounds ofnitrogen. Intraperitoneal administration ofimidazole caused somnolence, muscle contractions,and convulsions in mice. Theoral LD50 value in mice is in the range900 mg/kg.

화재위험

Noncombustible solid.

Mechanism of action

N-substitution of imidazoles has created a family of drugs, called triazoles, that have the same mechanism of action as imidazoles, a similar or broader spectrum of activity, and less effect on human sterol synthesis. Both imidazoles and triazoles inhibit C-14α demethylation of lanosterol in fungi by binding to one of the cytochrome P-450 enzymes, which leads to the accumulation of C-14α methylsterols and reduced concentrations of ergosterol, a sterol essential for a normal fungal cytoplasmic membrane. Inhibition of cytochrome P-450 also decreases the synthesis of testosterone and glucocorticoids in mammals, an effect seen clinically with ketoconazole but not with later azoles[1].

Purification Methods

Crystallise imidazole from *benzene, CCl4, CH2Cl2, EtOH, pet ether, acetone/pet ether and distilled de-ionized water. Dry it at 40o under vacuum over P2O5. Distil it at low pressure. It is also purified by sublimation or by zone melting. [Snyder et al. Org Synth Coll Vol III 471 1955, Bredereck et al. Chem Ber 97 827 1964, Caswell & Spiro J Am Chem Soc 108 6470 1986.] 15N-imidazole crystallises from *benzene [Scholes et al. J Am Chem Soc 108 1660 1986]. [Beilstein 23 II 34, 23 III/IV 564, 23/4 V 191.]

이미다졸 준비 용품 및 원자재

원자재

준비 용품


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