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120-72-9 - Indole, 99% - A14427 - Alfa Aesar

A14427 Indole, 99%

CAS 번호
120-72-9
동의어

사이즈 가격 ($) 수량 재고 여부
50g 31.00
250g 116.00
1000g 388.00
장바구니에 추가 대량 견적에 추가 항목 보기

Indole, 99%

MDL
MFCD00005607
EINECS
204-420-7

화학적 특성

화학식
C8H7N
화학 식량
117.15
융점
50-54°
비등점
253-254°
인화점
121°(249°F)
밀도
1.220
감도
Light Sensitive
용해도
Soluble in methanol and water.

용도

Indole is used in the preparation of gramine, which is obtained by Mannich reaction dimethylamine and formaldehyde. It is used as a starting material for the preparation of oxindole and indole-3-carboxaldehyde. In Diels-Alder reaction, it acts as dienophile and reacts with 2-aminofuran to get strychnine. It is the active component of jasmine oil, neroli oil and orange-blossom oil used in the perfume industry. Further, it is involved in the preparation of synthetic jasmine oil.

참고

Light and air sensitive. Store in a cool place. Incompatible with strong oxidizing agents, iron and iron salts. Keep the container tightly closed in a dry and well-ventilated place.

참조 문헌

Lithiation of N-protected indoles usually occurs at the 2-position, e.g. benzenesulfonation of the 1-lithio derivative, 2-lithiation with LDA and treatment with pyridine-3,4-dicarboxylic anhydride. This sequence has been reported in a synthetic route to ellipticene and olivacine: J. Org. Chem., 57, 5891 (1992).

Regioselective synthesis of 3-substituted indoles has been described using a sequence of N-silylation, 3-bromination of the 1-TBDMS detivative with NBS, 3-lithiation, treatment with an electrophile to introduce the 3-substituent, and desilylation with TBAF. Good overall yields are obtained for a range of electrophiles: J. Org. Chem., 59, 10 (1994); Org. Synth. Coll., 9, 417 (1998).

Treatment with EtMgI followed by ZnCl2 leads to an N-zinc derivative. This undergoes acylation at the 3-position: Tetrahedron, 46, 6061 (1990).

Halogenation in the 2-position has been effected via the Li 1-carbamate and subsequent 2-lithiation: J. Org. Chem., 57, 2495 (1992):

Treatment of the carbamate with Tri-n-butyl­tin chloride, A10746, followed by Stille coupling enables synthesis of 2-aryl- and 2-vinylindoles: J. Org. Chem., 60, 6218 (1995).

Johnston, A. J.; Zhang, Y. R.; Busch, S.; Pardo, L. C.; Imberti, S.; McLain, S. E. Amphipathic Solvation of Indole: Implications for the Role of Tryptophan in Membrane Proteins. J. Phys. Chem. B 2015, 119 (19), 5979-5987.

Yang, P.; Pang, M.; Shen, W.; Li, M.; He, R. Vibronic analysis of the 1Lb ? S0 transitions of indole and 3-methylindole: The influence of anharmonic, Duschinsky, and Herzberg-Teller contributions. J. Mol. Spectrosc. 2015, 313, 40-48.

GHS 해저드 및 주의 설명서

해저드 설명서 (EU): H302-H311-H318

Harmful if swallowed. Toxic in contact with skin. Causes serious eye damage.

주의 설명서: P280-P305+P351+P338-P310a-P301+P312a-P405-P501a

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

기타 참조

Merck
14,4963
바일슈타인
107693
위험 등급
6.1
포장 그룹
III
통합 관세 코드
2933.99
TSCA(독성물질규제법)"
Yes
RTECS(화학물질 독성 등록)
NL2450000

권장

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