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Merck

510300

Sigma-Aldrich

2-溴-1,4-萘醌

98%

别名:

2-Bromo-1,4-dihydronaphthalene-1,4-dione, 2-Bromo-1,4-naphthalenedione, 2-Bromo-p-naphthoquinone, 3-Bromo-1,4-naphthoquinone, 3-Bromonaphthoquinone

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About This Item

经验公式(希尔记法):
C10H5BrO2
CAS号:
分子量:
237.05
MDL號碼:
分類程式碼代碼:
12352100
PubChem物質ID:
NACRES:
NA.22

品質等級

化驗

98%

mp

131-133 °C (lit.)

SMILES 字串

BrC1=CC(=O)c2ccccc2C1=O

InChI

1S/C10H5BrO2/c11-8-5-9(12)6-3-1-2-4-7(6)10(8)13/h1-5H

InChI 密鑰

KJOHPBJYGGFYBJ-UHFFFAOYSA-N

一般說明

2-溴-1,4-萘醌(BrQ)是一种 1,4-萘醌衍生物,可以通过使用 N-溴代琥珀酰亚胺将 1-萘酚溴化来制备。已评估了其作为抗粉纹夜蛾(粉纹夜蛾)的拒食剂的功效。2 已经研究了在光化学条件下 BrQ 与氧杂蒽的反应。一份报告表明,用 BrQ 取代 2-甲基-1,4-萘醌可增强其产生过氧化氢的能力,该作用可用于癌症治疗。

應用

2-溴-1,4-萘醌可用于制备:
  • 苯并[f]吲哚醌
  • 2-叠氮基-1,4-萘醌
  • 2-烯丙基-3-溴-1,4-萘醌
  • 2-(3-吲哚基)-1,4-萘醌

象形圖

Exclamation mark

訊號詞

Warning

危險聲明

危險分類

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

標靶器官

Respiratory system

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves


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The Photochemical Reaction of 1,4-Naphthoquinone Derivatives with Hydrogen Donors.
Maruyama K and Arakawa S.
Bulletin of the Chemical Society of Japan, 47(8), 1960-1966 (1974)
Padmakar A Suryavanshi et al.
Organic & biomolecular chemistry, 8(15), 3426-3436 (2010-06-10)
The CAN-catalyzed three-component between reaction between primary amines, beta-dicarbonyl compounds and naphthoquinones or 2-bromonaphthoquinones afforded, respectively, 5-hydroxybenzo[g]indoles and benzo[f]indole-4,9-diones, the former of which were transformed into tetracyclic azepino[1,2-a]benzo[g]indole systems through a gamma-alkylation/ring-closing metathesis sequence.
Tiago T Guimarães et al.
European journal of medicinal chemistry, 63, 523-530 (2013-03-29)
Continuing our screening program for novel anti-parasite compounds, we synthesized seven 1,4-naphthoquinones coupled to 1,2,3-triazoles, five nor-β-lapachone-based 1,2,3-triazoles and ten α-lapachone-based 1,2,3-triazoles. These and other naphthoquinonoid compounds were evaluated for their activity against promastigote forms of antimony-sensitive and -resistant strains
Stereoselective synthesis of deoxy analogues of the 3C-protease inhibitor thysanone.
Brimble MA and Elliott RJR
Tetrahedron, 58(1), 183-189 (2002)
F S Graciani et al.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas, 45(8), 701-710 (2012-05-16)
Apatone™, a combination of menadione (2-methyl-1,4-naphthoquinone, VK3) and ascorbic acid (vitamin C, VC) is a new strategy for cancer treatment. Part of its effect on tumor cells is related to the cellular pro-oxidative imbalance provoked by the generation of hydrogen

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