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B57001

Sigma-Aldrich

2-Bromobenzaldehyde

98%

Synonyme(s) :

2-Formylbromobenzene

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About This Item

Formule linéaire :
BrC6H4CHO
Numéro CAS:
Poids moléculaire :
185.02
Beilstein:
636132
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22
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Niveau de qualité

Essai

98%

Forme

liquid

Indice de réfraction

n20/D 1.595 (lit.)

pb

230 °C (lit.)

Pf

16-19 °C (lit.)

Densité

1.585 g/mL at 25 °C (lit.)

Chaîne SMILES 

Brc1ccccc1C=O

InChI

1S/C7H5BrO/c8-7-4-2-1-3-6(7)5-9/h1-5H

Clé InChI

NDOPHXWIAZIXPR-UHFFFAOYSA-N

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Description générale

2-Bromobenzaldehyde is a versatile building block used in Suzuki-Miyaura and Buchwald-Hartwig reactions, cross-coupling reactions to form carbon-carbon or carbon-heteroatom bonds[1]

Application

Synthetic applications of 2-bromobenzaldehyde include:
  • Synthesis of aza-fused polycyclic quinolines through copper-catalyzed cascade reaction.[2]
  • Preparation of 1-substituted indazoles by CuI-catalyzed coupling with N-aryl hydrazides.[3]
  • It is a key starting material in the total synthesis of an anticancer agent, (-)-taxol.[4]
  • Palladium/copper-catalyzed coupling and cyclization of terminal acetylenes derived from 2-bromobenzaldehyde and unsaturated imines can be used in the synthesis of wide range of isoquinolines, including decumbenine B.[5]
  • Fluoren-9-ones can be synthesized by annulation of arynes, generated in situ from 2-(trimethylsilyl)aryl triflates, with 2-bromobenzaldehyde in the presence of palladium(0) catalyst.[6]
  • It can also be used to build a variety of steroid frameworks, in which ring A is derived from 2-bromobenzaldehyde.[7]

Pictogrammes

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Mention d'avertissement

Warning

Mentions de danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

203.0 °F - closed cup

Point d'éclair (°C)

95 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Les clients ont également consulté

A gold-catalyzed domino process to the steroid framework.
Hildebrandt D and Dyker G
The Journal of Organic Chemistry, 71(18), 6728-6733 (2006)
Assembly of N, N-Disubstituted Hydrazines and 1-Aryl-1 H-indazoles via Copper-Catalyzed Coupling Reactions.
Xiong X, et al.
Organic Letters, 14(10), 2552-2555 (2012)
Synthesis of isoquinolines and pyridines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes and unsaturated imines: the total synthesis of decumbenine B.
Roesch K R and Larock R C
The Journal of Organic Chemistry, 67(1), 86-94 (2002)
Enantioselective total synthesis of (?)-taxol.
Kusama H, et al.
Journal of the American Chemical Society, 122(16), 3811-3820 (2000)
Palladium-catalyzed one-pot Suzuki-Miyaura cross coupling followed by oxidative lactonization: a novel and efficient route for the one-pot synthesis of benzo [c] chromene-6-ones
R Singha, et al.
Tetrahedron Letters, 54, 657-660 (2013)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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