B57001

2-Bromobenzaldehyde

98%

• Sinonimo/i: 2-Formylbromobenzene
• Formula condensata: BrC₆H₄CHO
• Numero CAS: 6630-33-7
• Peso molecolare: 185.02
• Beilstein: 636132
• Numero CE: 229-622-2
• Numero MDL: MFCD00003300
• Codice UNSPSC: 12352100
• ID PubChem: 24891854
• NACRES: NA.22

Proprietà

• Livello qualitativo: 100
• Saggio: 98%
• Stato: liquid
• Indice di rifrazione: n20/D 1.595 (lit.)
• P. ebollizione: 230 °C (lit.)
• Punto di fusione: 16-19 °C (lit.)
• Densità: 1.585 g/mL at 25 °C (lit.)
• Stringa SMILE: Brc1ccccc1C=O
• InChI: 1S/C7H5BrO/c8-7-4-2-1-3-6(7)5-9/h1-5H; NDOPHXWIAZIXPR-UHFFFAOYSA-N

Descrizione

Descrizione generale

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]

Applicazioni

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]

Informazioni sulla sicurezza

• Pittogrammi: GHS07
• Avvertenze: Warning
• Indicazioni di pericolo: H315,H319,H335
• Consigli di prudenza: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Classi di pericolo: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Organi bersaglio: Respiratory system
• Codice della classe di stoccaggio: 10 - Combustible liquids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): 203.0 °F - closed cup
• Punto d’infiammabilità (°C): 95 °C - closed cup
• Dispositivi di protezione individuale: Eyeshields, Gloves, type ABEK (EN14387) respirator filter