220868

1-アセトキシ-1,3-ブタジエン, cis体およびtrans体混合物

mixture of cis and trans

• 別名: 1,3-ブタジエニル
• 化学式: CH₂=CHCH=CHOCOCH₃
• CAS番号: 1515-76-0
• 分子量: 112.13
• Beilstein: 1743394
• MDL番号: MFCD00008714
• UNSPSCコード: 12352100
• PubChem Substance ID: 24853196
• NACRES: NA.22

特性

• 蒸気圧: 40 mmHg ( 60 °C)
• 形状: liquid
• 含みます: 0.1% p-tert-butylcatechol as stabilizer
• 屈折率: n20/D 1.469 (lit.)
• bp: 60-61 °C/40 mmHg (lit.)
• 密度: 0.945 g/mL at 25 °C (lit.)
• 保管温度: 2-8°C
• SMILES記法: CC(=O)O\C=C\C=C
• InChI: 1S/C6H8O2/c1-3-4-5-8-6(2)7/h3-5H,1H2,2H3/b5-4+
• InChI Key: NMQQBXHZBNUXGJ-SNAWJCMRSA-N

詳細

詳細

1-Acetoxy-1,3-butadiene (1-ABD) can be generated by potassium or sodium acetate catalyzed reaction between crotonaldehyde and acetic anhydride. The product is a mixture of cis and trans forms, that has been confirmed by its physical properties and IR spectra. It is reported to be formed as a major product during the acetoxylation of 1,3-butadiene (BD) in gas-phase in the presence of Pd-KOAc (palladium-potassium acetate) catalyst. 1-ABD participates as 2Π or 4Π diene in cycloaddition reactions. Enantioselective Diels Alder reaction of 2-methoxy-5-methyl-1,4-benzoquinone with 1-ABD in the presence of molecular sieves (mesh size:4Å) has been reported.

アプリケーション

1-Acetoxy-1,3-butadiene was used as diene in the following reactions:

• Diels-Alder reaction with ortho-carbazolequinones to yield benzocarbazolequinone.
• Diels-Alder reaction with diethyl ketovinylphosphonate, with and without Lewis acid assistance.
• Diels-Alder reaction with methyl acrylate to yield racemic forms of 2-hydroxy-3-cyclohexenecarboxylic acid.

It was used for the reaction with dienophiles such as maleimides, a juglone, a butyne-1,4-dione and methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylate and during visible light photocatalysis. It was also used as reactant during intermolecular oxa-Pictet-Spengler cyclization.

安全性情報

• ピクトグラム: GHS02,GHS06
• シグナルワード: Danger
• 危険有害性情報: H226,H302,H311,H315,H319,H335
• 注意書き: P210 - P233 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• 危険有害性の分類: Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
• ターゲットの組織: Respiratory system
• 保管分類コード: 3 - Flammable liquids
• WGK: WGK 3
• 引火点(°F): 91.4 °F - closed cup
• 引火点(℃): 33 °C - closed cup
• 個人用保護具 (PPE): Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter