Accéder au contenu
Merck
Toutes les photos(1)

Key Documents

View All Documentation

220868

Sigma-Aldrich

1-Acetoxy-1,3-butadiene

mixture of cis and trans

Synonyme(s) :

1,3-Butadienyl acetate

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(1)

About This Item

Formule linéaire :
CH2=CHCH=CHOCOCH3
Numéro CAS:
1515-76-0
Poids moléculaire :
112.13
Numéro Beilstein :
1743394
Numéro MDL:
MFCD00008714
Code UNSPSC :
12352100
ID de substance PubChem :
24853196
Nomenclature NACRES :
NA.22

Pression de vapeur

40 mmHg ( 60 °C)

Niveau de qualité

100

Forme

liquid

Contient

0.1% p-tert-butylcatechol as stabilizer

Indice de réfraction

n20/D 1.469 (lit.)

Point d'ébullition

60-61 °C/40 mmHg (lit.)

Densité

0.945 g/mL at 25 °C (lit.)

Groupe fonctionnel

ester

Température de stockage

2-8°C

Chaîne SMILES 

CC(=O)O\C=C\C=C

InChI

1S/C6H8O2/c1-3-4-5-8-6(2)7/h3-5H,1H2,2H3/b5-4+

Clé InChI

NMQQBXHZBNUXGJ-SNAWJCMRSA-N

Description générale

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.

Application

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.

Pictogrammes

FlameSkull and crossbones
GHS02,GHS06

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

91.4 °F - closed cup

Point d'éclair (°C)

33 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Faites votre choix parmi les versions les plus récentes :

Certificats d'analyse (COA)

Lot/Batch Number
MKCM6228
MKCC6633
MKBX1238V
MKBP3083V
54297LJV

Vous ne trouvez pas la bonne version ?

Si vous avez besoin d'une version particulière, vous pouvez rechercher un certificat spécifique par le numéro de lot.

Rechercher un(e) COA

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Synthesis and absolute configuration of the isomers of homoisocitric acid (1-hydroxy-1,2,4-butanetricarboxylic acid) and the stereochemistry of lysine biosynthesis.
K Chilina et al.
Biochemistry, 8(7), 2846-2855 (1969-07-01)
Journal of the Chemical Society. Perkin Transactions 1, 1925-1925 (1993)
Muriel Compain-Batissou et al.
Chemical & pharmaceutical bulletin, 52(9), 1114-1116 (2004-09-02)
Oxidation of 2- and 3-hydroxycarbazoles with Frémy's salt gave the corresponding ortho-carbazolequinones. These molecules react as carbodienophiles in Diels-Alder reaction with 1-acetoxy-1,3-butadiene and 1,3-cyclopentadiene to provide the novel benzocarbazolequinone structures 15, 16, 18 and 19.
Gas phase acetoxylation of 1, 3-butadiene over palladium catalysts Part 1: the catalytic activity and structure of Pd-Sb-KOAc catalysts.
Shinohara H.
Applied Catalysis, 10(1), 27-42 (1984)
Intra- and Intermolecular Oxa-Pictet-Spengler Cyclization Strategy for the Enantioselective Synthesis of Deoxy Analogues of (+)-Nanomycin A Methyl Ester, (+)-Eleutherin, (+)-Allo-Eleutherin, and (+)-Thysanone
R. T. Sawant, et al.
European Journal of Organic Chemistry, 23, 4442-4449 (2010)
Afficher tous les articles scientifiques apparentés

Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique