1-Acetoxy-1,3-butadiene

CAS 1515-76-0CH2=CHCH=CHOCOCH3Chemical Synthesis

1-Acetoxy-1,3-butadiene (CAS: 1515-76-0) is a chemical compound with the molecular formula CH 2 =CHCH=CHOCOCH 3 and a molecular weight of 112.13 g/mol. This organic building block serves primarily as a diene in Diels-Alder reactions and as a reactant in various organic syntheses. Its applications span the creation of complex cyclic structures and functionalised molecules, making it a valuable reagent for chemical research and development.

IUPAC: 1,3-Butadienyl acetate
Synonyms: CH2=CHCH=CHOCOCH31,3-Butadienyl acetate

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1-Acetoxy-1,3-butadiene (CH2=CHCH=CHOCOCH3) — chemical structure, CAS 1515-76-0; Chemistry, fine chemical supplied by Tech Serve Solutions

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01 /Applications

Diels-Alder Reactions

1-Acetoxy-1,3-butadiene functions as a diene in Diels-Alder cycloaddition reactions. It readily reacts with various dienophiles, including maleimides, butyne-1,4-diones, and methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylates, to form cyclic adducts.

Synthesis of Benzocarbazolequinones

This compound has been employed in the synthesis of benzocarbazolequinones through its reaction with ortho-carbazolequinones, showcasing its utility in constructing polycyclic aromatic systems.

Formation of Carboxylic Acid Derivatives

Reaction with methyl acrylate leads to the formation of racemic forms of 2-hydroxy-3-cyclohexenecarboxylic acid, highlighting its role in creating functionalised cyclohexene scaffolds.

Intermolecular Oxa-Pictet-Spengler Cyclization

1-Acetoxy-1,3-butadiene serves as a reactant in intermolecular oxa-Pictet-Spengler cyclization reactions, contributing to the synthesis of complex heterocyclic compounds.

02 /Properties

Molecular weight	112.13
Linear formula	CH2=CHCH=CHOCOCH3
Boiling point	60-61 °C/40 mmHg(lit.)
Density	0.945 g/mL at 25 °C(lit.)
Refractive index	n20/D 1.469(lit.)
Vapour pressure	40 mmHg (60 °C)
Storage temperature	2-8°C
Contains / stabiliser	0.1% p-tert-butylcatechol as stabilizer
Application	1-Acetoxy-1,3-butadiene was used as Diels-Alder diene:• for reaction with ortho-carbazolequinones to yield benzocarbazolequinone1• for reaction with diethyl ketovinylphosphonate with and without Lewis acid assistance2• for reaction with methyl acrylate to yield racemic forms of 2-hydroxy-3-cyclohexenecarboxylic acid3• for reaction with dienophiles such as maleimides4, a juglone5, a butyne-1,4-dione6 and methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylate• during visible light photocatalysis7It was also used as reactant during intermolecular oxa-Pictet-Spengler cyclization8.

03 /Safety & handling

GHS hazard pictogram: Flammable (GHS02) — Flammable

GHS hazard pictogram: Toxic (GHS06) — Toxic

Danger

Hazard statements

H226Flammable liquid and vapour
H302Harmful if swallowed
H311Toxic in contact with skin
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust, fume, gas or vapours
P280Wear protective gloves, clothing and eye/face protection
P305IF IN EYES
P312Call a POISON CENTER if you feel unwell

Protective equipment	Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Flash point	33 °C / 91.4 °F
Transport (UN / ADR)	UN 1992 3/PG 3
Water hazard class (WGK, DE)	3
Hazard codes (EU)	Xn
Risk statements (R)	10-21/22-36/37/38
Safety statements (S)	26-36/37

Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.

04 /Identifiers & registry

CAS number

1515-76-0

MDL number

MFCD00008714

PubChem substance

24853196

Beilstein registry

1743394

05 /Quality & supply

Documentation

Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.

Supply & logistics

Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.

06 /Frequently asked questions

What is 1-Acetoxy-1,3-butadiene used for?

1-Acetoxy-1,3-butadiene is primarily used as a diene in Diels-Alder reactions and as a reactant in various organic syntheses, including the formation of benzocarbazolequinones and in oxa-Pictet-Spengler cyclizations.

What is the CAS number and formula for 1-Acetoxy-1,3-butadiene?

The CAS number is 1515-76-0, and the linear formula is CH 2 =CHCH=CHOCOCH 3 .

What grade and purity does Tech Serve Solutions supply?

Tech Serve Solutions supplies 1-Acetoxy-1,3-butadiene with 0.1% p-tert-butylcatechol as a stabilizer. The specific assay or purity is not detailed in the provided data. TSS does not represent this product as USP, BP, or EP grade.

How should 1-Acetoxy-1,3-butadiene be handled safely?

1-Acetoxy-1,3-butadiene is a flammable liquid and vapour (H226), harmful if swallowed (H302), toxic in contact with skin (H311), causes skin irritation (H315), causes serious eye irritation (H319), and may cause respiratory irritation (H335). Handle with appropriate personal protective equipment, including eyeshields, faceshields, gloves, and a suitable respirator. Store at 2-8°C.