1-ACETOXY-1,3-BUTADIENE

Product Name: 1-ACETOXY-1,3-BUTADIENE
CAS No.: 1515-76-0
Chemical Name: 1-ACETOXY-1,3-BUTADIENE
Synonyms: 1-Acetoxybutadiene;Butadienyl acetate;1,3-BUTADIENYL ACETATE;1-ACETOXY-1,3-BUTADIENE;1,3-butadien-1-ol,acetate;1,3-BUTADIEN-1-YL ACETATE;Acetic acid-1,3-butadienyl;(E)-1,3-Butadienyl acetate;Buta-1,3-dien-1-yl acetate;(1E)-1,3-Butadienyl acetate
CBNumber: CB6244909
Molecular Formula: C6H8O2
Formula Weight: 112.13
MOL File: 1515-76-0.mol

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1-ACETOXY-1,3-BUTADIENE Property

Boiling point:: 60-61 °C40 mm Hg(lit.)
Density: 0.96 g/mL at 20 °C(lit.)
vapor pressure: 40 mm Hg ( 60 °C)
refractive index: n20/D 1.47
Flash point:: 92 °F
storage temp.: 2-8°C
form: Liquid
BRN: 1743394
CAS DataBase Reference: 1515-76-0(CAS DataBase Reference)

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Safety

Hazard Codes: Xn
Risk Statements: 10-21/22-36/37/38
Safety Statements: 26-36/37
RIDADR: UN 1992 3/PG 3
WGK Germany: 3
RTECS: EJ1225000
HazardClass: 3
PackingGroup: III
HS Code: 2915390090
Toxicity: skn-rbt 100 mg/24H open AIHAAP 23,95,62

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

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

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 220868
Product name: 1-Acetoxy-1,3-butadiene
Purity: mixture of cis and trans
Packaging: 10g
Price: $308
Updated: 2024/03/01

Usbiological

Product number: 408671
Product name: 1-Acetoxy-1,3-butadiene
Packaging: 500mg
Price: $355
Updated: 2021/12/16

TRC

Product number: A164285
Product name: 1-Acetoxy-1,3-butadiene
Packaging: 1g
Price: $120
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CHM0006438
Product name: 1-ACETOXY-1,3-BUTADIENE
Purity: 95.00%
Packaging: 10G
Price: $1232.15
Updated: 2021/12/16

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1-ACETOXY-1,3-BUTADIENE Chemical Properties,Usage,Production

Chemical Properties

clear colorless to slightly yellow viscous liquid

Uses

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.

General Description

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:4?) has been reported.

Safety Profile

Poison by inhalation. Moderatelytoxic by other routes. A skin irritant. Mutation datareported. When heated to decomposition it emits acridsmoke.

Purification Methods

The commercial sample is stabilised with 0.1% of p-tert-butylcatechol. If the material contains crotonaldehyde (by IR, used in its synthesis), it should be dissolved in Et2O, shaken with 40% aqueous sodium bisulfite, then 5% aqueous Na2CO3, water, dried (Na2SO4) and distilled several times in a vacuum through a Widmer [Helv Chim Acta 7 59 1924] (p 11) or Vigreux column (p 11) [Wicterle & Hudlicky Collect Czech Chem Commun 12 564 1947, Hagemeyer & Hull Ind Eng Chem 41 2920 1949]. [Beilstein 2 III 295.]

1-ACETOXY-1,3-BUTADIENE Preparation Products And Raw materials

Raw materials

Preparation Products

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1-ACETOXY-1,3-BUTADIENE Suppliers

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1515-76-0, 1-ACETOXY-1,3-BUTADIENERelated Search:

Crotonaldehyde 1,3-Butadiene 19-Nor-17-alpha-pregna-3,5-dien-20-yne-3,17-diol, diacetate 1-ACETOXY-1,3-BUTADIENE TRANS,TRANS-1,4-DIACETOXY-1,3-BUTADIENE 4-tert-Butylcatechol 3-(METHOXYCARBONYL)-2H-CYCLOHEPTA[B]FURAN-2-ONE 5-ISOPROPYL-3-(METHOXYCARBONYL)-2H-CYCLOHEPTA[B]FURAN-2-ONE 3-ACETYL CYCLOHEPTA[B]FURAN-2-ONE 3-ACETOXY-2(1H)-PYRIDONE 97 2-ACETOXY-1,3-BUTADIENE 3,5-CHOLESTADIEN-3-OL 3-ACETATE 2,4,6-CYCLOHEPTATRIEN-1-ONE, 2-HYDROXY-3-IODO-, p-NITROBENZOATE 2H-CYCLOHEPTA(B)FURAN-2-ONE 3,5-ESTRADIEN-3,17-BETA-DIOL DIACETATE TESTOSTERONE ENOL DIACETATE AKOS 212-65 AKOS 210-09

(1E)-1,3-Butadienyl acetate

1,3-butadien-1-ol,acetate

1,3-Butadienylester kyseliny octove

1,3-butadienylesterkyselinyoctove

1-acetoxy-1,3-butadiene,mixtureofisomers

1-Acetoxybutadiene

Acetic acid, 1,3-butadienyl ester

aceticacid,1,3-butadienylester

Butadienyl acetate

1-ACETOXY-1,3-BUTADIENE

1-ACETOXY-1,3-BUTADIENE (CIS+TRANS)

1-ACETOXY-1,3-BUTADIENE, MIXTURE OF CIS AND TRANS

1-Acetoxy-1,3-butadiene, 97% mixture of isomers

crotonaldehyde enol acetate

1-ACETOXY-1,3-BUTADIENE, CIS + TRANS , STABILIZED WITH 0.1% 4-TERT-BUTYLCATECHOL

1-ACETOXY-1,3-BUTADIENE, CIS + TRANS, 90+%, STAB. WITH 0.1%

1-Acetoxy-1,3-butadiene, cis + trans, 90+%, stab. with 0.1% 4-tert-butylcatechol

1-Acetoxy-1,3-butadiene, cis + trans, 95%, stab. with 0.1% 4-tert-butylcatechol

Acetic acid-1,3-butadienyl

(1E)-1,3-Butadiene-1-ol acetate

(1E)-1-Acetoxy-1,3-butadiene

(E)-1,3-Butadienyl acetate

Acetic acid (1E)-1,3-butadienyl ester

1,3-BUTADIEN-1-YL ACETATE

1,3-BUTADIENYL ACETATE

(E)-buta-1,3-dien-1-yl acetate

1,3-Butadien-1-ol, 1-acetate

Buta-1,3-dien-1-yl acetate

1515-76-0

CH2CHCHCHOCOCH3

Building Blocks

C6 to C7

Carbonyl Compounds

Organic Building Blocks

Esters