(1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate

Basic Information

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CAS Number

52946-22-2

Molecular Formula

C13H14O4

Molecular Weight

234.25 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

SMILES

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CC(=O)OC1=CC=C(C=C1)C(C=C)OC(=O)C

InChI

InChI=1S/C13H14O4/c1-4-13(17-10(3)15)11-5-7-12(8-6-11)16-9(2)14/h4-8,13H,1H2,2-3H3/t13-/m0/s1

InChIKey

JAMQIUWGGBSIKZ-ZDUSSCGKSA-N

LogP

2.4021

Topological Polar Surface Area

52.6 Å²

Hydrogen Bond Donor/Acceptor

0 / 4

Complexity

290

Synonyms & References

English

Benzenemethanol, 4-(acetyloxy)-alpha-ethenyl-, acetate, (S)-
(S)-1'-Acetoxychavicol Acetate
1'S-1'-Acetoxychavicol acetate
CHEMBL323727
CHEBI:469
UNII-SQV3080A20
(S)-4-(1-Acetoxyallyl)phenyl acetate
1'-Acetoxychavicol acetate
GALANGAL ACETATE, (S)-
DTXSID80967420
[4-[(1S)-1-acetoxyallyl]phenyl] acetate
Benzenemethanol, 4-(acetyloxy)-.alpha.-ethenyl-, acetate, (S)-
CS-0063645
GALANGAL ACETATE, (-)-
Z2737403435
Benzenemethanol, 4-(acetyloxy)-.alpha.-ethenyl-, 1-acetate, (.alpha.S)-
GTPL6298
1'-ACETOXYCHAVICOL ACETATE, (-)-
HY-114644
EN300-27114805
(alphaS)-4-(Acetyloxy)-alpha-ethenylbenzenemethanol
Benzenemethanol, 4-(acetyloxy)-.alpha.-ethenyl-, acetate, (.alpha.S)-
52946-22-2
SCHEMBL17454871
PD046214
Galangal acetate
1'-Acetoxychavicol
(1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate
JAMQIUWGGBSIKZ-ZDUSSCGKSA-N
Q27070798
CCRIS 7708

MDL Number

MFCD32874635

Customs Code

2915390090

FAQ

What are the physical and chemical properties of (1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate (CAS: 52946-22-2)?

(1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate (CAS: 52946-22-2) is a colorless to white crystalline solid with a molecular weight of approximately 252.33 g/mol. It has a low solubility in water but is more soluble in organic solvents like ethanol and acetone. The compound is relatively stable under normal conditions but can undergo hydrolysis in the presence of water. It is used as a starting material in organic synthesis and has a pKa of around 14.

How is (1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate (CAS: 52946-22-2) typically synthesized?

(1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate (CAS: 52946-22-2) is synthesized by reacting 2-acetoxybenzaldehyde with propargyl acetate in the presence of a catalytic amount of a Lewis acid like aluminum trichloride. The reaction is typically carried out in an inert solvent such as dichloromethane. The yield is generally between 70-80%, and the stereochemistry at the chiral center is maintained through selective addition. The product is purified by recrystallization from a suitable solvent.

What industries use (1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate (CAS: 52946-22-2)?

(1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate (CAS: 52946-22-2) is used in the pharmaceutical industry as a precursor for the synthesis of various bioactive molecules. It is also employed in the production of polymer additives and as a fragrance intermediate in the chemical industry. Additionally, it can be utilized in the development of sensors and semiconductors due to its functional groups and structural features.

What precautions should be taken when handling (1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate (CAS: 52946-22-2)?

When handling (1S)-1-[4-(acetyloxy)phenyl]prop-2-en-1-yl acetate (CAS: 52946-22-2), it is important to wear appropriate personal protective equipment (PPE), including gloves and eye protection. Work should be conducted in a well-ventilated fume hood due to its potential volatility. Spills should be handled carefully and cleaned with appropriate solvents. Always consult the Safety Data Sheet (SDS) for detailed handling instructions and emergency procedures.