1,4-Pentadien-3-ol Chemical Properties

Boiling point:

115-116 °C (lit.)

Density 

0.865 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.445(lit.)

Flash point:

86 °F

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

pka

13.68±0.20(Predicted)

form 

Liquid

color 

Clear colorless

BRN 

1735809

Stability:

Volatile

InChI

InChI=1S/C5H8O/c1-3-5(6)4-2/h3-6H,1-2H2

InChIKey

ICMWSAALRSINTC-UHFFFAOYSA-N

SMILES

C=CC(O)C=C

CAS DataBase Reference

922-65-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

10-22

RIDADR 

UN 1987 3/PG 3

WGK Germany 

3

HazardClass 

3.2

PackingGroup 

III

HS Code 

29052990

MSDS

• Language:English Provider:Penta-1,4-dien-3-ol
• Language:English Provider:SigmaAldrich

1,4-Pentadien-3-ol Usage And Synthesis

Uses

Starting material for asymmetric epoxidation.1,2

Uses

1,4-Pentadien-3-ol is a valuable building block in natural product synthesis. This chemical is a substrate employed in synthesising amino-substituted dienes via a bismuth-catalyzed SN1 displacement of alcohols by sulfonamide nucleophiles. Starting material for asymmetric epoxidation.

Structure and conformation

1,4-pentadien-3-ol (CH2=CH-CH(OH)-CH=CH2) is a representative allyl alcohol containing two C=C bonds and one hydroxyl group. It has a complicated conformational landscape arising from the rotations of three σ-bonds, i.e. three dihedral angles of ?(C7=C6-C1-O3), ?(C5=C4-C1-O3), and ?(H8-O3-C1-H2). Experiments and ab initio calculations revealed that the 1,4-pentadien-3-ol monomer prefers a configuration with one vinyl being syn to the hydroxyl oxygen and the hydroxyl hydrogen toward the skew-arranged vinyl, which therefore makes possible simultaneous C-H···O and O-H···π interactions[1].

References

[1] Zhen Wang. “Conformations and structures of 1,4-pentadien-3-ol and its water complex characterized by rotational spectroscopy.” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 267 (2022): Article 120589.

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