(Z)-3-Methylpent-2-en-4-yn-1-ol

(Z)-3-Methylpent-2-en-4-yn-1-ol Property

Boiling point:

171°C

Density 

0.940

refractive index 

1.4445-1.4465

Flash point:

65°C

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Oil

pka

13.80±0.10(Predicted)

color 

Yellow to Dark Yellow

InChI

InChI=1S/C6H8O/c1-3-6(2)4-5-7/h1,4,7H,5H2,2H3/b6-4-

InChIKey

ZSJHASYJQIRSLE-XQRVVYSFSA-N

SMILES

C(O)/C=C(/C)\C#C

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-37/39

RIDADR 

UN 1760

HazardClass 

8

PackingGroup 

III

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H319Causes serious eye irritation

Precautionary statements

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

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

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.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

(Z)-3-Methylpent-2-en-4-yn-1-ol Chemical Properties,Usage,Production

Uses

(Z)-3-Methylpent-2-en-4-yn-1-ol is used as a reagent in organic synthesis of many compounds including that of prolycopene which is a tangerine-colored tetra-Z-isomer of lycopene that is found in fruits of the tangerine tomato. Z)-3-Methylpent-2-en-4-yn-1-ol is also used in the synthesis of Leucosceptroids A and B which have potent antifungal properties.

Synthesis

The general procedure for the synthesis of (Z)-3-methylpent-3-en-1-yn-5-ol from 3-methyl-1-penten-4-yn-3-ol was as follows: 100.0 g of 3-methyl-1-penten-4-yn-3-ol (a compound of formula (1)) was dissolved in 500.0 g of isopropyl ether, and 20.0 g of catalyst containing 96% of the catalyst was added followed by addition of dilute sulfuric acid (containing 0.1%) and pH was adjusted to 2.0-3.0. The reaction mixture was heated to 34?36°C in a water bath with continuous stirring for 60 min. Upon completion of the reaction, 610.3 g of the organic oil layer solution was obtained by separation using a 1000 ml dispensing funnel, of which (Z)-3-methylpent-3-en-1-yn-5-ol (compound (2)) was determined to be 13.5% by gas phase internal standard method. The above organic oil layer was washed twice with 2 x 150.0 ml saturated NaHCO3 solution, followed by washing with water and vacuum to remove the isopropyl ether, and the concentrate was obtained by neutralization via heat recovery. The concentrate was subjected to reduced pressure distillation via an oil pump and the fractions were collected to give 81.1 g of (Z)-3-methylpent-3-en-1-yn-5-ol (cis (2)), which was determined to be 98.5% pure by gas phase internal standard method. The yield based on the feedstock 3-methyl-1-penten-4-yn-3-ol was 79.8%. The mass of residue (3) was 36.4 g, in which the ratio of raw material 3-methyl-1-penten-4-yn-3-ol to residue (3) was 30.3%.

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2841 - 2846
[2] Bulletin de la Societe Chimique de France, 1973, p. 2331 - 2335
[3] Tetrahedron, 1998, vol. 54, # 24, p. 6677 - 6698
[4] Synlett, 1998, # 4, p. 373 - 374
[5] Patent: CN104649861, 2016, B. Location in patent: Paragraph 0030-0032