5-Chloropentanol

5-Chloropentanol Property

Boiling point:

107 °C

Density 

1,06 g/cm³

refractive index 

1.454

Flash point:

102-103°C/8mm

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO, Methanol (Sparingly)

form 

Oil

pka

15.12±0.10(Predicted)

Specific Gravity

1.06

color 

Clear Colourless

Water Solubility 

Slightly soluble in water.

BRN 

1732314

InChIKey

DCBJCKDOZLTTDW-UHFFFAOYSA-N

CAS DataBase Reference

5259-98-3(CAS DataBase Reference)

EPA Substance Registry System

1-Pentanol, 5-chloro- (5259-98-3)

Safety

Hazard Codes 

Xi

Risk Statements 

22-36/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant/Harmful

TSCA 

Yes

PackingGroup 

III

HS Code 

2905190098

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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.

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

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

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

P405Store locked up.

P501Dispose of contents/container to..…

5-Chloropentanol Chemical Properties,Usage,Production

Uses

5-Chloro-1-pentanol is used to produce 6-hydroxy-hexanenitrile at temperature of 90 - 100°C. It is also is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Synthesis

The general procedure for the synthesis of 5-chloro-1-pentanol from 5-chloropentyl acetate was as follows: 5-chloropentanol-1-acetate (33.9 g, 0.21 mol) was mixed with 95% ethanol (75 mL) and 2N aqueous NaOH (90 mL) according to the method reported by Meyers et al. (Tetrahedron 27, 5979-85), and shaken to homogeneous. The mixed solution was allowed to stand at room temperature for a few hours and the ethanol was subsequently removed by distillation under reduced pressure. The residue was extracted with ether (3 x 150 mL). The extract was dried over anhydrous potassium carbonate, the solvent was removed under reduced pressure and finally 5-chloro-1-pentanol was obtained by distillation as a colorless oil (21.1 g, 84% yield, literature value 72%) with a boiling point of 35-37°C (0.02 mmHg) (literature value 62°C (0.5 mmHg)). The product was characterized by the following data: IR (thin film) cm-1 3330 (broad peak), 2945, 2875, 1455, 1440, 1315, 1295, 1265, 1150, 1075, 1060, 1020, 1000, 965, 900, 740, 725, 655; 1H NMR (200 MHz, CDCl3) δ 3.67 (m, 2H), 3.55 (t, J=6.5 Hz, 2H), 1.82 (pentet, J=7 Hz, 2H), 1.4-1.7 (m, 4H), 1.37 (m, 1H); 13C NMR (22.5 MHz, CDCl3) δ 62.4, 45.0, 32.4, 31.9, 23.2; Mass Spectra (70 eV) m/z (relative abundance) 124, 122 (M+, not observed), 106, 104 (M+ - H2O, 0.7, 1.3), 105 (0.5), 93 (7.1), 91 (20.5), 69 (13.7), 68 (100.0), 67 (13.6), 57 (13.4), 56 (41.4), 55 ( 57.0).

References

[1] Journal of the American Chemical Society, 1983, vol. 105, # 12, p. 4008 - 4017
[2] Synthetic Communications, 1985, vol. 15, # 7, p. 569 - 580
[3] Patent: US5264619, 1993, A
[4] Journal of Organic Chemistry, 1981, vol. 46, # 16, p. 3361 - 3364
[5] Phosphorus and Sulfur and the Related Elements, 1987, vol. 31, p. 161 - 176