3-Chloro-1-propanol Property

Melting point:

-20 °C

Boiling point:

160-162 °C(lit.)

Density 

1.131 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.445(lit.)

Flash point:

164 °F

storage temp. 

0-6°C

solubility 

50g/l (slow decomposition)

form 

Liquid

pka

14.73±0.10(Predicted)

Specific Gravity

1.14

color 

Clear colorless to yellow

PH

3-4 (100g/l, H2O, 20℃)

Water Solubility 

300 g/L (20 ºC)

BRN 

773655

Exposure limits

No exposure limit is set. A TLV-TWA air value of 100 ppm (approximately 400 mg/m³) is suggested for this compound.

Stability:

Stability Stable, but light-sensitive. Combustible. Incompatible with strong oxidizing agents.

InChIKey

LAMUXTNQCICZQX-UHFFFAOYSA-N

CAS DataBase Reference

627-30-5(CAS DataBase Reference)

NIST Chemistry Reference

1-Propanol, 3-chloro-(627-30-5)

EPA Substance Registry System

3-Chloro-1-propanol (627-30-5)

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36-36/37/39

RIDADR 

UN 2849 6.1/PG 3

WGK Germany 

3

RTECS 

UA8930000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29055910

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

3-Chloro-1-propanol Chemical Properties,Usage,Production

Chemical Properties

Colorless to pale-yellow liquid; characteristic odor. Soluble in water, alcohols, and ethers; insoluble in hydrocarbons. Combustible.

Uses

3-Chloro-1-propanol is used in organicsynthesis to produce cyclopropane andtrimethylene oxide. It is an intermediate inthe synthesis of pharmaceuticals, agrochemicals, antiseptic agents, and dyes. It is an inhibitor of triosephosphate isomerase and glyceraldehyde 3-phosphate dehydrogenase.

Preparation

3-Chloro-1-propanol is synthesized by the reaction of 1, 3-propanediol and hydrochloric acid, using benzene sulfonic acid as the catalyst.
Reaction: 250 g of trimethylene glycol are shaken with 450 g of sulfur chloride, the mixture becoming warm, sulfur dioxide being rapidly evolved, and sulfur deposited. This reaction continues for 1 hours without heating, whereafter the mixture is heated for a further 6 hours on the water-bath and then for 30 min, over a free flame. When no more sulfur dioxide is evolved, the mixture is allowed to cool, then extracted several times with ether. The sulfur is washed with ether, and the united ethereal layers are shaken with sodium carbonate solution to remove sulfur dioxide, dried over sodium sulfate, and freed from ether. The residue is fractionated and the fraction of b.p. 140-180° C is redistilled, giving 60% (160 g) of 3-chloro-1-propanol, b.p. 160-164°C/760 mm, 60-64° C/10 mm.
J. Amer. Chem. Soc, 38, 2481 (1916)
J. Chem. Soc, 1928, 2439

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 2927, 1968 DOI: 10.1021/ja01013a033
The Journal of Organic Chemistry, 55, p. 2968, 1990 DOI: 10.1021/jo00296a078
Organic Syntheses, Coll. Vol. 1, p. 533, 1941

General Description

3-Chloro-1-propanol appears as a colorless liquid with a mild odor. Slightly denser than water. Toxic by ingestion and inhalation . Flash point 270°F. Used to make plastics, resins and other chemicals.

Reactivity Profile

3-Chloro-1-propanol may be sensitive to prolonged exposure to light. 3-Chloro-1-propanol may react with oxidizing agents. .

Health Hazard

3-Chloro-1-propanol also know as Trimethylene chlorohydrin, is a moderatelytoxic compound. Skin contact can cause irritation.Ingestion can result in CNSdepression, muscle contraction, gastrointesti nal pain, and ulceration or stomach bleed ing. High dosage can cause liver injury. Thetoxicity of this compound, however, is lesssevere than that of its isomer, propylene β-chlorohydrin.
LD50 value, oral (mice): 2300 mg/kg

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Safety Profile

Moderately toxic by ingestion. Mutation data reported. Chloropropanols have mutagenic and carcinogenic properties. The 3-monochloropropanol (3-MCPD) is the main chloropropanol found in hydrolyzates of vegetable protein (HVP) made by acid hydrolysis.

Waste Disposal

Trimethylene chlorohydrin is burned in achemical incinerator equipped with an afterburner and scrubber.