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HomeProduct name list3-Chloro-1-propanol

3-Chloro-1-propanol

Synonym(s):1-Chloro-3-hydroxypropane;Trimethylene chlorohydrin

  • CAS NO.:627-30-5
  • Empirical Formula: C3H7ClO
  • Molecular Weight: 94.54
  • MDL number: MFCD00002943
  • EINECS: 210-992-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-24 19:19:26
3-Chloro-1-propanol Structural

What is 3-Chloro-1-propanol?

Chemical properties

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

The Uses of 3-Chloro-1-propanol

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.

Properties of 3-Chloro-1-propanol

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.
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 information for 3-Chloro-1-propanol

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 3-Chloro-1-propanol

InChIKey LAMUXTNQCICZQX-UHFFFAOYSA-N

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