96-24-2

Basic information

• Product Name: 3-Chloro-1,2-propanediol
• Synonyms: ,’-Dihydroxy-iso-propylchloride;1,2-Dihydroxy-3-chloropropane;1,2-Propanediol, 3-dichloro-;1-Chloro-1-deoxyglycerol;1-Chloropropane-2,3-diol;2-Propanediol,3-chloro-1;3-Chloro-1,2-dihydroxypropane;3-Chloro-1,2-propandiol
• CAS NO: 96-24-2
• Molecular Formula: C₃H₇ClO₂
• Molecular Weight: 110.54
• EINECS: 202-492-4
• Product Categories: Aliphatics;Metabolites & Impurities;Methocarbamol;Analytical Standards;Analytical/Chromatography;Building Blocks;Chemical Synthesis;Chromatography;Environmental Standards;Metabolites;Organic Building Blocks;Oxygen Compounds;Pesticides;Pesticides &Polyols;Rodenticides;API Intermediate;fine chemical
• Mol File: 96-24-2.mol
• Article Data: 142

Chemical Properties

• Melting Point: -40°C
• Boiling Point: 213 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear pale yellow/Liquid
• Density: 1.322 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.04 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.480(lit.)
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble
• PKA: 13.28±0.20(Predicted)
• Water Solubility: Soluble
• Merck: 14,2145
• BRN: 635684
• CAS DataBase Reference: 3-Chloro-1,2-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-1,2-propanediol(96-24-2)
• EPA Substance Registry System: 3-Chloro-1,2-propanediol(96-24-2)

Safety Data

• Hazard Codes: T
• Statements: 60-21-23/25-41-39-36-23/24/25-40
• Safety Statements: 53-26-36-39-45-38-36/37/39-28A-36/37
• RIDADR: UN 2689 6.1/PG 3
• WGK Germany: 3
• RTECS: TY4025000
• F: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 96-24-2(Hazardous Substances Data)

Usage

Description

3-Chloro-1, 2-propanediol is unusually formed upon the thermal processing of fat-containing foods1. It is useful in organic synthesis. It is an intermediate for the drug dyphylline; used as a solvent for acetate, etc., and as an intermediate for plasticizers, surfactants, and dyes2; be used as a solvent for preparing a plasticizer, a surfactant, a dye intermediate, a drug, or as a dye intermediate mainly for use as an acetyl fiber or the like. Also used as a plasticizer, surfactant and dye intermediate. In the pharmaceutical industry, it is used in the production of phlegm and phlegm and phlegm-removing guaiac oil ether, antiasthmatic drug theophylline, and hydroxyphylline. It is warned that it is a potential carcinogen and has antifertility activity1,3.

Sources

https://en.wikipedia.org/wiki/3-MCPD https://www.sigmaaldrich.com/catalog/product/aldrich/107271?lang=en®ion=US Gunn, S. A., T. C. Gould, and W. A. Anderson. "Possible mechanism of posttesticular antifertility action of 3-chloro-1, 2-propanediol. " Proceedings of the Society for Experimental Biology & Medicine Society for Experimental Biology & Medicine 132.2(1969): 656.

Chemical Properties

Clear pale yellow liquid

Uses

Different sources of media describe the Uses of 96-24-2 differently. You can refer to the following data:
1. To lower the freezing point of dynamite; in the manufacture of dye intermediates. As rodent chemosterilant.
2. (±)-3-Chloro-1,2-propanediol may be used as a reference standard for the determination of (±)-3-chloro-1,2-propanediol in food samples by gas chromatography with mass spectrometric detection (GC-MS).
3. It is used in the synthesis of glycerol esters,amines, and other derivatives; to lower thefreezing point of dynamite; and as a rodentchemosterilant (Merck 1989).

Definition

ChEBI: A chloropropane-1,2-diol that is propane-1,2-diol substituted by a chloro group at position 3.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 1, p. 294, 1941Synthetic Communications, 24, p. 1959, 1994 DOI: 10.1080/00397919408010203Synthesis, p. 295, 1989

General Description

A colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.

Reactivity Profile

3-Chloro-1,2-propanediol is hygroscopic and may be sensitive to prolonged exposure to air. Glycols and their ethers undergo violent decomposition in contact with approximately 70% perchloric acid. .

Health Hazard

Different sources of media describe the Health Hazard of 96-24-2 differently. You can refer to the following data:
1. Glycerol α-monochlorohydrin is a highlytoxic, teratogenic, and carcinogenic com pound. It is also an eye irritant.Inhalation of 125 ppm in 4 hours wasfatal to rats. The lethal dose on mice viaintraperitoneal route was 10 mg/kg. Lowdosage can cause sleepiness, and on chronicexposure, weight lossLD50 value, oral (rats): 26 mg/kThis compound is a strong teratomer,causing severe reproductive effects. Animal studies indicated that the adverse effects wereof spermatogenesis type, related to the testes,sperm duct, and Cowper’s gland. These werepaternal effectsStudies on rats indicated that high exposure levels to glycerol chlorohydrin can giverise to thyroid tumors.
2. TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

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.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by inhalation. Experimental reproductive effects. A severe eye irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. A chemosterilant for rodents. Combustible when exposed to heat or flame. Reaction with perchloric acid forms a sensitive explosive product more powerful than glyceryl nitrate. When heated to decomposition it emits toxic fumes of Cl-.

Waste Disposal

Chemical incineration is the most appropriatemethod of disposal.

InChI:InChI=1/C3H7ClO2/c4-2-1-3(5)6/h3,5-6H,1-2H2

Upstream product

• 51483-40-0 1,3-dibromo-2-chloro-propane 
• 563-63-3 silver(I) acetate 
• 556-52-5 oxiranyl-methanol 
• 107-18-6 allyl alcohol 
• 56-81-5 glycerol 
• 107-05-1 3-chloroprop-1-ene 
• 106-89-8 epichlorohydrin 
• 110-65-6 1,4-dihydroxybut-2-yne 
• 321997-45-9 hypophosphorous acid 2-hydroxypropyl ester 
• 5503-32-2 2-1,4-dioxaspiro<4,5>decane 
• 66089-98-3 methyl-2 phenyl-2 chloromethyl-4 dioxolanne-1,3 
• 71-41-0 pentan-1-ol 
• 127-65-1 chloroamine-T 
• 75-56-9 methyloxirane 

Downstream Products

• 4847-93-2 3-piperidin-1-yl-propane-1,2-diol 
• 58403-04-6 4-chloromethyl-2-furan-2-yl-[1,3]dioxolane 
• 13729-88-9 1-(2,3-dihydroxy-propyl)-quinolinium; chloride 
• 5579-92-0 1-(2,3-dihydroxy-propyl)-3,5-diiodo-1H-pyridin-4-one 
• 479-18-5 diprophylline 
• 13460-96-3 1-(2,3-dihydroxy-propyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione 
• 109812-05-7 3-(2,3-dihydroxy-propyl)-2-phenyl-3H-quinazolin-4-one 
• 111038-24-5 7-(2,3-Dihydroxypropyl)-8-bromotheophylline 
• 869-50-1 1,2-diacetoxy-3-chloro-propane 
• 69828-78-0 3-[1]naphthylamino-propane-1,2-diol 
• 72045-01-3 3-(4-n-hexylphenoxy)-propane-1,2-diol 
• 64049-49-6 4-(2,3-dihydroxypropoxy)benzaldehyde 
• 64049-48-5 2-(2,3-dihydroxy-propoxy)-benzaldehyde 
• 99360-02-8 phenyl-carbamic acid-(3-chloro-2-hydroxy-propyl ester) 

Relevant articles and documents

Thermokinetics of reactions with liquid-liquid phase separation

Isothermal heat flow calorimetry with controlled thermoelectric cooling resp. heating is applied to study the critical slowing down of the kinetics of reactions with liquid-liquid phase separation. Results (i) on the acid-catalysed hydrolysis of chloromethyloxirane by water, and (ii) on the ring-opening and esterification of bromomethyloxirane by dichloroacetic acid in the presence of cyclohexane as an inert solvent, both at 298.15 K, are presented. The heat production w(t) which is proportional to the reaction rate ?ζ/?t (where ζ, is the reaction coordinate) exhibits a funnel-like fall-off when the reaction path intersects the binodal curve at the critical solution point CP. From the shape of this part of the w(t) curves an average value of the critical exponent Φ = 0.72±0,003, which refers to the change of ζ with t at constant T and p, is calculated. This result is to be compared with the theoretical value of Φ = 0.708 obtained from a modification of the Griffiths and Wheeler theory of critical points in multicomponent systems to chemically reacting systems far from equilibrium by introducing f as an additional extensive variable. This allows the critical slowing down of the reaction rates to be interpreted as resulting from the divergence of the correlation length ζ, resp. from the convergence of the transport phenomena to zero at the CP. ? VCH Verlagsgesellschaft mbH, 1996.

A Scalable and Efficient Synthesis of 3-Chloro-1,2-propanediol

-

Method for producing 3-chloro-1,2-propylene glycol by using acetic anhydride-modified graphene oxide

The invention relates to a method for producing 3-chloro-1,2-propylene glycol by using an acetic anhydride-modified graphene oxide catalyst. The method comprises the following steps: using solid acetic anhydride-modified graphene oxide (AGO) as a catalyst, adding hydrochloric acid and glycerol into a reaction kettle, performing heating to 50-110 DEG C in a nitrogen atmosphere, performing stirringreaction for 2-10 hours, performing cooling to 30-60 DEG C, centrifugally separating the catalyst and a reaction solution, and rectifying the reaction liquid under reduced pressure to obtain a product3-chloro-1,2-propylene glycol shown in a formula (I). The method is simple in process, and the catalyst can be recycled. The conversion rate of the reactant glycerol can reach 95% or above, and the selectivity of the product 3-chloro-1,2-propylene glycol can reach 80% or above.

Preparation method for 1,3-propylene glycol from glycerol

The invention relates to a preparation method for 1,3-propylene glycol from glycerol, wherein the preparation method comprises the steps of chlorohydrination reaction, cyclization reaction, hydrogenation reaction and the like. The glycerin conversion rate of the preparation method reaches 99% or above, the yield of 1,3-propylene glycol reaches 65% or above, and the preparation method has the advantages of being simple in process, mild in reaction condition, small in investment, high in technical safety and easy to operate and control.

Sterically controlling 2-carboxylated imidazolium salts for one-step efficient hydration of epoxides into 1,2-diols

In order to overcome the disadvantages of excessive water and many byproducts in the conventional process of epoxide hydration into 1,2-diols, 2-carboxylated imidazolium salts were first adopted as efficient catalysts for one-step hydration of epoxides into 1,2-diols. By regulating the cation chain lengths, different steric structures of 2-carboxylated imidazolium salts with chain lengths from C1 to C4 were prepared. The salt with the shortest substituent chain (DMIC) exhibited better thermal stability and catalytic performance for hydration, achieving nearly 100% ethylene oxide (EO) conversion and 100% ethylene glycol (EG) selectivity at 120 °C, 0.5 h with just 5 times molar ratio of H2O to EO. Such a tendency is further confirmed and explained by both XPS analysis and DFT calculations. Compared with other salts with longer chains, DMIC has stronger interaction of CO2?anions and imidazolium cations, exhibiting a lower tendency to release CO2?and form HO-CO2?, which can nucleophilically attack and synergistically activate ring-opening of epoxides with imidazolium cations. The strong huge sterically dynamic structure ring-opening transition state slows down the side reaction, and both cations and anions stabilized the transition state imidazolium-EG-HO-CO2?, both of which could avoid excessive hydration into byproducts, explaining the high 1,2-diol yield. Based on this, the cation-anion synergistic mechanism is then proposed.