627-30-5 Usage
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/ja01013a033The Journal of Organic Chemistry, 55, p. 2968, 1990 DOI: 10.1021/jo00296a078Organic 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.
Check Digit Verification of cas no
The CAS Registry Mumber 627-30-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 7 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 627-30:
(5*6)+(4*2)+(3*7)+(2*3)+(1*0)=65
65 % 10 = 5
So 627-30-5 is a valid CAS Registry Number.
InChI:InChI=1/C3H7ClO/c4-2-1-3-5/h5H,1-3H2
627-30-5Relevant articles and documents
Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides
Lambert, Tristan H.,Steiniger, Keri A.
supporting information, p. 8013 - 8017 (2021/10/25)
The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.
An Ultrasensitive Fluorescence Assay for the Detection of Halides and Enzymatic Dehalogenation
Aslan-üzel, A?k?n S.,Beier, Andy,Ková?, David,Cziegler, Clemens,Padhi, Santosh K.,Schuiten, Eva D.,D?rr, Mark,B?ttcher, Dominique,Hollmann, Frank,Rudroff, Florian,Mihovilovic, Marko D.,Bury?ka, Tomá?,Damborsky, Ji?í,Prokop, Zbyněk,Badenhorst, Christoffel P. S.,Bornscheuer, Uwe T.
, p. 2032 - 2039 (2020/02/11)
Halide assays are important for the study of enzymatic dehalogenation, a topic of great industrial and scientific importance. Here we describe the development of a very sensitive halide assay that can detect less than a picomole of bromide ions, making it very useful for quantifying enzymatic dehalogenation products. Halides are oxidised under mild conditions using the vanadium-dependent chloroperoxidase from Curvularia inaequalis, forming hypohalous acids that are detected using aminophenyl fluorescein. The assay is up to three orders of magnitude more sensitive than currently available alternatives, with detection limits of 20 nM for bromide and 1 μM for chloride and iodide. We demonstrate that the assay can be used to determine specific activities of dehalogenases and validate this by comparison to a well-established GC-MS method. This new assay will facilitate the identification and characterisation of novel dehalogenases and may also be of interest to those studying other halide-producing enzymes.
ADENOSINE A3 RECEPTOR MODULATING COMPOUNDS AND METHODS OF USE THEREOF
-
, (2012/03/12)
Provided herein is a method of preventing, treating, or ameliorating one or more symptoms of an adenosine A3-mediated condition, disorder, or disease, with a compound of Formula I. Also provided herein is a method of preventing, treating, or ameliorating one or more symptoms of glaucoma or ocular hypertension. Further provided herein is a method of modulating the activity of an adenosine A3 receptor.
