503-09-3

Basic information

• Product Name: Epifluorohydrin
• Synonyms: (fluoromethyl)oxirane;1,2-epoxy-3-fluoro-propan;1-fluoro-2,3-epoxypropane;2-(Fluoromethyl)oxirane;3-Fluoropropene-1,2-oxide;Epifluorhydrine;Propane, 1,2-epoxy-3-fluoro-;1,2-EPOXY-3-FLUOROPROPANE
• CAS NO: 503-09-3
• Molecular Formula: C₃H₅FO
• Molecular Weight: 76.07
• EINECS: 207-960-1
• Product Categories: monomer;Contact Printing;Fluorine-Containing Monomers for 157 nm UV Lithography Resist Polymers;Lithography Monomers;Self Assembly &Building Blocks;Chemical Synthesis;Epoxides;Fluorinated Building Blocks;Heterocyclic Fluorinated Building Blocks;Materials Science;Micro/NanoElectronics;Organic Building Blocks;Other Fluorinated Heterocycles;Oxygen Compounds
• Mol File: 503-09-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 85-86 °C(lit.)
• Flash Point: 40 °F
• Appearance: clear, colorless liquid.
• Density: 1.067 g/mL at 25 °C(lit.)
• Vapor Pressure: 77.4mmHg at 25°C
• Refractive Index: n20/D 1.368(lit.)
• Storage Temp.: 0-6°C
• CAS DataBase Reference: Epifluorohydrin(CAS DataBase Reference)
• NIST Chemistry Reference: Epifluorohydrin(503-09-3)
• EPA Substance Registry System: Epifluorohydrin(503-09-3)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-34
• Safety Statements: 16-26-45-38-36/37/39-33
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• RTECS: TZ3325000
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 503-09-3(Hazardous Substances Data)

Usage

Description

Epifluorohydrin, also known as 3,4-epoxy-1-butene or 1,2-epoxy-3-fluoropropane, is a clear colorless liquid with chemical properties that make it a versatile compound in various industries. It is characterized by its epoxide and fluoroalkene functional groups, which contribute to its unique reactivity and applications.

Uses

Used in Pharmaceutical Industry:
Epifluorohydrin is used as a reagent for the synthesis of N-arylphosphoramidates, which are important compounds in the development of pharmaceuticals. These compounds have potential applications in the treatment of various diseases and disorders.
Used in Oncology:
In the field of oncology, Epifluorohydrin is utilized in the synthesis of orally bioavailable ALK inhibitors. These inhibitors play a crucial role in the treatment of tumors, particularly those associated with the anaplastic lymphoma kinase (ALK) gene mutation. The development of such inhibitors can significantly improve the prognosis and quality of life for patients suffering from tumor-related conditions.
Used in Chemical Synthesis:
Due to its unique chemical properties, Epifluorohydrin is also employed as an intermediate in the synthesis of various chemicals and materials. Its epoxide and fluoroalkene functional groups make it a valuable building block for creating a wide range of products, including specialty polymers, agrochemicals, and other industrial chemicals.

Air & Water Reactions

Highly flammable. Water soluble.

Reactivity Profile

A halogenated epoxide. Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts. The chlorinated derivative has been shown to be incompatible with aniline, strong oxidizers, sulfuric acid, isopropylamine, zinc, aluminum, iron, etc. see epichlorohydrin.

Health Hazard

ACUTE/CHRONIC HAZARDS: Epifluorohydrin is a lacrimator. When heated to decomposition it emits toxic fumes.

Fire Hazard

Epifluorohydrin is flammable.

InChI:InChI=1/C3H5FO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m1/s1

Upstream product

• 26198-63-0 1,2-Dichloropropane 
• 96-23-1 1,3-Dichloro-2-propanol 
• 68064-54-0 2-bromo-3-fluoropropan-1-ol 
• 818-92-8 3-fluoropropene 
• 15464-00-3 azobisisopropane 
• 106-89-8 epichlorohydrin 

Downstream Products

• 329259-53-2 (S)-5-Benzyl-1-(3-fluoro-2-hydroxy-propyl)-2,2,3-trimethyl-imidazolidin-4-one 
• 32860-39-2 (2R)-3-fluoropropane-1,2-diol 
• 33644-25-6 (2S)-3-fluoropropane-1,2-diol 
• 83398-56-5 (R)-3-fluoro-1,2-epoxypropane 
• 112482-36-7 1-fluoro-3-(phenylmethoxy)propan-2-ol 
• 142545-51-5 3-fluoro-1,2-propanediol 1-O-(4-methylbenzene)sulphonate 
• 1443744-65-7 C₁₉H₂₁FN₄O₄S 
• 1353898-50-6 C₁₅H₁₉FN₂O₄ 
• 453-16-7 3-fluoropropane-1,2-diol 

Relevant articles and documents

PROCESS FOR MANUFACTURING AN EPOXIDE

Process for manufacturing an epoxide by reacting at least one chlorohydrin with at least one dehydrochlorinating agent in order to give the epoxide and at least one chlorinated co-product, said process comprising regenerating the dehydrochlorinating agent from the chlorinated co-product by a treatment which does not comprise an electrolysis operation.

SYNTHESIS OF ISOMERIC N-(3-FLUORO-2-HYDROXYPROPYL) AND N-(2-FLUORO-3-HYDROXYPROPYL) DERIVATIVES OF PURINE AND PYRIMIDINE BASES

Reaction of fluoromethyloxirane (III) with heterocyclic bases in the presence of potassium carbonate afforded N-(3-fluoro-2-hydroxypropyl) derivatives of adenine (VI), 3-deazaadenine (VII), 2-amino-6-chloropurine (XII), 6-nitro-1-deazapurine (IX), 4-methoxy-2-pyrimidone (XVIII) and its 5-methyl derivative (XIX).Acid hydrolysis of compounds XII, XVIII, and XIX gave 9-(3-fluoro-2-hydroxypropyl)guanine (XIII), 1-(3-fluoro-2-hydroxypropyl)uracil (XX) and -thymine (XXI).The intermediates XVIII and XIX were ammonolyzed to give 1-(3-fluoro-2-hydroxypropyl)cytosine (XXII) and -5-methylcytosine (XXIII).Reaction of chloro derivative XII with sodium azide followed by hydrogenation of the formed 2-amino-6-azidopurine (XIV) led to 9-(3-fluoro-2-hydroxypropyl)-2,6-diaminopurine (XV), 9-(3-fluoro-2-hydroxypropyl)-1-deazaadenine (X) was obtained by hydrogenation of compound IX.Benzyloxymethyloxirane (XXIV) was reacted with pyridine-hydrogen fluoride adduct to give 3-benzyloxy-2-fluoropropanol (XXV) whose tosylate XXVI on reaction with sodium salt of adenine and subsequent hydrogenolysis of the intermediate XXVII afforded 9-(2-fluoro-3-hydroxypropyl)adenine (XXVIII).The same compound was obtained by reaction of 3-benzoyloxy-1-bromo-2-fluoropropanol (XXX) with sodium salt of adenine followed by methanolysis.Condensation of sodium salt of XI, XVI, and XVII with synthon XXX and subsequent acid deblocking gave 9-(2-fluoro-3-hydroxypropyl)guanine (XXXIII), 1-(2-fluoro-3-hydroxypropyl)uracil (XXXVI), and 1-(2-fluoro-3-hydroxypropyl)thymine (XXXVII). 1-(2-Fluoro-3-hydroxypropyl) derivatives of cytosine (XXXVIII) and 5-methylcytosine (XXXIX) were obtained by ammonolysis of the corresponding 4-methoxypyrimidine intermediates XXXIV and XXXV.

The Combination of Potassium Fluoride and Calcium Fluoride: A Useful Heterogeneous Fluorinating Reagent

The combination of potassium fluoride and calcium fluoride was found to be an effective and practical solid reagent for the fluorination of various organic chlorides and bromides under mild conditions.