78385-26-9

Usage

Uses

Used in Propellant Formulations:
3-BROMOMETHYL-3-METHYLOXETANE is used as a monomer for the synthesis of Poly 3-bromomethyl-3-Me oxetane (PolyBrMMO), an energetic thermoplastic elastomer. This polymer is specifically utilized in the development of propellant formulations, offering improved performance and versatility in the field of propulsion technology.

InChI:InChI=1/C5H9BrO/c1-5(2-6)3-7-4-5/h2-4H2,1H3

Upstream product

• 3143-02-0 3-hydroxymethyl-3-methyloxethane 
• 558-13-4 carbon tetrabromide 
• 603-35-0 triphenylphosphine 
• 77-85-0 2-(hydroxymethyl)-2-methylpropane-1,3-diol 
• 99314-44-0 (3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate 

Downstream Products

• 206191-46-0 (2S,3R)-2-Benzyloxycarbonylamino-3-hydroxy-butyric acid 3-methyl-oxetan-3-ylmethyl ester 
• 150672-50-7 (2S,3R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyric acid 3-methyl-oxetan-3-ylmethyl ester 
• 148150-67-8 N-(9-fluorenylmethyloxycarbonyl)-L-serine 3-methyl-3-(hydroxymethyl)oxetane ester 
• 497870-35-6 3-methyloxetan-3-ylmethyl [4-(3-methyloxetan-3-ylmethoxy)phenyl]acetate 
• 497870-34-5 3-methyloxetan-3-ylmethyl 4-(3-methyloxetan-3-ylmethoxy)benzoate 
• 329041-34-1 (2R,3S)-2-Benzyloxycarbonylamino-3-hydroxy-butyric acid 3-methyl-oxetan-3-ylmethyl ester 
• 613264-80-5 (S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(3-methyl-oxetan-3-ylmethyl) ester 
• 531521-23-0 3-[(2-(2-methoxyethoxy)ethoxy)methyl]-3-methyloxetane 
• 78385-27-0 2,9-bis(methoxymethyl)-2,9-dimethyl-4,7-dioxadecane-1,10-diol 
• 870481-55-3 2,2-bis[4-(3-methyl-3-oxetanyl)methoxyphenyl]propane 
• 1258452-60-6 4-bromo-1-((3-methyloxetan-3-yl)methyl)-1H-pyrazole 
• 117452-93-4 [3-(hydromethyl)oxetan-3-yl]acetonitrile 
• 879546-73-3 3-methyl-3-(2,2,3,3,4,4,5,5-octafluoropentyloxymethyl)oxetane 
• 449177-94-0 3-[(2,2,3,3,3-pentafluoropropoxy)methyl]-3-methyloxetane 

Relevant academic research and scientific papers

OXYSTEROLS AND METHODS OF USE THEREOF

Compounds are provided according to Formula (A): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1, R2, R3, R4, R5, R6, and RG are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

Synthesis and copolymerization of azidomethyl-substituted oxetanes: the morphology of statistical block copolymers

[Figure not available: see fulltext.] 3,3-Bis(azidomethyl)oxetane and 3-azidomethyl-3-methyloxetane were obtained by bromination of pentaerythritol and metriol with a mixture of hydrobromic, acetic, and sulfuric acids, followed by cyclization in the presence of a phase-transfer catalyst TBAB, with the formation of oxetane ring and replacement of bromide substituents with azide ions. The copolymerization reaction of 3,3-bis-(azidomethyl)oxetane and 3-azidomethyl-3-methyloxetane was performed in the presence of a catalytic system prepared from triisobutylaluminum and water. The methods of small-angle and wide-angle X-ray diffraction analysis were used to determine the amorphous-crystalline and domain structures of the synthesized copolymers. We also present data about conformational and relaxation transitions in these statistical copolymers.

Synthesis and characterization of environmentally benign, semifluorinated polymers and their applications in drug delivery

We describe the synthesis, physicochemical studies and pharmaceutical assessment of a class of pegylated semifluorinated amphiphilic block-copolymers based on short pendant fluorinated side chains attached to moderately hydrophobic units. These polymers allowed us to investigate how the balance between hydrophobicity and fluorophilicity in the polymer can be tuned to match that of small molecules to be used in drug delivery. Remarkably, we found that using short perfluoroethyl groups in the polymer allows the preferential stabilization of nanoemulsions based on isoflurane, a fluorinated anesthetic made partly hydrophobic by the presence of a chlorine atom. In comparison, nanoemulsions of sevoflurane, a purely fluorophilic anesthetic, were not as stable. The lipophilicity of the polymers was also investigated in regards to solvation of hydrophobic molecules. Surface properties such as critical micelle concentration (CMC) and surface tension demonstrated the uniqueness of these fluorinated amphiphiles. Finally, the use of short perfluoroethyl chains makes these polymers environmentally benign in terms of bioaccumulation and toxicity.

A ruthenium-catalyzed hydrosilane-induced polymerization of 3-alkyl-3-hydroxymethyloxetane derivatives: Facile access to functionalized polyoxetanes by virtue of organosilyl groups

Ring-opening polymerization of 3-alkyl-3-alkoxymethyl- or 3-alkyl-3-siloxymethyloxetanes is catalyzed by a triruthenium cluster, [Ru 3{μ3-(η2,η3, η5-C12H8)}(CO)7], in the presence of trialkylsilanes, providing a novel accessible method for functionalized polyoxetanes of Mn = 103-105. Oxetanes having alkoxy-, fluoroalkoxy-, triethyleneglycoloxy-, and trialkylsiloxy functions undergo polymerization and copolymerization. Consumption rates of two monomers in the copolymerization of 3-benzyloxymethyl- and 3-trimethylsiloxymethyl-3-alkyloxetanes are almost the same, indicating formation of random copolymers. The organosilyl group in the polymer and copolymers with siloxymethyl side chains is converted to CH3OH or CH2OCOR groups by hydrolysis or silyl/acyl exchange. These protocols give the way to access polymers or copolymers bearing OH and OCOR side chains. A ruthenium-catalyzed reaction of 3-ethyl-3- hydroxymethyloxetane with trialkylsilanes results in dehydrogenative silylation to give 3-ethyl-3-siloxymethyloxetane, which is followed by ring-opening polymerization. Combination of tandem dehydrogenative silylation/ring-opening polymerization/the silyl/acyl exchange realizes one-pot synthesis of polymers with CH2OCOR side chains from 3-ethyl- 3-hydroxymethyloxetane. DSC analyses of the formed polymers provided Tg and Tm data, which are a good example showing that the polymer properties are controlled by appropriate selection of functional groups at the side chain.

OXETANE-CONTAINING COMPOUND, PHOTORESIST COMPOSITION HAVING THE SAME, METHOD OF PREPARING PATTERN USING THE PHOTORESIST COMPOSITION, AND INKJET PRINT HEAD INCLUDING POLYMERIZATION PRODUCTS OF THE OXETANE-CONTAINING COMPOUND

An oxetane-containing compound, a photoresist composition including the same, a method of preparing patterns using the photoresist composition, and an inkjet print head including polymerization products of the oxetane-containing compound.

Oxetane-containing compound, photoresist composition having the same, method of preparing pattern using the photoresist composition, and inkjet print head including polymerization products of the oxetane-containing compound

An oxetane-containing compound, a photoresist composition including the same, a method of preparing patterns using the photoresist composition, and an inkjet print head including polymerization products of the oxetane-containing compound.

Selective inhibition of aggrecanase in osteoarthritis treatment

This invention relates to a method of treatment for osteoarthritis involving inhibitors of aggrecanase that demonstrate IC50s of less than 20 nM and demonstrate differential potency against matrix metalloproteinases (MMPs) and a disintegrin and

Isomerization of cyclic ethers having a carbonyl functional group: New entries into different heterocyclic compounds

Oxiranes (epoxides) and oxetanes having a carbonyl functional group are chemoselectively isomerized to different heterocyclic compounds via Lewis acid-promoted 1,6- and 1,7-intramolecular nucleophilic attacks of the carbonyl oxygen on the electron-deficient carbon neighboring the oxonium oxygen: for example, cyclic imides to bicyclic acetals, esters to bicyclic orthoesters, sec-amides to 4,5-dihydrooxazole or 5,6-dihydro-4H-1,3-oxazines, and tert-amides to bicyclic acetals or azetidines. The intramolecular attack of a 1,5-positioned carbonyl oxygen predominantly results in a propagating-end isomerization polymerization. On the other hand, cyclic ethers having a 1,8- or farther positioned carbonyl group undergo conventional ring-opening polymerization. A tetrahydrofuran (oxolane) ring does not open, even with a 1,6-positioned carbonyl group.

Selective inhibitors of aggrecanase in osteoarthritis treatment

This invention relates to a method of treatment for osteoarthritis involving inhibitors of aggrecanase that demonstrate IC50s of less than 20 nM and demonstrate differential potency against matrix metalloproteinases (MMPs) and a disintegrin and metalloproteinases (ADAMs or reprolysins). This invention also relates to compounds, methods of treatment and composition of Formula I: or a therapeutically acceptable salt thereof, whereinX is carbon or nitrogen;R1 and R2 are independently selected from the group consisting of hydrogen, hydroxy, and methyl, wherein at least one of R1 and R2 is methyl;R3 and R4 are independently selected from the group consisting of hydrogen, hydroxy, and methyl, or R3 and R4 may be taken together to form a carbonyl group; andR5 and R6 are independent substituents in the ortho, meta, or para positions and are independently selected from the group consisting of hydrogen, halogen, cyano, methyl, and ethyl;with the provisos:when X is carbon, then R7 and R8 are both hydrogen and at least one of R1, R2, R3, and R4 is hydroxy;when X is carbon and R5 is para-halo, then at least one of R6, R3, and R4 is not hydrogen;when X is nitrogen, then R8 is not present and R7 is hydrogen or a group of the formula:wherein, Y is -CH2-NH2 or -NH-CH3; andwhen X is nitrogen and R7 is H, then R3 and R4 are taken together to form a carbonyl group.

Stereoselective Synthesis of Threo and Erythro β-Hydroxy and β-Disubstituted-β-Hydroxy α-Amino Acids

Optically pure N-protected serine aldehyde equivalents can be prepared by the protection of the carboxylic group of serine by a cyclic ortho ester. Alkylation of N-Cbz-, N-Fmoc- or N-Boc-protected serine with oxetane tosylate 1 or bromide 2 gives the corresponding oxetane esters 4a-c which can easily be converted to the cyclic ortho esters 5a-c. A variety of unusual threo β5-hydroxy amino acids have been synthesized by Grignard addition to these optically pure serine aldehyde equivalents. The erythro diastereomers can be obtained by oxidation of the initial threo adduct followed by reduction with LiBH4. Also described is a general approach for the diastereoselective synthesis of optically pure β,β-dialkyl-β-hydroxy α-amino acids. These highly substituted amino acids are prepared by a sequence of Grignard addition to the optically active serine aldehyde equivalent, followed by oxidation of the initial adduct, and a second Grignard addition to the resulting ketone. The hydroxy adduct is obtained with very high diastereoselectivity (84-96% de). All four diastereomers can be selectively synthesized by varying the order of the Grignard additions and the chirality of the initial synthon. Removal of the protecting groups can be effected in very mild conditions, giving excellent yields of highly substituted amino acids in high diastereomeric purity.