17247-58-4

Basic information

• Product Name: (Bromomethyl)cyclobutane
• Synonyms: CYCLOBUTYLMETHYL BROMIDE;(BROMOMETHYL)CYCLOBUTANE;(Bromomethyl)codobutane;Cyclobutane, (bromomethyl)-;(BROMOMETHYL)CYCLOBUTANE 99%;(Bromomethyl)cyclobutane,99%;(Bromomethyl)cyclobutaneCyclobutylmethyl bromide;(Bromomethyl)cyclobu
• CAS NO: 17247-58-4
• Molecular Formula: C₅H₉Br
• Molecular Weight: 149.03
• Product Categories: Cycloalkanes
• Mol File: 17247-58-4.mol

Chemical Properties

• Boiling Point: 123-124 °C(lit.)
• Flash Point: 97 °F
• Appearance: Clear colorless/Liquid
• Density: 1.326 g/mL at 25 °C(lit.)
• Vapor Pressure: 15.7mmHg at 25°C
• Refractive Index: n20/D 1.48(lit.)
• Storage Temp.: Flammables area
• Water Solubility: 80mg/L at 20℃
• CAS DataBase Reference: (Bromomethyl)cyclobutane(CAS DataBase Reference)
• NIST Chemistry Reference: (Bromomethyl)cyclobutane(17247-58-4)
• EPA Substance Registry System: (Bromomethyl)cyclobutane(17247-58-4)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 17247-58-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(Bromomethyl)cyclobutane is used as a synthetic intermediate for the production of racemic 3-cyclobutylalanine, which is an essential component in the development of pharmaceuticals. Its application in this context is due to its ability to react with various hydroxychromen-4-one derivatives, facilitating the creation of complex molecular structures.
Additionally, (Bromomethyl)cyclobutane is used as a synthetic intermediate for the production of 17-(cyclobutylmethyl)morphinan-3-ol (butorphan), a potent opioid analgesic. The compound's utility in this application stems from its capacity to form meta-depside bonds during the synthesis process, which contributes to the overall effectiveness of the final product.
Used in Chemical Research:
In the field of chemical research, (Bromomethyl)cyclobutane serves as a valuable building block for the exploration of new chemical reactions and the development of novel compounds. Its reactivity with anhydrous K2CO3/dry acetone and Bu4N+I(PTC) has been investigated, providing insights into its potential applications and the types of reactions it can undergo.
Overall, (Bromomethyl)cyclobutane is a versatile compound with applications in both the pharmaceutical industry and chemical research, making it an important tool for scientists and researchers in their quest to develop new drugs and understand complex chemical reactions.

Preparation

The preparation of (Bromomethyl)cyclobutane is as follows:Into a clean, dry reactor equipped with a stirrer and under nitrogen are successively loaded 5.4 kg of DMF (5.1 eqV) and then 4.53 kg of triphenylphosphite. 2.34 kg of bromine is then introduced while maintaining the temperature at less than 12°C. The stirring speed is regulated according to the fluidity of the reaction medium.10065] The set point of the jacket is then adjusted to -12°C. and then 1.120 kg of cyclobutylmethanol is introduced in such a way as not to exceed a temperature of -5° C. At the end of the addition the whole is allowed to return slowly to room temperature. After distillation and washing, the final product 2b (mass 1.529 kg) having a GC relative purity of 98.3% is obtained with a yield of 78%.

InChI:InChI=1/C5H9Br/c6-4-5-2-1-3-5/h5H,1-4H2

Upstream product

• 506-68-3 bromocyane 
• 861298-29-5 N-butyl-N-cyclobutylmethyl-aniline 
• 1120-56-5 methylidenecyclobutane 
• 4415-82-1 cyclobutanemethanol 
• 861786-97-2 N-cyclobutylmethyl-benzamide 
• 63659-30-3 cyclobutylmethyl methanesulfonate 
• 13295-53-9 cyclobutylmethyl 4-methylbenzenesulfonate 
• 7789-69-7 phosphorus pentabromide 
• 4415-83-2 cyclobutylmethylamine 
• 876918-34-2 2-(3-cyano-4-hydroxyphenyl)isonicotinic acid methyl ester 

Downstream Products

• 861298-29-5 N-butyl-N-cyclobutylmethyl-aniline 
• 21782-48-9 3-(cyclobutyl)-1-propanol 
• 26685-58-5 2-cyclobutylmethyl-8-(1,2-dimethyl-heptyl)-5,5-dimethyl-1,3,4,5-tetrahydro-2H-chromeno[4,3-c]pyridin-10-ol 
• 21314-99-8 3.4-Bis(cyclobutylmethoxy)nitrobenzol 
• 747350-61-4 Cyclobutylmethyl-(3-methoxy-3,3-diphenyl-propyl)-amine 
• 744979-18-8 Cyclobutylmethyl-(3-methoxy-2-methyl-3,3-diphenyl-propyl)-amine 
• 4426-06-6 DL-2-amino-3-cyclobutylpropanoic acid 
• 51598-35-7 9ξ-cyclobutylmethyl-7t-((S)-3-hydroxy-2-phenyl-propionyloxy)-9ξ-methyl-(1rN,2tH,4tH,5cN)-3-oxa-9-aza-tricyclo[3.3.1.0^2,4]nonanium; bromide 
• 91653-24-6 C₃₁H₃₇NO₃*C₄H₆O₆ 
• 85552-58-5 C₃₁H₃₉NO₄ 
• 85534-91-4 C₃₂H₃₉NO₃ 
• 91653-26-8 C₃₃H₄₁NO₃*C₄H₆O₆ 
• 85534-45-8 C₃₂H₄₁NO₄ 
• 85534-47-0 C₃₃H₄₃NO₄ 

Relevant articles and documents

SYNTHESIS AND STRUCTURE OF , A PLATINUM(II) COMPLEX CONTAINING THE NEW LIGAND (DI-t-BUTYL)CYCLOBUTYLMETHYLPHOSPHINE

The synthesis and spectral properties of trans-dichlorobis((di-t-butyl)cyclobutylmethylphosphine)platinum(II), , and of the new phosphine (di-t-butyl)cyclobutylmethylphosphine, , are described.The crystal structure of the Pt complex has been determined.The material crystallizes in the monoclinic system, space group C52h-P21/c, with two formula units in a cell of dimensions a 8.521(2), b 12.774(1), c 14.374(2) Angstroem, β 104.71(2) deg.A total of 5667 unique reflections were measured on a CAD4 diffractometer at 113 K.The final value of R(F) is 0.028 for those 4223 reflections having Fo2 > 3?(F2).The crystal structure consists of the packing of discrete neutral molecules of .A crystallographic center of symmetry is imposed on each molecule.Important intramolecular distances include Pt-P, 2.353(1) and Pt-Cl, 2.306(1) Angstroem.The shortest non-bonding distance between the Cl atom and a carbon atom of a t-Bu group is Cl...C(4), 3.387(3) Angstroem.No interaction between the Pt atom and the cyclobutane ring is observed.The absence of extreme steric congestion in the complex may explain the lack of such an interaction.

Rearrangement of the Grignard reagent from 1-methylcyclobutylmethyl bromide: origins of the methyl substituent effect

1-Methyl substitution leads to a small decrease (ca. 0.45) in the rate of the ring cleavage rearrangement of cyclobutylmethylmagnesium bromide.Comparison with literature data for 3- and 5-membered rings indicates that the methyl substituent shifts the equilibrium in the direction of ring cleavage, mostly by stabilization of the double bond of the open isomer, and possibly partly by destabilization of the organometallic function of the cyclic isomer.The reaction rate is decreased in both directions, probably because of increased transition state steric repulsions.

Synthesis method of analgesic intermediate bromomethyl cyclobutane

The invention relates to a synthesis method of analgesic intermediate bromomethyl cyclobutane. The synthesis method comprises the following steps: by taking ethylene and acrylic acid as starting materials, carrying out Diels-Alder reaction to obtain cyclobutanecarboxylic acid, then reducing to obtain cyclobutanemethanol, and then brominating to obtain high-purity bromomethyl cyclobutane, wherein the total yield reaches more than 65%. The synthesis method provided by the invention has the advantages of available raw materials, mild reaction conditions, simple postprocessing operation, small environmental pollution, short reaction time, high reaction operational safety, high reaction yield, good product quality and low cost, and industrial production is facilitated.

METHOD FOR PRODUCING (BROMOMETHYL)CYCLOPROPANE AND (BROMOMETHYL)CYCLOBUTANE

The present invention relates to a method for obtaining high purity (bromomethyl)cyclopropane and (bromomethyl)cyclobutane, starting respectively with cyclopropylmethanol and cyclobutylmethanol, under synthesis conditions that enable high productivity and high yield.

2-PHENYLPYRIDINE DERIVATIVE

The present invention relates to a novel 2-phenylpyridine derivative or a salt thereof, wherein the pyridine ring is substituted with a carboxyl group or the like and the benzene ring has an electron-withdrawing group such as a cyano group and an electron-donating group such as a substituted alkoxy group at the same time. Since the compound of the invention has good xanthine oxidase-inhibitory action and uric acid-lowering action and does not have a structure derived from nucleic acid, the compound has advantages of high safety and excellent effects as compared with conventional compounds and is useful as a therapeutic or preventive agent for hyperuricemia, gout, inflammatory bowel diseases, diabetic kidney diseases, diabetic retinopathy, or the like.

Piperazine derivatives

The present invention relates to compounds of formula (I) as well as pharmaceutically acceptable salts, solvates and esters thereof. These compounds can be used to prepare pharmaceutical compositions for the treatment or prevention of disorders of the central nervous system, damage to the central nervous system, cardiovascular disorders, gastrointestinal disorders, diabetes, obesity and sleep apnoea.

Triazole derivatives

The present invention relates to triazole and imidazole derivatives of formula I and to their pharmaceutically acceptable acid addition salts. These compounds are NMDA receptor subtype blockers and are useful for the treatment of diseases related to the NMDA receptor.

Indole derivatives as 5-HT1-like agonists

Compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1 is a substituted alkylene; C3 -C7 cycloalkyl optionally substituted with HO; C3 -C6 alkenyl optionally substituted with aryl; C5 -C7 cycloalkenyl; or C3 -C6 alkynyl; R2 is H; halo; F3 C; NC; R8 R9 NOC; a substituted alkylene; R8 R9 NO2 S; R10 S(O)m ; R12 CON(R11); R10 SO2 N(R11); R8 R9 NOCN(R11); R10 O2 CN(R11); R13 (CH2)n CH=CH; or R7 O are selective 5-HT1 -like receptor agonists useful in the treatment of migraine, cluster headache, chronic paroxysmal hemicrania and headache associated with vascular disorders.

Syntheses with Aliphatic Dialdehydes, XXXVIII. - Synthesis and Properties of Cycloalkylmalonaldehydes

Vilsmeier formylation of cycloalkyl-substituted enol ethers (7,14a - c,23) yields the cycloalkylmalonaldehydes 1 - 5 for the first time.In solution 1 - 5 exist in the (E)-s-(E) enol form as vinylogous carboxylic acids.The reaction of 1 - 5 with suitable electrophiles and nucleophiles leads to cycloalkyl-substituted open-chain (29,30), carbocyclic (31) as well as heterocyclic compounds (32-40) with peculiar properties due to the presence of the lipophilic cycloalkyl group.

The Ring-opening Reactions of Cyclobutylmethyl and Cyclobutenylmethyl Radicals

Rate constants for the ring-opening reactions of cyclobutylmethyl, 1-cyclobutyl-1-methylethyl, and cyclobut-2-enylmethyl radicals have been determined over a range of temperatures by kinetic e.p.r. spectroscopy.The results can be represented by equations (i) - (iii), respectively.The results are compared with those for ring log(k3/s-1) = (13.1 +/-1.4) - (49.8 +/-7.5 kJ mol-1)/2.3RT (i) log(k5/s-1) = (13.6 +/-1.6) - (58.1 +/-9.0 kJ mol1-)/2.3RT (ii) log (k10/s-1) = (12.2 +/-1.4) - (42.2 +/-8.0 kJ mol-1)/2.3RT (iii) opening of other cycloalkylmethyl radicals.The rate constants for self-reaction of n-pentyl radicals in toluene solution have also been measured over a temperature range and found to fit relation (iv). log(2kt/dm3 mol-1 s-1) = (12.3 +/-0.7) - (10.5 +/-3 kJ mol-1)/2.3RT (iv)