22118-12-3

Basic information

• Product Name: 2-bromobutyryl chloride
• Synonyms: 2-Bromobutanoic acid chloride;2-Bromobutanoyl chloride;2-Bromobutyryl chloride;Einecs 244-791-2;Butanoyl chloride,2-bromo-
• CAS NO: 22118-12-3
• Molecular Formula: C₄H₆BrClO
• Molecular Weight: 185.45
• EINECS: 244-791-2
• Mol File: 22118-12-3.mol

Chemical Properties

• Boiling Point: 65°C/40mmHg(lit.)
• Flash Point: 48.8 °C
• Appearance: /
• Density: 1.5320
• Vapor Pressure: 3.74mmHg at 25°C
• Refractive Index: 1.4740-1.4780
• CAS DataBase Reference: 2-bromobutyryl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromobutyryl chloride(22118-12-3)
• EPA Substance Registry System: 2-bromobutyryl chloride(22118-12-3)

Safety Data

• RIDADR: 2920
• HazardClass: 8/3
• PackingGroup: II
• Hazardous Substances Data: 22118-12-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Bromobutyryl chloride is used as an acylating agent for the synthesis of various organic compounds. Its reactivity allows it to form amide and ester linkages, which are essential in the construction of complex molecules and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-bromobutyryl chloride is used as a key intermediate in the synthesis of drugs. Its ability to form stable acyl linkages makes it a valuable component in the development of new therapeutic agents.
Used in Chemical Research:
2-Bromobutyryl chloride is also utilized in academic and industrial research settings for the investigation of reaction mechanisms and the development of new synthetic methodologies. Its versatility as an acylating agent enables chemists to explore a wide range of chemical transformations and applications.

InChI:InChI=1/C4H6BrClO/c1-2-3(5)4(6)7/h3H,2H2,1H3

Upstream product

• 141-75-3 butyryl chloride 
• 107-92-6 butyric acid 
• 80-58-0 2-Bromobutyric acid 

Downstream Products

• 54261-07-3 2-bromo-1-(piperidin-1-yl)butan-1-one 
• 36717-59-6 5-ethyl-furan-2,4-dione 
• 5398-24-3 2-bromobutyramide 
• 116496-46-9 2-bromo-N-methyl-N-phenylbutanamide 
• 3196-15-4 Methyl 2-bromobutyrate 
• 90869-07-1 2-(2-bromo-butyrylamino)-phenol 
• 93623-82-6 1,4-Bis-(benzhydrylidene-amino)-3,6-diethyl-piperazine-2,5-dione 
• 877-35-0 2-bromo-1-phenylbutan-1-one 
• 143669-02-7 2-Bromo-1-((S)-2,2-dimethyl-4-phenyl-oxazolidin-3-yl)-butan-1-one 
• 53301-24-9 1-(2-bromobutirril)-2-benzilcarbamil-5-etossicarbonilpirrolidina 
• 104223-98-5 2-phenyl-4-hydroxy-5-ethylthiazole 
• 53984-81-9 2-bromo-N-(2,6-dimethyl-phenyl)-butyramide 
• 42276-56-2 2-bromo-butyric acid-(2,4,6-trimethyl-anilide) 
• 42115-51-5 2-bromobutyric acid benzyl ester 

Relevant articles and documents

Inhibition of inflammatory pain and cough by a novel charged sodium channel blocker

Background and Purpose: Many pain-triggering nociceptor neurons express TRPV1 or TRPA1, cation-selective channels with large pores that enable permeation of QX-314, a cationic analogue of lidocaine. Co-application of QX-314 with TRPV1 or TRPA1 activators can silence nociceptors. In this study, we describe BW-031, a novel more potent cationic sodium channel inhibitor, and test whether its application alone can inhibit pain associated with tissue inflammation and whether this strategy can also inhibit cough. Experimental Approach: We tested the ability of BW-031 to inhibit pain in three models of tissue inflammation:- inflammation in rat paws produced by complete Freund's adjuvant or by surgical incision and a mouse ultraviolet (UV) burn model. We tested the ability of BW-031 to inhibit cough induced by inhalation of dilute citric acid in guinea pigs. Key Results: BW-031 inhibited Nav1.7 and Nav1.1 channels with approximately sixfold greater potency than QX-314 when introduced inside cells. BW-031 inhibited inflammatory pain in all three models tested, producing more effective and longer-lasting inhibition of pain than QX-314 in the mouse UV burn model. BW-031 was effective in reducing cough counts by 78%–90% when applied intratracheally under isoflurane anaesthesia or by aerosol inhalation in guinea pigs with airway inflammation produced by ovalbumin sensitization. Conclusion and Implications: BW-031 is a novel cationic sodium channel inhibitor that can be applied locally as a single agent to inhibit inflammatory pain. BW-031 can also effectively inhibit cough in a guinea pig model of citric acid-induced cough, suggesting a new clinical approach to treating cough.

PHOSPHONIUM ION CHANNEL BLOCKERS AND METHODS FOR USE

The invention provides compounds of Formula (I), or pharmaceutically acceptable salts thereof: The compounds, compositions, methods and kits of the invention are useful for the treatment of pain, itch, and neurogenic inflammation.

ESTER SUBSTITUTED ION CHANNEL BLOCKERS AND METHODS FOR USE

The invention provides compounds of Formula (I), or pharmaceutically acceptable salts thereof. The compounds, compositions, methods and kits of the invention are useful for the treatment of pain, itch, and neurogenic inflammation.

Method and using tracer charged ion channel

The invention provides compounds, compositions, methods, and kits for the treatment of pain, itch, and neurogenic inflammation.

Transition-Metal-Free Coupling of Alkynes with α-Bromo Carbonyl Compounds: An Efficient Approach towards β,γ-Alkynoates and Allenoates

A direct transition-metal-free coupling between alkynes and α-bromo carbonyl compounds has been developed with ultraviolet (UV) light in aqueous media. This method represents a facile approach to synthetically useful β,γ-alkynyl esters and amides stereoselectively from two readily available starting materials. As an example of the synthetic application of the products, the alkynyl esters were readily converted into allenoates. Time for UV! A direct coupling between alkynes and α-bromo compounds has been developed with ultraviolet light in aqueous media (see scheme). This method represents a facile approach to synthetically useful β,γ-alkynyl esters and amides stereoselectively from two readily available starting materials.

Enantioselective synthesis of quaternary α-amino acids via l -tert-leucine-derived squaramide-catalyzed conjugate addition of α-nitrocarboxylates to enones

Enantioselective Michael addition of tertiary α-nitroesters to β-unsubstituted vinyl ketones has been carried out in the presence of an l-tert-leucine-derived squaramide as organocatalyst. The products, quaternary α-nitroesters, were formed in excellent yield and moderate to good ee's in most cases. Scale-up of the reaction and synthetic applications of the products, including transformation to representative quaternary α-amino acids, have also been demonstrated.

A fast-initiating ionically tagged ruthenium complex: A robust supported pre-catalyst for batch-process and continuous-flow olefin metathesis

In this study, a new pyridinium-tagged Ru complex was designed and anchored onto sulfonated silica, thereby forming a robust and highly active supported olefin-metathesis pre-catalyst for applications under batch and continuous-flow conditions. The involvement of an oxazine-benzylidene ligand allowed the reactivity of the formed Ru pre-catalyst to be efficiently controlled through both steric and electronic activation. The oxazine scaffold facilitated the introduction of the pyridinium tag, thereby affording the corresponding cationic pre-catalyst in good yield. Excellent activities in ring-closing (RCM), cross (CM), and enyne metathesis were observed with only 0.5mol % loading of the pre-catalyst. When this powerful pre-catalyst was immobilized onto a silica-based cationic-exchange resin, a versatile catalytically active material for batch reactions was generated that also served as fixed-bed material for flow reactors. This system could be reused at 1mol % loading to afford metathesis products in high purity with very low ruthenium contamination under batch conditions (below 5ppm). Scavenging procedures for both batch and flow processes were conducted, which led to a lowering of the ruthenium content to as little as one tenth of the original values. Tag! You're it! A pyridinium-tagged Ru complex (see figure) that was anchored to sulfonated silica formed a robust and highly active supported olefin-metathesis pre-catalyst for applications under batch and continuous-flow conditions with low ruthenium leaching.

Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β- chloroacrylamides

Treatment of a series of α-thioamides with N-chlorosuccinimide results in efficient transformation to the analogous α-thio-β- chloroacrylamides. The mechanistic pathway has been established through isolation and characterisation of intermediate compounds. The scope of the transformation has been explored - aryl and alkylthio substituents, primary, secondary and tertiary amides can be employed. In most instances, the chloroacrylamides are formed exclusively as the Z-stereoisomer; however, with tertiary propanamides or with amides derived from butanoic or pentanoic acid a mixture of E- and Z-stereoisomers is formed. The Royal Society of Chemistry.

Structure-activity relationship study to understand the estrogen receptor-dependent gene activation of aryl- and alkyl-substituted 1H-imidazoles

A series of C5-substituted 1,2,4-triaryl-1H-imidazoles was synthesized. Their gene-activating properties were determined on estrogen receptor alpha positive MCF-7 breast cancer cells, stably transfected with the plasmid ERE wtcluc (MCF-7-2a cells). The influence of 4-OH and 2-Cl substituents on the phenyl rings as well as the significance of a methyl, ethyl, or phenyl group at C5 on the estrogen receptor binding and the resulting gene activation in MCF-7-2a cells was studied. The alkyl and aryl groups at C5 of 1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 1 increased the transactivation, while chlorine atoms on the phenyl rings diminished this effect. 5-Ethyl-1,2,4-tris(4- hydroxyphenyl)-1H-imidazole 9 was identified as the most active compound. Its excellent transcriptional activity did not only depend on the C5 ethyl group, but also on the three hydroxyl groups of the phenyl rings. Compounds (11-14) with a reduced number of hydroxyl groups displayed distinctly lower gene activation.

MITOTIC KINESIN INHIBITORS

The present invention relates to dihydropyrazole compounds that are useful for treating cellular proliferative diseases, for treating disorders associated with KSP kinesin activity, and for inhibiting KSP kinesin. The invention also related to compositions which comprise these compounds, and methods of using them to treat cancer in mammals.