42768-45-6

Basic information

• Product Name: 2-Bromovalerylchloride
• Synonyms: 2-Bromovalerylchloride
• CAS NO: 42768-45-6
• Molecular Formula: C₅H₈BrClO
• Molecular Weight: 199.47342
• Mol File: 42768-45-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 179.384 °C at 760 mmHg
• Flash Point: 62.29 °C
• Appearance: /
• Density: 1.498 g/cm³
• CAS DataBase Reference: 2-Bromovalerylchloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromovalerylchloride(42768-45-6)
• EPA Substance Registry System: 2-Bromovalerylchloride(42768-45-6)

Safety Data

• Hazardous Substances Data: 42768-45-6(Hazardous Substances Data)

Usage

General Description

2-Bromovalerylchloride, also known as alpha-Bromo-pivaloyl chloride, is a chemical compound with the molecular formula C5H8BrClO. It appears as a clear to pale yellow liquid and is used mainly in the field of organic synthesis. Due to its properties, it can react in many different types of reactions such as grignard reactions and acylations. As a reagent, it is known for its reliability and versatility in synthesizing various organic compounds. It must be handled carefully as it has corrosive properties and can cause burns and eye damage. Furthermore, it may be harmful if inhaled, ingested, or comes into contact with skin.

Upstream product

• 584-93-0 2-Bromovaleric acid 
• 638-29-9 n-valeryl chloride 
• 109-52-4 valeric acid 
• 760-78-1 2-aminopentanoic acid 

Downstream Products

• 19129-92-1 methyl 2-bromovalerate 
• 100794-28-3 2-bromo-valeric acid-(2,4,6-trimethyl-anilide) 
• 220801-73-0 2-bromo-pentanoic acid 4-formyl-phenyl ester 
• 300707-84-0 N-4'-methylphenyl-2-bromopentanamide 
• 936908-44-0 (1'S)-N-1'-phenylethyl-2-(phenylthio)pentanamide 
• 162375-42-0 N-4'-methylphenyl-2-(phenylthio)pentanamide 
• 40918-49-8 7-chloro-5-phenyl-3-propyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one 
• 479676-59-0 7-chloro-2-oxo-5-phenyl-3-propyl-2,3-dihydro-1H-1,4-benzodiazepin-4-ium-4-olate 

Relevant articles and documents

Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides

A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to α-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)-deoxyeseroline. Mechanistic investigations suggest a radical process.

Benzoxazinone-containing 3,5-dimethylisoxazole derivatives as BET bromodomain inhibitors for treatment of castration-resistant prostate cancer

The bromodomain and extra-terminal proteins (BET) have emerged as promising therapeutic targets for the treatment of castration-resistant prostate cancer (CRPC). We report the design, synthesis and evaluation of a new series of benzoxazinone-containing 3,5-dimethylisoxazole derivatives as selective BET inhibitors. One of the new compounds, (R)-12 (Y02234), binds to BRD4(1) with a Kd value of 110 nM and blocks bromodomain and acetyl lysine interactions with an IC50 value of 100 nM. It also exhibits selectivity for BET over non-BET bromodomain proteins and demonstrates reasonable anti-proliferation and colony formation inhibition effect in prostate cancer cell lines such as 22Rv1 and C4-2B. The BRD4 inhibitor (R)-12 also significantly suppresses the expression of ERG, Myc and AR target gene PSA at the mRNA level in prostate cancer cells. Treatment with (R)-12 significantly suppresses the tumor growth of prostate cancer (TGI = 70%) in a 22Rv1-derived xenograft model. These data suggest that compound (R)-12 is a promising lead compound for the development of a new class of therapeutics for the treatment of CRPC.

Enantioselective construction of tetrasubstituted stereogenic carbons through bronsted base catalyzed michael reactions: α′-hydroxy enones as key enoate equivalent

Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Bronsted base (BB) catalysis and the use of α′-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α′-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α′-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.