50733-91-0

Basic information

• Product Name: 2-Bromoheptanoylchloride
• Synonyms: 2-Bromoheptanoylchloride;7-Bromoheptanoyl chloride
• CAS NO: 50733-91-0
• Molecular Formula: C₇H₁₂BrClO
• Molecular Weight: 227.52658
• Mol File: 50733-91-0.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 90 °C(Press: 0.3 Torr)
• Appearance: /
• Density: 1.372±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-Bromoheptanoylchloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromoheptanoylchloride(50733-91-0)
• EPA Substance Registry System: 2-Bromoheptanoylchloride(50733-91-0)

Safety Data

• Hazardous Substances Data: 50733-91-0(Hazardous Substances Data)

Usage

General Description

2-Bromoheptanoyl chloride is a chemical compound with the molecular formula C7H13BrOCl. It is a derivative of heptanoic acid and belongs to the class of aliphatic acyl chlorides. 2-Bromoheptanoylchloride is a colorless to light yellow liquid at room temperature and is used in organic synthesis as a reagent for the preparation of various compounds. It is primarily utilized in the pharmaceutical and agrochemical industries as a building block for the synthesis of biologically active molecules and agricultural chemicals. 2-Bromoheptanoyl chloride can react with a variety of nucleophiles to form different derivatives, making it a versatile compound in organic synthesis. However, it is a highly reactive and corrosive compound and requires careful handling and storage.

Upstream product

• 111-16-0 heptanedioic acid 
• 3710-42-7 7-hydroxyheptanoic acid 
• 29823-18-5 ethyl 7-bromoheptanoate 
• 30515-28-7 7-bromoheptanoic acid 

Downstream Products

• 129090-54-6 7-Bromo-heptanoic acid pentakis-(7-bromo-heptanoyloxy)-phenyl ester 
• 129090-58-0 7-Bromo-heptanoic acid 2,3,4,5,6-pentakis-(7-bromo-heptanoyloxy)-cyclohexyl ester 
• 93645-62-6 4-(7-Bromo-heptanoyloxy)-benzoic acid 4-methoxy-phenyl ester 
• 77470-83-8 7-bromoheptano-2',6'-xylidide 
• 65542-33-8 7-bromo-1-phenylheptan-1-one 
• 792935-73-0 7-bromo-heptanoic acid (4-phenyl-thiazol-2-yl)-amide 
• 860315-15-7 5-[6-(phenylcarbamoyl)hexyl]sulfanylpentanoic acid ethyl ester 
• 875533-60-1 5-(6-phenylcarbamoylhexane-1-sulfinyl)pentanoic acid ethyl ester 
• 875533-61-2 5-(6-phenylcarbamoylhexane-1-sulfonyl)pentanoic acid ethyl ester 
• 792933-30-3 7-bromo-heptanoic acid (4-dimethylamino-phenyl)-amide 

Relevant articles and documents

Illiberis ulmivora Graeser sex attractant and preparation method thereof

The invention provides an Illiberis ulmivora Graeser sex attractant, which comprises cis-7-dodecenoic acid-2-butyl ester and cis-9-tetradecenoic acid-2-butyl ester. The invention also provides a preparation method of the Illiberis ulmivora Graeser sex attractant, which comprises the steps of reducing pimelic acid and azelaic acid into 7-hydroxyheptanoic acid through lithium aluminum hydride, brominating the 7-hydroxyheptanoic acid, performing acylating chlorination on the 7-hydroxyheptanoic acid and thionyl chloride, esterifying the 7-hydroxyheptanoic acid and the thionyl chloride with sec-butyl alcohol to form 7-bromoheptanoic acid-2-butanol ester and 9-bromononanoic acid-2-butanol ester, preparing corresponding phosphine salt from the 7-bromoheptanoic acid-2-butanol ester and the 9-bromononanoic acid-2-butanol ester and triphenylphosphine, and then carrying out wittig reaction with n-valeraldehyde to synthesize a target compound. According to the Illiberis ulmivora Graeser sex attractant and the preparation method thereof, raw materials are easy to obtain, operation is easy and convenient, the cost is low, the product yield is high, the technological process is short, synthesis reaction conditions are mild, no danger exists, the product is easy to separate, for the stereoisomerization problem, unstable phosphorus ylide reacts with fatty aldehyde, the product is mainly cis-olefin, the yield is 90% or above, the stable phosphorus ylide reacts with fatty aldehyde, and the product is mainly trans-olefin.

Discovery of Wogonin-based PROTACs against CDK9 and capable of achieving antitumor activity

Wogonin is a natural product isolated from the Scutellaria baicalensis and has been proved to be a potent and selective inhibitor of CDK9. Using this scaffold, we designed and synthesized a series of proteolysis targeting chimeras (PROTACs) targeting CDK9 by recruiting ubiquitin E3 ligase cereblon (CRBN). For constructing diverse Wogonin-based PROTACs, a “click chemistry” approach was employed for the synthesis of CDK9-targeting PROTACs. The results of western blotting assays showed that compounds containing triazole group in the linker could selectively downregulate the intracellular CDK9 level. Among these compounds, 11c could selectively degrade CDK9 in a concentration-dependent manner. In addition, the application of the proteasome inhibitor MG132 and CRBN siRNA silencing confirmed that 11c could promote the proteasome-dependent and CRBN-dependent degradation. Consistent with the degradation of the CDK9 protein, 11c selectively inhibits proliferation of CDK9-overexpressed cancer cells. Thus, our Wogonin-based PROTAC would be an efficient probe that induces the degradation of CDK9.

Flexible analogues of WAY-267,464: Synthesis and pharmacology at the human oxytocin and vasopressin 1a receptors

A previously identified, non-peptidic oxytocin (OT) receptor agonist WAY-267,464 (1) and nine novel derivatives (3, 4a-7a, 4b-7b) were synthesised and evaluated in vitro with the aim of systematically exploring hydrogen bonding interactions and ligand flexibility. All analogues were subjected to competition radioligand binding assays at human oxytocin (OT) and arginine vasopressin 1a (V1a) receptors. Physiological activity was determined using whole cell IP1 accumulation assays. Under these conditions, WAY-267,464 had higher affinity for the V1a receptor compared to the OT receptor (8.5x more selective) with poor functional selectivity (2x selective for OT receptor agonism over V1a receptor antagonism). Methylation of the resorcinol moiety (3) reversed the OT receptor pharmacological profile, removing agonist activity and inducing antagonist activity, without altering V1a receptor pharmacology. All flexible tethered derivatives removed OT receptor affinity and activity resulting in the generation of highly selective V1a receptor ligands.