15486-96-1

Basic information

• Product Name: 3-Bromopropionyl chloride
• Synonyms: B-BROMOPROPIONYL CHLORIDE;3-BROMOPROPIONYL CHLORIDE, TECH.;3-BROMOPROPIONYL CHLORIDE 99%;3-BROMOPROPIONYL CHLORIDE:SS-BROMOPROPIONYL CHLORIDE;b-Bromopropanoyl chloride;3-Bromopropionyl chloride, 95%,tech;3-Bromopropanoic acid chloride;3-Bromopropionic acid chloride
• CAS NO: 15486-96-1
• Molecular Formula: C₃H₄BrClO
• Molecular Weight: 171.42
• EINECS: 239-515-2
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 15486-96-1.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 55-57 °C17 mm Hg(lit.)
• Flash Point: 175 °F
• Appearance: Clear yellow/Liquid
• Density: 1.701 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.86mmHg at 25°C
• Refractive Index: n20/D 1.49(lit.)
• Storage Temp.: Refrigerator
• Water Solubility: REACTS
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 3-Bromopropionyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromopropionyl chloride(15486-96-1)
• EPA Substance Registry System: 3-Bromopropionyl chloride(15486-96-1)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 23-26-27-36/37/39-45-25
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 15486-96-1(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Uses

3-Bromopropionyl chloride was used in the preparation of 1-chloro-4-bromo-2-butanone.

General Description

3-Bromopropionyl chloride reacts with poly(ethylene glycol) methacrylate to yield brominated poly(ethylene glycol) methacrylate. It causes the acylation of 4-aryl-substituted 3,4-di-hydropyrimidine(1H)-2-thiones to give bicyclic pyrimido[2,1-b][1,3]thiazines.

InChI:InChI=1/C3H4BrClO/c4-2-1-3(5)6/h1-2H2

Synthetic route

3-Bromopropionic acid (590-92-1) → 3-Bromopropionyl chloride (15486-96-1)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 16h;	100%
With thionyl chloride for 8h; Inert atmosphere; Reflux;	80%
With thionyl chloride for 1h; Heating;	71%

3-Brompropionsaeure-O-trimethylsilylester (18187-28-5) → 3-Bromopropionyl chloride (15486-96-1)

Conditions	Yield
With thionyl chloride

Upstream product

• 18187-28-5 3-Brompropionsaeure-O-trimethylsilylester 
• 590-92-1 3-Bromopropionic acid 

Downstream Products

• 24839-50-7 β-bromopropionyl-homoveratrylamine 
• 99070-25-4 3-bromo-1-(4-hydroxy-3-methoxyphenyl)propan-1-one 
• 5437-82-1 3-bromo-N,N-diethylpropionylamide 
• 2439-35-2 2-(dimethylamino)ethyl methacrylate 
• 86260-02-8 4'-methylphenyl 3-bromopropionate 
• 105174-63-8 3-bromo-1-(3,4-dimethoxyphenyl)propan-1-one 
• 109840-38-2 1-acetylamino-2-[2-(acryloyl-methyl-amino)-propoxy]-benzene 
• 3580-76-5 p-Phenylenbis(3-brompropionat) 
• 99859-23-1 acetic acid-[4-(3-bromo-propionyl)-anilide] 
• 33994-09-1 β-bromoethyl-p-tolyl ketone 
• 1665-47-0 β-bromopropionic acid N-benzylamide 
• 4823-45-4 3-Brom-propionsaeure-(2-brom-aethylester) 

Relevant articles and documents

Directing spatial disposition of ferrocene around homoadenine tetrads

We report synthesis and crystallographic studies of a ferrocenyl conjugate of adenine, where the hydrogen bonding interactions promote and stabilize nucleobase homotetrad formation. The Royal Society of Chemistry.

Controlled generation of singlet oxygen by porphyrin-appended gold nanoparticles

Porphyrin-appended gold nanoparticles with different chain lengths were synthesized to examine the control over photosensitization. The efficiencies evaluated by singletoxygen generation were adjusted by the average number of porphyrins on one gold nanoparticle and the particle size regardless of the linker chain length between porphyrin site and gold core.

Lead derivatization of ethyl 6-bromo-2-((dimethylamino)methyl)-5-hydroxy-1-phenyl-1H-indole-3-carboxylate and 5-bromo-2-(thiophene-2-carboxamido) benzoic acid as FabG inhibitors targeting ESKAPE pathogens

Our previous studies on FabG have identified two compounds 5-bromo-2-(thiophene-2-carboxamido) benzoic acid (A) and ethyl 6-bromo-2-((dimethylamino)methyl)-5-hydroxy-1-phenyl-1H-indole-3-carboxylate(B) as best hits with allosteric mode of inhibition. FabG is an integral part of bacterial fatty acid biosynthetic system FAS II shown to be an essential gene in most ESKAPE Pathogens. The current work is focussed on lead expansion of these two hit molecules which ended up with forty-three analogues (twenty-nine analogues from lead compound A and fourteen compounds from lead compound B). The enzyme inhibition studies revealed that compound 15 (effective against EcFabG, AbFabG, StFabG, MtFabG1) and 19 (inhibiting EcFabG and StFabG) had potency of broad-spectrum inhibition on FabG panel.

LIPIDS FOR LIPID NANOPARTICLE DELIVERY OF ACTIVE AGENTS

Compounds are provided having the following structure: (I) or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof, wherein R1, R2, R3, R4, R5, L1, L2, L3, G1, G2, and G3 are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.

An Azo Coupling Strategy for Protein 3-Nitrotyrosine Derivatization

Herein, a strategy for the selective derivatization of 3-nitrotyrosine-containing proteins using the classic azo coupling reaction as the key step is described. This novel approach featured multiple advantages and was successfully applied to detect picomole levels of protein tyrosine nitration in biological samples.