29921-57-1

Basic information

• Product Name: Isopropyl bromoacetate
• Synonyms: ISOPROPYL BROMOACETATE;Bromoacetic acid，isopropyl ester;Bromoacetic acid 1-methylethyl ester;Isopropyl bromoacetate,98%;isopropyl 2-broMoacetate;Isopropyl broMoacetate 99%;Acetic acid, bromo-, 1-methylethyl ester;bromo-aceticaci1-methylethylester
• CAS NO: 29921-57-1
• Molecular Formula: C₅H₉BrO₂
• Molecular Weight: 181.03
• EINECS: 249-956-2
• Product Categories: API intermediates;C2 to C5;Carbonyl Compounds;Esters;Building Blocks;C2 to C5;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 29921-57-1.mol

Chemical Properties

• Boiling Point: 65 °C (15 mmHg)
• Flash Point: 113 °C
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.399 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.21mmHg at 25°C
• Refractive Index: 1.444-1.446
• CAS DataBase Reference: Isopropyl bromoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropyl bromoacetate(29921-57-1)
• EPA Substance Registry System: Isopropyl bromoacetate(29921-57-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 37/39-26-45-36/37/39
• RIDADR: 1760
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 29921-57-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Isopropyl bromoacetate is used as a synthetic intermediate for the production of biaryl sulphonamide derivatives, which are important compounds in the development of pharmaceuticals. These derivatives have potential applications in the treatment of various diseases and disorders.
Used in Chemical Synthesis:
Isopropyl bromoacetate is used as a key component in the synthesis of Triisopropylphosphonoacetate and Isopropyl 2-(bis(2,2,2-trifluoroethyl) phosphoryl) acetate. These compounds are valuable in the development of new chemical products and materials, with potential applications in various industries such as agriculture, pharmaceuticals, and materials science.

InChI:InChI=1/C5H9BrO2/c1-4(2)8-5(7)3-6/h4H,3H2,1-2H3

Upstream product

• 79-08-3 bromoacetic acid 
• 67-63-0 isopropyl alcohol 
• 358-98-5 1,2-dibromo-1-fluoro-ethene 
• 683-60-3 sodium isopropylate 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 108974-39-6 3-cyano-3,4-diphenyl-butyric acid 
• 33925-44-9 β-cyano-β,β-diphenylpropionic acid 
• 22548-98-7 β-Cyan-β-phenyl-propionsaeure-isopropylester 
• 22500-01-2 β-Cyan-β-phenyl-glutarsaeure-diisopropylester 
• 63787-19-9 iso-propyl 4-acetylphenoxyacetate 
• 22180-08-1 3-Phenyl-3-cyan-buttersaeureisopropylester 
• 157071-49-3 Isopropyl 1-pyrrolylacetate 
• 108-21-4 Isopropyl acetate 
• 122236-64-0 (E)-Undec-3-enoic acid isopropyl ester 
• 122236-65-1 (Z)-4-Bromo-undec-3-enoic acid isopropyl ester 
• 87921-95-7 4-(2-Isopropoxycarbonylmethoxy-3-methoxy-phenyl)-nicotinic acid tert-butyl ester 
• 79-08-3 bromoacetic acid 
• 67-63-0 isopropyl alcohol 
• 67-64-1 acetone 

Relevant articles and documents

Cross coupling of sulfonyl radicals with silver-based carbenes: A simple approach to β-carbonyl arylsulfones

A coupling reaction between sulfonyl radicals and silver-based carbenes has been well established. This simple radical-carbene coupling (RCC) process provided an efficient approach to a variety of β-carbonyl arylsulfones from sodium arylsulfinates and diazo compounds, and was characterized by wide substrate scope, easy scale-up, simple manipulation, accessible starting materials, and mild reaction conditions.

Selective Functionalization of Aliphatic Amines via Myoglobin-Catalyzed Carbene N-H Insertion

Engineered myoglobins have recently gained attention for their ability to catalyze a variety of abiological carbene transfer reactions including the functionalization of amines via carbene insertion into N-H bonds. However, the scope of myoglobin and other hemoprotein-based biocatalysts in the context of this transformation has been largely limited to aniline derivatives as the amine substrates and ethyl diazoacetate as the carbene donor reagent. In this report, we describe the development of an engineered myoglobin-based catalyst that is useful for promoting carbene N-H insertion reactions across a broad range of substituted benzylamines and α-diazo acetates with high efficiency (82-99percent conversion), elevated catalytic turnovers (up to 7,000), and excellent chemoselectivity for the desired single insertion product (up to 99percent). The scope of this transformation could be extended to cyclic aliphatic amines. These studies expand the biocatalytic toolbox available for the selective formation of C-N bonds, which are ubiquitous in many natural and synthetic bioactive compounds.

A General Catalytic Route to Enantioenriched Isoindolinones and Phthalides: Application in the Synthesis of (S)-PD 172938

Chiral Br?nsted acid catalyzed enantioselective syntheses of isoindolinones and phthalides have been accomplished via tandem Mannich-lactamization and aldol-lactonization reactions, respectively. A variety of enantioenriched isoindolinones (up to 99% ee) and phthalides (up to 85% ee) containing α-diazoesters were afforded in excellent yields. Furthermore, a concise synthesis of (S)-PD 172938 has been demonstrated by using this protocol.

A General Catalytic Route to Enantioenriched Isoindolinones and Phthalides: Application in the Synthesis of (S)-PD 172938

Chiral Br?nsted acid catalyzed enantioselective syntheses of isoindolinones and phthalides have been accomplished via tandem Mannich-lactamization and aldol-lactonization reactions, respectively. A variety of enantioenriched isoindolinones (up to 99% ee) and phthalides (up to 85% ee) containing α-diazoesters were afforded in excellent yields. Furthermore, a concise synthesis of (S)-PD 172938 has been demonstrated by using this protocol.

Interception of Secondary Amide Ylide with Sulfonamides: Catalyst-Controlled Synthesis of N-Sulfonylamidine Derivatives

A novel, secondary amide activation strategy has been developed through the in situ generation of ylides from amides and diazoacetates. Under the developed reaction conditions, Mn-catalyzed ylide formation and interception reaction by sulfonamide delivered a variety of N-sulfonylamidines. Notably, when highly active Zn(OTf)2 was used as the catalyst, further N-H insertion products were obtained. In contrast with traditional methods, our amide activation strategy is distinguished by accessible starting material, inexpensive catalyst, and broad substrate scope.

In situ generation of nitrile oxides from copper carbene and tert -butyl nitrite: Synthesis of fully substituted isoxazoles

Herein, we present a novel [3 + 2] cycloaddition reaction of β-keto esters with nitrile oxides, which were generated in situ from copper carbene and tert-butyl nitrite. This three-component reaction provides new methodology for the direct synthesis of fully substituted isoxazole derivatives, featuring mild reaction conditions, readily accessible starting materials and simple operation. The experimental studies and DFT calculations suggest that the reaction starts with the generation of the key intermediate nitrile oxides, followed by a [3 + 2] cycloaddition reaction of β-keto esters to give the final isoxazole products.

In Situ Generation of Oxazole Ylide and Interception with Sulfonamide: Construction of Amidines Using Two Diazo Molecules

A novel generation of oxazole ylide and interception with sulfonamide have been well developed to construct fully substituted amidines. This copper-catalyzed four-component reaction incorporates two diazo molecules to target amidines and shows broad substrate scope, excellent functional groups tolerance and good to excellent yields.

Interception of Radicals by Molecular Oxygen and Diazo Compounds: Direct Synthesis of Oxalate Esters Using Visible-Light Catalysis

The synthesis of oxalate esters through a radical process, rather than the traditional ionic reaction, has been well developed in which the radicals induced by visible light are trapped by molecular oxygen and diazo compounds under room temperature. This reaction is operationally simple, mild, and shows broad substrate scopes in α-bromo ketones and diazo compounds.

Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons

A novel and efficient method for the synthesis of highly substituted benzobicyclo[2.2.2]octane skeletons has been explored. Under UV-light irradiation, o-divinylbenzenes underwent a pericyclic reaction to form the cyclic o-quinodimethane intermediates which were subsequently reacted with olefins through [4+2] addition to construct the benzobicyclo[2.2.2]octane skeletons in mild conditions. Gram scale reactions demonstrated the synthetic potential application of this protocol.

Regio- and Stereoselective Copper(II)-Catalyzed Hydrosilylation of Activated Allenes in Water: Access to Vinylsilanes

By using catalytic amounts of copper(II), 4-picoline, and dimethylphenylsilylpinacol borane, a series of allenoates were silylated on the β carbon in good to excellent yields and high (E)-selectivity. The mild and efficient silylation method is conducted in water under atmospheric conditions to afford vinylsilanes.