18991-98-5

Basic information

• Product Name: butyl bromoacetate
• Synonyms: bromoacetic acid butyl ester;bromo-acetic acid butyl ester;4-BROMOBUTYL ACETATE 97%;2-bromoacetic acid butyl ester;butyl 2-bromoacetate;butyl 2-bromoethanoate
• CAS NO: 18991-98-5
• Molecular Formula: C₆H₁₁BrO₂
• Molecular Weight: 195.05
• EINECS: 242-729-9
• Mol File: 18991-98-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 192.7 °C at 760 mmHg
• Flash Point: 78.4 °C
• Appearance: /
• Density: 1.352g/cm³
• Vapor Pressure: 0.483mmHg at 25°C
• Refractive Index: 1.457
• CAS DataBase Reference: butyl bromoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: butyl bromoacetate(18991-98-5)
• EPA Substance Registry System: butyl bromoacetate(18991-98-5)

Safety Data

• Hazardous Substances Data: 18991-98-5(Hazardous Substances Data)

Usage

General Description

Butyl bromoacetate is a chemical compound with the formula C6H11BrO2, and it is a colorless liquid with a fruity odor. It is commonly used as a reagent in organic synthesis and is an intermediate in the production of many compounds. Butyl bromoacetate is highly flammable and can cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. It is also a potential environmental hazard due to its toxicity to aquatic organisms. The compound is used in the manufacture of pharmaceuticals, fragrances, and pesticides, as well as in research and laboratory settings. Despite its usefulness in chemical synthesis, butyl bromoacetate should be handled with caution and in accordance with proper safety protocols.

InChI:InChI=1/C6H11BrO2/c1-2-3-4-9-6(8)5-7/h2-5H2,1H3

Upstream product

• 79-08-3 bromoacetic acid 
• 71-36-3 butan-1-ol 
• 22118-09-8 2-bromoacetyl chloride 
• 2388-07-0 lithium ethoxide 
• 529-20-4 2-methylphenyl aldehyde 
• 100-52-7 benzaldehyde 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 266346-06-9 [4,7-bis-(3-nitro-benzyl)-[1,4,7]triazonan-1-yl]-acetic acid butyl ester 
• 5345-61-9 n-butyl monoiodoacetate 
• 94-80-4 Fernesta 
• 36789-40-9 N-butoxycarbonylmethyl-S-methyl-S-phenyl-sulfoximide 
• 105286-27-9 butoxycarbonylmethylenetriphenylphosphorane 
• 24761-88-4 1-butyl diazoacetate 
• 1290610-71-7 C₄₉H₇₇NO₁₃ 
• 1132647-61-0 C₂₀H₁₇Cl₄N₃O₂ 
• 1132647-65-4 C₂₀H₁₇Cl₄N₃O₂ 
• 55837-14-4 ethyl 3-phenyl-3-piperidinopropanoate 
• 266346-08-1 [4,7-bis-(3-amino-benzyl)-[1,4,7]triazonan-1-yl]-acetic acid butyl ester 
• 79131-29-6 1-Butoxycarbonylmethyl-4-[(E)-2-(2-hydroxy-phenyl)-vinyl]-pyridinium; bromide 
• 79-08-3 bromoacetic acid 
• 71-36-3 butan-1-ol 

Relevant articles and documents

Synthesis of novel oil-soluble fluorinated surfactants via Wittig-Horner reaction

In this paper, the synthesis and characterization of novel oil-soluble fluorinated surfactants were reported. Both Wittig and Wittig-Horner reaction were used for constructing the perfluorinated branch-chain structure, and the latter provided a better method through a three-step synthesis route which was easy worked up and low cost. The surface tension of novel products in toluene, n-hexane and nitromethane with concentrations of 0.1 mol/L, 0.05 mol/L, 0.025 mol/L, 0.0125 mol/L, 0.00625 mol/L and 0 mol/L were examined. The surface tension research of these surfactants showed that they can reduce the surface tension of organic reagents dramatically. For example, compound 1e can reduce the surface tension of nitromethane from 36.6 mN/m to 24.2 mN/m in the concentration of 0.1 mol/L, and the surface tension of toluene was reduced from 28.0 mN/m to 22.7 mN/m when the concentration of compound 1a was 0.1 mol/L.

Dehydrative Allylation of Alkenyl sp2C-H Bonds

We designed a cooperative catalytic system by combining commercially available Ca(NTf2)PF6 and Pd(PPh3)4 to address the dehydrative allylation of alkenyl sp2 C-H bonds in an environmentally benign manner. A novel C-OH bond cleavage method was found to be crucial for this practical protocol. A variety of alkenes and allylic alcohols equipped with wide-spectrum functional groups can be successfully incorporated into the desired cross-coupling, affording 1,4-dienes with moderate to excellent yields and high stereo- and regioselectivity.

A Tunable Route to Prepare α,β-Unsaturated Esters and α,β-Unsaturated-γ-Keto Esters through Copper-Catalyzed Coupling of Alkenyl Boronic Acids with Phosphorus Ylides

A tunable strategy to prepare α,β-unsaturated esters and α,β-unsaturated-γ-keto esters in good to excellent yields was developed through copper-catalyzed oxidative coupling of phosphorus ylides with alkenyl boronic acids under mild conditions. The reaction without water afforded α,β-unsaturated esters, ketones, and amides while α,β-unsaturated-γ-keto esters, 1,4-α,β-unsaturated diketones and α,β-unsaturated-γ-keto amides were obtained when using 5.0 equiv. of water. H2O18 labeling experiments showed that water played an important role in the formation of α,β-unsaturated-γ-keto esters. A plausible formation mechanism for α,β-unsaturated esters and α,β-unsaturated-γ-keto esters was proposed based on mechanistic studies. Phosphonium salts could also be used directly as coupling partners instead of phosphorus ylides. The reaction exhibited a broad substrate scope, good functional group tolerance, good regioselectivity, and diverse coupling products. (Figure presented.).