71271-28-8

Basic information

• Product Name: 3-bromo-2-methylpropanoyl chloride
• Synonyms: 3-Bromo-2-methylpropanoyl chloride; propanoyl chloride, 3-bromo-2-methyl-
• CAS NO: 71271-28-8
• Molecular Formula: C₄H₆BrClO
• Molecular Weight: 185.4468
• EINECS: 615-270-0
• Mol File: 71271-28-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 173.7°C at 760 mmHg
• Flash Point: 58.8°C
• Density: 1.59g/cm³
• Vapor Pressure: 1.25mmHg at 25°C
• Refractive Index: 1.48
• CAS DataBase Reference: 3-bromo-2-methylpropanoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromo-2-methylpropanoyl chloride(71271-28-8)
• EPA Substance Registry System: 3-bromo-2-methylpropanoyl chloride(71271-28-8)

Safety Data

• Hazardous Substances Data: 71271-28-8(Hazardous Substances Data)

Upstream product

• 56970-78-6 3-bromo-2-methylpropionic acid 
• 79-41-4 poly(methacrylic acid) 

Downstream Products

• 110409-98-8 N-(benzyloxy)-3-bromo-2-methylpropanamide 
• 76465-56-0 3-Bromo-2-methyl-propionic acid [1-pyren-1-yl-eth-(E)-ylidene]-hydrazide 
• 76465-57-1 3-Bromo-2-methyl-propionic acid [1-phenyl-1-pyren-1-yl-meth-(E)-ylidene]-hydrazide 
• 123337-34-8 <(2,4-dioxo-5,5-diphenyl-3-imidazolidinyl)methyl>-3-bromo-2-methylpropionate 
• 80629-35-2 1-(3-bromo-2S-methylpropionyl)-pyrrolidine-2S-carboxylic acid 
• 73800-69-8 1-(3-bromo-2-methyl-1-oxopropyl)-L-proline 
• 1390644-52-6 2-((R)-3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyi)phenyl-3-bromo-2-methyl propanoate 

Relevant articles and documents

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Synthesis, characterization and antioxidant activity of angiotensin converting enzyme inhibitors

Angiotensin converting enzyme (ACE) catalyzes the conversion of angiotensin I (Ang I) to angiotensin II (Ang II). ACE also cleaves the terminal dipeptide of vasodilating hormone bradykinin (a nonapeptide) to inactivate this hormone. Therefore, inhibition of ACE is generally used as one of the methods for the treatment of hypertension. 'Oxidative stress' is another disease state caused by an imbalance in the production of oxidants and antioxidants. A number of studies suggest that hypertension and oxidative stress are interdependent. Therefore, ACE inhibitors having antioxidant property are considered beneficial for the treatment of hypertension. As selenium compounds are known to exhibit better antioxidant behavior than their sulfur analogues, we have synthesized a number of selenium analogues of captopril, an ACE inhibitor used as an antihypertensive drug. The selenium analogues of captopril not only inhibit ACE activity but also effectively scavenge peroxynitrite, a strong oxidant found in vivo. The Royal Society of Chemistry 2011.

An improved synthesis of captopril

An improved synthesis of captopril using methacrylic acid as the starting material is described. Treatment of methacrylic acid (I) with a hydrogen halide gave the 3-halogeno-2-methylpropanoic acids II and III, which were treated with thionyl chloride to yield the corresponding 3-halogeno-2-methylpropanoyl chlorides IV and V. Treatment of IV or V with L-proline yielded the N-(R,S-3-halogeno-2-methylpropanoyl)-L-prolines VI and VII, which were separated into optically pure R- and S-diastereoisomers using dicyclohexylamine. Treatment of halides of VI or VII with methanolic ammonium hydrosulfide gave captopril in 28% yield.