56970-78-6

Basic information

• Product Name: 3-BROMO-2-METHYLPROPIONIC ACID
• Synonyms: 3-BROMOISOBUTYRIC ACID;3-BROMO-2-METHYLPROPIONIC ACID;2-METHYL-3-BROMOPROPIONIC ACID;Methyl-3-bromopropionicacid;3-BROMO-2-METHYL-PROPANOIC ACID;3-broMo-2-Methylbutanoate;Captopril EP IMpurity D;Captopril impurity D
• CAS NO: 56970-78-6
• Molecular Formula: C₄H₇BrO₂
• Molecular Weight: 167
• Mol File: 56970-78-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 173 °C (decomp)
• Boiling Point: 230.5°Cat760mmHg
• Flash Point: 93.2°C
• Appearance: /
• Density: 1.59
• Vapor Pressure: 1.25mmHg at 25°C
• Refractive Index: 1.4750-1.4790
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 4.09±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 3-BROMO-2-METHYLPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-2-METHYLPROPIONIC ACID(56970-78-6)
• EPA Substance Registry System: 3-BROMO-2-METHYLPROPIONIC ACID(56970-78-6)

Safety Data

• RIDADR: 3265
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 56970-78-6(Hazardous Substances Data)

Usage

Uses

3-Bromo-2-methylpropionic Acid is used in the preparation of captopril selenium analogs as antioxidants and ACE inhibitors used as antihypertensive drugs.

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

Synthetic route

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

Conditions	Yield
With bromine; acetic acid	91%
With hydrogen bromide In water at 60 - 65℃; Inert atmosphere;	87.2%
With hydrogen bromide at 20℃; for 2h;	70%

3-bromo-2-methyl-propionic acid methyl ester (20609-71-6) → 3-bromo-2-methylpropionic acid (56970-78-6)

Conditions	Yield
With bis(tri-n-butyltin)oxide In toluene at 111℃; for 48h;	60%

3-bromo-2-methylpropionic acid (56970-78-6) → 2-methyl-3-sulfanylpropanoic acid (26473-47-2)

Conditions	Yield
With copper(l) iodide; sodium hydrogensulfide; tetrabutylammomium bromide In water at 65 - 75℃; Reagent/catalyst; Solvent; Inert atmosphere;	92.6%
With sodium sulfide; water; sodium carbonate

3-bromo-2-methylpropionic acid (56970-78-6) + 4-amino-2-trifluoromethylbenzonitrile (654-70-6) → 3-bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methylpropanamide

Conditions	Yield
With thionyl chloride; trimethylamine	91%
Stage #1: 3-bromo-2-methylpropionic acid With thionyl chloride In tetrahydrofuran for 2h; Inert atmosphere; Stage #2: 4-amino-2-trifluoromethylbenzonitrile With triethylamine In tetrahydrofuran at 50℃; for 2h; Inert atmosphere;

methanol (67-56-1) + 3-bromo-2-methylpropionic acid (56970-78-6) → 3-bromo-2-methyl-propionic acid methyl ester (20609-71-6)

Conditions	Yield
With sulfuric acid	90%

3-bromo-2-methylpropionic acid (56970-78-6) → 3-bromo-2-methylpropanoyl chloride (71271-28-8)

Conditions	Yield
With thionyl chloride for 4h; Heating;	77%
With thionyl chloride
With thionyl chloride

3-bromo-2-methylpropionic acid (56970-78-6) → 3-bromo-1,1,1-trifluoro-2-methylpropane (381-80-6)

Conditions	Yield
With sulfur tetrafluoride; water for 24h; Autoclave;	60%

3-bromo-2-methylpropionic acid (56970-78-6) → α-methyl-β-propiolactone (1823-54-7)

Conditions	Yield
With sodium hydroxide In chloroform for 2h; Cyclization;	42%

captamine (108-02-1) + 3-bromo-2-methylpropionic acid (56970-78-6) → α-methyl carboxybetaine disulfide

Conditions	Yield
Stage #1: 3-bromo-2-methylpropionic acid With sodium carbonate In ethanol; water at 1℃; for 20h; Stage #2: captamine In ethanol at 40℃; for 72h; Inert atmosphere;	26%

3-bromo-2-methylpropionic acid (56970-78-6) → <(32)S>-2-methyl-3-mercaptopropanoic acid

Conditions	Yield
With sodium hydroxide; (32)S-hydrogen sulfide at 95℃; for 3h;	14%

1-Naphthalenethiol (529-36-2) + 3-bromo-2-methylpropionic acid (56970-78-6) → β-[1]naphthylsulfanyl-isobutyric acid

Conditions	Yield
With sodium hydroxide

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

Conditions	Yield
With water
With sodium hydroxide at 20℃;
With barium dihydroxide

3-bromo-2-methylpropionic acid (56970-78-6) + mercaptoacetic acid (68-11-1) → β-carboxymethylsulfanyl-isobutyric acid (34914-38-0)

Conditions	Yield
With sodium hydroxide

3-bromo-2-methylpropionic acid (56970-78-6) + hydroquinone (123-31-9) → β-(4-methoxy-phenoxy)-isobutyric acid

Conditions	Yield
With potassium hydroxide; potassium carbonate

3-bromo-2-methylpropionic acid (56970-78-6) + 2-Naphthalenethiol (91-60-1) → 3-((naphthalen-2-yl)thio)-2-methylpropanoic acid

Conditions	Yield
With sodium hydroxide

3-bromo-2-methylpropionic acid (56970-78-6) + l-cysteine hydrochloride (52-89-1) → S-(2-D,L-carboxy-n-propyl)-L-cysteine (6852-42-2)

Conditions	Yield
With sodium hydroxide In ethanol

methanol (67-56-1) + 3-bromo-2-methylpropionic acid (56970-78-6) + naphthalen-2-ylamine (91-59-8) → 2-Methyl-3--propionsaeure-methylester (1148-94-3)

Conditions	Yield
(i) NaOnBu, nBuOH, (ii) /BRN= 1098229/, HCl; Multistep reaction;

3-bromo-2-methylpropionic acid (56970-78-6) + furan-2,3,5(4H)-trione pyridine (1:1) → poly(methacrylic acid) (79-41-4) + hydrogen bromide (10035-10-6, 12258-64-9)

3-bromo-2-methylpropionic acid (56970-78-6) + barytes → poly(methacrylic acid) (79-41-4) + hydrogen bromide (10035-10-6, 12258-64-9)

3-bromo-2-methylpropionic acid (56970-78-6) → zinc di-(2-methyl-3-bromopropionate)

Conditions	Yield
With zinc(II) oxide In water

3-bromo-2-methylpropionic acid (56970-78-6) → 3-bromo-2-methyl propan-1-ol (40145-08-2)

Conditions	Yield
Stage #1: 3-bromo-2-methylpropionic acid With dimethylsulfide borane complex In dichloromethane at -10 - 20℃; for 20h; Stage #2: With hydrogenchloride; dihydrogen peroxide In dichloromethane; water at 20℃; for 2h;	6.6 g

methyl 6-(trifluoromethyl)-1H-indole-2-carboxylate + 3-bromo-2-methylpropionic acid (56970-78-6) → C15H14F3NO4

Conditions	Yield
Stage #1: methyl 6-(trifluoromethyl)-1H-indole-2-carboxylate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 3-bromo-2-methylpropionic acid In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;

3-bromo-2-methylpropionic acid (56970-78-6) + 3-(3,5-bis(trifluoromethyl)phenyl)-1H-pyrazole → 3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-pyrazol-1-yl)-2-methylpropanoic acid

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 70℃; for 2h;	45 mg

Upstream product

• 20609-71-6 3-bromo-2-methyl-propionic acid methyl ester 
• 79-41-4 poly(methacrylic acid) 

Downstream Products

• 40145-08-2 3-bromo-2-methyl propan-1-ol 
• 79-41-4 poly(methacrylic acid) 
• 10035-10-6 hydrogen bromide 
• 6852-42-2 S-(2-D,L-carboxy-n-propyl)-L-cysteine 
• 71271-28-8 3-bromo-2-methylpropanoyl chloride 
• 26473-47-2 2-methyl-3-sulfanylpropanoic acid 

Relevant articles and documents

Study of a lipophilic captopril analogue binding to angiotensin I converting enzyme

Human ACE is a central component of the renin-angiotensin system and a major therapeutic target for cardiovascular diseases. The somatic form of the enzyme (sACE) comprises two homologous metallopeptidase domains (N and C), each bearing a zinc active site with similar but distinct substrate and inhibitor specificities. In this study, we present the biological activity of silacaptopril, a silylated analogue of captopril, and its binding affinity towards ACE. Based on the recently determined crystal structures of both the ACE domains, a series of docking calculations were carried out in order to study the structural characteristics and the binding properties of silacaptopril and its analogues with ACE.

Preparation method of 3-acetylthio-2-methylpropionic acid

The invention discloses a preparation method of 3-acetylthio-2-methyl propionic acid. The preparation method comprises the following steps: carrying out a reaction on a compound (methacrylic acid) represented by a formula I and hydrogen halide to obtain a compound represented by a formula II, carrying out a reaction on the compound represented by the formula II and sodium hydrosulfide or sodium sulfide to obtain a compound represented by a formula III, and performing an acetylation reaction to obtain a compound represented by a formula IV (3-acetylthio-2-methylpropionic acid). The process forsynthesizing the 3-acetylthio-2-methyl propionic acid has the advantages of being low in cost, easy and convenient to operate, good in yield, environmentally friendly and suitable for industrial production.

Allylsilane-interrupted homo-Nazarov cyclization and synthesis of bicyclo[3.2.1]octan-8-ones

The combination of homo-Nazarov cyclization of 2-(tert- butyldiphenylsilylmethyl)cyclopropyl vinyl ketone leading to oxyallyl cation and its subsequent [3+2] capture by allylsilane has been demonstrated as an useful strategy for the construction of functionalized bicyclo[3.2.1]octan-8-ones. The [3+2] capture proceeds exclusively in the exo mode to make the overall reaction diastereoselective. The less substituted end of the oxyallyl cation was found to react nearly two times faster than the more substituted end.