4695-31-2

Basic information

• Product Name: 2-MERCAPTOISOBUTYRIC ACID
• Synonyms: 2-MERCAPTOISOBUTYRIC ACID;2-MERCAPTO-2-METHYLPROPANOIC ACID;2-THIOISOBUTYRIC ACID;2-mercapto-2-methyl-propanoicaci;2-mercapto-2-methylpropionicacid;2-methyl-2-sulfanylpropanoic acid;2-methyl-2-sulfanyl-propanoic acid
• CAS NO: 4695-31-2
• Molecular Formula: C₄H₈O₂S
• Molecular Weight: 120.17
• EINECS: 225-159-5
• Product Categories: Metal Isotopes;Sulfur & Selenium Compounds
• Mol File: 4695-31-2.mol

Chemical Properties

• Melting Point: 59-64°C
• Boiling Point: 194.19°C (rough estimate)
• Flash Point: 83.3 °C
• Appearance: /solid
• Density: 1.143 (estimate)
• Vapor Pressure: 0.0613mmHg at 25°C
• Refractive Index: 1.4782 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• PKA: 3.73±0.10(Predicted)
• CAS DataBase Reference: 2-MERCAPTOISOBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-MERCAPTOISOBUTYRIC ACID(4695-31-2)
• EPA Substance Registry System: 2-MERCAPTOISOBUTYRIC ACID(4695-31-2)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 4695-31-2(Hazardous Substances Data)

Usage

Chemical Properties

Soft Colourless Solid

Uses

2-Mercaptoisobutyric Acid, 90% (cas# 4695-31-2) is a compound useful in organic synthesis.

InChI:InChI=1/C4H8O2S/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)

Upstream product

• 23176-03-6 3-ethyl-5,5-dimethyl-2-thioxo-thiazolidin-4-one 
• 4695-19-6 5,5-dimethyl-2-imino-4-thiazolidinone 
• 4695-30-1 2-[(1-carboxy-isopropyl)disulfanyl]-2-methylpropanoic acid 
• 23426-63-3 2-bromo-2-methylpropionic acid methyl ester 
• 17356-08-0 thiourea 
• 600-00-0 ethyl 2-bromoisobutyrate 
• 52-90-4 L-Cysteine 
• 4695-19-6 2-amino-5,5-dimethyl-thiazol-4-one 
• 133944-74-8 α-ethoxythiocarbonylmercapto-isobutyric acid 
• 2052-01-9 2-bromo-2-methylpropionic acid 

Downstream Products

• 116344-38-8 C₁₉H₁₈N₂O₂S 
• 116344-40-2 C₁₈H₁₅BrN₂O₂S 
• 30247-81-5 2-(4'-Chlorphenyldithio)-2-methylpropionsaeure 
• 33441-50-8 2-mercapto-2-methylpropionic acid ethyl ester 
• 33840-91-4 α-(2,4-dinitro-phenylsulfanyl)-isobutyric acid 
• 36038-77-4 S-benzyl-2-mercapto-2-methylpropanoic acid 
• 87123-08-8 methyl 2-mercapto-2-methylpropanoate 
• 1616360-80-5 4-(4-chloro-2-methylphenyl)-3-cyclopropyl-1,6,6-trimethyl-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one 
• 1616360-08-7 4-(2,4-dichlorophenyl)-1,3,6,6-tetramethyl-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one 
• 1438273-69-8 2-methyl-2-[(4-methyl-2-nitrophenyl)thio]propanoic acid 

Relevant articles and documents

Synthesis of a new disulfide Fmoc monomer for creating biologically susceptible linkages in peptide nucleic acid oligomers

Peptide nucleic acids (PNA) are one of many synthetic mimics of DNA and RNA that have found applications as biological probes, as nano-scaffold components, and in diagnostics. In an effort to use PNA as constructs for cellular delivery we investigated the possibility of installing a biologically susceptible disulfide bond in the backbone of a PNA oligomer. Here we report the synthesis of a new abasic Fmoc monomer containing a disulfide bond that can be incorporated into a PNA oligomer (DS-PNA) using standard solid phase peptide synthesis. The disulfide bond survives cleavage from the resin and DS-PNA forms duplexes with complementary PNA oligomers. Initial studies aimed at determining if the disulfide bond is cleavable to reducing agents while in a duplex are explored using UV thermal analysis and HPLC.

THIOL-BASED FLUORESCENT PROBE FOR REACTIVE SPECIES

Detection of nitroxyl (HNO), the transient one-electron reduced form of nitric oxide, is a significant challenge owing to its high reactivity with biological thiols (rate constants as high as 109M?1 s?1). Reported herein is a new thiol-based HNO-responsive trigger that can compete against reactive thiols for HNO. This process forms an N-hydroxysulfenamide intermediate which cyclizes to release a masked fluorophore leading to fluorescence enhancement. To ensure a rapid cyclization step, the disclosed design capitalizes on two established physical organic phenomena: the alpha-effect and the Thorpe-Ingold effect. Using this new trigger, NitroxylFluor was developed; a selective HNO-responsive fluorescent probe. Treatment of NitroxylFluor with an HNO donor results in a 16-fold turn-on. This probe also exhibits excellent selectivity over various reactive nitrogen, oxygen, and sulfur species and efficacy in the presence of thiols (e.g., glutathione in mM concentrations). Also, live cell imaging of HNO using NitroxylFluor was performed.

Preparation method of 2-mercaptoisobutyric acid

The invention relates to a preparation method of 2-mercaptoisobutyric acid, which comprises the following steps: carrying out a reaction with methyl (ethyl) 2-bromoisobutyrate with thiourea to prepareisothiourea salt, and carrying out alkaline hydrolysis and acidification to obtain the 2-mercaptoisobutyric acid. The method has the advantages of low cost, mild reaction conditions and high yield, and is suitable for industrial production.

Novel preparation method of 2-mercaptoisobutyric acid

The invention provides a novel preparation method of 2-mercaptoisobutyric acid. Raw materials used in the method comprise 2-ethyl bromoisobutyrate, thiourea, an alkali solution, a solvent, and a hydrolyzate. Compared with other synthetic methods, the method provided by the invention has the advantages of a high yield, high purity, cheap and easy-availability reagents, mild reaction conditions, a simple technological process and environmental friendliness.

NitroxylFluor: A Thiol-Based Fluorescent Probe for Live-Cell Imaging of Nitroxyl

Detection of nitroxyl (HNO), the transient one-electron reduced form of nitric oxide, is a significant challenge owing to its high reactivity with biological thiols (with rate constants as high as 109 M-1 s-1). To address this, we report a new thiol-based HNO-responsive trigger that can compete against reactive thiols for HNO. This process forms a common N-hydroxysulfenamide intermediate that cyclizes to release a masked fluorophore leading to fluorescence enhancement. To ensure that the cyclization step is rapid, our design capitalizes on two established physical organic phenomena; the alpha-effect and the Thorpe-Ingold effect. Using this new trigger, we developed NitroxylFluor, a selective HNO-responsive fluorescent probe. Treatment of NitroxylFluor with an HNO donor results in a 16-fold turn-on. This probe also exhibits excellent selectivity over various reactive nitrogen, oxygen, and sulfur species and efficacy in the presence of thiols (e.g., glutathione in mM concentrations). Lastly, we successfully performed live cell imaging of HNO using NitroxylFluor.

Site-specific conjugation of RAFT polymers to proteins via expressed protein ligation

Site-specific protein conjugates with RAFT polymers were synthesized using expressed protein ligation. Stable micelles were formed from both linear block copolymer and Y-shaped conjugates.

Synthesis and crystal structure of 3,3,6,6-tetramethylmorpholine-2,5-dione, and its 5-monothioxo and 2,5-dithioxo derivatives

The synthesis of 3,3-dimethylmorpholine-2,5-diones 4a was achieved conveniently via the 'direct amide cyclization' of the linear precursors of type 3, which were prepared by coupling of 2,2-dimethyl-2H-azirin-3-amines 2 with 2-hydroxyalkanoic acids 1. Thionation of 4a with Lawesson's reagent yielded the corresponding 5-thioxomorpholin-2-ones 10 and morpholine-2,5-dithiones 11, respectively, depending on the reaction conditions. The structures of 3aa, 4aa, 10a, and 11a were established by X-ray crystallography. All attempts to prepare S-containing morpholine-2,5-dione analogs or thiomorpholine-2,5-diones by cyclization of corresponding S-containing precursors were unsuccessful and led to various other products. The structures of some of them have also been established by X-ray crystallography.

Diagnostic radiopharmaceutical compounds (That)

Tetradentate ligands are used to form neutral 99m-technetium complexes which may be useful as radiopharmaceuticals e.g. as brain imaging agents. The ligands have the structure STR1 where n is 2 or 3, m is 0-4, R is H or substituted or unsubstituted C1 -C6 alkyl, provided that one CR2 group adjacent the starred nitrogen atom represents CO and forms with the adjacent N atom, a --CONH-- amide group, Y is unsubstituted or substituted C1 -C6 alkyl, and one of X and X' represents H or a labile thiol protecting group while the other is unsubstituted or substituted C1 -C6 alkyl, alkenyl or alkynyl.

A facile, high-yielding method for the conversion of halides to mercaptans

An efficient, high-yield, one-pot preparation of alkyl and activated aryl mercaptans is presented. The method relies on sodium thiophosphate displacement of the halide, followed by mild hydrolysis of the intermediate phosphorothioate.

Organotin-containing composition for the stabilization of polymers of vinyl chloride

An organotin-containing composition for the stabilization of polymers or copolymers of vinyl chloride in which there is incorporated a stabilizing amount of an organotin compound containing at least two tin atoms and which is a mercapto, hydroxy or alkoxy substituted ester of a mercapto acid substituted organotin mercapto acid diester.