Bromoacetic-13c2 acid

• CAS: 52947-00-9
• Catalog Number: ACM52947009
• Category: Main Products
• Molecular Weight: 140.97
• Molecular Formula: C₂H₃BrO₂
• Synonyms: Bromoacetic acid-13C2, Bromoacetic acid-13C2,d3, 283835_ALDRICH, AKOS015893932, I04-8674, 1215692-10-6, 52947-00-9
• IUPAC Name: 2-bromoacetic acid
• SMILES: C(C(=O)O)Br
• InChI Key: KDPAWGWELVVRCH-ZDOIIHCHSA-N
• Boiling Point: 208ºC(lit.)
• Melting Point: 47-49ºC(lit.)
• Flash Point: >230 °F
• Density: 2.003g/cm³
• Exact Mass: 139.93800
• Hazard Statements: T,C,N
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Safety Description: 26-36/37/39-45-61

Case Study

13C-Labeled Bromoacetic Acids as a Critical Synthon for Position-Specific Isotopic Labeling in Enzymology Research

Näser, Ulrike, et al. Bioorganic chemistry 33.1 (2005): 53-66.

EPR characterization of enzyme-substrate intermediates benefits from site-selective 13C labeling because hyperfine interactions with 13C nuclei can reveal electronic and geometric details of paramagnetic centres and radical intermediates. 13C-Labeled bromoacetic acids (including [1-13C]-, [2-13C]-, or [1,2-13C]-labeled bromoacetic acid) provides a convenient two-carbon labeled synthon that can be carried through classical organic transformations to place 13C labels at defined positions in γ-butyrolactone scaffolds and, after enzymatic or chemoenzymatic conversion, in 4-hydroxybutyryl-CoA isotopomers for mechanistic EPR experiments.
Synthetic Strategy: The bromoacetic-13C2 Acid was first converted into its corresponding methyl ester. This activated ester was then used in a Wittig reaction with a protected aldehyde. The beauty of this approach lies in its flexibility: by using Bromoacetic-13C2 Acid, or its singly labeled counterparts ([1-13C]- or [2-13C]-bromoacetic acid), the 13C labels could be programmed to end up in any specific carbon position (C1, C2, C3, or C4) of the final four-carbon lactone ring. This enabled the creation of a suite of substrates labeled with 13C in a single, defined location. Subsequent hydrogenation affords the saturated 4-(4-methoxybenzyloxy)butanoic methyl ester, and PMB deprotection (DDQ) triggers lactonization to give the target γ-butyrolactone, with crude labeled lactones purified by preparative gas chromatography before conversion into 4-hydroxybutyrate/CoA derivatives.

Bromoacetic-13C2 Acid as a High-Yield Precursor for Scalable Production of Stable Isotope-Labeled Building Blocks

Martinez, Rodolfo A., et al. Journal of Labelled Compounds and Radiopharmaceuticals 56.2 (2013): 31-35.

Two-carbon labeled synthons that are chemically robust, nonvolatile and amenable to downstream diversification are valuable in isotope chemistry. Commercially available 13C-bromoacetic acids are convenient entry points for preparing a family of labeled C2 building blocks; converting these into 2-(phenylthio)acetic acid derivatives produces versatile intermediates that survive handling and can be transformed into a number of labeled monomers and reagents used in synthesis and analysis.
In this work, bromoacetic-13C2 acid served as a practical, position-defined 13C precursor that can be converted in near-quantitative yield into 2-(phenylthio)acetic acid isotopomers ([1,2-13C2], [1-13C], [2-13C]) using a straightforward nucleophilic substitution with benzenethiol under mild, scalable conditions (K2CO3, acetone), enabling rapid access to stable, nonvolatile two-carbon labeled building blocks.
Synthesis Method: Bromoacetic-13C2 Acid was directly reacted with benzenethiol in a suspension of potassium carbonate in acetone. This one-pot nucleophilic substitution replaced the bromine atom with the phenylthio group. This optimized method achieved a near-quantitative conversion yield of 99% for producing 2-(phenylthio)[1,2-13C2]acetic acid. The procedure proved equally effective for its singly labeled analogs ([1-13C] and [2-13C]), providing exceptional efficiency and preserving the valuable isotopic label.

Custom Q&A

What is the molecular formula of Bromoacetic-13c2 acid?

The molecular formula of Bromoacetic-13c2 acid is C2H3BrO2.

What is the molecular weight of Bromoacetic-13c2 acid?

The molecular weight of Bromoacetic-13c2 acid is 140.93 g/mol.

When was Bromoacetic-13c2 acid created?

Bromoacetic-13c2 acid was created on October 25, 2006.

When was Bromoacetic-13c2 acid last modified?

Bromoacetic-13c2 acid was last modified on October 21, 2023.

What is the IUPAC name of Bromoacetic-13c2 acid?

The IUPAC name of Bromoacetic-13c2 acid is 2-bromoacetic acid.

What is the InChI of Bromoacetic-13c2 acid?

The InChI of Bromoacetic-13c2 acid is InChI=1S/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5)/i1+1,2+1.

What is the InChIKey of Bromoacetic-13c2 acid?

The InChIKey of Bromoacetic-13c2 acid is KDPAWGWELVVRCH-ZDOIIHCHSA-N.

What is the canonical SMILES of Bromoacetic-13c2 acid?

The canonical SMILES of Bromoacetic-13c2 acid is C(C(=O)O)Br.

What is the CAS number of Bromoacetic-13c2 acid?

The CAS number of Bromoacetic-13c2 acid is 52947-00-9.

What is the topological polar surface area of Bromoacetic-13c2 acid?

The topological polar surface area of Bromoacetic-13c2 acid is 37.3Ų.