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Boc-β-iodo-Ala-OMe is a protected 3-iodoalanine methyl ester containing a Boc-protected amino group, a methyl ester at the carboxyl group and a reactive β-CH2I substituent.
The iodine is the defining synthetic handle. It acts as a leaving group for substitution chemistry, allowing the alanine side chain to be converted into other functionalized amino-acid intermediates.
Product Information
| Product Name | Boc-β-iodo-Ala-OMe |
| Catalog No. | AS2081 |
| CAS No. | 93267-04-0 |
| Molecular Formula | C9H16INO4 |
| Molecular Weight | 329.13 g/mol |
| Building Block Type | Boc-protected 3-iodo-L-alanine methyl ester |
| Primary Applications | Nucleophilic substitution; noncanonical amino-acid synthesis; sulfur/nitrogen functionalization; protected intermediate chemistry |
A Useful Stereochemical Naming Detail
Public records describe CAS 93267-04-0 as N-Boc-3-iodo-L-alanine methyl ester while systematic IUPAC descriptors can use the 2R label. These statements are not necessarily contradictory: introducing iodine changes CIP priority at the side chain, so R/S nomenclature should be checked from the actual structure rather than equated automatically with D/L notation.
Why the Iodide Is Reactive
The β-iodomethyl group is suitable for nucleophilic substitution by selected sulfur-, nitrogen- or oxygen-based nucleophiles. This makes the reagent a precursor for building new noncanonical amino-acid side chains rather than a routine final SPPS monomer.
Boc and Methyl Ester Protection
Boc protects the amino group and the methyl ester masks the carboxyl. The product therefore supports intermediate chemistry under conditions where those groups should remain unreactive. Both protecting groups must be considered before the derivative is converted into an SPPS-ready monomer.
Procurement and QC
Independent current records support CAS 93267-04-0, formula C9H16INO4 and MW 329.13 g/mol. Because the identity is stereodefined and the reagent is an organoiodine intermediate, confirm structure, assay and storage condition on the lot-specific COA.
For routes that transform this iodide into a customized amino acid, evaluate the final protection state required for peptide assembly. The resulting residue can then be incorporated through custom peptide synthesis.
Product Documents
A Safety Data Sheet (SDS / MSDS) is available for this product to support laboratory handling, storage and safety assessment.
Certificates of Analysis (COAs) are batch-specific. Please contact us to request the COA for your product, and we will provide it by email.
Frequently Asked Questions
Why can the product be described as L-alanine even when an IUPAC name uses 2R?
D/L and R/S are different naming systems; the iodine-containing side chain changes CIP priorities.
Is the carboxyl group free?
No. It is protected as a methyl ester.
What is the main synthetic use?
The β-iodide is used as a leaving group for substitution and preparation of specialized amino-acid derivatives.
Related Technical Resources
Read about noncanonical amino-acid design
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