≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C,Argon charged Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 6 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Description
Thein-vivoincorporation of clickable unnatural amino acids such as 4-Azido-L-phenylalanine with unique reactivity at a defined postition is used for functionalization of proteins. The azide functionalities in the protein can then be modified with almost any alkyne bearing molecule by Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). Copper-free alternatives with strained internal alkynes are also available (SPAAC). Some examples enabled with this technique are protein PEGylation, masking with sugars, and the attachment to antibodies.
| Pubchem Sid | 504762392 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/504762392 |
| Canonical Smiles | C1=CC(=CC=C1CC(C(=O)O)N)N=[N+]=[N-] |
| IUPAC Name | (2S)-2-amino-3-(4-azidophenyl)propanoic acid |
| InChIKey | NEMHIKRLROONTL-QMMMGPOBSA-N |
| INCHI | 1S/C9H10N4O2/c10-8(9(14)15)5-6-1-3-7(4-2-6)12-13-11/h1-4,8H,5,10H2,(H,14,15)/t8-/m0/s1 |
| Isomeric SMILES | C1=CC(=CC=C1C[C@@H](C(=O)O)N)N=[N+]=[N-] |
| Molecular Weight | 206.2 |
| Reaxy-Rn | 1821593 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1821593&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | Phenylalanine and derivatives |
| Alternative Parents | Phenylpropanoic acids Amphetamines and derivatives L-alpha-amino acids Phenylazides Aralkylamines Amino acids Azo compounds Azo imides Carboxylic acids Monocarboxylic acids and derivatives Hydrocarbon derivatives Carbonyl compounds Organic salts Organic zwitterions Organic oxides Monoalkylamines |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenylalanine or derivatives - 3-phenylpropanoic-acid - Alpha-amino acid - Amphetamine or derivatives - L-alpha-amino acid - Phenylazide - Aralkylamine - Benzenoid - Monocyclic benzene moiety - Azo compound - Azo imide - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Organooxygen compound - Organonitrogen compound - Amine - Primary aliphatic amine - Hydrocarbon derivative - Carbonyl group - Organic zwitterion - Organic salt - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Primary amine - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
| External Descriptors | Not available |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 F23251208 | Certificate of Analysis | Apr 02, 2026 | A464775 |
| F2325501 | Certificate of Analysis | Apr 02, 2026 | A464775 |
| E2512183 | Certificate of Analysis | Apr 27, 2025 | A464775 |
| E2512184 | Certificate of Analysis | Apr 27, 2025 | A464775 |
| E2512185 | Certificate of Analysis | Apr 27, 2025 | A464775 |
| B2514091 | Certificate of Analysis | Sep 19, 2024 | A464775 |
| K2414240 | Certificate of Analysis | Sep 19, 2024 | A464775 |
| K2414241 | Certificate of Analysis | Sep 19, 2024 | A464775 |
| F23251177 | Certificate of Analysis | Jun 02, 2023 | A464775 |
| F23251178 | Certificate of Analysis | Jun 02, 2023 | A464775 |
| K2411042 | Certificate of Analysis | Jun 02, 2023 | A464775 |
| Sensitivity | Air sensitive;Heat sensitive |
|---|---|
| Melt Point(°C) | 191℃ |
| Molecular Weight | 206.200 g/mol |
| XLogP3 | -0.200 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Exact Mass | 206.08 Da |
| Monoisotopic Mass | 206.08 Da |
| Topological Polar Surface Area | 77.700 Ų |
| Heavy Atom Count | 15 |
| Formal Charge | 0 |
| Complexity | 267.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Zhiyang Hu, Jinming Liang, Taogeng Su, Di Zhang, Hao Li, Xiangdong Gao, Wenbin Yao, Xiaoda Song. (2023) Minimizing the Anticodon-Recognized Loop of Methanococcus jannaschii Tyrosyl-tRNA Synthetase to Improve the Efficiency of Incorporating Noncanonical Amino Acids. Biomolecules, 13 (4): (610). [PMID:37189358] [10.3390/biom13040610] |
| 2. Shen Fangzhou, Lu Zhaoyang, Yan Kangli, Luo Kang, Pei Shuchen, Xiang Pu. (2025) Synthesis and properties of carbon quantum dots as an antimicrobial agent and detection of ciprofloxacin. Scientific Reports, 15 (1): (1-10). [PMID:40764737] [10.1038/s41598-025-14383-4] |
| 3. Mengna Chen, Yanping Li, Qinghua He, Junjie Zeng, Xiaojiang Li, Zhui Tu. (2025) Homogeneous bioluminescent immunosensor for aflatoxin B1 detection via unnatural amino acid-based site-specific labeling. FOOD CONTROL, [PMID:] [10.1016/j.foodcont.2025.111358] |
| 4. Miao Liu, Yuanyuan Yang, Zhi Li, Yumin Duan, Zikang Chen, Jiahui Chen, Xiaoxu Wu. (2025) Fabrication of multifunctional hydrophobic silica aerogels with superior thermal safety enabled by a dual flame-retardant strategy. APPLIED CLAY SCIENCE, [PMID:] [10.1016/j.clay.2025.108021] |
| 5. Lingjiao Zhang, Baiquan Liu, Xinyang Lv, Genghui Zhang, Chenglin Li, Wenjing Zhang, Yunfei Ren, Ziming Chen, Meiyu Zhang, Qifan Xue, Zhenyu Yang, Baodan Zhao, Dongfang Yang, Hang Zhou, Feng Gao, Dawei Di, Chuan Liu. (2026) Photovoltage-Driven Two-Transistor–One-Diode Perovskite Pixels for In-Cell Optical Sensing Displays. ADVANCED MATERIALS, [PMID:41738700] [10.1002/adma.202522776] |
| 6. Juying Zhou, Yelong Huang, Haitang Xu, Han Long, Jing Xiang. (2026) Fabrication of Polyacrylonitrile-Based Composite Fiber Membranes via Ultraviolet-Curing-Electrospinning Combined Technology and Their Adsorption Performance for Methylene Blue. ChemistrySelect, 11 (13): (e06769). [PMID:] [10.1002/slct.202506769] |
