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analytical standard, 10 ng/μl Analytical standard for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C Ships Wet ice,FedEx DG Service 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 10 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
2-Naphthylamine is an aromatic amine used to make azo dyes. A common reason that it is used less for this purpose is that the substance is a carcinogen. Studies indicate that 2-Naphthylamine decreases the enzymatic functions of monoamine oxidase A and B. It is known that the main source of this compound is obtained from cigarette smoke. In addition, metabolites of 2-Naphthylamine such as N-hydroxy-2-Naphthylamine damages DNA by forming specific carcinogen-base adducts. These studies suggest that specific 2-Naphthylamine can cause problems for cells by binding to glycogen.
An amine compound used for research purposes
| Canonical Smiles | C1=CC=C2C=C(C=CC2=C1)N |
|---|---|
| IUPAC Name | naphthalen-2-amine |
| InChIKey | JBIJLHTVPXGSAM-UHFFFAOYSA-N |
| INCHI | 1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2 |
| Isomeric SMILES | C1=CC=C2C=C(C=CC2=C1)N |
| WGK Germany | 3 |
| RTECS | QM2100000 |
| UN Number | 1650(solid)3411(solution) |
| Packing Group | II |
| Molecular Weight | 143.19 |
| Beilstein | 3939429 |
| Reaxy-Rn | 606264 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=606264&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Naphthalenes |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Naphthalenes |
| Alternative Parents | Primary amines Organopnictogen compounds Hydrocarbon derivatives |
| Molecular Framework | Aromatic homopolycyclic compounds |
| Substituents | Naphthalene - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings. |
| External Descriptors | naphthylamine |
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| Solubility | Soluble in Ethyl Acetate and Methanol |
|---|---|
| Sensitivity | Light sensitive |
| Boil Point(°C) | 306°C |
| Melt Point(°C) | 111-113°C |
| Molecular Weight | 143.180 g/mol |
| XLogP3 | 2.300 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Exact Mass | 143.073 Da |
| Monoisotopic Mass | 143.073 Da |
| Topological Polar Surface Area | 26.000 Ų |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 133.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| 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. Qidong Yu, Wenmin Zhang, Hui Chen, Jingyi Wang, Zhiyong Wang, Qingqing Ding, Lan Zhang. (2023) Synthesis of stable and efficient amide-based covalent organic frameworks fiber coatings for the improved solid-phase microextraction of polar aromatic amines. ANALYTICA CHIMICA ACTA, [PMID:37996159] [10.1016/j.aca.2023.342002] |
| 2. Lingfeng Xu, Ying Zou, Mei Zeng, Siqi Duan, Kui Wu, Runlin Han, Limin Liu. (2021) Noninvasive Viscosity Detection in Beverages with an Aggregation-Induced Emission-Based Molecular Rotor. ACS Food Science & Technology, [PMID:] [10.1021/acsfoodscitech.1c00302] |
| 3. Qingqing Li, Wenmin Zhang, Yuheng Guo, Hui Chen, Qingqing Ding, Lan Zhang. (2021) Oxygenated carbon nanotubes cages coated solid-phase microextraction fiber for selective extraction of migrated aromatic amines from food contact materials. JOURNAL OF CHROMATOGRAPHY A, [PMID:33857834] [10.1016/j.chroma.2021.462031] |
| 4. Wang Jun, Wang Yuru, Song Lei, Wang Hua, Wang Jiaming, Li Cuiqin. (2017) Synthesis and antioxidant capacity of a C12-naphthylamine antioxidant in polyethylene. POLYMER BULLETIN, 74 (9): (3689-3705). [PMID:] [10.1007/s00289-017-1917-2] |
| 5. Xiang Han, Dong-En Wang, Sheng Chen, Longlong Zhang, Yadan Guo, Jinyi Wang. (2015) A new rhodamine-based chemosensor for turn-on fluorescent detection of Fe3+. Analytical Methods, 7 (10): (4231-4236). [PMID:] [10.1039/C5AY00568J] |
| 6. Yali Yang, Jia Chen, Xiaojing Liang, Bei Liu, Kaijun Quan, Xiuhui Liu, Hongdeng Qiu. (2024) Adjustable chromatographic performance of silica-based mixed-mode stationary phase through the control of co-grafting amounts of imidazole and C18 chain. JOURNAL OF CHROMATOGRAPHY A, [PMID:38598894] [10.1016/j.chroma.2024.464889] |
| 7. Shu-Ting Zhang, Shi-Kai Deng, Tao Li, Megan E Maloney, De-Feng Li, Jim C Spain, Ning-Yi Zhou. (2024) Discovery of the 1-naphthylamine biodegradation pathway reveals a broad-substrate-spectrum enzyme catalyzing 1-naphthylamine glutamylation. eLife, [PMID:39163210] [10.7554/eLife.95555] |
| 8. Li Yang, Bolin Yu, Jie Yuan, Rongrong Xing, Runqin Wang, Xuan Chen, Shuang Hu. (2024) Trioctylphosphine oxide-based hydrophobic magnetic deep eutectic solvent as a novel extractant for the enrichment of primary aromatic amines from juice and environmental water. TALANTA, [PMID:38823328] [10.1016/j.talanta.2024.126338] |
| 9. Jing Li, Li Xu, Zhi-guo Shi. (2018) Waxberry-like hierarchically porous ethyl-bridged hybrid silica microsphere: A substrate for enzyme catalysis and high-performance liquid chromatography. JOURNAL OF CHROMATOGRAPHY A, [PMID:30527847] [10.1016/j.chroma.2018.11.073] |
| 10. Zhima Yangcuo, Xiaodan Zheng, Yajuan Zhang, Xin Yang, Xinyi Zheng, Hang Zhu, Wenhui Chen, Qihong Cai. (2026) A new second-order derivative synchronous fluorescence spectrometry for simultaneous and rapid determination of ultratrace 1-naphthol and 2-naphthol in wastewater. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:41797160] [10.1016/j.saa.2026.127649] |
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