Benzylphosphonic Acid - ≥98% , CAS No.6881-57-8

CAS: 6881-57-8 Cat. No.: B334162 Molecular Weight: 172.12 Beilstein Registry Number: 2519318 EC Number: 679-170-9

GRADE & PURITY ≥98%

Synonyms

A836255 | Benzylphosphonic acid | Benzyl-phosphonic acid | MFCD00039519 | benzyl-dioxido-oxo-$l^{5}-phosphane | CHEBI:183902 | phenylmethylphosphonic acid | AKOS006221427 | Phosphonic acid, (phenylmethyl)- | Phenyl-methanephosphonic acid anion | BDBM50080

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Benzylphosphonic acid is a PTP (protein tyrosine phosphatase) inhibitor. The compound has been used to synthesize redox-active molecules and has been shown to rapidly inhibit endothelium-derived COX-1 (cyclooxygenase-1) and COX-2 activity. Other PTP inhibitors include phenylarsine oxide , and sodium orthovanadate .

Specifications

Synonyms

A836255 | Benzylphosphonic acid | Benzyl-phosphonic acid | MFCD00039519 | benzyl-dioxido-oxo-$l^{5}-phosphane | CHEBI:183902 | phenylmethylphosphonic acid | AKOS006221427 | Phosphonic acid, (phenylmethyl)- | Phenyl-methanephosphonic acid anion | BDBM50080

Specifications & Purity

≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Product Properties

• pKa: pKa: 2.11
• Ki Data: tyrosine-protein phosphatase: Ki= 4.6 mM (bovine heart)

Names and Identifiers

• Pubchem Sid: 488185949
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488185949
• Canonical Smiles: C1=CC=C(C=C1)CP(=O)(O)O
• IUPAC Name: benzylphosphonic acid
• InChIKey: OGBVRMYSNSKIEF-UHFFFAOYSA-N
• INCHI: 1S/C7H9O3P/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,8,9,10)
• Isomeric SMILES: C1=CC=C(C=C1)CP(=O)(O)O
• WGK Germany: 3
• Molecular Weight: 172.12
• Beilstein: 2519318
• Reaxy-Rn: 2519318
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2519318&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Organic phosphonic acids Organopnictogen compounds Organophosphorus compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Monocyclic benzene moiety - Organophosphonic acid derivative - Organophosphonic acid - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organophosphorus compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)

Discover Target: LCK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTPRCAP Tbio Protein tyrosine phosphatase receptor type C-associated protein (32 Activities)

Discover Target: PTPRCAP

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACP3 Tchem Prostatic acid phosphatase (71 Activities)

Discover Target: ACP3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALPG Tchem Alkaline phosphatase placental-like (1197 Activities)

Discover Target: ALPG

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALPP Tbio Alkaline phosphatase placental type (103 Activities)

Discover Target: ALPP

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ENPP3 Tchem Ectonucleotide pyrophosphatase/phosphodiesterase family member 3 (241 Activities)

Discover Target: ENPP3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

Discover Target: Ptpn1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Alpl Alkaline phosphatase tissue-nonspecific (94 Activities)

Discover Target: Alpl

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

mdlA Mandelate racemase (27 Activities)

Discover Target: mdlA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO (<20 mg/ml), ethanol (>20 mg/ml), and water(warm) (20 mg/ml).
• Refractive Index: n20D1.57
• Boil Point(°C): 378.22° C at 760 mmHg
• Melt Point(°C): 165-166° C
• Molecular Weight: 172.120 g/mol
• XLogP3: -0.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 172.029 Da
• Monoisotopic Mass: 172.029 Da
• Topological Polar Surface Area: 57.500 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 157.000
• 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

References

1. Jie Li, Xi-Rong Liang, Li-Feng Zhong, Xuan-Ce Wang, Zhong-Yuan Ren, Sheng-Ling Sun, Zhao-Feng Zhang, Ji-Feng Xu.  (2013)  Measurement of the Isotopic Composition of Molybdenum in Geological Samples by MC-ICP-MS using a Novel Chromatographic Extraction Technique.  GEOSTANDARDS AND GEOANALYTICAL RESEARCH,  38  (3): (345-354).  [PMID:] [10.1111/j.1751-908X.2013.00279.x]

2. Liujiang Zhang, Meirong Fu, Xianyuan Jiang, Ziheng Zhang, Chenyue Wang, Zhenhuang Su, Bingchen He, Lin Tang, Guanhaojie Zheng, Xingyu Gao, Jianhua He.  (2025)  Benzylphosphonic Acid-Engineered Compact Self-Assembled Monolayers for Bifacial Buried Interface Passivation in High-Performance Inverted Perovskite Solar Cells.  Advanced Science,      [PMID:40995688] [10.1002/advs.202512117]

3. Yanfang Ren, Yunqi Wang, Yan Fang, Xiaohong Jiang, Meng Li, Ke Cheng, Zuliang Du.  (2025)  Robust ZnMgO Capped with Benzyl-Phosphonic Acid as Armor Layer Enables Efficient and Stable Quantum Dot Light-Emitting Diodes.  Advanced Optical Materials,      [PMID:] [10.1002/adom.202501388]

4. Na Meng, Yajing Li, Xiaorong Shi, Ziqiang Wang, Junhao Liu, Yutian Xu, Yuanhao Cui, Xinwu Ke, Xueli Li, Boya Hu, Xue Min, Kui Xu, Zhelu Hu, Lingfeng Chao, Yingdong Xia, Qingxun Guo, Yonghua Chen.  (2025)  Fully Thermal-Evaporated Perovskite Light-Emitting Diodes with Brightness Exceeding 240 000 Nits.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202510484]

5. Na Meng, Yajing Li, Yu Zhang, Junhao Liu, Ziqiang Wang, Xiaorong Shi, Yutian Xu, Yuanhao Cui, Xinwu Ke, Zhelu Hu, Lingfeng Chao, Kui Xu, Yingdong Xia, Qingxun Guo, Xue Min, Yonghua Chen.  (2025)  Boosting Efficiency of Fully Thermally Evaporated PeLEDs via Benzylphosphonic Acid-Induced In Situ Crystallization Control and Defect Passivation.  Laser & Photonics Reviews,      [PMID:] [10.1002/lpor.202502292]