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diethyl benzylphosphonate

CAS No.1080-32-6
Chemical Name:diethyl benzylphosphonate
CBNumber:CB5696730
Molecular Formula:C11H17O3P
Formula Weight:228.22
MOL File:1080-32-6.mol

diethyl benzylphosphonate Property

Boiling point 106-108 °C1 mm Hg(lit.)
Density 1.095 g/mL at 25 °C(lit.)
refractive index n20/D 1.497(lit.)
Flash point >230 °F
storage temp. Sealed in dry,Room Temperature
form Liquid
Specific Gravity 1.10
color Clear colorless to slightly yellow
Water Solubility Insoluble in water.
BRN 2580931
CAS DataBase Reference 1080-32-6(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII T6D4QWT656
EPA Substance Registry System Phosphonic acid, (phenylmethyl)-, diethyl ester (1080-32-6)
UNSPSC Code 12352108
NACRES NA.22

Safety

Risk Statements :36/38-36/37/38
Safety Statements :24/25-37-26
WGK Germany :3
RTECS :SZ6600000
TSCA :Yes
HS Code :29319090

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P261-P280a-P304+P340-P305+P351+P338-P405-P501a

diethyl benzylphosphonate Price More Price(3)

Brand: Sigma-Aldrich(India)
Product number: D91071
Product name : Diethyl benzylphosphonate
Purity: 99%
Packaging: 25G
Price: ₹4773.83
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: D91071
Product name : Diethyl benzylphosphonate
Purity: 99%
Packaging: 100G
Price: ₹15349.85
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: B1795
Product name : Diethyl Benzylphosphonate
Purity: min. 98.0 %
Packaging: 25G
Price: ₹2800
Updated: 2022/05/26
Buy: Buy

diethyl benzylphosphonate Chemical Properties,Usage,Production

Chemical Properties CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID
Uses Reactant for synthesis of:
    3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders
    Natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions
    Stilbenes via on-column oxidation of vicinal diols and Horner-Emmons reactions
    Inhibitors of teh Wnt pathway for colon cancer repression using Wadsworth-Emmons reactions
    Antimalarial drug analogs against P. falciparum

Reactant for:
Cyclization of aryl ethers, amines, and amides
Investigating the effects of functional groups on the performance of clue organic LEDs
Uses Diethyl benzylphosphonate is used as a reactant for synthesis of 3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders and natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions. It is also used as reactant for cyclization of aryl ethers, amines and amides & for investigating the effects of functional groups on the performance of clue organic LEDs.
Preparation Diethyl benzylphosphonate was synthesized according to the previously published procedure [1]. Benzylphosphonic acid (1 mmol, 172 mg) and triethyl orthoacetate (30 mmol, 5.5 mL) were mixed overnight at 90 °C. The completion of the reaction was monitored by 31P NMR. After the completion of the reaction, an excess of the orthoester was evaporated under reduced pressure. The crude product was purified via a short silica gel column (hexanes/ethyl acetate). The compound 1 was isolated as a transparent oil with 98% yield (0.98 mmol, 224 mg). 1H NMR (400 MHz, DMSO-d6) δ 7.39–7.14 (m, 5H), 3.94 (dq, JH-P = 7.9, JH-H = 7.0, 4H), 3.21 (d, JH-P = 21.6 Hz, 2H), 1.16 (t, JH-H = 7.0 Hz, 6H); 13C NMR (101 MHz, DMSO-d6) δ 132.3 (d, JC-P = 9.0 Hz), 129.7 (d, JC-P = 6.6 Hz), 128.2 (d, JC-P = 3.0 Hz), 126.4 (d, JC-P = 3.4 Hz), 61.3 (d, JC-P = 6.5 Hz), 32.3 (d, JC-P = 135.1 Hz), 16.1 (d, JC-P = 5.8 Hz); 31P NMR (162 MHz, DMSO-d6) δ 26.5. The NMR data are in accordance with those reported in literature [2].
Synthesis Reference(s) Tetrahedron Letters, 29, p. 1513, 1988 DOI: 10.1016/S0040-4039(00)80339-1
Synthesis, p. 222, 1981 DOI: 10.1055/s-1981-29393
reaction suitability reaction type: C-C Bond Formation
References [1] DAMIAN TRZEPIZUR. Selective Esterification of Phosphonic Acids.[J]. Molecules, 2021. DOI:10.3390/molecules26185637.
[2] PETER J. THORNTON. Nucleoside Phosphate and Phosphonate Prodrug Clinical Candidates[J]. Journal of Medicinal Chemistry, 2016, 59 23: 10400-10410. DOI:10.1021/acs.jmedchem.6b00523.
[3] GASTON LAVEN. ChemInform Abstract: Preparation of Benzylphosphonates via a Palladium(0)-Catalyzed Cross-Coupling of H-Phosphonate Diesters with Benzyl Halides. Synthetic and Mechanistic Studies.[J]. ChemInform, 2010, 41 40. DOI:10.1002/chin.201040191.
[4] ANNA BRODZKA. The Synthesis and Evaluation of Diethyl Benzylphosphonates as Potential Antimicrobial Agents.[J]. Molecules, 2022. DOI:10.3390/molecules27206865.