diethyl benzylphosphonate

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diethyl benzylphosphonate

Product Name: diethyl benzylphosphonate
CAS No.: 1080-32-6
Chemical Name: diethyl benzylphosphonate
Synonyms: BENV-006;NSC 62294;Diethylbenzylphosphonat;DIETHYL BENZOPHOSPHONATE;DIETHYLBENZYLPHOSPHORATE;DIETHYL BENZYLPHOSPHONATE;DIETHOXY BENZYLPHOSPHONATE;Diethylα-toluenephosphonate;Diethyl phosphonate, benzyl-;diethyl à-toluenephosphonate
CBNumber: CB5696730
Molecular Formula: C11H17O3P
Formula Weight: 228.22
MOL File: 1080-32-6.mol

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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)
EPA Substance Registry System: Phosphonic acid, (phenylmethyl)-, diethyl ester (1080-32-6)

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Safety

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: D91071
Product name: Diethyl benzylphosphonate
Purity: 99%
Packaging: 25g
Price: $110
Updated: 2024/03/01

Sigma-Aldrich

Product number: D91071
Product name: Diethyl benzylphosphonate
Purity: 99%
Packaging: 100g
Price: $263
Updated: 2024/03/01

TCI Chemical

Product number: B1795
Product name: Diethyl Benzylphosphonate
Purity: >98.0%(GC)
Packaging: 25g
Price: $59
Updated: 2024/03/01

Alfa Aesar

Product number: A10645
Product name: Diethyl benzylphosphonate, 99%
Packaging: 50g
Price: $98.65
Updated: 2024/03/01

Alfa Aesar

Product number: A10645
Product name: Diethyl benzylphosphonate, 99%
Packaging: 250g
Price: $430
Updated: 2024/03/01

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diethyl benzylphosphonate Chemical Properties,Usage,Production

Chemical Properties

CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

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.

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

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

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.

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View Lastest Price from diethyl benzylphosphonate manufacturers

Shanghai Joiny Pharmaceutical Co.,LTD

Product: Diethyl benzylphosphonate 1080-32-6
Price: US $0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 500kg
Release date: 2023-04-24

Shaanxi Dideu Medichem Co. Ltd

Product: Diethyl benzylphosphonate 1080-32-6
Price: US $1.00-0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 20 tons
Release date: 2020-01-16

Career Henan Chemical Co

Product: DIETHYL BENZYLPHOSPHONATE 1080-32-6
Price: US $5.00/ASSAYS
Min. Order: 1ASSAYS
Purity: 99%
Supply Ability: 1ton
Release date: 2019-08-05

1080-32-6, diethyl benzylphosphonateRelated Search:

PHENYLPHOSPHONIC ACID DIMETHYL ESTER DIETHYL PHENYLPHOSPHONATE DIETHYL 4-METHYLBENZYLPHOSPHONATE DIETHYL(DIPHENYLMETHYL) PHOSPHATE DIETHYL (4-BIPHENYLYLMETHYL)PHOSPHONATE DIETHYL(4-NITROBENZYL)PHOSPHONATE DIETHYL 4-AMINOBENZYLPHOSPHONATE DIETHYL 4-METHOXYBENZYLPHOSPHONATE diethyl benzylphosphonate DIETHYL 1-NAPHTHYLMETHYLPHOSPHONATE DIETHYL 4-CHLOROBENZYLPHOSPHONATE BENZYLPHOSPHONIC ACID DIETHYL (2-CHLORO-6-FLUOROBENZYL)PHOSPHONATE DIETHYL(PHENYLOXOMETHYL)PHOSPHONATE DIETHYL (ALPHA-AMINOBENZYL)PHOSPHONATE HYDROCHLORIDE (2-METHYLBENZYL)PHOSPHONIC ACID DIETHYL ESTER DIETHYL (2,6-DICHLOROBENZYL)PHOSPHONATE DIETHYL HYDROXY(PHENYL)METHYLPHOSPHONATE

(phenylmethyl)-phosphonicacidiethylester

benzyl-phosphonicacidiethylester

Benzylphosphonsαurediethylester

Diethoxyphosphonomethylbenzene

Diethyl phosphonate, benzyl-

DIETHYL BENZOPHOSPHONATE

Phenylmethanephosphonic acid diethyl ester

Diethylbenzylphosphonate, 99 %

Benzylphosphonic acid diethyl

NSC 62294

BENV-006

Diethyl benzylphosphonate, 99% 25GR

BENZYLPHOSPHONIC ACID DIETHYL ESTER

DIETHYL BENZYLPHOSPHONATE

DIETHOXY BENZYLPHOSPHONATE

Benzylphosphonic acid diethyl ester~Diethyl alpha-toluenephosphonate

diethyl à-toluenephosphonate

Diethylbenzylphosphonat

Diethylα-toluenephosphonate

Phenylmethanphosphonsαurediethylester

Phosphonic acid, benzyl-, diethyl ester

Phosphonicacid,(phenylmethyl)-,diethylester

BENZYLOPHOSPHONICACID,DIETHYLESTER

DIETHYLBENZYLPHOSPHORATE

Diethyl Benzylphosphonate &gt

Phosphonic acid, P-(phenylmethyl)-, diethyl ester

diethoxyphosphorylmethylbenzene

1080-32-6

C6H5CH2POOC2H52

C11H17O3P

Wittig & Horner-Emmons Reaction

Horner-Emmons Reaction

Horner-Wadsworth-Emmons Reagents

Synthetic Reagents

Olefination

C-C Bond Formation

Horner-Emmons Reaction

Synthetic Organic Chemistry

Wittig & Horner-Emmons Reaction

C-C Bond Formation

Horner-Wadsworth-Emmons Reagents

Olefination