diethyl benzylphosphonate

한글명:diethyl benzylphosphonate

카스 번호1080-32-6

상품명:diethyl benzylphosphonate

CBNumberCB5696730

분자식C11H17O3P

포뮬러 무게228.22

MOL 파일1080-32-6.mol

화학적 성질

끓는 점	106-108 °C1 mm Hg(lit.)
밀도	1.095 g/mL at 25 °C(lit.)
굴절률	n20/D 1.497(lit.)
인화점	>230 °F
저장 조건	Sealed in dry,Room Temperature
물리적 상태	액체
Specific Gravity	1.10
색상	무색투명~미황색
수용성	물에 불용성.
BRN	2580931
CAS 데이터베이스	1080-32-6(CAS DataBase Reference)
EPA	Phosphonic acid, (phenylmethyl)-, diethyl ester (1080-32-6)

위험 및 안전 성명

위험 카페고리 넘버

36/38-36/37/38

안전지침서

24/25-37-26

WGK 독일

RTECS 번호

SZ6600000

TSCA

Yes

HS 번호

29319090

NFPA 704:

	1
2		0

그림문자(GHS)

diethyl benzylphosphonate 화학적 특성, 용도, 생산

화학적 성질
CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID
용도
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.
제조 방법
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
참고 문헌
[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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