2848-01-3|3-(diphenylphosphino)-propanoic acid| Ambeed

CAS No. :	2848-01-3
Formula :	C₁₅H₁₅O₂P
M.W :	258.25
SMILES Code :	O=C(O)CCP(C1=CC=CC=C1)C2=CC=CC=C2
MDL No. :	MFCD00775376
InChI Key :	OTSIFUHGOBFOTH-UHFFFAOYSA-N
Pubchem ID :	3709176

Safety of [ 2848-01-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 2848-01-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 2848-01-3 ]

[ 2848-01-3 ] Synthesis Path-Downstream 1~54

1
[ 57-57-8 ]
[ 829-85-6 ]
[ 2848-01-3 ]

References: [1]Journal of Organometallic Chemistry,1994,vol. 468,p. 99 - 106.

2
[ 104890-15-5 ]
[ 2848-01-3 ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1990,vol. 47,p. 253 - 260.

3
[ 623-71-2 ]
[ 829-85-6 ]
[ 2848-01-3 ]

References: [1]Synthesis,1986,p. 198 - 208.

4
[ 79-10-7 ]
[ 829-85-6 ]
[ 2848-01-3 ]

References: [1]Journal of the American Chemical Society,1994,vol. 116,p. 4481 - 4482.

5
[ 87291-69-8 ]
[ 2848-01-3 ]
[ 118268-12-5 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 3073 - 3076.

6
[ 2848-01-3 ]
[ 109602-95-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfur; In toluene; at 85℃; for 1h;Inert atmosphere;	Ph2P(S)(CH2)2COOH (compound 4) was prepared according tothe literature method [13] by heating 200 mg (0.77 mmol) of 2with 25 mg (0.78 mmol) of sulfur to 85 C in toluene under nitrogenatmosphere for 1 h. The identity of the obtained product wasmonitored by 31P {1H} NMR spectroscopy, single crystals of 4 wereobtained by slow diffusion of hexane into a CH2Cl2 solution of 4.

References: [1]Dalton Transactions,2015,vol. 44,p. 14865 - 14876.
[2]Journal of the American Chemical Society,1994,vol. 116,p. 4481 - 4482.
[3]Polyhedron,2017,vol. 124,p. 62 - 67.

7
[ 2848-01-3 ]
[ 18991-76-9 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1992,vol. 111,p. 170 - 177.

8
[ 2916-68-9 ]
[ 2848-01-3 ]
3-diphenylphosphanyl-propanoic acid 2-trimethylsilanyl-ethyl ester [ No CAS ]

References: [1]Synlett,2003,p. 473 - 476.

9
[ 2848-01-3 ]
(R)-2-Amino-3-(diphenyl-phosphinothioyl)-propionic acid [ No CAS ]

References: [1]Journal of the American Chemical Society,1994,vol. 116,p. 4481 - 4482.

10
[ 2848-01-3 ]
(R)-2-Azido-3-(diphenyl-phosphinothioyl)-propionic acid [ No CAS ]

References: [1]Journal of the American Chemical Society,1994,vol. 116,p. 4481 - 4482.

11
[ 2848-01-3 ]
C₂₀H₂₃O₄PS [ No CAS ]

References: [1]Journal of the American Chemical Society,1994,vol. 116,p. 4481 - 4482.

12
[ 2848-01-3 ]
[ 157825-92-8 ]

References: [1]Journal of the American Chemical Society,1994,vol. 116,p. 4481 - 4482.

13
[ 2848-01-3 ]
[ 157825-94-0 ]

References: [1]Journal of the American Chemical Society,1994,vol. 116,p. 4481 - 4482.

14
[ 2848-01-3 ]
[ 157825-93-9 ]

References: [1]Journal of the American Chemical Society,1994,vol. 116,p. 4481 - 4482.

15
[ 2848-01-3 ]
(S)-3-[(S)-2-Azido-3-(diphenyl-phosphinothioyl)-propionyl]-4-benzyl-oxazolidin-2-one [ No CAS ]

References: [1]Journal of the American Chemical Society,1994,vol. 116,p. 4481 - 4482.

16
[ 128894-22-4 ]
[ 2848-01-3 ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1990,vol. 47,p. 253 - 260.

17
[ 829-85-6 ]
[ 2848-01-3 ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1990,vol. 47,p. 253 - 260.
[2]Phosphorus, Sulfur and Silicon and the Related Elements,1990,vol. 47,p. 253 - 260.
[3]Journal of the Chemical Society,1952,p. 4453,4456.

18
[ 79-37-8 ]
Ir₄(CO)11I^(1-)*N(C₂H₅)4⁽¹⁺⁾ [ No CAS ]
[ 29753-26-2 ]
[ 2848-01-3 ]
C₂H₂(CO)2NC₆H₄NHCOCH₂CH₂P(C₆H₅)2Ir₄(CO)11 [ No CAS ]

References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 641 - 643.

19
PtH(P(C₆H₅)3)(P(C₆H₅)2)2(O₂H) [ No CAS ]
[ 2848-01-3 ]
Pt(P(CH₂CH₂C(O))(C₆H₅)2)(P(C₆H₅)2)2(O₂H) [ No CAS ]

References: [1]Organometallics,1990,vol. 9,p. 1211 - 1222.

20
ammonium [⁽⁹⁹⁾Tc]pertechnate [ No CAS ]
[ 2848-01-3 ]
{⁽⁹⁹⁾Tc(P(C₆H₅)2C₂H₄COO)3} [ No CAS ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1993,p. 2901 - 2908.

21
ammonium [⁽⁹⁹⁾Tc]pertechnate [ No CAS ]
[ 2848-01-3 ]
{⁽⁹⁹⁾Tc(P(C₆H₅)2C₂H₄COO)3}*2CH₃SOCH₃ [ No CAS ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1993,p. 2901 - 2908.

22
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 2848-01-3 ]
[ 86711-96-8 ]

References: [1]Inorganic Chemistry,1983,vol. 22,p. 2895 - 2899.

23
nickel(II) nitrate hexahydrate [ No CAS ]
[ 2848-01-3 ]
[ 86711-95-7 ]

References: [1]Inorganic Chemistry,1983,vol. 22,p. 2895 - 2899.

24
ammonium hexafluorophosphate [ No CAS ]
[ 219658-32-9 ]
[ 2848-01-3 ]
[ 219658-30-7 ]

References: [1]Chemical Communications,1998,p. 2295 - 2296.

25
[(μ-(SCH2)2N(CH2CH2CH3))Fe2(CO)6] [ No CAS ]
[ 2848-01-3 ]
[((μ-SCH2)2NC3H7))(Fe(CO)3)(Fe(CO)2(Ph2PCH2CH2COOH))] [ No CAS ]

References: [1]Journal of Organometallic Chemistry,2009,vol. 694,p. 2309 - 2314.

26
[ 6066-82-6 ]
[ 2848-01-3 ]
3-(diphenylphosphaneyl)propanoic acid N-hydroxysuccinimide ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With diisopropyl-carbodiimide; In dichloromethane; at 0 - 20℃;Inert atmosphere;	3-(Diphenylphosphanyl)propanoic acid 1d (1.20 g, 4.65 mmol) was dissolved in CH2Cl2 (10 mL), and the solution was cooled to 0 C. NHS (1.05 g, 9.30 mmol) and DIC (0.86 mL, 5.58 mmol) were added, and the mixture was allowed to warm to room temperature and stirred overnight under Ar(g). The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel flash chromatography, eluting with 30% EtOAc-hexanes, to give the ester 1e as a white solid (1.64 g, 4.62 mmol, 99% yield).Data for 1e: 1H NMR (400 MHz, CDCl3) δ=7.47-7.32 (m, 10H, Ar), 2.82 (s, 4H, succinmyl), 2.67 (m, 2H, CH2), 2.43 (m, 2H, CH2). 13C NMR (100 MHz, CDCl3, 31P-coupled; 1H-decoupled, observed signals) δ=169.0, 168.5, 168.3, 137.0, 136.8, 132.8, 132.6, 129.1, 128.7, 128.7, 27.8, 27.6, 25.6, 22.7, 22.6. 31P NMR (162 MHz, CDCl3) δ=-15.3. HRMS (ESI+) m/z calculated for (C19H19NO4P)+ 356.1052, measured 356.1060.
58%	With diisopropyl-carbodiimide; In dichloromethane; at 20℃;	To a i00-rnL round-bottomed flask were added 3-(diphenyiphosphino)propanoic acid (2.50 g, 9.68 mnmol) and nhydroxysuccinimide (1.23 g, 10.7 rnmol) in DCM (19.4 ml), and then N,Nmethanediylidenebis(propan-2-amine) (1.34 g, 10.7 mmol). The mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with Et2() and the solid was removed by filtration. The filtrate was concentrated. The residue was redissoived in a mixture of EtOAc and hexane, and solid was precipitated. Filtration provided the title compound (2.00 g, 58%). m/z (ESI, ±ve ion) 356.1 (M+H).

References: [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 2359 - 2363.
Angew. Chem., Int. Ed.,2009,vol. 121,p. 2395 - 2399.
[2]Patent: US2010/125132,2010,A1 .Location in patent: Page/Page column 26-27.
[3]Journal of the American Chemical Society,2011,vol. 133,p. 8892 - 8895.
[4]Chemistry - A European Journal,2020.
[5]Dalton Transactions,2013,vol. 42,p. 1973 - 1978.
[6]Patent: WO2017/147410,2017,A1 .Location in patent: Page/Page column 1091; 1092.

27
[ 292638-85-8 ]
[ 829-85-6 ]
[ 2848-01-3 ]

Yield	Reaction Conditions	Operation in experiment
98.4%		To a 1000 ml four-necked flask, 400 g of acetonitrile was added and the temperature was lowered to T = -20 to 25 C under nitrogen. A 53.5 g diphenylphosphine, 27.5 g of methyl acrylate was put into a four-necked flask, and the alkali solution diluted with acetonitrile was added dropwise with stirring. After completion of the dropwise addition, the reaction was carried out. After the reaction was complete, the solution was hydrolyzed by adding potassium hydroxide solution, adjusted to acidic with dilute hydrochloric acid, extracted with dichloromethane, and concentrated under reduced pressureMethane, crude. The crude product is recrystallized, filtered and dried. A dry product (VI) of 73.0 g was obtained. The yield was 136.5%Rate of 98.4%.
92%		Diphenylphosphine (2.00 mL, 11.5 mmol) was dissolved in degassed CH3CN (20 mL). Methyl acrylate (3.80 mL, 42.5 mmol) and a few drops of benzyltrimethylammonium hydroxide (40 wt. % in MeOH) were added, and the resulting solution was stirred under Ar(g). The reaction was monitored by TLC and after the introduction of additional drops of base (after 2 h) the reaction was found to be complete after 4 h. The solution was then concentrated under reduced pressure; the resulting oil was dissolved in CH2Cl2 (100 mL) and concentrated again. The resulting oil was then dissolved in MeOH (10 mL) and an aqueous solution of KOH (4.00 g, 71.4 mmol in 10 mL of H2O) was added. The mixture was stirred under Ar(g). After 1 h, the reaction was found to be complete, and the solution was diluted with H2O (200 mL) and acidified to pH 2 with 2M HCl. The suspension was then extracted with CH2Cl2 (2×150 mL), and the organic layers were combined, dried over Na2SO4(s) and concentrated under reduced pressure. The solid residue was purified by silica gel flash chromatography, eluting with 2% MeOH/CH2Cl2, to give the acid 1d as a white solid (2.74 g, 10.6 mmol, 92% yield).Data for 1d: 1H NMR (400 MHz, CDCl3) δ=7.46-7.32 (10H, m, Ar), 2.44 (m, 2H, CH2), 2.35 (m, 2H, CH2). 13C NMR (100 MHz, CDCl3, 31P-coupled; 1H-decoupled, observed signals) δ=179.1, 179.0, 137.5, 137.4, 132.8, 132.6, 128.9, 128.6, 128.5, 30.5, 30.2, 22.7, 22.6. 31P NMR (162 MHz, CDCl3) δ=-15.5. HRMS (ESI+) m/z calculated for (C15H16O2P)+ 259.0888, measured 259.0895.

References: [1]Patent: CN106674281,2017,A .Location in patent: Paragraph 0024.
[2]Angewandte Chemie - International Edition,2009,vol. 48,p. 2359 - 2363.
Angew. Chem., Int. Ed.,2009,vol. 121,p. 2395 - 2399.
[3]Patent: US2010/125132,2010,A1 .Location in patent: Page/Page column 26.

28
[ 2848-01-3 ]
[ 91357-77-6 ]

References: [1]European Journal of Inorganic Chemistry,2012,p. 3441 - 3448.

29
[ 2848-01-3 ]
[PtCl(OOC(CH₂)2P(C₆H₅)2)(HOOC(CH₂)2P(C₆H₅)2)] [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,2012,p. 3441 - 3448.

30
[ 2848-01-3 ]
[ 1416224-99-1 ]

References: [1]European Journal of Inorganic Chemistry,2012,p. 3441 - 3448.

31
[ 12080-32-9 ]
[ 2848-01-3 ]
[ 1416226-90-8 ]

References: [1]European Journal of Inorganic Chemistry,2012,p. 3441 - 3448.

32
[ 590-92-1 ]
[ 829-85-6 ]
[ 2848-01-3 ]

References: [1]Dalton Transactions,2013,vol. 42,p. 1973 - 1978.

33
[ 1147124-76-2 ]
[ 2848-01-3 ]
[(trifluoroaceto)2Ru(CO)2(3-(diphenylphosphino)propionic acid)2] [ No CAS ]

References: [1]Inorganic Chemistry,2013,vol. 52,p. 10835 - 10845.

34
[ 7681-65-4 ]
[ 64-17-5 ]
[ 7732-18-5 ]
[ 2848-01-3 ]
C₆₀H₆₀Cu₄I₄O₈P₄*C₂H₆O*H₂O [ No CAS ]

References: [1]Chemical Communications,2013,vol. 49,p. 10227 - 10229.

35
[ 771-61-9 ]
[ 2848-01-3 ]
pentafluorophenyl 3-(diphenylphosphino)propanoate [ No CAS ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 14936 - 14939.

36
copper(II) choride dihydrate [ No CAS ]
[ 110871-86-8 ]
[ 2848-01-3 ]
C₃₄H₃₅CuF₂N₄O₅P*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.6%	With sodium methylate; In methanol; for 3h;pH Ca. 6.8;Reflux;	General procedure: Methanolic solution of CuCl2 2H2O (1.5 mmol) was added to a methanolic solution of 3-(diphenylphosphino)-propionic acid (L) (1.5 mmol) followed by the addition of a previously prepared methanolic solution of sparfloxacin (SFLH) (1.5 mmol) in presence of CH3ONa (1.5 mmol). The pH of the reaction mixture was adjusted to ∼6.8. The resulting solution was refluxed for 3 h on a water bath, followed by concentrating to half of its volume. A fine, green amorphous product obtained was washed with ether/hexane/chloroform and dried in vacuum desiccators. The proposed reaction for the synthesis of complexes is shown in scheme 1 . Yield: 61.6%, mp: 255 C, μeff: 1.87 BM, mol. wt. 730.20, Anal. Calc. for C34H37 F2CuN4O6P, Calc. (Found) (%): C, 55.93 (55.30); H, 5.11 (5.02); N, 7.67 (7.32); Cu, 8.70 (8.40). UV-Vis: λ (nm) (ε, M-1 cm-1): 562 (160), 380 (8850), 227 (12,560), Conductance: 20 Ω-1 cm2 mol-1.

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 136,p. 1881 - 1892.

37
copper(II) choride dihydrate [ No CAS ]
[ 85721-33-1 ]
[ 2848-01-3 ]
C₃₂H₃₁CuFN₃O₅P*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.2%	With sodium methylate; In methanol; for 3h;pH Ca. 6.8;Reflux;	General procedure: Methanolic solution of CuCl2 2H2O (1.5 mmol) was added to a methanolic solution of 3-(diphenylphosphino)-propionic acid (L) (1.5 mmol) followed by the addition of a previously prepared methanolic solution of sparfloxacin (SFLH) (1.5 mmol) in presence of CH3ONa (1.5 mmol). The pH of the reaction mixture was adjusted to ∼6.8. The resulting solution was refluxed for 3 h on a water bath, followed by concentrating to half of its volume. A fine, green amorphous product obtained was washed with ether/hexane/chloroform and dried in vacuum desiccators. The proposed reaction for the synthesis of complexes is shown in scheme 1 .

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 136,p. 1881 - 1892.

38
copper(II) choride dihydrate [ No CAS ]
[ 100986-85-4 ]
[ 2848-01-3 ]
C₃₃H₃₃CuFN₃O₆P*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54.2%	With sodium methylate; In methanol; for 3h;pH Ca. 6.8;Reflux;	General procedure: Methanolic solution of CuCl2 2H2O (1.5 mmol) was added to a methanolic solution of 3-(diphenylphosphino)-propionic acid (L) (1.5 mmol) followed by the addition of a previously prepared methanolic solution of sparfloxacin (SFLH) (1.5 mmol) in presence of CH3ONa (1.5 mmol). The pH of the reaction mixture was adjusted to ∼6.8. The resulting solution was refluxed for 3 h on a water bath, followed by concentrating to half of its volume. A fine, green amorphous product obtained was washed with ether/hexane/chloroform and dried in vacuum desiccators. The proposed reaction for the synthesis of complexes is shown in scheme 1 .

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 136,p. 1881 - 1892.

39
copper(II) choride dihydrate [ No CAS ]
gatifloxacin [ No CAS ]
[ 2848-01-3 ]
C₃₄H₃₅CuFN₃O₆P*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.8%	With sodium methylate; In methanol; for 3h;pH Ca. 6.8;Reflux;	General procedure: Methanolic solution of CuCl2 2H2O (1.5 mmol) was added to a methanolic solution of 3-(diphenylphosphino)-propionic acid (L) (1.5 mmol) followed by the addition of a previously prepared methanolic solution of sparfloxacin (SFLH) (1.5 mmol) in presence of CH3ONa (1.5 mmol). The pH of the reaction mixture was adjusted to ∼6.8. The resulting solution was refluxed for 3 h on a water bath, followed by concentrating to half of its volume. A fine, green amorphous product obtained was washed with ether/hexane/chloroform and dried in vacuum desiccators. The proposed reaction for the synthesis of complexes is shown in scheme 1 .

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 136,p. 1881 - 1892.

40
copper(II) choride dihydrate [ No CAS ]
[ 70458-92-3 ]
[ 2848-01-3 ]
C₃₂H₃₃CuFN₃O₅P*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.3%	With sodium methylate; In methanol; for 3h;pH Ca. 6.8;Reflux;	General procedure: Methanolic solution of CuCl2 2H2O (1.5 mmol) was added to a methanolic solution of 3-(diphenylphosphino)-propionic acid (L) (1.5 mmol) followed by the addition of a previously prepared methanolic solution of sparfloxacin (SFLH) (1.5 mmol) in presence of CH3ONa (1.5 mmol). The pH of the reaction mixture was adjusted to ∼6.8. The resulting solution was refluxed for 3 h on a water bath, followed by concentrating to half of its volume. A fine, green amorphous product obtained was washed with ether/hexane/chloroform and dried in vacuum desiccators. The proposed reaction for the synthesis of complexes is shown in scheme 1 .

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 136,p. 1881 - 1892.

41
copper(II) choride dihydrate [ No CAS ]
[ 82419-36-1 ]
[ 2848-01-3 ]
C₃₃H₃₃CuFN₃O₆P*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.3%	With sodium methylate; In methanol; for 3h;pH Ca. 6.8;Reflux;	General procedure: Methanolic solution of CuCl2 2H2O (1.5 mmol) was added to a methanolic solution of 3-(diphenylphosphino)-propionic acid (L) (1.5 mmol) followed by the addition of a previously prepared methanolic solution of sparfloxacin (SFLH) (1.5 mmol) in presence of CH3ONa (1.5 mmol). The pH of the reaction mixture was adjusted to ∼6.8. The resulting solution was refluxed for 3 h on a water bath, followed by concentrating to half of its volume. A fine, green amorphous product obtained was washed with ether/hexane/chloroform and dried in vacuum desiccators. The proposed reaction for the synthesis of complexes is shown in scheme 1 .

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 136,p. 1881 - 1892.

42
copper(II) choride dihydrate [ No CAS ]
[ 70458-96-7 ]
[ 2848-01-3 ]
C₃₁H₃₁CuFN₃O₅P*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.7%	With sodium methylate; In methanol; for 3h;pH Ca. 6.8;Reflux;	General procedure: Methanolic solution of CuCl2 2H2O (1.5 mmol) was added to a methanolic solution of 3-(diphenylphosphino)-propionic acid (L) (1.5 mmol) followed by the addition of a previously prepared methanolic solution of sparfloxacin (SFLH) (1.5 mmol) in presence of CH3ONa (1.5 mmol). The pH of the reaction mixture was adjusted to ∼6.8. The resulting solution was refluxed for 3 h on a water bath, followed by concentrating to half of its volume. A fine, green amorphous product obtained was washed with ether/hexane/chloroform and dried in vacuum desiccators. The proposed reaction for the synthesis of complexes is shown in scheme 1 .

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 136,p. 1881 - 1892.

43
C₅₉H₉₃N₁₀O₁₅Pol [ No CAS ]
[ 2848-01-3 ]
C₅₆H₇₅N₁₀O₁₃P [ No CAS ]

References: [1]Dalton Transactions,2015,vol. 44,p. 14865 - 14876.

44
[ 2848-01-3 ]
[ 74-88-4 ]
(2-carboxyethyl)(methyl)diphenylphosphonium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In acetonitrile;Reflux;	General procedure: A mixture of equimolar quantities of 3-(diphenylphosphonio)propanoic acid (0.01 mol) and appropriate alkyl halogenides (0.01 mol) was refluxed in dry acetonitrile (75 ml) for 1 h. Excess of solvent was removed under reduced pressure. The resulting salts 1-3, 5-8 were obtained as solid compounds, phosphonium salt 4 was obtained as yellow oil. The obtained products were washed several times with diethyl ether on a porous glass filter (besides 4) and dried under vacuum.

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,2019,vol. 194,p. 476 - 479.
[2]Russian Journal of General Chemistry,2015,vol. 85,p. 2037 - 2041.
Zh. Obshch. Khim.,2015,vol. 85,p. 1453 - 1458.

45
[ 79-10-7 ]
[ 2848-01-3 ]
[ 128894-23-5 ]

References: [1]Russian Journal of General Chemistry,2015,vol. 85,p. 2037 - 2041.
Zh. Obshch. Khim.,2015,vol. 85,p. 1453 - 1458.

46
[ 107-93-7 ]
[ 2848-01-3 ]
3-[(1-carboxypropan-2-yl)diphenylphosphonium]propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.16%	In acetonitrile; at 20℃; for 168h;	A solution of 0.17 g (0.0020 mol)of methacrylic acid was added to a solution of 0.5 g (0.0019 mol) of <strong>[2848-01-3]3-(diphenylphosphino)propionic acid</strong> in 5 mL of acetonitrile. The reaction mixture was kept at room temperature during a week. The solvent was distilled off under vacuum. The residue was washed with diethyl ether and dried on a Schott funnel. Yield 0.45 g(67.16%), colorless crystals, mp 78-79C. IR spectrum,ν, cm-1: 1620 (COO-), 1680 (COOH). 13C NMR spectrum (D2O) δC, ppm: 17.48 d (PCH2CH2, 1JPC 52.9 Hz), 19.66 d(JPC 13.6 Hz), 24.46 d (PCH, 1JPC 51 Hz), 19.66 d (CH3,2JPC 9.0 Hz), 27.25 d (CH2COOH),2JPC 3.0 Hz), 35.64(CH2COO-), 172.80 d [(), 3JPC 3.75 Hz], 179.32 d(OH, 3JPC 3.7 Hz), 175.70 d (O-, 3JPC 13.9 Hz), 116.96 (1JPC 84.2 Hz), 129.93 d. d (2JPC 12.4, 4.0 Hz), 133.05 d (3JPC 9.7 Hz), 135.05. 31P NMR spectrum(D2O): δP 25.77 ppm. Found, %: 69.48; 5.19; 7.76.C19H21O4. Calculated, %: 69.70; 5.13; 7.89.

References: [1]Russian Journal of General Chemistry,2015,vol. 85,p. 2037 - 2041.
Zh. Obshch. Khim.,2015,vol. 85,p. 1453 - 1458.
[2]Russian Journal of General Chemistry,2021,vol. 91,p. 1333 - 1341.
Zh. Obshch. Khim.,2021,vol. 91,p. 1068 - 1077.

47
[ 79-41-4 ]
[ 2848-01-3 ]
3-[(1-carboxypropan-2-yl)diphenylphosphonium]propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74.03%	In acetonitrile; at 20℃; for 168h;	A solution of 0.17 g (0.0016 mol) of crotonic acid in 3 mL of acetonitrile was added to a solution of 0.5 g (0.0019 mol) of <strong>[2848-01-3]3-(diphenylphosphino)propionic acid</strong> in 5 mL of acetonitrile. The reaction mixture was kept at room temperature during a week; the crystals were filtered off, washed with diethyl ether on a Schottfunnel, and dried under vacuum. Yield 0.496 g (74.03%), colorless crystals, mp 174-176C. IR spectrum, ν, cm-1: 1630 s (COO-), 1710 s (COOH). 13C NMR spectrum(D2O), δC, ppm: 12.5 d (3, 2JPC 2.0 Hz), 15.96 d(2,1JPC 52.0 Hz), 23.56 d (3,1JPC 72.0 Hz), 26.30 d (22, 2JPC 3.0 Hz), 27.05 d (2, 2JPC3.0 Hz), 175.3 d [(), 3JPC 17.0 Hz], 176.42 d[(),3JPC 15.0 Hz] 114.26 d (1JPC 84.0 Hz), 129.75 d(2JPC 12.0 Hz), 130.08 d (3JPC 11.0 Hz), 132.93 d (4JPC3.0 Hz). 31P NMR spectrum (D2O): δP 35.0 ppm. Found,%: 65.43; 5.34; 8.84. C19H21O4. Calculated, %: 66.28; 6.1; 9.01.

References: [1]Russian Journal of General Chemistry,2021,vol. 91,p. 1333 - 1341.
Zh. Obshch. Khim.,2021,vol. 91,p. 1068 - 1077.
[2]Russian Journal of General Chemistry,2015,vol. 85,p. 2037 - 2041.
Zh. Obshch. Khim.,2015,vol. 85,p. 1453 - 1458.

48
[ 140-10-3 ]
[ 2848-01-3 ]
3-[(2-carboxy-2-phenylethyl)diphenylphosphonium]propanoate [ No CAS ]

References: [1]Russian Journal of General Chemistry,2015,vol. 85,p. 2037 - 2041.
Zh. Obshch. Khim.,2015,vol. 85,p. 1453 - 1458.

49
oxovanadium(IV) sulfate [ No CAS ]
[ 100986-85-4 ]
[ 2848-01-3 ]
C₃₃H₃₃FN₃O₇PV [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.26%	In methanol; for 10h;pH Ca. 6.8;Reflux;	General procedure: To a hot solution of VOSO4 (2) (5 mmol) in MeOH(25.0 mL), previously prepared methanolic solution ofligand 3-(diphenylphosphino)-propionic acid (1) (5 mmol)was added, with constant stirring. Then, alkaline methanolicsolution of ciprofloxacin (5 mmol) was added. The pH of thereaction mixture was adjusted to*6.8. The resulting greensolution was refluxed for 10 h and concentrated under vacuum.Upon addition of Et2O, a green solid precipitate wasobtained, which was collected by filtration, washed withEt2O and dried in vacuo (Gajera et al., 2015). General synthesisof complexes is shown in Scheme 1. Yield: 62.61 %.M.P:[300. Anal. Calcd (%). for C32H33FN3O6PV: C, 58.54;H, 5.07; N, 6.40; V, 7.76. Found (%): C, 58.24; H, 4.76; N,6.89; V, 7.26. UV-VIS in DMSO [kmax/nm (e/M-1 cm-1)]:421 (23,729), 584 (17,100), 807 (12,391). FT-IR: tmax(cm-1) m(C=O)pyridone 1628, m(CO2)asym 1586, m(CO2)-sym 1384, m = m(CO2)asym-m(CO2)sym = 202, m(V=O)952, m(M-O) 513 cm-1. ESI-MS (m/z):654.62 [M?].

References: [1]Medicinal Chemistry Research,2016,vol. 25,p. 526 - 537.

50
oxovanadium(IV) sulfate [ No CAS ]
[ 82419-36-1 ]
[ 2848-01-3 ]
C₃₃H₃₃FN₃O₇PV [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.18%	In methanol; for 10h;pH Ca. 6.8;Reflux;	General procedure: To a hot solution of VOSO4 (2) (5 mmol) in MeOH(25.0 mL), previously prepared methanolic solution ofligand 3-(diphenylphosphino)-propionic acid (1) (5 mmol)was added, with constant stirring. Then, alkaline methanolicsolution of ciprofloxacin (5 mmol) was added. The pH of thereaction mixture was adjusted to*6.8. The resulting greensolution was refluxed for 10 h and concentrated under vacuum.Upon addition of Et2O, a green solid precipitate wasobtained, which was collected by filtration, washed withEt2O and dried in vacuo (Gajera et al., 2015). General synthesisof complexes is shown in Scheme 1. Yield: 62.61 %.M.P:[300. Anal. Calcd (%). for C32H33FN3O6PV: C, 58.54;H, 5.07; N, 6.40; V, 7.76. Found (%): C, 58.24; H, 4.76; N,6.89; V, 7.26. UV-VIS in DMSO [kmax/nm (e/M-1 cm-1)]:421 (23,729), 584 (17,100), 807 (12,391). FT-IR: tmax(cm-1) m(C=O)pyridone 1628, m(CO2)asym 1586, m(CO2)-sym 1384, m = m(CO2)asym-m(CO2)sym = 202, m(V=O)952, m(M-O) 513 cm-1. ESI-MS (m/z):654.62 [M?].

References: [1]Medicinal Chemistry Research,2016,vol. 25,p. 526 - 537.

51
oxovanadium(IV) sulfate [ No CAS ]
[ 110871-86-8 ]
[ 2848-01-3 ]
C₃₄H₃₅F₂N₄O₆PV [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.48%	In methanol; for 10h;pH Ca. 6.8;Reflux;	General procedure: To a hot solution of VOSO4 (2) (5 mmol) in MeOH(25.0 mL), previously prepared methanolic solution ofligand 3-(diphenylphosphino)-propionic acid (1) (5 mmol)was added, with constant stirring. Then, alkaline methanolicsolution of ciprofloxacin (5 mmol) was added. The pH of thereaction mixture was adjusted to*6.8. The resulting greensolution was refluxed for 10 h and concentrated under vacuum.Upon addition of Et2O, a green solid precipitate wasobtained, which was collected by filtration, washed withEt2O and dried in vacuo (Gajera et al., 2015). General synthesisof complexes is shown in Scheme 1. Yield: 62.61 %.M.P:[300. Anal. Calcd (%). for C32H33FN3O6PV: C, 58.54;H, 5.07; N, 6.40; V, 7.76. Found (%): C, 58.24; H, 4.76; N,6.89; V, 7.26. UV-VIS in DMSO [kmax/nm (e/M-1 cm-1)]:421 (23,729), 584 (17,100), 807 (12,391). FT-IR: tmax(cm-1) m(C=O)pyridone 1628, m(CO2)asym 1586, m(CO2)-sym 1384, m = m(CO2)asym-m(CO2)sym = 202, m(V=O)952, m(M-O) 513 cm-1. ESI-MS (m/z):654.62 [M?].

References: [1]Medicinal Chemistry Research,2016,vol. 25,p. 526 - 537.

52
oxovanadium(IV) sulfate [ No CAS ]
[ 70458-96-7 ]
[ 2848-01-3 ]
C₃₁H₃₁FN₃O₆PV [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.77%	In methanol; for 10h;pH Ca. 6.8;Reflux;	General procedure: To a hot solution of VOSO4 (2) (5 mmol) in MeOH(25.0 mL), previously prepared methanolic solution ofligand 3-(diphenylphosphino)-propionic acid (1) (5 mmol)was added, with constant stirring. Then, alkaline methanolicsolution of ciprofloxacin (5 mmol) was added. The pH of thereaction mixture was adjusted to*6.8. The resulting greensolution was refluxed for 10 h and concentrated under vacuum.Upon addition of Et2O, a green solid precipitate wasobtained, which was collected by filtration, washed withEt2O and dried in vacuo (Gajera et al., 2015). General synthesisof complexes is shown in Scheme 1. Yield: 62.61 %.M.P:[300. Anal. Calcd (%). for C32H33FN3O6PV: C, 58.54;H, 5.07; N, 6.40; V, 7.76. Found (%): C, 58.24; H, 4.76; N,6.89; V, 7.26. UV-VIS in DMSO [kmax/nm (e/M-1 cm-1)]:421 (23,729), 584 (17,100), 807 (12,391). FT-IR: tmax(cm-1) m(C=O)pyridone 1628, m(CO2)asym 1586, m(CO2)-sym 1384, m = m(CO2)asym-m(CO2)sym = 202, m(V=O)952, m(M-O) 513 cm-1. ESI-MS (m/z):654.62 [M?].

References: [1]Medicinal Chemistry Research,2016,vol. 25,p. 526 - 537.

53
oxovanadium(IV) sulfate [ No CAS ]
[ 70458-92-3 ]
[ 2848-01-3 ]
C₃₀H₂₉FN₃O₆PV [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.32%	In methanol; for 10h;pH Ca. 6.8;Reflux;	General procedure: To a hot solution of VOSO4 (2) (5 mmol) in MeOH(25.0 mL), previously prepared methanolic solution ofligand 3-(diphenylphosphino)-propionic acid (1) (5 mmol)was added, with constant stirring. Then, alkaline methanolicsolution of ciprofloxacin (5 mmol) was added. The pH of thereaction mixture was adjusted to*6.8. The resulting greensolution was refluxed for 10 h and concentrated under vacuum.Upon addition of Et2O, a green solid precipitate wasobtained, which was collected by filtration, washed withEt2O and dried in vacuo (Gajera et al., 2015). General synthesisof complexes is shown in Scheme 1. Yield: 62.61 %.M.P:[300. Anal. Calcd (%). for C32H33FN3O6PV: C, 58.54;H, 5.07; N, 6.40; V, 7.76. Found (%): C, 58.24; H, 4.76; N,6.89; V, 7.26. UV-VIS in DMSO [kmax/nm (e/M-1 cm-1)]:421 (23,729), 584 (17,100), 807 (12,391). FT-IR: tmax(cm-1) m(C=O)pyridone 1628, m(CO2)asym 1586, m(CO2)-sym 1384, m = m(CO2)asym-m(CO2)sym = 202, m(V=O)952, m(M-O) 513 cm-1. ESI-MS (m/z):654.62 [M?].

References: [1]Medicinal Chemistry Research,2016,vol. 25,p. 526 - 537.

54
oxovanadium(IV) sulfate [ No CAS ]
[ 85721-33-1 ]
[ 2848-01-3 ]
C₃₂H₃₁FN₃O₆PV [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.61%	In methanol; for 10h;pH Ca. 6.8;Reflux;	To a hot solution of VOSO4 (2) (5 mmol) in MeOH(25.0 mL), previously prepared methanolic solution ofligand 3-(diphenylphosphino)-propionic acid (1) (5 mmol)was added, with constant stirring. Then, alkaline methanolicsolution of ciprofloxacin (5 mmol) was added. The pH of thereaction mixture was adjusted to*6.8. The resulting greensolution was refluxed for 10 h and concentrated under vacuum.Upon addition of Et2O, a green solid precipitate wasobtained, which was collected by filtration, washed withEt2O and dried in vacuo (Gajera et al., 2015). General synthesisof complexes is shown in Scheme 1. Yield: 62.61 %.M.P:[300. Anal. Calcd (%). for C32H33FN3O6PV: C, 58.54;H, 5.07; N, 6.40; V, 7.76. Found (%): C, 58.24; H, 4.76; N,6.89; V, 7.26. UV-VIS in DMSO [kmax/nm (e/M-1 cm-1)]:421 (23,729), 584 (17,100), 807 (12,391). FT-IR: tmax(cm-1) m(C=O)pyridone 1628, m(CO2)asym 1586, m(CO2)-sym 1384, m = m(CO2)asym-m(CO2)sym = 202, m(V=O)952, m(M-O) 513 cm-1. ESI-MS (m/z):654.62 [M?].

References: [1]Medicinal Chemistry Research,2016,vol. 25,p. 526 - 537.

Historical Records

Technical Information

• Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
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P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
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P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
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P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
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P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
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H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 2848-01-3

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