2-(Diphenylphosphino)benzoic acid

Base Information

• Chemical Name: 2-(Diphenylphosphino)benzoic acid
• CAS No.: 17261-28-8
• Deprecated CAS: 1627500-87-1
• Molecular Formula: C19H15 O2 P
• Molecular Weight: 306.301
• Hs Code.: 29319090
• European Community (EC) Number: 241-293-7
• UNII: 5TH63M8SLV
• DSSTox Substance ID: DTXSID4066179
• Nikkaji Number: J286.991H
• Wikipedia: 2-Diphenylphosphinobenzoic_acid
• Wikidata: Q72473455
• ChEMBL ID: CHEMBL361405
• Mol file: 17261-28-8.mol

Synonyms:2-(Diphenylphosphino)benzoic acid;17261-28-8;2-Diphenylphosphinobenzoic acid;Benzoic acid, 2-(diphenylphosphino)-;2-diphenylphosphanylbenzoic acid;o-Diphenylphosphinobenozic acid;C19H15O2P;(2-Carboxyphenyl)diphenylphosphine;2-(diphenylphosphanyl)benzoic acid;Benzoic acid, (diphenylphosphino)-;EINECS 241-293-7;MFCD00674024;5TH63M8SLV;2-Diphenylphosphanyl-benzoic acid;EC 241-293-7;2- diphenylphosphino benzoic acid;2-(diphenylphosphino)-benzoic acid;O-(DIPHENYLPHOSPHINO)BENZOIC ACID;UNII-5TH63M8SLV;diphenylphosphinobenzoic acid;SCHEMBL989596;CHEMBL361405;DTXSID4066179;Diphenyl(O-carboxyphenyl) phosphine;AMY42203;BCP18923;2-(Diphenylphosphino)benzoic acid #;C19-H15-O2-P;AKOS015840662;CS-W007975;SC11159;2-(Diphenylphosphino)benzoic acid, 97%;AS-14899;LS-37329;SY009857;D3242;FT-0637518;EN300-225991;F10199;W-110451;(2-CARBOXYPHENYL)DIPHENYLPHOSPHINE;2-(DIPHENYLPHOSPHINO)BENZOIC ACID;DPPBAC

Chemical Property of 2-(Diphenylphosphino)benzoic acid

Chemical Property:

• Appearance/Colour: white to yellow solid
• Vapor Pressure: 6.4E-09mmHg at 25°C
• Melting Point: 174-181 °C(lit.)
• Boiling Point: 451 °C at 760 mmHg
• PKA: 3.72±0.36(Predicted)
• Flash Point: 226.5 °C
• PSA: 50.89000
• Density: g/cm³
• LogP: 3.14300
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 306.08096671
• Heavy Atom Count: 22
• Complexity: 340

Purity/Quality:

99%+ ^*data from raw suppliers

2-(Diphenylphosphino)benzoic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3C(=O)O
• Uses: The ligand (R ,R )‐1,2‐Bis(aminocarbonylphenyl‐2′‐diphenylphosphino)cyclohexane[138517-61-0] can be prepared by the coupling of (1R ,2R )‐(-)‐1,2‐diaminocyclohexane [20439-47-8] with 2‐(diphenylphosphino)benzoic acid [17261-28-8], using reagents such as DCC. An alternative procedure has been developed where by (1R ,2R )‐(+)‐1,2‐diaminocyclohexane L‐tartrate salt [39961-95-0] is coupled to a mixed anhydride of 2‐(diphenylphosphino)benzoic acid and diphenylchlorophosphate.The procedure is reproduced below 2‐(Diphenylphosphino)benzoic acid (20 g, 65.3 mmol, 2 equiv) is suspended in dichloromethane (150 mL) and cooled in an ice‐water bath to 0°C (internal temperature). Triethylamine (10.1 mL, 71.8 mmol, 2.2 equiv) is added dropwise and a clear solution is obtained. This process is exothermic and a rise in temperature to 5°C is observed. The solution is re‐cooled to 0°C and diphenylchlorophosphate (13.4 mL, 64.7 mmol, 1.98 equiv) is added slowly, maintaining the internal temperature between 0–5°C. The yellow solution is stirred for 1 h at 0°C. (1R, 2R )‐(+)‐1,2‐Diaminocyclohexane‐L‐tartrate salt (8.63 g, 32.65 mmol, 1 equiv) is suspended in water (50 mL, 5.8 vol) and potassium carbonate (15 g, 107.8 mmol, 3.3 equiv) is added. This process is exothermic and a clear solution is obtained after approximately 10 min. After 30 min, the clear aqueous solution of diamine is added to the mixed anhydride solution at 0°C, and the resulting yellow two‐phase mixture is stirred for 2 h at 0°C, then allowed to warm to room temperature. After 14 h, the mixture is poured into a separating funnel and 200 mL of dichloromethane and 100 mL of water are added. The organic phase is separated, washed with 2 N HCl (100 mL) and saturated aqueous NaHCO3 solution (100 mL), then dried over magnesium sulfate. The dried organic phase is filtered through a silica pad and the pad is washed with dichloromethane (50 mL). The combined filtrates are evaporated to dryness under reduced pressure, producing a yellow foam (22.3 g, 99% crude). The foam is crystallized from boiling acetonitrile (390 mL, 17.5 vol) to afford a white crystalline solid. The solid is dried under vacuum to provide the phosphine ligand (15 g, 67%). 2-(Diphenylphosphino)benzoic Acid is used in small molecule control of protein function through staudinger reduction.

Technology Process of 2-(Diphenylphosphino)benzoic acid

There total 44 articles about 2-(Diphenylphosphino)benzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl 2-diphenylphosphinobenzoate (79932-99-3) → ortho-diphenylphosphinobenzoic acid (17261-28-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 70 ℃; for 12h;

DOI:10.1021/jo000821m

Reference yield: 98.0%

butyl magnesium bromide (693-04-9) + (+/-)-(E)-2-[2-(diphenylphosphanyl)benzoyloxy]-1-phenyl-3-pentene (370867-96-2) → ortho-diphenylphosphinobenzoic acid (17261-28-8) + (+/-)-(E)-4-methyl-1-phenyl-2-octene + [((E)-2-Propenyl)-hexyl]-benzene

Guidance literature:

With copper(I) bromide dimethylsulfide complex; In diethyl ether; at 20 ℃; for 2h;

DOI:10.1002/1615-4169(200107)343:5<429::AID-ADSC429>3.0.CO;2-K

Reference yield: 97.0%

2-diphenylphosphanyl benzoic acid tert-butyl ester → ortho-diphenylphosphinobenzoic acid (17261-28-8)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1055/s-0028-1087668

upstream raw materials:

diphenylphosphane

ortho-chlorobenzoic acid

sodium diphenylphosphide

carbon dioxide

Downstream raw materials:

(-)-1,3:4,6-di-O-benzylidene-D-mannitol, bis<2-(diphenylphosphino)benzoate>

(1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane

(-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane

(S)-(+)-bis-O-<2-(diphenylphosphino)benzyl>-1,1'-binaphthol

Refernces

• 1、 Breit, Bernhard,Zahn, Stephan K.. "Domino hydroformylation-Wittig olefination-hydrogenation". . p. 6171 - 6179. Retrieved 2005.
• 2、 Ravindar,Hemling,Schumann,Blum. "A novel convenient synthesis of aryl phosphines containing reactive functional groups". . p. 1453 - 1459. Retrieved 1992.
• 3、 Guo, Rui,Li, Junxia,Sang, Jiale,Xiao, Haijing,Zhang, Guozhu. "Development of Novel Phosphino-Oxazoline Ligands and Their Application in Asymmetric Alkynlylation of Benzylic Halides". . . Retrieved 2022/03/27.
• 4、 -. "ORGANIC MAGNESIUM PHOSPHIDE AND MANUFACTURING METHOD THEREOF, ORGANIC MAGNESIUM PHOSPHIDE COMPLEX AND MANUFACTURING METHOD THEREOF, AND MANUFACTURING METHOD OF ORGANIC PHOSPHORUS COMPOUND USING SAID PHOSPHIDE". Paragraph 014-0217. . Retrieved 2019/08/26.