Production Method 1

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride ,  Magnesium ,  Lithium chloride Solvents: Tetrahydrofuran ,  Hexane ;  10 min, rt
1.2 2 h, rt; rt → -10 °C
1.3 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  -10 °C; -10 °C → rt; 18 h, rt
1.4 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Highly active catalysts of bisphosphine oxides for asymmetric Heck reaction

Hu, Jian; Lu, Yunpeng; Li, Yongxin; Zhou, Jianrong, Chemical Communications (Cambridge, 2013, 49(82), 9425-9427

Production Method 2

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; overnight, rt
1.2 Reagents: Ammonium chloride Solvents: tert-Butyl methyl ether ,  Water ;  5 min, rt

Reference

Practical Synthesis of Phosphinic Amides/Phosphoramidates through Catalytic Oxidative Coupling of Amines and P(O)-H Compounds

Tan, Chen; Liu, Xinyuan; Jia, Huanxin; Zhao, Xiaowen; Chen, Jian; et al, Chemistry - A European Journal, 2020, 26(4), 881-887

Production Method 3

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  30 min, rt
1.2 Solvents: Tetrahydrofuran ;  1.5 h, 25 °C; 40 min, 40 °C
1.3 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  30 min, 0 °C; 15 h, rt
1.4 Reagents: Potassium carbonate Solvents: Water ;  0 °C; 30 min, rt

Reference

Development of Effective Bidentate Diphosphine Ligands of Ruthenium Catalysts toward Practical Hydrogenation of Carboxylic Acids

Yoshioka, Shota; Wen, Ke; Saito, Susumu, Bulletin of the Chemical Society of Japan, 2021, 94(5), 1510-1524

Production Method 4

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Tetrahydrofuran ;  15 min, cooled; 4 h, rt; cooled
1.2 Reagents: Diethyl phosphite ;  cooled; 15 min, cooled; 2 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  5 min, 0 °C
1.4 Solvents: tert-Butyl methyl ether ;  5 min, 0 °C

Reference

Facile, Catalytic Dehydrocoupling of Phosphines Using β-Diketiminate Iron(II) Complexes

King, Andrew K.; Buchard, Antoine; Mahon, Mary F.; Webster, Ruth L., Chemistry - A European Journal, 2015, 21(45), 15960-15963

Production Method 5

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  0 °C; 15 min, 0 °C; 2 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Visible-Light-Induced Cascade Phosphinoylation/Cyclization of Phenacylmalononitriles with Secondary H-phosphine Oxides

Xiong, Biquan ; Shi, Chonghao; Xu, Weifeng; Liu, Yu ; Zhu, Longzhi; et al, Advanced Synthesis & Catalysis, 2022, 364(24), 4392-4401

Production Method 6

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphite ;  0 °C; 30 min, 0 °C; 2 - 12 h, rt; rt → 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Copper-Catalyzed Cross-Coupling of Alkyl and Phosphorus Radicals for C(sp3)-P Bond Formation

Li, Cheng-Kun; Tao, Ze-Kun; Shoberu, Adedamola; Zhang, Wei ; Zou, Jian-Ping, Organic Letters, 2022, 24(32), 6083-6087

Production Method 7

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphate Solvents: Tetrahydrofuran ;  0 °C; overnight, 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C

Reference

One-pot synthesis of phosphorylnaphth[2,1-d]oxazoles and products as P,N-ligands in C-N and C-C formation

Peng, Lingteng; Hu, Zhifang; Zhao, Yanting; Peng, Lifen; Xu, Zhi; et al, Organic & Biomolecular Chemistry, 2022, 20(20), 4110-4114

Production Method 8

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium ,  Iodine Solvents: Tetrahydrofuran ;  rt; 2 h, rt → 45 °C
1.2 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  0 °C; 0 °C → 45 °C; 30 min, 45 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  15 min, 0 °C

Reference

Synthesis of triarylphosphines from arylammonium salts via one-pot transition-metal-free C-P coupling

Zhang, Lei; Liu, Chengyu; Yang, Lei; Cao, Liming; Liang, Chaoming; et al, Organic & Biomolecular Chemistry, 2022, 20(19), 3897-3901

Production Method 9

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  1 h, reflux
1.2 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  2 - 3 h, reflux

Reference

Asymmetric Construction of Tertiary/Secondary Carbon-Phosphorus Bonds via Bifunctional Phosphonium Salt Catalyzed 1,6-Addition

Chen, Yuan; Yu, Zhaoyuan ; Jiang, Zhiyu; Tan, Jian-Ping; Wu, Jia-Hong; et al, ACS Catalysis, 2021, 11(22), 14168-14180

Production Method 10

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Tetrahydrofuran ;  2 h, reflux; 20 min, 0 °C
1.2 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  0 °C; 1.5 h, rt; 30 min, rt → reflux
1.3 Reagents: Hydrochloric acid Solvents: Water

Reference

Preparation of O-Protected Cyanohydrins by Aerobic Oxidation of α-Substituted Malononitriles in the Presence of Diarylphosphine Oxides

Zhang, Dapeng; Lian, Mingming ; Liu, Jia; Tang, Shukun; Liu, Guangzhi; et al, Organic Letters, 2019, 21(8), 2597-2601

Production Method 11

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C; 5 h, rt
1.2 rt

Reference

Synthesis of (Deoxy)difluoromethylated Phosphines by Reaction of R2P(O)H with TMSCF3 and Their Application in Cu(I) Clusters in Sonogashira Coupling

Yang, Xiaogang; Lu, Dong; Guan, Wenjian; Yin, Shuang-Feng ; Kambe, Nobuaki; et al, Journal of Organic Chemistry, 2022, 87(12), 7720-7733

Production Method 12

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  15 min, 0 °C; 15 min, 0 °C; 120 min, rt; rt → 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  20 min, 0 °C

Reference

A Superior Method for the Reduction of Secondary Phosphine Oxides

Busacca, Carl A.; Lorenz, Jon C.; Grinberg, Nelu; Haddad, Nizar; Hrapchak, Matt; et al, Organic Letters, 2005, 7(19), 4277-4280

Production Method 13

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Tetrahydrofuran ;  2 h, reflux
1.2 Reagents: Triethyl phosphate ;  18 h, 0 °C → rt

Reference

Highly Enantioselective Synthesis of Phosphorus-Containing ε-Benzosultams by Bifunctional Phosphonium Salt-Promoted Hydrophosphonylation

Zhang, Song; Feng, Zhenghuai; Jiang, Chunhui; Yu, Xiaojun; Pan, Jianke; et al, Chemistry - A European Journal, 2021, 27(44), 11285-11290

Production Method 14

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  0 °C; 15 min, 0 °C; 30 min, rt; rt → 0 °C
1.2 Reagents: Hydrochloric acid Solvents: tert-Butyl methyl ether ,  Water ;  5 min, 0 °C

Reference

Room temperature alkynylation of H-phosphi(na)tes and secondary phosphine oxides with ethynylbenziodoxolone (EBX) reagents

Chen, C. Chun; Waser, Jerome, Chemical Communications (Cambridge, 2014, 50(85), 12923-12926

Production Method 15

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  30 min, 0 °C; overnight, rt; rt → 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C; 0 °C

Reference

Asymmetric covalent triazine framework for enhanced visible-light photoredox catalysis via energy transfer cascade

Huang, Wei; Byun, Jeehye; Roerich, Irina; Ramanan, Charusheela; Blom, Paul W. M.; et al, Angewandte Chemie, 2018, 57(27), 8316-8320

Production Method 16

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Tetrahydrofuran
1.2 Reagents: Diethyl phosphite ;  0 °C; 30 min, 0 °C; 0 °C → rt; 16 h, rt; rt → 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

A Novel, Bipolar Polymeric Host for Highly Efficient Blue Electrophosphorescence: a Non-Conjugated Poly(aryl ether) Containing Triphenylphosphine Oxide Units in the Electron-Transporting Main Chain and Carbazole Units in Hole-Transporting Side Chains

Shao, Shiyang; Ding, Junqiao; Ye, Tengling; Xie, Zhiyuan; Wang, Lixiang; et al, Advanced Materials (Weinheim, 2011, 23(31), 3570-3574

Production Method 17

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  rt; 2 - 3 h, reflux
1.2 Reagents: Diethyl phosphite ,  Sodium hydride Solvents: Tetrahydrofuran ;  0 °C; 1 h, rt; rt; 1 h, reflux; reflux → rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Asymmetric Hydrogenation of Cationic Intermediates for the Synthesis of Chiral N,O-Acetals

Sun, Yongjie; Zhao, Qingyang; Wang, Heng; Yang, Tilong; Wen, Jialin ; et al, Chemistry - A European Journal, 2020, 26(50), 11470-11477

Production Method 18

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Tetrahydrofuran ;  20 min, 40 °C; 40 °C → 0 °C
1.2 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  10 min, 0 °C; 4 h, 45 °C
1.3 Solvents: Water
1.4 Reagents: Hydrochloric acid Solvents: Ethyl acetate ,  Water ;  30 min, rt

Reference

Synthesis of new BINAP-based aminophosphines and their 31P-NMR spectroscopy

Anstiss, Christopher; Karuso, Peter; Richardson, Mark; Liu, Fei, Molecules, 2013, 18, 2788-2802

Production Method 19

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  1 h, 22 °C → reflux; reflux → 22 °C
1.2 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  1 h, 22 °C → reflux; reflux → 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Rapid Generation of P(V)-F Bonds Through the Use of Sulfone Iminium Fluoride Reagents

Miller, Lucy P. ; Vogel, James A.; Harel, Shiraz; Krussman, Jenna M.; Melvin, Patrick R., Organic Letters, 2023, 25(11), 1834-1838

Production Method 20

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  rt; 30 min, reflux; reflux → 0 °C
1.2 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  0 °C; overnight, 0 °C
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Electro-Triggered Cascade Cyclization to Access Phosphinyl-Substituted N-Containing Heterocycles

Zhu, Peng-Wei; Ma, Hong-Mei; Li, Yang; Miao, Ling-Zhen; Zhu, Jie, Journal of Organic Chemistry, 2023, 88(4), 2069-2078

Production Method 21

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; overnight, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Nickel-Catalyzed Asymmetric Hydrogenation of α-Substituted Vinylphosphonates and Diarylvinylphosphine Oxides

Wei, Hanlin; Chen, Hao; Chen, Jianzhong ; Gridnev, Ilya D.; Zhang, Wanbin, Angewandte Chemie, 2023, 62(6),

Production Method 22

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  0 °C; 15 min, 0 °C; 2 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Cobaloxime Photocatalysis for the Synthesis of Phosphorylated Heteroaromatics

Yu, Ji-Xin; Cheng, Yuan-Yuan; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu, Angewandte Chemie, 2022, 61(40),

Production Method 23

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphate Solvents: Tetrahydrofuran ;  0 °C; 3 h, rt; rt → 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Gold-catalyzed redox cycloisomerization/nucleophilic addition/reduction: direct access to 2-phosphoryl indolin-3-ones

Zhou, Xingcui; Xiong, Ting; Jiang, Jun, Chemical Communications (Cambridge, 2022, 58(61), 8568-8571

Production Method 24

460-00-4

94940-35-9

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Dibromomethane Solvents: Tetrahydrofuran ;  rt; 1 h, reflux; reflux → 0 °C
1.2 Reagents: Diethyl phosphate Solvents: Tetrahydrofuran ;  0 °C; 1 h, reflux; reflux → 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  0 °C

Reference

Microwave-Assisted Ruthenium- and Rhodium-Catalyzed Couplings of α-Amino Acid Ester-Derived Phosphinamides with Alkynes

Li, Xue-Hong; Gong, Jun-Fang; Song, Mao-Ping, Chemistry - An Asian Journal, 2022, 17(2),

Production Method 25

352-13-6

94940-35-9

Reaction Conditions

1.1 Reagents: Diethyl phosphite Solvents: Tetrahydrofuran ;  0 °C; 30 min, 0 °C; 16 h, rt; rt → 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Enantioselective Cobalt-Catalyzed Reductive Cross-Coupling for the Synthesis of Axially Chiral Phosphine-Olefin Ligands

Zhang, Xi; Wang, Juan; Yang, Shang-Dong, ACS Catalysis, 2021, 11(22), 14008-14015

Phosphine oxide, bis(4-fluorophenyl)- Raw materials

• 4-Fluorophenylmagnesium Bromide (1.0\xa0M in THF)
• 1-Bromo-4-fluorobenzene

Phosphine oxide, bis(4-fluorophenyl)- Preparation Products

• Phosphine oxide, bis(4-fluorophenyl)- (94940-35-9)

• 1. Emerging enantiomeric resolution materials with homochiral nano-fabrications
  Ji-Ping Wei Nanoscale, 2015,7, 11815-11832
• 2. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625
• 3. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 4. Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond?
  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
• 5. Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy
  Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-Morales CrystEngComm, 2013,15, 2206-2212

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Halobenzenes Fluorobenzenes

Phosphine Oxide, Bis(4-Fluorophenyl)

Phosphine oxide, specifically bis(4-fluorophenyl)phosphine oxide, is a compound with the CAS number 94940-35-9. This chemical entity has garnered significant attention in recent years due to its unique properties and versatile applications across various fields. The compound is characterized by its molecular structure, which includes a central phosphorus atom bonded to two 4-fluorophenyl groups and an oxygen atom. This configuration imparts distinctive electronic and steric properties to the molecule, making it valuable in both academic research and industrial applications.

The synthesis of bis(4-fluorophenyl)phosphine oxide typically involves the oxidation of the corresponding phosphine precursor, bis(4-fluorophenyl)phosphine. Recent advancements in catalytic methods have enabled more efficient and selective syntheses of this compound, reducing production costs and enhancing purity. Researchers have also explored alternative synthetic pathways, such as using transition metal catalysts or microwave-assisted techniques, to optimize the reaction conditions further.

In terms of physical properties, bis(4-fluorophenyl)phosphine oxide exhibits a high melting point and moderate solubility in organic solvents. Its thermal stability is another notable feature, making it suitable for applications that require exposure to elevated temperatures. The compound's electronic structure, influenced by the electron-withdrawing fluorine substituents on the phenyl rings, contributes to its reactivity in various chemical transformations.

One of the most promising areas of application for bis(4-fluorophenyl)phosphine oxide is in catalysis. Recent studies have demonstrated its effectiveness as a ligand in transition metal-catalyzed reactions, such as cross-coupling reactions and enantioselective syntheses. The fluorinated phenyl groups provide both electronic tuning and steric bulk, which are crucial for achieving high catalytic activity and selectivity. For instance, this compound has been employed as a ligand in palladium-catalyzed Suzuki-Miyaura couplings, where it facilitates the formation of biaryl compounds with excellent yields and enantioselectivity.

Beyond catalysis, bis(4-fluorophenyl)phosphine oxide has found utility in materials science. Its ability to coordinate with metal ions makes it a valuable component in the synthesis of metal-organic frameworks (MOFs) and coordination polymers. Recent research has highlighted its role in constructing porous materials with tailored properties for gas storage and separation applications. The compound's compatibility with various metal ions and its structural flexibility contribute to its versatility in this domain.

The biological activity of bis(4-fluorophenyl)phosphine oxide is another area that has attracted scientific interest. Preclinical studies have shown that this compound exhibits potential anticancer activity by modulating cellular signaling pathways. The fluorinated phenyl groups enhance bioavailability and stability within biological systems, making it a promising candidate for drug development. Researchers are currently investigating its mechanism of action and exploring strategies to optimize its pharmacokinetic properties for therapeutic use.

In conclusion, bis(4-fluorophenyl)phosphine oxide (CAS No: 94940-35-9) is a multifaceted compound with significant potential across diverse fields. Its unique chemical properties, coupled with recent advancements in synthesis and application techniques, position it as a valuable tool in modern chemistry and materials science. As research continues to uncover new functionalities and optimize its use, this compound is poised to play an increasingly important role in both academic and industrial settings.

• 474049-42-8(Phosphine oxide, tris(3,4,5-trifluorophenyl)-)
• 84350-76-5(PHOSPHINE OXIDE, TRIS(2-FLUOROPHENYL)-)
• 474049-41-7(PHOSPHINE OXIDE, TRIS(3,4-DIFLUOROPHENYL)-)
• 54300-32-2(Bis(4-fluorophenyl)phenylphosphine oxide)
• 18437-79-1(Phosphine oxide,tris(4-fluorophenyl)-)
• 206448-52-4(Phosphine oxide, tris(3,5-difluorophenyl)-)
• 18437-73-5(Phosphine oxide, (4-fluorophenyl)diphenyl-)
• 54300-35-5(Phosphine oxide, (3-fluorophenyl)diphenyl-)
• 84350-74-3(Phosphine oxide, (2-fluorophenyl)diphenyl-)
• 874907-57-0(Phosphine oxide, (4-fluoro-2-naphthalenyl)diphenyl-)