22749-43-5

Basic information

• Product Name: 6-Chlorobenzo[c][1,2]benzoxaphosphinine
• Synonyms: 6-Chlorodibenz[c,e][1,2]oxaphosphorin;6-chloro-6H-dibenzo[c,e][1,2]oxaphosphinine;6-CHLOROBENZO[C][1,2]BENZOXAPHOSPHININE;10-Chloro-9,10-Dihydro-9-oxa-10-phosphaphenanthrene;6-Chloro-6H-dibenz[c,e][1,2]oxaphosphorin;6H-Dibenz(C,E)(1,2)oxaphosphorin, 6-chloro-
• CAS NO: 22749-43-5
• Molecular Formula: C₁₂H₈ClOP
• Molecular Weight: 234.62
• Mol File: 22749-43-5.mol

Chemical Properties

• Melting Point: 87 °C
• Boiling Point: 374.6 °C at 760 mmHg
• Flash Point: 180.3 °C
• Appearance: /
• Vapor Pressure: 1.78E-05mmHg at 25°C
• CAS DataBase Reference: 6-Chlorobenzo[c][1,2]benzoxaphosphinine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chlorobenzo[c][1,2]benzoxaphosphinine(22749-43-5)
• EPA Substance Registry System: 6-Chlorobenzo[c][1,2]benzoxaphosphinine(22749-43-5)

Safety Data

• Hazardous Substances Data: 22749-43-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry Research:
6-Chlorobenzo[c][1,2]benzoxaphosphinine is used as a key intermediate in the synthesis of complex organic compounds. Its reactivity and structural features make it a valuable tool for researchers in organic chemistry, facilitating the development of novel organic molecules with potential applications in various fields.
Used in Materials Science:
In the materials science industry, 6-Chlorobenzo[c][1,2]benzoxaphosphinine is utilized as a precursor for the development of new materials with unique properties. Its incorporation into material structures can lead to advancements in areas such as electronics, optoelectronics, and nanotechnology.
Used in Medicinal Chemistry:
6-Chlorobenzo[c][1,2]benzoxaphosphinine is employed as a building block in the design and synthesis of pharmaceutical compounds. Its potential applications in medicinal chemistry include the development of new drugs and drug candidates, as well as the improvement of existing medications.
Used in Chemical Biology:
6-Chlorobenzo[c][1,2]benzoxaphosphinine serves as a valuable probe in chemical biology, enabling researchers to study the interactions between small molecules and biological systems. Its unique structure allows for the exploration of novel biochemical pathways and the development of new bioactive compounds.

InChI:InChI=1/C12H8ClOP/c13-15-12-8-4-2-6-10(12)9-5-1-3-7-11(9)14-15/h1-8H

Synthetic route

2-Phenylphen-1-oxydichlorphosphan (33771-47-0) → p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5)

Conditions	Yield
With zinc(II) chloride at 150℃; for 2h;	100%
With zinc(II) chloride at 194℃; for 1.25h;	79%
With aluminium trichloride In n-heptane
With zinc(II) chloride at 250℃; for 2h;
With zinc at 180℃; for 3h; Inert atmosphere;

2-Phenylphenol (90-43-7) → p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5)

Conditions	Yield
With zinc(II) chloride; phosphorus trichloride at 20 - 180℃; for 7h;	100%
With anhydrous phosphorus trichloride; phosphorus trichloride; Zinc chloride In 5,5-dimethyl-1,3-cyclohexadiene	95%
Stage #1: 2-Phenylphenol With phosphorus trichloride at 140℃; for 5h; Inert atmosphere; Neat (no solvent); Stage #2: With zinc(II) chloride at 210℃; for 3h; Inert atmosphere; Neat (no solvent);	90%

2-Phenylphenol (90-43-7) + diphenyl ether , 4-oxy-diphenyl → p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus trichloride / 5 h / 148 °C 2: 79 percent / ZnCl2 / 1.25 h / 194 °C View Scheme

2-Phenylphenol (90-43-7) + phosphorus trichloride (7719-12-2, 52843-90-0) → p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5)

Conditions	Yield
Zinc chloride In toluene

9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5)

Conditions	Yield
With phosphorus trichloride In chloroform for 3h; Inert atmosphere; Reflux;
With phosphorus trichloride In chloroform for 4h; Inert atmosphere; Reflux;

9,10-dihydro-9-oxa-10-phosphaphenanthrene (25072-46-2) → p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5)

Conditions	Yield
With phosphorus trichloride In chloroform for 3h; Inert atmosphere; Reflux;

tris(2-phenylphenyl)phosphite (2752-19-4) → p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5)

Conditions	Yield
With zinc(II) chloride; phosphorus trichloride at 200℃; for 4h; Temperature;	35 g

2,2'-dihydroxybiphenyl (1806-29-7) → p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5)

Conditions	Yield
With phosphorus trichloride In toluene at 140℃; for 8h; Cooling with ice;

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + 2,4,6-triamino-s-triazine (108-78-1) → 2,4,6-tris(9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-ylamino)-1,3,5-triazine

Conditions	Yield
With 1-methyl-1H-imidazole at 100℃; for 16h; Inert atmosphere;	100%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + C20H17O3P → 6H-dibenz[c,e][1,2]oxaphosphorin,6'6-(1,2-phenethyl)bis-,6'6-dioxide (1631149-46-6)

Conditions	Yield
Stage #1: p-chlorodibenzo[c.e][1,2]oxaphosphorine; C20H17O3P With triethylamine at 10℃; for 2h; Stage #2: With Methyl benzenesulfonate at 100 - 150℃; for 5h;	99.3%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + recorcinol (108-46-3) → 6,6'-(1,3-phenylenebis(oxy))bis(6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide)

Conditions	Yield
Stage #1: p-chlorodibenzo[c.e][1,2]oxaphosphorine; recorcinol In toluene at 20 - 120℃; for 6h; Heating / reflux; Stage #2: With ammonia In toluene at 20℃; for 0.0833333h; Stage #3: With water; ozone more than 3 stages;	98.9%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) → 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5)

Conditions	Yield
With water; hydrogenchloride at 80℃; for 1h; Product distribution / selectivity;	98%
With water In toluene for 4h; Heating / reflux;	95%
In ethanol
With water
With water	10.1 g

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + (-)-menthol (2216-51-5) → 6-(1R,2S,5R)-(-)-menthyl-dibenzo[c.e][5,6]oxaphosphorine

Conditions	Yield
With triethylamine In toluene at 26℃; for 3h;	97%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) → 6-chloro-6H-dibenzo[c,e]-[1,2]oxaphosphinine 6-sulfide (30343-12-5)

Conditions	Yield
With sulfur at 130 - 160℃; for 5h; Inert atmosphere;	95%
With sulfur
Multi-step reaction with 2 steps 1: hydrogen sulfide; sodium hydroxide / water; toluene / 20 °C 2: chloroform; triethylamine / tetrachloromethane / 0 °C View Scheme
Multi-step reaction with 3 steps 1: water 2: tetraphosphorus decasulfide / toluene / 17 h / 40 - 55 °C / Inert atmosphere 3: chloroform; triethylamine / tetrachloromethane / 0 °C View Scheme
With sulfur; triethylamine In toluene at 20℃; for 6h; Inert atmosphere; Reflux;

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + (S)-1-phenyl-ethylamine (2627-86-3) → 6-(S)-(-)-α-methyl-benzylamino-dibenzo[c.e][5,6]oxaphosphorine

Conditions	Yield
With triethylamine In toluene at 26℃; for 3h;	95%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + chloro-trimethyl-silane (75-77-4) + 2-bromoanisole (578-57-4) → 2'-[di-o-anisylphosphanyl]-2-(trimethylsilyloxy)-1,1'-biphenyl (1268251-51-9)

Conditions	Yield
Stage #1: 2-bromoanisole With tert.-butyl lithium In diethyl ether; pentane at 20℃; for 2h; Inert atmosphere; Stage #2: p-chlorodibenzo[c.e][1,2]oxaphosphorine In tetrahydrofuran; diethyl ether; pentane at -90 - 20℃; Inert atmosphere; Stage #3: chloro-trimethyl-silane In tetrahydrofuran; diethyl ether; pentane at 20℃; for 2h; Inert atmosphere;	95%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + phenol (108-95-2) → 6-phenoxy-6H-dibenz<1,2>oxaphosphorin

Conditions	Yield
With triethylamine at 210℃; for 4h;	94%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + diethylamine (109-89-7) → 2-diethlylaminodibenzo[c.e][1,2]oxaphosphorine

Conditions	Yield
In toluene at 26℃; for 3h;	94%
In toluene at 26℃; for 3h;
In toluene at 26℃; for 4h; Inert atmosphere;
In toluene at 20℃; for 3h; Inert atmosphere;

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + 1-(6-oxidodibenzo[c,e][1,2]oxaphosphinin-6-yl)ethan-1-aminium chloride → 6-(1-(bis(6H-dibenzo[c,e][1,2]oxaphosphinin-6-yl)amino)ethyl)dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions	Yield
at 40℃; for 18h; Inert atmosphere;	94%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + methanol (67-56-1) → 10-methoxy-10H-9-oxa-10-phosphaphenanthrene (37632-28-3)

Conditions	Yield
With triethylamine In toluene at 50℃; for 2h;	92%
With pyridine In diethyl ether; benzene

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + 2-methyl-but-3-yn-2-ol (115-19-5) → 6-(3-methylbuta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions	Yield
With pyridine In diethyl ether at 0 - 28℃; for 8h;	92%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 6-(2-cyclohexylidenevinyl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions	Yield
With pyridine In diethyl ether at 0 - 28℃;	91%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + phenylmagnesium bromide → 2'-hydroxy-2-diphenylphosphinobiphenyl (155566-51-1)

Conditions	Yield
In tetrahydrofuran at 26℃; for 20h;	90%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + acetophenone (98-86-2) → 6H-dibenz[c,e][1,2]oxaphosphorin,6'6-(1,2-phenethyl)bis-,6'6-dioxide (1631149-46-6)

Conditions	Yield
With phosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene; water at 160℃; for 4.5h; Concentration; Temperature; Reagent/catalyst; Inert atmosphere;	90%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) → 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-sulfide (1259405-60-1)

Conditions	Yield
With hydrogen sulfide; sodium hydroxide In water; toluene at 20℃;	89%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + 3-ethyl-1-pentyn-3-ol (6285-06-9) → 6-(3-ethylpenta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions	Yield
With pyridine In diethyl ether at 0 - 28℃;	89%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + triethylamine (121-44-8) → triethylammonium 6H-dibenzo[c,e][1,2]oxaphosphinine-6-thiolate 6-sulfide (1259405-65-6)

Conditions	Yield
With sulfur In toluene at 20℃; for 8h; Inert atmosphere; Reflux;	87%

1,4-dihydroxybut-2-yne (110-65-6) + p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) → C28H20O4P2

Conditions	Yield
With N-ethylmorpholine; In dichloromethane at 0 - 20℃;	86%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + meparfynol (77-75-8) → 6-(3-methylpenta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions	Yield
With pyridine In diethyl ether at 0 - 28℃; diastereoselective reaction;	86%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + 2-Phenyl-3-butyn-2-ol (127-66-2) → 6-(3-phenylbuta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions	Yield
With pyridine In diethyl ether at 0 - 28℃;	86%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + 1-ethynylcyclopentanol (17356-19-3) → 6-(2-cyclopentylidenevinyl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions	Yield
With pyridine In diethyl ether at 0 - 28℃;	85%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + 3,5-dimethyl-1-hexyn-3-ol (107-54-0) → 6-(3,5-dimethylhexa-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions	Yield
With pyridine In diethyl ether at 0 - 28℃; diastereoselective reaction;	84%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) → C36H24N3O3P3

Conditions	Yield
With trimethylsilylazide In toluene at 50℃; for 24h; Inert atmosphere;	83.4%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + (2,4,6-triisopropylphenyl)magnesium bromide (108894-99-1) → 10-(2,4,6-triisopropyl-phenyl)-10H-9-oxa-10-phospha-phenanthrene (843615-07-6)

Conditions	Yield
In tetrahydrofuran at 26℃;	82%
In tetrahydrofuran at 0 - 26℃;

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + ethylmagnesium bromide (925-90-6) → (2'-hydroxy-biphenyl-2-yl)-diethylphosphane (1093348-90-3)

Conditions	Yield
In tetrahydrofuran at 20 - 65℃; Inert atmosphere;	82%

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + 2-(pyridine-2-yl)propan-2-ol (37988-38-8) → 2-ethyl(1'-methyl-1'-hydroxy)pyridine-6H-dibenz[c,e][1,2]oxaphosphorin (605666-57-7)

Conditions	Yield
Stage #1: 2-(pyridine-2-yl)propan-2-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: p-chlorodibenzo[c.e][1,2]oxaphosphorine In tetrahydrofuran; hexane at 20℃; for 12h; Further stages.;	80%

Upstream product

• 1806-29-7 2,2'-dihydroxybiphenyl 
• 2752-19-4 tris(2-phenylphenyl)phosphite 
• 25072-46-2 9,10-dihydro-9-oxa-10-phosphaphenanthrene 
• 35948-25-5 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 
• 90-43-7 2-Phenylphenol 
• 7719-12-2 phosphorus trichloride 
• 33771-47-0 2-Phenylphen-1-oxydichlorphosphan 

Downstream Products

• 35948-25-5 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 
• 155566-51-1 2'-hydroxy-2-diphenylphosphinobiphenyl 
• 139995-03-2 6-Phenyl-6H-dibenzo[c,e][1,2]oxaphosphorine 
• 843615-09-8 (2'-hydroxy-[1,1'-biphenyl]-2-yl)diphenylphosphine oxide 
• 36240-32-1 6-(phenyl)-6H-dibenzo[c,e][1,2λ⁵]oxaphosphinine-6-oxide 
• 843615-07-6 10-(2,4,6-triisopropyl-phenyl)-10H-9-oxa-10-phospha-phenanthrene 
• 917477-93-1 (2'-diphenylphosphino-biphenyl-2-yl)-oxydibenzo[c.e][5,6]oxaphosphorine 
• 1268251-47-3 2'-[tert-butyl(p-tolyl)phosphanyl]-2-(trimethylsilyloxy)-1,1'-biphenyl 
• 1268251-48-4 2'-[mesityl(methyl)phosphanyl]-2-(trimethylsilyloxy)-1,1'-biphenyl 
• 1268279-72-6 C₂₂H₂₃O₂P 
• 1268251-49-5 2'-[tert-butyl(mesityl)phosphanyl]-2-(trimethylsilyloxy)-1,1'-biphenyl 
• 1268251-55-3 2'-[tert-butyl(p-tolyl)phosphanyl]-2-hydroxy-1,1'-biphenyl 
• 1268279-68-0 2'-[tert-butyl(p-tolyl)phosphanyl]-2-hydroxy-1,1'-biphenyl-borane 
• 1268279-70-4 2-hydroxy-2'-[mesityl(methyl)phosphanyl]-1,1'-biphenyl-borane 

Relevant articles and documents

Cleavage of Aromatic C-O Bonds via Intramolecular SNAr Reaction and Preparation of P, C, Axial-Stereogenic Menthyl Phosphine Derivatives

Phosphine ligands with up to six chiral sites were prepared, starting from 2-phenylphenol, via O- and P-alkylation, cyclization, and coupling. The chirality was transferred from (L)-menthyl to phosphorus, α-carbon, and axis, to achieve excellent diastereoselectivities. During an intramolecular SNAr reaction with alkoxyl as the leaving groups, the C-O bond was converted to a C-C bond. Both phosphine boranes and oxides could be used for the conversions, affording a series of cyclic phosphines.

Multinuclear NMR Studies and Spin System Analyses on Dibenzo[c.e][1,2]Oxaphosphorine 2-Oxides

2H-Dibenzo[c.e][1,2]oxaphosphorine 2-oxide (HDOPO), 2-(N,N-diethylamino)-dibenzo[c.e][1,2]oxaphosphorine 2-oxide (DEADOPO), and 2-ethoxy-dibenzo[c.e][1,2]oxaphosphorine 2-oxide (EtODOPO) are fully characterized in CDCl3 by 1H, 13C, 31P, and 15N NMR spectroscopy on 800- and 500-MHz instruments. A strategy enabling their unambiguous signal assignment is presented, with special emphasis on 2D 1H,13C HMBC spectra. Additional line-shape iterations of the aromatic 1H multiplets (ABCDX and ABCDEX spin systems) provided all long-range nJH,H and nJP,H coupling constants with utmost precision. The experimental results augmented with those of the model compound phenylphosphonous acid clearly demonstrate that nJH,H couplings of the PH proton as well as the nJP,C values do not decrease in a monotonic manner with the number of intervening bonds from the phosphorus atom. This fact may potentially lead signal misassignments, if the analysis starts out from the coupling constants, as it occurred for HDOPO in the recent publication by Wagner et al. (Phosphorus, Sulfur and Silicon, 187, 2012, 781-798). The corrected assignment will be given in the present paper. Finally, the A2M3X or ABM3X type 1H spectral patterns of ethyl groups are also analyzed and explicit equations are derived to evaluate the strongly coupled ABM3X multiplets in EtODOPO.

Practical synthesis of 6-chloro-dibenzo[c.e][1,2]oxaphosphorine

The title P-heterocycle 3, a versatile intermediate in synthesis, was prepared by two independent methods. The first involves an environmentally friendly version of an old protocol starting from 2-phenylphenol (1) and phosphorus trichloride. Their interaction could be accomplished at 50C under solventless conditions. Cyclization of the intermediate (2) so obtained could be realized best under microwave conditions at 150C in the presence of ZnCl2. This method offers advantages over the traditional ones. According to another approach, the chloro-dibenzooxaphosphorine (3) was obtained by the novel reaction of 6H-dibenzo[c.e][1,2]oxaphosphorine-6-oxide (4) with phosphorus trichloride in boiling chloroform. Efficiency of the syntheses was demonstrated by converting the crude product 3 to a more stable phosphonic amide (6) that was stable enough to be isolated.

Preparation method of DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) and intermediate of DOPO

The invention relates to a preparation method of DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) and an intermediate of DOPO and belongs to the field of chemistry. Aiming at solving the technical problems, the invention provides the preparation method of the DOPO intermediate CDOP; the method comprises the following steps: raising the temperature of a mixture of o-phenylphenol, zinc chloride and phosphorus trichloride to 60 DEG C to 140 DEG C and carrying out esterification reaction; continually raising the temperature to 160 DEG C to 220 DEG C and reacting to obtain the product. Byadopting the preparation method provided by the invention, the phosphorus trichloride can be added in one step in a material feeding process and the excessive phosphorus trichloride and reaction byproducts do not need to be removed by decompressing and distilling after the reaction is finished, so that the production operation is greatly simplified; compared with an existing technology, the preparation method has remarkable advantages.

One-pot synthesis of new 6-(alkylamine)dibenzo[c,e][1,2]oxaphosphinine-6-oxides

Several new 6-(alkylamine)-6H-dibenz[c,e][1,2]oxaphosphinine-6-oxides were prepared through a one-pot reaction, starting with 2-phenylphenol, phosphorus trichloride, and a Zn catalyst, to form 6-chloro-6H-dibenz[c,e][1,2]oxaphosphine. The alkylamine derivatives were subsequently prepared through a nucleophilic substitution reaction involving aliphatic amines and H2O2oxidation under soft conditions. This method has the advantages that it is a one-pot synthesis, does not require an inert atmosphere, and involves in situ catalyst formation.

Preparation method of DiDOPO compound

The invention discloses a preparation method of a DiDOPO compound. The preparation method is characterized by comprising the step of reacting by virtue of a ketone compound II and a chlorinated organic phosphine compound III in the presence of an oxygen-containing compound, so as to obtain a compound I. Compared with an existing synthetic method for preparing DiDOPO through reaction of DOPO and aromatic alkyl ketone under the catalysis of phosphorus oxychloride and the like, the preparation method has the advantages that reaction steps are shortened, the cost is effectively lowered, the operability and safety of a process are improved, a product is relatively easily purified, and the yield of the product is relatively high.

Method for synthesizing 9, 10-dihydro-9-oxygen-10-phosphaphenanthrene-10-oxide

The invention discloses a method for synthesizing 9, 10-dihydro-9-oxygen-10-phosphaphenanthrene-10-oxide. The method includes adding phosphorus trichloride into excessive o-phenylphenol drop by drop and carrying out esterification reaction to obtain phosphorous acid tri-orthophthalic phenyl ester; adding ZnCl2 catalysts into the phosphorous acid tri-orthophthalic phenyl ester, adding phosphorus trichloride into the phosphorous acid tri-orthophthalic phenyl ester drop by drop and carrying out acylation reaction to obtain 6-chlorine-(6 hydrogen)-dibenzo-(c, e)-oxygen phosphorus heterocyclic hexa-rings; sequentially carrying out hydrolysis reaction and cyclization reaction on the 6-chlorine-(6 hydrogen)-dibenzo-(c, e)-oxygen phosphorus heterocyclic hexa-rings to obtain the 9, 10-dihydro-9-oxygen-10-phosphaphenanthrene-10-oxide. The method has the advantages that the o-phenylphenol can be prevented from being volatilized or oxidized at high temperatures, the method is high in reaction speed and suitable for industrial production, and target products are high in yield and purity.

HALOGEN-FREE ACTIVE ESTER CURING AGENT COMPOUND FOR EPOXY RESINS, FLAME RETARDANT COMPOSITION COMPRISING SAME, ARTICLES MADE THEREFROM AND METHOD OF MAKING SAID COMPOUND

There is provided herein a curing agent compound for curing thermosetting resins, e.g., epoxy resins, a composition comprising a thermoplastic and/or thermosetting resin, e.g., an epoxy resin and the curing agent, an article comprising the curing agent, and a method of making the curing agent.

Superacid-catalyzed Friedel–Crafts phosphination of 2-hydroxybiphenyls with phosphorus trichloride

Cyclic phosphorus compounds, 6H-dibenz[c,e][1,2]oxaphosphorin-6-oxide derivatives, were efficiently synthesized by the Friedel–Crafts reaction of 2-hydroxybiphenyls with phosphorus trichloride in the presence of superacids, especially trifluoromethanesulfonic acid (TfOH) as a catalyst. TfOH was investigated for the first time as an effective catalyst for the aromatic phosphination of 2-hydroxybiphenyls.

TETRAMERISATION OF ETHYLENE

A process for the tetramerisation of ethylene includes contacting ethylene with a catalyst under ethylene oligomerisation conditions. The catalyst comprises a source of chromium, a ligating compound, and an activator. The ligating compound includes a phosphine that forms part of a cyclic structure.