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Chemical Structure| 7211-39-4 Chemical Structure| 7211-39-4

Structure of 7211-39-4

Chemical Structure| 7211-39-4

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CAS No.: 7211-39-4

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Product Details of [ 7211-39-4 ]

CAS No. :7211-39-4
Formula : C2H7OP
M.W : 78.05
SMILES Code : CP(C)=O
MDL No. :MFCD02824571
InChI Key :WQAWEUZTDVWTDB-UHFFFAOYSA-N
Pubchem ID :6327637

Safety of [ 7211-39-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H302+H312+H332-H315-H319-H335-H412
Precautionary Statements:P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P273-P280-P301+P312-P321-P330-P332+P313-P337+P313-P362+P364-P370+P378-P403+P233-P403+P233-P403+P233-P403+P235-P405-P501
Class:3
UN#:1993
Packing Group:Ⅲ

Application In Synthesis of [ 7211-39-4 ]

* 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 [ 7211-39-4 ]

[ 7211-39-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 615-43-0 ]
  • [ 7211-39-4 ]
  • [ 1197953-47-1 ]
YieldReaction ConditionsOperation in experiment
80% With potassium phosphate;palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 150℃; for 3.0h; Step 1 : synthesis of compound 1To a solution of 2-iodoaniline ( 1.0 eq) and dimethylphosphine oxide (1.1 eq) in DMF were added potassium phosphate ( 1.1 eq) and palladium acetate/Xantphos (catalytic). The reaction was stirred at 150 °C for 3 hours and cooled to room temperature. The solvent was evaporated and the residue was worked up with DCM/water. The crude product was purified with a column(EtOAc/MeOH 10: 1 ) to give 1 as a brown solid (80percent yield).
80% With potassium phosphate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 150℃; for 3.0h; To a solution of 2-iodoaniline (1.0 eq) and dimethylphosphine oxide (1.1 eq) in DMF were added potassium phosphate (1.1 eq) and palladium acetate/Xantphos (catalytic). The reaction was stirred at 150 °C for 3 hours and cooled to room temperature. The solvent was evaporated and the residue was worked up with DCM/water. The crude product was purified with a column (EtOAc/MeOH 10:1) to give 1 as a brown solid (80percent yield).
80% With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 150℃; for 3.0h; Synthesis of 1 (0791) (0792) To a solution of 2-iodoaniline (1.0 eq) and dimethylphosphine oxide (1.1 eq) in DMF were added potassium phosphate (1.1 eq), palladium acetate/Xantphos (catalytic). The reaction was stirred at 150° C. for 3 hours and cooled to room temperature. The solvent was evaporated and the residue was worked up with DCM/water. The crude product was purified with a column (EtOAc/MeOH 10:1) to give 1 as a brown solid (80percent yield).
79.96% With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In water; N,N-dimethyl-formamide; at 110 - 125℃; for 3.0h;Inert atmosphere; The 2 - iodo aniline (990.01 g, 4. 52 muM, 1 equivalent) and dimethyl phosphine oxide (690 g, 5.2 muM, 1.15 equiv), K3PO4(0.594 g, 0.226 muM, 0.05 wt) in DMF (5.5 L, ) and water (0.55 L) in, the reaction mixture is under the protection of nitrogen, heated to 110 - 125 ° C and stirring 3 hours. LCMS and TLC (PE: EA = 10: 1, DCM: MeOH = 10: 1 ) Display the completion of reaction. The mixture is filtered and concentrated, wherein the DMF is removed, the resulting residues of ethyl acetate (2 L) dilution. Then adding HC / EA (4 M, 2 L) make the product into a salt , There are a large quantity of solid precipitate, stirring to make it uniform dispersion, the concrete filtering, the filter cake is used which acetone (0.4 L x 3) washing, and drying solid, to obtain the target compound (817 g, yield 79.96percent IS) AS Yellow Solid
62.15% With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 100℃; for 16.0h;Inert atmosphere; 2-iodoaniline solution (12.50 g, 57.07 mmol) and Example 1J (5.35 g, 68.49 mmol), K3PO4 (14.54 g, 68.49 mmol), Xantphos (660.44 mg, 1.14 mmol) and palladium acetate ( 256.26 mg, 1.14 mmol) in DMF (80mL), the reaction mixture was stirred under nitrogen and heated to 100 deg. C and stirred for 16 hours. LCMS (DCM: methanol = 10: 1) showed the reaction was complete. The mixture was filtered and concentrated and the resulting residue was diluted with aqueous HCl (1N, 80mL), the pH is adjusted to about 2, and the resulting mixture was filtered. The filtrate (100mL × 2) and extracted with the DCM, the aqueous layer was separated, and washed with aqueous sodium bicarbonate to adjust the pH to about 9, and (200mL × 2) and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate and concentrated to dryness. The crude product was purified by recrystallization (the PE: ethyl acetate = 5: 1) to give the title compound (6.00 g, 35.47 mmol, 62.15percent yield) as a white solid.
62.15% With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 120℃; for 6.0h;Inert atmosphere; To a solution of 2-iodoaniline (1.0g, 4.57mmol, 1.Oeq) in dimethylformamide (lOmL) were added compound 128.1 (0.463g, 5.94mmol, Oeq) and potassium phosphate (1.937g, 9.14mmol, 2. Oeq). The reaction mixture was degassed for 10 min under argon atmosphere, and palladium acetate (0.103g, 0.457mmol, O. leq) and 4,5-Bis(Diphenylphosphino)-9,9-dimethylxanthene (0.529g, 0.914mmol, 0.2eq) were added. Reaction mixture was again degassed for 10 min and stirred at 120°C for 6h. After completion of reaction, reaction mixture was transferred into water and extracted with ethyl acetate. Organic layer was combined, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography and compound was eluted in 3percent methanol in dichloromethane as eluent to obtain 128.2. (0.48g, 62.15percent). MS(ES): m/z 170.16 [M+H]+
With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 0.12℃; [00366] A mMure of 2iodoaniHne (66 g, 0.393 moL 1.0 eq.), dimethyl phosphine oxide (36.4 g, 0466 meL 1.19 eq.), potasshim phosphate (92.4 g. 0.423 mol, 1.1 eq.), paNadk1m(H) acetate (4.56 g, 002 mol, 005 eq), and Xantphos (11.6g, 0.02 mel. 0.05 eq.) in DMF (700 mL) was stirred at ?120° C for ?6 h. The color of the mixture turned dark brown. Upon cooling to rt, celite (30 g) was added to the mixture. The mixture was then filtered and the filter cake was rinsed with EtOAc (2 x 250 mL). The filtrate was then concentrated in vacuo to afford a residue. [00367] Another batch of (2..aminophenyl)dimethylphosphine oxide was synthesized at the same scale as performed above, and the residue obtained from both batches were combined and purified as discussed below.[00368] To the combined residues was added EtOAc (1 L), and the resulting mixture was stirred at rt for ?1 h. The mixture was filtered, and the collected residue was washed with EtCAc (2 x 250 mL), The combined filtrate was dried over sodium sulfate, filtered and concentrated in vacuo to afford an oil. The resulting oil was dissolved in a mixture of water / concentrated hydrochloric acid (1 .2 L / 300 mL) with agitation at rt, and stirred for 30 mm. The resulting mixture was filtered, and the collected residue was washed with aqueous hydrochloric acid (10percent, 300 mL). The combined aqueous filtrate was washed with EtOAc (2 x I L washes, followed by a 500 mL wash). The aqueous layer was cooled in an ice bath (less than 10° C internal mixture temperature) and the pH of the solution was adjusted to?12 (as determined by pH paper) by adding aqueous sodium hydroxide (30percent w/w), while maintaining an internal solution temperature of less than 20° C throughout the addition. The resulting solution was extracted with IPA?DCM (1/3 v/v, 4 x I L), and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford a viscous oil, which crystallized upon standing at rt. The resulting solids were triturated with EtOAc/heptane (1/10 v/v, 2 x 150 mL) to afford (2aminophenyl)dimethylphosphine oxide as a light brown solid.
With palladium diacetate; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 100℃; for 6.0h;Inert atmosphere; 2-iodoaniline (17.5 g, 79.9 mmol) and dimethyl phosphine oxide (6.9 g, 88.5 mmol) were added,Palladium acetate (0.3 g, 1.3 mmol), Xantphos (0.77 g, 1.3 mmol),N,N-diisopropylethylamine (22.7 g, 175.8 mmol), DMF (50 mL),Magnetic stirring. Under nitrogen protection, heat to 100°C for 6 hours,The 2-iodoaniline consumption was monitored by thin layer chromatography. Cool to room temperature2,4,5-trichloropyrimidine (17.5 g, 95.9 mmol) was added and the reaction was heated to 75°C for 6 hours.The reaction was complete by thin layer chromatography. Cool to room temperature, add water 300mL,Adjust pH to 5 with 5percent hydrochloric acid and extract with ethyl acetate (100 mL x 3).Wash with sodium bicarbonate solution (100 mL), wash with saturated sodium chloride solution (100 mL × 2),Dry over anhydrous sodium sulfate. It is filtered with suction and concentrated to give a crude brown solid.Recrystallization with ethyl acetate/petroleum ether (volume ratio 1:2) gave an almost white solid 17g.Yield 67.3percent.

  • 2
  • [ 6358-77-6 ]
  • [ 7211-39-4 ]
  • 5-(dimethylphosphoryl)-2-methoxyaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 150℃; for 0.333333h;Inert atmosphere; Microwave irradiation; 5-(Dimethylphosphoryl)-2-methoxyaniline (0456) To a solution of <strong>[6358-77-6]5-bromo-2-methoxyaniline</strong> (0.404 g, 2.00 mmol) in 8 mL DMF was added dimethylphosphine oxide (0.171 g, 2.20 mmol), palladium acetate (22.4 mg, 0.0100 mmol), XANTPHOS (69.4 mg, 0.120 mmol), and potassium phosphate (0.467 g, 2.20 mmol). The mixture was purged with nitrogen, and subjected to microwaves at 150 C. for 20 minutes. The reaction mixture was concentrated and purified by silica gel chromatography (0-20% 7N ammonia in methanol:dichloromethane) to afford the desired product (0.365 g, 85% yield).
 

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