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[ CAS No. 115029-22-6 ]

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Chemical Structure| 115029-22-6
Chemical Structure| 115029-22-6
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CAS No. :115029-22-6 MDL No. :MFCD00040980
Formula : C8H4F4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :208.11 g/mol Pubchem ID :-
Synonyms :

Safety of [ 115029-22-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 115029-22-6 ]

  • Downstream synthetic route of [ 115029-22-6 ]

[ 115029-22-6 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 115029-22-6 ]
  • [ 6638-79-5 ]
  • [ 680610-54-2 ]
YieldReaction ConditionsOperation in experiment
With pyridine; oxalyl dichloride In dichloromethane at 20℃; 1.1 Intermediates 1-15; Method A: Substituted (2-FLUORO-PHENYL)-(4-METHOXY-PHENYL)-METHANONE; Step A; SUBSTITUTED-N-METHOXY-N-METHYL-2-FLUOROBENZAMIDE General Methods Intermediates 1-15 Method A: Substituted (2-FLUORO-PHENYL)- (4-METHOXY-PHENYL)-METHANONE Step A SUBSTITUTED-N-METHOXY-N-METHYL-2-FLUOROBENZAMIDE A mixture of the substituted benzoic acid (1 equivalent) and OXALYL CHLORIDE (1 equivalent) in dry [CH2CI2] was treated with a catalytic amount of DMF. The reaction mixture was stirred until gas evolution ceased. To the cooled solution was added N, O- dimethylhydroxylamine hydrochloride (1.2 equivalents) in one portion. Pyridine (0.24 mL/mmol) was added dropwise and the mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated in vacuo and the residue partitioned with EtOAc and 1 N HCI. The organic phase was washed with saturated aqueous [NAHCO3] and brine. The organic phase was dried NA2SO4 and concentrated in vacuo to provide reasonably pure intermediate substituted-N-methoxy-N-methyl-2- fluorobenzamide. Intermediate 1 (2-FLUORO-3-TRIFLUOROMETHYLPHENYL)- (4-METHOXY-PHENYL)-METHANONE] Step 1: [2-FLUORO-N-METHOXY-N-METHYL-3- (TRIFLUOROMETHVL) benzamide Prepared according to Method A step A from 2-fluoro-3-trifluoromethylbenzoic acid (5.0 g, 24 mmol), N, O-dimethylhydroxylamine hydrochloride (3.4 g, 35 mmol), oxalyl chloride (2.18 mL, 25 MMOL)] and 6 mL of pyridine to give the title compound (6.0 g) as an oil. Used as is in the next prep 1H NMR (DMSO-d6) : δ 3.28 (s, 3H), 3.475 (s, 3H), 7.499 (t, 1H),] 7.86 (m, 2H). MS [(EI)] [M/Z] : 251 [M+]
  • 2
  • [ 115029-22-6 ]
  • methyl 2-fluoro-3-(trifluoromethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.a 3-(2-Aminoethoxy)-7-trifluoromethyl-1,2-benzisoxazole hydrochloride (a) 2-Fluoro-3-trifluoromethylbenzoic acid methyl ester. The title compound was obtained as an oil from 2-fluoro-3-trifluoromethylbenzoic acid by similar reactions and treatments as in Example 52(a). NMR spectrum (CDCl3)δppm: 3.96(3H,s), 7.31(1H,t,J=5.0 Hz), 7.79(1H,t,J=5.0 Hz), 8.18(1H,t,J=5.0 Hz).
  • 3
  • [ 115029-22-6 ]
  • [ 164341-19-9 ]
YieldReaction ConditionsOperation in experiment
2 EXAMPLE 2 EXAMPLE 2 2-Fluoro-3-trifluoromethylbenzoylguanidine hydrochloride: colorless crystals, vitreous from 2-fluoro-3-trifluoromethylbenzoic acid in accordance with variant B
  • 4
  • [ 115029-22-6 ]
  • [ 57260-71-6 ]
  • [ 885328-05-2 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 4h; 3.1 (1) Synthesis of tert-butyl 4-(2-fluoro-3-(trifluoromethyl)benzoyl)piperazine-l-carboxylate; A mixture of 3.66 g of 1-Boc-piperazine, 4.53 g of l-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride, 3.61 g of 1-hydroxybenzotriazole, 4.50 g of 2-fluoro-3- (trifluoromethyl)benzoic acid and 40 ml of chloroform was stirred at room temperature for 4 hours. The reaction mixture was diluted with chloroform and then was washed with water and brine. The resulting organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate = 4/1 to 2/1) to give the title compound.
  • 6
  • [ 115029-22-6 ]
  • [ 208173-19-7 ]
YieldReaction ConditionsOperation in experiment
99% With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1.5h; Inert atmosphere; 2-fluoro-3-(trifluoromethyl)benzoyl chloride 2-fluoro-3-(trifluoromethyl)benzoyl chloride Oxalyl chloride (0.488 mL, 5.76 mmol) was added to a suspension of 2-fluoro-3-(trifluoromethyl)benzoic acid (1.00 g, 4.81 mmol) in DCM (10 mL) containing catalytic DMF. The reaction was stirred at room temperature for 90 minutes and solvents were removed in vacuo to afford the desired compound (1.08 g, 99%). The product was used without additional purification.
93.7% With thionyl chloride at 90℃; for 3h; 1.1.b; 2.1.b b. Add 1.5g of compound B to 15mL of thionyl chloride, and react under reflux at 90°C. After compound B is completely dissolved, continue to heat and stir for 5h, and then concentrate under reduced pressure to dryness to obtain 1.53g of compound C, namely 2- Fluoro-3-trifluoromethylbenzoyl chloride, with a yield of 93.7% and a purity of 94.2%.
With oxalyl dichloride In dichloromethane at 0 - 25℃; for 2.5h;
With thionyl chloride In dichloromethane for 6h; Reflux;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 4h; Reflux;
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;
With thionyl chloride for 2h; Reflux;
3.03 g With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; 5.3. General method for preparing of analogs 6a-o General procedure: Analogs 6a-o were synthesized as outlined in Scheme 1: Acid(1.2 eq) was dissolved in anhydrous DCM, oxalyl chloride (1.44eq) was added dropwise at 0°C and then one drop DMF was added.The reaction mixture stirred at room temperature for 2 h. The excess oxalyl chloride was removed under reduced pressure, andthe residue dissolved in THF for next transformation.Intermediate 5 (1eq) and triethylamine (1.5 eq) were added sequent to a 25 ml three-neck-bottom flask under a nitrogen atmosphere. Acyl chloride in THF was added dropwise to flask at 0°C.The reaction mixture was stirred at 0°C. After pale yellow solid appeared, the mixture reacted at room temperature until TLC showed 5 disappeared. Ice water was added to reaction mixtureat 0°C, and stirred for another 30 min until no insoluble solid generated.The solid was filtered to get crude product. The crude product further purified by medium pressure column chromatography(C18 padding, ACN: H2O (containing 0.05% TFA) =1:99-99:1) to getproduct as a solid.

Reference: [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2014/275120, 2014, A1 Location in patent: Paragraph 0403; 0404
[2]Current Patent Assignee: ALI CHEMICAL CHANGZHOU CO LTD - CN112624911, 2021, A Location in patent: Paragraph 0018-0019; 0030-0031
[3]Sedinkin, Sergey L.; Rath, Nigam P.; Bauer, Eike B. [Journal of Organometallic Chemistry, 2008, vol. 693, # 18, p. 3081 - 3091]
[4]Location in patent: experimental part Bernotas, Ronald C.; Singhaus, Robert R.; Kaufman, David H.; Ullrich, John; Fletcher III, Horace; Quinet, Elaine; Nambi, Ponnal; Unwalla, Rayomand; Wilhelmsson, Anna; Goos-Nilsson, Annika; Farnegardh, Mathias; Wrobel, Jay [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1663 - 1670]
[5]Location in patent: experimental part Wrobel, Jay; Steffan, Robert; Bowen, S. Marc; Magolda, Ronald; Matelan, Edward; Unwalla, Rayomand; Basso, Michael; Clerin, Valerie; Gardell, Stephen J.; Nambi, Ponnal; Quinet, Elaine; Reminick, Jason I.; Vlasuk, George P.; Wang, Shuguang; Feingold, Irene; Huselton, Christine; Bonn, Tomas; Farnegardh, Mathias; Hansson, Tomas; Nilsson, Annika Goos; Wilhelmsson, Anna; Zamaratski, Edouard; Evans, Mark J. [Journal of Medicinal Chemistry, 2008, vol. 51, # 22, p. 7161 - 7168]
[6]Location in patent: experimental part Hu, Baihua; Unwalla, Raymound; Collini, Michael; Quinet, Elaine; Feingold, Irene; Goos-Nilsson, Annika; Wihelmsson, Anna; Nambi, Ponnal; Wrobel, Jay [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 10, p. 3519 - 3527]
[7]Location in patent: experimental part Shen, Hong C.; Ding, Fa-Xiang; Deng, Qiaolin; Xu, Suoyu; Tong, Xinchun; Zhang, Xiaoping; Chen, Yuli; Zhou, Gaochao; Pai, Lee-Yuh; Alonso-Galicia, Magdalena; Roy, Sophie; Zhang, Bei; Tata, James R.; Berger, Joel P.; Colletti, Steven L. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 19, p. 5716 - 5721]
[8]Zhang, Chun-Hui; Chen, Kai; Jiao, Yan; Li, Lin-Li; Li, Ya-Ping; Zhang, Rong-Jie; Zheng, Ming-Wu; Zhong, Lei; Huang, Shen-Zhen; Song, Chun-Li; Lin, Wan-Ting; Yang, Jiao; Xiang, Rong; Peng, Bing; Han, Jun-Hong; Lu, Guang-Wen; Wei, Yu-Quan; Yang, Sheng-Yong [Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9788 - 9805]
[9]Chrovian, Christa C.; Soyode-Johnson, Akinola; Peterson, Alexander A.; Gelin, Christine F.; Deng, Xiaohu; Dvorak, Curt A.; Carruthers, Nicholas I.; Lord, Brian; Fraser, Ian; Aluisio, Leah; Coe, Kevin J.; Scott, Brian; Koudriakova, Tatiana; Schoetens, Freddy; Sepassi, Kia; Gallacher, David J.; Bhattacharya, Anindya; Letavic, Michael A. [Journal of Medicinal Chemistry, 2018, vol. 61, # 1, p. 207 - 223]
[10]Hou, Weijie; Ren, Yan; Zhang, Zhenhua; Sun, Huan; Ma, Yongfen; Yan, Bo [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1740 - 1750]
YieldReaction ConditionsOperation in experiment
Oakwood Products, Inc., 1741 Old Dunbar Road, West Columbia, S.C. 29172, USA. TCI America, 9211 N. Harborgate Street, Portland, Oreg. 97203, USA ... 2-fluoro-6-nitrobenzoic acid; 3-fluoro-4-nitrobenzoic acid; 4-fluoro-3-nitrobenzoic acid; 5-fluoro-2-nitrobenzoic acid; 2-fluoro-3-(trifluoromethyl)benzoic acid; 4-fluoro-3-(trifluoromethyl)benzoic acid; 5-fluoro-2-(trifluoromethyl)benzoic acid; 2-hydroxy-3-isopropyl-benzoic acid; ...
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 4h; Intermediate 12: 2-Chloro-3-(trifluoromethyl)benzoyl chloride General procedure: Intermediate 12: 2-Chloro-3-(trifluoromethyl)benzoyl chloride To a suspension of 2-chloro-3-(trifluoromethyl)benzoic acid (15 g, 67 mmol) and catalytic DMF (0.06 mL, 0.67 mmol) in DCM (150 mL) was added oxalyl chloride (6.8 mL, 80 mmol) dropwise. The reaction was let stir (vigorous bubbling) for 4 h and concentrated to an oily solid which became solid after overnight drying on high vacuum.
  • 9
  • [ 115029-22-6 ]
  • [ 951895-34-4 ]
  • [ 1244694-56-1 ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide for 24h;
  • 10
  • [ 115029-22-6 ]
  • 2-[1-allyl-7-trifluoromethyl-1H-indazol-3-yl]-4-methoxyphenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 1 h / 20 °C 2.1: 8 h / 20 °C 3.1: tetrahydrofuran / 2 h / 0 °C 4.1: pyridine; hydrazine / 1 h / 100 °C / Microwave irradiation 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 - 60 °C 5.2: 4 h / 60 °C 6.1: boron tribromide / dichloromethane; cyclohexane / 5 h / -30 - 20 °C
  • 11
  • [ 115029-22-6 ]
  • [ 680610-69-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4-methyl-morpholine / tetrahydrofuran / 1 h / 20 °C 2: 8 h / 20 °C 3: tetrahydrofuran / 2 h / 0 °C
  • 12
  • [ 115029-22-6 ]
  • [ 1227290-31-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4-methyl-morpholine / tetrahydrofuran / 1 h / 20 °C 2: 8 h / 20 °C 3: tetrahydrofuran / 2 h / 0 °C
  • 13
  • [ 115029-22-6 ]
  • [ 875795-86-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 4-methyl-morpholine / tetrahydrofuran / 1 h / 20 °C 2: 8 h / 20 °C 3: tetrahydrofuran / 2 h / 0 °C 4: pyridine; hydrazine / 1 h / 100 °C / Microwave irradiation
  • 14
  • [ 115029-22-6 ]
  • [ 1227290-32-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 4-methyl-morpholine / tetrahydrofuran / 1 h / 20 °C 2: 8 h / 20 °C 3: tetrahydrofuran / 2 h / 0 °C 4: pyridine; hydrazine / 1 h / 100 °C / Microwave irradiation
  • 15
  • [ 115029-22-6 ]
  • [ 680611-86-3 ]
  • [ 680612-08-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 1 h / 20 °C 2.1: 8 h / 20 °C 3.1: tetrahydrofuran / 2 h / 0 °C 4.1: pyridine; hydrazine / 1 h / 100 °C / Microwave irradiation 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 - 60 °C 5.2: 4 h / 60 °C
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