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[ CAS No. 565-74-2 ]

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Chemical Structure| 565-74-2
Chemical Structure| 565-74-2
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Product Details of [ 565-74-2 ]

CAS No. :565-74-2 MDL No. :MFCD00004210
Formula : C5H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :181.03 g/mol Pubchem ID :-
Synonyms :

Safety of [ 565-74-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P362+P364-P405-P501 UN#:3261
Hazard Statements:H302+H312-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 565-74-2 ]

  • Downstream synthetic route of [ 565-74-2 ]

[ 565-74-2 ] Synthesis Path-Downstream   1~16

  • 2
  • [ 64-17-5 ]
  • [ 10323-40-7 ]
  • [ 609-12-1 ]
YieldReaction ConditionsOperation in experiment
55% With sulfuric acid; for 36h;Heating / reflux; A. Synthesis of 6-(3,5-dimethylbenzyl)-5-isopropyluracil (Compound of the Formula VI according to the Reaction Scheme 1 in which R1 is an isopropyl group and each of R2 is a methyl group)To a solution of 2-bromo-3-methylbutanoic acid (3 g, 16.5 mmol) in ethanol (200 ml), was added concentrated sulfuric acid (4 ml). After 36 h under reflux ebullition, the reaction medium, returned to ambient temperature, was neutralized with an aqueous saturated sodium carbonate solution. After distillation of the ethanol, the reaction medium was extracted with dichloromethane (100 ml). The organic phase was dried over magnesium sulfate and the solvent was evaporated to give ethyl 2-bromo-3-methylbutanoate (1.91 g, 55%).A suspension of Zn powder (31.5 g, 0.48 mol) in tetrahydrofuran (300 ml) was boiled under reflux, and then it was added thereto a few drops of ethyl 2-bromo-3-methylbutanoate to initiate the reaction. After 45 mn under reflux and under magnetic stirring, it was added thereto 3,5-dimethylphenylethanenitrile (13.2 g, 91 mmol), and then, dropwise, the remainder of ethyl 2-bromo-3-methylbutanoate (in total 19.1 g, 91 mmol). The ebullition was maintained for 15 mn, the mixture was then cooled, and then it was added thereto tetrahydrofuran (500 ml) and a 50% aqueous potassium carbonate solution (100 ml). After 45 mn under vigorous stirring, the organic phase was separated by decantation and the aqueous phase was washed with tetrahydrofuran (2×100 ml). The collected organic phases were treated with 10% aqueous hydrochloric acid solution (300 ml) for 45 mn. After elimination of tetrahydrofuran by distillation under reduced pressure, the residue was taken again with dichloromethane (300 ml), and the organic phase was washed with a saturated sodium monohydrogenocarbonate solution (100 ml), dried over magnesium sulfate and concentrated. The distillation of the residue (134 C., 10-1 mmHg) gave ethyl 3-methyl-2-(3,5-dimethylphenylacetyl)butanoate (13.2 g, 52%).Metal sodium (23.8 g, 1.034 mol) was reacted with anhydrous ethanol (500 ml). To the clear obtained solution, was added thiourea (54.35 g, 714 mmol) and ethyl 3-methyl-2(3,5-dimethylphenylacetyl)butanoate (13.14 g, 47.6 mol). The reaction medium was maintained under reflux for 6 h, and then was concentrated in vacuo at 40.50 C. To the obtained residue was added concentrated hydrochloric acid (100 ml) and then the solution was brought to pH 4 with acetic acid. The obtained 6-dimethylbenzyl-5-isopropyl-2-thiouracil was dissolved in an aqueous 10% chloroacetic acid solution (200 ml) and the solution was maintained under reflux for 24 h and then cooled to ambient temperature and the obtained precipitates were separated by filtration and washed with cold ethanol and then with ether, and then dried in vacuo at 40 C. to give 6-(3,5-dimethylbenzyl)-5-isopropyluracil (7 g, 54%). Melting point: 213-214 C.
  • 3
  • [ 565-74-2 ]
  • 2-bromoisovaleryl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride for 2h; Cooling with ice; Reflux; 31.b4 Step b4: Preparation of 2-bromo-3-methylbutyryl chloride: 2-Bromo-3-methylbutyric acid (1.6 g, 8.83 mmol) was placed in a round bottom flask.Place in an ice water bath for 5 min. 10 mL of thionyl chloride was slowly added dropwise, and the reaction was refluxed for 2 h.The thionyl chloride solution was rotated to give 1.56 g (100%) of 2-bromo-3-methylbutyryl chloride.
With thionyl chloride at 20 - 60℃; unter allmaehlicher Steigerung der Temperatur;
With trichloroacetonitrile; triphenylphosphine In dichloromethane at 20℃; for 4h;
With trichloroacetonitrile; triphenylphosphine In acetonitrile at 20℃;
With thionyl chloride for 1.5h; Heating;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;
With thionyl chloride V EXAMPLE V EXAMPLE V 50g of 2-bromoisovaleric acid was mixed with 80 ml of thionylchloride and the mixture was refluxed for 4 hours to give 45.9g of 2-bromoisovaleryl chloride. (b.p. 68° - 70°C/29 mmHg)
With thionyl chloride for 2h; Heating;
With sulfuryl dichloride
With oxalyl dichloride In dichloromethane at 20℃; for 16h; 17; 10 To a solution of 2-bromo-3 -methyl butanoic acid (1.07 g, 5.91 mmol) in anhydrous CH2Cl2 (10 mL), a droplet of DMF and oxalyl chloride (1.5 mL, 17 mmol) were added at room temperature under nitrogen atmosphere. After stirring for 16 h, the reaction mixture was concentrated under reduced pressure and azeotroped with toluene. To the obtained residue, 3-amino-5-bromobenzofuran-2-carboxamide (1, 186 mg, 0.73 mmol) and chloroform were added. The mixture was heated to 40 0C for 3 h. The mixture was poured over aqueous saturated NaHCO3 (120 mL) and the organic phase was separated. The aqueous layer was further extracted with CHCl3 (2x 80 mL) . The combined organic layers were dried over MgSO4, then concentrated in vacuo. After purification by flash chromatography (91 :8:1 dichloromethane/methanol/28% (w/w) ammonium hydroxide), the title compound was obtained as an oil (198 mg), 65% yield. 1H NMR (400 MHz, CDCl3) δ 10.64 (br s, IH), 8.66 (d, J= 3 Hz, IH), 7.56 (dd, J= 3, J= 9 Hz, IH), 7.31 (d, J= 9 Hz, IH), 6.41 (br s, IH), 5.80 (br s, IH), 4.37 (d, J= 6.5 Hz, IH), 2.46 (sept, J= 6.5 Hz, IH), 1.14 (dd, J= 3, J= 6.5 Hz, IH); 13C NMR (100 MHz, CDCl3) δ 167.3, 162.6, 152.4, 133.0, 131.8, 129.7, 127.9, 123.4, 116.7, 113.4, 59.5, 33.1, 20.9, 19.5; MS (ESI+) for Ci4Hi4Br2N2O3: 419 (MH+).
With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 0 - 20℃; 32.4 Production of 2-amino-6-isopropylphenol hydrobromide Step 4 Production of 2-bromo-3-methylbutyryl chloride Chloroform (200 mL) was added to 2-bromo-3-methylbutyric acid (25 g), and oxalyl chloride (14.5 mL) and N,N-dimethylformamide (3 drops) were added under ice-cooling. After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure, and azeotroped with toluene to give the title compound as a yellow oil.
With oxalyl dichloride In chloroform at 1 - 40℃; 6.1 step 1 Production of 2-bromo-3-methylbutyryl chloride 2-Bromo-3-methylbutyric acid (25 g) was dissolved in chloroform (200 mL), oxalyl chloride (14.5 mL) and N,N-dimethylformamide (three drops) were added. After stirring the mixture overnight at room temperature, the mixture was concentrated, and the residue was azeotroped with chloroform and toluene to give the title compound as a yellow oil.
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Inert atmosphere;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃;
With oxalyl dichloride at 60℃; for 2h;
With thionyl chloride for 2h; Reflux; 4.1.1.1. 2-Bromohexanoyl chloride (36a). General procedure: A flask was charged with2-bromohexanoic acid (1.95 g, 10 mmol) at 0 C and thionyl chloride (10 mL) was added dropwise. The mixture was stirred at rt for 10 min and then heated under reflux for 2 h. The excess thionylchloride was removed by distillation and the resulting acyl chloride was used without any further purification.
With thionyl chloride; N,N-dimethyl-formamide In toluene at 35 - 40℃; for 4h; Inert atmosphere; 1.S1 S1: Synthesis of α-bromoisovaleryl chloride. With a thermometer,Mechanical agitation,In the 2L four-neck bottle of the constant pressure dropping funnel device,Under nitrogen protection,Α- bromo-isovaleric acid was added 100g,Toluene 500ml and 0.1g N,N-dimethylformamide (DMF),Control at 35-40 ° C,69 g of thionyl chloride was added dropwise and stirring was continued for 4 hours.Until the reaction is complete, the tail gas is absorbed by the alkaline water.
With oxalyl dichloride; N,N-dimethyl-formamide In chloroform at 0 - 40℃; 32.4 Step 4 Production of 2-bromo-3-methylbutyryl chloride Chloroform (200 mL) was added to 2-bromo-3-methylbutyric acid (25 g), and oxalyl chloride (14.5 mL) and N,N-dimethylformamide (3 drops) were added under ice-cooling. After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure, and azeotroped with toluene to give the title compound as a yellow oil.

Reference: [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN110092782, 2019, A Location in patent: Paragraph 0174; 0176
[2]Fischer,E.; Schenkel [Justus Liebigs Annalen der Chemie, 1907, vol. 354, p. 13]
[3]Jang, Doo Ok; Park, Doo Jin; Joonggon, Kim [Tetrahedron Letters, 1999, vol. 40, # 29, p. 5323 - 5326]
[4]Jang, Doo Ok; Cho, Dae Hyan; Kim, Joong-Gon [Synthetic Communications, 2003, vol. 33, # 16, p. 2885 - 2890]
[5]St. Jean Jr., David J.; Yuan, Chester; Bercot, Eric A.; Cupples, Rod; Chen, Michelle; Fretland, Jenne; Hale, Clarence; Hungate, Randall W.; Komorowski, Renee; Veniant, Murielle; Wang, Minghan; Zhang, Xiping; Fotsch, Christopher [Journal of Medicinal Chemistry, 2007, vol. 50, # 3, p. 429 - 432]
[6]Sibi, Mukund P; Miyabe, Hideto [Organic letters, 2002, vol. 4, # 20, p. 3435 - 3438]
[7]Current Patent Assignee: SANTEN PHARMACEUTICAL CO LTD - US3971828, 1976, A
[8]Strotman, Neil A.; Sommer, Stefan; Fu, Gregory C. [Angewandte Chemie - International Edition, 2007, vol. 46, # 19, p. 3556 - 3558] Dai, Xing; Strotman, Neil A.; Fu, Gregory C. [Journal of the American Chemical Society, 2008, vol. 130, # 11, p. 3302 - 3303]
[9]Tricarico, Domenico; Mele, Antonietta; Camerino, Giulia Maria; Laghezza, Antonio; Carbonara, Giuseppe; Fracchiolla, Giuseppe; Tortorella, Paolo; Loiodice, Fulvio; Camerino, Diana Conte [Molecular Pharmacology, 2008, vol. 74, # 1, p. 50 - 58]
[10]Current Patent Assignee: EXELIXIS INC - WO2009/86264, 2009, A1 Location in patent: Page/Page column 241
[11]Current Patent Assignee: JAPAN TOBACCO INC - US2007/10670, 2007, A1 Location in patent: Page/Page column 90
[12]Current Patent Assignee: JAPAN TOBACCO INC - US2007/197512, 2007, A1 Location in patent: Page/Page column 43
[13]Location in patent: experimental part Tka, Najeh; Jegham, Nafâa; Ben Hassine, Béchir [Comptes Rendus Chimie, 2010, vol. 13, # 10, p. 1278 - 1283]
[14]Tka, Najeh; Kraem, Jamil; Hassine, Bechir Ben [Synthetic Communications, 2013, vol. 43, # 5, p. 735 - 743]
[15]Bera, Kalisankar; Satam, Nishikant S.; Namboothiri, Irishi N. N. [Journal of Organic Chemistry, 2016, vol. 81, # 13, p. 5670 - 5680]
[16]Xue, Xiaoqian; Zhang, Yan; Wang, Chao; Zhang, Maofeng; Xiang, Qiuping; Wang, Junjian; Wang, Anhui; Li, Chenchang; Zhang, Cheng; Zou, Lingjiao; Wang, Rui; Wu, Shuang; Lu, Yongzhi; Chen, Hongwu; Ding, Ke; Li, Guohui; Xu, Yong [European Journal of Medicinal Chemistry, 2018, vol. 152, p. 542 - 559]
[17]Current Patent Assignee: SUZHOU LAKESTAR PHARMATECH - CN108395387, 2018, A Location in patent: Paragraph 0026; 0028; 0029; 0035; 0036; 0042-0043; 0049-0050
[18]Current Patent Assignee: JAPAN TOBACCO INC - US2008/64871, 2008, A1 Location in patent: Page/Page column 54
  • 8
  • [ 565-74-2 ]
  • [ 18803-44-6 ]
  • [ 140400-37-9 ]
YieldReaction ConditionsOperation in experiment
98% With sodium carbonate In water for 168h; Ambient temperature;
  • 9
  • [ 565-74-2 ]
  • [ 10486-08-5 ]
  • [ 140400-38-0 ]
YieldReaction ConditionsOperation in experiment
81% With sodium carbonate In water for 168h; Ambient temperature;
  • 10
  • [ 565-74-2 ]
  • [ 13457-82-4 ]
  • [ 140400-36-8 ]
YieldReaction ConditionsOperation in experiment
87% With sodium carbonate In water for 168h; Ambient temperature;
  • 11
  • [ 565-74-2 ]
  • [ 54166-35-7 ]
  • [ 140400-39-1 ]
YieldReaction ConditionsOperation in experiment
69% With sodium carbonate In water for 168h; Ambient temperature;
  • 12
  • [ 565-74-2 ]
  • [ 67141-36-0 ]
  • [ 140400-41-5 ]
YieldReaction ConditionsOperation in experiment
90% With sodium carbonate In water for 168h; Ambient temperature;
  • 13
  • [ 565-74-2 ]
  • [ 83119-51-1 ]
  • [ 83119-44-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium hydride 1) DMF, 10 min; 2) room temp., 3 h; Yield given. Multistep reaction;
In <i>N</i>-methyl-acetamide; water 66 EXAMPLE 66 EXAMPLE 66 To 3.13 g of 99% sodium hydride under nitrogen at room temperature is added a solution of 12.26 g of 2,3-dichloro-4-methoxythiophenol in 100 ml of sieve-dried dimethylformamide over 2 minutes. The reaction is stirred for 12 minutes. A solution of 9.56 g of α-bromoisovaleric acid in 85 ml of dimethylformamide is added over 4 minutes. The reaction is stirred at room temperature for 3 hours, cooled in ice, diluted with 500 ml of water and filtered. The solution is cooled and acidified with 3 N hydrochloric acid to give the product. The precipitate is filtered, washed with a small amount of water, dried and recrystallized from acetone-pentane to give 13.14 g of α-(2,3-dichloro-4-methoxyphenylthio)isovaleric acid as a white crystalline powder mp 176.5°-178.5°. ANALYSIS: Calculated for C12 H14 Cl2 O3 S: 46.62%C, 4.57%H; Found: 46.80%C, 4.59%H.
  • 14
  • [ 565-74-2 ]
  • Sodium; 4-ethyl-benzenethiolate [ No CAS ]
  • [ 140400-40-4 ]
YieldReaction ConditionsOperation in experiment
97% With sodium carbonate In water for 168h; Ambient temperature;
  • 15
  • [ 565-74-2 ]
  • [ 81911-88-8 ]
  • [ 140400-42-6 ]
YieldReaction ConditionsOperation in experiment
94% With sodium carbonate In water for 168h; Ambient temperature;
  • 16
  • [ 516-06-3 ]
  • [ 565-74-2 ]
YieldReaction ConditionsOperation in experiment
81% With pyridinium polyhydrogen fluoride; potassium bromide; sodium nitrite for 48h; Ambient temperature;
With sulfuric acid; potassium bromide; sodium nitrite at 0℃;
With hydrogen bromide; potassium bromide; sodium nitrite at -13℃;
With hydrogen bromide; sodium nitrite In water; toluene at 0 - 20℃; for 4h;
Stage #1: D,L-valine With hydrogen bromide In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at 0 - 20℃; for 3.5h; 4.1.2.1. 2-Bromo-4-(methylthio)butanoic acid (35c). General procedure: To a solution ofDL-methionine (3.0 g, 20.1 mmol) in H2O (50 mL) was added 30% HBr (20 mL). The reaction mixture was stirred at 0 C for 10 min. A solution of sodium nitrite (1.7 g, 24 mmol) in H2O (50 mL) was added. The reaction mixture was stirred at 0 C for 30 min and thenwarmed to rt for 3 h. The reaction mixture was extracted withEtOAc (100 mL 3). The organic layer was washed with brine and dried over Na2SO4. The solid was filtered off, and the filtrate was concentrated under reduced pressure to give 3.6 g of intermediate 35c (83% yield).
Stage #1: D,L-valine With hydrogen bromide In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at 0 - 20℃; for 3.5h;

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