[ CAS No. 26074-52-2 ] {[proInfo.proName]}

Name: 26074-52-2|2-Bromobutanoyl bromide|98%
Brand: Ambeed
SKU: A613707
Rating: 92 (26 reviews)

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Quality Control of [ 26074-52-2 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 26074-52-2 ]

CAS No. :	26074-52-2	MDL No. :	MFCD00000154
Formula :	C₄H₆Br₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HHKDBXNYWNUHPL-UHFFFAOYSA-N
M.W :	229.90	Pubchem ID :	117293
Synonyms :

Safety of [ 26074-52-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501	UN#:	3265
Hazard Statements:	H290-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 26074-52-2 ]

* 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.

Upstream synthesis route of [ 26074-52-2 ]
Downstream synthetic route of [ 26074-52-2 ]

[ 26074-52-2 ] Synthesis Path-Upstream 1~1

1
[ 64-17-5 ]
[ 26074-52-2 ]
[ 533-68-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 8, p. 2827 - 2836
[2] Asian Journal of Chemistry, 2012, vol. 24, # 2, p. 929 - 930

[ 26074-52-2 ] Synthesis Path-Downstream 1~19

1
[ 26074-52-2 ]
[ 5398-24-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With ammonium hydroxide at -10℃;
	With ammonia; benzene
	With ammonia

With ammonia; triethylamine In dichloromethane at 0 - 20℃; for 0.5h;

Reference： [1]Yamazaki; Harada; Matsuzaki; et al. [Chemical and Pharmaceutical Bulletin, 1987, vol. 35, # 6, p. 2243 - 2253]
[2]Bischoff [Chemische Berichte, 1897, vol. 30, p. 2312]
[3]Klarmann [Journal of the American Chemical Society, 1926, vol. 48, p. 2366]
[4]Chang, Xihao; Zhang, Qinglin; Guo, Chang [Organic Letters, 2019, vol. 21, # 12, p. 4915 - 4918]

2
[ 26074-52-2 ]
[ 706-03-6 ]
[ 131792-99-9 ]

Yield	Reaction Conditions	Operation in experiment
104 %	With dmap; triethylamine In dichloromethane at 0℃;

Reference： [1]Beard, Richard L.; Meyers, A. I. [Journal of Organic Chemistry, 1991, vol. 56, # 6, p. 2091 - 2096]

3
[ 26074-52-2 ]
[ 4358-87-6 ]
2-Bromo-butyric acid methoxycarbonyl-phenyl-methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With pyridine In diethyl ether at 0℃;

Reference： [1]Landi Jr.; Garofalo; Ramig [Tetrahedron Letters, 1993, vol. 34, # 2, p. 277 - 280]

4
[ 26074-52-2 ]
[ 17583-40-3 ]
[ 106874-96-8 ]

Reference： [1]Tetrahedron,1986,vol. 42,p. 3689 - 3696

5
[ 26074-52-2 ]
[ 6038-19-3 ]
2-Bromo-N-(2-oxo-tetrahydro-thiophen-3-yl)-butyramide [ No CAS ]

Reference： [1]Farmaco, Edizione Scientifica,1986,vol. 41,p. 69 - 79

7
[ 7321-93-9 ]
[ 26074-52-2 ]
[ 873553-95-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In diethyl ether; at 0℃; for 2h;	10 g 4,6-dichloro-pyridin-3-yl-amine were dissolved in 200 mL ether and combined with a solution of 20 g (0.14 mol) potassium carbonate. At 0° C. 15 mL (0.11 mol) 2-bromobutyryl bromide were added dropwise within two hours, during which time a solid formed. The reaction mixture was diluted with 200 mL ethyl acetate, the organic phase was dried over Na2SO4 and evaporated down. The solid obtained was washed with ether. Yield: 14.5 g of a compound X3f (colourless solid)
150 g	With potassium carbonate; In diethyl ether; at 0℃;	In 0 °C, will 260ml2- bromine Ding added to the solution slowly acyl bromide 194g5-amino -2,4- two chloropyridine (CAS-No. 7321-93-9) and 388g potassium carbonate in 3.88l in ether in the suspension. The mixture is filtered, and the filter cake washing with ethyl ether. The filter cake is dissolved in methylene chloride, and the generated water and a solution of saturated sodium chloride solution. The organic phase is dried by sodium sulfate and concentrated in a vacuum. The residue with hexane, stirring, pumping the filtered again, and drying in a vacuum. Get 150g2-bromo-N-(4,6-dichloro-3-pyridyl) d amide.

Reference： [1]Patent: US2006/9457,2006,A1 .Location in patent: Page/Page column 10
[2]Patent: CN105555786,2016,A .Location in patent: Paragraph 0258

8
[ 934-34-9 ]
[ 26074-52-2 ]
[ 866948-60-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	In dichloromethane at 0℃; for 37h; Heating / reflux;	2 Aluminum chloride (7.00 g, 49.5 mmol) and 2-benzothiazolone (2.5 g, 16.5 mmol) were suspended in methylene chloride (65 mL), and α-bromobutyryl bromide (4.00 mL, 33.1 mmol) was dropped thereto with stirring under ice-cooling. The reaction mixture was stirred for 37 hours under heating to reflux, and then the reaction solution was poured into ice-water. The precipitated white crystals were filtered to give 6-(2-bromobutyryl)benzothiazol-2(3H)-one (3.13 g, 63.0%). 1H-NMR (DMSO-d6/500 MHz) δ (ppm): 1.01 (3H, t, J = 7.3 Hz),1.93-2.19 (2H, m), 5.61 (1H, d, J = 7.9 Hz), 7.24 (1H, d, J = 8.5 Hz), 7.99 (1H, dd, J = 1.8, 8.5 Hz), 8.34 (1H, d, J = 1.8Hz), 12.34 (1H, brs).

Reference： [1]Current Patent Assignee: Kyowa Kirin (in: Kirin Holdings); KIRIN HOLDINGS CO., LTD. - EP1736474, 2006, A1 Location in patent: Page/Page column 44

9
[ 26074-52-2 ]
[ 41458-65-5 ]
[ 944356-57-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In water; ethyl acetate at 1 - 40℃;	87.1 step 1 Production of 2-bromo-N-(2-hydroxy-3,5-dimethylphenyl)butylamide 2-Amino-4,6-dimethylphenol (1.5 g) was dissolved by adding ethyl acetate (15 mL) and water (15 mL), sodium hydrogencarbonate (1.84 g) and 2-bromobutyrylbromide (1.59 mL) were added at room temperature, and the mixture was stirred at room temperature. The reaction mixture was partitioned, and the obtained ethyl acetate layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give the title compound (2.81 g) as a brown oil.

Reference： [1]Current Patent Assignee: JAPAN TOBACCO INC - US2007/197512, 2007, A1 Location in patent: Page/Page column 81

10
[ 26074-52-2 ]
[ 55185-77-8 ]
[ 1064666-87-0 ]

Yield	Reaction Conditions	Operation in experiment
69%	With pyridine In acetonitrile at 20℃;

Reference： [1]Kulikova; Ezhova; Kravchenko; Dorofeeva; Kulikov; Zavozin [Russian Chemical Bulletin, 2007, vol. 56, # 8, p. 1631 - 1636]

11
[ 496-15-1 ]
[ 26074-52-2 ]
[ 1119450-42-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;

Reference： [1]Lundin, Pamela M.; Fu, Gregory C. [Journal of the American Chemical Society, 2010, vol. 132, # 32, p. 11027 - 11029]

12
[ 26074-52-2 ]
[ 609-08-5 ]
C₁₂H₁₉BrO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: Diethyl methylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.33333h; Inert atmosphere; Stage #2: 2-bromo-butyryl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 17h; Inert atmosphere;	4.2.1. Alpha bromo ketone 11. NaH (60% in mineral oil, 7.0 g, 0.29 mol) was suspended in THF (265 mL) and cooled to 0°C. Diethyl methylmalonate (27.1 mL, 0.159 mol) was added in smallportions over 50 min while H2 gas evolved. The reaction was warmed to room temperature, stirred at that temperature for 30 min, then it was cooled to 0°C. 2-Bromobutyryl bromide(21.1 mL, 0.175 mol) was added and the reaction was allowed to warm to room temperature. The solution became cloudy as NaBr crashed out. After stirring for 17 h, the reaction mixture was filtered through Celite three times, and then silica gel once to provide bromo ketone 11 as a yellow oil (51.9 g, quant. yield).1H NMR (400 MHz; CDCl3): d 4.68 (dd, J9.0, 4.9 Hz, 1H),4.27e4.17 (m, 4H), 2.05e1.99 (m, 2H), 1.67 (s, 3H), 1.26 (dt, J15.3,7.1 Hz, 6H), 1.04 (t, J7.3 Hz, 3H);13C NMR (101 MHz, CDCl3):d 195.86, 168.47, 167.59, 66.32, 62.73, 62.33, 51.17, 26.96, 18.03,13.83, 13.78, 11.81; FTIR (thin lm): 2981, 2940, 2908, 2879, 1719,1449, 1380, 1256, 1110, 1014 cm1; HRMS (ESI) m/z calcd forC12H20BrO5 [MH]: 323.0494, found: 323.0493.

Reference： [1]Dhanjee, Heemal H.; Haley, Matthew W.; McMahon, Travis C.; Buergler, Jonas F.; Howell, Jennifer M.; Kobayashi, Yutaka; Fujiwara, Koichi; Wood, John L. [Tetrahedron, 2016, vol. 72, # 26, p. 3673 - 3677]

13
[ 26074-52-2 ]
[ 454-82-0 ]
2-bromo-N-[2-hydroxy-4-(trifluoromethyl)phenyl]butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		Preparation 82 2-bromo-N-[2-hydroxy-4-(trifluoromethyl)phenyl]butanamide In a 250 mL round-bottomed flask, 2.5 g of 2-hydroxy-4-(triflouromethyl)aniline (14.11 mmol; 1 eq) were dissolved in 25 mL of DCM, 1.96 mL of Et3N (14.11 mmol; 1 eq) were added and the medium was placed at 0 C. 1.72 mL of 2-bromobutyric acid bromide (14.11 mmol; 1 eq) were added dropwise and the reaction mixture was stirred at 0 C. for 4 h. The mixture was taken up in DCM. The organic phase was washed with a 1N HCl solution, then with a saturated NaHCO2 solution, then with water, and was then dried over MgSO4, filtered and concentrated under reduced pressure. The medium was taken up in 25 mL of THF and then 80 mg of LiOH (3.53 mmol; 0.25 eq) and 12.5 mL of water were added. The medium was stirred overnight at room temperature. The mixture was taken up in DCM, the aqueous phase was acidified to pH 1 and extracted with DCM. The organic phases were combined, washed with a saturated NaCl solution, dried over MgSO4, filtered and concentrated under vacuum. The solid obtained was washed with cyclohexane to give 3.44 g of title compound in the form of a beige solid. The compound was used directly in the following cyclization step Yld: 74%. ?H NMR (300 MHz, DMSO-d-5) oeppm 0.95 (t, J=7.2 Hz, 3H) 1.85-2.16 (m, 2H) 4.94 (t, J=7.1 Hz, 1H) 7.0 7.23 (m, 2H) 8.20 (d, J=8.3 Hz, 1H) 9.74 (brs, 1H) 10.75 (s, 1H). EC-MS: mlz (m+H): 326.

Reference： [1]Patent: US2017/66717,2017,A1 .Location in patent: Paragraph 0959-0962

14
[ 26074-52-2 ]
[ 22864-65-9 ]
2-bromo-N-methyl-N-(4-(trifluoromethyl)phenyl)butanamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1754 - 1758
Angew. Chem.,2019,vol. 131,p. 1768 - 1772,5

15
[ 26074-52-2 ]
[ 101-16-6 ]
2-bromo-N-(3-methoxyphenyl)-N-phenylbutanamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1754 - 1758
Angew. Chem.,2019,vol. 131,p. 1768 - 1772,5

16
[ 26074-52-2 ]
[ 15307-93-4 ]
2-bromo-N-(2,6-dichlorophenyl)-N-phenylbutanamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1754 - 1758
Angew. Chem.,2019,vol. 131,p. 1768 - 1772,5

17
[ 26074-52-2 ]
[ 74-89-5 ]
[ 42275-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0 - 20℃; for 0.5h;

Reference： [1]Chang, Xihao; Zhang, Qinglin; Guo, Chang [Organic Letters, 2019, vol. 21, # 12, p. 4915 - 4918]

18
[ 26074-52-2 ]
[ 109-73-9 ]
[ 1119452-98-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0 - 20℃; for 0.5h;

Reference： [1]Chang, Xihao; Zhang, Qinglin; Guo, Chang [Organic Letters, 2019, vol. 21, # 12, p. 4915 - 4918]

19
[ 26074-52-2 ]
[ 33069-62-4 ]
C₅₁H₅₆BrNO₁₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium hydrogencarbonate In dichloromethane; water at 20℃; for 1h;	3 The reaction formula is as follows: In a three-necked flask, dissolve the compound of formula IV, paclitaxel (200 mg, 0.23 mmol) in a mixed solvent of dichloromethane and water (CH2Cl2 (V): H2O (V) = 1: 1), and add potassium bicarbonate ( 42mg, 0.2mmol), 2-bromobutyryl bromide (60mg, 0.28mmol) was added at room temperature, stirred for 1 hour, the reaction was complete by TLC.The reaction solution was washed twice with 1N HCl (35 ml), washed twice with 1% NaHCO3 (35 ml) and dried with Na2SO3.After evaporating the solvent, the solid was dissolved by heating with EtOAc, and crystallized. Filtration gave compound III-c as a light brown solid (191 mg, 71% yield).Compound III-c was directly dissolved in anhydrous acetonitrile, and trifluoromethyl selenium silver salt (Ag (bpy) (SeCF3) 2) 2 (52 mg, 0.23 mmol) was added in portions, and stirred at room temperature for 24 hours.After the reaction solution was concentrated, it was dropped into 150 ml of water, the resulting solid was filtered, and plate chromatography was performed using 5% CH3OH / CH2Cl2 as a developing agent, and finally a white solid compound I-c (140 mg, yield 60%) was obtained.

Reference： [1]Current Patent Assignee: SHENZHEN FUSHAN BIOTECHNOLOGY - CN110862410, 2020, A Location in patent: Paragraph 0089-0092

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 26074-52-2 ] {[proInfo.proName]}

Quality Control of [ 26074-52-2 ]

Related Doc. of [ 26074-52-2 ]

Product Details of [ 26074-52-2 ]

Safety of [ 26074-52-2 ]

Application In Synthesis of [ 26074-52-2 ]

[ 26074-52-2 ] Synthesis Path-Upstream 1~1

[ 26074-52-2 ] Synthesis Path-Downstream 1~19

Related Functional Groups of [ 26074-52-2 ]

Aliphatic Chain Hydrocarbons

Bromides

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Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 26074-52-2 ]