[ CAS No. 590-17-0 ] Bromoacetonitrile

Cat. No.: A236062

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2D 3D

Structure of 590-17-0 * Storage: Keep in dark place,Sealed in dry,2-8°C

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* Storage: Keep in dark place,Sealed in dry,2-8°C

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Quality Control of [ 590-17-0 ]

COA NMR CNMR HPLC LC-MS

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Specification

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Product Details of [ 590-17-0 ]

CAS No. :	590-17-0	MDL No. :	MFCD00001884
Formula :	C₂H₂BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	REXUYBKPWIPONM-UHFFFAOYSA-N
M.W :	119.95	Pubchem ID :	11534
Synonyms :		Chemical Name :	2-Bromoacetonitrile

Calculated chemistry of [ 590-17-0 ] Expand+

Safety of [ 590-17-0 ]

Signal Word:	Danger	Class:	6.1(3)
Precautionary Statements:	P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P310+P330-P303+P361+P353-P304+P340+P311-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501	UN#:	3275
Hazard Statements:	H226-H301+H311+H331-H315-H319-H335	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 590-17-0 ]

* 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 [ 590-17-0 ]
Downstream synthetic route of [ 590-17-0 ]

[ 590-17-0 ] Synthesis Path-Upstream 1~2

1
[ 186581-53-3 ]
[ 60-29-7 ]
[ 506-68-3 ]
[ 13273-53-5 ]
[ 16681-67-7 ]
[ 16681-82-6 ]
[ 590-17-0 ]

Reference： [1] Acta Chemica Scandinavica (1947-1973), 1959, vol. 13, p. 888,890

2
[ 142851-03-4 ]
[ 590-17-0 ]
[ 495414-81-8 ]

Yield	Reaction Conditions	Operation in experiment
2.6 g	With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane for 12 h; Cooling with ice	A) 1-tert-butyl 4-ethyl 4-(cyanomethyl)piperidine-1,4-dicarboxylate To a mixture of diisopropylamine (4.7 g) and THF (75 mL) was added n-butyllithium hexane solution (1.6 M, 29 mL) under ice-cooling, and the mixture was stirred for 30 min. To the mixture was added a mixture of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (6.0 g) and THF (10 mL) under ice-cooling, the mixture was stirred under ice-cooling for 3 hr, and 2-bromoacetonitrile (5.6 g) was added thereto under ice-cooling. The mixture was stirred for 12 hr, and the solvent was evaporated under reduced pressure. Water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.6 g). ¹H NMR (300 MHz, DMSO-d₆) δ 1.21 (3H, t, J = 7.0 Hz), 1.39 (9H, s), 1.43-1.54 (2H, m), 1.90-2.00 (2H, m), 2.87 (2H, s), 2.96-3.12 (2H, m), 3.57-3.67 (2H, m), 4.11-4.22 (2H, m).

Reference： [1] Patent: EP2933247, 2015, A1, . Location in patent: Paragraph 0333
[2] Patent: WO2010/130665, 2010, A1, . Location in patent: Page/Page column 136-137

[ 590-17-0 ] Synthesis Path-Downstream 1~21

1
[ 7768-28-7 ]
[ 590-17-0 ]
[ 154582-38-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	potassium carbonate; In acetone;	EXAMPLE 27 2-Hydroxyphenethyl alcohol was reacted with bromoacetonitrile in the presence of potassium carbonate to protect the phenolic oxygen, as in Tetrahedron Letters, 1993, 34, 7567-7568. 2-Hydroxyphenethyl alcohol was dissolved in 20 mL acetone. To this was added 1.2 g potassium carbonate. To the stirring mixture was added 0.87 g bromoacetonitrile under nitrogen. The mixture was stirred overnight. The mixture was filtered, and the filtrate was concentrated. The product was purified by flash column chromatography on silica gel, eluding with 1/1 ethyl acetate:hexanes, to yield 81percent of 2-(o-cyanomethyl)phenethyl alcohol. 1H NMR (CD2Cl2): 2.81 (t, 2H), 3.72 (t, 2H), 4.77 (s, 2H), 6.92 (dd, 2H), 7.18 (d, 2H).
81%	With potassium carbonate; In acetone;	2-Hydroxyphenethyl alcohol was reacted with bromoacetonitrile in the presence of potassium carbonate to protect the phenolic oxygen, as in Tetrahedron Letters,1993, 34, 7567-7568. 2-Hydroxyphenethyl alcohol was dissolved in 20 mL acetone. To this was added 1.2 g potassium carbonate. To the stirring mixture was added 0.87 g bromoacetonitrile under nitrogen. The mixture was stirred overnight. The mixture was filtered, and the filtrate was concentrated. The product was purified by flash column chromatography on silica gel, eluting with 1/1 ethyl acetate:hexanes, to yield 81percent of 2-(o-cyanomethyl)phenethyl alcohol.1H NMR (CD2Cl2): 2.81 (t, 2H), 3.72 (t, 2H), 4.77 (s, 2H), 6.92 (dd, 2H), 7.18 (d, 2H). 2-(o-Cyanomethyl)phenethyl alcohol (1.0 g, 6.3 mmol) was dissolved in 5 mL anhydrous DMF and added to a stirring solution of sodium hydride (0.25g, 10.4 mmol) in DMF (20 mL). After hydrogen evolution ceases, methyl iodide (0.47 mL, 7.5 mmol) was added dropwise. The mixture was stirred at room temperature under nitrogen for five hours. After aqueous workup, the product was purified using flash column chromatography on silica gel, eluting with 1/5 ethyl acetate/hexanes solvent mixture to yield 0.56 g (56percent) of the desired product, 2-(o-cyanomethyl)phenethyl methyl ether. 1H NMR (CD2Cl2): 2.96 (t, 2H), 3.36 (s, 3H), 3.60 (t, 2H), 4.86 (s, 2H), 7.04 (dd, 2H), 7.31 (d, 2H). 2-(o-Cyanomethyl)phenethyl methyl ether was deprotected following the procedure described in Tetrahedron Letters, 1993, 34, 7567-7568. 2-(o-Cyanomethyl)phenethyl methyl (0.56 g, 3.13 mmol) was dissolved in 40 mL anhydrous ethanol. Platinum dioxide (20 mg) was added to this solution. The solution was purged with hydrogen for 10 minutes, and then stirred under hydrogen overnight. The mixture was filtered, and the filtrate was concentrated. The residue was redissolved in ether, washed with water, and dried over MgSO4. After concentration, 0.39 g (82percent) of 2-hydroxyphenethyl methyl ether was isolated. 1H NMR (CD2Cl2): 2.78 (t, 2H), 3.32 (s, 3H), 3.60 (t, 2H), 2-Hydroxyphenethyl methyl ether was reacted with diethylphosphoramidous dichloride to yield the corresponding phosphorous amidite in the same manner as described for Example 25. 31P NMR (toluene): 137 ppm. The phosphoroamidite was treated with 1M HCl solution following the procedure described for Example 25 to yield the corresponding phosphorochloridite. 31P NMR (toluene): 165 ppm. The phosphochloridite was then reacted with di(2-tolyl)-2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylate in the same manner as described for Example 19. 31P NMR (toluene): 125 (major), 127 (minor), 142 (minor).

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 7567 - 7568
[2]Patent: US2003/23110,2003,A1
[3]Patent: EP1214282,2005,B1 .Location in patent: Page/Page column 26

2
[ 6940-80-3 ]
[ 590-17-0 ]
[ 152673-15-9 ]

Reference： [1]Synlett,2003,p. 726 - 728
[2]Organic and Biomolecular Chemistry,2005,vol. 3,p. 3926 - 3936
[3]Synlett,2006,p. 781 - 785

3
[ 6086-21-1 ]
[ 590-17-0 ]
[ 1072788-70-5 ]

Reference： [1]European Journal of Inorganic Chemistry,2007,p. 4965 - 4972

4
[ 380380-60-9 ]
[ 590-17-0 ]
[ 1217273-69-2 ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium hydroxide; In N,N-dimethyl-formamide; at 0 - 20℃;	KOH (1.7 g, 30.6 mmol) was added to a solution of Intermediate 37 (3.46 g, 15.3 mmol) in 35 mL of DMF at 0 C. Then BrCH2CN (3.2 mL, 45.9 mmol) was added dropwise. The mixture was stirred at r.t. o.n. Then 400 mL of ice-water was added and extracted with EtOAc. The organic phase was washed with brine, dried and evaporated. Purification by silica gel column (petroleum ether/EtOAc=1/3) gave 2.1 g of Intermediate 38 (yield 52%).

Reference： [1]Patent: US2010/69441,2010,A1 .Location in patent: Page/Page column 38

5
[ 31560-06-2 ]
[ 590-17-0 ]
[ 1319197-37-9 ]

Yield	Reaction Conditions	Operation in experiment
		Bromoacetonitrile (0.208 mL, 3.12 mmol) was added to a slurry of (lS,4S)-2-oxa- 5-azabicyclo[2.2.1]heptane hydrochloride (0.353 g, 2.60 mmol) , DMSO (13 mL) and MP-carbonate (3.17 mmol/g, 2.5X, 6.5 mmol, 2.05 g). After shaking overnight, 0.52 mmol trisamine (4.17 mmol/g, 125 mg) was added, and the slurry was shaken for an additional 2 h. The slurry was filtered and the resulting 2-((lS,4S)-2-oxa-5- azabicyclo[2.2.1]heptan-5-yl)acetonitrile/DMSO solution was used directly in the next step.

Reference： [1]Patent: WO2011/90911,2011,A1 .Location in patent: Page/Page column 89

6
[ 269410-08-4 ]
[ 590-17-0 ]
[ 1093307-35-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; sodium iodide; In acetonitrile; at 70℃;	A mixture of 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)- lH- pyrazole (0.50 g, 2.58 mmol), sodium iodide (39 mg, 0.26 mmol) bromoacetonitrile (1 .3 g, 10.8 mmol) and potassium carbonate (1.0 g, 7.8 mmol) in acetonitrile (10 mL) was heated at 70 C overnight. Water was added and the solution was extracted with EtOAc (3x). The organic was dried over Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography ( 10% to 100% EtOAc/hexane) to obtain 2-(4-(4,4,5,5-tetramethyl-l ,3,2- dioxaborolan-2-yl)-lH-pyrazol-l-yl)acetonitrile (0.38g, 63% yield). MS (ESI) m/z: 234.1 (M+H+).
39%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 24h;	A solution of 4-(4,4, 5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H- pyrazole (5.11 g, 26.3 mmol) in DMF (50 mL) was treated with bromoacetonitrile (2.20 mL, 31.6 mmol) and K2CO3() (5.46 g, 39.5 mmol). The resulting suspension was stirred for 24 h at 100 C. The reaction mixture was cooled to ambient temperature, diluted with water (100 mL) then extracted with EtOAc (3 x 250 mL). The combined organic extracts were washed with water (3 x 50 mL) and brine (50 mL) then dried over anhydrous Na2SO4(). Following filtration, the organic extracts were concentrated under vacuum then purified by silica chromatography (10-60% Hexanes/EtOAc as the gradient eluent) to afford the title compound (2.42 g, 39% yield). ?H NIVIR (400 MHz, DMSO-d6) 8.04 (s, 1H), 7.71 (s, 1H), 5.49 (s, 2H), 1.25 (s, 12H).
	With potassium carbonate; sodium iodide; In acetonitrile; at 70℃; for 24h;	[00769] Compound 48 was prepared in 2 steps according to the following procedures: 4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-pyrazole (2.61 mmol, 1.0 equiv), bromoacetonitrile (4.2 equiv), sodium iodide (0.1 equiv) and potassium carbonate (3.0 equiv) were suspended in acetonitrile (10 mL) and heated to 70 C for 24h after which the reaction was cooled, partioned between water and brine and extracted with ethyl acetate. The combined organics were concentrated onto silica gel (4g) and purified using flash silica gel chromatography (Silicycle Si-40g, gradient 10-100% ethyl acetate/hexanes) to provide pinacol ester 47.47

Reference： [1]Patent: WO2011/139891,2011,A1 .Location in patent: Page/Page column 61-62
[2]Patent: WO2017/70708,2017,A1 .Location in patent: Paragraph 00405
[3]Patent: WO2015/51241,2015,A1 .Location in patent: Paragraph 00769

7
[ 58863-48-2 ]
[ 590-17-0 ]
[ 37797-72-1 ]
[ 4265-25-2 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

8
[ 51746-85-1 ]
[ 590-17-0 ]
2-(4-(pyridin-3-yl)-1H-imidazol-1-yl)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		A solution of <strong>[51746-85-1]3-(1H-imidazol-4-yl)pyridine</strong> (8.0 g, 55.0 mmol) in tetrahydrofuran (100 mL) was added to a stirred and cooled (0 C.) suspension of NaH (60% dispersion in mineral oil, 3.0 g, 75.0 mmol) in THF (50 mL). Stirring continued for 30 min, and 2-bromoacetonitrile (6.5 g, 55.0 mmol) was added. After addition, the reaction mixture was stirred for 1 h at room temperature and then concentrated by evaporation. The residue was purified by silica gel chromatography (DCM/MeOH=10:1) to give the tile compound (7.5 g, 80% yield).

Reference： [1]Patent: US2015/65522,2015,A1 .Location in patent: Paragraph 0367; 0368

9
[ 5847-59-6 ]
[ 590-17-0 ]
2-(2-bromo-4-nitrophenoxy)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In acetonitrile; at 50℃; for 5h;	To a solution of <strong>[5847-59-6]2-bromo-4-nitrophenol</strong> (40.7 g, 187 mmol), bromoacetonitrile (14.30mL, 205 mmol) in acetonitrile (600 mL) was added potassium carbonate (31.0 g, 224mmol) and the resulting mixture was heated to 50 C for 5 h. The reaction mixture wasconcentrated, dissolved in EtOAc (30 mL) and washed with H20 (30 mL), iN NaOH, and brine. The organic layer was concentrated and the residue was purified by column chromatography (silica gel, 2:8 ethyl acetate: petroleum ether) to obtain the title compound.Yield: 44.02 g (92 %); 1H NMR (300 MHz, DMSO-d6): O 4.98 (5, 2H, CH2), 7.13 (d, 1H,= 9.3 Hz, Ar), 8.29 (dd, 1 H, J1 = 9.3 Hz, J2 = 2.4 Hz, Ar), 8.54 (d, 1 H, J = 2.4 Hz, Ar); MS (El, 70 eV): mlz 252.1 (M+Hj.

Reference： [1]Patent: WO2015/49629,2015,A1 .Location in patent: Page/Page column 135

10
[ 4591-55-3 ]
[ 590-17-0 ]
3,5-di(methoxycarbonyl)-N-(cyanomethyl)pyridinium bromide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 11660 - 11664
Angew. Chem.,2014,vol. 126,p. 11846 - 11850,5

11
[ 114041-16-6 ]
[ 590-17-0 ]
2-(5,6-dimethoxyisoindolin-2-yl)acetonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 934 - 946

12
[ 24410-19-3 ]
[ 590-17-0 ]
2-(4-oxopyrido[2,3-d]pyrimidin-3(4H)-yl)acetonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 2794 - 2809

13
[ 4983-28-2 ]
[ 590-17-0 ]
2-(2-chloropyrimidin-5-yl)oxyacetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.37%	With potassium carbonate; In acetonitrile; at 60℃; for 2h;	To a mixture of bromoacetonitrile (2.94 mL, 42.18 mmol), <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong>(5 g, 38.30 mmol) in CH3CN (100 mL) is added potassium carbonate (7.94 g, 57.45mmol). The reaction mixture is heated to 60 °C for 2 hours. After cooling to roomtemperature, the solid is filtered and the filtrate is concentrated under reduced pressure.The residue is purified by silica gel flash chromatography eluting with a gradient of 100percentether to 1/1 ether/ethyl acetate to give the title compound (6 g, 35.38 mmol, 92.37percent) as awhite solid. Mass spectrum (mlz): 170 (M+H).

Reference： [1]Patent: WO2016/133770,2016,A1 .Location in patent: Page/Page column 4

14
[ 52537-00-5 ]
[ 590-17-0 ]
2-(6-chloroindoline-1-yl)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 19h;	Synthesis of In the N.N-dimethylformamide (3.7 mL) solution of 6-chloro indoline (170 mg, 1.1mmol), bromoacetonitrile (0.12 mL, 1.7mmol) and potassium carbonate (230 mg, 1.7mmol) was added at room temperature followed by stirring for 19 hours at 70 C..The reaction mixture was added water (30 mL) at room temperature, followed by extraction with ethyl acetate (30 mL). The organic layer was dried over sodium sulfate, and concentrated. The resulting concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 25/75) with purified childAnd afforded the 2- (<strong>[52537-00-5]6-chloro-indoline</strong>-1-yl) acetonitrile as a white solid (210 mg, 97% yield).

Reference： [1]Patent: JP2015/193573,2015,A .Location in patent: Paragraph 0044

15
[ 96-81-1 ]
[ 590-17-0 ]
C₉H₁₄N₂O₃ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 5633 - 5636

16
[ 2105-96-6 ]
[ 590-17-0 ]
2-(4-fluoro-3-nitrophenoxy)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 50℃; for 0.5h;	<strong>[2105-96-6]4-<strong>[2105-96-6]fluoro-3-nitrophenol</strong></strong> (933 mg, 5.94 mmol) was dissolved in DMF (11.900 ml) and cesium carbonate (2709 mg, 8.31 mmol) was added at room temperature. Then, 2- bromoacetonitrile (0.496 ml, 7.13 mmol) was added and the reaction stirred at 50 °C. After 30 minutes, the reaction was diluted with water and extracted with EtOAc three times. The organics were combined and washed with half-saturaed aq. NaCl solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give 96A (deep, red oil, 1.12 g, 5.42 mmol, 91 percent yield). MR (400 MHz, chloroform-d) delta: 7.67 (dd, J=6.1, 2.8 Hz, 1H), 7.27-7.36 (m, 2H), 4.84 (s, 2H).

Reference： [1]Patent: WO2016/210414,2016,A1 .Location in patent: Page/Page column 116-117

17
[ 78137-76-5 ]
[ 590-17-0 ]
2-(4-bromo-3-nitrophenoxy)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; for 1.5h;	3.130. Compound 118: (lR,2R)-N-[6-[5-(cyanomethoxy)-2-ethyl-N-methyl-anilino]-l-methyl- imidazo[4,5-c]pyridin-4-yl]-2-fluoro-cyclopropanecarboxamide 3.130.1. Step i): 2-(4-bromo-3-nitro-phenoxy)acetonitrile Bromoacetonitrile (11.5 mmol) is added to a mixture of <strong>[78137-76-5]4-bromo-3-nitrophenol</strong> (9.22 mmol) and K2CO3 in CH3CN (15 mL). The mixture is stirred for 1.5 h. The mixture is concentrated and the residue is partitioned between DCM and sat. NaHCC>3. The two phases are separated and the organic layer is dried (filtered through phase separator) and concentrated to afford the desired product.

Reference： [1]Patent: WO2017/12647,2017,A1 .Location in patent: Paragraph 0716

18
[ 33689-29-1 ]
[ 590-17-0 ]
C₇H₉NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		At 10 C, Methyl 1-hydroxy-1-cyclopropanecarboxylate (50.00 g, 0.43 mol) was added to tetrahydrofuran (400 mL).Nitrogen protection, adding 60% sodium hydride (34.4 g, 0.86 mol) in batches at the same temperature.After the addition was completed at 10 C for 15 minutes, bromoacetonitrile (103.2 g, 0.86 mol) was further added, and the reaction was carried out at 10 C for 15 minutes. Then, water (100 mL) was slowly added dropwise at 0 C, and water (400 mL) was added.The aqueous phase was extracted with ethyl acetate (200 mL*2), and the organic phase was combined, and the organic phase was washed with saturated brine (100 mL).Concentrated organic phase,Sand column chromatography (petroleum ether: ethyl acetate = 4:1 to 3:1)Get 61.3g of light yellow liquid,That is, Intermediate 1, the yield was 92%.

Reference： [1]Patent: CN108530375,2018,A .Location in patent: Paragraph 0052; 0053; 0054; 0055

19
[ 1196473-37-6 ]
[ 590-17-0 ]
2-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)oxy)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%		Toa solution of <strong>[1196473-37-6]benzo[c][1,2]oxaborole-1,6(3H)-diol</strong> (2 g, 13.34 mmol) inN,N-dimethylformamide (20 mL) was added NaH (1.60 g, 66.7 mmol) at 0 °C. After stirring for 1 h, 2-bromoacetonitrile(1.92 g, 16.01 mmol) was added. The mixture was stirred for 12 hours at roomtemperature. The mixture was dilutedwith water (20 mL), acidified to pH 3 with 1 N aqueous HCl solution, and extractedwith ethyl acetate (3 x 20 mL). Theorganic phase was washed with brine, dried over anhydrous Na2SO4,concentrated, and purified by silica gel chromatography using petroleum ether ?ethyl acetate (5:1) to give2-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)oxy)acetonitrile (1.7 g, 67percent yield) as a brown oil. LCMS: [M+H]+: 190.1.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3676 - 3680

20
[ 619-60-3 ]
[ 590-17-0 ]
C₁₀H₁₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 3h;	General procedure: To a stirred solution of 24b-f (1.0 mmol) in anhydrous EtOH was added 4-methylbenzenesulfonate, pyridin-1-ium (PPTS) (300.0 mg,1.2 mmol), and refluxed overnight. The mixture was concentrated to give crude 25b-j which was used for the next step directly withoutfurther purification. To a stirred solution of 25a (commercially available, 120.0 mg, 1.0 mmol) or 25b-j (1.0 mmol) in DMSO (5 mL)was added bromoacetonitrile (300.0 mg, 2.5 mmol), K2CO3 (556.8 mg, 4 mmol) at room temperature. The mixture was stirred for 3hours at room temperature, quenched by H2O (30 mL), and extracted by EtOAc (30 mL × 2). The organic layer was concentrated anddissolved in anhydrous THF (5 mL). LiAlH4 (1 M solution in THF, 1 mL) was added at room temperature and stirred for 1 hour. Themixture was quenched by ice and filtered over celite. The filtrate was washed by saturated Na2CO3 solution (10 mL). The aqueouslayer was extracted by EtOAc (15 mL × 3). The combined organic layer was concentrated to give the crude mixture 26a-j which wasused for the next step directly without further purification
	With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 3h;	General procedure: To a stirred solution of 12a (commercially available, 236.1 mg,1.8 mmol) or 12b-f (1.8 mmol) in DMSO (5 mL) was added bromoacetonitrile(300.0 mg, 2.5 mmol), K2CO3 (556.8 mg, 4 mmol) atroom temperature. The mixture was stirred for 3 h at room temperature,quenched by H2O (30 mL), and extracted by EtOAc(30 mL 2). The organic layer was washed by saturated sodiumchloride solution, and dried over anhydrous MgSO4, filtered andconcentrated. The residue was purified by Flash column chromatography(DCM/MeOH, 0e10percent) to afford the crude target compounds13a-f (15-30percent yield for two steps).

Reference： [1]Chinese Chemical Letters,2019
[2]European Journal of Medicinal Chemistry,2019,vol. 178,p. 715 - 725

21
[ 610791-05-4 ]
[ 590-17-0 ]
C₁₂H₁₈N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		Compound 1E (5 g, 23 mmol) was dissolved in anhydrous tetrahydrofuran (50 ml) and cooled to -78 C. Lithium hexamethyldisilazide (1.0M tetrahydrofuran solution) (25 ml, 25 mmol) was then added dropwise. The solution was stirred for 1 hour. Bromoacetonitrile (3 g, 25 mmol) was then added dropwise. Stir for 30 minutes. Then gradually warmed to room temperature.When TLC showed that the reaction was complete, it was quenched by the addition of a saturated aqueous ammonium chloride solution (200 ml), and then extracted with ethyl acetate (3 × 100 ml). The combined organic layers were washed with brine and dried over sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 10: 1 to 3: 1 (volume ratio V: V)) to obtain the target compound 1F (4.8 g, yellow solid) in a yield of 82% .

Reference： [1]Patent: CN110357887,2019,A .Location in patent: Paragraph 0063-0066; 0076-0078

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P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Num. heavy atoms :	4
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	19.35
TPSA :	23.79 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.48 cm/s

Log Po/w (iLOGP) :	0.98
Log Po/w (XLOGP3) :	0.77
Log Po/w (WLOGP) :	0.9
Log Po/w (MLOGP) :	0.38
Log Po/w (SILICOS-IT) :	0.65
Consensus Log Po/w :	0.74

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Log S (ESOL) :	-1.07
Solubility :	10.2 mg/ml ; 0.0854 mol/l
Class :	Very soluble
Log S (Ali) :	-0.85
Solubility :	17.0 mg/ml ; 0.141 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.17
Solubility :	8.04 mg/ml ; 0.067 mol/l
Class :	Soluble

[ CAS No. 590-17-0 ] Bromoacetonitrile

Quality Control of [ 590-17-0 ]

Related Doc. of [ 590-17-0 ]

Product Details of [ 590-17-0 ]

Calculated chemistry of [ 590-17-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 590-17-0 ]

Application In Synthesis of [ 590-17-0 ]

[ 590-17-0 ] Synthesis Path-Upstream 1~2

[ 590-17-0 ] Synthesis Path-Downstream 1~21

Technical Information

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.26

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed