Home Cart 0 Sign in  

[ CAS No. 590-17-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 590-17-0
Chemical Structure| 590-17-0
Structure of 590-17-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 590-17-0 ]

Related Doc. of [ 590-17-0 ]

Alternatived Products of [ 590-17-0 ]

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 :

Calculated chemistry of [ 590-17-0 ]

Physicochemical Properties

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 Ų

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

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

Water Solubility

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

Medicinal Chemistry

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

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:
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   1~30

  • 1
  • [ 99-56-9 ]
  • [ 590-17-0 ]
  • [ 6232-92-4 ]
YieldReaction ConditionsOperation in experiment
96% for 4 h; Reflux 4-Nitrobenzene-1,2-diamine 1a (5.06g, 33mmol) was suspended in 90mL of a mixed solvent of acetonitrile and water (V/V=1:8), and bromoacetonitrile (3.55g, 33.5mmol) was added under stirring, the reaction solution was heated to reflux for 4 hours.
The reaction solution was cooled down to room temperature, the pH was adjusted to alkaline with aqueous ammonia, yellow solid precipitated.
The solution was subjected to suction filtration, the filter cake was washed with water (20mL*5) and subjected to infrared drying to obtain 5-nitro-1H-benzo[d]imidazol-2-amine 3a (5.65g, orange solid), yield:96percent.
MS m / z (ESI): 178.9 [M + 1]
Reference: [1] Patent: EP3339305, 2018, A1, . Location in patent: Paragraph 0085; 0086
  • 2
  • [ 123-75-1 ]
  • [ 590-17-0 ]
  • [ 29134-29-0 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 27, p. 8307 - 8317
[2] Patent: US6743564, 2004, B2,
  • 3
  • [ 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
  • 4
  • [ 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
  • 5
  • [ 603-35-0 ]
  • [ 590-17-0 ]
  • [ 16640-68-9 ]
Reference: [1] Patent: WO2012/76435, 2012, A1, . Location in patent: Page/Page column 30
[2] Journal of Organic Chemistry, 2014, vol. 79, # 8, p. 3696 - 3703
[3] Angewandte Chemie, International Edition, 2014, vol. 53, # 36, p. 9462 - 9465,4[4] Angewandte Chemie, 2014, vol. 126, # 36, p. 9616 - 9619,4
  • 6
  • [ 84109-17-1 ]
  • [ 590-17-0 ]
  • [ 605-39-0 ]
  • [ 22364-68-7 ]
Reference: [1] Synthesis, 1987, # 1, p. 40 - 42
  • 7
  • [ 107-91-5 ]
  • [ 932021-64-2 ]
  • [ 590-17-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 1, p. 63 - 67
  • 8
  • [ 624-75-9 ]
  • [ 590-17-0 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1887, vol. <2>47, p. 400
[2] Journal of the American Chemical Society, 1980, vol. 102, # 4, p. 1367 - 1371
  • 9
  • [ 107-14-2 ]
  • [ 590-17-0 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 4, p. 1367 - 1371
[2] Helvetica Chimica Acta, 1971, vol. 54, p. 2543 - 2551
  • 10
  • [ 75-05-8 ]
  • [ 590-17-0 ]
Reference: [1] Journal of Organic Chemistry, 1953, vol. 18, p. 501,502
  • 11
  • [ 75-05-8 ]
  • [ 3252-43-5 ]
  • [ 590-17-0 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 7, p. 2423 - 2426
  • 12
  • [ 683-57-8 ]
  • [ 590-17-0 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 2694[2] Chemische Berichte, 1908, vol. 41, p. 2542
[3] J. Gen. Chem. USSR (Engl. Transl.), 1962, vol. 32, p. 890 - 894[4] Zhurnal Obshchei Khimii, 1962, vol. 32, p. 900 - 905
  • 13
  • [ 506-68-3 ]
  • [ 25553-97-3 ]
  • [ 1531-37-9 ]
  • [ 590-17-0 ]
Reference: [1] Chemische Berichte, 1907, vol. 40, p. 3939
  • 14
  • [ 348-57-2 ]
  • [ 75-05-8 ]
  • [ 372-18-9 ]
  • [ 590-17-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1997, vol. 70, # 8, p. 1875 - 1878
  • 15
  • [ 64248-56-2 ]
  • [ 75-05-8 ]
  • [ 348-57-2 ]
  • [ 372-18-9 ]
  • [ 590-17-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1997, vol. 70, # 8, p. 1875 - 1878
  • 16
  • [ 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
  • 17
  • [ 611-20-1 ]
  • [ 590-17-0 ]
  • [ 62208-67-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 5, p. 1187 - 1197
  • 18
  • [ 64248-56-2 ]
  • [ 75-05-8 ]
  • [ 348-57-2 ]
  • [ 372-18-9 ]
  • [ 590-17-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1997, vol. 70, # 8, p. 1875 - 1878
  • 19
  • [ 590-17-0 ]
  • [ 624-75-9 ]
YieldReaction ConditionsOperation in experiment
100% With sodium iodide In acetone Step 2. The method follows that of S5; 2, 6-piperidinedimethanol (3.80 g, 26.21 mmol), iodoacetonitrile (5.24 g, 31.45 mmol), Et3N (4. 38 mL, 31.45 mmol) and dry DMF (20 mL). Purification by flash chromatography using CH2CI2/CH30H (9: 1) as eluent afforded the title compound as a straw-coloured oil (2.5 g, 53 percent). FAB MS, m/z (M+H) + 185. The iodoacetonitrile was prepared by the use of the Finkelstein reaction. BrCH2CN (3.77 g, 0.0314 mmol) was added dropwise to a stirred solution of Nal (4.71 g, 0.031 mmol) in acetone. Precipitation of NaBr occurred within a few minutes and indicated that exchange of the halides had taken place. Sodium bromide was filtered off, and the acetone was removed in vacuo. Crude yield (5.24 g, 100 percent).
Reference: [1] Patent: WO2005/61453, 2005, A1, . Location in patent: Page/Page column 15
[2] Journal of the American Chemical Society, 1980, vol. 102, # 4, p. 1367 - 1371
  • 20
  • [ 590-17-0 ]
  • [ 683-57-8 ]
Reference: [1] Synthesis, 1974, p. 574 - 575
  • 21
  • [ 590-17-0 ]
  • [ 122-52-1 ]
  • [ 2537-48-6 ]
Reference: [1] Phosphorus, Sulfur and Silicon and Related Elements, 2000, vol. 160, p. 195 - 205
  • 22
  • [ 589-15-1 ]
  • [ 590-17-0 ]
  • [ 57775-08-3 ]
Reference: [1] Synthesis, 1984, # 10, p. 842 - 844
  • 23
  • [ 100-46-9 ]
  • [ 590-17-0 ]
  • [ 3010-05-7 ]
YieldReaction ConditionsOperation in experiment
94% With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 3 h; Large scale Preparation 115
2-(Benzylamino)acetonitrile
To a solution of benzylamine (1250 g, 11.68 mol) and DIPEA (2878 g, 22.31 mol) in acetonitrile (13 L) was added 2-bromoacetonitrile (1340 g, 11.17 mol) and the reaction was stirred at room temperature for 3 hours.
The reaction was concentrated in vacuo and dissolved in DCM (2.5 L).
The solution was washed with water (1.5 L*2), concentrated in vacuo and purified using silica gel column chromatography eluting with 10-30percent EtOAc in petroleum ether (1600 g, 94percent).
1H NMR (400 MHz, CDCl3): δ ppm 3.57 (s, 2H), 3.94 (s, 2H), 7.35-7.37 (m, 5H).
26% With triethylamine In tetrahydrofuran at 0℃; for 16 h; Inert atmosphere To a solution of benzyl amine (SM2) (10 g, 0.093 mol) in THF (60 mL) was added triethylamine (26 mL, 0.186 mol) and stirred for 10 minutes under nitrogen atmosphere. 2- bromoacetonitrile (8 mL, 0.112 mol) was added slowly at 0 °C and stirred at room temperature for 16 h. After consumption of the starting material (by TLC), the reaction was quenched with ice water (100 mL) and extracted with EtOAc (2 x 500 mL). The combined organic layer was washed brine, dried over Na2S04 and concentrated to obtain crude compound which was purified by column chromatography by eluting 30percent EtOAc/ n-hexane to afford Int-A (3.5 g, 26percent) as a liquid. H NMR (400 MHz, DMSO-d6) δ 7.36-7.30 (m, 4H), 7.29-7.22 (m, 1H), 3.75 (d, J = 5.9 Hz, 2H), 3.57 (d, J = 7.3 Hz, 2H), 3.03 (quin, / = 6.5 Hz, 1H). LCMS (m/z): 147.1 [M++1].
Reference: [1] Patent: US2016/52930, 2016, A1, . Location in patent: Paragraph 0708
[2] Chemical Communications, 2017, vol. 53, # 70, p. 9745 - 9748
[3] Patent: WO2018/26798, 2018, A1, . Location in patent: Page/Page column 33; 35
[4] Journal of Organic Chemistry, 2002, vol. 67, # 25, p. 8928 - 8937
  • 24
  • [ 95-48-7 ]
  • [ 590-17-0 ]
  • [ 50635-21-7 ]
Reference: [1] ACS Combinatorial Science, 2014, vol. 16, # 2, p. 85 - 91
  • 25
  • [ 60811-18-9 ]
  • [ 3264-82-2 ]
  • [ 590-17-0 ]
  • [ 251570-03-3 ]
Reference: [1] Patent: EP962457, 1999, A1,
  • 26
  • [ 288-32-4 ]
  • [ 590-17-0 ]
  • [ 98873-55-3 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 0.5 h;
Stage #2: at 20℃; for 2 h;
To a solution of 1H-Imidazole (5 g, 73.5 mmol) in THF was added sodium hydride (1.8 g, 45 mmol) and stirred at room temperature for 0.5 hour before addition of then bromo-acetonitrile (8.8 g, 73.9 mmol) and stirring at room temperature for 2 hours.
The reaction was quenched via the addition of water (50 mL) and saturated ammonium chloride (50 mL) solution and the mixture was extracted with ethyl acetate (100 mL*3).
The combined organics layer was dried over anhydrous magnesium sulfate, filtered, and concentrated.
The crude residue was purified on silica gel (petroleum ether:ethyl acetate=10:1) to afford 2-(1H-imidazol-1-yl)acetonitrile (4.6 g, 59percent) as a yellow oil. LRMS m/z: 108 [M+H+].
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 9, p. 3185 - 3198
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 18, p. 2110 - 2116
[3] New Journal of Chemistry, 2002, vol. 26, # 7, p. 926 - 932
[4] Patent: US2015/65522, 2015, A1, . Location in patent: Paragraph 0469; 0470; 0471
[5] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 2009 - 2016
  • 27
  • [ 288-32-4 ]
  • [ 590-17-0 ]
  • [ 104619-51-4 ]
Reference: [1] Patent: US2007/105866, 2007, A1, . Location in patent: Page/Page column 65
  • 28
  • [ 79099-07-3 ]
  • [ 590-17-0 ]
  • [ 774609-73-3 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1.16667 h;
Stage #2: at 20℃; for 2 h;
To an oven-dried flask equipped with a stirring bar and rubber septum was added anhydrous THF (250 mL). Diisopropylamine (7.0 mL, 50.2 mmole) was added and the solution cooled to-78 °C. To the cooled solution was added n-butyllithium (1.6 M in hexanes, 31 mL, 50.2 MMOLE) over 10 minutes. The reaction mixture was stirred for 60 min and N-BOC-4-PIPERIDONE (10.0 g, 50.2 mmole, in 10 mL of anhydrous THF) BROMOACETONITRILE (4.2 mL, 60.2 mmole) and HMPA (20 mL) was added and the mixture stirred for an additional 2 h at RT. The reaction mixture was quenched with brine and concentrated in vacuo. The residue was taken up in ethyl acetate (500 mL) and washed with sat. NAHCO3 (2 x 200 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to obtain the title compound (7.0 g, 58percent) as a yellow oil : H NMR (400 MHz, CDCl3) 8 3.90 Hz (bs, 2H), 3.16 Hz (m, 2H), 2.55 Hz (s, 2H), 1.74 Hz (m, 2H), 1.50 (m, 2H), and 1.47 (s, 9H). LC-MS (ES) M/E 241.2 (M + H).
Reference: [1] Patent: WO2004/87145, 2004, A2, . Location in patent: Page/Page column 31-32
  • 29
  • [ 269410-08-4 ]
  • [ 590-17-0 ]
  • [ 1093307-35-7 ]
YieldReaction ConditionsOperation 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 ( 10percent to 100percent EtOAc/hexane) to obtain 2-(4-(4,4,5,5-tetramethyl-l ,3,2- dioxaborolan-2-yl)-lH-pyrazol-l-yl)acetonitrile (0.38g, 63percent yield). MS (ESI) m/z: 234.1 (M+H+).
39% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24 h; 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 (10-60percent Hexanes/EtOAc as the gradient eluent) to afford the title compound (2.42 g, 39percent yield). ‘H NIVIR (400 MHz, DMSO-d6) 8.04 (s, 1H), 7.71 (s, 1H), 5.49 (s, 2H), 1.25 (s, 12H).
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
  • 30
  • [ 142851-03-4 ]
  • [ 590-17-0 ]
  • [ 495414-81-8 ]
YieldReaction ConditionsOperation 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
Same Skeleton Products
Historical Records