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[ CAS No. 874-86-2 ] {[proInfo.proName]}

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Chemical Structure| 874-86-2
Chemical Structure| 874-86-2
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Product Details of [ 874-86-2 ]

CAS No. :874-86-2 MDL No. :MFCD00019761
Formula : C8H6ClN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 151.59 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 874-86-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.92
TPSA : 23.79 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 1.97
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 2.77
Consensus Log Po/w : 2.17

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.605 mg/ml ; 0.00399 mol/l
Class : Soluble
Log S (Ali) : -2.1
Solubility : 1.22 mg/ml ; 0.00803 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.49
Solubility : 0.0495 mg/ml ; 0.000327 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 874-86-2 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P405 UN#:2923
Hazard Statements:H301-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 874-86-2 ]

* 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 [ 874-86-2 ]
  • Downstream synthetic route of [ 874-86-2 ]

[ 874-86-2 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 874-86-2 ]
  • [ 6068-72-0 ]
Reference: [1] Journal of the Chemical Society, 1942, p. 103,107
  • 2
  • [ 1592-20-7 ]
  • [ 874-86-2 ]
YieldReaction ConditionsOperation in experiment
96.2% With formic acid; [5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrinato]iron(III) chloride; sodium nitrite In acetonitrile at 70℃; for 4.5 h; To the reaction tube were added 0.4 mmol of p-chloromethylstyrene, 2 mmol of sodium nitrite,5 mg of metallic iron (III) porphyrin, 4.5 ml of acetonitrile solvent, heated and stirred at 70 ° C in an air atmosphere,0.5 ml of formic acid was added dropwise within the first 0.5 hours, and after 4 hours of reaction, heating and stirring were stopped, and the mixture was cooled to room temperature,The crude product was obtained by rotary evaporator, and then purified by column chromatography to give the desired product,The column eluant used was a mixed solvent of petroleum ether and ethyl acetate.The p-chloromethylbenzonitrile structure is shown below:The compound was a white solid with a yield of 96.2percent and its nuclear magnetic data was as follows
95% With formic acid; sodium nitrite In acetonitrile at 70℃; for 4 h; Schlenk technique General procedure: A Schlenk tube was charged with olefins 1 (0.4 mmol), NaNO2 (138 mg, 2 mmol), HCOOH (0.5 mL, 10 mmol), and CH3CN(4.5mL). The reaction mixture was stirred at 70 °C under air atmosphere for 4 h. After cooling to room temperature, the solution was filtered to remove the solid by-product then was washed with ethyl acetate (3×10 mL). The solution was concentrated under vacuum and purified by column chromatography on silica gel (eluent: petroleum ether/ethyl acetate) to obtain the desired product 2.
Reference: [1] Patent: CN107573259, 2018, A, . Location in patent: Paragraph 0133-0137
[2] Tetrahedron Letters, 2016, vol. 57, # 24, p. 2620 - 2623
  • 3
  • [ 17201-43-3 ]
  • [ 874-86-2 ]
Reference: [1] Synthesis, 2010, # 5, p. 882 - 891
[2] Journal of Organometallic Chemistry, 1987, vol. 329, p. 349 - 356
  • 4
  • [ 10406-25-4 ]
  • [ 107-06-2 ]
  • [ 874-86-2 ]
Reference: [1] Patent: US6187945, 2001, B1,
  • 5
  • [ 104-85-8 ]
  • [ 74231-65-5 ]
  • [ 874-86-2 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 45, p. 5783 - 5786
[2] Journal of the American Chemical Society, 1925, vol. 47, p. 2191
[3] Tetrahedron Letters, 1988, vol. 29, # 45, p. 5783 - 5786
  • 6
  • [ 104-85-8 ]
  • [ 874-86-2 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2407 - 2413
[2] Russian Journal of General Chemistry, 2003, vol. 73, # 3, p. 389 - 393
[3] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 4, p. 711 - 719[4] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 4, p. 788 - 797
[5] Russian Journal of Organic Chemistry, 1996, vol. 32, # 10, p. 1447 - 1470
[6] Journal of the American Chemical Society, 1943, vol. 65, p. 2281,2283
[7] Chemische Berichte, 1889, vol. 22, p. 3208
[8] Journal of the American Chemical Society, 1925, vol. 47, p. 2191
[9] Chemische Berichte, 1889, vol. 22, p. 3208
[10] Journal of the Chemical Society, 1956, p. 404,410
[11] Journal of Organic Chemistry, 1980, vol. 45, # 25, p. 5177 - 5183
[12] Journal of the American Chemical Society, 1980, vol. 102, # 2, p. 692 - 697
[13] Russian Journal of Organic Chemistry, 1994, vol. 30, # 12, p. 1946 - 1980[14] Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 12, p. 1847 - 1881
  • 7
  • [ 874-89-5 ]
  • [ 874-86-2 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 19, p. 3045 - 3048
  • 8
  • [ 874-89-5 ]
  • [ 1396318-76-5 ]
  • [ 874-86-2 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 19, p. 3045 - 3048
  • 9
  • [ 7782-50-5 ]
  • [ 104-85-8 ]
  • [ 74231-65-5 ]
  • [ 874-86-2 ]
Reference: [1] Journal of the American Chemical Society, 1925, vol. 47, p. 2191
  • 10
  • [ 7782-50-5 ]
  • [ 104-85-8 ]
  • [ 874-86-2 ]
Reference: [1] Chemische Berichte, 1889, vol. 22, p. 3208
  • 11
  • [ 4394-85-8 ]
  • [ 874-86-2 ]
  • [ 37812-51-4 ]
YieldReaction ConditionsOperation in experiment
98% With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3 h; Inert atmosphere; Schlenk technique General procedure: Under a N2 atmosphere, NaOH (3.0 equiv), NHC-Pd(II)-Im complex 1 (1.0 molpercent), water (1.0 mL), benzyl chloride 2a (0.8 mmol), and N-formylmorpholine 3a (2.0 equiv) were successively added into a Schlenk reaction tube. The mixture was stirred at 50 °C for 3 h. After cooling to room temperature, the reaction mixture was extracted with EtOAc, washed with brine, and dried over anhydrous Na2SO4. Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica gel (eluent: PE/EA = 5:1) to give the pure products 4a. 4-Morpholin-4-ylmethyl-benzonitrile (4j):19 Yellow solid, m.p. 78–81 °C; 1H NMR (300 MHz): δ 7.51 (d, J = 8.1 Hz, 2H), 7.38 (d, J = 8.1 Hz,2H), 3.61 (t, J = 4.5 Hz, 4H), 3.46 (s, 2H), 2.35 (t, J = 4.5 Hz, 4H); 13C NMR (75 MHz): δ 143.6, 131.8, 129.2, 118.6, 110.6, 66.6, 62.4, 53.3.
92% With potassium hydroxide In water at 50℃; for 3 h; Green chemistry General procedure: KOH (2.4mmol), H2O (1.0mL), (pseudo)halides 1 (0.8mmol), and formamides 2 (1.6mmol) were successively added into a reaction tube. Then the reaction mixture was stirred under the conditions shown in Tables 1–5. After the reactions were completed, the mixture was extracted by ethyl acetate, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure, and purified by flash chromatography to give products 3.
Reference: [1] Journal of Chemical Research, 2013, vol. 37, # 10, p. 611 - 614
[2] Tetrahedron, 2014, vol. 70, # 4, p. 880 - 885
  • 12
  • [ 874-86-2 ]
  • [ 1642-81-5 ]
Reference: [1] Journal of the American Chemical Society, 1925, vol. 47, p. 3007
[2] Journal of the American Chemical Society, 1925, vol. 47, p. 2191
[3] Chemische Berichte, 1889, vol. 22, p. 3208
  • 13
  • [ 874-86-2 ]
  • [ 876-31-3 ]
YieldReaction ConditionsOperation in experiment
27 %Chromat. With copper(l) iodide In toluene at 180℃; for 20 h; Inert atmosphere; Sealed tube General procedure: 0.3 mmol CuI and 0.3 mL toluene were added into a dried 40 mL tube under a dry nitrogen atmosphere. After the mixture was stirred at room temperature for about 1 min, 0.5 mmol K4[Fe(CN)6], 1 mmol benzyl chloride, and 0.7 mL toluene were added under a dry nitrogen atmosphere. The reaction tube was sealed with a septum and placed in a constant-temperature oil bath set at 180(+/-5) °C to perform the reaction for 20 h. Once the reaction time was reached, the mixture was cooled to room temperature, then 1 mL solution of acetophenone (0.8 mmol/mL in dichloromethane) was added as an internal standard into the reaction tube. Subsequently, GC analysis of the mixture provided the yield of the product (note: in order to decrease the analysis error, the mixture after the reaction was not purified or concentrated). The cyanation product was identified by GC-MS data.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 23, p. 2825 - 2827
  • 14
  • [ 151-50-8 ]
  • [ 874-86-2 ]
  • [ 876-31-3 ]
Reference: [1] Chemische Berichte, 1889, vol. 22, p. 3208
  • 15
  • [ 64-17-5 ]
  • [ 151-50-8 ]
  • [ 874-86-2 ]
  • [ 876-31-3 ]
Reference: [1] Chemische Berichte, 1889, vol. 22, p. 3208
  • 16
  • [ 874-86-2 ]
  • [ 5462-71-5 ]
Reference: [1] Chemische Berichte, 1889, vol. 22, p. 3208
  • 17
  • [ 874-86-2 ]
  • [ 2458-12-0 ]
Reference: [1] Chemische Berichte, 1894, vol. 27, p. 2165
  • 18
  • [ 874-86-2 ]
  • [ 874-89-5 ]
YieldReaction ConditionsOperation in experiment
96.2% With potassium carbonate In water at 80℃; for 10 h; Into a 3000 mL four-necked flask, 138 g of potassium carbonate, 151.5 g of 4-chloromethylbenzonitrile, and 2300 g of water were placed.Heat to 80°C, react for 10 hours, sample for HPLC detection,It was confirmed that the hydrolysis reaction of 4-chloromethylbenzonitrile was complete. Dichloromethane extraction was performed in the hydrolysis reaction solution (800 mL each time, and extracted 3 times at room temperature).The extract was distilled to remove the extraction solvent to obtain 128 g of 4-cyanobenzyl alcohol with a purity of 96-98percent and a yield of 96.2percent.
Reference: [1] Patent: CN107556214, 2018, A, . Location in patent: Paragraph 0031; 0032; 0035; 0038; 0041; 0044; 0047
[2] Journal of the Chemical Society, 1942, p. 103,107
[3] Journal of Organic Chemistry, 2015, vol. 80, # 4, p. 2310 - 2318
  • 19
  • [ 874-86-2 ]
  • [ 51359-78-5 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 404,410
  • 20
  • [ 74-89-5 ]
  • [ 874-86-2 ]
  • [ 34403-48-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1962, vol. 660, p. 60 - 73
  • 21
  • [ 124-40-3 ]
  • [ 874-86-2 ]
  • [ 35525-86-1 ]
Reference: [1] Journal of the American Chemical Society, 1971, vol. 93, p. 6542 - 6551
  • 22
  • [ 874-86-2 ]
  • [ 60710-80-7 ]
Reference: [1] Chemische Berichte, 1894, vol. 27, p. 2165
  • 23
  • [ 104-85-8 ]
  • [ 74231-65-5 ]
  • [ 874-86-2 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 45, p. 5783 - 5786
[2] Journal of the American Chemical Society, 1925, vol. 47, p. 2191
[3] Tetrahedron Letters, 1988, vol. 29, # 45, p. 5783 - 5786
  • 24
  • [ 874-86-2 ]
  • [ 74231-65-5 ]
Reference: [1] Chemische Berichte, 1891, vol. 24, p. 2422
  • 25
  • [ 7782-50-5 ]
  • [ 104-85-8 ]
  • [ 74231-65-5 ]
  • [ 874-86-2 ]
Reference: [1] Journal of the American Chemical Society, 1925, vol. 47, p. 2191
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