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[ CAS No. 1635-61-6 ] {[proInfo.proName]}

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Chemical Structure| 1635-61-6
Chemical Structure| 1635-61-6
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Product Citations

Product Citations

Vlasenko, Yulia A ; To, Avery J ; Fortier, Tess , et al. DOI: PubMed ID:

Abstract: Herein, the successful syntheses of D3- and 13C-N-methyl and D9-tert-butyl Hoechst dyes are presented. This includes the preparation of the labelled D3- and 13C-N-methyl piperazines and D9-tert-butylated hydroxytoluene precursors. The tert-butyl Hoechst dye is known to bind a specific RNA aptamer. Spectroscopic NMR studies of the labelled Hoechst dye-aptamer complexes allowed for the unambiguous assignment of chemical shifts, as well as the dynamics of the bound dye.

Keywords: 13C- ; D- ; Hoechst dye ; NMR spectroscopy

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Product Details of [ 1635-61-6 ]

CAS No. :1635-61-6 MDL No. :MFCD00007776
Formula : C6H5ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZCWXYZBQDNFULS-UHFFFAOYSA-N
M.W : 172.57 Pubchem ID :74218
Synonyms :

Calculated chemistry of [ 1635-61-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.68
TPSA : 71.84 ?2

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) : -5.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 2.72
Log Po/w (WLOGP) : 2.36
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 0.03
Consensus Log Po/w : 1.43

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.96
Solubility : 0.189 mg/ml ; 0.00109 mol/l
Class : Soluble
Log S (Ali) : -3.88
Solubility : 0.0226 mg/ml ; 0.000131 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.535 mg/ml ; 0.0031 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 1635-61-6 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P260-P262-P264-P270-P271-P273-P280-P284-P301+P310+P330-P302+P352+P310-P304+P340+P310-P314-P361+P364-P391-P403+P233-P405-P501 UN#:2237
Hazard Statements:H300+H310+H330-H373-H411 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1635-61-6 ]

* 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.

  • Downstream synthetic route of [ 1635-61-6 ]

[ 1635-61-6 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 1635-61-6 ]
  • [ 108-98-5 ]
  • [ 43156-47-4 ]
YieldReaction ConditionsOperation in experiment
96.4% With ammonia; In isopropyl alcohol; Example 2 In an autoclave, 255 g of 5-chloro-2-nitroaniline (78.3percent by weight) were suspended in 250 ml of isopropanol. The reaction mixture was heated to 60° C. and 95.7 g of ammonia were pumped into the autoclave, resulting in a pressure of 9 bar. At this temperature, 161 g of thiophenol (98percent by weight) were then pumped into the autoclave over the course of 1.5 hours. At the same time, the pressure was maintained at 9 bar by further metered addition of ammonia. After 6 hours, the autoclave was cooled to room temperature and vented. The content of the autoclave was filtered off, the autoclave was rinsed with isopropanol and the liquid used for rinsing was also filtered off. The combined residues were washed with water and dried. This gave 298.6 g of 2-nitro-5-(phenylthio)-aniline in the form of a yellow powder having a content of 91.2percent by weight. This corresponds to a yield of 96.4percent of theory.
95.8% With ammonia; In 2-methyl-propan-1-ol; Example 3 In an autoclave, 200 g of 5-chloro-2-nitroaniline (79.2percent by weight) were suspended in 200 ml of isobutanol. The reaction mixture was heated to 60° C. and 26 g of ammonia were pumped into the autoclave, resulting in a pressure of 4 bar. At this temperature, 126 g of thiophenol (98percent by weight) were then pumped into the autoclave over the course of 1.5 hours. At the same time, the pressure was maintained at 4 bar by further metered addition of ammonia. After 6 hours, the autoclave was cooled to room temperature and vented. The content of the autoclave was filtered off, the autoclave was rinsed with isobutanol and the liquid used for rinsing was also filtered off. The combined residues were washed with water and dried. This gave 240.6 g of 2-nitro-5-(phenylthio)-aniline in the form of a yellow powder having a content of 90.0percent by weight. This corresponds to a yield of 95.8percent of theory.
In N-methyl-acetamide; EXAMPLE I 5 G. of 2-amino-4-chloro-1-nitrobenzene is added to a solution of sodium phenyl mercaptide, prepared under nitrogen from 2.53 g. 57percent sodium hydride and 6.2 ml. thiophenol in 20 ml. dimethylformamide, with a 10 ml. dimethylformamide rinse. The mixture is stirred under nitrogen for three hours at 20°-30°C and then diluted with water. The crude product is washed with water and hexane, then recrystallized from methanol, yielding 2-amino-4-phenylthio-1-nitrobenzene.
With potassium carbonate; In N-methyl-acetamide; water; Thiophenol (44 g.) was added, over a period of 5 minutes and under an atmosphere of dry nitrogen, to a suspension of 5-chloro-2-nitro-aniline (66.5 g.; prepared according to Fuson et al, J. Org. Chem., 12, 799-806, 1947) and anhydrous potassium carbonate (60.6 g.) in dimethylformamide (200 ml.). The reaction mixture was heated under reflux for 8 hours and then cooled. Water (200 ml.) was added dropwise whilst maintaining the temperature at 5°-10° C. The precipitated solid was filtered off, washed well with water and recrystallized from isopropanol, to give 3-amino-4-nitro-diphenyl thioether (83 g.), m.p. 117°-118° C., in the form of a pale brown solid.
In N-methyl-acetamide; water; EXAMPLE XI 2.53 G. 57percent sodium hydride in oil suspension in 20 ml. dimethylformamide is treated with 6.2 ml. thiophenol under nitrogen. 5.0 G. 2-amino-4-chloro-1-nitrobenzene is added and the mixture stirred for three hours. Water is added and the product filtered off and washed with water and hexane. Recrystallization from methanol gives pure 2-amino-4-phenylthio-1-nitrobenzene. 1.8 G.
In N-methyl-acetamide; PREPARATION 3 5 G. of 2-amino-4-chloro-1-nitrobenzene is added to a solution of sodium phenyl mercaptide, prepared under nitrogen from 2.53 g. 57percent sodium hydride and 6.2 ml. thiophenol in 20 ml. dimethylformamide, with a 10 ml. dimethylformamide rinse. The mixture is stirred under nitrogen for 3 hours at 20°-30° C and then diluted with water. The crude product is washed with water and hexane, then recrystallized from methanol, yielding 2-amino-4-phenylthio-1-nitrobenzene.

  • 2
  • [ 326-62-5 ]
  • [ 1635-61-6 ]
  • (3-Amino-4-nitro-phenyl)-(2-fluoro-phenyl)-acetonitrile [ No CAS ]
  • 3
  • [ 1635-61-6 ]
  • [ 335349-57-0 ]
YieldReaction ConditionsOperation in experiment
88% With N-iodo-succinimide; acetic acid; In water; at 50℃; for 3.0h;Inert atmosphere; Compound number 103 (i.e., 6-chloro-5-(3-chlorophenyl)-2-trifluoromethylthiobenzimidazole) was prepared as follows. A 50-mL round-bottom flask was purged and maintained with an inert atmosphere of nitrogen. 5-chloro-2-nitroaniline (10 g, 57.95 mmol, 1.00 equiv), acetic acid (100 mL) and NIS (13 g, 57.78 mmol, 1.00 equiv) was placed in the flask. The resulting solution was stirred for 3 h at 50 C. in an oil bath. The resulting solution was poured into 300 mL of H2O. The solid was collected by filtration. The solid was washed with 200 mL of (sat.) sodium bicarbonate and 3×200 mL of H2O. This resulted in 17 g (88%) of 5-chloro-4-iodo-2-nitroaniline as a yellow solid.
85% With N-iodo-succinimide; acetic acid; at 55℃; for 2.0h;Large scale; Compound 1 is2-nitro-5-chloro-aniline(1500 g, 8.7 mol) was added to 15 L of acetic acid,Then add N-iodosuccinimide See 3(1957. (^, 8.711101), heated to 55 (: reaction 211, 11 (: test the end of the reaction).The reaction solution was cooled to 10 C, filtered, the cake was washed with acetic acid, washed with water and saturated sodium bicarbonate solution, and washed with water until neutral.The crude product was dried to give the compound 2S 2-nitro-4-iodo-5-chloroaniline (2200 g, 7.4 mol) in 85%
84% With potassium acetate; Iodine monochloride; acetic acid; at 60℃; for 18.0h; 5-chloro-2-nitroaniline (5.00 g, 29.0 mmol), potassium acetate (5.69 g, 57.9 mmol) and iodine monochloride (9.41 g, 57.9 mmol) were stirred in acetic acid (100 ml) at 60C for 18h. Water was added to the mixture and the resulting suspension was filtered, washed with water and dried at 60C under reduced pressure to give 7.2 g (84 % yield) of the title compound. 1H NMR (400 MHz, DMSO-d6) _ ppm 7.26 (s, 1H) 7.60 (s, 2 H) 8.36 (s, 1H)
With Iodine monochloride; In sodium acetate; acetic acid; Example A1 5-Chloro-4-iodo-2-nitro-phenylamine Prepared from 5-chloro-2-nitroaniline by iodination with iodine monochloride in HOAc/NaOAc according to the general procedure A (80 C.). Obtained as an orange solid. MS (EI) 298 (M+) and 300 [(M+2)+]; mp 202-203 C. (dec.).
With Iodine monochloride; In sodium acetate; acetic acid; Example A1 5-Chloro-4-iodo-2-nitro-phenylamine The title compound was prepared from 5-chloro-2-nitroaniline by iodination with iodine monochloride in HOAc/NaOAc according to the general procedure A (80 C.). Obtained as an orange solid. MS (EI) 298 (M+) and 300 [(M+2)+]; mp 202-203 C. (dec.).
With N-iodo-succinimide; acetic acid; at 50℃; Step A 5-chloro-4-iodo-2-nitroaniline. To a solution of 5-chloro-2-nitroaniline (25 g, 145 mmol) in AcOH (250 mL) was added N-iodosuccinimide (32.6 g 145 mmol). The mixture was stirred overnight at 50 C., cooled down to rt and filtered. The solid residue was washed with AcOH, water, saturated aqueous NaHCO3 and water, a nd then dried to afford the desired product as a brown solid, which was used in the next step without further purification.
With N-iodo-succinimide; In acetic acid; at 55℃; for 16.0h; A mixture of 5-chloro-2-nitroaniline (20.1 g, 116 tnmol) and N-iodosuccinimide (26.2 g, 116 mmol) in 260 niL of acetic acid was heated at 55 C for 16 h and then cooled in an ice-bath. The resulting yellow solid was collected by filtration and rinsed with acetic acid, water, aqueous NaHCO3 and water, and let stand in air for 2 h to provide 5-chloro-4-iodo-2~mtroaniline 1-5 as a yellow solid. 1H NMR (500 MHz, DMSO-d6): delta 7.23 (s, IH)5 8.32 (S5 IH)5 7.57 (s, 2H).
With N-iodo-succinimide; In acetic acid; at 50℃; To a solution of 5-chloro-2-nitroaniline (25 g, 145 mmol) in AcOH (250 mL) was added LambdaModosuccinimide (32.6 g 145 mmol). The mixture was stirred overnight at 500C, cooled to rt and filtered. The solid residue was washed with AcOH, water, saturated aqueous NaHCO3 and water, and then dried to afford the desired product as a brown solid, which was used in the next step without further purification.
With N-chloro-succinimide; In acetic acid; at 50℃; To a solution of 5-chloro-2-nitroaniline (25 g, 145 mmol) in AcOH (250 mL) was added JV-iodosuccinimide (32.6 g 145 mmol). The mixture was stirred overnight at 5O0C, cooled to rt and filtered. The solid residue was washed with AcOH, water, saturated aqueous NaHCO3 and water, and then dried to afford the desired product as a brown solid, which was used in the next step without further purification.
To a solution of 5-chloro-2-nitroaniline (25 g, 145 mmol) in AcOH (250 mL) was added N-iodosuccinimide (32.6 g 145 mmol). The mixture was stirred overnight at 50 C, cooled down to rt and filtered. The solid residue was washed with AcOH, water, saturated aqueous NaHC03 and water, and then dried to afford the desired product as a brown solid, which was used in the next step without further purification.
With sodium acetate; Iodine monochloride; acetic acid; at 90℃; for 3.0h; EXAMPLE 31A; 5-chloro-4-iodo-2-nitroaniline; To a mixture of 5-chloro-2-nitroaniline (8.63 g, 50 mmol) and sodium acetate (4.31 g,52.5 mmol) in acetic acid (45 mL) was added a solution of iodine monochloride (8.52 g, 52.5 mmol) in acetic acid (25 mL) slowly. After the addition, the suspension was stirred at 90C for 3 hours. The mixture was cooled and poured into ice-water. The precipitate was collected by filtration and air-dried to afford the title compound. ]H NMR (300 MHz, dimethylsulfoxide-de) delta ppm 8.36 (s, 1 H) 7.60 (s, 2 H) 7.27 (s, 1 H). MS ESI(-) m/z 296.1 (M-H)".

  • 6
  • [ 1635-61-6 ]
  • [ 99512-10-4 ]
YieldReaction ConditionsOperation in experiment
23% With zinc(II) cyanide;tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); at 120℃; for 96h; A solution of 5-chloro-2-nitro-aniline (6.902g, 40 mmol), Zn(CN)2 (2.818g, 24 mmol), and Pd(PPh3)4 (2.31 lg, 2 mmol) in DMF (40 mL) was heated to 120oC for 4 days. Cooled to room temperature. Partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate to provide 1.49g (23%) of 3-amino-4-nitro-benzonitrile.
  • 7
  • [ 1635-61-6 ]
  • [ 43156-48-5 ]
  • [ 598-52-7 ]
  • [ 108-98-5 ]
  • [ 79-22-1 ]
  • 5-phenylmercapto-benzimidazole-2-methyl-carbaminate [ No CAS ]
  • [ 43156-47-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In N-methyl-acetamide; water; potassium carbonate; acetic acid; EXAMPLE 40 5-Phenylmercapto-benzimidazole-2-methyl-carbaminate 20.9 g Of S-methyl-thiourea were reacted as described in Example 1 in 27 ml of water with 13.5 ml of chloroformic acid methyl ester, 45.7 ml of 25percent sodium hydroxide solution, 27 ml of glacial acetic acid, 100 ml of water and 29 g of 3,4-diaminodiphenyl-thioether. After recrystallization from a mixture of glacial acetic acid and methanol, 14 g of 4-phenylmercapto-benzimidazole-2-methyl-carbaminate melting at 233°C were obtained. For preparing the 3,4-diamino-diphenyl-thioether used as starting material, 22 g of thiophenol were heated for 6 hours under reflux in 100 ml of dimethylformamide with 5-chloro-2-nitroaniline in the presence of 30g of anhydrous potassium carbonate. The whole was allowed to cool, 100 ml of water were added and the crude product was filtered off with suction. After recrystallization from isopropanol, 38 g of 3-amino-4-nitro-diphenyl-thioether melting at 112°C were obtained. 38 g Of the 3-amino-4-nitro-diphenyl-thioether so obtained were added to a solution prepared by dissolving 180 g of crystal-water containing stannous chloride in 200 ml of glacial acetic acid and saturation with gaseous hydrochloric acid at room temperature.
  • 8
  • [ 389621-84-5 ]
  • [ 1635-61-6 ]
  • (3'-amino-4'-nitrobiphenyl-4-yl)(morpholin-4-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.4% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane;Inert atmosphere; Reflux; Compound P64: 5-{1 -[2-(Morpholin-4- l)ethyl]-1 H- razol-4-yl}-2-nitroaniline; 5-Chloro-2-nitroaniline (0.128 g, 0.744 mmol), pinacol ester of 1 -(2-morpholino- ethyl)-1 H-pyrazole-4-boronic acid (0.343 g, 1 .12 mmol) and tetrakis(triphenyl- phosphine)palladium(O) (0.086 g, 0.074 mmol) were placed in the Schlenk-type flask under argon flow and then the system was degassed. After 20 minutes under argon flow to the flask 10.5 ml of degassed 2-methoxyethyl methyl ether and 0.744 ml of degassed 2M Na2C03 solution were added dropwise. The reaction was carried out under reflux. The progress of the reaction was monitored by TLC analysis (system: heptane/ethyl acetate, 5/4). Ether was evaporated and ethyl acetate added. The mixture was filtered through celite layer. The filtrate was added with water and extracted with ethyl acetate (3 x 50 ml). Combined organic phases were washed with brine and dried over anhydrous Na2S04. A brown oil was obtained after filtration and concentration, and was purified by chromatography on silicagel (system: dichlorometan/methanol, 9/1 ). 0.152 g of a crystallizing oil were obtained (yield 64.3%). Compound P70: (3'-Amino-4'-nitrobiphenyl-4-yl)(morpholin-4-yl)methanone: The compound was obtained by the method analogous to that described for Compound P64. Starting from 5-chloro-2-nitroaniline (0.490 g, 2.84 mmol), 4- (morpholinocarbonyl)phenylboronic acid (1.020 g, 4.26 mmol) and tetrakis- (triphenylphosphine)palladium(O) (0.328 g, 0.284 mmol) in the solution in 40 ml of (2-methoxy)ethylmethyl ether with the addition of 2.8 ml of 2M Na2C03 solution, 0.812 g of the title product in the form of a yellow oil were obtained (yield 87.4%). MS-ESI: (m/z) calculated for Ci7Hi6N304 [M - H]": 326.11 , found 326.1. 1H NMR (500 MHz, DMSO-d6) delta 8.06 (d, J = 9.0 Hz, 1 H), 7.72 (d, J = 8.4 Hz, 2H), 7.55 (d, J = 8.4 Hz, 2H), 7.50 (bs, 2H), 7.33 (d, J = 1.9 Hz, 1 H), 6.96 (dd, J = 9.0, 2.0 Hz, 1 H), 3.77 - 3.34 (m, J = 115.9 Hz, 8H).
  • 10
  • [ 1635-61-6 ]
  • [ 107-02-8 ]
  • [ 6942-98-9 ]
YieldReaction ConditionsOperation in experiment
56% With hydrogenchloride; phosphoric acid; at 80 - 90℃; for 4.0h; first, after adding phosphoric acid 5.03g and hydrochloric acid 55mL to 100mL Erlenmeyer flask to dissolve the 5-chloro-2-nitroaniline (5.02g, 29.1mmol) and Stirring,. Acrolein at 80 degree (5.0mL, 74.8mmol) was added dropwise slowly over a period of 30 minutes, stirred for 3.5 hours at 90 degree .After cooling to room temperature, the reaction mixture was poured into ice water 100 g, was removed by suction filtration precipitate formed.The filtrate ammonia water was added to, was made alkaline (pH 13), the precipitated solid was suction filtered and dried in vacuom was 3.4 g in yield and 56% in yield,
  • 11
  • [ 1635-61-6 ]
  • [ 51419-59-1 ]
  • N-(5-chloro-2-nitrophenyl)-1-(4-methylphenyl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% General procedure: 5-Chloro-2-nitroaniline (173 mg, 1 mmol) was dissolved in DMF (3 mL) and dry sodium hydride (120 mg, 5 mmol) was added.The obtained mixture was stirred for 1 min and the suitable substitutedbenzenesulfonyl chloride 1 (a?g) or phenylethanesulfonylchloride 3 (a?g) (1,5 mmol) was added in several portions. The reaction was quenched after 2?6 h through the addition of a saturated NaHCO3 aqueous solution (5 mL). The mixture was extractedwith EtOAc (3 10 mL) and dried over Na2SO4. After removal ofthe solvent under reduced pressure, the residue was purified byflash chromatography using cyclohexane/AcOEt (80:20) as eluentand crystallized from Et2O.
  • 12
  • [ 1635-61-6 ]
  • [ 55215-55-9 ]
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