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[ CAS No. 536-40-3 ] {[proInfo.proName]}

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Chemical Structure| 536-40-3
Chemical Structure| 536-40-3
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Product Details of [ 536-40-3 ]

CAS No. :536-40-3 MDL No. :MFCD00007603
Formula : C7H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :PKBGHORNUFQAAW-UHFFFAOYSA-N
M.W : 170.60 Pubchem ID :10816
Synonyms :

Calculated chemistry of [ 536-40-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.35
TPSA : 55.12 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) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 1.18
Log Po/w (WLOGP) : 0.94
Log Po/w (MLOGP) : 1.73
Log Po/w (SILICOS-IT) : 0.84
Consensus Log Po/w : 1.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.91
Solubility : 2.09 mg/ml ; 0.0122 mol/l
Class : Very soluble
Log S (Ali) : -1.93
Solubility : 1.99 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.65
Solubility : 0.383 mg/ml ; 0.00224 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.08

Safety of [ 536-40-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 536-40-3 ]

* 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 [ 536-40-3 ]
  • Downstream synthetic route of [ 536-40-3 ]

[ 536-40-3 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 7335-27-5 ]
  • [ 536-40-3 ]
YieldReaction ConditionsOperation in experiment
91% With hydrazine hydrate In ethanol; waterReflux General procedure: Hydrazides (30–58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3–6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).
91.9% With hydrazine hydrate In ethanol at 80℃; for 6 h; (10.83 mmol) of ethyl 4-chlorobenzoate and 50 mL of absolute ethanol were added to a 100 mL round-bottomed flask and 1.08 g (21.67 mmol) of 80percent hydrazine hydrate was added. The temperature of the oil bath was 80Othe C heated under reflux for 6 h, the end of the reaction by TLC, the solvent was distilled off under reduced pressure, to the system was added 30 mL of purified water, extracted with dichloromethane, and finally as a white solid 1.7 g, yield 91.9percent,
82% With hydrazine hydrate In ethanolReflux General procedure: Ethylbenzoates (11-15, 1.5g, 9.98 mmol)and ethyl-2-phenylacetates (16-20, 1.5g, 9.13 mmol)were dissolved in ethanol and then hydrazine-hydrate(99percent) was added and reux for 8-12h. Ethanol wasconcentrated and the resultant residue was pouredin ice cold water and stirred for 15 -20 min, the solidsthat were thrown out was fltered at the pump anddried to obtain the corresponding benzohydrazides(21-25) and 2-phenylacetohydrazides (26-30) in 80-82percent yield.
79.3% With hydrazine hydrate In ethanolReflux General procedure: A solution of the isolated esters 2a–e (10mmol) in ethanol (20mL), hydrazine hydrate (97percent, 3mL) was added and heated under reflux for 5–8h. After cooling, the formed precipitate was filtered off, washed with water, dried, and crystallized from ethanol.
79.3% With hydrazine hydrate In ethanolReflux General procedure: Hydrazine hydrate (97percent, 30 mmol, 1.5 mL) was added to a solutionof the isolated esters 2a–e (10 mmol) in ethanol (20 mL), and themixture was heated at reflux for 5–8 h. After cooling, the resultingprecipitate was filtered off, washed with water, dried, and crystallizedfrom ethanol.

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  • 2
  • [ 1126-46-1 ]
  • [ 536-40-3 ]
YieldReaction ConditionsOperation in experiment
93.4% With hydrazine hydrate In ethanol for 5 h; Reflux General procedure: A solution of hydrazine hydrate (20.00 mmol) in 2 mL EtOH was added dropwise to the ester 2 (5.00 mmol). The mixture was refluxed for 5 h and filtered, and the corresponding acid hydrazide 3 was obtained by washing the residue with ice water.
92% With hydrazine hydrate In methanolReflux General procedure: Compound (2) (0.1 mol) was taken in a round-bottom flaskwith methanol (100 mL). Hydrazine hydrate (99percent) (0.15mol, 5.7 mL) was added drop wise with gentle stirring. Thereaction mixture was refluxed for 4–6 h. Excess of methanolwas distilled off under reduced pressure. The precipitatedhydrazide was dried and re-crystallized from methanol(Zamani and Faghihi 2003).
88% With hydrazine hydrate In water at 50 - 60℃; for 0.166667 h; General procedure: Pathway A-Hydrazine hydrate 64percent (v/v) (30.0 mL, 0.33 mol) was heated up to 50-60 °C. The methyl ester previously isolated (0.01 mol) was added and the mixture was refluxed during 10 min. The cooling down was proceeded sequentially in a water bath, followed by ice bath and dry ice - ethanol bath. The solid was filtered and washed with cold water. Different conditions were needed to obtain 4-nitro-3-(trifluoromethyl)benzhydrazide (3d) and 4-nitrobenzhydrazide (3 h). Hydrazine hydrate 64percent (v/v) (30.0 mL, 0.33 mol) was cooled down in ice bath to -3 to 2 °C. The respective methyl ester (0.01 mol) was added and the mixture was stirred during 1 hour. The cooling down was proceeded in dry ice - ethanol bath. The solid was filtered and washed with cold water. Pathway B-each substituted benzoic acid (0.01 mol) was refluxed during 4 h in 20.0 mL (0.50 mol) of anhydrous methanol and 0.5 mL (1.0 mmol) of sulfuric acid. The reaction mixture was cooled down to room temperature. and the hydrazine hydrate 80percent (v/v) (10.0 mL, 0.11 mol) was added. The system was maintained into vigorously stirring for more 30 minutes. In the case of compounds with 4-nitro and 4-nitro-3-trifluoromethyl substituent groups attached in the benzene moiety, after the addition of hydrazine hydrate 80percent (v/v) at room temperature, the reaction mixture was cooled down in ice bath and maintained into stirring during 1 hour. After these periods, the mixture was maintained at cold temperature to give 3.
82.4% With hydrazine hydrate In ethanolReflux General procedure: To a solution of the appropriate methyl benzoate ester (1.0 mmol) in ethanol (30 mL), hydrazine monohydrate (0.15 g, 3.0 mmol) was added. The reaction mixture was heated under reflux overnight. After completion of the reaction, the solvent was evaporated under reduced pressure, and the residue was washed with water (2 x 3 mL), and the obtained solid was filtered and dried to give benzohydrazide derivatives 3a-c.

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  • 3
  • [ 74-11-3 ]
  • [ 536-40-3 ]
YieldReaction ConditionsOperation in experiment
74%
Stage #1: With thionyl chloride In methanol at 50℃; for 4 h; Cooling with ice
Stage #2: With hydrazine hydrate In ethanol for 4 h; Reflux
Dissolve 4-chlorobenzoic acid (3. 2g, 20mmol) in methanol (30mL) and slowly add 2mL of thionyl chloride in an ice bath. Heat at 50 ° C for 4h (15mLX3), spin-dried for use; the previous step in 30mL ethanol, 80percent hydrazine hydrate added 4mL, reflux reaction heating (15mLX3), the mixture was cooled to room temperature, 4h, cooling, precipitation of white solid, filter drying, a white solid 2. 5g, yield 74percent.
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  • 4
  • [ 619-56-7 ]
  • [ 536-40-3 ]
YieldReaction ConditionsOperation in experiment
78% With silica gel; hydrazine In neat (no solvent) at 130℃; for 24 h; Inert atmosphere; Sealed tube General procedure: These compounds were prepared using the standard procedure at 130°C for 20–24h. For each reaction, the crude product was adsorbed onto silica gel and purified on a 15cm×2.5cm silica gel column eluted with 80percent EtOAc in hexanes. The isolated yields are given in Table 7.
Reference: [1] Tetrahedron, 2015, vol. 71, # 48, p. 9101 - 9111
  • 5
  • [ 1601-18-9 ]
  • [ 21909-54-6 ]
  • [ 536-40-3 ]
YieldReaction ConditionsOperation in experiment
70% With hydrazine hydrate In ethanol for 30 h; Reflux The methyl ester of indomethacin (0.01 mol) and hydrazine hydrate (99percent) (0.2 mol) in presence of absolute ethanol (50 mL) were refluxed for 30 h. The reaction mixture was concentrated by using rota vapor and poured in a beaker containing ice while stirring and kept for 4 h at room temperature.The solid was separated out by filtration. The product was dried and recrystallized from ethanol.The product was carefully checked by thin layer chromatography. Two compounds were isolated by column chromatography by using different fractions of n-hexane and ethyl acetate. The first compound was 2-(6-methoxy-2-methyl-1H-indol-3-yl) acetohydrazide compound (1) and was obtained as the major product. The second compound, 4-chlorobenzohydrazide (2) was obtained as minor product. Both the compounds were fully characterized by the spectral data. 2-(6-methoxy-2-methyl-1H-indol-3-yl) acetohydrazide (1). Color: white; Yield: 70percent; m.p.: 168–170 °C; UV max (Methanol) = 280 nm; 1H-NMR (500 MHz, DMSO-d6): δ = 2.38 (3H, s, CH3), 3.54 (2H, s,CH2), 3.80 (3H, s, OCH3), 4.26 (2H, s, NH2, D2O exchg.), 6.67 (1H, d, J = 8.5 Hz, Ar–H), 7.16 (2H, d,J = 7.5 Hz, Ar–H), 9.16 (1H, s, NH, D2O exchg.), 10.62 (1H, s, CONH, D2O exchg.); 13C-NMR (125 MHz,DMSO-d6): δ = 12.0 (CH3), 30.2 (CH2), 55.8 (OCH3), 101.1, 105.1, 109.8, 110.0, 111.7, 128.0, 129.3, 129.7,130.6, 134.3, 153.4, 170.8 (C=O); ms: m/z = 233.11 [M]+, 234.07 [M + 1]+; Analysis: C12H15N3O2 for,calcd. C 61.79, H 6.48, N 18.01percent; found C 61.58, H 6.46, N 18.05percent. 4-Chlorobenzohydrazide (2). Color: white; Yield: 20percent; m.p.: 148–150 °C; UV max (Methanol) = 230 nm;1H-NMR (500 MHz, DMSO-d6): δ = 4.53 (2H, s, NH2, D2O exchg.), 7.52 (2H, d, J = 8.5 Hz, Ar–H), 7.84(2H, d, J = 8.5 Hz, Ar–H), 9.87 (1H, s, CONH, D2O exchg.); 13C-NMR (125 MHz, DMSO-d6): δ = 128.86,129.32, 132.50, 136.25, 165.29; MS: m/z = 170.45 [M]+; Analysis: C7H7N2OCl for, calcd. C 49.28, H 4.14,N 16.42percent; found C 49.37, H 4.12, N 16.46percent.
Reference: [1] Molecules, 2018, vol. 23, # 6,
[2] Patent: US9808443, 2017, B1, . Location in patent: Page/Page column 6
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