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[ CAS No. 1570-45-2 ] {[proInfo.proName]}

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Chemical Structure| 1570-45-2
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Product Details of [ 1570-45-2 ]

CAS No. :1570-45-2 MDL No. :MFCD00006428
Formula : C8H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MCRPKBUFXAKDKI-UHFFFAOYSA-N
M.W : 151.16 Pubchem ID :15291
Synonyms :

Calculated chemistry of [ 1570-45-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.32
TPSA : 39.19 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) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 1.43
Log Po/w (WLOGP) : 1.26
Log Po/w (MLOGP) : 0.66
Log Po/w (SILICOS-IT) : 1.51
Consensus Log Po/w : 1.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.88
Solubility : 1.98 mg/ml ; 0.0131 mol/l
Class : Very soluble
Log S (Ali) : -1.86
Solubility : 2.1 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.491 mg/ml ; 0.00325 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.3

Safety of [ 1570-45-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1570-45-2 ]

* 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 [ 1570-45-2 ]
  • Downstream synthetic route of [ 1570-45-2 ]

[ 1570-45-2 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 1570-45-2 ]
  • [ 6457-49-4 ]
  • [ 1126-09-6 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 212,216
  • 2
  • [ 1570-45-2 ]
  • [ 20691-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 3831
  • 3
  • [ 67-56-1 ]
  • [ 1570-45-2 ]
  • [ 2459-09-8 ]
YieldReaction ConditionsOperation in experiment
95% for 4 h; Reflux General procedure: The HT catalyst and substrate were added to MeOH and the mixture was refluxed with stirring. The reaction condition using HT and HT-like compounds as shown in Table 1 was carried out as follows: butyl decanoate 0.34 mmol, catalyst 5.2 mg, and MeOH 8 mL. After 8 h reaction, the amounts of the product and unreacted substrate were determined by GC using dichlorobenzene as an internal standard. Reaction condition in Table 2 was as follows: butyl decanoate 0.674 mmol, MeOH 16 mL, catalyst 10 mg(0.25 mmol of La/1 g HT). After 24 h reaction, the reaction mixture was analyzed by GC. Reaction condition in Table 3 was as follows: butyl dacanoate 0.674 mmol, MeOH 16 mL, catalyst 52 mg (0.25–1.00 mmol of La/1 g HT). After 8 h reaction, the reaction mixture was analyzed by GC. Reaction condition in Table 4 was as follows: substrate 0.674 mmol, MeOH 16 mL, catalyst La/HT-A 52 mg. The yields of products in the transesterification were determined by GC using dichlorobenzene or diethylene glycol dibutyl ether as an internal standard.
Reference: [1] Inorganica Chimica Acta, 2014, vol. 412, p. 114 - 120
  • 4
  • [ 1570-45-2 ]
  • [ 1126-09-6 ]
Reference: [1] Journal of Organic Chemistry, 1952, vol. 17, p. 249,254
[2] Helvetica Chimica Acta, 1954, vol. 37, p. 1672,1676
[3] Tetrahedron Letters, 1982, vol. 23, # 2, p. 193 - 196
  • 5
  • [ 1570-45-2 ]
  • [ 6457-49-4 ]
  • [ 1126-09-6 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 212,216
  • 6
  • [ 1570-45-2 ]
  • [ 54-85-3 ]
YieldReaction ConditionsOperation in experiment
86% With hydrazine hydrate In ethanol at 60℃; for 1 h; Commercially available ethyl isonicotinate was refluxed with hydrazine hydrate. for 1 hr at 60° C. and the solvent was evaporated. Trituration of this solid with diethyl ether afforded pure hydrazide 2 in 86percent yield. The treatment of hydrazide 2 with CS2 and KOH in 60 ° C. for 18 hrs produced a solid upon concentration in vacuo. It was found that this material could be easily purified by trituration with H20 followed by filtration to give thiol 3 in 78percent yield, thus avoiding chromatography over the first two steps. This operationally simple procedure afforded multi-gram quantities of 3 for subsequence focused library synthesis. Finally, diversification of the aryl ring was achieved by nucleophilic displacement reaction of thiol 3 with substituted aryl bromides in room temperature DMF using K2C03 as base.
86% With hydrazine hydrate In ethanol at 60℃; for 1 h; Commercially available ethyl isonicotinate was refluxed with hydrazine hydrate for 1 hr at 60° C. and the solvent was evaporated. Trituration of this solid with diethyl ether afforded pure hydrazide 2 in 86percent/o yield. The treatment of hydrazide 2 with CS2 and KOH in 60° C. for 18 hrs produced a solid upon concentration in vacuo. It was found that this material could be easily purified by trituration with H2O followed by filtration to give thiol 3 in 78percent yield, thus avoiding chromatography over the first two steps. This operationally simple procedure afforded multi-gram quantities of 3 for subsequence focused library synthesis. Finally, diversification of the aryl ring was achieved by nucleophilic displacement reaction of thiol 3 with substituted aryl bromides in room temperature DMF using K2CO3 as base.
86% With hydrazine hydrate In ethanol for 10.25 h; Cooling with ice; Reflux Isonicotinicacid ethyl ester 1 (1.5g, 10mmol) was dissolved in 15mL of ethanol, then under ice-cooling was slowly added dropwise with hydrazine hydrate (2g, 40mmol), after the addition was complete, it was stirred at room temperature for 15min, then heated under reflux for 10h. After completion of the reaction, ethanol was removed by rotary evaporation, poured into water, extracted with ethyl acetate, the organic phase was dried and concentrated to give the desired product 2 (1.2g, 86percent), without purification into the next step.
85% With hydrazine hydrate In ethanol for 24 h; Reflux Step 1: 15.12 g (0.1 mol) of ethyl pyridine-4-carboxylate and 10.00 g (0.2 mol) of hydrazine hydrate (NH 2 NH 2 · H 2 O) were added to 50 mL of ethanol, refluxed for 24 h, cooled to room temperature, and the solution was spun dry and recrystallized. The 11.62 g (0.085 mol) pyridine-4-formyl hydride was obtained in a yield of 85percent.
73% With hydrazine hydrate In ethanol for 6 h; Reflux To a solution of ethyl isonicotinate (1.44 g, 10 mmol) inEtOH (10 mL), 85percent hydrazine hydrate (2 mL, 35 mmol)was added dropwise. The mixture was heated under refluxfor 6 h. After the reaction was over, the mixture was cooledto room temperature, filtered, washed with cool ethyl acetate,and then dried to give white solid isonicotinyi hydrazine 2,yield (1.0 g, 73percent).
73% With hydrazine hydrate In water for 6 h; A mixture of ethyl isonicotinate (1.44 g, 10 mmol) and 85percent hydrazine hydrate (2 mL, 35 mmol) was heated under reflux for 6 h. The mixture was cooled to room temperature,filtered, washed with cool ethyl acetate, then dried to give white solid isonicotinohydrazide 2. Yield 1.0 g, 73percent.
12.9 g With hydrazine hydrate In ethanol for 3 h; Reflux General procedure: An ethanol (300 ml) suspension of salicylic acid(13.8 g; 0.1 mol) and strongly acidic ion-exchange resin,Amberlyst-15 (5 g) were stirred with refluxing for three days.Insoluble catalyst was separated by filtration, and washed withethanol (3 20 ml). Combined ethanol filtrates were mixed with hydrazine hydrate (20 ml; 20.5 g; 0.4 mol) and refluxed with slowsolvent distillation using the modified Hickman still apparatus(Scheme 3). After 3 h of refluxing, the volume of the reaction mixturewas reduced to about 50 ml and white precipitate started toform. The white suspension was cooled to room temperature andthen left at 5 C for 1 h. Insoluble product was separated by filtration,washed with ice cold ethanol, and dried on air to give pureproduct (13.2 g; 87percent).

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[11] Monatshefte fuer Chemie, 1912, vol. 33, p. 403
[12] Acta Chimica Academiae Scientiarum Hungaricae, 1958, vol. 14, p. 197,199
[13] Chimica, 1952, vol. 7, p. 229
[14] Roczniki Chemii, 1953, vol. 27, p. 161,163[15] Chem.Abstr., 1954, p. 13688
[16] Yakugaku Zasshi, 1951, vol. 71, p. 1002[17] Chem.Abstr., 1952, p. 8120
[18] Journal of the American Pharmaceutical Association (1912-1977), 1956, vol. 45, p. 478
[19] Pharm. Ind., 1952, vol. 14, p. 366
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  • 7
  • [ 1570-45-2 ]
  • [ 24252-37-7 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 3831
  • 8
  • [ 1570-45-2 ]
  • [ 62-53-3 ]
  • [ 3034-31-9 ]
Reference: [1] Synthesis, 2012, vol. 44, # 1, p. 42 - 50
[2] Research on Chemical Intermediates, 2012, vol. 38, # 8, p. 1961 - 1968
  • 9
  • [ 1570-45-2 ]
  • [ 141-78-6 ]
  • [ 26377-17-3 ]
  • [ 141-97-9 ]
YieldReaction ConditionsOperation in experiment
87% With lithium hexamethyldisilazane In tetrahydrofuran at -40℃; for 0.333333 h; Inert atmosphere General procedure: To the solution of ester (10 mmol) in THF (20 mL) and ethyl acetate (70 mmol), LiHMDS (30 mmol) was added very quickly at -40 °C, and stirred at this temperature for 20 min. After completion of the reaction, reaction mixture was quenched with acetic acid (50 mmol) and then basified using 10percent NaHCO3 solution, extracted with ethyl acetate (2.x.100 mL), the combined organic layer was washed with water and brine solution and dried over Na2SO4. The specific purification procedure for each compound has been included along with their characterization data.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 12, p. 4193 - 4197
  • 10
  • [ 1570-45-2 ]
  • [ 141-78-6 ]
  • [ 26377-17-3 ]
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[2] Bulletin de la Societe Chimique de France, 1955, p. 79,83
[3] Journal of the American Chemical Society, 1945, vol. 67, p. 1468,1469
[4] Journal fuer Praktische Chemie (Leipzig), 1955, vol. <4> 2, p. 302,306
[5] Journal of the American Chemical Society, 1948, vol. 70, p. 2755,2757
[6] Patent: CN105566313, 2016, A, . Location in patent: Paragraph 0008; 0009
  • 11
  • [ 1570-45-2 ]
  • [ 141-78-6 ]
  • [ 26377-17-3 ]
  • [ 865077-43-6 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 11, p. 2333 - 2336
  • 12
  • [ 1570-45-2 ]
  • [ 15846-25-0 ]
  • [ 59341-68-3 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 6, p. 1203 - 1207
  • 13
  • [ 1570-45-2 ]
  • [ 91324-39-9 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1984, vol. 18, # 4, p. 253 - 258[2] Khimiko-Farmatsevticheskii Zhurnal, 1984, vol. 18, # 4, p. 435 - 440
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