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[ CAS No. 72934-37-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 72934-37-3
Chemical Structure| 72934-37-3
Chemical Structure| 72934-37-3
Structure of 72934-37-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 72934-37-3 ]

CAS No. :72934-37-3 MDL No. :MFCD00001289
Formula : C10H9ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YAHLWSGIQJATGG-UHFFFAOYSA-N
M.W :196.63 Pubchem ID :98606
Synonyms :

Calculated chemistry of [ 72934-37-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.38
TPSA : 37.3 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) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 2.36
Log Po/w (WLOGP) : 2.39
Log Po/w (MLOGP) : 2.45
Log Po/w (SILICOS-IT) : 2.87
Consensus Log Po/w : 2.4

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.76
Solubility : 0.345 mg/ml ; 0.00176 mol/l
Class : Soluble
Log S (Ali) : -2.78
Solubility : 0.324 mg/ml ; 0.00165 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.21
Solubility : 0.121 mg/ml ; 0.000617 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 72934-37-3 ]

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

Application In Synthesis of [ 72934-37-3 ]

* 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 [ 72934-37-3 ]
  • Downstream synthetic route of [ 72934-37-3 ]

[ 72934-37-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 64399-27-5 ]
  • [ 72934-37-3 ]
YieldReaction ConditionsOperation in experiment
95% Reflux The cyclopropanecarbonitrile ( 18 gm) obtained in example 1 was added to 20percent sulfuric acid (184ml). The temperature of the reaction mass was slowly raised and maintained at reflux for 10-12 hours. After 12 hours , ethyl acetate was used to extract the product. The acid product from the organic layer was then extracted into 20percent NaOH solution. The aqueous layer was then acidified to pH 2-4 with concentrated HCl. The white solid product obtained was filtered and washed with water. The product p- chlorophenylcyclopropanecarboxylic acid was dried. The yield was 90-95percent and the product had apurity of 99.4percent by HPLC. The melting point was 152-1550C.
90.3% With sodium hydroxide In water; diethylene glycol for 18 h; Reflux A stirred solution of 1-(4-chlorophenyl)cyclopropane-1-carbonitrile (step 1, 30.0 g, 169.49 mmol, 1.0 eq), sodium hydroxide (20.3 g, 508.47 mmol, 3.0 eq), diethylene glycol(120 ml) and water (35.4 ml) was refluxed for about 18 hours. TLC indicated startingmaterial was consumed and the desired product was observed. The reaction mixture was poured into water (1800 ml) and acidified to pH4.0 with concentrated HC1 (54 ml). The generated crystals were collected by filtration and dried under vacuum to obtain the desired product (30.0 g, 90.3percent yield) as a pale-brown colour solid. ‘H NMR (300 MHz, DMSO-d6):ppm 12.40 (br.s., 1H), 7.34 (m, 4H), 1.48-1.42 (m, 2H), 1.16-1.10 (m, 2H).
Reference: [1] Patent: WO2009/150660, 2009, A1, . Location in patent: Page/Page column 16
[2] Patent: WO2016/178092, 2016, A2, . Location in patent: Page/Page column 63; 64
[3] Patent: WO2017/64628, 2017, A1, . Location in patent: Page/Page column 33; 34
[4] Chemische Berichte, 1979, vol. 112, p. 3914 - 3933
[5] Patent: US2009/312558, 2009, A1, . Location in patent: Page/Page column 6
[6] Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19598 - 19601
[7] Organic Letters, 2014, vol. 16, # 24, p. 6314 - 6317
[8] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6545 - 6549
[9] Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4306 - 4311
  • 2
  • [ 140-53-4 ]
  • [ 72934-37-3 ]
Reference: [1] Chemische Berichte, 1979, vol. 112, p. 3914 - 3933
[2] Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19598 - 19601
[3] Patent: WO2016/178092, 2016, A2,
[4] Patent: WO2017/64628, 2017, A1,
[5] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6545 - 6549
[6] Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4306 - 4311
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