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[ CAS No. 873-49-4 ] {[proInfo.proName]}

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Chemical Structure| 873-49-4
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Product Details of [ 873-49-4 ]

CAS No. :873-49-4 MDL No. :MFCD00001275
Formula : C9H10 Boiling Point : -
Linear Structure Formula :- InChI Key :VFSFCYAQBIPUSL-UHFFFAOYSA-N
M.W : 118.18 Pubchem ID :70112
Synonyms :

Calculated chemistry of [ 873-49-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.91
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -4.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 3.27
Log Po/w (WLOGP) : 2.5
Log Po/w (MLOGP) : 3.78
Log Po/w (SILICOS-IT) : 3.06
Consensus Log Po/w : 2.95

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.103 mg/ml ; 0.000871 mol/l
Class : Soluble
Log S (Ali) : -2.94
Solubility : 0.134 mg/ml ; 0.00114 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.94
Solubility : 0.134 mg/ml ; 0.00114 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 873-49-4 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P403+P235 UN#:3295
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 873-49-4 ]

* 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 [ 873-49-4 ]
  • Downstream synthetic route of [ 873-49-4 ]

[ 873-49-4 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 873-49-4 ]
  • [ 2712-78-9 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1935 - 1939[2] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 10, p. 2124 - 2129
  • 2
  • [ 873-49-4 ]
  • [ 1124-14-7 ]
YieldReaction ConditionsOperation in experiment
85% With bromine In chloroform at -78℃; for 0.75 h; (Reference example 9) 4-(4-Cyclopropylphenyl)butyric acid Bromine (12.5 mL, 244 mmol) was dropwise added to a solution of cyclopropylbenzene (25.0 g, 212 mmol) in chloroform (430 mL) with stirring at -78°C and the mixture was stirred for 45 minutes. A 10percent aqueous sodium sulfite solution and water were added to the reaction mixture at -78°C and chloroform was added thereto to separate it. The thus obtained organic phase was separated, washed with a saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane) to obtain 1-bromo-4-cyclopropylbenzene (35.5 g, yield: 85percent). Tetrakis-(triphenylphosphine)palladium (5.33 g, 4.61 mmol) and 3-butyn-1-ol (31.5 g, 450 mmol) were added to a solution of the obtained 1-bromo-4-cyclopropylbenzene (35.5 g, 180 mol) in piperidine (345 mL) and the mixture was stirred at 80°C under nitrogen atmosphere for 3 hours. The reaction mixture was evaporated under reduced pressure and ethyl acetate and a 1N aqueous hydrochloric acid solution were added to the residue to separate it. The thus obtained organic phase was separated, washed with a 1N aqueous hydrochloric acid solution, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate, 4:1-3:1) to obtain 4-(4-cyclopropylphenyl)but-3-yn-1-ol (30.2 g, yield: 90percent). A 6N aqueous sulfuric acid solution (250 mL) was added to a solution of the obtained 4-(4-cyclopropylphenyl)but-3-yn-1-ol (27.8 g, 149 mmol) in methanol (300 mL) and the mixture was heated under reflux for 6 hours. After it was left to stand, methanol of the reaction mixture was evaporated under reduced pressure and ethyl acetate was added thereto to separate it. The thus obtained organic phase was separated, washed with a saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The thus obtained residue was purified by silica gel chromatography (hexane:ethyl acetate, 4:1-2:1) to obtain 1-(4-cyclopropylphenyl)-4-hydroxybutan-1-one (18.7 g, yield: 61percent). Hydrazine monohydrate (10.4 mL) and potassium hydroxide (14.4 g) were added to a solution of the obtained 1-(4-cyclopropylphenyl)-4-hydroxybutan-1-one (17.5 g, 85.8 mmol) in ethylene glycol (90 mL) and the mixture was heated under reflux at 180°C for 6 hours. Water was added to the reaction mixture to dilute it and ethyl acetate was added thereto to separate it. The thus obtained organic phase was separated, washed with a saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate, 5:1-3:1) to obtain 4-(4-cyclopropylphenyl)butan-1-ol (15.8 g, yield: 97percent). TEMPO (2,2,6,6-tetramethylpiperidine 1-oxyl free radical) (905 mg, 5.79 mmol) and a sodium hydrogenphosphate buffer solution (300 mL, 0.67M, pH 6.7) were added to a solution of the obtained 4-(4-cyclopropylphenyl)butan-1-ol (15.7 g, 83.0 mmol) in acetonitrile (300 mL) and the mixture was stirred at 35°C for 10 minutes. After an aqueous sodium chlorite solution (16.4 g, water 80 mL) was added to the reaction mixture, a 2percent aqueous hypochlorous acid solution (42.3 mL) was further added dropwise thereto and the mixture was stirred at 35°C for 2 hours. A 1N aqueous sodium hydroxide solution (250 mL) was added to the reaction mixture and the mixture was poured into ice-water (300 mL) added with sodium sulfite (30 g), followed by stirring of the mixture for 5 minutes. Ether was added thereto to separate it. An aqueous phase was taken, concentrated hydrochloric acid was added thereto to acidify it and ether was added thereto to separate it. The thus obtained organic phase was separated and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 4-(4-cyclopropylphenyl)butyric acid (15.8 g, yield: 88percent) as a white solid.;
52% With mercury(I) oxide; bromine; potassium carbonate In dichloromethane at -30℃; for 4.66667 h; In a flame dried flask under N2 blanket, compound D (1.5 g, 4.9 MMOL) was dissolved in dry THF (30 mL) and COOLED TO-78°C. N-BUTYL lithium (1.9 M in hexanes, 5.4 mL, 9.7 MMOL) was added followed after 45 min by compound E (1.27 g, 6.3 MMOL). The cold bath was removed after 2 h and the reaction mixture was allowed to warm to rt over 45 minutes then quenched with aq NH4CI. EtOAc (30 mL) was added to dilute the reaction mixture. The reaction mixture was washed with brine (100 mL x 2). The organic layer was dried over NA2SO4 and then concentrated to dryness. The crude material was purified via sgc (25percent EtOAc/Hexanes) to give 545 mg (27percent) of compound F. Compound i (120 g, 1.0 mml) was dissolved in CH2CI2 (1.2 L) with HG20 (6.0 g, 14.4 MMOL) and K2CO3 (24.0 g, 0.17 mol) and cooled to-30 °C. Br2 (85.2 g, 1.1 mol) was added over 10 min period of time. The reaction mixture was stirred at-30 °C for 4.5 h. The reaction mixture was washed with H20 (1 L) and brine (1 L). The organic layer was dried over NA2SO4 and concentrated to dryness. The crude material was distilled under reduced pressure to give 103.8 g (52percent) of compound ii. In a flame dried flask under N2 blanket, compound ii (6.0 g, 30.5 MMOL) was dissolved in dry THF (30 mL) and cooled TO-78 °C. A solution of n-butyl lithium (1.75 M in hexanes, 17.4 mL, 30.5 MMOL) was added and the reaction mixture was stirred for 20 min. S02 was bubbled in the reaction for 20 min. It was slowly warmed up to rt. CH2CI2 (50 mL) was added and the mixture was reacted with NCS (5.0 g, 37.4 MMOL) at rt overnight. The reaction mixture was washed with brine (100 mL x 2). The organic layer was dried over NA2SO4 and then concentrated to dryness. The crude material was purified via sgc (5percent EtOAC/Hexanes) to give 3.65 g (55percent) of compound II. To a round-bottom flask was added compound iii (3.0 g, 13.8 MMOL) and KF (2.4 g, 41.4 MMOL) followed by addition of acetone (50 mL) and water (30 mL). The reaction mixture was stirred at room temperature overnight. The solvent was then removed. Methylene chloride (40 mL) was added and it was washed with brine (40 mL). The organic layer was dried over NA2SO4 and then concentrated to dryness to give 2.77 g (100percent) of compound E.
21% With bromine; sodium acetate In acetic acid at 0 - 20℃; EXAMPLE XIX Compound 44. Cyclopropyl benzene (48.5 g, 410 mmol), glacial acetic acid (510 mL), and sodium acetate (38.9 g, 474 mmol) were added to a roundbottomed flask. The flask was cooled in an ice-water bath. A solution of bromine (66.3 g, 414 mmol) dissolved in 105 mL of acetic acid was added dropwise over 90 min. The reaction mixture was stirred at temperatures between 0 C. and 10 C. for 5 h. The reaction was then allowed to warm to rt overnight. Hexanes (1300 mL) and water (250 mL) were added. Aqueous NaHSO3 (1M) was added until the reaction mixture changed from yellow to clear. The layers were separated. The organic layer was washed with water, 1M aq Na2CO3, and brine, then dried with Na2SO4. The solvent was evaporated and the crude product was purified to give 17 g of p-cyclopropylbromobenzene (21percent) (Compound 44).
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 11, p. 1727 - 1732
[2] Patent: EP1733724, 2006, A1, . Location in patent: Page/Page column 56
[3] Organic Letters, 2009, vol. 11, # 11, p. 2453 - 2456
[4] Patent: WO2004/48322, 2004, A1, . Location in patent: Page 38-39
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3760 - 3764
[6] Patent: US2003/232859, 2003, A1, . Location in patent: Page 48
[7] Journal of Organic Chemistry, 1976, vol. 41, p. 2262 - 2266
[8] Journal of Organic Chemistry USSR (English Translation), 1975, vol. 11, p. 1389 - 1393[9] Zhurnal Organicheskoi Khimii, 1975, vol. 11, p. 1403 - 1408
[10] Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 2356 - 2360[11] Zhurnal Organicheskoi Khimii, 1977, vol. 13, p. 2535 - 2541
[12] Journal of the American Chemical Society, 1968, vol. 90, p. 3404 - 3415
[13] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1979, p. 262 - 268
[14] Journal of Organic Chemistry, 1978, vol. 43, # 6, p. 1154 - 1158
[15] J. Gen. Chem. USSR (Engl. Transl.), 1963, vol. 33, p. 364 - 368[16] Zhurnal Obshchei Khimii, 1963, vol. 33, # 2, p. 371 - 376
[17] Journal of Organic Chemistry USSR (English Translation), 1974, vol. 10, p. 1697 - 1701[18] Zhurnal Organicheskoi Khimii, 1974, vol. 10, # 8, p. 1681 - 1686
[19] Patent: WO2004/56365, 2004, A2, . Location in patent: Page/Page column 107-108
[20] Patent: US2011/237791, 2011, A1, . Location in patent: Page/Page column 56
  • 3
  • [ 873-49-4 ]
  • [ 1124-14-7 ]
  • [ 65662-63-7 ]
  • [ 57807-28-0 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 11, p. 1727 - 1732
[2] Patent: WO2012/162115, 2012, A2, . Location in patent: Page/Page column 83-84
  • 4
  • [ 873-49-4 ]
  • [ 1124-14-7 ]
YieldReaction ConditionsOperation in experiment
21% With bromine; sodium acetate In water; acetic acid EXAMPLE XIX
Compound 44.
Cyclopropyl benzene (48.5 g, 410 mmol), glacial acetic acid (510 mL), and sodium acetate (38.9 g, 474 mmol) were added to a round bottomed flask.
The flask was cooled in an ice-water bath.
A solution of bromine (66.3 g, 414 mmol) dissolved in 105 mL of acetic acid was added dropwise over 90 min.
The reaction mixture was stirred at temperatures between 0° C. and 10° C. for 5 h.
The reaction was then allowed to warm to rt overnight.
Hexanes (1300 mL) and water (250 mL) were added.
Aqueous NaHSO3 (1M) was added until the reaction mixture changed from yellow to clear.
The layers were separated.
The organic layer was washed with water, 1M aq Na2CO3, and brine, then dried with Na2SO4.
The solvent was evaporated and the crude product was purified via sgc using hexanes as the mobile phase to give 17 g of p-cyclopropylbromobenzene (21percent) (Compound 44).
Reference: [1] Patent: US2003/96844, 2003, A1,
  • 5
  • [ 873-49-4 ]
  • [ 3240-34-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1935 - 1939[2] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 10, p. 2124 - 2129
  • 6
  • [ 873-49-4 ]
  • [ 75-36-5 ]
  • [ 1798-82-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4329 - 4337
  • 7
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  • [ 1798-82-9 ]
Reference: [1] Journal of Organic Chemistry, 1959, vol. 24, p. 1261,1266
  • 8
  • [ 873-49-4 ]
  • [ 75-36-5 ]
  • [ 6921-45-5 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 258, p. 229 - 238
[2] Journal of Organic Chemistry, 1959, vol. 24, p. 1261,1266
[3] Journal of the American Chemical Society, 1975, vol. 97, # 10, p. 2895 - 2898
[4] J. Gen. Chem. USSR (Engl. Transl.), 1963, vol. 33, p. 358 - 363[5] Zhurnal Obshchei Khimii, 1963, vol. 33, # 2, p. 365 - 371
[6] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4329 - 4337
  • 9
  • [ 873-49-4 ]
  • [ 6921-45-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1973, vol. 46, p. 204 - 209
  • 10
  • [ 873-49-4 ]
  • [ 10292-60-1 ]
  • [ 10292-61-2 ]
Reference: [1] Catalysis Science and Technology, 2017, vol. 7, # 23, p. 5677 - 5686
  • 11
  • [ 873-49-4 ]
  • [ 10292-61-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 10, p. 1959 - 1968
  • 12
  • [ 4885-02-3 ]
  • [ 873-49-4 ]
  • [ 20034-50-8 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 258, p. 229 - 238
  • 13
  • [ 50-00-0 ]
  • [ 873-49-4 ]
  • [ 20034-50-8 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1968, p. 2095 - 2096
  • 14
  • [ 110-82-7 ]
  • [ 84564-98-7 ]
  • [ 873-49-4 ]
  • [ 939-89-9 ]
  • [ 108-93-0 ]
Reference: [1] Tetrahedron, 1982, vol. 38, # 14, p. 2083 - 2088
  • 15
  • [ 873-49-4 ]
  • [ 167404-32-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3760 - 3764
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