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[ CAS No. 3395-91-3 ] {[proInfo.proName]}

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Chemical Structure| 3395-91-3
Chemical Structure| 3395-91-3
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Product Details of [ 3395-91-3 ]

CAS No. :3395-91-3 MDL No. :MFCD00000250
Formula : C4H7BrO2 Boiling Point : -
Linear Structure Formula :Br(CH2)2CO2CH3 InChI Key :KQEVIFKPZOGBMZ-UHFFFAOYSA-N
M.W : 167.00 Pubchem ID :76934
Synonyms :

Calculated chemistry of [ 3395-91-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 30.5
TPSA : 26.3 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) : -6.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 0.81
Log Po/w (WLOGP) : 0.94
Log Po/w (MLOGP) : 1.09
Log Po/w (SILICOS-IT) : 0.98
Consensus Log Po/w : 1.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.19
Solubility : 10.8 mg/ml ; 0.0649 mol/l
Class : Very soluble
Log S (Ali) : -0.94
Solubility : 19.0 mg/ml ; 0.114 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.61
Solubility : 4.09 mg/ml ; 0.0245 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 3395-91-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H227-H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3395-91-3 ]

* 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 [ 3395-91-3 ]
  • Downstream synthetic route of [ 3395-91-3 ]

[ 3395-91-3 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 120-72-9 ]
  • [ 3395-91-3 ]
  • [ 6639-06-1 ]
YieldReaction ConditionsOperation in experiment
900mg
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1 h;
Stage #2: at 20℃; for 24 h;
Synthesis of 3-(1H-indol-1-yI)propanoic acid (Intermediate-25): A lOOmI RB flask fittedwith magnetic stirrer was charged with 10 ml of DMF. To the stirred solvent Starting Material-1 (1 .Og, 8.53 mmol) followed by Sodium hydride (400 mg, 10.24 mmol) were added. The resulting solution was stirred at room temperature for 1 hour. To the above solution methyl-3- bromo-propionate (2.13 g, 12.79 mmol) was added and stirred at room temperature for 24 hours. After completion of the reaction (reaction monitored by TLC), reaction mass wasdiluted with 3OmL of ice cold water and washed with ether. Aqueous portion was acidified with 1 N HCI (pH =2) and was then extracted with EtOAc and concentrated to give Intermediate-24 (900mg).
900 mg
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1 h;
Stage #2: at 20℃; for 24 h;
Synthesis of 3-(1H-indol-1-yl)propanoic acid (Intermediate-25)
A 100 ml RB flask fitted with magnetic stirrer was charged with 10 ml of DMF.
To the stirred solvent Starting Material-1 (1.0 g, 8.53 mmol) followed by Sodium hydride (400 mg, 10.24 mmol) were added.
The resulting solution was stirred at room temperature for 1 hour.
To the above solution methyl-3-bromo-propionate (2.13 g, 12.79 mmol) was added and stirred at room temperature for 24 hours.
After completion of the reaction (reaction monitored by TLC), reaction mass was diluted with 30 mL of ice cold water and washed with ether.
Aqueous portion was acidified with 1N HCl (pH=2) and was then extracted with EtOAc and concentrated to give Intermediate-24 (900 mg).
Reference: [1] Patent: WO2013/128465, 2013, A1, . Location in patent: Page/Page column 94
[2] Patent: US2015/158860, 2015, A1, . Location in patent: Paragraph 0332
[3] Patent: WO2004/43899, 2004, A1, . Location in patent: Page 37; 38
  • 2
  • [ 554-12-1 ]
  • [ 3395-91-3 ]
YieldReaction ConditionsOperation in experiment
88% With N-Bromosuccinimide; silver nitrate In acetone at 20℃; for 6 h; Methyl propiolate [(52] ml, 0. [583] mol) is combined with recrystallized N [BROMO-SUCCINIMIDE] (120 g, 0.674 mol) in 1,700 ml acetone under nitrogen. The solution is treated with silver nitrate (9.9 g, 0.0583 mol) neat in a single lot and the reaction is stirred 6 h at RT. The acetone is removed under reduced pressure [(25°C,] bath temperature) to provide a gray slurry. The slurry is washed with 2 x 200 ml hexane, the gray solid is removed by filtration, and the filtrate is concentrated in vacuo to provide 95 g of a pale yellow oily residue. The crude material is distilled via short path under reduced pressure [(65 °C,] about 25 mm Hg) into a dry ice/acetone cooled receiver to give 83.7 g (88percent) of methyl-3-bromo-propiolate as a pale yellow oil. Anal. calc'd for [C4H3BRO2] : C, 29.48 ; H, 1.86. Found: C, 29.09 ; H, 1.97.
Reference: [1] Patent: WO2004/13137, 2004, A1, . Location in patent: Page 76
[2] Tetrahedron Letters, 2010, vol. 51, # 13, p. 1793 - 1796
  • 3
  • [ 292638-85-8 ]
  • [ 3395-91-3 ]
Reference: [1] Journal of the Chinese Chemical Society, 2014, vol. 61, # 3, p. 364 - 368
[2] Org.Synth. Coll.Vol.III<1955>576,
[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1921, vol. 172, p. 1269[4] Annales de Chimie (Cachan, France), 1921, vol. <9> 15, p. 249
[5] Journal of Organic Chemistry, 1972, vol. 37, p. 3431 - 3433
  • 4
  • [ 590-92-1 ]
  • [ 67-56-1 ]
  • [ 3395-91-3 ]
Reference: [1] Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 9, p. 626 - 632[2] Bioorganicheskaya Khimiya, 1995, vol. 21, # 9, p. 724 - 730
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2009, vol. 52, # 9, p. 341 - 349
[4] Steroids, 1991, vol. 56, # 6, p. 311 - 315
[5] Journal of the American Chemical Society, 1938, vol. 60, p. 1375
[6] Journal of the Chemical Society, 1959, p. 103,104
[7] Tetrahedron Letters, 1998, vol. 39, # 47, p. 8563 - 8566
[8] Journal of Organometallic Chemistry, 2009, vol. 694, # 3, p. 323 - 331
  • 5
  • [ 67-56-1 ]
  • [ 57-57-8 ]
  • [ 3395-91-3 ]
Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 8, p. 937 - 960
  • 6
  • [ 14213-56-0 ]
  • [ 3395-91-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1966, vol. 34, p. 262 - 271
  • 7
  • [ 67-56-1 ]
  • [ 3395-91-3 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 16, p. 5724 - 5727
  • 8
  • [ 3878-55-5 ]
  • [ 3395-91-3 ]
Reference: [1] Journal of Organic Chemistry, 1969, vol. 34, # 4, p. 1172 - 1173
  • 9
  • [ 98-81-7 ]
  • [ 79-10-7 ]
  • [ 3395-91-3 ]
  • [ 16827-42-2 ]
Reference: [1] Chemische Berichte, 1954, vol. 87, p. 237,244
  • 10
  • [ 3395-91-3 ]
  • [ 122-52-1 ]
  • [ 3699-67-0 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 4450
[2] Journal of Organic Chemistry, 1959, vol. 24, p. 532,535
[3] Trudy Kazansk.chim.technol.Inst., 1957, # 23, p. 105;[4] Chem.Abstr., 1958, p. 9949
  • 11
  • [ 3395-91-3 ]
  • [ 75-16-1 ]
  • [ 35979-69-2 ]
YieldReaction ConditionsOperation in experiment
71.7% at -20℃; for 1 h; Inert atmosphere In a 250 mL round bottom flask, methyl 3-bromopropanoate (5.0 mL, 45.8 mmol, 1.0 eq.) was taken up in dry ether (55.2 mL, 0.83 M) under nitrogen and cooled to -20° C. To this, 3.0 M methylmagnesium bromide (45.8 ml, 137 mmol, 3.0 eq) was added in dropwise fashion and the resulting mixture was stirred for an hour. The reaction was quenched with aqueous ammonium chloride. The resulting white suspension was extracted with ether multiple times. The combined organics were washed with brine, dried over MgSO4, and concentrated to yield 4-bromo-2-methylbutan-2-ol as an oil (5.49 g, 71.7percent)
65% at 0 - 20℃; for 2 h; To a stirred solution of 4-bromo-butyric acid methyl ester (2 g, 12.27 mmol) in diethyl ether (20 mL) is added methyl magnesium bromide (16.4 mL, 49.08 mmol) at 0° C. and the mixture is stirred at room temperature for 2 hours.
The reaction mixture is quenched with 1 N HCl and extracted with diethyl ether (2*20 mL).
The combined organic extracts are washed with saturated brine solution (20 mL), dried over sodium sulphate, filtered, and concentrated.
The crude material is purified with silica gel column chromatography (combiflash) eluting in 20percent EtOAc/hexanes to give the title compound (1.3 g, 65percent).
1H NMR (400 MHz, CDCl3): δ 3.48 (t, J=8.0 Hz, 2H), 2.16 (t, J=7.4 Hz, 2H), 1.89 (s, 6H), 1.76 (s, 3H), 1.27 (s, 6H).
60% at 0 - 20℃; for 1 h; To a stirred solution of 4-bromo-butyric acid methyl ester (1 g, 5.9 mmol) in diethyl ether (20 mL) is added methyl magnesium bromide (19.9 mL, 23.9 mmol) at 0 °C and the mixture is stirred at room temperature for 1 hour. The reaction mixture is quenched with aqueous ammonium chloride (40 mL) and extracted with diethyl ether (2x20 mL). The combined organic extracts are washed with saturated brine solution (20 mL), dried over sodium sulphate, filtered, and concentrated. The crude material is purified by silica gel column chromatography (combiflash) eluting with 20percentEtOAc/hexanes to obtain title compound as pale pink liquid (0.6 g, 60percent). ^NMR (400 MHz, DMSO) δ 4.38 (s, 1H), 3.52-3.48 (m, 2H), 1.97-1.91 (m, 2H), 1.08 (s, 6H).
48.9% at 0 - 20℃; for 16 h; a) 4-Bromo-2-methylbutan-2-olTo a solution of methyl 3-bromopropanoate (5.0 g, 29.94 mmol, and 1.0 eq) in dry THF was added methyl magnesium bromide at 0°C. The mixture was stirred at RT for 16 h and quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50 percent ethyl acetate in hexane). Yield 48.9 percent (2.4 g). LC-MS (ESI): Calculated mass: 167.0; Observed massl67.1 [M+H]+ (it: 0.8-1.0 min).
48.9% at 0 - 20℃; for 16 h; To a solution of methyl 3-bromopropanoate (5.0 g,29.94 mmol, and 1.0 eq) in dry THF was added methyl mag21 nesium bromide at 0° C. The mixture was stirred at RT for 16 h and quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50percent ethyl acetate in hexane). Yield 48.9percent (2.4 g). LCMS (ESI): Calculatedmass: 167.0; Observedmass 167.1[M+ H] (it: 0.8-1.0mm).

Reference: [1] Patent: US2011/105509, 2011, A1, . Location in patent: Page/Page column 51
[2] Patent: US2016/333005, 2016, A1, . Location in patent: Paragraph 0074-0075
[3] Steroids, 1991, vol. 56, # 6, p. 311 - 315
[4] Patent: WO2015/105786, 2015, A1, . Location in patent: Page/Page column 13; 14
[5] Patent: WO2013/53983, 2013, A1, . Location in patent: Page/Page column 45; 46
[6] Patent: US2015/11548, 2015, A1, . Location in patent: Paragraph 0180
  • 12
  • [ 917-64-6 ]
  • [ 3395-91-3 ]
  • [ 35979-69-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 1417 - 1424
  • 13
  • [ 3395-91-3 ]
  • [ 37488-40-7 ]
  • [ 23574-01-8 ]
  • [ 793-19-1 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 35, p. 18229 - 18233
  • 14
  • [ 3395-91-3 ]
  • [ 62-53-3 ]
  • [ 21911-84-2 ]
Reference: [1] Journal of pharmaceutical sciences, 1972, vol. 61, # 11, p. 1739 - 1745
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