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[ CAS No. 3937-56-2 ] {[proInfo.proName]}

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Chemical Structure| 3937-56-2
Chemical Structure| 3937-56-2
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Product Details of [ 3937-56-2 ]

CAS No. :3937-56-2 MDL No. :MFCD00002991
Formula : C9H20O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ALVZNPYWJMLXKV-UHFFFAOYSA-N
M.W : 160.25 Pubchem ID :19835
Synonyms :

Calculated chemistry of [ 3937-56-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 8
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 47.7
TPSA : 40.46 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) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.35
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 1.7
Log Po/w (MLOGP) : 1.61
Log Po/w (SILICOS-IT) : 2.05
Consensus Log Po/w : 1.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.63
Solubility : 3.71 mg/ml ; 0.0232 mol/l
Class : Very soluble
Log S (Ali) : -2.59
Solubility : 0.412 mg/ml ; 0.00257 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.36
Solubility : 0.698 mg/ml ; 0.00436 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.58

Safety of [ 3937-56-2 ]

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 [ 3937-56-2 ]

* 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 [ 3937-56-2 ]
  • Downstream synthetic route of [ 3937-56-2 ]

[ 3937-56-2 ] Synthesis Path-Upstream   1~40

  • 1
  • [ 3937-56-2 ]
  • [ 821-99-8 ]
YieldReaction ConditionsOperation in experiment
65% With thionyl chloride In dichloromethane; N,N-dimethyl-formamide In a 500 ml eggplant type bottle, 1,9-nonanediol (5.0 g, 31.2 mmol) was added.Dichloromethane (100 ml) and DMF (3 drops).Thionyl chloride (11.7 g, 98.3 mmol) was dissolved in dichloromethane (155 ml).In an ice bath, the solution of thionyl chloride is added dropwise into the eggplant type bottle.The reaction was overnight.The reaction mixture was washed with saturated sodium bicarbonate solution and then washed with saturated sodium chloride solution.The organic phase is dried over anhydrous sodium sulfate.Evaporation gave 4.0 g of 1,9-dichlorononane (light yellow oil, yield 65percent).
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 4.1, p. 642 - 646[2] Zhurnal Organicheskoi Khimii, 1989, vol. 25, # 4, p. 716 - 721
[3] Patent: CN107721925, 2018, A, . Location in patent: Paragraph 0096; 0097
[4] Journal of the American Chemical Society, 1948, vol. 70, p. 3393
[5] Pharmaceutical Chemistry Journal, 1972, vol. 6, # 5, p. 283 - 286[6] Khimiko-Farmatsevticheskii Zhurnal, 1972, vol. 6, # 5, p. 11 - 14
  • 2
  • [ 3937-56-2 ]
  • [ 55362-80-6 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogen bromide In toluene for 30 h; Dean-Stark; Reflux In a 500 mL round bottom flask fitted with a Dean-Stark apparatus 1 ,9-nonanediol (Sigma- Aldrich) (20 g, 0.125 mol) was dissolved in toluene (500 ml). To this solution was added 21 mL hydrobromic acid (48 percent, 188 mmol) and the mixture was heated for 30 h at reflux. The water formed during the reaction was removed using a Dean—Stark trap. The progress of the reaction monitored by thin layer chromatography (TLC) indicated that all starting materials reacted withHBr. After cooling to room temperature, the mixture was washed with 1 M HCI (100 mL), 1M NaOH (100 ml), 100 mL water and finally with 100 mL brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude oil obtained was fractionally distilled to give 9-bromononanol in 94 percent yield. B.p.:124-128 ° C/2 mmHg (lit: 125- 126 °C/2 mmHg).
87% With hydrogen bromide In toluene at 110℃; for 24 h; General procedure: To a stirred solution of 1,6-hexanodiol 1a (1.00 equiv.), 1,9-nonanediol 1b (1.00 equiv.), or 1,12-dodecanediol 1c (1.00 equiv.), in 30 mL of toluene was added HBr 48 percent (2.00 equiv.). The reaction was stirred at 110 °C for 24 h. The solvent was removed under reduced pressure, and the residue was purified by column chromatography over silica gel, eluting with hexane/EtOAc 9:1, to yield pure haloalcohol 2a–c. These compounds were transformed into their corresponding azido alcohols 3a–c by SN2 substitution (Scheme 1). A stock solution of 0.5 M NaN3 in DMSO was prepared by stirring the solution for 24 h at room temperature. To a 100-mL round-bottom flask equipped with a magnetic stir bar was added a 0.5 M solution of NaN3 in DMSO at room temperature. To this solution was added the bromo alcohol 2a (1.00 equiv.), 2b (1.00 equiv.), or 2c (1.00 equiv.), and the mixture was stirred for 24 h at room temperature.The reaction was quenched with H2O (50 mL) and stirred until it cooled to room temperature. The mixture was extracted with Et2O (3 9 30 mL), and the resulting extracts were washed with H2O (3 x 50 mL) and brine (50 mL). The organic layer was dried (Na2SO4) and filtered, and the residue obtained was purified by column chromatography over silica gel, eluting with hexane/EtOAc 9:1, to yield pure alkyl azido alcohols 3a–c. A solution of the azido alcohol 3a (1.00 equiv.), 3b (1.00 equiv.), or 3c (1.00 equiv.) in CH2Cl2 (50 mL) was cooled to 0 °C. Et3N (2.00 equiv.) and methanesulfonyl chloride (2.00 equiv.) was added. The reaction mixture was stirred for 24 h and then allowed to reach room temperature. The reaction mixture was poured into crushed ice (70 mL) and was then extracted with methylene chloride (3 9 30 mL). The organic layer was dried (Na2SO4), filtered, and evaporated under reduced pressure. The residue obtained was purified by column chromatography over silica gel, eluting with hexane/EtOAc 9:1, to yield highly purified halo alcohol pure methanesulfonate alkyl azides compounds 4a, 4b, and 4d.
76% With hydrogen bromide In water; toluene for 6 h; Reflux; Inert atmosphere According to a known protocol,23 1,9-nonanediol (4) (8.0 g, 50 mmol, 1 eq) was dissolved in toluene (100 mL) and 48percent HBr (66 mL, 400 mmol, 8 eq) was added. Then the reaction mixture was refluxed for 6 h. After completion the reaction mixture was cooled to room temperature and brine (100 mL) was added. The aqueous phase was extracted with hexane (2 100 mL), the combined organic layer was dried over MgSO4 and evaporated. The crude mixture obtained was purified by column chromatography (17 cm 5 cm, cyclohexane/ethyl acetate, 20:1) to give a white solid. Yield: 8.5 g (76percent). M.p.: 42-43 °C. 1H NMR (400 MHz, CDCl3): δ = 1.25 – 1.38 (m, 9H, 4-CH2, 5-CH2, 6-CH2, 7-CH2, OH), 1.43 (quin, 3JH,H = 6.5 Hz, 2H, 3-CH2), 1.56 (quin, 3JH,H = 7.2 Hz, 2H, 8-CH2), 1.85 (p, 3JH,H = 7.2 Hz, 2H, 2-CH2), 3.41 (t, 3JH,H = 6.9 Hz, 2H, 1-CH2), 3.64 (t, 3JH,H = 6.6 Hz, 2H, 9-CH2) ppm. 13C NMR (101 MHz, CDCl3): δ = 25.7 (C-7), 28.1 (C-3), 28.6 (C-4), 29.3 (C-5), 29.3 (C-6), 32.7 (C-2), 32.8 (C-8), 34.0 (C-1), 63.0 (C-9) ppm. HRMS (ESI+): m/z C9H19BrO + Na+: calcd. 245.0517, found 245.0511. The spectroscopic data agree with published ones.23
1.1 kg With hydrogen bromide In toluene at 90 - 100℃; for 24 h; Large scale 1,9-nonanediol (1 kg) was added to toluene (20 L), hydrobromic acid (40percent, 2.5 L) was added with stirring, heated to reflux (Internal temperature 90-100 ° C) 24 hrs. (4 L) and cold water (4 L) were added and the layers were stirred. The organic phase was washed successively with saturated aqueous sodium bicarbonate and aqueous solution, dried over anhydrous sodium sulfate, dried over anhydrous sodium bicarbonate, Spin dry 1.6 kg crude product, adding n-hexane 4.8 L, stirring and heating dissolved, Crystallization was carried out to give 1.1 kg of 9-bromo-1-nonanol.
1.1 kg With hydrogen bromide In toluene at 90 - 100℃; for 24 h; Large scale 1. Add 1,9-nonanediol (1 kg) to toluene (20 L). Add hydrobromic acid (40percent, 2.5 L) with stirring and heat to reflux (internal temperature 90-100 ° C) for 24 hrs. The heating was stopped and cooled to 40 ° C. Ethyl acetate (4L) and cold water (4L) were added. The mixture was stirred and layered. The organic phase was washed successively with saturated aqueous sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and spun dry to 1.6 kg The crude product was added with 4.8 L of n-hexane, stirred and heated to dissolve and crystallized by cooling to obtain 1.1 kg of 9-bromo-1-nonanol
1.1 kg With hydrogen bromide In toluene at 90 - 100℃; for 24 h; Large scale 1,9-Nonanediol (1 kg) was added to toluene (20 L) and hydrobromic acid (40percent, 2.5 L)Heat reflux (internal temperature 90-100 ) 24 hrs. Stop heating, cooled to 40 ,Ethyl acetate (4L) and cold water (4L) were added, the mixture was stirred and layered,The organic phase was washed successively with saturated aqueous sodium bicarbonate solution and aqueous solution, dried over anhydrous sodium sulfate,Spin dried to 1.6 kg of crude product, adding n-hexane 4.8 L, stirring heated to dissolve, cooling crystallization,1.1 kg of 9-bromo-1-nonanol were obtained

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YieldReaction ConditionsOperation in experiment
99% With carbon tetrabromide; Cu(tmp)(BINAP)BF4; sodium bromide In N,N-dimethyl-formamide for 24 h; UV-irradiation; Inert atmosphere General procedure: To an open oven-dried reaction vial charged with a stir bar was added copper catalyst (2 mg,0.002 mmol, 0.01 equiv), the alcohol (0.20 mmol, 1.0 equiv), carbon tetrabromide (131.6 mg, 0.4mmol, 2.0 equiv) and sodium bromide (41 mg, 0.40 mmol, 2.0 equiv). The flask vial was capped,purged with a stream of nitrogen and dry DMF (1.5 mL) was added via syringe. The reactionmixture was stirred under purple LEDs (394 nm) for 24 h. The vessel was opened and the mixturewas poured into a separatory funnel containing Et2O (10 mL) and H2O (10 mL). The layers wereseparated, and the aqueous layer was extracted with Et2O (2 × 10 mL). The combined organiclayers were washed with sat. Na2S2O3 solution, brine, dried over Na2SO4 and concentrated invacuo. The residue was purified by chromatography (100 percent hexanes)
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[11] Helvetica Chimica Acta, 1926, vol. 9, p. 265
[12] Bulletin de la Societe Chimique de France, 1964, p. 3155 - 3158
[13] Journal of the Chemical Society, 1965, p. 2067 - 2072
  • 34
  • [ 3937-56-2 ]
  • [ 55362-80-6 ]
  • [ 4549-33-1 ]
Reference: [1] Chemische Berichte, 1981, vol. 114, # 6, p. 2245 - 2260
[2] Helvetica Chimica Acta, 1929, vol. 12, p. 478
[3] Helvetica Chimica Acta, 1926, vol. 9, p. 265
  • 35
  • [ 3937-56-2 ]
  • [ 4549-33-1 ]
  • [ 855751-72-3 ]
Reference: [1] Chemische Berichte, 1944, vol. 77/79, p. 669,673[2] Monatshefte fuer Chemie, 1947, vol. 77, p. 259,262
  • 36
  • [ 3937-56-2 ]
  • [ 10035-10-6 ]
  • [ 4549-33-1 ]
  • [ 855751-72-3 ]
Reference: [1] Chemische Berichte, 1944, vol. 77/79, p. 674
  • 37
  • [ 3937-56-2 ]
  • [ 41059-02-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539
[2] Journal of Fluorine Chemistry, 2003, vol. 123, # 2, p. 255 - 259
[3] Tetrahedron, 1999, vol. 55, # 12, p. 3595 - 3604
[4] Helvetica Chimica Acta, 1929, vol. 12, p. 478
  • 38
  • [ 3937-56-2 ]
  • [ 2834-05-1 ]
Reference: [1] Helvetica Chimica Acta, 1929, vol. 12, p. 478
  • 39
  • [ 3937-56-2 ]
  • [ 62871-09-4 ]
Reference: [1] Synthesis, 2002, # 1, p. 111 - 115
  • 40
  • [ 3937-56-2 ]
  • [ 99828-63-4 ]
Reference: [1] Molecules, 2013, vol. 18, # 5, p. 5201 - 5208
Same Skeleton Products
Historical Records