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[ CAS No. 112-82-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 112-82-3
Chemical Structure| 112-82-3
Chemical Structure| 112-82-3
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Product Details of [ 112-82-3 ]

CAS No. :112-82-3 MDL No. :MFCD00000230
Formula : C16H33Br Boiling Point : -
Linear Structure Formula :- InChI Key :HNTGIJLWHDPAFN-UHFFFAOYSA-N
M.W : 305.34 Pubchem ID :8213
Synonyms :

Calculated chemistry of [ 112-82-3 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 14
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 86.9
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -1.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.94
Log Po/w (XLOGP3) : 9.22
Log Po/w (WLOGP) : 6.86
Log Po/w (MLOGP) : 5.89
Log Po/w (SILICOS-IT) : 6.81
Consensus Log Po/w : 6.74

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.62
Solubility : 0.0000736 mg/ml ; 0.000000241 mol/l
Class : Poorly soluble
Log S (Ali) : -9.12
Solubility : 0.000000232 mg/ml ; 0.0000000008 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -7.18
Solubility : 0.0000203 mg/ml ; 0.0000000665 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.2

Safety of [ 112-82-3 ]

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 [ 112-82-3 ]

* 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 [ 112-82-3 ]
  • Downstream synthetic route of [ 112-82-3 ]

[ 112-82-3 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 36653-82-4 ]
  • [ 112-82-3 ]
YieldReaction ConditionsOperation in experiment
99% With ethyl 2,2-dibromoacetoacetate; triphenylphosphine In dichloromethane at 20℃; for 0.25 h; General procedure: Ethyl α,α-dibromoacetoacetate 2a (0.41 mmol, 1.2 equiv), alcohols 1a-1s (0.34 mmol, 1.0 equiv) and Ph3P (0.68 mmol, 2.0 equiv) were added under ambient temperature to 3 mL of DCE in air. After stirred at room temperature for appropriate time (monitored by TLC), the reaction was quenched by addition of H2O (3 mL) and then extracted with ethyl acetate (3×3 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography on silica gel with petroleum ether or mixture of petroleum ether and ethyl acetate as eluent to afford the corresponding products 3a-3s.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 1, p. 90 - 93
[2] Chemistry and Physics of Lipids, 1993, vol. 66, # 3, p. 161 - 170
[3] JAOCS, Journal of the American Oil Chemists' Society, 1996, vol. 73, # 7, p. 847 - 850
[4] Journal of the American Pharmaceutical Association (1912-1977), vol. 38, p. 288[5] Chem.Abstr., 1949, p. 8610
[6] Bulletin de la Societe Chimique de France, 1939, vol. <5> 6, p. 1670,1674
[7] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1943, vol. 279, p. 76,83
[8] Journal of the American Chemical Society, 1947, vol. 69, p. 236
[9] Chemische Berichte, 1943, vol. 76, p. 591
[10] Journal of the Chemical Society, 1948, p. 642[11] Journal of the Chemical Society, 1934, p. 339
[12] Pr.S.Dakota Acad., 1939, vol. 19, p. 124[13] Chem.Abstr., 1940, p. 2784
[14] Helvetica Chimica Acta, 1937, vol. 20, p. 1466,1467
[15] Chemische Berichte, 1936, vol. 69, p. 1766,1769,1784
[16] Chemische Berichte, 1934, vol. 67, p. 1122
[17] Gazzetta Chimica Italiana, 1950, vol. 80, p. 180,183
[18] Journal of the American Chemical Society, 1916, vol. 38, p. 1076
[19] Tetrahedron Letters, 1978, p. 4483 - 4486
[20] Journal fuer Praktische Chemie (Leipzig), 1960, vol. 10, p. 265 - 289
[21] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1979, p. 712 - 718
[22] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 16, p. 2663 - 2665
[23] Advanced Synthesis and Catalysis, 2016, vol. 358, # 21, p. 3394 - 3413
  • 2
  • [ 66143-65-5 ]
  • [ 112-82-3 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, p. 7108
  • 3
  • [ 4860-03-1 ]
  • [ 112-82-3 ]
Reference: [1] Synthetic Communications, 1984, vol. 14, # 14, p. 1313 - 1320
  • 4
  • [ 52756-05-5 ]
  • [ 63758-87-2 ]
  • [ 1950-69-2 ]
  • [ 112-82-3 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 24, p. 4097 - 4102
  • 5
  • [ 146404-40-2 ]
  • [ 1950-69-2 ]
  • [ 112-82-3 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 43, p. 7911 - 7914
  • 6
  • [ 83486-05-9 ]
  • [ 32294-60-3 ]
  • [ 112-82-3 ]
Reference: [1] Chemistry Letters, 1982, p. 1081 - 1084
  • 7
  • [ 143-27-1 ]
  • [ 112-82-3 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 43, p. 7911 - 7914
  • 8
  • [ 18049-99-5 ]
  • [ 112-82-3 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 43, p. 7911 - 7914
  • 9
  • [ 58587-19-2 ]
  • [ 112-82-3 ]
Reference: [1] Synthetic Communications, 1976, vol. 6, p. 21 - 26
  • 10
  • [ 66143-69-9 ]
  • [ 112-82-3 ]
Reference: [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 21, p. 3394 - 3413
  • 11
  • [ 7307-53-1 ]
  • [ 112-82-3 ]
Reference: [1] Synthesis, 1978, p. 771 - 773
  • 12
  • [ 20779-14-0 ]
  • [ 112-82-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 16, p. 2663 - 2665
  • 13
  • [ 57-09-0 ]
  • [ 112-82-3 ]
  • [ 75-50-3 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 7, p. 2143 - 2152
  • 14
  • [ 1190-63-2 ]
  • [ 10035-10-6 ]
  • [ 112-82-3 ]
Reference: [1] Helvetica Chimica Acta, 1937, vol. 20, p. 1466,1467
  • 15
  • [ 112-82-3 ]
  • [ 1454-85-9 ]
Reference: [1] Bl.Mat.grasses Marseille, 1929, p. 199[2] Chem. Zentralbl., 1929, vol. 100, # II, p. 2278
  • 16
  • [ 112-82-3 ]
  • [ 504-63-2 ]
  • [ 23377-40-4 ]
YieldReaction ConditionsOperation in experiment
88.4% With potassium hydroxide In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 16 h; In a 1000ml round bottom flask,Add n-hexadecyl bromide (2) 97.5 g (0.32 mol, 1 eq), 1,3-propanediol (3) 73.5 g (0.96 mol, 3 eq),DMSO 200ml,DMF 200ml andPotassium hydroxide 72g (1.28mol, 4eq), stirred at room temperature16h.After completion of the reaction, 500 ml of water was added to the reaction solution, then the pH was adjusted to neutrality with a 5M hydrochloric acid solution, and the mixture was extracted with ethyl acetate (500 ml×2). The organic layers were combined and the organic layer was washed with saturated brine (500 ml×2). ), collecting organic phase,Dry with 10 g of anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure to obtain 102 g of a yellow solid.Recrystallization of petroleum ether yielded 85 g of white flake-like crystals with a yield of 88.4percent.
77%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; oil at 0 - 20℃; for 0.166667 h;
Stage #2: With potassium iodide In N,N-dimethyl-formamide; oil at 95℃; for 4 h;
General procedure: To a solution of 1,3-propanediol (19) (6.51 mL, 90 mmol) in dry DMF (40 mL) was added NaH (60percent oil dispersion; 1.20 g, 30 mmol) in installments at 0 °C and the mixture was stirred at room temperature for 10 min. Dodecyl bromide (4.80 mL, 20 mmol) and KI (3.32 g, 20 mmol) were added and the mixture was heated at 95 °C for 4 h. After cooling, the mixture was poured into ice-water and extracted with AcOEt. The extracts were washed with brine, dried over Na2SO4 and evaporated. The resulting residue was purified by flash CC (silica gel; AcOEt/hexane, 1:2) to provide dodecyl ether 20a (3.38 g, 69percent). Tetradecyl ether 20b (79percent) and hexadecyl ether 20c (77percent) were similarly prepared from 1,3-propanediol (19).
Reference: [1] Patent: CN107936059, 2018, A, . Location in patent: Paragraph 0011; 0029; 0030
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3658 - 3665
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2002, vol. 177, # 12, p. 2887 - 2893
[4] Chemistry and Physics of Lipids, 1996, vol. 83, # 1, p. 77 - 85
[5] Molecular Therapy - Nucleic Acids, 2017, vol. 8, p. 158 - 168
  • 17
  • [ 112-82-3 ]
  • [ 75-50-3 ]
  • [ 57-09-0 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1955, p. 634
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 5108
[3] Bulletin de la Societe Chimique de France, 1955, p. 634
[4] Journal of the American Chemical Society, 1951, vol. 73, p. 5108
[5] Journal of Physical Chemistry, 1941, vol. 45, p. 954,958
[6] Journal of the American Chemical Society, 1943, vol. 65, p. 693
[7] Journal of Physical Chemistry, 1984, vol. 88, # 21, p. 5093 - 5099
[8] Journal of Physical Chemistry, 1993, vol. 97, # 39, p. 10236 - 10244
[9] Bulletin of the Chemical Society of Japan, 2011, vol. 84, # 3, p. 312 - 319
  • 18
  • [ 110-86-1 ]
  • [ 112-82-3 ]
  • [ 140-72-7 ]
YieldReaction ConditionsOperation in experiment
75% for 24 h; Reflux General procedure: 1-Bromohexadecane (0.01 mol) and a tertiary amine, N-benzyl-N,N-dimethylamine or pyridine, respectively (0.011 mol) were added to 25 ml of dry acetonitrile and heated at reflux for 24 h. Solvent was evaporated, the residue was co-evaporated with benzene and crystallized from acetone.
Reference: [1] Molecules, 2010, vol. 15, # 3, p. 1967 - 1972
[2] Green Chemistry, 2009, vol. 11, # 1, p. 83 - 90
[3] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 46 - 55
[4] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1952, vol. 291, p. 1,4
[5] Journal of the American Pharmaceutical Association (1912-1977), 1942, vol. 31, p. 51
[6] Journal of Physical Chemistry, 1983, vol. 87, # 22, p. 4417 - 4425
[7] Journal of Physical Chemistry, 1986, vol. 90, # 21, p. 5258 - 5265
[8] Tetrahedron, 2010, vol. 66, # 6, p. 1352 - 1356
[9] Journal of Surfactants and Detergents, 2012, vol. 15, # 5, p. 587 - 592
[10] Farmacia Bukarest, 1958, vol. 6, p. 305,308[11] Chem.Abstr., 1959, p. 2535
  • 19
  • [ 872-31-1 ]
  • [ 112-82-3 ]
  • [ 119269-24-8 ]
Reference: [1] Dalton Transactions, 2003, # 24, p. 4762 - 4769
  • 20
  • [ 2840-28-0 ]
  • [ 112-82-3 ]
  • [ 143269-74-3 ]
YieldReaction ConditionsOperation in experiment
83% With potassium hydroxide; benzyltriethylammonium bromide In water; xylene at 115 - 120℃; for 3 h; Example 5; n-Hexadecyl-3-amino-4-chlorobenzoate: A mixture of 16.3 g (0.132 moles) 45percent potassium hydroxide solution, 21.5 g (0.125 moles) of 3-amino-4-chlorobenzoic acid, 100 g of xylene, 40/3 g (0.132 moles) of 1-bromohexadecane and 4.5 g of benzyltriethylammonium bromide (10 mole percent) were heated to reflux and water was removed by means of a Dean Stark trap. After 3 hr at reflux (115-120° C.) the reaction was judged complete by tic. The reaction was cooled to 90° C. and washed with water to remove salts. The solvent was removed on a roto-vap and the residue was crystallized from heptane to give 40.7 g (83percent yield) of a solid judged to be pure by nmr and by tic.
99.6 %Spectr. With potassium hydroxide; tetrabutyl phosphonium bromide In water; 4-methyl-2-pentanone at 115 - 120℃; for 5 h; Example 3; n-Hexadecyl-3-amino-4-chlorobenzoate: A mixture of 32.7 g (0.264 moles) 45percent potassium hydroxide solution, 43 g (0.25moles) of 3-amino-4-chlorobenzoic acid, 200 g of methyl isobutyl ketone, 80.6g (0.264 moles) of 1-bromohexadecane and 4.4 g of tetrabutylphosphonium bromide (5 mole percent) were heated to reflux and water was removed by means of a Dean Stark trap. After 5 hr at reflux (115-120° C.) the reaction was judged complete by tic. The reaction was cooled to 90° C. and washed with water to remove salts. The solvent was removed on a roto-vap and the residue was crystallized from heptane to give 93.4 g (95percent yield) of a solid whose nmr weight percent assay was 99.6percent.
Reference: [1] Patent: US2006/135807, 2006, A1, . Location in patent: Page/Page column 3
[2] Patent: US2006/135807, 2006, A1, . Location in patent: Page/Page column 2
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