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Product Details of [ 2840-28-0 ]

CAS No. :2840-28-0 MDL No. :MFCD00007671
Formula : C7H6ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DMGFVJVLVZOSOE-UHFFFAOYSA-N
M.W : 171.58 Pubchem ID :76092
Synonyms :

Calculated chemistry of [ 2840-28-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.82
TPSA : 63.32 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) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.16
Log Po/w (XLOGP3) : 1.82
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 0.48
Log Po/w (SILICOS-IT) : 1.14
Consensus Log Po/w : 1.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.39
Solubility : 0.702 mg/ml ; 0.00409 mol/l
Class : Soluble
Log S (Ali) : -2.77
Solubility : 0.292 mg/ml ; 0.0017 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.02
Solubility : 1.63 mg/ml ; 0.00948 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 2840-28-0 ]

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 [ 2840-28-0 ]

* 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 [ 2840-28-0 ]
  • Downstream synthetic route of [ 2840-28-0 ]

[ 2840-28-0 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 2840-28-0 ]
  • [ 42860-04-8 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 2, p. 463 - 471
[2] Patent: US2002/19527, 2002, A1,
  • 2
  • [ 2840-28-0 ]
  • [ 79406-57-8 ]
Reference: [1] Chemistry - An Asian Journal, 2015, vol. 10, # 6, p. 1286 - 1290
  • 3
  • [ 40872-87-5 ]
  • [ 2840-28-0 ]
YieldReaction ConditionsOperation in experiment
72.01%
Stage #1: With water; lithium hydroxide In tetrahydrofuran at 20℃; for 12 h;
Stage #2: at 0℃;
To a stirred solution of 3-amino-4-chloro-benzoic acid methyl ester (0.300 g, 1.62 mmol) in tetrahydrofuran (20 mL) was added a solution of lithium hydroxide (0.340 g, 8.10 mmol) in water (5 mL) and reaction was stirred at room temperature for 12 hours (monitored by silica TLC; ethyl acetate-hexanes, 1:1).
Solvent was distilled off under reduced pressure; the obtained lithium salt was acidified with citric acid [1percent (w/v)] solution at 0° C. and was extracted (2*20 mL).
Collected organic parts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 3-amino-4-chloro-benzoic acid as white solid. (Yield 0.200 g, 72.01percent).
Reference: [1] Patent: US2012/184548, 2012, A1, . Location in patent: Page/Page column 43
  • 4
  • [ 96-99-1 ]
  • [ 2840-28-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1868, vol. 147, p. 258
[2] Journal of the Indian Chemical Society, 1959, vol. 36, p. 99,101
[3] Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1306 - 1316
[4] Applied Catalysis A: General, 2017, vol. 537, p. 50 - 58
  • 5
  • [ 111-48-8 ]
  • [ 96-99-1 ]
  • [ 2840-28-0 ]
Reference: [1] Patent: US4059627, 1977, A,
  • 6
  • [ 101870-46-6 ]
  • [ 2840-28-0 ]
Reference: [1] Chemische Berichte, 1902, vol. 35, p. 3706
  • 7
  • [ 1843-35-2 ]
  • [ 2840-28-0 ]
  • [ 89-54-3 ]
Reference: [1] Chemische Berichte, 1886, vol. 19, p. 314
[2] Chemische Berichte, 1902, vol. 35, p. 3718
  • 8
  • [ 7647-01-0 ]
  • [ 1843-35-2 ]
  • [ 2840-28-0 ]
  • [ 89-54-3 ]
Reference: [1] Chemische Berichte, 1886, vol. 19, p. 314
[2] Chemische Berichte, 1902, vol. 35, p. 3718
  • 9
  • [ 1843-35-2 ]
  • [ 2840-28-0 ]
  • [ 89-54-3 ]
Reference: [1] Chemische Berichte, 1886, vol. 19, p. 314
[2] Chemische Berichte, 1902, vol. 35, p. 3718
  • 10
  • [ 7647-01-0 ]
  • [ 1843-35-2 ]
  • [ 2840-28-0 ]
  • [ 89-54-3 ]
Reference: [1] Chemische Berichte, 1886, vol. 19, p. 314
[2] Chemische Berichte, 1902, vol. 35, p. 3718
  • 11
  • [ 2840-28-0 ]
  • [ 42860-10-6 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 2, p. 463 - 471
  • 12
  • [ 67-56-1 ]
  • [ 2840-28-0 ]
  • [ 40872-87-5 ]
YieldReaction ConditionsOperation in experiment
100% at 0℃; for 12 h; Reflux Example 1118-Chloro-3,3-dimethyl-2-(3-morpholin-4-yl-phenyl)-l,2,3>4-tetrahydro-quinoline-5- carboxylic acidTo a stirred solution of 3-amino-4-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropewise at 0°C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3 x 100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-amino-4-chloro- benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8C1N02 (M+H)+: 186.61, observed: 185.9.
100% at 0℃; for 12 h; Reflux To a stirred solution of 3-amino-4-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropewise at 0° C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3.x.100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-amino-4-chloro-benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8ClNO2 (M+H)+: 186.61, observed: 185.9.
92.5% for 12 h; Reflux Methyl 3-amino-4-chlorobenzoate (1). To a solution of 3-amino-4-chlorobenzoic acid (15.0 g, 88.0 mmol) in methanol (90.0 mL), thionyl chloride (13.0 mL) was added drop- wise at 0 °C. The resulting mixture was refluxed for 12h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was diluted with water (150 mL), and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate solution (50 mL), brine solution (50 mL) and finally dried over sodium sulfate. The organic layer was removed under rotary evaporator to yield 1 (15.0 g, 92.5percent) as an off-white solid. 1H NMR (400 MHz, CDC13) δ 3.88 (s, 3H), 4.26 (brs, 2H), 7.29 (d, J = 8.2 Hz, 1H), 7.34-7.37 (dd, J = 1.9, 8.2 Hz, 1H), 7.45 (d, J = 1.9 Hz, 1H).
Reference: [1] Patent: WO2011/128251, 2011, A1, . Location in patent: Page/Page column 201
[2] Patent: US2011/257151, 2011, A1, . Location in patent: Page/Page column 74
[3] Patent: WO2014/149164, 2014, A1, . Location in patent: Paragraph 00708
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2465 - 2481
[5] Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 2051 - 2053
[6] Patent: WO2015/84606, 2015, A1, . Location in patent: Page/Page column 115
[7] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2423 - 2435
  • 13
  • [ 74-87-3 ]
  • [ 2840-28-0 ]
  • [ 40872-87-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 22, p. 7815 - 7833
  • 14
  • [ 2840-28-0 ]
  • [ 67-64-1 ]
  • [ 73177-33-0 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 8, p. 1546 - 1547
  • 15
  • [ 2840-28-0 ]
  • [ 117738-76-8 ]
YieldReaction ConditionsOperation in experiment
80% With hydrogenchloride; potassium cyanide; sodium nitrite In water EXAMPLE 44A
3-Cyano-4-chloro-benzoic acid
3-Amino-4-chlorobenzoic acid (18.72 g, 109.1 mmol), commercially available, was added to a mixture of water (200 mL) and 37percent HCl (35 mL), and the resulting slurry was cooled to 5° C. A solution of NaNO2 (8.65 g, 125 mmol) in water (70 mL) was added dropwise, and the solution stirred at 5° C for 30 min.
The solution was then added to a slurry consisting of water (400 mL), CuCN (9.85 g, 109 mmol),and KCN(12.06g, 185 mmol), while maintaining the temperature at5°-10° C.
The mixture was stirred at 10° C. for another 30 min, and then heated to 80° C. for 1 hour.
The reaction was cooled, and the pH adjusted to ~1 by addition of concentrated HCl.
The solution was extracted with 5* CHCl3, and the combined extracts were rinsed with 1M HCl and brine, and dried over MgSO4.
The solvent was removed in vacuo, and the crude product was recrystallized from CHCl3 /EtOAc to yield 15.9 g (80percent) of the title compound. m.p. 180° C. 1 H NMR (300 MHz, CDCl3) δ 10.55 (br s, 1H), 8.42 (d, 1H), 8.26 (dd, 1H), 7.68 (d, 1H). MS (DCI/NH3) m/e 213 (M+NH4)+.
Reference: [1] Patent: US5597823, 1997, A,
[2] Patent: EP279698, 1990, A3,
  • 16
  • [ 773837-37-9 ]
  • [ 2840-28-0 ]
  • [ 117738-76-8 ]
YieldReaction ConditionsOperation in experiment
22% With hydrogenchloride; copper(l) cyanide; sodium nitrite In water at 5 - 40℃; for 4 h; CuCN (9.58 g, 107 mmol) was suspended in 80 mL of water. NaCN (14.7 g, 300 mmol) was added with vigorous stirring and the internal temperature was kept below 40 °C until all the CuCN went into solution. A suspension of 31 (15 g, 87.7 mmol) in water (150 mL) and concentrated HCl (24.8 mL) was cooled in an ice bath to 5 °C. A solution of NaNO2 (7.7 g, 111 mmol) in water (24 mL) was added dropwise at such a rate as to maintain the temperature around 5 °C. When all the NaNO2 was added, the solution was slowly introduced through an ice-cooled dropping funnel into the reactor containing the NaCN/CuCN solution with an exhaust into 1 M NaOH solution. After 4 h the reaction mixture was slowly and carefully nevtralized with solid Na2CO3 and then extracted with ethylacetate (3x150 mL). Organic phase was dried over Na2SO4 and evaporated under reduced pressure to obtain compound 32.
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 64, p. 302 - 313
  • 17
  • [ 2840-28-0 ]
  • [ 151-50-8 ]
  • [ 117738-76-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 8, p. 1586 - 1603
  • 18
  • [ 2840-28-0 ]
  • [ 503816-69-1 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 2051 - 2053
[2] Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 2051 - 2053
  • 19
  • [ 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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