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[ CAS No. 7499-08-3 ] {[proInfo.proName]}

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Chemical Structure| 7499-08-3
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Product Details of [ 7499-08-3 ]

CAS No. :7499-08-3 MDL No. :MFCD00053312
Formula : C8H7ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HXGHMCLCSPQMOR-UHFFFAOYSA-N
M.W : 170.59 Pubchem ID :82010
Synonyms :

Calculated chemistry of [ 7499-08-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.38
TPSA : 37.3 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) : -5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 2.44
Log Po/w (WLOGP) : 2.35
Log Po/w (MLOGP) : 2.52
Log Po/w (SILICOS-IT) : 2.31
Consensus Log Po/w : 2.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.288 mg/ml ; 0.00169 mol/l
Class : Soluble
Log S (Ali) : -2.87
Solubility : 0.232 mg/ml ; 0.00136 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.77
Solubility : 0.29 mg/ml ; 0.0017 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.19

Safety of [ 7499-08-3 ]

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 [ 7499-08-3 ]

* 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 [ 7499-08-3 ]
  • Downstream synthetic route of [ 7499-08-3 ]

[ 7499-08-3 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 608-23-1 ]
  • [ 64-19-7 ]
  • [ 7499-08-3 ]
YieldReaction ConditionsOperation in experiment
60% at 100 - 105℃; for 1 h; Autoclave 280 g of 3-chloro-o-xylene (2 mol), 28 g of acetic acid and 0.28 g ofcobalt-manganese bromide composite catalystwere added to a 500 ml autoclave(the catalyst included 0.136 g of cobalt acetate tetrahydrate, 0.105 g of manganese acetate tetrahydrate and0.039g ofpotassium bromide) , Stirring, heating to 100 ~ 105 .Slowly through the oxygen so that the pressure inside the kettle to0.1Mpa, oxygen into the way intermittent oxygen, the control of the internal temperature of 100 ~ 105 , about 1h pass.The concentrate wascooledto -0.095Mpa and the solvent was distilled off (the distillate was mainly acetic acid and can be recovered). The concentrate wascooled, filtered and dried to obtain 203.8 g of 2-methyl-3-chlorobenzoic acid, 98.5percent purity,60percent.
Reference: [1] Patent: CN106946685, 2017, A, . Location in patent: Paragraph 0040-0041; 0044; 0047; 0050; 0052
  • 2
  • [ 535-80-8 ]
  • [ 74-88-4 ]
  • [ 7499-08-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 10, p. 1265 - 1272
[2] Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 2030 - 2033
  • 3
  • [ 118-90-1 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
  • [ 133232-56-1 ]
  • [ 54811-38-0 ]
YieldReaction ConditionsOperation in experiment
38% With sulfuric acid; Iodine monochloride; periodic acid In water; acetic acid at 90℃; for 5.66667 h; Suspended in a 100 mL three-necked flask equipped with a reflux condenser were 25 mL of 30 weight percent sulfuric acid and 1.36 g (10 mmol) of 2-methylbenzoic acid, and 2.4 g (15 mmol) of iodine monochloride dissolved in 5 g of acetic acid was dropwise added thereto in 40 minutes. Reaction was carried out at 90°C for 5 hours, and the reaction mixture was poured into 90 mL of water. The precipitate was filtered and washed with a sodium sulfite aqueous solution to obtain a crystalline solid (yield: 1.6 g) as the product. This solid was analyzed to find that the product showed the following distribution: [] 2-methylbenzoic acid33 percent5-chloro-2-methylbenzoic acid13 percent3- chloro -2-methylbenzoic acid9 percent5-iodo-2-methylbenzoic acid38 percent3-iodo-2-methylbenzoic acid5 percentothers2 percent The above mixture was purified by recrystallization using acetic acid or isopropyl alcohol to try to isolate 5-iodo-2-methylbenzoic acid. However, a purity of the mixture was scarcely improved, and it was difficult to obtain 5-iodo-2-methylbenzoic acid.
Reference: [1] Patent: EP1595862, 2005, A1, . Location in patent: Page/Page column 11-12
  • 4
  • [ 146516-69-0 ]
  • [ 7499-08-3 ]
Reference: [1] Monatshefte fuer Chemie, 1992, vol. 123, # 12, p. 1125 - 1134
  • 5
  • [ 205178-79-6 ]
  • [ 7499-08-3 ]
Reference: [1] Pesticide Science, 1994, vol. 41, # 2, p. 139 - 148
  • 6
  • [ 611-19-8 ]
  • [ 7499-08-3 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, p. 334 - 343
  • 7
  • [ 54454-12-5 ]
  • [ 7499-08-3 ]
Reference: [1] Chemische Berichte, 1904, vol. 37, p. 1021
[2] Pesticide Science, 1994, vol. 41, # 2, p. 139 - 148
  • 8
  • [ 87-60-5 ]
  • [ 7499-08-3 ]
Reference: [1] Pesticide Science, 1994, vol. 41, # 2, p. 139 - 148
[2] Chemische Berichte, 1904, vol. 37, p. 1021
  • 9
  • [ 30515-50-5 ]
  • [ 7499-08-3 ]
Reference: [1] Journal of Organic Chemistry, 1960, vol. 25, p. 334 - 343
  • 10
  • [ 118-90-1 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
[2] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 308
[3] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
[4] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
  • 11
  • [ 83-42-1 ]
  • [ 7499-08-3 ]
Reference: [1] Chemische Berichte, 1904, vol. 37, p. 1021
  • 12
  • [ 56043-01-7 ]
  • [ 7499-08-3 ]
Reference: [1] Chemische Berichte, 1904, vol. 37, p. 1021
  • 13
  • [ 608-23-1 ]
  • [ 7697-37-2 ]
  • [ 7499-08-3 ]
Reference: [1] Chemische Berichte, 1885, vol. 18, p. 1759
[2] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 308
  • 14
  • [ 118-90-1 ]
  • [ 7782-50-5 ]
  • [ 64-19-7 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 308
  • 15
  • [ 118-90-1 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
  • [ 133232-56-1 ]
  • [ 54811-38-0 ]
YieldReaction ConditionsOperation in experiment
38% With sulfuric acid; Iodine monochloride; periodic acid In water; acetic acid at 90℃; for 5.66667 h; Suspended in a 100 mL three-necked flask equipped with a reflux condenser were 25 mL of 30 weight percent sulfuric acid and 1.36 g (10 mmol) of 2-methylbenzoic acid, and 2.4 g (15 mmol) of iodine monochloride dissolved in 5 g of acetic acid was dropwise added thereto in 40 minutes. Reaction was carried out at 90°C for 5 hours, and the reaction mixture was poured into 90 mL of water. The precipitate was filtered and washed with a sodium sulfite aqueous solution to obtain a crystalline solid (yield: 1.6 g) as the product. This solid was analyzed to find that the product showed the following distribution: [] 2-methylbenzoic acid33 percent5-chloro-2-methylbenzoic acid13 percent3- chloro -2-methylbenzoic acid9 percent5-iodo-2-methylbenzoic acid38 percent3-iodo-2-methylbenzoic acid5 percentothers2 percent The above mixture was purified by recrystallization using acetic acid or isopropyl alcohol to try to isolate 5-iodo-2-methylbenzoic acid. However, a purity of the mixture was scarcely improved, and it was difficult to obtain 5-iodo-2-methylbenzoic acid.
Reference: [1] Patent: EP1595862, 2005, A1, . Location in patent: Page/Page column 11-12
  • 16
  • [ 118-90-1 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
[2] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 308
[3] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
[4] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 311
  • 17
  • [ 118-90-1 ]
  • [ 7782-50-5 ]
  • [ 64-19-7 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 274, p. 308
  • 18
  • [ 7499-08-3 ]
  • [ 603-80-5 ]
Reference: [1] Patent: US6124500, 2000, A,
  • 19
  • [ 7499-08-3 ]
  • [ 603-80-5 ]
Reference: [1] Patent: US6124500, 2000, A,
  • 20
  • [ 118-90-1 ]
  • [ 7499-08-3 ]
  • [ 7499-06-1 ]
  • [ 133232-56-1 ]
  • [ 54811-38-0 ]
YieldReaction ConditionsOperation in experiment
38% With sulfuric acid; Iodine monochloride; periodic acid In water; acetic acid at 90℃; for 5.66667 h; Suspended in a 100 mL three-necked flask equipped with a reflux condenser were 25 mL of 30 weight percent sulfuric acid and 1.36 g (10 mmol) of 2-methylbenzoic acid, and 2.4 g (15 mmol) of iodine monochloride dissolved in 5 g of acetic acid was dropwise added thereto in 40 minutes. Reaction was carried out at 90°C for 5 hours, and the reaction mixture was poured into 90 mL of water. The precipitate was filtered and washed with a sodium sulfite aqueous solution to obtain a crystalline solid (yield: 1.6 g) as the product. This solid was analyzed to find that the product showed the following distribution: [] 2-methylbenzoic acid33 percent5-chloro-2-methylbenzoic acid13 percent3- chloro -2-methylbenzoic acid9 percent5-iodo-2-methylbenzoic acid38 percent3-iodo-2-methylbenzoic acid5 percentothers2 percent The above mixture was purified by recrystallization using acetic acid or isopropyl alcohol to try to isolate 5-iodo-2-methylbenzoic acid. However, a purity of the mixture was scarcely improved, and it was difficult to obtain 5-iodo-2-methylbenzoic acid.
Reference: [1] Patent: EP1595862, 2005, A1, . Location in patent: Page/Page column 11-12
  • 21
  • [ 7499-08-3 ]
  • [ 74-85-1 ]
  • [ 628732-10-5 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With thionyl chloride In benzeneHeating / reflux
Stage #2: With aluminum (III) chloride In 1,1-dichloroethane at 10 - 20℃;
Stage #3: With sulfuric acid In water at 85℃; for 1 h;
Example NINETEEN-4 (Compound 152) Thionyl chloride (10.0 [ML,] 1.5 eq) and 3-chloro-2-methyl-benzoic acid (commercially available from Aldrich) (15.6 g, 91.4 mmol) in benzene was refluxed until no more gas evolution was observed. After cooling to rt the mixture was concentrated. The concentrate was diluted with dichloroethane and added to a solution [OF OF ALCL3] (12.2 g, 1.0 [EQ)] in dichloroethane at [10-20 °C. ETHYLENE WAS] bubbled through the mixture for 4 h. and the mixture was stirred overnight. The mixture was quenched with 4 N [HC1.] The resulting layers were separated and the aqueous layer was extracted with [ET20] (3 x 250 mL). The combined organic extract was washed with [H20] (3 x 150 mL), saturated [NAHC03] (3 x 150 mL), brine (1 [X] 150 mL), dried over MgS04 and concentrated. Concentrated sulfuric acid was added and the mixture was stirred at [85 °C FOR] 1 h. After cooling to rt, the reaction mixture was quenched with ice-water. The mixture was extracted with Et2O (3 x 250 mL) and the combined organic extracts were washed with [H20] (3 x 200 mL), saturated [NAHC03] (3 x 200 mL), brine (1 x 100 mL), dried over MgS04 and concentrated. Pure 6-chloro-7- methyl-l-indanone (11.9 g, 72percent) was obtained after column chromatography using 20 percent EtOAc: hexane as eluant. Use [OF 6-CHLORO-7-METHYL-1-INDANONE] in Method NINETEEN produced 4- (5-chloro-4-methyl-indan-2-yl)-1, 3-dihydro-imidazole-2- thione (Compound 152). [1H] NMR (300 MHz, [MEOH-D4)] 8 7.16 (d, J= 8.5 Hz, 1H), 7.02 (d, J= 8.5 Hz, [1H),] 6.62 (s, 1H), 3.59-3. 52 (m, 1H), 3.31-3. 24 (m, 2H), 3.00-2. 92 (m, 2H), 2.30 (s, 3H).
Reference: [1] Patent: WO2003/99795, 2003, A1, . Location in patent: Page 112
  • 22
  • [ 7499-08-3 ]
  • [ 45514-47-4 ]
  • [ 188187-03-3 ]
YieldReaction ConditionsOperation in experiment
82% for 18 h; Heating / reflux s) 2-Chloro-6-methyl carboxylate benzylbromide To a solution of methyl 3-chloro-2-methylbenzoate (1.30 g, 7.04 mmol) in benzene (20 mL) was added NBS (1.50 g. 8.45 mmol) and benzoyl peroxide (0.20 g, 0.83 mmol). After stirring at reflux for 18 h, the mixture was poured into water, and the resulting mixture was extracted with ethyl acetate (3.x.50 mL). The combined organic extracts were washed with brine and dried (Na2SO4). After removing the solvent under reduced pressure, flash column chromatography (1:1 ether/hexane) of the residue gave 1.87 g (82percent) of the title compound as a dark oil: 1H NMR (250 MHz CDCl3) d 7.72 (d, 1H), 7.55 (d, 1H), 7.21 (t, 1H), 5.09 (s, 2H), 3.92 (s, 3H).
Reference: [1] Patent: US6353116, 2002, B1, . Location in patent: Page column 24
  • 23
  • [ 7499-08-3 ]
  • [ 188187-03-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365
[2] Patent: US2013/65925, 2013, A1,
[3] Patent: EP2757103, 2014, A1,
[4] Patent: WO2005/16913, 2005, A1,
[5] Patent: WO2005/121130, 2005, A2,
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