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Product Details of [ 99-04-7 ]

CAS No. :99-04-7 MDL No. :MFCD00002523
Formula : C8H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GPSDUZXPYCFOSQ-UHFFFAOYSA-N
M.W : 136.15 Pubchem ID :7418
Synonyms :

Calculated chemistry of [ 99-04-7 ]

Physicochemical Properties

Num. heavy atoms : 10
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 : 38.37
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) : -5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 2.37
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.93
Log Po/w (SILICOS-IT) : 1.68
Consensus Log Po/w : 1.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.379 mg/ml ; 0.00278 mol/l
Class : Soluble
Log S (Ali) : -2.79
Solubility : 0.219 mg/ml ; 0.00161 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.13
Solubility : 1.02 mg/ml ; 0.00746 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 99-04-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 99-04-7 ]

* 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 [ 99-04-7 ]
  • Downstream synthetic route of [ 99-04-7 ]

[ 99-04-7 ] Synthesis Path-Upstream   1~56

  • 1
  • [ 1694-82-2 ]
  • [ 19438-61-0 ]
  • [ 19438-60-9 ]
  • [ 99-94-5 ]
  • [ 99-04-7 ]
Reference: [1] Journal of applied chemistry of the USSR, 1987, vol. 60, # 1 pt 2, p. 136 - 138
[2] Journal of applied chemistry of the USSR, 1987, vol. 60, # 1 pt 2, p. 136 - 138
  • 2
  • [ 99-04-7 ]
  • [ 19181-53-4 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
[2] Chemische Berichte, 1905, vol. 38, p. 3555
[3] Chemische Berichte, 1905, vol. 38, p. 3555
  • 3
  • [ 99-04-7 ]
  • [ 19181-54-5 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
  • 4
  • [ 79-19-6 ]
  • [ 99-04-7 ]
  • [ 76074-47-0 ]
Reference: [1] Journal of Chemical Research, 2014, vol. 38, # 6, p. 347 - 350
[2] Heterocyclic Communications, 2007, vol. 13, # 6, p. 387 - 392
[3] European Journal of Medicinal Chemistry, 2009, vol. 44, # 7, p. 2782 - 2786
[4] Journal of Chemical Research, 2009, # 11, p. 671 - 673
[5] Chinese Chemical Letters, 2010, vol. 21, # 3, p. 301 - 304
[6] Journal of Chemical Research, 2010, vol. 34, # 12, p. 719 - 721
[7] Synthetic Communications, 2011, vol. 41, # 6, p. 864 - 870
[8] Journal of Chemical Research, 2012, vol. 36, # 4, p. 218 - 221
[9] Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 4, p. 403 - 404
[10] RSC Advances, 2014, vol. 4, # 99, p. 55827 - 55831
[11] Letters in Drug Design and Discovery, 2015, vol. 12, # 4, p. 314 - 318
[12] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 599 - 613
[13] Pharmazie, 2018, vol. 73, # 3, p. 123 - 127
[14] Bioorganic Chemistry, 2018, vol. 81, p. 88 - 92
  • 5
  • [ 99-04-7 ]
  • [ 31719-77-4 ]
Reference: [1] Russian Journal of Organic Chemistry, 1995, vol. 31, # 8, p. 1084 - 1088[2] Zhurnal Organicheskoi Khimii, 1995, vol. 31, # 8, p. 1191 - 1196
[3] Russian Journal of Organic Chemistry, 1994, vol. 30, # 12, p. 1946 - 1980[4] Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 12, p. 1847 - 1881
[5] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 17, p. 2475 - 2478
  • 6
  • [ 99-04-7 ]
  • [ 6515-58-8 ]
YieldReaction ConditionsOperation in experiment
86% With N-Bromosuccinimide; dibenzoyl peroxide In dichloromethane for 2 h; Reflux Methylmethylbenzoic acid (2.0 g, 14.7 mmol)And benzoyl peroxide (BPO, 0.036 g, 0.15 mmol)Was dissolved in dichloromethane (6 mL) and heated to reflux,NBS (2.6 g, 14.7 mmol) was added in portions,Continue to heat reflux 2h,After cooling to room temperature, the reaction was quenched with water (10 mL), extracted with dichloromethane (50 mL), washed with water, washed with saturated NaCl, dried over anhydrous Na2SO4,Concentrated to give a pale yellow solid 2.7 g, yield 86percent
85% With N-Bromosuccinimide In tetrachloromethane at 25℃; for 3 h; Reflux To a suspension of 3-Methyl-benzoic acid (40.0 g, 293 mmol) in carbon tetrachloride (400 mL) were added AIBN (1 g, 0.58 mmol) and N-Bromosuccinamide (52.0 g, 8.07 mmol) at 25 °C. The reaction mixture was refluxed over a period of 3 h. The resulting reaction mixture was filtered when it was hot and the filtrate was diluted with ethyl acetate, washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain 3-Bromomethyl-benzoic acid as a colorless solid (54 g, 85 percent).
85% With N-Bromosuccinimide In tetrachloromethane at 25℃; for 3 h; Reflux To a suspension of 3-Methyl-benzoic acid (40.0 g, 293 mmol) in carbon tetrachloride (400 mL) were added AIBN (1 g, 0.58 mmol) and N-Bromosuccinamide (52.0 g, 8.07 mmol) at 25° C.
The reaction mixture was refluxed over a period of 3 h.
The resulting reaction mixture was filtered when it was hot and the filtrate was diluted with ethyl acetate, washed with water and dried over sodium sulphate.
The solvent was evaporated under reduced pressure to obtain 3-Bromomethyl-benzoic acid as a colorless solid (54 g, 85percent).
61% With N-Bromosuccinimide In chloroform for 2.75 h; 500 W quartz halogen lamp at 75percent power; Heating / reflux In a 1 L round bottom flask fitted with a reflux condenser, a stirred suspension of 10.00 g m-toluic acid and 14.37 g (1.1 eq.) N-bromosuccinimide in 735 mL chloroform was sparged for 0.5 h with nitrogen. The sparging was discontinued and the stirred suspension was irradiated under a nitrogen atmosphere using a 500 W quartz halogen lamp at 75percent power, causing the solids to dissolve and the reaction to reflux. The red color of the reaction became clear after 1.25 h, and another 14.37 g of N-bromosuccinimide was added. The reaction mixture was stirred and irradiated under nitrogen atmosphere with a 500 W quartz halogen lamp at 75percent power for another 1.5 h, at which time the solution was clear. The solvent volume was reduced in vacuo to about 100 mL, and then the solution was cooled to -20° C., forming crystals. The resultant suspension was vacuum filtered through a bed of dry silica, which was then eluted with 800 mL of chloroform. The chloroform filtrate volume was reduced in vacuo to about 100 mL, and then the chloroform was cooled to -20° C., forming crystals. The crystals were vacuum filtered and washed with 30 mL chloroformn and 50 mL hexanes, then dissolved in 250 mL chloroform and washed in a separatory funnel with 3.x.300 mL volumes of water, followed by one 300 mL volume of brine to remove traces of succinimide. The organic phase was dried over magnesium sulfate, vacuum filtered and concentrated in vacuo to provide 9.56 g (61percent) of Compound 17 as a white crystalline power.

Reference: [1] Patent: CN106366078, 2017, A, . Location in patent: Paragraph 0229; 0230; 0231
[2] Patent: WO2011/21209, 2011, A1, . Location in patent: Page/Page column 57; 58
[3] Patent: US2012/101099, 2012, A1, . Location in patent: Page/Page column 22
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 22, p. 7878 - 7889
[5] Collection of Czechoslovak Chemical Communications, 2004, vol. 69, # 12, p. 2239 - 2252
[6] Patent: US2007/72825, 2007, A1, . Location in patent: Page/Page column 32-33
[7] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 515[8] Chem. Zentralbl., 1914, vol. 85, # II, p. 1271
[9] Journal of the American Chemical Society, 1985, vol. 107, # 4, p. 898 - 909
[10] Organic letters, 2003, vol. 5, # 9, p. 1407 - 1410
[11] Tetrahedron Letters, 2007, vol. 48, # 15, p. 2679 - 2682
[12] Chemical Communications, 2013, vol. 49, # 95, p. 11155 - 11157
  • 7
  • [ 99-04-7 ]
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YieldReaction ConditionsOperation in experiment
80.5% With N-Bromosuccinimide In tetrachloromethane EXAMPLE 1
Preparation of 3-bromomethyl-benzoic acid
10 g (73.4 millimoles) of m-methyl-benzoic acid are dissolved in 75 ml of anhydrous carbon tetrachloride, whereupon 0.2 g of 2,2'-azo-bis-(2-methyl-propiontirile) and 13.72 g (77.07 millimoles) of N-bromo-succinimide are added.
The reaction mixture is refluxed for 20 minutes, the formed succinimide is removed by filtering the warm mixture.
The organic filtrate is washed with 15 ml of water, dried over sodium sulfate, filtered and the filtrate is evaporated in vacuo.
The crude product thus obtained is recrystallized from a fivefold amount of carbon tetrachloride.
Thus 12.71 g of the title compound are obtained, yield 80.5percent.
Analysis data:
Thin layer chromatography Rf =0.38 (a 1:1 mixture of benzene and ethyl acetate).
The Rf value of the methyl ester prepared by using diazomethane amounts to 0.38 (a 2:1 mixture of benzene-hexane).
1 H-NMR/CDCl3, δ/:4,51/s, 2H, CH2 / 7.25-7.6 (m, 2H, aromatic protons), 7.75-7.85 (m, 2H, aromatic protons).
Reference: [1] Patent: US4638002, 1987, A,
  • 8
  • [ 614-45-9 ]
  • [ 99-04-7 ]
  • [ 6515-58-8 ]
YieldReaction ConditionsOperation in experiment
53% With N-Bromosuccinimide In tetrachloromethane a)
3-bromomethylbenzoic Acid
A mixture of 3-toluic acid (15.0 g, 110 mmol), N-bromosuccinimide (19.60 g, 110 mmol) and t-butyl peroxybenzoate (2.1 mL, 110 mmol) in carbon tetrachloride (50 mL) was heated at reflux overnight.
The mixture was cooled and concentrated under reduced pressure.
The residue obtained was washed with carbon tetrachloride and filtered under vacuum.
The filtrate was evaporated to dryness to yield a white solid (12.57 g, 53percent).
1H NMR (400 MHz, CDCl3) d 7.93 (m, 2H), 7.43 (m, 2H), 4.55 (s, 2H).
Reference: [1] Patent: US2002/49316, 2002, A1,
  • 9
  • [ 128-08-5 ]
  • [ 99-04-7 ]
  • [ 123-56-8 ]
  • [ 6515-58-8 ]
YieldReaction ConditionsOperation in experiment
61% for 2.75 h; Irradiation; Heating / reflux Synthesis of 3-bromomethylbenzoic acid: In a 1 L round bottom flask fitted with a reflux condenser, a stirred suspension of 10.00 g of m-toluic acid and 14.37 g (1.1 eq.) N-bromosuccinimide in 735 mL chloroform was sparged for 0.5 h with nitrogen. The sparging was discontinued, and the suspension was stirred and irradiated under nitrogen atmosphere using a 500 W quartz halogen lamp at 75percent power, causing the solids to dissolve and the chloroform to reflux. The red color of the reaction mixture disappeared after 1.25 h, and 14.37 g of N-bromosuccinimide was added. The reaction mixture was stirred and irradiated under nitrogen atmosphere with a 500 W quartz halogen lamp at 75percent power for another 1.5 h, at which time the solution became colorless. The solvent volume was reduced in vacuo to about 100 mL, and then cooled to-20 °C. The resultant suspension was vacuum filtered through a bed of dry silica. The silica was washed with 800 mL of chloroform. The chloroform filtrate was reduced in vacuo to about 100 mL, and then cooled to-20 °C. The resultant crystals were vacuum filtered, washed with 30 mL of chloroform followed by 50 mL of hexanes, then dissolved in 250 mL chloroform and washed in a separatory funnel with 3 x 300 mL volumes of water followed by one 300 mL volume of brine to remove traces of succinimide. The organic phase was dried with magnesium sulfate, vacuum filtered, and the solvent was removed in vacuo to provide 9.56 g (61percent) of 3- bromomethylbenzoic acid as a white crystalline power.
Reference: [1] Patent: WO2005/97123, 2005, A2, . Location in patent: Page/Page column 79-80
  • 10
  • [ 128-08-5 ]
  • [ 99-04-7 ]
  • [ 6515-58-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 2, p. 457 - 480
  • 11
  • [ 75-25-2 ]
  • [ 7726-95-6 ]
  • [ 99-04-7 ]
  • [ 6515-58-8 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 515[2] Chem. Zentralbl., 1914, vol. 85, # II, p. 1271
  • 12
  • [ 99-04-7 ]
  • [ 1129-28-8 ]
Reference: [1] Patent: WO2011/21209, 2011, A1,
[2] Patent: US2012/101099, 2012, A1,
[3] Organic Letters, 2013, vol. 15, # 4, p. 917 - 919
[4] RSC Advances, 2013, vol. 3, # 45, p. 23119 - 23127
[5] Chemistry - A European Journal, 2015, vol. 21, # 28, p. 10179 - 10184
[6] Patent: CN106146413, 2016, A,
[7] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 13, p. 1845 - 1854
  • 13
  • [ 99-04-7 ]
  • [ 1711-06-4 ]
YieldReaction ConditionsOperation in experiment
99.3% at 90℃; for 3 h; In a 1000 ml reaction flask equipped with a thermometer, a stirrer, a condenser, and an exhaust gas absorption device, 540.56 g of m-toluic acid, 573.0 g of thionyl chloride and 1.0 g of N, N-dimethylformamide were charged and heated to 90 ° C, the reaction was stirred 3h, the reaction was completely transparent, excess pressure to remove excess thionyl chloride, m-methyl benzoyl chloride 610.0g, purity 98.2percent, yield 99.3percent o
98.2% With thionyl chloride; tetra(n-butyl)ammonium hydrogensulfate In 5,5-dimethyl-1,3-cyclohexadiene at 45℃; for 4.5 h; Large scale m-methyl benzoyl chloride continuous production process is as follows: (1) m-methylbenzoic acid 1360kg, 1453kg thionylchloride and 2720kg xylene were added to the reactor. Then, addition of 2.04kg tetrabutyl ammonium hydrogen sulfate. At 45 deg.C reaction 4h, until no gas evolution. Continue to hold temperature for 0.5 hours, to obtain a reaction solution;(2) The reaction mixture was added tothe distillation column, flow into the tower 4.7kg / min, distillation tower bottoms heated by steam, Temperature controlled at 105 , overhead light component recovery flow 4.2kg / min, light component after condensed by the condenser returned to the reaction vessel; (3) the distillation tower reactor m-methylbenzoyl chloride crude product was added to the thin film evaporator, feed rate of 3.9kg / min, adjust the degree of vacuum to 630mmHg, vacuum distillation at 127 deg.C, to give 1516.5 kg-methyl chloride in a yield of 98.2percent, after testing, chromatography between methyl chloride content of 99.4percent.
98.9% With thionyl chloride In N,N-dimethyl-formamide at 90℃; for 4 h; (1) Add 330 g of m-toluic acid to the reaction vessel, add 360 g of thionyl chloride and 5 g of DMF, and stir for 2 h. When there is no obvious gas in the reaction vessel, the temperature is raised to 90 ± 5 ° C. Incubated for 2 h to complete the reaction, and then distilled at 120 ° C excess excess thionyl chloride. M-methyl benzoyl chloride yield of 98.9percent;
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[2] Patent: CN105348085, 2016, A, . Location in patent: Paragraph 0026; 0027; 0028; 0029; 0030
[3] Patent: CN107400052, 2017, A, . Location in patent: Paragraph 0016
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[113] Journal of Organic Chemistry, 2016, vol. 81, # 24, p. 12143 - 12168
[114] Organic Letters, 2016, vol. 18, # 21, p. 5668 - 5671
[115] Journal of the American Chemical Society, 2017, vol. 139, # 5, p. 1762 - 1765
[116] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 15 - 25
  • 14
  • [ 79-37-8 ]
  • [ 99-04-7 ]
  • [ 1711-06-4 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 16, p. 6449 - 6457
[2] Chemistry - A European Journal, 2017, vol. 23, # 50, p. 12149 - 12152
  • 15
  • [ 99-04-7 ]
  • [ 98-88-4 ]
  • [ 1711-06-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 6, p. 1129 - 1132[2] Zhurnal Organicheskoi Khimii, 1981, vol. 17, # 6, p. 1275 - 1279
  • 16
  • [ 99-04-7 ]
  • [ 2941-78-8 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
[2] Chemische Berichte, 1905, vol. 38, p. 3555
[3] Chemische Berichte, 1905, vol. 38, p. 3555
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2940 - 2948
  • 17
  • [ 99-04-7 ]
  • [ 52548-14-8 ]
YieldReaction ConditionsOperation in experiment
40% With sulfuric acid; iodine; periodic acid In water; acetic acid at 20 - 118℃; for 6 h; Heating / reflux The same procedure as in Example 1 was carried out, except that 3-methylbenzoic acid (20 g, 0.15 mol) was used as the reactant in Example 1. A conversion of 3-methylbenzoic acid was 50 percent; the yields were 1) 40 percent for 6-iodo-3-methylbenzoic acid and 2) 8 percent for the regioisomers of other iodides; and a ratio of 1)/2) was 5.
33% With sulfuric acid; iodine; periodic acid In water; acetic acid at 20 - 118℃; for 6 h; Heating / reflux The same procedure as in Example 2 was carried out, except that H-β zeolite was not used in Example 2. A conversion of 3-methylbenzoic acid was 56 percent; the yields were 1) 33 percent for 6-iodo-3-methylbenzoic acid and 2) 16 percent for the regioisomers of other iodides; and a ratio of 1)/2) was 2.1.
Reference: [1] ACS Catalysis, 2018, vol. 8, # 2, p. 920 - 925
[2] Patent: EP1595862, 2005, A1, . Location in patent: Page/Page column 8
[3] Patent: EP1595862, 2005, A1, . Location in patent: Page/Page column 8
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974, p. 2405 - 2409
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2940 - 2948
[6] Patent: US2015/31673, 2015, A1, . Location in patent: Paragraph 0419
  • 18
  • [ 99-04-7 ]
  • [ 1048025-55-3 ]
  • [ 52548-14-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 28, p. 5215 - 5219
[2] ACS Catalysis, 2018, vol. 8, # 2, p. 920 - 925
  • 19
  • [ 99-04-7 ]
  • [ 3113-72-2 ]
  • [ 3113-71-1 ]
  • [ 5437-38-7 ]
Reference: [1] Journal of the Chinese Chemical Society, 2014, vol. 61, # 12, p. 1307 - 1312
[2] Tetrahedron Letters, 2006, vol. 47, # 49, p. 8651 - 8652
[3] Tetrahedron Letters, 2008, vol. 49, # 28, p. 4449 - 4451
[4] Tetrahedron Letters, 2011, vol. 52, # 13, p. 1452 - 1455
  • 20
  • [ 99-04-7 ]
  • [ 3113-72-2 ]
  • [ 5437-38-7 ]
Reference: [1] Journal of the Chinese Chemical Society, 2014, vol. 61, # 12, p. 1307 - 1312
[2] Chemische Berichte, 1905, vol. 38, p. 3555
[3] Chemische Berichte, 1909, vol. 42, p. 433
[4] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 169
[5] Gazzetta Chimica Italiana, 1935, vol. 65, p. 840,842
  • 21
  • [ 99-04-7 ]
  • [ 3113-72-2 ]
  • [ 3113-71-1 ]
  • [ 5437-38-7 ]
  • [ 3478-09-9 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 28, p. 4449 - 4451
  • 22
  • [ 99-04-7 ]
  • [ 3113-72-2 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
[2] Chemische Berichte, 1909, vol. 42, p. 433
[3] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 169
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2940 - 2948
  • 23
  • [ 99-04-7 ]
  • [ 3113-72-2 ]
  • [ 3113-71-1 ]
Reference: [1] Chemische Berichte, 1907, vol. 40, p. 4413
[2] Chemische Berichte, 1905, vol. 38, p. 3555
[3] Chemische Berichte, 1909, vol. 42, p. 433
  • 24
  • [ 7697-37-2 ]
  • [ 99-04-7 ]
  • [ 3113-72-2 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 3555
[2] Chemische Berichte, 1881, vol. 14, p. 2356
[3] Chemische Berichte, 1909, vol. 42, p. 433
  • 25
  • [ 99-04-7 ]
  • [ 5437-38-7 ]
YieldReaction ConditionsOperation in experiment
50% at -10℃; for 1 h; Inert atmosphere 2-Toluic acid (1g, 7.35mmol) was added slowly with stirring to fuming nitric acid (4mL) in −10°C, then the mixture was stirred at this temperature for 1h. TLC analysis of the reaction (n-hexane/EtOH) confirmed the formation of a new compound. After the reaction was judged to be completed, the mixture was filtered and precipitated solid was washed with cold water. Compound 4 (0.66g, 50percent) was obtained after drying, mp 217–219°C (lit. 217–219°C);5a δH (300MHz, acetone-d6) 2.33 (3H, s, Me), 7.60 (1H, t, J 7.7Hz, Ph), 7.70 (1H, d, J 7.6Hz, Ph), 7.94 (1H, d, J 7.6Hz, Ph), 10.15 (1H, br s, CO2H); δC (75MHz, DMSO-d6) 16.7, 124.1, 129.0, 130.3, 131.0, 136.1, 150.5, 165.1.
Reference: [1] Tetrahedron, 2013, vol. 69, # 32, p. 6679 - 6686
[2] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 10, p. 3659 - 3662
[3] Journal of Organic Chemistry, 2003, vol. 68, # 23, p. 8918 - 8931
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1637 - 1648
[5] Chemische Berichte, 1881, vol. 14, p. 2356
[6] Zeitschrift fuer Chemie, 1869, p. 105
[7] American Chemical Journal, 1910, vol. 44, p. 122,508[8] American Chemical Journal, 1911, vol. 45, p. 445
[9] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2940 - 2948
[10] Helvetica Chimica Acta, 1976, vol. 59, p. 379 - 387
[11] Patent: CN106496038, 2017, A,
[12] Patent: CN106496038, 2017, A,
[13] Patent: CN108129322, 2018, A, . Location in patent: Paragraph 0043; 0045; 0047; 0049; 0051; 0053; 0058-0059
  • 26
  • [ 99-04-7 ]
  • [ 3113-72-2 ]
  • [ 3113-71-1 ]
  • [ 5437-38-7 ]
Reference: [1] Journal of the Chinese Chemical Society, 2014, vol. 61, # 12, p. 1307 - 1312
[2] Tetrahedron Letters, 2006, vol. 47, # 49, p. 8651 - 8652
[3] Tetrahedron Letters, 2008, vol. 49, # 28, p. 4449 - 4451
[4] Tetrahedron Letters, 2011, vol. 52, # 13, p. 1452 - 1455
  • 27
  • [ 99-04-7 ]
  • [ 3113-72-2 ]
  • [ 5437-38-7 ]
Reference: [1] Journal of the Chinese Chemical Society, 2014, vol. 61, # 12, p. 1307 - 1312
[2] Chemische Berichte, 1905, vol. 38, p. 3555
[3] Chemische Berichte, 1909, vol. 42, p. 433
[4] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 169
[5] Gazzetta Chimica Italiana, 1935, vol. 65, p. 840,842
  • 28
  • [ 99-04-7 ]
  • [ 3113-72-2 ]
  • [ 3113-71-1 ]
  • [ 5437-38-7 ]
  • [ 3478-09-9 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 28, p. 4449 - 4451
  • 29
  • [ 99-04-7 ]
  • [ 3113-71-1 ]
  • [ 5437-38-7 ]
Reference: [1] Chemische Berichte, 1907, vol. 40, p. 4413
[2] Chemische Berichte, 1909, vol. 42, p. 433
  • 30
  • [ 7697-37-2 ]
  • [ 99-04-7 ]
  • [ 5437-38-7 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 2356
[2] Zeitschrift fuer Chemie, 1869, p. 105
  • 31
  • [ 99-04-7 ]
  • [ 13293-59-9 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 21, p. 4105 - 4111
[2] Journal of Organic Chemistry, 1980, vol. 45, # 16, p. 3236 - 3245
[3] Patent: US5086062, 1992, A,
[4] Molecular Catalysis, 2018, vol. 444, p. 53 - 61
  • 32
  • [ 617-84-5 ]
  • [ 99-04-7 ]
  • [ 134-62-3 ]
YieldReaction ConditionsOperation in experiment
91% With hydrogenchloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In 1,4-dioxane at 120℃; for 22 h; General procedure: A 20 mL Radleys Carousel screw-capped glass tube was charged with carboxylic acid (2 mmol, 1.0 equiv), DMF (1.2 mL), T3P® in DMF 50percent(1.28 mL, 1.4 g, 1.1 equiv) and HCl (4 M in dioxane, 0.25 mL, 1.0mmol, 0.5 equiv) at r.t. The mixture was heated to 130 °C (ca. 120 °C internal) and stirred until the conversion according to LC-MS or TLCwas ≥95percent. The solution was quenched at 10 °C with aq half-saturated Na2CO3 (5 mL; caution: gas evolution) and extracted with i-PrOAc (10mL and 2 × 5 mL or until no product was present in the aqueousphase). Combined organic phases were dried over MgSO4 and concentratedunder reduced pressure. The crude product was purified bychromatography on silica gel as described below. N,N-Diethyl-3-methylbenzamide (20) The reaction was performed according to the general procedure withN,N-diethylformamide using m-toluic acid as starting material. Afterwork-up, the crude material was absorbed on Celite, concentrated todryness and purified by chromatography on silica gel (50 g IsoluteSPE column, Flash Si II; heptane–EtOAc, 4:1 to 1:2) to give 20.Yield: 347 mg (91percent); yellow oil.1H NMR (500 MHz, CDCl3): δ = 7.26–7.29 (m, 1 H), 7.19 (m, 2 H), 7.14–7.16 (m, 1 H), 3.54 (br s, 2 H), 3.26 (br s, 2 H), 2.37 (s, 3 H), 1.25 (br s,3 H), 1.11 (br s, 3 H).13C NMR (125 MHz, CDCl3): δ = 171.48, 138.23, 137.29, 129.78,128.23, 126.94, 123.16, 43.28, 39.16, 21.42, 14.26, 12.96.
Reference: [1] Synthesis (Germany), 2016, vol. 48, # 13, p. 2069 - 2078
  • 33
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  • [ 134-62-3 ]
YieldReaction ConditionsOperation in experiment
96% at 100 - 280℃; for 6 h; Inert atmosphere; Large scale In a 2-cubic stirred reactor, 486 kg of m-methylbenzoic acid, 1314 kg of diethylamine was added,Steam jacket heated to 100 , open stirring, and keep the stirring speed of 120 r / min, to be methyl benzoic acid in diethylamine completely dissolved, the analysis of raw materials without free m-methyl benzoic acid raw materials.The reactor is filled with Zn-MCM-22 catalyst with an effective volume of about 2 m3, about 1.6 tons of catalyst, and the reactor is chargedAfter full nitrogen, open the circulating compressor, nitrogen circulation of 9m3 / min. The reactor pressure was maintained at 2.0 MPa through the reactor upper pressure regulator, and the reactor catalyst bed temperature was slowly raised to 250 ° C by means of a heat exchanger. Start the feed pump to 250kg / h liquid flow rate of raw materials into the raw material preheater, the material heated to 280 , through the heat exchanger to the reactor gas phase discharge temperature down to 150 into the gas-liquid separator, In the separator, most of the water as the liquid phase in the bottom of the separator, the gas phase for the circulating nitrogen and a small amount of organic amine raw materials, after heating and pressure, re-from the bottom of the reactor into the reactor, countercurrent contact with the reaction product to provide the reaction The required heat, and timely out of the organic ammonium salt from the water out of the reactor to promote the progress of the reaction.The product at the bottom of the reactor enters the product purification column and the impurities are removed by distillation to obtain N, N-diethyl-m-tolueneAmide products. Through 6 hours of continuous industrial reaction, refined after the product 550 kg, according to m-methyl benzoic acid, the product yield 96percent.
Reference: [1] Patent: CN104418760, 2016, B, . Location in patent: Paragraph 0032; 0033; 0034; 0035; 0036
[2] Synthesis, 2003, # 2, p. 272 - 276
[3] Petroleum Chemistry, 1997, vol. 37, # 4, p. 320 - 331
[4] Tetrahedron, 1976, vol. 32, p. 2211 - 2217
[5] Patent: US2011/89019, 2011, A1, . Location in patent: Page/Page column 8
[6] Patent: US2011/89021, 2011, A1, . Location in patent: Page/Page column 9-10
  • 34
  • [ 88-10-8 ]
  • [ 99-04-7 ]
  • [ 134-62-3 ]
YieldReaction ConditionsOperation in experiment
97.5% at 20℃; for 0.333333 h; 136 g ( 1 Mole) of m-toluic acid (3-methyl benzoic acid) and 136 g (= 1 27 ml. 1 Mole) N,N-diethylcarbamoyl chloride are taken in a 1 liter two-necked round-bottom flask lltted with air condenser which is placed over a magnetic stirrer. To this, 121 g ( 167 ml. 1.2 Mole) of triethylamine, which is a organic base is added using a pressure-equalizing funnel fitted in the side neck of the round bottom flask at room temperature. After complete addition, the reaction m ixture is stirred constantly for 20 minutes at room temperature. The reaction mixture is then treated with 250 ml of water and the two layers are separated. Pure and colourless N,N-diethyl m-toluamide (DEET) is obtained by vacuum disti l lation of organic layer wh ich is the product. Purity of the compound is analyzed using GC-MS which is more than 99.5percent. The yield of the product is 186 g (97.5percent).
97.5% at 20℃; for 0.333333 h; Example 2 Preparation of N,N-Diethyl m-Toluamide (DEET) [0095] 136 g (1 Mole) of m-toluic acid (3-methyl benzoic acid) and 136 g (=127 ml, 1 Mole) N,N-diethylcarbamoyl chloride are taken in a 1 liter two-necked round-bottom flask fitted with air condenser which is placed over a magnetic stirrer. To this, 121 g (167 ml. 1.2 Mole) of triethylamine, which is a organic base is added using a pressure-equalizing funnel fitted in the side neck of the round bottom flask at room temperature. After complete addition, the reaction mixture is stirred constantly for 20 minutes at room temperature. The reaction mixture is then treated with 250 ml of water and the two layers are separated. Pure and colourless N,N-Diethyl m-toluamide (DEET) is obtained by vacuum distillation of organic layer which is the product. [0096] Purity of the compound is analyzed using GC-MS which is more than 99.5percent. The yield of the product is 186 g (97.5percent).
Reference: [1] Patent: WO2013/65059, 2013, A1, . Location in patent: Page/Page column 13
[2] Patent: US2015/126734, 2015, A1, . Location in patent: Paragraph 0095-0096
  • 35
  • [ 660-68-4 ]
  • [ 99-04-7 ]
  • [ 134-62-3 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 40, p. 6879 - 6882
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2007, vol. 182, # 3, p. 657 - 666
  • 36
  • [ 99-04-7 ]
  • [ 22223-49-0 ]
Reference: [1] Chemische Berichte, 1907, vol. 40, p. 4413
[2] Tetrahedron, 2013, vol. 69, # 32, p. 6679 - 6686
  • 37
  • [ 99-04-7 ]
  • [ 601-87-6 ]
Reference: [1] Helvetica Chimica Acta, 1976, vol. 59, p. 379 - 387
  • 38
  • [ 99-04-7 ]
  • [ 7697-28-1 ]
  • [ 6967-82-4 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 2356
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  • [ 99-04-7 ]
  • [ 7697-28-1 ]
  • [ 6967-82-4 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 2356
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Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 23, p. 8918 - 8931
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Reference: [1] Chemische Berichte, 1907, vol. 40, p. 4413
[2] Tetrahedron, 2013, vol. 69, # 32, p. 6679 - 6686
[3] Patent: CN106496038, 2017, A,
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Reference: [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 28, p. 5215 - 5219
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  • [ 22071-22-3 ]
Reference: [1] Tetrahedron Letters, 1988, vol. 29, # 3, p. 339 - 342
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  • [ 2486-70-6 ]
Reference: [1] Chemische Berichte, 1909, vol. 42, p. 433
[2] Chemische Berichte, 1909, vol. 42, p. 433
[3] Chemische Berichte, 1909, vol. 42, p. 433
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Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 390 - 401
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  • [ 500024-27-1 ]
Reference: [1] Chemische Berichte, 1907, vol. 40, p. 4413
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  • [ 20587-30-8 ]
Reference: [1] Chemische Berichte, 1909, vol. 42, p. 433
[2] Chemische Berichte, 1909, vol. 42, p. 433
[3] Chemische Berichte, 1909, vol. 42, p. 433
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  • [ 24078-21-5 ]
Reference: [1] Patent: CN106496038, 2017, A,
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Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2746 - 2754
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Reference: [1] Angewandte Chemie, International Edition, 2009, vol. 48, # 33, p. 6097 - 6100[2] Angewandte Chemie, 2009, vol. 121, # 33, p. 6213 - 6216
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Reference: [1] Angewandte Chemie, International Edition, 2009, vol. 48, # 33, p. 6097 - 6100[2] Angewandte Chemie, 2009, vol. 121, # 33, p. 6213 - 6216
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Reference: [1] Patent: WO2011/21209, 2011, A1,
[2] Patent: US2012/101099, 2012, A1,
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[2] Patent: US2012/101099, 2012, A1,
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Reference: [1] Patent: WO2011/21209, 2011, A1,
[2] Patent: US2012/101099, 2012, A1,
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