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Chemical Structure| 95-74-9
Chemical Structure| 95-74-9
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Product Details of [ 95-74-9 ]

CAS No. :95-74-9 MDL No. :MFCD00007773
Formula : C7H8ClN Boiling Point : -
Linear Structure Formula :- InChI Key :RQKFYFNZSHWXAW-UHFFFAOYSA-N
M.W : 141.60 Pubchem ID :7255
Synonyms :

Calculated chemistry of [ 95-74-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.82
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 2.93
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 2.41
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 2.3

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.124 mg/ml ; 0.000877 mol/l
Class : Soluble
Log S (Ali) : -3.14
Solubility : 0.103 mg/ml ; 0.000728 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.137 mg/ml ; 0.000966 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 95-74-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P273-P280-P301+P310-P305+P351+P338-P312 UN#:2239
Hazard Statements:H301+H311-H315-H317-H319-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 95-74-9 ]

* 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 [ 95-74-9 ]
  • Downstream synthetic route of [ 95-74-9 ]

[ 95-74-9 ] Synthesis Path-Upstream   1~31

  • 1
  • [ 121-86-8 ]
  • [ 95-74-9 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With hydrogenchloride; 1,1,1,3',3',3'-hexafluoro-propanol; iron In water at 20℃; for 0.5 h;
Stage #2: With sodium hydrogencarbonate In water
General procedure: The nitro compound (1 equiv), HFIP (10 equiv), Fe powder (5 equiv) were mixed in a tube. Then 2 N HCl aqueous solutions was added to the reaction mixture. After stirring at room temperature for 30 min, the reaction mixture was neutralized with sat. NaHCO3 (aq.) and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was then purified by column chromatography on silica gel to furnish the desired amine product.
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 47, p. 17089 - 17097
[2] Tetrahedron Letters, 2017, vol. 58, # 37, p. 3646 - 3649
[3] Chemische Berichte, 1884, vol. 17, p. 534
[4] Recueil des Travaux Chimiques des Pays-Bas, 1932, vol. 51, p. 98,109
[5] Chem. Zentralbl., 1910, vol. 81, # I, p. 260
[6] Recueil des Travaux Chimiques des Pays-Bas, 1913, vol. 32, p. 247
[7] Journal of the American Chemical Society, 1959, vol. 81, p. 5641,5644
[8] Journal of the American Chemical Society, 1959, vol. 81, p. 5641,5644
[9] Journal of the Chemical Society, 1927, p. 2903
[10] Journal of the American Chemical Society, 1944, vol. 66, p. 1781
[11] Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 776 - 794
[12] Journal of Organic Chemistry, 1998, vol. 63, # 2, p. 393 - 395
[13] Patent: CN104163764, 2016, B, . Location in patent: Paragraph 0044-0047
  • 2
  • [ 89794-02-5 ]
  • [ 95-74-9 ]
Reference: [1] Nature Chemistry, 2017, vol. 9, # 7, p. 681 - 688
  • 3
  • [ 7006-52-2 ]
  • [ 95-74-9 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 4, p. 713 - 715
  • 4
  • [ 99-99-0 ]
  • [ 95-74-9 ]
Reference: [1] Chemische Berichte, 1884, vol. 17, p. 534
[2] Journal of the Chemical Society, 1927, p. 2903
[3] Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 776 - 794
  • 5
  • [ 42533-63-1 ]
  • [ 95-74-9 ]
Reference: [1] Chemische Berichte, 1892, vol. 25, p. 83
  • 6
  • [ 95-49-8 ]
  • [ 95-74-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1913, vol. 32, p. 247
  • 7
  • [ 88-51-7 ]
  • [ 95-74-9 ]
Reference: [1] Journal of Chemical Crystallography, 2013, vol. 43, # 12, p. 655 - 663
  • 8
  • [ 121-86-8 ]
  • [ 42460-61-7 ]
  • [ 95-74-9 ]
Reference: [1] Chem. Zentralbl., 1910, vol. 81, # I, p. 260
  • 9
  • [ 15545-48-9 ]
  • [ 124-40-3 ]
  • [ 95-74-9 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2001, # 11, p. 2230 - 2232
  • 10
  • [ 15545-48-9 ]
  • [ 95-74-9 ]
Reference: [1] Chemosphere, 2002, vol. 46, # 4, p. 519 - 526
  • 11
  • [ 15545-48-9 ]
  • [ 7260-94-8 ]
  • [ 95-74-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2, 2001, # 11, p. 2226 - 2229
  • 12
  • [ 7664-93-9 ]
  • [ 106-49-0 ]
  • [ 95-74-9 ]
  • [ 615-65-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1873, vol. 168, p. 199
[2] Chemische Berichte, 1889, vol. 22, p. 2535,2536
  • 13
  • [ 7647-01-0 ]
  • [ 7664-93-9 ]
  • [ 106-49-0 ]
  • [ 56461-98-4 ]
  • [ 95-74-9 ]
  • [ 615-65-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1873, vol. 168, p. 199
[2] Chemische Berichte, 1889, vol. 22, p. 2535,2536
  • 14
  • [ 7647-01-0 ]
  • [ 110-89-4 ]
  • [ 7149-79-3 ]
  • [ 64-19-7 ]
  • [ 95-74-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1886, vol. 235, p. 242
  • 15
  • [ 95-74-9 ]
  • [ 452-73-3 ]
YieldReaction ConditionsOperation in experiment
81.8%
Stage #1: at 5 - 15℃; for 5 h;
Stage #2: at -5 - 80℃;
1L reactor (equipped with a condenser, the gas phase outlet diameter is1/6 to 1/5 of thediameter of the kettle), and the temperature is lowered to 20 °C or lower. Under stirring, 424 g (21.2 mol, 20 eq) of anhydrous hydrogen fluoride is added, and the temperature is lowered after the feed is completed. To 5 °C or less,150 g (1.059 mol, 1 eq) of 3-chloro-4-methylaniline wasadded dropwise, and the temperature was controlled in the range of 5 to 15 °C, and the addition was completed in about 3 hours, and the temperature was kept for 2 hours.After thecompletion of theheat preservation, thetemperature was lowered to 5 °C or less, and 73.1 g of sodium nitrite (1.06 mol, 1 eq) was added in portions, and the reaction temperature was controlled within the rangeof-5 to 15 °C, and the mixture was added forabout 4 hours, and the heat was kept for 1 hour.After the heat preservation, the temperature of the reaction kettle is programmed (strictly controlling the heating rate:when thetemperature is in the range of 0 to 20 °C, the temperature is raised by 0.5 to 1 °C per hour,when the temperature is in the range of 20 to 80 °C, the temperature is raised by 1 to 2 °C per hour), and the temperature is raised to 80 °C and keep warm for2h.After the heat preservation is completed, the temperature is lowered to 30 to 35 °C, and the layers are separated. The organic layer is neutralized to a pH of 7 to 8 by a dilute alkali, and steam distillation is carried out. The organic layer is 141 g at room temperature, and the purity of the gas chromatographic detection is 93.4percent. The distillation obtained 125.1 g of qualified product, the yield was 81.8percent, and the purity of 2-chloro-4-fluorotoluene obtained by gas chromatography was 99.9percent.
Reference: [1] Patent: CN108569948, 2018, A, . Location in patent: Paragraph 0035-0059
  • 16
  • [ 95-74-9 ]
  • [ 5162-82-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 39, p. 496[2] Justus Liebigs Annalen der Chemie, 1891, vol. 265, p. 349
  • 17
  • [ 95-74-9 ]
  • [ 21423-81-4 ]
Reference: [1] Patent: US4562199, 1985, A,
  • 18
  • [ 143-33-9 ]
  • [ 95-74-9 ]
  • [ 21423-81-4 ]
Reference: [1] Journal of the Chemical Society, 1947, p. 637,640
[2] Zhurnal Obshchei Khimii, 1936, vol. 6, p. 909,912[3] Chem. Zentralbl., 1937, vol. 108, # I, p. 1942
  • 19
  • [ 95-74-9 ]
  • [ 21423-81-4 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 39, p. 496[2] Justus Liebigs Annalen der Chemie, 1891, vol. 265, p. 349
  • 20
  • [ 95-74-9 ]
  • [ 615-62-3 ]
Reference: [1] Patent: DE156333, , ,
[2] Justus Liebigs Annalen der Chemie, 1907, vol. 355, p. 366[3] Justus Liebigs Annalen der Chemie, 1909, vol. 371, p. 388
[4] Patent: US4577011, 1986, A,
[5] Patent: US4558040, 1985, A,
[6] Patent: DE156333, , ,
  • 21
  • [ 7647-01-0 ]
  • [ 7664-93-9 ]
  • [ 106-49-0 ]
  • [ 56461-98-4 ]
  • [ 95-74-9 ]
  • [ 615-65-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1873, vol. 168, p. 199
[2] Chemische Berichte, 1889, vol. 22, p. 2535,2536
  • 22
  • [ 95-74-9 ]
  • [ 21971-21-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1907, vol. 355, p. 366[2] Justus Liebigs Annalen der Chemie, 1909, vol. 371, p. 388
  • 23
  • [ 95-74-9 ]
  • [ 88-51-7 ]
YieldReaction ConditionsOperation in experiment
99.1% With sulfuric acid In 1,2-dichloro-benzene at 240℃; for 8 h; Autoclave To 141.6 g (1.00 ) of 2-chloro-4-amino-toluene with 1,2-dichlorobenzene in 2,000 [0163] Dosage for 4 In the L stainless steel reactor Flask, 101.0 g of sulfuric acid (1.03 ) for 30 minutes. [0165] the reactor and raising the temperature of the external temperature and the reaction was performed at reflux for 240 8 hours. The reaction can be generated during the reflux reaction Dean-separated and the organic components were using Stark trap. [0167] into a discrete compound of the stainless steel of 4 L dryer, maintaining the temperature more than 200 Hg vacuum at 150 While, and dried for 8 hours, to give a final 2-chloro-4-amino toluene-5-sulfonic acid in 219.7 g. 2-chloro-4-amino-2-chloro-4-amino toluene-5-sulfonic acid in toluene yields according to the standard of was 99.1percent.
99.2% With sulfuric acid In 1,2-dichloro-benzene at 240℃; for 8.5 h; Dean-Stark 141.6 g (1.00 mol) of 2-chloro-4-aminotoluene and 2,000 ml of 1,2-dichlorobenzene were placed in a glass material reactor having a capacity of 4 L,After stirring, 100.1 g (1.00 mol) of sulfuric acid was added over 30 minutes.Then, the temperature outside the reactor was raised, and the reflux reaction was carried out at 240 DEG C for 8 hours. The reaction water generated at this time was separated from organic components using a Dean-Stark trap.The reaction was filtered through a 2 L fluid filter and the filtrate was washed with 100 mL of 1,2-dichlorobenzene. The washed filtrate is collected in a 4 L glass reactor for reuse after distillation in a subsequent reaction, and 2-chloro-4-aminotoluene-5-sulfonic acid in a wet cake state is put into a 4 L stainless steel material drier or a glass vacuum drier, And dried at 130 to 160 DEG C for 7 hours while maintaining a vacuum of 200 mmHg or more to obtain 219.7 g of 2-chloro-4-aminotoluene-5-sulfonic acid. The yield of 2-chloro-4-aminotoluene-5-sulfonic acid according to the criteria of 2-chloro-4-aminotoluene was 99.2percent. As a result of HPLC analysis, the content of residual 2-chloro-4-aminotoluene was 0.10percent by weight, no other organic impurities were detected, and the purity according to the diazotization titration was 97.8percent. The appearance of the resulting 2-chloro-4-aminotoluene-5-sulfonic acid was in the form of a white powder, and an aqueous ammonia solution having a concentration of 2-chloro-4-aminotoluene-5-sulfonic acid of 1.3percent was prepared and analyzed by ultraviolet spectroscopy The absorbance was measured at a wavelength of 400 nm and the result was 0.041. To confirm the residue (insoluble matter and tar) when the product was dissolved, 2-chloro-4-aminotoluene prepared in an aqueous alkali solution (pH 9, aqueous ammonia solution) -5-sulfonic acid was dissolved and filtered. As a result,The weight percentage of insoluble matter was found to be 0.051 (insoluble,percent).
Reference: [1] Patent: KR2015/104064, 2015, A, . Location in patent: Paragraph 0161-0165
[2] Patent: KR2016/92961, 2016, A, . Location in patent: Paragraph 0151-0159
[3] Patent: DE175378, , ,
[4] Patent: DE175378, , ,
  • 24
  • [ 110-01-0 ]
  • [ 7664-93-9 ]
  • [ 95-74-9 ]
  • [ 88-51-7 ]
Reference: [1] Patent: US4447368, 1984, A,
  • 25
  • [ 95-74-9 ]
  • [ 2835-95-2 ]
YieldReaction ConditionsOperation in experiment
85.36% With copper; copper(l) chloride; sodium hydroxide In ethanol at 175℃; for 4 h; Autoclave; Inert atmosphere; Industrial scale In a 4800L autoclave, 1700 kg of 50percent sodium hydroxide solution was added, 1850 kg of an ethanol solution containing 1000 kg of 3-chloro-4-methylaniline was added, 50 kg of cuprous chloride and 15 kg of copper powder were added, and the reaction vessel was sealed and replaced with nitrogen 5 times. Warm up to 175°C, incubate for 4 hours, sample and analyze. After passing the test, cool down. Ethanol is recovered under reduced pressure, filtered into an 8000L tank, neutralized by adding 1450 kg of industrial hydrochloric acid to weak acidity, extracted with 2000 L of ethyl acetate and extracted three times, and ethyl acetate is recovered under reduced pressure. , get crude. The crude product was added with 1000 kg of ethanol, heated to 60° C., and 50 kg of activated carbon was added. After stirring for 1 hour, the mixture was filtered and cooled to 5° C. to obtain 707 kg of a product with a yield of 85.36percent and a purity of 99.8percent.
Reference: [1] Patent: CN107963974, 2018, A, . Location in patent: Paragraph 0030-0032; 0036; 0037
  • 26
  • [ 95-74-9 ]
  • [ 7149-80-6 ]
Reference: [1] Patent: WO2010/19208, 2010, A1,
  • 27
  • [ 95-74-9 ]
  • [ 54788-38-4 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1907, vol. 355, p. 366[2] Justus Liebigs Annalen der Chemie, 1909, vol. 371, p. 388
  • 28
  • [ 95-74-9 ]
  • [ 102170-52-5 ]
YieldReaction ConditionsOperation in experiment
64% With N-Bromosuccinimide In dichloromethane at 20℃; for 0.166667 h; Example 41: (5-Chloro-2-((E)-3-13-(4-fl uorobenzvl)-3,8-diazabicvdo13 .2. I loct-8-vll-3- oxopropenyl} -4-methylphenyl)-urea; a) 2-Bromo-5-chloro-4-methylphenylamine; 3-Chloro-4-methylphenylamine (20.0 g; 0.141 mmol) is dissolved in CH2CI2 (200 ml) and combined within 5 min. with a solution of NBS (25.1 g; 0.141 mmol) in CH2CI2 (800 ml). The reaction mixture is stirred for 5 min at room temp. , evaporated to a volume of -200 ml and diluted with hexanes (1000 ml). The resulting precipitate is filtered off, the filtrate evaporated to dryness and purified via chromatography (Si02, hexanes / TBME 10: 1) to render the title compound as yellowish crystals (12.3 g; 40 percent). A second batch of title compound is obtained by re-chromatography of mixed fractions (7.5 g; 24 percent). 1H-NMR (400MHz; DMSO-d6), No. (ppm) : 2.13 (s, 3H) ; 5.32 (s, 2H, NH2) ; 6.81 (s, 1 H); 7.31 (s, 1 H). MS (m/z) ES+: 221 (100, M+) ; 219 (80) ; 184 (35 ); 140 (100) ; 104 (50) ; 77 (65) ; 52 (58) ; 51 (60).
Reference: [1] Patent: WO2005/103054, 2005, A2, . Location in patent: Page/Page column 71
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 17, p. 3692 - 3702
  • 29
  • [ 95-74-9 ]
  • [ 102170-52-5 ]
YieldReaction ConditionsOperation in experiment
34% With bromine In diethyl ether; acetic acid at 0 - 5℃; for 0.75 h; Under argon [00148] To a solution of 3-chloro-4-methylaniline (10.0 g, 70.6 mmol) in diethyl ether/acetic acid (v/v 1/1, 350 ml) cooled in an ice-bath was dropwise added bromine (4 ml) over a 35 min period under an argon atmosphere while the temperature of the reaction mixture was kept below 5 C. Stirring was continued for 10 min after the addition of bromine; then the yellow reaction mixture was partitioned between dichloromethane (250 ml) and dilute brine (200 ml). The organic layer was washed with more dilute brine (200 ml), dried (Na2SO4), and concentrated in vacuo to an oily residue. This was redissolved in dichloromethane (200 ml) and the solution was washed with saturated aqueous sodium bicarbonate (3200 ml; caution: gas is evolved), dried (Na2SO4) and concentrated in vacuo to leave a brown wet solid. Purification by column chromatography on gradient elution with dichloromethane in hexanes (25 to 30percent) gave in order of elution: [00149] a. 5-chloro-2,6-dibromo-4-methylaniline as a white solid (4.63 g) mp 77-78 C. [00150] b. the desired product, 2-bromo-5-chloro-4-methylaniline (5.32 g, 34percent), mp 90 C., 1H-NMR (CDCl3) 2.23 (s, 3H, 4-CH3), 3.99 (br s, 2H, NH2), 6.78 (s, 1H, 6-H), 7.26 (s, 1H, 3-H). MS (FAB, m/z) 219, 221, 223 [(M+H)+, BrCl isotopic pattern]. Elemental Analysis: Found: C, 38.04; H, 3.20; N, 6.35; Cl, 16.04; Br, 36.28. C7H7BrClN requires: C, 38.13; H, 3.20; N, 6.35; Cl, 16.08; Br, 36.24 [00151] c. 2-bromo-3-chloro-4-methylaniline as a white solid (1.22 g) mp 48-56 C.
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 17, p. 3692 - 3702
[2] Patent: US6699861, 2004, B1, . Location in patent: Page column 13-14
  • 30
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  • [ 117738-77-9 ]
Reference: [1] Zhurnal Obshchei Khimii, 1936, vol. 6, p. 909,912[2] Chem. Zentralbl., 1937, vol. 108, # I, p. 1942
[3] Zhurnal Obshchei Khimii, 1936, vol. 6, p. 909,912[4] Chem. Zentralbl., 1937, vol. 108, # I, p. 1942
[5] Zhurnal Obshchei Khimii, 1936, vol. 6, p. 909,912[6] Chem. Zentralbl., 1937, vol. 108, # I, p. 1942
  • 31
  • [ 95-74-9 ]
  • [ 162100-42-7 ]
Reference: [1] Patent: CN106278987, 2017, A,
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