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[ CAS No. 623-26-7 ] {[proInfo.proName]}

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Chemical Structure| 623-26-7
Chemical Structure| 623-26-7
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Product Details of [ 623-26-7 ]

CAS No. :623-26-7 MDL No. :MFCD00001810
Formula : C8H4N2 Boiling Point : -
Linear Structure Formula :- InChI Key :BHXFKXOIODIUJO-UHFFFAOYSA-N
M.W : 128.13 Pubchem ID :12172
Synonyms :

Calculated chemistry of [ 623-26-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.87
TPSA : 47.58 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 : Yes
Log Kp (skin permeation) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 0.93
Log Po/w (WLOGP) : 1.43
Log Po/w (MLOGP) : 0.77
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 1.27

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.66
Solubility : 2.78 mg/ml ; 0.0217 mol/l
Class : Very soluble
Log S (Ali) : -1.52
Solubility : 3.91 mg/ml ; 0.0305 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.53
Solubility : 0.378 mg/ml ; 0.00295 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.16

Safety of [ 623-26-7 ]

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 [ 623-26-7 ]

* 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 [ 623-26-7 ]
  • Downstream synthetic route of [ 623-26-7 ]

[ 623-26-7 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 623-26-7 ]
  • [ 7153-22-2 ]
YieldReaction ConditionsOperation in experiment
33% With sulfuric acid In ethanol; water Example 37
Terephthalonitrile (12.8 g), 95percent sulfuric acid (10.3 g), and ethanol (72.5 g) were placed in a glass autoclave, and the mixture was allowed to react at 130° C. for six hours.
The reaction mixture was cooled, and water (9 g) was added thereto.
Gas chromatographic analysis revealed that ethyl p-cyanobenzoate had been produced at a yield of 33percent and a selectivity of 83percent.
30% With hydrogenchloride In ethanol; water Example 38
Terephthalonitrile (12.8 g), hydrogen chloride gas (2.24 NL), and ethanol (72.5 g) were placed in a glass autoclave, and the mixture was allowed to react at 130° C. for six hours.
The reaction mixture was cooled, and water (9 g) was added thereto.
Gas chromatographic analysis revealed that ethyl p-cyanobenzoate had been produced at a yield of 30percent and a selectivity of 96percent.
Reference: [1] Patent: US6433211, 2002, B1,
[2] Patent: US6433211, 2002, B1,
  • 2
  • [ 107-14-2 ]
  • [ 623-26-7 ]
  • [ 1591-30-6 ]
  • [ 876-31-3 ]
YieldReaction ConditionsOperation in experiment
11 %Spectr. at -33℃; for 1.5 h; General procedure: To the stirred suspension of dinitrile 1 (0.300 g,2.34 mmol) in liquid NH3 (30-40 mL) in the atmosphere of evaporating NH3, at temperature –(33-50)°C sodium metal (2.15-2.20 eq) was added by portions. The obtained black-brown suspension of the disodium salt of dianion [1]2– was stirred foradditional 5 min. Then ω-X-alkyl bromide 5a-d (1.3 eq in respectto dinitrile 1) was added dropwise and the stirring was continued for1-1.5 h at –33°C in the atmosphere of evaporating NH3. Then thereaction mixture was allowed to contact with air, Et2O (20-30mL) was added and the stirring was continued until complete evaporation of NH3. Water (30 ml) was added to the residue and the organic products were extracted with Et2O (3×25 mL). The combined ether extract was washed till neutral with water, then with saturated solution of NaCl, dried over MgSO4, and the solvent was evaporated. The compositions of mixtures and yields of products were determined according to 1 NMR (dimethyl terephthalate asstandard) and GLC/MS. Individual compounds were separated by preparative thin layer chromatography (L) using fixed layer of absorbent (silica gel 60 PF254 with addition of gypsum, Merck), the eluent was hexane-Et2O. The result of separation was controlled visually by exposure of dried plate to UV light. The fractions of products were washed from the adsorbent by Et2O.
Reference: [1] Russian Chemical Bulletin, 2016, vol. 65, # 10, p. 2430 - 2436[2] Izv. Akad. Nauk, Ser. Khim., 2016, vol. 10, p. 2430 - 2436,6
  • 3
  • [ 623-26-7 ]
  • [ 35963-33-8 ]
  • [ 83-41-0 ]
  • [ 623-26-7 ]
Reference: [1] Journal of the American Chemical Society, 1986, vol. 108, # 18, p. 5453 - 5459
  • 4
  • [ 623-26-7 ]
  • [ 109-65-9 ]
  • [ 100-47-0 ]
  • [ 1591-30-6 ]
  • [ 104-51-8 ]
  • [ 52709-83-8 ]
  • [ 20651-73-4 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 12, p. 2558 - 2565
  • 5
  • [ 623-26-7 ]
  • [ 109-65-9 ]
  • [ 100-47-0 ]
  • [ 1591-30-6 ]
  • [ 52709-83-8 ]
  • [ 20651-73-4 ]
  • [ 134785-03-8 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 12, p. 2558 - 2565
  • 6
  • [ 623-26-7 ]
  • [ 10406-25-4 ]
  • [ 539-48-0 ]
YieldReaction ConditionsOperation in experiment
92.1% With hydrogen In ammonia; 1,3,5-trimethyl-benzene at 50℃; EXAMPLE 5 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5percent by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.8 molpercent, the yield of 4-cyanobenzylamine was 88.8 molpercent and the yield of p-xylynenediamine was 5.8 molpercent. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of the catalyst A. The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 100 molpercent, the yield of 4-cyanobenzylamine was 0.2 molpercent and the yield of p-xylynenediamine was 92.1 molpercent.
87.7% With hydrogen In ammonia; 1,3,5-trimethyl-benzene at 50℃; EXAMPLE 2 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5percent by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.8 molpercent, the yield of 4-cyanobenzylamine was 88.8 molpercent and the yield of p-xylynenediamine was 5.8 molpercent. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of Ni-diatomaceous earth pellets (manufactured by Nikki Chemical Co., Ltd.; Ni supported amount = 46percent by weight). The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 100 molpercent, the yield of 4-cyanobenzylamine was 0.5 molpercent and the yield of p-xylynenediamine was 87.7 molpercent.
Reference: [1] Patent: EP1449825, 2004, A1, . Location in patent: Page 5
[2] Patent: EP1449825, 2004, A1, . Location in patent: Page 5
  • 7
  • [ 623-26-7 ]
  • [ 539-48-0 ]
YieldReaction ConditionsOperation in experiment
98.7% With hydrogen In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24 h; The procedure of Example 1 was repeated except for using terephthalonitrile in place of isophthalonitrile and changing the amount of Catalyst A to 0.6 g, the pretreatment gas to a mixed gas (methanol:nitrogen=4:96 by volume), and the pretreatment conditions to atmospheric pressure, 250° C., a flow rate of 0.18 NL/h, and 3 h. After 24 h of the hydrogenation, the conversion of terephthalonitrile was 100 mol percent, the yield of p-xylylenediamine was 98.7 mol percent, and the yield of high-boiling condensation products was 1.3 mol percent.
92.4% With hydrogen In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24 h; The procedure of Example 12 was repeated except for omitting the pretreatment. After 24 h of the hydrogenation, the conversion of terephthalonitrile was 100 mol percent, the yield of p-xylylenediamine was 92.4 mol percent, and the yield of high-boiling condensation products was 7.6 mol percent.
92% With hydrogen In ethanol at 95℃; for 1 h; (1) 100g of terephthalonitrile and 3g of Raney-Ni and 400mL of ethanol were added into a 1L hydrogenation kettle, H2 was continuously charged, The reaction pressure during the system is always maintained at 7MPa. The reaction temperature 95 for 1h, cooling. When the temperature in the reaction vessel was lowered to room temperature, the solution was vented to give p-xylylenediamine (purity of 99percent or more) by filtration and recrystallization in a yield of 92percent
35.6% With hydrogen In ammonia; 1,3,5-trimethyl-benzene at 50℃; COMPARATIVE EXAMPLE 2 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of the catalyst A, and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.4 molpercent and the yield of p-xylynenediamine was 35.6 molpercent.

Reference: [1] ChemCatChem, 2014, vol. 6, # 2, p. 538 - 546
[2] Russian Journal of Applied Chemistry, 2003, vol. 76, # 8, p. 1304 - 1309
[3] Patent: US2008/39658, 2008, A1, . Location in patent: Page/Page column 5
[4] Patent: US2008/39658, 2008, A1, . Location in patent: Page/Page column 5
[5] Patent: CN105016939, 2017, B, . Location in patent: Paragraph 0144; 0145
[6] ChemSusChem, 2017, vol. 10, # 5, p. 842 - 846
[7] Angewandte Chemie - International Edition, 2016, vol. 55, # 47, p. 14653 - 14657[8] Angew. Chem., 2016, vol. 128, # 47, p. 14873 - 14877,5
[9] Patent: EP1449825, 2004, A1, . Location in patent: Page 6
[10] Vestnik Akad.Kazachsk.S.S.R., 1959, vol. 15, # 6, p. 92[11] Chem.Abstr., 1960, p. 10944
[12] Doklady Akademii Nauk SSSR, 1957, vol. 112, p. 880[13] Doklady Chemistry, 112-117<1957>141,
[14] Doklady Akademii Nauk SSSR, 1957, vol. 112, p. 880[15] Doklady Chemistry, 112-117<1957>141,
[16] Vestnik Akad.Kazachsk.S.S.R., 1959, vol. 15, # 6, p. 92[17] Chem.Abstr., 1960, p. 10944
[18] Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8781 - 8788
[19] Patent: CN105001032, 2018, B, . Location in patent: Paragraph 0146; 0147
[20] Patent: CN105016940, 2018, B, . Location in patent: Paragraph 0143; 0144
  • 8
  • [ 623-26-7 ]
  • [ 10406-25-4 ]
  • [ 539-48-0 ]
YieldReaction ConditionsOperation in experiment
88.8% With hydrogen In ammonia; 1,3,5-trimethyl-benzene at 50℃; EXAMPLE 2 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5percent by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.8 molpercent, the yield of 4-cyanobenzylamine was 88.8 molpercent and the yield of p-xylynenediamine was 5.8 molpercent. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of Ni-diatomaceous earth pellets (manufactured by Nikki Chemical Co., Ltd.; Ni supported amount = 46percent by weight). The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 100 molpercent, the yield of 4-cyanobenzylamine was 0.5 molpercent and the yield of p-xylynenediamine was 87.7 molpercent. EXAMPLE 5 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5percent by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.8 molpercent, the yield of 4-cyanobenzylamine was 88.8 molpercent and the yield of p-xylynenediamine was 5.8 molpercent. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of the catalyst A. The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50°C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 100 molpercent, the yield of 4-cyanobenzylamine was 0.2 molpercent and the yield of p-xylynenediamine was 92.1 molpercent.
Reference: [1] Patent: EP1449825, 2004, A1, . Location in patent: Page 5
[2] Patent: US6392083, 2002, B1, . Location in patent: Page column 5-6
[3] Patent: EP1454895, 2004, A1, . Location in patent: Page 7; 8
  • 9
  • [ 626-17-5 ]
  • [ 623-26-7 ]
  • [ 1477-55-0 ]
  • [ 539-48-0 ]
Reference: [1] Patent: EP1760070, 2007, A1, . Location in patent: Page/Page column 8
  • 10
  • [ 623-26-7 ]
  • [ 67-56-1 ]
  • [ 874-89-5 ]
Reference: [1] Chemistry Letters, 1981, p. 303 - 306
  • 11
  • [ 623-26-7 ]
  • [ 74-88-4 ]
  • [ 55984-93-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1997, vol. 70, # 9, p. 2269 - 2277
[2] Chemistry Letters, 1995, # 12, p. 1119 - 1120
  • 12
  • [ 623-26-7 ]
  • [ 98689-31-7 ]
  • [ 55984-93-5 ]
Reference: [1] Journal of the American Chemical Society, 1985, vol. 107, # 23, p. 6710 - 6711
  • 13
  • [ 623-26-7 ]
  • [ 15996-76-6 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 40, p. 12808 - 12814
  • 14
  • [ 623-26-7 ]
  • [ 117837-77-1 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 6, p. 1245 - 1247
[2] Patent: KR2015/53913, 2015, A, . Location in patent: Paragraph 0449-0451
  • 15
  • [ 623-26-7 ]
  • [ 117837-77-1 ]
Reference: [1] Patent: US6004965, 1999, A,
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