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[ CAS No. 108-80-5 ] {[proInfo.proName]}

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Chemical Structure| 108-80-5
Chemical Structure| 108-80-5
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Product Details of [ 108-80-5 ]

CAS No. :108-80-5 MDL No. :MFCD00082990
Formula : C3H3N3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZFSLODLOARCGLH-UHFFFAOYSA-N
M.W : 129.07 Pubchem ID :7956
Synonyms :
Chemical Name :1,3,5-Triazinane-2,4,6-trione

Calculated chemistry of [ 108-80-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 25.9
TPSA : 99.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.5
Log Po/w (XLOGP3) : -0.09
Log Po/w (WLOGP) : -1.01
Log Po/w (MLOGP) : -1.92
Log Po/w (SILICOS-IT) : -0.56
Consensus Log Po/w : -0.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.08
Solubility : 10.8 mg/ml ; 0.0838 mol/l
Class : Very soluble
Log S (Ali) : -1.54
Solubility : 3.69 mg/ml ; 0.0286 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.48
Solubility : 392.0 mg/ml ; 3.04 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 108-80-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P305+P351+P338-P337+P313 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 108-80-5 ]

* 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 [ 108-80-5 ]
  • Downstream synthetic route of [ 108-80-5 ]

[ 108-80-5 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 63579-00-0 ]
  • [ 7664-41-7 ]
  • [ 100-97-0 ]
  • [ 108-80-5 ]
Reference: [1] Chemische Berichte, 1886, vol. 19, p. 2092
  • 2
  • [ 112341-86-3 ]
  • [ 3176-66-7 ]
  • [ 112341-85-2 ]
  • [ 108-80-5 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 773 - 778
  • 3
  • [ 108-80-5 ]
  • [ 17497-85-7 ]
YieldReaction ConditionsOperation in experiment
100% With bromine; sodium hydroxide In tetrachloromethane; water at 0℃; The cyanuric acid (5g, 38.5 mmol) wasdissolved in a slight molar excess of chilled aqueousNaOH solution (3 M) at room temperature and thesolution was transferred to a beaker. A solution ofBr2(3 mL, 58.4 mmol) in CCl4(6 mL) was addeddropwise to the reaction mixture with vigorousstirring at 0 °C. Immediately, an orange precipitatewas formed. The resulting solid was isolated by afiltration and washed several times with cold distilledwater and then, it was dried in a vacuum desiccatorat room temperature for 18 h. Finally, an orangepale crystalline solid, tribromoisocyanuric acid, wasobtained quantitatively.
Reference: [1] Oriental Journal of Chemistry, 2015, vol. 31, # 3, p. 1565 - 1570
[2] Synlett, 2006, # 10, p. 1515 - 1518
[3] European Journal of Organic Chemistry, 2013, # 35, p. 8004 - 8013
[4] Arkivoc, 2016, vol. 2016, # 4, p. 193 - 203
[5] Tetrahedron Letters, 2011, vol. 52, # 18, p. 2288 - 2291
[6] South African Journal of Chemistry, 2007, vol. 60, p. 109 - 112
[7] Tetrahedron Letters, 2015, vol. 56, # 49, p. 6843 - 6845
[8] Journal of the Brazilian Chemical Society, 2016, vol. 27, # 6, p. 1129 - 1136
[9] Arkivoc, 2017, vol. 2018, # 2, p. 205 - 214
  • 4
  • [ 108-80-5 ]
  • [ 17497-85-7 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1958, vol. 31, p. 347,350
  • 5
  • [ 108-80-5 ]
  • [ 87-90-1 ]
YieldReaction ConditionsOperation in experiment
98% With hypochlorous anhydride In water at 25℃; for 6 h; Large scale (1) At 25 °C, 2 kg isocyanuric acid was added into 40 L water, stir and obtain isocyanuric acid water slurry;
(2) At 25 °C, 2.02 kg dichlorine monoxide access into isocyanuric acid water slurry, access time is 2h, and then continue the reaction until the reaction system is PH 3.5. Completion of the reaction. From access of dichlorine monoxide until reaction end total consumed time is 6h, obtained reaction liquid containing trichloroisocyanuric acid.
(3) the above reaction liquid fast filtering, the filtrate can be returned to step (1) in a solvent recycling water, solid by washing after 110 °C drying 3 h to obtain the target product of trichloroisocyanuric acid, its effective chlorine content is 91.0percent, consistent with the requirements of the industrial effective content of chlorine (effective chlorine ≥ 88percent), in order to isocyanuric acid as reference, yield is 98percent.
Reference: [1] Patent: CN107141263, 2017, A, . Location in patent: Paragraph 0034-0069
[2] Journal of the Society of Chemical Industry, London, 1948, vol. 67, p. 66
[3] Patent: US2969360, 1958, ,
[4] Yuki Gosei Kagaku Kyokaishi, 1957, vol. 15, p. 241,243[5] Chem.Abstr., 1957, p. 12107
[6] Yuki Gosei Kagaku Kyokaishi, 1957, vol. 15, p. 35,36, 38[7] Chem.Abstr., 1957, p. 10454
[8] Journal of the Society of Chemical Industry, London, 1948, vol. 67, p. 66
[9] Patent: US2969360, 1958, ,
[10] Yuki Gosei Kagaku Kyokaishi, 1957, vol. 15, p. 241,243[11] Chem.Abstr., 1957, p. 12107
[12] Yuki Gosei Kagaku Kyokaishi, 1957, vol. 15, p. 35,36, 38[13] Chem.Abstr., 1957, p. 10454
  • 6
  • [ 108-80-5 ]
  • [ 87-90-1 ]
Reference: [1] Journal of the Chemical Society, 1902, vol. 81, p. 200
[2] Patent: CN205710527, 2016, U, . Location in patent: Paragraph 0014-0016
  • 7
  • [ 108-80-5 ]
  • [ 87-90-1 ]
  • [ 2782-57-2 ]
Reference: [1] , Gmelin Handbook: C: MVol.D1, 39.8.4, page 380 - 380,
[2] Journal of the American Chemical Society, 1963, vol. 85, p. 3101
  • 8
  • [ 108-80-5 ]
  • [ 7782-50-5 ]
  • [ 87-90-1 ]
Reference: [1] Monatshefte fuer Chemie, 1966, vol. 97, p. 115,118, 120
[2] , Gmelin Handbook: C: MVol.D3, 5.6.1, page 146 - 147,
  • 9
  • [ 108-80-5 ]
  • [ 107-18-6 ]
  • [ 1025-15-6 ]
YieldReaction ConditionsOperation in experiment
98.6% With triphenylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 95℃; for 22 h; Inert atmosphere 6.45 g (50 mmol) of isocyanuric acid, 670 mg (2.5 mmol) of triphenylphosphine as an organophosphorus compound and 25.8 g of xylene as a solvent were placed in a reaction vessel, and after purging with nitrogen, a trade name E101 NE / W Manufactured by Evonik Degussa Co., Ltd., palladium-supported activated carbon catalyst supporting a mixture of zero valent metallic palladium and a divalent palladium compound in an amount converted to palladium atoms in terms of palladium atoms) to active charcoal was 266 mg in terms of dry mass , And the mixture was stirred at 95 ° C. for 1 hour. Then, 13.1 g (225 mmol) of allyl alcohol as an alkenyl type alcohol was added dropwise over 1 hour, and the reaction was carried out for 20 hours while returning only the organic layer out of the xylene, allyl alcohol and water azeotropically distilled by Dean Stark into the system. After the reaction, insoluble matter was filtered off. As a result of analyzing the filtrate, 98.6percent of triallyl isocyanurate and 1.4percent of diallyl isocyanurate were formed on the basis of isocyanuric acid, and no monoallyl isocyanurate was produced.
Reference: [1] Patent: JP6288459, 2018, B2, . Location in patent: Paragraph 0018; 0022; 0026-0029; 0031-0032; 0034-0035; 0037
  • 10
  • [ 108-80-5 ]
  • [ 6728-21-8 ]
  • [ 1025-15-6 ]
YieldReaction ConditionsOperation in experiment
68% With sodium carbonate; potassium bromide In dimethyl sulfoxide at 65℃; for 1.5 h; Synthesis Example 3
Isocyanuric acid (135 mg, 1.1 mmol), sodium carbonate (318 mg, 3.0 mmol), potassium bromide (36 mg, 0.3 mmol), and dimethyl sulfoxide (4.1 g) were mixed, and the mixture was heated to 65°C.
A mixed solution of 2-propenyl methanesulfonate (409 mg, 3.0 mmol) and dimethyl sulfoxide (409 mg) was added dropwise over 30 minutes.
A reaction was carried out for 1 hour.
The reaction solution was analyzed by GC, and the yield of 1,3,5-tris-(2-propenyl)-isocyanurate was confirmed to be 68percent.
Reference: [1] Patent: EP2913331, 2015, A1, . Location in patent: Paragraph 0068
  • 11
  • [ 108-80-5 ]
  • [ 107-18-6 ]
  • [ 6294-79-7 ]
  • [ 1025-15-6 ]
YieldReaction ConditionsOperation in experiment
68.1% With triphenylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 95℃; for 8 h; Inert atmosphere 6.45 g (50 mmol) of isocyanuric acid, 670 mg (2.5 mmol) of triphenylphosphine as an organophosphorus compound and 25.8 g of xylene as a solvent were placed in a reaction vessel, and after purging with nitrogen, a trade name E101 NE / W (manufactured by Evonik Degussa Co., Ltd., palladium-supported activated carbon catalyst supporting a mixture of zero valent metallic palladium and divalent palladium compound in terms of palladium atoms in terms of palladium atoms) to 266 mg (125 μmol as the above palladium), and the mixture was stirred at 95 ° C. for 1 hour.Then, 13.1 g (225 mmol) of allyl alcohol as an alkenyl type alcohol was added dropwise over 1 hour, and the reaction was carried out for 6 hours while only the organic layer out of the xylene, allyl alcohol, and water azeotropicaly distilled with Dean Stark was returned to the system.After the reaction, insoluble matter was filtered off.As a result of analyzing the filtrate, 68.1percent of triallyl isocyanurate and 13.0percent of diallyl isocyanurate were formed on the basis of isocyanuric acid, and monoallyl isocyanurate was not produced.
Reference: [1] Patent: JP6288459, 2018, B2, . Location in patent: Paragraph 0019; 0021; 0023-0025; 0030; 0033; 0036
  • 12
  • [ 108-80-5 ]
  • [ 106-95-6 ]
  • [ 1025-15-6 ]
Reference: [1] Patent: EP2774929, 2014, A1, . Location in patent: Paragraph 0211
[2] Patent: US2014/308527, 2014, A1, . Location in patent: Page/Page column
  • 13
  • [ 108-80-5 ]
  • [ 107-05-1 ]
  • [ 1025-15-6 ]
Reference: [1] Synthetic Communications, 1993, vol. 23, # 19, p. 2659 - 2672
  • 14
  • [ 50-00-0 ]
  • [ 108-80-5 ]
  • [ 128-39-2 ]
  • [ 27676-62-6 ]
YieldReaction ConditionsOperation in experiment
92.3% With hexamethylenetetramine In methanol; water at 120 - 140℃; for 6 h; Autoclave; Inert atmosphere To a 1L autoclave with mechanical stirring, thermometer socket, pressure gauge, nitrogen replacement port, 178g of 2,6-di-tert-butylphenol, 24.48g of paraformaldehyde, 41.28g of isocyanuric acid and 4.4g of urotropine were added. 4.4g, under vacuum, nitrogen replacement for more than 3 times, after the last nitrogen replacement, under the condition of negative pressure (-0.01Mpa), 1000mL aqueous solution of 70percent by volume of methanol is pumped into the reactor, and then Nitrogen gas was introduced into the apparatus to a pressure of 0.6 MPa, and the temperature was raised under a nitrogen atmosphere. After the temperature was raised to 120 ° C for 2 hours, the temperature was further raised to 140 ° C for 4 hours, and the reaction was completed. The circulating water of the reaction kettle was cooled to 58 ° C to obtain a crude product, and the crude product was directly filtered, and the solid matter was dissolved in a 70percent by volume aqueous solution of methanol at a concentration of 70 ° C, and recrystallized by cooling, and then anhydrous at 55 ° C. The methanol was washed twice or more and dried to obtain a white crystalline material, which was the target product hindered phenolic antioxidant 3114, and the yield was 92.3percent.
Reference: [1] Patent: CN108707122, 2018, A, . Location in patent: Paragraph 0020; 0021; 0028; 0029
  • 15
  • [ 34557-54-5 ]
  • [ 57-13-6 ]
  • [ 70-47-3 ]
  • [ 56-84-8 ]
  • [ 108-80-5 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 17, p. 4411 - 4418
  • 16
  • [ 108-80-5 ]
  • [ 23500-79-0 ]
  • [ 40601-76-1 ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine In N,N-dimethyl-formamide at 90 - 120℃; for 6.5 h; In a reaction vessel, DMF 39g and cyanuric acid 10.5g were added in one portion, then triethylamine 40.5g was added with stirring, and then the temperature was raised to 90°C.mixture of 62.3 g of previously prepared 4-tert-butyl-2,6-dimethyl-3-hydroxybenzyl chloride and DMF prepared in step (1) was added dropwise thereto. There is a small reflux during the process, and the temperature of the vessel slowly rises, requiring that the temperature does not exceed 102 °C and it will be completed in about 11 / 2 hours. The reaction was then incubated at 100-120°C for approximately 5 hours, and TLC followed the end of the reaction.After the reaction was completed, the salt was filtered off at room temperature, rinsed with a small amount of DMF, and filtered. The solvent was recovered under reduced pressure, 115 g of methanol was added, and 60 g was distilled off at normal pressure under reflux. The temperature was reduced to 1-2° Cand filtered for 30 minutes. A small amount of cold methanol was rinsed and filtered to obtain the product1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione compound yield 85percent,HPLC content 96.5percent and white appearance.
Reference: [1] Patent: CN104557752, 2017, B, . Location in patent: Paragraph 0031-0033
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