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[ CAS No. 78-09-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 78-09-1
Chemical Structure| 78-09-1
Chemical Structure| 78-09-1
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Product Details of [ 78-09-1 ]

CAS No. :78-09-1 MDL No. :MFCD00009221
Formula : C9H20O4 Boiling Point : -
Linear Structure Formula :- InChI Key :CWLNAJYDRSIKJS-UHFFFAOYSA-N
M.W : 192.25 Pubchem ID :66213
Synonyms :

Calculated chemistry of [ 78-09-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.75
TPSA : 36.92 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) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.09
Log Po/w (XLOGP3) : 1.28
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 1.1
Log Po/w (SILICOS-IT) : 1.25
Consensus Log Po/w : 1.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.31
Solubility : 9.41 mg/ml ; 0.0489 mol/l
Class : Very soluble
Log S (Ali) : -1.65
Solubility : 4.26 mg/ml ; 0.0221 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.06
Solubility : 1.67 mg/ml ; 0.00867 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.69

Safety of [ 78-09-1 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501 UN#:3272
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 78-09-1 ]

* 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 [ 78-09-1 ]
  • Downstream synthetic route of [ 78-09-1 ]

[ 78-09-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 78-09-1 ]
  • [ 1663-61-2 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 562
[2] Chemische Berichte, 1905, vol. 38, p. 562
  • 2
  • [ 78-09-1 ]
  • [ 1079-66-9 ]
  • [ 719-80-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1968, vol. 712, p. 21 - 27
  • 3
  • [ 36749-09-4 ]
  • [ 78-09-1 ]
  • [ 1128-76-3 ]
  • [ 105-37-3 ]
  • [ 105-58-8 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 6, p. 1769 - 1771
  • 4
  • [ 1122-28-7 ]
  • [ 78-09-1 ]
  • [ 133123-67-8 ]
Reference: [1] Synthesis, 1991, # 1, p. 75 - 78
  • 5
  • [ 78-09-1 ]
  • [ 136304-78-4 ]
  • [ 139481-44-0 ]
YieldReaction ConditionsOperation in experiment
84.8% at 78 - 82℃; for 1 - 2 h; Heating / reflux; Industry scale The concentrate of methyl 3-amino-2-N-[(2'-cyanobiphenyl-4-yl)methyl]aminobenzoate [MBA] obtained in Reference Example5, tetraethyl orthocarbonate [TEC] obtained in Reference Example 6 (397 kg) and acetic acid (62 kg) were mixed, and the mixture was heated (78 to 82°C) under reflux for about 1 to 2 hrs..
The reaction solution was cooled, and methanol (1680 L), a 24percent aqueous sodium hydroxide solution (65 L) and water (2030 L) were added..
The mixture was stirred at 60 to 30°C for 2 hours, and the PH was adjusted to 5 to 7..
After cooled to 5°C or lower, the precipitated crystals were separated, and washed with cold water (2500 L) and cold ethyl acetate (500 L) to give first crystals..
The mother liquor and the washing were concentrated under reduced pressure, followed by cooling to 5°C or lower, and the precipitated crystals were separated, and washed with cold ethyl acetate (20 L) to give second crystals..
The first and second crystals were combined, and dissolved in ethyl acetate (4890 L) under reflux..
A seed crystal was added at about 70°C, and cooled to 5 °C.
The crystals were separated, and washed with cold ethyl acetate (200 L), followed by drying to give methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate [BEC](361 kg, 84.8percent). mp. 168.5-169.5°C 1H-NMR(200MHz, CDCl3) δ: 1.42(3H,t), 3.71(3H,s), 4.63(2H,q), 5.59(2H,s), 7.09(2H,d), 7.20(1H,t), 7.45-7.59(5H,m), 7.69-7.80(2H,m), 7.92(1H,dd) IR(KBr) cm-1: 2225, 1725, 1550, 1480, 1430, 1280, 1250, 1040, 760, 750
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2182 - 2195
[2] Patent: EP1420016, 2004, A1, . Location in patent: Page 18-19
[3] Patent: WO2009/157001, 2009, A2, . Location in patent: Page/Page column 3
  • 6
  • [ 78-09-1 ]
  • [ 107582-20-7 ]
  • [ 150058-27-8 ]
YieldReaction ConditionsOperation in experiment
83.1% at 25 - 35℃; for 2 - 3 h; Methyl 2-amino-3-nitrobenzoate (150.0 grams, 0.765 moles) was placed inan autoclave vessel and 1000 mlof ethyl acetate and 75 grams of Raney nickelwere added to the vessel and stirred under a 2-3 kg/cm2 hydrogen pressure for12-15 hours. The catalyst was removed by filtration, and the ethyl acetate wasevaporated under reduced pressure. Acetic acid (170 ml) was added to theresidue, and 180 grams of tetraethylorthocarbonate was slowly added at 25-35°C.The reaction mass was stirred for 2-3 hours, and water (750 ml) was added afterthe reaction mass was cooled to 10°C. The solid was filtered, washed with 150 mlof water, and dried at 50-60°C to get 140 grams (83.1 percent) of methyl 2-ethoxybenzimidazole-7-carboxylate.; 150 grams of 2-Amino-3-nitro-benzoic acid methylester, Raney nickel (75grams), ethyl acetate (1 litre) were charged in an autoclave vessel. 3.0kg/cm2 ofdry hydrogen gas was passed into the reaction suspension for about 20-25 hoursunder agitation. Reaction mass was filtered on celite, followed by washing thecelite with 150 ml of ethyl acetate. Solvent was removed completely from thefiltrate at about 45-50°C by distillation. 171 ml of acetic acid was charged andtetraethylorthocarbonate (180 grams) was added over about 30-45 minutes.Reaction mass was maintained for about 1-3 hours and was cooled to about 0-5°C. 750 ml of water was added over about 15-30 minutes and the separatedsolid was filtered and washed with 150 ml water, followed by 150 ml of ethylacetate. Solid obtained was dried at about 55-65°C for about 10-12 hours to yield140 grams of 2-Ethoxy-3H-benzoimidazole-4-carboxylic acid methylestercompound of Formula (IV).
Reference: [1] Patent: WO2006/15134, 2006, A1, . Location in patent: Page/Page column 15; 16
[2] Patent: CN104876877, 2018, B, . Location in patent: Paragraph 0033; 0069-0072
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