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14174-08-4

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14174-08-4 Usage

Chemical Properties

WHITE TRANSPARENT NEEDLES

Uses

2,3,5,6,8,9-hexahydro-1,4,7,10-benzotetraoxacyclododecine is a useful reactant as it acts as a guest mols for the preparation of novel poly(N-?isopropylacrylamide-?co-?benzo-?12-?crown-?4-?acrylamide) (PNB12C4) hydrogel.

Check Digit Verification of cas no

The CAS Registry Mumber 14174-08-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,1,7 and 4 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 14174-08:
(7*1)+(6*4)+(5*1)+(4*7)+(3*4)+(2*0)+(1*8)=84
84 % 10 = 4
So 14174-08-4 is a valid CAS Registry Number.
InChI:InChI=1/C12H16O4/c1-2-4-12-11(3-1)15-9-7-13-5-6-14-8-10-16-12/h1-4H,5-10H2

14174-08-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzo-12-crown 4-Ether

1.2 Other means of identification

Product number -
Other names 2,3-Benzo-1,4,7,10-tetraoxadodec-2-ene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14174-08-4 SDS

14174-08-4Synthetic route

o-hydroxyphenyl 3,6-dioxa-8-bromooctyl ether
77963-44-1

o-hydroxyphenyl 3,6-dioxa-8-bromooctyl ether

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 25℃;94%
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 25℃; Rate constant;94.0 % Spectr.
benzene-1,2-diol
120-80-9

benzene-1,2-diol

triethylene glycol di-(p-toluenesulfonate)
19249-03-7

triethylene glycol di-(p-toluenesulfonate)

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
Stage #1: benzene-1,2-diol With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 50 - 60℃; for 0.5h;
Stage #2: triethylene glycol di-(p-toluenesulfonate) In water; toluene for 6h; Reflux;
52%
Stage #1: benzene-1,2-diol With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Large scale;
Stage #2: triethylene glycol di-(p-toluenesulfonate) In N,N-dimethyl-formamide at 85 - 90℃; Large scale;
28%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating;18%
With lithium hydroxide; sodium hydroxide 1.) THF; Yield given. Multistep reaction;
benzene-1,2-diol
120-80-9

benzene-1,2-diol

1,2-bis(2-chloroethoxy)ethane
112-26-5

1,2-bis(2-chloroethoxy)ethane

A

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

B

dibenzo-24-crown ether
14174-09-5

dibenzo-24-crown ether

Conditions
ConditionsYield
With lithium hydroxide In water; butan-1-ol for 28h; modified Pedersen procedure; Heating;A 26%
B 27%
With lithium hydroxide In water; butan-1-ol at 100℃; for 30h;A 10%
B 7.8%
With sodium hydroxide In water; tert-butyl alcohol for 30h; Heating; Title compound not separated from byproducts;
benzene-1,2-diol
120-80-9

benzene-1,2-diol

1,2-bis(2-chloroethoxy)ethane
112-26-5

1,2-bis(2-chloroethoxy)ethane

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
With lithium hydroxide monohydrate In water; butan-1-ol at 95℃; Inert atmosphere;14.4%
With sodium hydroxide; lithium perchlorate 1.) DMSO, 60 deg C, 15 min, 2.) 110 deg C, 22 h; Yield given. Multistep reaction;
With sodium hydroxide; lithium perchlorate 1) room temperature, 15 min; 2) 110 deg C, 24 h, DMSO; Yield given. Multistep reaction;
Stage #1: benzene-1,2-diol With lithium bromide monohydrate; lithium hydroxide monohydrate In water; butan-1-ol at 20 - 110℃; for 0.1h; Inert atmosphere;
Stage #2: 1,2-bis(2-chloroethoxy)ethane In water; butan-1-ol at 110℃; for 5h; Inert atmosphere;
2,2'-(1,2-phenylenedioxy)diethanol
10234-40-9

2,2'-(1,2-phenylenedioxy)diethanol

1,2-bis-tosyloxyethane
6315-52-2

1,2-bis-tosyloxyethane

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating;13%
2,2'-<1,2-Phenylenbis(oxy)-2,1-ethandiyloxy>bisethanol
99700-26-2

2,2'-<1,2-Phenylenbis(oxy)-2,1-ethandiyloxy>bisethanol

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide; p-toluenesulfonyl chloride In toluene at 70 - 75℃; for 13h;7%
bis(o-phenylene)glycol ditosylate
54535-06-7

bis(o-phenylene)glycol ditosylate

ethylene glycol
107-21-1

ethylene glycol

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating;5%
2-{2-[2-(2-Bromo-ethoxy)-ethoxy]-ethoxy}-phenol anion
87494-76-6

2-{2-[2-(2-Bromo-ethoxy)-ethoxy]-ethoxy}-phenol anion

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
sodium cation In water; dimethyl sulfoxide for 25h;
C12H16O4*CNS(1-)*K(1+)

C12H16O4*CNS(1-)*K(1+)

A

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

B

potassium thioacyanate
333-20-0

potassium thioacyanate

Conditions
ConditionsYield
In acetonitrile at 24.9℃; Equilibrium constant;
C12H16O4*CNS(1-)*Na(1+)

C12H16O4*CNS(1-)*Na(1+)

A

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

B

sodium thiocyanide
540-72-7

sodium thiocyanide

Conditions
ConditionsYield
In acetonitrile at 24.9℃; Equilibrium constant;
C12H16O4*CNS(1-)*Li(1+)

C12H16O4*CNS(1-)*Li(1+)

A

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

B

lithium thiocyanate
556-65-0

lithium thiocyanate

Conditions
ConditionsYield
In acetonitrile at 24.9℃; Equilibrium constant;
C12H16O4*2CNS(1-)*Ca(2+)

C12H16O4*2CNS(1-)*Ca(2+)

A

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

B

calcium thiocyanate
2092-16-2

calcium thiocyanate

Conditions
ConditionsYield
In acetonitrile at 24.9℃; Equilibrium constant;
C12H16O4*CHNS*H3N

C12H16O4*CHNS*H3N

A

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

B

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

Conditions
ConditionsYield
In acetonitrile at 24.9℃; Equilibrium constant;
benzene-1,2-diol
120-80-9

benzene-1,2-diol

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 52 percent / K2CO3 / dimethylformamide / 10 h / 95 - 100 °C
2: 85 percent / aq. NaOH / 3.5 h / 30 - 95 °C
3: 7 percent / aq. NaOH; (nC4H9)4NI; p-TsCl / toluene / 13 h / 70 - 75 °C
View Scheme
2-[2-(2-hydroxyethoxy)ethoxy]phenol
111875-70-8

2-[2-(2-hydroxyethoxy)ethoxy]phenol

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / aq. NaOH / 3.5 h / 30 - 95 °C
2: 7 percent / aq. NaOH; (nC4H9)4NI; p-TsCl / toluene / 13 h / 70 - 75 °C
View Scheme
1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 16 percent / KOH
2: 94.0 percent Spectr. / Me4NOH / dimethylsulfoxide; H2O / 25 °C
View Scheme
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: PBr3, pyridine
2: 16 percent / KOH
3: 94.0 percent Spectr. / Me4NOH / dimethylsulfoxide; H2O / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium hydroxide / tetrahydrofuran / 7 h / 20 °C
2.1: tetrabutylammomium bromide; sodium hydroxide / toluene; water / 0.5 h / 50 - 60 °C
2.2: 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water; tetrahydrofuran / 2 h / 5 °C / Large scale
2.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / Large scale
2.2: 85 - 90 °C / Large scale
View Scheme
((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) dimethanesulfonate
55400-73-2

((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) dimethanesulfonate

benzene-1,2-diol
120-80-9

benzene-1,2-diol

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
Stage #1: benzene-1,2-diol With caesium carbonate In acetonitrile for 3h; Reflux; Inert atmosphere;
Stage #2: ((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) dimethanesulfonate In acetonitrile Inert atmosphere; Reflux;
tantalum(V) oxide

tantalum(V) oxide

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

hydrogen fluoride
7664-39-3

hydrogen fluoride

water
7732-18-5

water

[(benzo-12-crown-4)2*H3O][TaF6]

[(benzo-12-crown-4)2*H3O][TaF6]

Conditions
ConditionsYield
In methanol; hydrogen fluoride aq. HF; Ta2O5 dissolved in 45% aq. HF; 2 equiv. CH3OH soln. of crown ether added; stored at 20-25°C in exsiccator for a low evapn. of solvent over several days; elem. anal.;95%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

tantalum pentafluoride
7783-71-3

tantalum pentafluoride

hydrogen fluoride
7664-39-3

hydrogen fluoride

water
7732-18-5

water

[(benzo-12-crown-4)2*H3O][TaF6]

[(benzo-12-crown-4)2*H3O][TaF6]

Conditions
ConditionsYield
In hydrogen fluoride aq. HF; TaF5 in aq. 45% HF added to soln. of crown ether; stored at 20-25°C in exsiccator for a low evapn. of solvent over several days;95%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

5-nitroisatin
611-09-6

5-nitroisatin

C32H34N2O11
1366625-22-0

C32H34N2O11

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In chloroform at 25℃; regioselective reaction;95%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

tert-butyl alcohol
75-65-0

tert-butyl alcohol

12-(tert-butyl)-2,3,5,6,8,9-hexahydrobenzo[b][1,4,7,10]tetraoxacyclododecine
98987-34-9

12-(tert-butyl)-2,3,5,6,8,9-hexahydrobenzo[b][1,4,7,10]tetraoxacyclododecine

Conditions
ConditionsYield
With sulfuric acid In chloroform Product distribution; Heating; different solvents, other crown ethers;94%
With sulfuric acid In chloroform Heating;94%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

3-(p-tolyl)-1,2,4-triazin-5(2H)-one
36993-93-8

3-(p-tolyl)-1,2,4-triazin-5(2H)-one

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-3-p-tolyl-1-trifluoroacetyl-1,6-dihydro-4H-[1,2,4]triazin-5-one
420118-14-5

6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-3-p-tolyl-1-trifluoroacetyl-1,6-dihydro-4H-[1,2,4]triazin-5-one

Conditions
ConditionsYield
In trifluoroacetic acid at 20℃; for 3h;94%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

2-nitro-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxabenzocyclododecene
78554-67-3

2-nitro-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxabenzocyclododecene

Conditions
ConditionsYield
With nitric acid In chloroform; acetic acid at 20℃; for 6h;93%
With nitric acid In acetonitrile for 0.5h; Heating;92%
With nitric acid; acetic acid In chloroform at 20℃; for 24h; Cooling with ice;75%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Na[Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]

Na[Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]

[Na(benzo-12-crown-4)2][Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]

[Na(benzo-12-crown-4)2][Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]

Conditions
ConditionsYield
In diethyl ether at 23℃; for 1h;91%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

diethyl ether
60-29-7

diethyl ether

[(Et2O)Na(OC)Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]2

[(Et2O)Na(OC)Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]2

[(benzo-12-crown-4)2Na]{Na[(OC)Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]2}

[(benzo-12-crown-4)2Na]{Na[(OC)Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]2}

Conditions
ConditionsYield
Stage #1: benzo-12-crown-4; [(Et2O)Na(OC)Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]2 at 23℃; for 0.0833333h;
Stage #2: diethyl ether for 0.5h;
84%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

2,6-dimethylphenyl isonitrile
119072-54-7, 2769-71-3

2,6-dimethylphenyl isonitrile

Na[Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]

Na[Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]

[(benzo-12-crown-4)2Na][(XylNC)Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]

[(benzo-12-crown-4)2Na][(XylNC)Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)]

Conditions
ConditionsYield
Stage #1: benzo-12-crown-4; 2,6-dimethylphenyl isonitrile; Na[Re(η5-Cp)(N,N′-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate)] In diethyl ether at 23℃; for 0.0833333h;
Stage #2: for 0.25h; Further stages;
82%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

chloroacetyl chloride
79-04-9

chloroacetyl chloride

C14H17ClO5

C14H17ClO5

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 2h;79%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

12-bromo-2,3,5,6,8,9-hexahydrobenzo[b][1,4,7,10]-tetraoxacyclododecine
118409-81-7

12-bromo-2,3,5,6,8,9-hexahydrobenzo[b][1,4,7,10]-tetraoxacyclododecine

Conditions
ConditionsYield
With dioxane dibromide In tetrahydrofuran for 0.166667h;78%
With bromine In 1,4-dioxane Bromination;
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

3-phenyl-1,2,4-triazin-5-one
54673-30-2

3-phenyl-1,2,4-triazin-5-one

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

4-(5-Oxo-1-trifluoroacetyl-3-phenyl-1,2,5,6-tetrahydro-1,2,4-triazin-6-yl)benzo-12-crown-4

4-(5-Oxo-1-trifluoroacetyl-3-phenyl-1,2,5,6-tetrahydro-1,2,4-triazin-6-yl)benzo-12-crown-4

Conditions
ConditionsYield
at 20℃; for 1h; Substitution; Acylation;77%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

3-phenyl-1,2,4-triazin-5-one
54673-30-2

3-phenyl-1,2,4-triazin-5-one

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

6-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-3-phenyl-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one

6-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-3-phenyl-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one

Conditions
ConditionsYield
In trifluoroacetic acid at 20℃; for 3h;77%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

indan-1,2,3-trione hydrate
485-47-2

indan-1,2,3-trione hydrate

C33H34O10
1366625-24-2

C33H34O10

Conditions
ConditionsYield
With sulfuric acid In chloroform at 25℃; regioselective reaction;77%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

acetic anhydride
108-24-7

acetic anhydride

1-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-ethanone
107996-83-8

1-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-ethanone

Conditions
ConditionsYield
With PPA In acetic acid at 60℃;76%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

C36H42O12

C36H42O12

Conditions
ConditionsYield
With iron(III) chloride; dipotassium peroxodisulfate at 10 - 15℃; for 2h;75.6%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecene-2-sulfonyl chloride
126867-37-6

6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecene-2-sulfonyl chloride

Conditions
ConditionsYield
With chlorosulfonic acid In chloroform for 6h; Ambient temperature;75%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

1,3,4,6-bis(2-oxapropylene)tetrahydro-3a,6a-diphenylimidazo<4,5-d>imidazole-2,5(1H,3H)-dione
111380-75-7

1,3,4,6-bis(2-oxapropylene)tetrahydro-3a,6a-diphenylimidazo<4,5-d>imidazole-2,5(1H,3H)-dione

28b,28c-diphenyl-2,3,5,6,8,9,12,14,17,18,20,21,23,24,27,28b,28c,29-octadecahydro-1,4,7,10,16,19,22,25-octaoxa-12a,13a,27a,28a-tetraazacyclododeca[1',2':4,5]benzo[1,2-f]cyclododeca[1'',2'':4',5']benzo[1',2':5,6]azuleno[2,1,8-ija]azulene-13,28-dione
1380508-63-3

28b,28c-diphenyl-2,3,5,6,8,9,12,14,17,18,20,21,23,24,27,28b,28c,29-octadecahydro-1,4,7,10,16,19,22,25-octaoxa-12a,13a,27a,28a-tetraazacyclododeca[1',2':4,5]benzo[1,2-f]cyclododeca[1'',2'':4',5']benzo[1',2':5,6]azuleno[2,1,8-ija]azulene-13,28-dione

Conditions
ConditionsYield
With polyphosphoric acid at 80 - 85℃; for 0.5h;75%
With polyphosphoric acid at 80℃;
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

Bromoacetaldehyde diethyl acetal
2032-35-1

Bromoacetaldehyde diethyl acetal

C26H32O8

C26H32O8

Conditions
ConditionsYield
Stage #1: benzo-12-crown-4; Bromoacetaldehyde diethyl acetal With sulfuric acid; acetic acid at 0 - 20℃;
Stage #2: In pentan-1-ol for 6h; Reflux;
71%
Stage #1: benzo-12-crown-4; Bromoacetaldehyde diethyl acetal With sulfuric acid; acetic acid
Stage #2: In pentan-1-ol Heating;
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

1-acetyl-3-p-tolyl-1,6-dihydro-4H-[1,2,4]triazin-5-one

1-acetyl-3-p-tolyl-1,6-dihydro-4H-[1,2,4]triazin-5-one

1-acetyl-6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-3-p-tolyl-1,6-dihydro-4H-[1,2,4]triazin-5-one
420118-24-7

1-acetyl-6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-3-p-tolyl-1,6-dihydro-4H-[1,2,4]triazin-5-one

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3h;69%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

hexamethylenetetramine
100-97-0

hexamethylenetetramine

2,3-(4-formylbenzo)-1,4,7,10-tetraoxa-2-cyclododecene
84993-16-8

2,3-(4-formylbenzo)-1,4,7,10-tetraoxa-2-cyclododecene

Conditions
ConditionsYield
With trifluoroacetic acid at 90 - 95℃; for 24h;68%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

3-ethylsulfanyl-4H-[1,2,4]triazin-5-one
89179-74-8

3-ethylsulfanyl-4H-[1,2,4]triazin-5-one

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

3-Ethylsulfanyl-6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one

3-Ethylsulfanyl-6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one

Conditions
ConditionsYield
In trifluoroacetic acid at 20℃; for 6h;65%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

acetic acid
64-19-7

acetic acid

A

1-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-ethanone
107996-83-8

1-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-ethanone

B

2,3-(4,5-diacetyl)benzo-12-crown-4 ether

2,3-(4,5-diacetyl)benzo-12-crown-4 ether

Conditions
ConditionsYield
With polyphosporic acid at 80℃; for 0.666667h;A 64%
B n/a
With PPA at 80℃; for 1.25h;A n/a
B 62%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

propionic acid
802294-64-0

propionic acid

A

1-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-propan-1-one

1-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-propan-1-one

B

1-(3-Propionyl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-propan-1-one

1-(3-Propionyl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-propan-1-one

Conditions
ConditionsYield
With PPA at 80℃;A n/a
B 64%
With PPA at 80℃;
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

3-(4-Chlorophenyl)-2H-1,2,4-triazin-5-one

3-(4-Chlorophenyl)-2H-1,2,4-triazin-5-one

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

3-(4-Chloro-phenyl)-6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one

3-(4-Chloro-phenyl)-6-(6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-1-(2,2,2-trifluoro-acetyl)-1,6-dihydro-4H-[1,2,4]triazin-5-one

Conditions
ConditionsYield
In trifluoroacetic acid at 20℃; for 6h;64%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

(4aR,14aS)-Dodecahydro-5,8,11,14-tetraoxa-benzocyclododecene
17454-42-1, 125279-92-7, 125356-38-9

(4aR,14aS)-Dodecahydro-5,8,11,14-tetraoxa-benzocyclododecene

Conditions
ConditionsYield
With hydrogen; (PAA)6RhCl In water; isopropyl alcohol under 760 Torr;60%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

1-adamanthanol
768-95-6

1-adamanthanol

2-Adamantan-1-yl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecene

2-Adamantan-1-yl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In 1,4-dioxane Heating;59%
benzo-12-crown-4
14174-08-4

benzo-12-crown-4

butyric acid
107-92-6

butyric acid

A

1-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-butan-1-one

1-(6,7,9,10,12,13-Hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-butan-1-one

B

1-(3-Butyryl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-butan-1-one

1-(3-Butyryl-6,7,9,10,12,13-hexahydro-5,8,11,14-tetraoxa-benzocyclododecen-2-yl)-butan-1-one

Conditions
ConditionsYield
With PPA at 80℃;A 57%
B n/a
With PPA at 80℃; for 0.666667h;
sulfur
10544-50-0

sulfur

benzo-12-crown-4
14174-08-4

benzo-12-crown-4

sodium amalgam

sodium amalgam

(K[Mo(13)C(N(CH3(C(2)H3)2C)(C6H3(CH3)2))3])2

(K[Mo(13)C(N(CH3(C(2)H3)2C)(C6H3(CH3)2))3])2

Na(1+)*2(C4H4(C2O)(C2H4O)3)*[Mo(13)CS(N(CH3(C(2)H3)2C)(C6H3(CH3)2))3](1-)=[Na(C24H32O8)][Mo(13)CS(N(C4H3(2)H6)(C8H9))3]

Na(1+)*2(C4H4(C2O)(C2H4O)3)*[Mo(13)CS(N(CH3(C(2)H3)2C)(C6H3(CH3)2))3](1-)=[Na(C24H32O8)][Mo(13)CS(N(C4H3(2)H6)(C8H9))3]

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether; benzene stirring of (KMo(13)C(N(C(CD3)2CH3)(C6H3Me2))3)2 in C6H6/ether at -35°C, addn. of S8; stirring for 2 h; filtration, drying, transferring to vial with Na/Hg in THF, filtration after 2 h, drying, dissolving in soln. of benzo-12-crown-4 (2 equiv.); in 1:1 benzene/ether; pptn., recrystn. from 3:2 pentane/THF; elem. anal.;56%

14174-08-4Relevant articles and documents

Two new "onium" fluorosilicates, the products of interaction of fluorosilicic acid with 12-membered macrocycles: Structures and spectroscopic properties

Gelmboldt, Vladimir O.,Ganin, Eduard V.,Fonari, Marina S.,Simonov, Yurii A.,Koroeva, Larisa V.,Ennan, Alim A.,Basok, Stepan S.,Shova, Sergiu,Kaehlig, Hanspeter,Arion, Vladimir B.,Keppler, Bernhard K.

, p. 2915 - 2924 (2007)

Two novel compounds, (L1H)2[SiF6] ·2H2O (1) and (L2H)2[SiF 5(H2O)]2·3H2O (2), resulting from the reactions of H2SiF6 with 4′-aminobenzo-12- crown-4 (L1) and monoaza-12-crown-4 (L2), respectively, were studied by X-ray diffraction and characterised by IR and 19F NMR spectroscopic methods. Both complexes have ionic structures due to the proton transfer from the fluorosilicic acid to the primary amine group in L1 and secondary amine group incorporated into the macrocycle L2. The structure of 1 is composed of [SiF6]2- centrosymmetric anions, N-protonated cations (L1H)+, and two water molecules, all components being bound in the layer through a system of NH...F, NH...O and OH...F hydrogen bonds. The [SiF 6]2- anions and water molecules are assembled into inorganic negatively-charged layers via OH...F hydrogen bonds. The structure of 2 is a rare example of stabilisation of the complex anion [SiF 5(H2O)]-, the labile product of hydrolytic transformations of the [SiF6]2- anion in an aqueous solution. The components of 2, i.e., [SiF5(H2O)] -, (L2H)+, and water molecules, are linked by a system of NH...F, NH...O, OH...F, OH...O hydrogen bonds. In a way similar to 1, the [SiF5(H2O)]- anions and water molecules in 2 are combined into an inorganic negatively-charged layer through OH...F and OH...O interactions. The Royal Society of Chemistry.

Photoresponsive Crown Ethers. 4. Influence of Alkali Metal Cations on Photoisomerization and Thermal Izomerization of Azobis(benzocrown ether)s

Shinkai, Seiji,Ogawa, Toshiyuki,Kusano, Yumiko,Manabe, Osamu,Kikukawa, Kiyoshi,et al.

, p. 1960 - 1967 (1982)

Five photoresponsive azobis(benzocrown ether)s 1(4,4), 1(5,5), 1(6,6), 2(5,5) and 2(6,6), were synthesized, where numbers in parentheses denote the number of oxygens in benzocrown ethers, and crown series 2 have two tert-butyl groups in the 2 and 2' position of the azo linkage.We have found that (i) in the presence of alkali metal cations, the concentration of cis isomers (cis percent) under the photostationary state is enhanced and the rate of thermal cis-to-trans isomerization (k) is supressed, the optima cis-1(5,5) and cis-1(6,6) being observed for Rb+ and Cs+, respectively, (ii) Rb+ and Cs+ are extracted most efficiently from an aqueous solution to an organic phase (o-dichlorobenzene) with cis-1(5,5) and cis-1(6,6), respectively, (iii) cis percent and k of 2(5,5) and 2(6,6) are affected by alkyli metal cations smaller than those of corresponding 1(5,5) and 1(6,6), and (iv) cis percent and k of 1(4,4) are less affected by added alkali metal cations and the extractability is very low.The increase in cis percent and the supression of the thermal isomerization rate are rationalized in terms of the "tying effect" of complexed cations requiring the additional energy to disrupt the crown-cation interaction.The correlation of the extractability with cis percent and k implies that alkali metal cations are extracted under photoirradiation as intramolecular 1:2 cation/crown complexes and the ion selectivity is associated with the fitness between the ion size and the size of the spatial cavity provided by two crown ethers of cis form.The ion selectivity suggests (i) the cavity size of cis-1(6,6) is greater than that of cis-(5,5) and (ii) the cavity sizes of crown series 2 are smaller than those of crown series 1 probably owing to the steric repulsion of the tert-butyl groups.Hence, the ion selectivity in the photocontrolled solvent extraction is effected by the crown ring size and the steric crowding around the azo linkage.

Fingolimod derivatives containing crown ether and bis (2 - methoxyethoxy) structure (by machine translation)

-

Paragraph 0023; 0033-0040, (2020/06/20)

The invention synthesizes a series of fingolimod derivatives containing crown ether or bis (2 - methoxyethoxy) structure by modifying the structure of the immunosuppressant fingolimod for treating multiple sclerosis in the market. The hypoglycemic effect of the target compound was evaluated by in vivo animal experiments. The results show that the compounds including 1c - 1e, Ic-Ie have a certain effect of reducing blood sugar and have application prospects in the preparation of medicines for treating diabetes. (by machine translation)

SUBSTITUTED PYRIMIDINES, PHARMACEUTICAL COMPOSITIONS AND THERAPEUTIC METHODS THEREOF

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Paragraph 00232, (2019/03/17)

The invention provide novel pyrimidine derivatives and analogs having inhibitory activities towards certain tyrosine kinases, e.g., Bruton's tyrosine kinase (Btk) and/or Focal adhesion kinase (FAK), extracellular signal-regulated kinase (ERK), pharmaceutical compositions thereof, and methods of treatment, reduction or prevention of certain diseases or conditions mediated by such by tyrosine kinases, e.g., cancers, tumors, fibrosis, inflammatory diseases, autoimmune diseases, diabetes, or immunologically mediated diseases.

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