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14174-08-4

Basic Information
CAS No.: 14174-08-4
Name: BENZO-12-CROWN-4
Article Data: 16
Molecular Structure:
Molecular Structure of 14174-08-4 (BENZO-12-CROWN-4)
Formula: C12H16O4
Molecular Weight: 224.257
Synonyms: Benzo-12-crown-4 ether;Benzo-12-crown-4;
Density: 1.084 g/cm3
Melting Point: 42-45 °C(lit.)
Boiling Point: 341.8 °C at 760 mmHg
Flash Point: 136.4 °C
Appearance: white transparent needles
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 36/37/38
Safety: 22-24/25-36-26
PSA: 36.92000
LogP: 1.49100
Synthetic route
77963-44-1

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

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.
120-80-9

benzene-1,2-diol

19249-03-7

triethylene glycol di-(p-toluenesulfonate)

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;
120-80-9

benzene-1,2-diol

112-26-5

1,2-bis(2-chloroethoxy)ethane

A

14174-08-4

benzo-12-crown-4

B

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;
120-80-9

benzene-1,2-diol

112-26-5

1,2-bis(2-chloroethoxy)ethane

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;
10234-40-9

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

6315-52-2

1,2-bis-tosyloxyethane

14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating;13%
99700-26-2

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

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%
54535-06-7

bis(o-phenylene)glycol ditosylate

107-21-1

ethylene glycol

14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating;5%
87494-76-6

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

14174-08-4

benzo-12-crown-4

Conditions
ConditionsYield
sodium cation In water; dimethyl sulfoxide for 25h;

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

A

14174-08-4

benzo-12-crown-4

B

333-20-0

potassium thioacyanate

Conditions
ConditionsYield
In acetonitrile at 24.9℃; Equilibrium constant;

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

A

14174-08-4

benzo-12-crown-4

B

540-72-7

sodium thiocyanide

Conditions
ConditionsYield
In acetonitrile at 24.9℃; Equilibrium constant;
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Specification

This chemical is called 2,3,5,6,8,9-Hexahydro-1,4,7,10-benzotetraoxacyclododecine, and its CAS registry number is 14174-08-4. With the molecular formula of C12H16O4, its product categories are Crown Ethers; Functional Materials; Macrocycles for Host-Guest Chemistry; Chelation/Complexation Compounds; Crown Ethers; Synthetic Reagents. In addition, this chemical should be sealed in the cool and dry place.

Other characteristics of the 2,3,5,6,8,9-Hexahydro-1,4,7,10-benzotetraoxacyclododecine can be summarised as followings: (1)ACD/LogP: 0.78; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.78; (4)ACD/LogD (pH 7.4): 0.78; (5)ACD/BCF (pH 5.5): 2.32; (6)ACD/BCF (pH 7.4): 2.32; (7)ACD/KOC (pH 5.5): 63.48; (8)ACD/KOC (pH 7.4): 63.48; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 36.92 Å2; (13)Index of Refraction: 1.479; (14)Molar Refractivity: 58.68 cm3; (15)Molar Volume: 206.8 cm3; (16)Polarizability: 23.26×10-24cm3; (17)Surface Tension: 37.5 dyne/cm; (18)Density: 1.084 g/cm3; (19)Flash Point: 136.4 °C; (20) Enthalpy of Vaporization: 56.23 kJ/mol; (21)Boiling Point: 341.8 °C at 760 mmHg; (22)Vapour Pressure: 0.000155 mmHg at 25°C.

Production method of this chemical: The 2,3,5,6,8,9-Hexahydro-1,4,7,10-benzotetraoxacyclododecine could be obtained by the reactant of o-hydroxyphenyl 3,6-dioxa-8-bromooctyl ether. This reaction needs the reagent of Me4NOH, and the solvent of dimethylsulfoxide and H2O. The yield is 94 %. In addition, this reaction should be taken at the temperature of 25 °C.

Uses of this chemical: The dodecahydro-5,8,11,14-tetraoxa-benzocyclododecene could be obtained by the reactant of 2,3,5,6,8,9-Hexahydro-1,4,7,10-benzotetraoxacyclododecine. This reaction needs the reagent of H2, and the solvent of H2O, propan-2-ol. The yield is 60 %.

When you are using this chemical, please be cautious about it as the following: This chemical is harmful / irritating to eyes, respiratory system and skin. Don't breathe dust. You should wear suitable protective clothing to avoid contacting with skin and eyes. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure: 
1.SMILES: O1c2c(OCCOCCOCC1)cccc2
2.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
3.InChIKey: OAJNZFCPJVBYHB-UHFFFAOYAZ