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Dibenzo-18-crown-6

Dibenzo-18-crown-6 structure

CAS No:
14187-32-7
Formula:
C20H24O6
Chemical Name:
Dibenzo-18-crown-6
Synonyms:
Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin,6,7,9,10,17,18,20,21-octahydro-;6,7,9,10,17,18,20,21-Octahydrodibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin;Crown 18;Dibenzo-18-crown-6;Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecane;2,3:11,12-Dibenzo-1,4,7,10,13,16-hexaoxacyclooctadecane;NSC 147771;Tin(II) ionophore I;54765-16-1;63172-39-4;66105-26-8;73128-69-5
Categories:
Chemical Reagents > Organic Reagents

Description

white to slightly beige fluffy powder

Dibenzo-18-crown-6 is a crown ether that is 18-crown-6 ortho-fused to two benzene rings at positions 8-9 and 17-18. It has a role as a phase-transfer catalyst. It is a member of benzenes and a crown ether.

Dibenzo-18-crown-6 Basic Attributes

Molecular Weight：

360.4

Exact Mass：

360.40

BRN：

1162153

EC Number：

238-041-3

UNII：

0A7W45JCS9

NSC Number：

147771

DSSTox ID：

DTXSID6022428

HScode：

29329995

Characteristics

PSA：

55.4

XLogP3：

2.2

Appearance：

White to slightly beige Fluffy Powder

Density：

1.400 g/cm³

Melting Point：

162-164 °C

Boiling Point：

380-384 °C (679 mmHg)

Flash Point：

380-384°C/679mm

Refractive Index：

1.5200 (estimate)

Water Solubility：

H2O: sparingly soluble

Storage Conditions：

Store below +30°C.

Vapor Pressure：

3.65E-10mmHg at 25°C

Toxicity：

LD50 orally in Rabbit: 2600 mg/kg

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36-36/37/38-20/21/22

safety instructions：

26-37/39-36

RTECS Number：

HP5386000

Marks：

Xi,Xn

Hazard note：

Irritant

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (32.79%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 61 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

dibenzo-18-crown-6

Dibenzo-18-crown-6 Use and Manufacturing

Methods of Manufacturing

General procedure: Prepared using general procedure 2, re-crystallized in methanol. Yields (Open vessel, std. temp control mode: 35percent, power/time mode: 13percent; Closed vessel, std temp control:54percent, power/time mode: 60percent). White crystals. Melting point:148-150°C, (Lit.[2] 150-152°C). IR (KBr disc cm-1): 1040-1120 (-CO). 1H NMR (400 MHz, CDCl3) (ppm): 2.26 (q, 4H, J=5.6 Hz, -CH2-), 4.24 (t, 8H, J=5.6 Hz, -CH2-), 6.89-6.91 (m, 8H, aromatic). 13C NMR (100 MHz, CDCl3)(ppm): 29.28, 67.32, 115.58, 121.72, 149.44. Anal. Calc. forC18H20O4: C, 71.98; H, 6.71; O, 21.31. Found: C, 72.39; H, 6.25; O, 21.36. The 2-step MW was performed similarly but using the diphenol intermediates in lieu of catechol as precursor. Either symmetric or asymmetric DBCEs (2-6) can be obtained through this method depending on the alkyl dihalide used for the ring closure reaction.A suspension of 4 (1.0g, 3.45mmol) and KGeneral procedure: One-pot MAOS of symmetric crown ethers (1-3) areshown in (Scheme 1) whereas two-step MW methods areshown in (Scheme 2). In the two-step MW syntheses, theprepared intermediates A and B described in (Scheme 3)were used as precursors.Symmetric DBCEs (1-3) can be prepared via single stepMAOS, which involved the reaction of catechol with alkyldihalides (i.e. dibromopropane, bis(2-chloroethyl)ether, etc.)at an appropriate molar ratio in the presence of a base inDMSO. For example, DBCEs 1-3 were prepared by reacting10 mmol of catechol and 10 mmol of dibromopropane or bis(2-chloroethyl)ether with 20 mmol of a base in 2 mL DMSO.The reactant was vortex-mixed prior to MW irradiation.22 g (0.2 mol) of catechol, 30.03 g (0.21 mol) 1- chloro-2- (2-chloroethoxy) ethane and 110.4 g potassium carbonate was placed 500 mL round-bottomed flask, was added 350 mL N, N- dimethylformamide (DMF) solution, and the reaction was heated at reflux, the reaction was stirred for 24 h.Cooled to room temperature, poured into large amount of water, extracted with methylene chloride three times.The organic layer was washed with water, dried over anhydrous magnesium sulfate and distilled to remove the organic solvent.Column chromatography (silica gel as the stationary phase, petroleum ether: ethyl acetate = 4: 1 as eluant) to give a white solid 7.57 g, yield 21percent.

Uses

Phase transfer catalyst for the synthesis of monoazaporphyrin. Used for ion transmembrane migration 2 and as a reagent for preparing liquid crystal polyester synthons.

Manufacturing Info：

Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, 6,7,9,10,17,18,20,21-octahydro-: ACTIVE

Computed Properties

Molecular Weight:360.4
XLogP3:2.2
Hydrogen Bond Acceptor Count:6
Exact Mass:360.15728848
Monoisotopic Mass:360.15728848
Topological Polar Surface Area:55.4
Heavy Atom Count:26
Complexity:300
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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