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| CAS No.: | 103-50-4 |
|---|---|
| Name: | Benzyl ether |
| Molecular Structure: | |
|
|
|
| Formula: | C14H14O |
| Molecular Weight: | 198.265 |
| Synonyms: | Benzylether (8CI);1,1'-[Oxybis(methylene)]bis[benzene];BA (plasticizer);Benzyloxide;Dibenzyl ether;NSC 5931;Plastikator BA;Benzene,1,1'-[oxybis(methylene)]bis-; |
| EINECS: | 203-118-2 |
| Density: | 1.047 g/cm3 |
| Melting Point: | 1.5-3.5 °C(lit.) |
| Boiling Point: | 286.852 °C at 760 mmHg |
| Flash Point: | 135 °C |
| Solubility: | insoluble in water, soluble in ethanol, ethyl ether, chloroform, acetone |
| Appearance: | colourless liquid |
| Hazard Symbols: |
 Xi, N
|
| Risk Codes: | 36/37/38-51/53 |
| Safety: | 23-61 |
| Transport Information: | UN 3082 9/PG 3 |
| PSA: | 9.23000 |
| LogP: | 3.40340 |
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| Conditions | Yield |
|---|---|
| With copper(ll) bromide at 175℃; for 8h; Reagent/catalyst; | 100% |
| With (NH4)2.8H0.9[ε-VMo9.4V2.6O40Bi2]·7.2H2O at 129.84℃; for 3h; Catalytic behavior; Reagent/catalyst; | 97% |
| With benzyl bromide In neat (no solvent) at 120℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Sealed tube; Green chemistry; | 97% |
| Conditions | Yield |
|---|---|
| With triethylsilane; chloro-trimethyl-silane In dichloromethane at 20℃; for 3h; | 100% |
| With triethylsilane; ytterbium(III) triflate In 1,2-dichloro-ethane for 4h; Reflux; | 99% |
| With phenyltellurotrimethylsilane; zinc(II) iodide In benzene for 3h; Ambient temperature; | 96% |
| Conditions | Yield |
|---|---|
| With sodium hydride; N,N-dimethyl-formamide at 20℃; for 24h; | 99% |
| With 18-crown-6 ether; cesium fluoride; bis(tri-n-butyltin)oxide In acetonitrile at 55℃; for 8h; | 71% |
| With aluminum oxide In neat (no solvent) at 25℃; for 25h; | 39% |
| Conditions | Yield |
|---|---|
| With triethylsilane; trifluorormethanesulfonic acid In nitromethane at 20℃; for 0.0166667h; | 99% |
| With triethylsilane; silver tetrafluoroborate at 20℃; for 0.0833333h; Catalytic behavior; Reagent/catalyst; Temperature; Green chemistry; | 98% |
| With 1,1,3,3-Tetramethyldisiloxane; trimethylsilyl trifluoromethanesulfonate In benzene for 0.333333h; Heating; | 97% |
- 70396-63-3, 14313-18-9
1-(5-methylfuran-2-yl)pentan-1-ol
- 100-51-6
benzyl alcohol
A
- 103-50-4
dibenzyl ether
| Conditions | Yield |
|---|---|
| With magnesium(II) perchlorate In diethyl ether for 1h; Ambient temperature; | A n/a B 99% |
| Conditions | Yield |
|---|---|
| With uranyl(VI) triflate In dichloromethane at 20℃; for 1h; Reagent/catalyst; Solvent; Temperature; | A n/a B 99% |
| With aluminium(III) triflate at 20℃; Inert atmosphere; Sonication; neat (no solvent); | A n/a B 100 %Chromat. |
- 766-77-8
Dimethylphenylsilane
- 100-52-7
benzaldehyde
A
- 103-50-4
dibenzyl ether
B
- 56-33-7
1,1,3,3-tetramethyl-1,3-diphenyldisiloxane
| Conditions | Yield |
|---|---|
| With uranyl(VI) triflate In dichloromethane at 20℃; for 1h; | A 99% B n/a |
| Conditions | Yield |
|---|---|
| With uranyl(VI) triflate In dichloromethane at 20℃; for 6h; | A n/a B 99% |
| Conditions | Yield |
|---|---|
| With triethylsilane; iron(III) chloride In nitromethane at 20℃; for 0.166667h; | 98% |
| With triethylsilane; trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - -30℃; | 96% |
| With triethylsilane; bismuth(III) bromide In acetonitrile for 0.0833333h; Ambient temperature; | 84% |
| With triethylsilane; triphenylmethyl perchlorate In dichloromethane at 0℃; | 72% |
- 1228384-40-4
1-((benzyloxy)methyl)-4-iodobenzene
- 103-50-4
dibenzyl ether
| Conditions | Yield |
|---|---|
| With potassium tert-butylate; benzyl alcohol In N,N-dimethyl-formamide at 90℃; for 2h; Schlenk technique; Inert atmosphere; | 97% |
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Consensus Reports
Reported in EPA TSCA Inventory.
Specification
1. Introduction of Benzyl ether
Benzyl ether, with the CAS registry number 103-50-4, is also known as Dibenzyl ether. Its systematic name is benzene,1,1'-[oxybis(methylene)]bis-, its classification code is Skin / Eye Irritant. It should be sealed and stored in a cool and ventilated place. Moreover, it should be protected from oxides, heat and fire. It can be not only used as plasticizer of gas chromatography stationary phase and nitrocellulose, but also used for the preparation of spice.
2. Properties of Benzyl ether
(1)ACD/LogP: 3.47; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.465; (4)ACD/LogD (pH 7.4): 3.465; (5)ACD/BCF (pH 5.5): 253.035; (6)ACD/BCF (pH 7.4): 253.035; (7)ACD/KOC (pH 5.5): 1827.273; (8)ACD/KOC (pH 7.4): 1827.273; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.569; (14)Molar Refractivity: 62.035 cm3; (15)Molar Volume: 189.315 cm3; (16)Polarizability: 24.592×10-24cm3; (17)Surface Tension: 39.86 dyne/cm; (18)Density: 1.047 g/cm3; (19)Flash Point: 135 °C; (20)Enthalpy of Vaporization: 50.489 kJ/mol; (21)Boiling Point: 286.852 °C at 760 mmHg; (22)Vapour Pressure: 0.004 mmHg at 25°C.
3. Structure Descriptors of Benzyl ether
(1)SMILES: c1ccc(cc1)COCc2ccccc2
(2)Std. InChI: InChI=1S/C14H14O/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10H,11-12H2
(3)Std. InChIKey: MHDVGSVTJDSBDK-UHFFFAOYSA-N
4. Toxicity of Benzyl ether
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | oral | 4300mg/kg (4300mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: FOOD INTAKE (ANIMAL) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Toksikologicheskii Vestnik. Vol. (1), Pg. 34, 1997. |
| rat | LD50 | oral | 2500mg/kg (2500mg/kg) | Food and Cosmetics Toxicology. Vol. 16, Pg. 703, 1978. |
5. Safety Information of Benzyl ether
Hazard Symbols:
Xi;
NRisk Codes:
R36/37/38:Irritating to eyes, respiratory system and skin.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Description:
S23:Do not breathe vapour.
S61:Avoid release to the environment. Refer to special instructions /safety data sheets.
6. Preparation of Benzyl ether
Benzyl ether can be prepared by benzaldehyde at the ambient temperature. This reaction will need reagents bismuth bromide, triethylsilane and solvent acetonitrile with the reaction time of 5 min. The yield is about 84%.
![Benzene,1,1'-[oxybis(methylene)]bis- can be prepared by benzaldehyde at the ambient temperature](/UserFilesUpload/Preparation of Benzene,1,1'-[oxybis(methylene)]bis-.jpg)
7. Use of Benzyl ether
Benzyl ether can be used to produce iodomethyl-benzene at the ambient temperature. It will need reagent boron triiodide-N,N-diethylaniline complex and solvent benzene with the reaction time of 2.5 hours. The yield is about 88%.
![Benzene,1,1'-[oxybis(methylene)]bis- can be used to produce iodomethyl-benzene at the ambient temperature](/UserFilesUpload/Uses of Benzene,1,1'-[oxybis(methylene)]bis-.jpg)
8. Other details of Benzyl ether
When you are using Benzyl ether, please be cautious about it as the following:
Benzyl ether is irritating to eyes, respiratory system and skin. It is toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. You should not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). You must avoid releasing it to the environment just refering to special instructions/safety data sheet.