Benzyl ether supplier | CasNO.103-50-4

Name
Benzyl ether
EINECS 203-118-2
CAS No. 103-50-4
Article Data473
CAS DataBase
Density 1.047 g/cm³
Solubility insoluble in water, soluble in ethanol, ethyl ether, chloroform, acetone
Melting Point 1.5-3.5 °C(lit.)
Formula C₁₄H₁₄O
Boiling Point 286.852 °C at 760 mmHg
Molecular Weight 198.265
Flash Point 135 °C
Transport Information UN 3082 9/PG 3
Appearance colourless liquid
Safety 23-61
Risk Codes 36/37/38-51/53
Molecular Structure
Hazard Symbols Xi,N
Synonyms Benzylether (8CI);1,1'-[Oxybis(methylene)]bis[benzene];BA (plasticizer);Benzyloxide;Dibenzyl ether;NSC 5931;Plastikator BA;Benzene,1,1'-[oxybis(methylene)]bis-;
PSA 9.23000
LogP 3.40340

Synthetic route

: 100-51-6
benzyl alcohol

: 103-50-4
dibenzyl ether

Conditions

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%

: 100-52-7
benzaldehyde

: 100-51-6
benzyl alcohol

: 103-50-4
dibenzyl ether

Conditions

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%

: 100-39-0
benzyl bromide

: 103-50-4
dibenzyl ether

Conditions

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%

: 100-52-7
benzaldehyde

: 103-50-4
dibenzyl ether

Conditions

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

B: 2-(1-Benzyloxy-pentyl)-5-methyl-furan

Conditions

Conditions	Yield
With magnesium(II) perchlorate In diethyl ether for 1h; Ambient temperature;	A n/a B 99%

...Expand

: 617-86-7
triethylsilane

: 100-52-7
benzaldehyde

A: 994-49-0
hexaethyl disiloxane

B: 103-50-4
dibenzyl ether

Conditions

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.

...Expand

: 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

Conditions	Yield
With uranyl(VI) triflate In dichloromethane at 20℃; for 1h;	A 99% B n/a

...Expand

: 100-52-7
benzaldehyde

: 789-25-3
HSiPh3

A: 1829-40-9
hexaphenyldisiloxanne

B: 103-50-4
dibenzyl ether

Conditions

Conditions	Yield
With uranyl(VI) triflate In dichloromethane at 20℃; for 6h;	A n/a B 99%

...Expand

: 14642-79-6
benzyloxy-trimethylsilane

: 100-52-7
benzaldehyde

: 103-50-4
dibenzyl ether

Conditions

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

Conditions	Yield
With potassium tert-butylate; benzyl alcohol In N,N-dimethyl-formamide at 90℃; for 2h; Schlenk technique; Inert atmosphere;	97%

: 100-39-0
benzyl bromide

A: 103-50-4
dibenzyl ether

B: 108-95-2
phenol

Conditions

Conditions	Yield
With potassium tert-butylate; trifluoroacetic acid In tetrahydrofuran; dichloromethane; water	A 96% B n/a

: 100-39-0
benzyl bromide

: 172843-34-4
(±)-4-hydroxymethyl-4-vinyl-dihydro-furan-2-one

A: 103-50-4
dibenzyl ether

B: 130838-67-4
4-<(benzyloxy)methyl>-4-<(tert-butyldimethylsiloxy)methyl>tetrahydro-2-furanone

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; ethyl acetate; mineral oil	A n/a B 96%

...Expand

: 937596-55-9
2-(benzyloxy)-5-fluoroaniline

A: 159471-66-6
N-Acetyl-2-benzyloxy-4-fluoroaniline

B: 103-50-4
dibenzyl ether

Conditions

Conditions	Yield
With acetic anhydride In pyridine; (2S)-N-methyl-1-phenylpropan-2-amine hydrate	A 96% B n/a

: 141-97-9
ethyl acetoacetate

: 100-51-6
benzyl alcohol

A: 103-50-4
dibenzyl ether

B: 620-79-1
Ethyl 2-benzylacetoacetate

Conditions

Conditions	Yield
With 12-tungestocobaltic acid supported on nano silica at 80℃; for 0.05h; neat (no solvent);	A n/a B 95%

...Expand

: 67-56-1
methanol

: 100-51-6
benzyl alcohol

A: 538-86-3
benzyl methyl ether

B: 103-50-4
dibenzyl ether

Conditions

Conditions	Yield
With copper(ll) bromide at 175℃; for 10h; Inert atmosphere; Sealed tube;	A 93% B 7%
With phosphoric acid at 350℃; under 36775.4 Torr;
With Cp*Ir(Cl)2(nBu2Im); silver trifluoromethanesulfonate at 110℃; for 12h;	A 88 %Spectr. B 6 %Spectr.

...Expand

: 2-benzyloxy-1-methylpyridinium triflate

: 111-77-3
2-(2-methoxyethoxy)ethyl alcohol

A: 694-85-9
1-methyl-2-pyridone

B: 103-50-4
dibenzyl ether

C: diethylene glycol benzyl methyl diether

Conditions

Conditions	Yield
With α,α,α-trifluorotoluene; magnesium oxide at 83℃; for 24h;	A n/a B n/a C 93%

...Expand

: 6-carboxy-7,8-dihydroxy-3-trifluoroacetyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine

: 100-44-7
benzyl chloride

: 103-50-4
dibenzyl ether

Conditions

Conditions	Yield
With potassium carbonate In N-methyl-acetamide	93%

: 112-53-8
1-dodecyl alcohol

: 100-51-6
benzyl alcohol

A: 4542-57-8
dilauryl ether

B: 103-50-4
dibenzyl ether

C: 39695-18-6
((dodecyloxy)methyl)benzene

Conditions

Conditions	Yield
With Cp*Ir(Cl)2(nBu2Im); silver trifluoromethanesulfonate at 130℃; for 3h;	A n/a B 2 %Spectr. C 93%

...Expand

: 17369-87-8, 18951-36-5, 23053-16-9, 81872-27-7, 87333-63-9, 118204-68-5
methyl (2RS,3RS)-3-hydroxy-2-tetradecyloctadecanoate

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

A: 103-50-4
dibenzyl ether

: methyl (2RS,3RS)-3-benzyloxy-2-tetradecyloctadecanoate

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane; cyclohexane	A n/a B 92%

...Expand

: potassium α-benzyloxymethyltrifluoroborate

: 16156-59-5
phenyl methanesulfonate

: 103-50-4
dibenzyl ether

Conditions

Conditions	Yield
With potassium phosphate; 1,1'-bis(diisopropylphosphino)ferrocene; (2'-amino-[1,1'-biphenyl]-2-yl)palladium(II)chloride dimer In water; tert-butyl alcohol at 110℃; for 20h; Suzuki-Miyaura cross coupling; Inert atmosphere;	92%

: 6748-86-3, 6884-01-1, 6988-45-0, 15384-63-1, 30010-02-7, 32976-12-8, 32976-13-9, 65530-22-5, 65530-24-7, 65530-25-8, 65556-00-5, 69651-81-6, 86420-66-8, 86420-75-9, 99265-93-7, 99265-97-1, 103772-99-2
methyl 4,6-O-benzylidene-β-D-galactopyranoside 2,3-di-O-p-toluenesulfonate

: 100-51-6
benzyl alcohol

A: 140-11-4
Benzyl acetate

B: 103-50-4
dibenzyl ether

C: 1385089-67-7
methyl 3-O-benzyl-4,6-O-benzylidene-β-D-idopyranoside

Conditions

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane for 72h; regioselective reaction;	A n/a B 92% C 64%

...Expand

: 65-85-0
benzoic acid

: 103-50-4
dibenzyl ether

Conditions

Conditions	Yield
With 1,1,3,3-Tetramethyldisiloxane; copper(II) bis(trifluoromethanesulfonate) In methyl cyclohexane at 100℃; for 16h; sealed tube;	91%
With sulfuric acid bei der elektrolytischen Reduktion;

: 123-54-6
acetylacetone

: 100-51-6
benzyl alcohol

A: 1134-87-8
3-benzyl-pentane-2,4-dione

B: 103-50-4
dibenzyl ether

Conditions

Conditions	Yield
With 12-tungestocobaltic acid supported on nano silica at 80℃; for 0.0333333h; neat (no solvent);	A 91% B n/a
With Al3+-exchanged montmorillonite In nitromethane at 100℃; for 0.5h; Product distribution; Further Variations:; Solvents; Reagents;	A 83 % Chromat. B 12 % Chromat.

...Expand

: 71-23-8
propan-1-ol

: 100-51-6
benzyl alcohol

A: 103-50-4
dibenzyl ether

B: 937-61-1
benzyl propyl ether

Conditions

Conditions	Yield
With copper(ll) bromide at 175℃; for 10h; Inert atmosphere; Sealed tube;	A 9% B 91%

...Expand

: 100-51-6
benzyl alcohol

: 71-36-3
butan-1-ol

A: 103-50-4
dibenzyl ether

B: 588-67-0
benzyl 1-butyl ether

Conditions

Conditions	Yield
With copper(ll) bromide at 175℃; for 10h; Temperature; Time; Reagent/catalyst; Inert atmosphere; Sealed tube;	A 8% B 91%

...Expand

: 100-44-7
benzyl chloride

: 100-51-6
benzyl alcohol

: 103-50-4
dibenzyl ether

Conditions

Conditions	Yield
With iron(III) perchlorate at 100℃; for 1h; neat (no solvent);	90%
copper acetylacetonate for 5h; Heating;	60%
at 25 - 45℃; Kinetics; Mechanism; Thermodynamic data; solvolysis in other alcohols; var. conc. and temp.; rate constants; ΔH, ΔS;

: 64-17-5
ethanol

: 100-51-6
benzyl alcohol

A: 103-50-4
dibenzyl ether

B: 539-30-0
1-(ethoxymethyl)benzene

Conditions

Conditions	Yield
With copper(ll) bromide at 175℃; for 10h; Inert atmosphere; Sealed tube;	A 10% B 90%
With sulfuric acid

...Expand

: 100-52-7
benzaldehyde

: 503071-46-3
(benzyloxy)diisopropylsilane

A: 103-50-4
dibenzyl ether

B: 92411-30-8
2,2,4,4,6,6-hexaisopropylcyclotrisiloxane

Conditions

Conditions	Yield
bismuth(III) bromide; chlorodiisopropylsilane In acetonitrile	A 90% B n/a

...Expand

: 100-51-6
benzyl alcohol

A: 103-50-4
dibenzyl ether

B: 100-52-7
benzaldehyde

Conditions

Conditions	Yield
With polystyrene-supported(catecholato) oxoRe cat. act. by iPrOH; dimethyl sulfoxide In toluene for 2h; Heating; Dean-Stark apparatus;	A n/a B 90%
With Cp*Ir(Cl)2(nBu2Im); silver trifluoromethanesulfonate at 130℃; for 12h;	A 10 %Spectr. B 80 %Spectr.
With ruthenium trichloride; 1,3-bis-(diphenylphosphino)propane; nitrobenzene at 150℃; for 16h; Inert atmosphere;

: 444667-48-5
4-benzyloxy-N,N-bis(2-(tert-butyldimethylsilyloxy)ethyl)aniline

: 103-50-4
dibenzyl ether

: 444667-49-6
4-[N,N-bis(2-(tert-butyldimethylsilyloxy)ethyl)amino]phenol

Conditions

Conditions	Yield
palladium-carbon In tetrahydrofuran	100%

: 103-50-4
dibenzyl ether

: 98-88-4
benzoyl chloride

: 120-51-4
benzoic acid benzyl ester

Conditions

Conditions	Yield
With zinc(II) oxide In neat (no solvent) at 0 - 20℃; for 2.5h; Green chemistry;	98%

: 103-50-4
dibenzyl ether

: 108-24-7
acetic anhydride

: 140-11-4
Benzyl acetate

Conditions

Conditions	Yield
With aminosulfonic acid In acetic acid at 60℃; for 4h;	96%
FeCl3-Montmorillonite K-10 at 70℃; for 22h;	94%
sulfuric acid In water at 140℃; for 3h; Conversion of starting material;	79%

: 506-96-7
Acetyl bromide

: 103-50-4
dibenzyl ether

: 140-11-4
Benzyl acetate

Conditions

Conditions	Yield
With lithium bromide In dichloromethane at 30 - 35℃; for 6h; Inert atmosphere;	96%

: 103-50-4
dibenzyl ether

: 100-52-7
benzaldehyde

Conditions

Conditions	Yield
With ferric nitrate at 60℃; for 0.25h;	95%
With nitric acid In dichloromethane at 20℃; for 1h;	92%
With water; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In acetonitrile at 20℃; for 8h;	86%

: 103-50-4
dibenzyl ether

: 57099-04-4
3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

Conditions

Conditions	Yield
In acetic acid	94%

: 103-50-4
dibenzyl ether

: 622-34-4
1-phenylcyanamide

: 1467-21-6
N-phenyl-N'-benzylurea

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid at 40 - 50℃; for 2h; Reagent/catalyst; Solvent; Time; Ritter Amidation;	94%

Benzyl ether Consensus Reports

Reported in EPA TSCA Inventory.

Benzyl ether 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: Irritant

Xi;

N
Risk 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

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

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.

Product Name

Benzyl ether

Synthetic route

Benzyl ether Consensus Reports

Benzyl ether Specification

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