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104-47-2

Basic Information
CAS No.: 104-47-2
Name: 4-Methoxybenzyl cyanide
Article Data: 109
Molecular Structure:
Molecular Structure of 104-47-2 (4-Methoxybenzyl cyanide)
Formula: C9H9NO
Molecular Weight: 147.177
Synonyms: Acetonitrile,(p-methoxyphenyl)- (6CI,7CI,8CI);(4-Methoxyphenyl)acetonitrile;(p-Methoxyphenyl)acetonitrile;2-(4-Methoxyphenyl)acetonitrile;4-Methoxybenzeneacetonitrile;NSC 96;PAI 106;p-Anisylacetonitrile;p-Methoxybenzeneacetonitrile;p-Methoxybenzyl cyanide;p-Methoxybenzylnitrile;
EINECS: 203-206-0
Density: 1.053 g/cm3
Melting Point: 8 °C
Boiling Point: 286.5 °C at 760 mmHg
Flash Point: 112 °C
Appearance: Clear colorless to slightly yellow liquid
Hazard Symbols: HarmfulXn; IrritantXi; ToxicT
Risk Codes: 20/21/22-36/37/38-52/53
Safety: 26-36/37/39-61-45
PSA: 33.02000
LogP: 1.76128
Synthetic route

C22H18N2O5

A

104-47-2

p-methoxybenzylnitrile

B

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;A 94%
B 100%
31236-71-2

lysichitalexin

104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With dmap; Sn(thiophenolate)4; tributylphosphine; diethylazodicarboxylate In dichloromethane at 0℃; for 0.0833333h;99%
Multi-step reaction with 3 steps
1: 83 percent / NaNO2, NaOH / methanol / 0 °C
2: 63 percent / Et3N / CH2Cl2 / Ambient temperature
3: 94 percent / Bu3SnH, AIBN / benzene / Heating
View Scheme
Multi-step reaction with 2 steps
1: tris(2,2'-bipyridyl)ruthenium(II)chloride hexahydrate; N-ethyl-N,N-diisopropylamine; magnesium(II) perchlorate / acetonitrile / 12 h / 20 °C / Inert atmosphere; Irradiation
2: triphenylphosphine; iodine / dichloromethane / 8 h / 20 °C / Inert atmosphere
View Scheme
1197-58-6

1-(isocyanomethyl)-4-methoxybenzene

104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
at 520 - 550℃; under 0.01 Torr;98%
With 1,1-Diphenylethylene In various solvent(s) at 210℃; Rate constant; Thermodynamic data; ΔG(excit.) <250 deg C>; ΔH(excit.), ΔS(excit.);101 % Chromat.
With 1,1-diphenylene; chlorobenzene In benzene at 170℃; Rate constant; Thermodynamic data; also at 190, 210 and 230 deg C; ΔHY (excit.), ΔΔHY-H(excit.), ΔSY(excit.), ΔΔSY-H(excit);
6343-93-7

2-(4-methoxyphenyl)acetamide

104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With triethylamine; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate In ethyl acetate at 20℃; for 1h; Inert atmosphere;98%
With thionyl chloride In benzene Reflux;
18494-82-1

2-(4-methoxy-benzyloxy)-tetrahydro-pyran

10442-39-4

tetra-n-butylammonium cyanide

104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 3h; Heating;95%

C9H11Cl2NO

104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With TEA In dichloromethane at 25℃; for 2h;95%
2594-06-1

2-(4-methoxyphenyl)acetohydroxamic acid

104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With phosphorus tribromide In benzene for 5h; Heating;93%
139109-50-5

2-[(Z)-Hydroxyimino]-3-(4-methoxy-phenyl)-propionic acid

104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With 1,1'-carbonyldiimidazole In benzene 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h;93%
92565-78-1

4-methoxy-1-(methoxymethoxy)methyl benzene

10442-39-4

tetra-n-butylammonium cyanide

104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With 1-methyl-3H-imidazolium nitrate at 135 - 140℃; for 0.05h; Microwave irradiation;93%
With phosphotungstic acid at 130 - 142℃; for 0.05h; Microwave irradiation; Ionic liquid; chemoselective reaction;88%
With 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0916667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;82%
10442-39-4

tetra-n-butylammonium cyanide

105-13-5

4-Methoxybenzyl alcohol

104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃;92%
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Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

Specification

The CAS registry number of 4-Methoxybenzyl cyanide is 104-47-2. Its EINECS registry number is 203-206-0. The IUPAC name is 2-(4-methoxyphenyl)acetonitrile. In addition, the molecular formula is C9H9NO and the molecular weight is 147.17. It is also called p-methoxybenzeneacetonitrile. What's more, it is a kind of clear colorless to slightly yellow liquid and belongs to the classes of Aromatic Nitriles; Phenyls & Phenyl-Het; Nitriles. What's more, it should be stored in sealed container, and put in a cool and dry place. The storage place must stay away from oxidant, the fire, heat source and water source.

Physical properties about this chemical are: (1)ACD/LogP: 1.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.36; (4)ACD/LogD (pH 7.4): 1.36; (5)ACD/BCF (pH 5.5): 6.41; (6)ACD/BCF (pH 7.4): 6.41; (7)ACD/KOC (pH 5.5): 131.59; (8)ACD/KOC (pH 7.4): 131.59; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 33.02 Å2; (13)Index of Refraction: 1.519; (14)Molar Refractivity: 42.39 cm3; (15)Molar Volume: 139.6 cm3; (16)Polarizability: 16.8 ×10-24cm3; (17)Surface Tension: 38.9 dyne/cm; (18)Density: 1.053 g/cm3; (19)Flash Point: 112 °C; (20)Enthalpy of Vaporization: 52.56 kJ/mol; (21)Boiling Point: 286.5 °C at 760 mmHg; (22)Vapour Pressure: 0.00263 mmHg at 25°C.

Preparation of 4-Methoxybenzyl cyanide: it can be prepared by p-methoxychlorobenzyl through nitrile reaction. In addition, it also can be obtained by 1-(4-Methoxyphenyl)-2-nitroethane. This reaction will need reagents Sn(SPh)4, Bu3P, DEAD and DMAP, and solvent CH2Cl2. The reaction time is 5 minutes at reaction temperature of 0 °C. The yield is about 99%.

4-Methoxybenzyl cyanide can be obtained by 1-(4-Methoxyphenyl)-2-nitroethane.

Uses of 4-Methoxybenzyl cyanide: it is used as intermediates for antidepressant drug and organic synthesis. And it can be used to get β-(p-methoxybenzene)ethylamine. In addition, it can be used to get ethyl 4-methoxyphenylacetimidate hydrochloride. This reaction will need reagent HCl-gas and solvent ethanol. The reaction time is 72 hours at reaction temperature of 4 °C. The yield is about 97%.

4-Methoxybenzyl cyanide can be used to get ethyl 4-methoxyphenylacetimidate hydrochloride

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. And it is irritating to eyes, respiratory system and skin. Moreover, it is harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). In addition, you should avoid release to the environment and you can refer to special instructions safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: N#CCc1ccc(OC)cc1
(2)InChI: InChI=1/C9H9NO/c1-11-9-4-2-8(3-5-9)6-7-10/h2-5H,6H2,1H3
(3)InChIKey: PACGLQCRGWFBJH-UHFFFAOYAS

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07882,