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4-Hydroxybenzyl cyanide

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Name

4-Hydroxybenzyl cyanide

EINECS 238-046-0
CAS No. 14191-95-8 Density 1.167 g/cm3
PSA 44.02000 LogP 1.45828
Solubility slightly soluble in water Melting Point 68-72 °C
Formula C8H7NO Boiling Point 330 °C at 760 mmHg
Molecular Weight 133.15 Flash Point 137.2 °C
Transport Information N/A Appearance light brown solid
Safety 36/37-36/37/39-26 Risk Codes 20/21/22-36/37/38
Molecular Structure Molecular Structure of 14191-95-8 (4-Hydroxybenzyl cyanide) Hazard Symbols HarmfulXn,IrritantXi
Synonyms

Acetonitrile,(p-hydroxyphenyl)- (6CI,8CI);(4-Hydroxyphenyl)acetonitrile;4-(Cyanomethyl)phenol;4-Hydroxybenzeneacetonitrile;4-Hydroxybenzyl cyanide;4-Hydroxybenzylnitrile;NSC 76080;p-Hydroxybenzyl cyanide;p-Hydroxyphenylacetonitrile;a-Cyano-p-cresol;

Article Data 43

4-Hydroxybenzyl cyanide Synthetic route

838-96-0

2-[4-(benzyloxy)phenyl]acetonitrile

14191-95-8

4-cyanomethylphenol

Conditions
ConditionsYield
With tetrachlorosilane; borontrifluoride acetic acid; lithium iodide In toluene; acetonitrile at 70℃; for 2h;98%
107-31-3

Methyl formate

623-05-2

(4-hydroxyphenyl)methanol

14191-95-8

4-cyanomethylphenol

Conditions
ConditionsYield
With sulfuric acid In methanol; dichloromethane; water96%
104-47-2

p-methoxybenzylnitrile

14191-95-8

4-cyanomethylphenol

Conditions
ConditionsYield
Stage #1: p-methoxybenzylnitrile With aluminum (III) chloride In toluene at 20 - 70℃; for 4.33 - 6.5h;
Stage #2: With hydrogenchloride; water In toluene at 20℃;
95.41%
Stage #1: p-methoxybenzylnitrile With aluminium trichloride In toluene at 70℃;
Stage #2: With hydrogenchloride; water at 20℃; Further stages.;
84%
With 1-butylpyridinium bromide at 100℃; Microwave irradiation; Neat (no solvent);84%
623-05-2

(4-hydroxyphenyl)methanol

109-94-4

formic acid ethyl ester

14191-95-8

4-cyanomethylphenol

Conditions
ConditionsYield
In ethanol94%
16532-79-9

4-Bromophenylacetonitrile

14191-95-8

4-cyanomethylphenol

Conditions
ConditionsYield
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;89%
91983-26-5

4-(cyanomethyl)phenylboronic acid

14191-95-8

4-cyanomethylphenol

Conditions
ConditionsYield
With oxygen; triethylamine In acetonitrile under 760.051 Torr; for 24h; Irradiation; Green chemistry;85%
998-30-1

Triethoxysilane

17194-82-0

2-(4-hydroxyphenyl)acetamide

A

14191-95-8

4-cyanomethylphenol

B

C12H30O7Si2

Conditions
ConditionsYield
With C22H48FeOP4 In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Schlenk technique;A 85%
B n/a
17194-82-0

2-(4-hydroxyphenyl)acetamide

14191-95-8

4-cyanomethylphenol

Conditions
ConditionsYield
With Triethoxysilane; C43H50FeP4Si; zinc dibromide In tetrahydrofuran at 40℃; for 30h; Schlenk technique;82%
With diphenylsilane; FeH(PMe3)2(SiPh(NCH2PPh2)2C6H4) In tetrahydrofuran at 70℃; for 24h; Schlenk technique; Inert atmosphere;55%
122-87-2

N-(hydroxyphenyl)glycine

14191-95-8

4-cyanomethylphenol

Conditions
ConditionsYield
With sodium hydroxide In water; N,N-dimethyl-formamide80%
773837-37-9

sodium cyanide

623-05-2

(4-hydroxyphenyl)methanol

14191-95-8

4-cyanomethylphenol

Conditions
ConditionsYield
In N,N-dimethyl-formamide67%
In N,N-dimethyl-formamide at 120℃; for 26h; Inert atmosphere;546 mg
With tetrabutylammomium bromide

4-Hydroxybenzyl cyanide Specification

The IUPAC name of 4-Hydroxybenzyl cyanide is 2-(4-hydroxyphenyl)acetonitrile. With the CAS registry number 14191-95-8, it is also named as p-Hydroxyphenylacetonitrile. The product's categories are Aromatic Nitriles; Aromatics; Inhibitors. Besides, it is light brown solid, which should be stored in a tightly closed container in a ventilated, dark, cool and dry place. In addition, this chemical is slightly soluble in water.

Physical properties about 4-Hydroxybenzyl cyanide are: (1)ACD/LogP: -1.79; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -4.29; (4)ACD/LogD (pH 7.4): -4.29; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 6; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.579; (13)Molar Refractivity: 39.633 cm3; (14)Molar Volume: 119.226 cm3; (15)Polarizability: 15.712 10-24cm3; (16)Surface Tension: 63.898998260498 dyne/cm; (17)Density: 1.452 g/cm3; (18)Flash Point: 183.54 °C; (19)Enthalpy of Vaporization: 68.946 kJ/mol; (20)Boiling Point: 379.872 °C at 760 mmHg

Preparation of 4-Hydroxybenzyl cyanide: this chemical can be prepared by diazotizing and hydrolyzing of Aminopheny-lacetonitrile. The reaction equation is as follows:

Preparation of 4-Hydroxybenzyl cyanide

Uses of 4-Hydroxybenzyl cyanide: this chemical is used as intermediate for atenolol and also used in organic synthesis. Additionally, it can react with Bromomethyl-benzene to get (4-Benzyloxy-phenyl)-acetonitrile.



This reaction needs K2CO3 and Acetone by heating for 17 hours. The yield is 97 %.

When you are using this chemical, please be cautious about it as the following: it is harmful by inhalation, in contact with skin and if swallowed. It is also irritating to eyes, respiratory system and skin. You should wear suitable protective clothing, gloves and eye/face protection when use it. Moreover, in case of contact with eyes, please rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)InChI=1S/C8H7NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5H2;
(2)InChIKey=AYKYOOPFBCOXSL-UHFFFAOYSA-N;
(3)Smilesc1(ccc(O)cc1)CC#N;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LDLo subcutaneous 250mg/kg (250mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Food and Cosmetics Toxicology. Vol. 18, Pg. 159, 1980.

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