4-Hydroxybenzyl cyanide Chemical Properties

Melting point:

67-70 °C (lit.)

Boiling point:

330 °C/756 mmHg (lit.)

Density 

1.1475 (rough estimate)

refractive index 

1.5260 (estimate)

Flash point:

178 °C

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, DMSO, Methanol (Slightly)

pka

9.63±0.13(Predicted)

form 

Solid

color 

Light Brown to Beige

Water Solubility 

slightly soluble

BRN 

1934470

Exposure limits

NIOSH: IDLH 25 mg/m3

InChIKey

AYKYOOPFBCOXSL-UHFFFAOYSA-N

LogP

0.591 (est)

CAS DataBase Reference

14191-95-8(CAS DataBase Reference)

NIST Chemistry Reference

4-Hydroxyphenylacetic acid nitrile(14191-95-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

36/37-36/37/39-26

RIDADR 

3439

WGK Germany 

3

RTECS 

AM0530000

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269095

MSDS

• Language:English Provider:4-Hydroxybenzyl cyanide
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4-Hydroxybenzyl cyanide Usage And Synthesis

Chemical Properties

Light Brown Solid

Uses

4-Hydroxyphenylacetonitrile (cas# 14191-95-8) is a compound useful in organic synthesis.

Definition

ChEBI: A hydroxynitrile that is phenylacetonitrile substituted by a hydroxy group at position 4.

Synthesis

General procedure for the synthesis of 2-(4-hydroxyphenyl)acetonitrile from 2-(4-methoxyphenyl)acetonitrile: 2-(4-methoxyphenyl)acetonitrile (500 g, 3.397 mol) was slowly added to a stirred suspension of aluminum chloride (1358.86 g, 10.19 mol) in toluene (2100 ml) over a period of 20-30 min at room temperature. The reaction mixture was gradually warmed up to 70°C and maintained at this temperature for 4-6 hours. The reaction progress was monitored by TLC (unfolding agent: 5% ethyl acetate/hexane). Upon completion of the reaction, the mixture was slowly poured into pre-cooled aqueous hydrochloric acid solution (3000 ml of water; 667 ml of concentrated hydrochloric acid), keeping the temperature below 20°C. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 500 ml). The organic layers were combined, washed with water (2 x 500 ml) and dried over anhydrous sodium sulfate (50 g). The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was stirred with a mixture of hexane (800 ml) and ethyl acetate (40 ml) for 1 h. The solid product was collected by filtration and washed with hexane (300 ml). The resulting light brown product was dried under vacuum at 35-40°C. Yield: 431.6 g (95.41% yield); HPLC purity: 99.56%; Melting point: 70-71.6 °C (DMSO-d6).1H NMR (DMSO-d6, δ ppm): 9.55 (s, 1H, ArOH), 7.15 (d, 2H, ArH), 6.80 (d, 2H, ArH), 3.84 (s, 2H , CH2).13C NMR (DMSO-d6, δ ppm): 156.99, 129.40, 121.21, 119.80, 115.85, 21.73. IR (KBr, cm-1): 3340.71, 2268.29, 1614.42, 1516.05, 1446.61, 1408.04, 1263.37, 1222.37, 1222.04. 1263.37, 1222.87, 1105.21, 943.19, 819.75, 759.95, 707.88, 578.64. GC-MS (m/z): 133 (base peak), 106, 90, 78.

References

[1] Patent: WO2009/84037, 2009, A2. Location in patent: Page/Page column 7; 8; 18-19
[2] European Journal of Organic Chemistry, 2007, # 21, p. 3449 - 3462
[3] Letters in Organic Chemistry, 2011, vol. 8, # 1, p. 48 - 52
[4] Journal of Chemical Research, 2004, # 10, p. 693 - 694
[5] Journal fuer Praktische Chemie (Leipzig), 1987, vol. 329, # 6, p. 963 - 974

4-Hydroxybenzyl cyanide(14191-95-8)Related Product Information

• 4-Hydroxy-D-(-)-2-phenylglycine
• 4-Hydroxybenzoic acid
• 4'-Hydroxyacetophenone
• 4-Methoxybenzyl cyanide
• 4-Hydroxybenzaldehyde
• Tyramine
• Diphenylacetonitrile
• 4-Hydroxyphenylacetic acid
• Methylparaben
• p-(2-Methoxyethyl) phenol
• 4-Methoxyphenol
• Copper(I) Cyanide
• 2-(4-HYDROXYPHENYL)ACETALDEHYDE
• 3-(4-Hydroxyphenyl)propionic acid
• 4-Hydroxybenzyl alcohol
• 4-Hydroxyphenethyl alcohol
• 4-Hydroxyphenylacetamide
• Benzeneacetonitrile