4-(HYDROXYMETHYL)BENZONITRILE Chemical Properties

Melting point:

39-43 °C(lit.)

Boiling point:

203 °C(Press: 53 Torr)

Density 

1.16±0.1 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

pka

13.99±0.10(Predicted)

Appearance

White to light yellow Solid

Water Solubility 

Insoluble in water.

BRN 

2206193

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

RIDADR 

3439

WGK Germany 

3

F 

10

HazardClass 

6.1

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich

4-(HYDROXYMETHYL)BENZONITRILE Usage And Synthesis

Uses

4-(Hydroxymethyl)benzonitrile [p-(hydroxymethyl)benzonitrile] may be used to synthesize p-((vinyloxy)methyl)benzonitrile (VOMBN).

Definition

ChEBI: 4-cyanobenzyl alcohol is an aromatic primary alcohol. It is functionally related to a benzyl alcohol.

General Description

4-(Hydroxymethyl)benzonitrile can be synthesized via hydrosilylation reaction in the presence of Fe complex Bu₄N[Fe(CO)₃(NO)] [catalyst]. It can also be prepared from 4-(aminomethyl) benzyl alcohol.

Synthesis

8A. Synthesis of 4-hydroxymethylbenzonitrile: Boron trifluoride diethyl ether compound (0.85 mL, 6.8 mmol) was slowly added to a solution containing 4-cyanobenzoic acid (1.0 g, 6.8 mmol) and tetrahydrofuran (10 mL). Borane-tetrahydrofuran complex (1.0 M, 13.6 mL) was added dropwise to the reaction mixture at room temperature, during which no significant exothermic phenomenon was observed. The reaction mixture was stirred continuously for 2 h at room temperature and then concentrated under vacuum. The obtained residue was dissolved in ethyl acetate (50 mL), washed sequentially with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated in vacuum to afford the target product 4-hydroxymethylbenzonitrile (0.900 g, 95% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ 4.65 (s, 2H), 7.38 (d 2H), 7.53 (d, 2H).

References

[1] Patent: US2007/270438, 2007, A1. Location in patent: Page/Page column 39
[2] Tetrahedron Letters, 2003, vol. 44, # 16, p. 3427 - 3428
[3] Advanced Synthesis and Catalysis, 2014, vol. 356, # 2-3, p. 308 - 312
[4] Dalton Transactions, 2016, vol. 45, # 19, p. 8265 - 8271

4-(HYDROXYMETHYL)BENZONITRILE(874-89-5)Related Product Information

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• 4-oxiran-2-ylbenzonitrile