| Identification | Back Directory | [Name]
4-(HYDROXYMETHYL)BENZONITRILE | [CAS]
874-89-5 | [Synonyms]
4-CYANOBENZYL ALCOHOL
4-cyanobeznyl alcohol
4-methylolbenzonitrile
4-Cyanobenzenemethanol
Tranexamic Acid Impurity 13
4-(HYDROXYMETHYL)BENZONITRILE
Benzonitrile,4-(hydroxyMethyl)-
4-(Hydroxymethyl)benzonitrile 95%
4-(hydroxymethyl)benzenecarbonitrile
4-(HydroxyMethyl)benzonitrile, puruM, >=97.0% (GC) | [Molecular Formula]
C8H7NO | [MDL Number]
MFCD00870633 | [MOL File]
874-89-5.mol | [Molecular Weight]
133.15 |
| Chemical Properties | Back Directory | [Melting point ]
39-43 °C(lit.)
| [Boiling point ]
203 °C(Press: 53 Torr) | [density ]
1.16±0.1 g/cm3(Predicted) | [Fp ]
>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 | [InChI]
1S/C8H7NO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,10H,6H2 | [InChIKey]
XAASLEJRGFPHEV-UHFFFAOYSA-N | [SMILES]
OCc1ccc(cc1)C#N |
| Safety Data | Back Directory | [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 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 |
|
|