| Identification | More | [Name]
4-Hydroxybenzyl cyanide | [CAS]
14191-95-8 | [Synonyms]
2-(4-HYDROXYPHENYL)ACETONITRILE
4-HYDROXYBENZYL CYANIDE
4-HYDROXYPHENYLACETONITRILE
P-HYDROXYBENZYL CYANIDE
(p-hydroxyphenyl)-acetonitril
4-hydroxy-benzeneacetonitril
4-hydroxybenzeneacetonitrile
Acetonitrile, (p-hydroxyphenyl)-
Benzeneacetonitrile, 4-hydroxy-
p-Hydroxyphenylacetonitrile
p-Hydroxybenzacetonitrile
4-HydroxybenzylCyanide98+%
4-Hydroxybenzyl
4-HYDROXY BENZYLCYARIDE
PARA-HYDROXYPHENYLACETONITRILE
4-HYDROXYPHENYLACETONITRILE 99+%
55) PARA HYDROXY BENZYL CYANIDE | [EINECS(EC#)]
238-046-0 | [Molecular Formula]
C8H7NO | [MDL Number]
MFCD00002383 | [Molecular Weight]
133.15 | [MOL File]
14191-95-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Light Brown Solid | [Melting point ]
67-70 °C (lit.) | [Boiling point ]
330 °C/756 mmHg (lit.) | [density ]
1.1475 (rough estimate) | [refractive index ]
1.5260 (estimate) | [Fp ]
178 °C
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform, DMSO, Methanol (Slightly) | [form ]
Solid | [pka]
9.63±0.13(Predicted) | [color ]
Light Brown to Beige | [Water Solubility ]
slightly soluble | [BRN ]
1934470 | [Exposure limits]
NIOSH: IDLH 25 mg/m3 | [InChI]
1S/C8H7NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5H2 | [InChIKey]
AYKYOOPFBCOXSL-UHFFFAOYSA-N | [SMILES]
Oc1ccc(CC#N)cc1 | [LogP]
0.591 (est) | [CAS DataBase Reference]
14191-95-8(CAS DataBase Reference) | [NIST Chemistry Reference]
4-Hydroxyphenylacetic acid nitrile(14191-95-8) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
3439 | [WGK Germany ]
3
| [RTECS ]
AM0530000
| [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29269095 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [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. | [storage]
Store at -20°C | [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 |
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