4-(2-Hydroxyethyl)benzonitrile

Base Information

• Chemical Name: 4-(2-Hydroxyethyl)benzonitrile
• CAS No.: 69395-13-7
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 2926909090
• European Community (EC) Number: 677-864-6
• DSSTox Substance ID: DTXSID00384190
• Nikkaji Number: J410.690C
• Wikidata: Q72458809
• ChEMBL ID: CHEMBL4534422
• Mol file: 69395-13-7.mol

Synonyms:4-(2-hydroxyethyl)benzonitrile;69395-13-7;2-(4-CYANOPHENYL)ETHANOL;MFCD00052461;BENZONITRILE, 4-(2-HYDROXYETHYL)-;4-Cyanobenzeneethanol;p-cyanophenethylalcohol;2-(4-CYANOPHENYL)ETHAN-1-ONE;p-cyanophenethyl alcohol;4-cyanophenethyl alcohol;4-(2Hydroxyethyl)benzonitrile;SCHEMBL320278;CHEMBL4534422;DTXSID00384190;CHEBI:194819;RBSJBNYPTGMZIH-UHFFFAOYSA-N;4-(2-hydroxy-ethyl)-benzonitrile;Benzonitrile,4-(2-hydroxyethyl)-;AMY36572;BBL102762;STL556568;AKOS006229243;CS-W018212;SY100982;TS-01919;4-(2-hydroxyethyl)benzonitrile, AldrichCPR;A9176;BB 0305893;FT-0616540;EN300-61341;Z964982550;JMD

Chemical Property of 4-(2-Hydroxyethyl)benzonitrile

Chemical Property:

• Appearance/Colour: pale yellow solid.
• Vapor Pressure: 0.000507mmHg at 25°C
• Melting Point: 50-51 °C
• Refractive Index: 1.559
• Boiling Point: 300.2 °C at 760 mmHg
• PKA: 14.72±0.10(Predicted)
• Flash Point: 135.3 °C
• PSA: 44.02000
• Density: 1.12 g/cm³
• LogP: 1.09308
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 150

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(2-Hydroxyethyl)benzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCO)C#N
• Uses: 4-(2-Hydroxyethyl)benzonitrile is used to produce 4-(2-bromo-ethyl)-benzonitrile. It is used as organic intermediate.

Technology Process of 4-(2-Hydroxyethyl)benzonitrile

There total 14 articles about 4-(2-Hydroxyethyl)benzonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

methyl 4-cyanobenzeneacetate (52798-01-3) → 4-(2-hydroxyethyl)benzonitrile (69395-13-7)

Guidance literature:

methyl 4-cyanobenzeneacetate; With sodium triethylborohydride; In diethyl ether; toluene; at 20 ℃; for 8h; Inert atmosphere;

With sodium hydroxide; In methanol; diethyl ether; toluene; at 20 ℃; for 2h; Reagent/catalyst; Solvent; Time;

DOI:10.1002/chem.201502942

Reference yield: 38.0%

4-cyano-benzenesulfonic acid 2-bromo-ethyl ester → 4-(2-hydroxyethyl)benzonitrile (69395-13-7) + 4-cyano-benzenesulfonic acid ethyl ester + 1,1-dioxo-3,4-dihydro-1H-1λ6-benzo[c][1,2]oxathiine-6-carbonitrile

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 12h; Heating;

DOI:10.1039/b303728b

Reference yield:

4-oxiran-2-ylbenzonitrile (52695-39-3) → 4-(1-hydroxyethyl)benzonitrile (101219-69-6,101219-71-0,134679-06-4,52067-35-3) + 4-(2-hydroxyethyl)benzonitrile (69395-13-7)

Guidance literature:

With trimethylamine-N-oxide; [bis(hexamethylene)cyclopentadienone]iron tricarbonyl; hydrogen; In toluene; at 150 ℃; for 22h; under 37503.8 Torr; Overall yield = 28 percentSpectr.;

DOI:10.1021/acscatal.1c03549

upstream raw materials:

sodium cyanide

2-(4'-aminophenyl)ethyl alcohol

copper(I) cyanide

4-cyanobenzenesulfonic acid

Downstream raw materials:

4-[2-(1,3-dioxoisoindolin-2-yl)ethyl]benzonitrile

1-[3-bromo-4-(2-fluoroethyl)phenyl]methanamine

1-[3-bromo-4-(2-fluoroethyl)benzyl]guanidine trfluoroacetic acid salt

tert-butyl [(Z)-[(tert-butoxycarbonyl)amino] {[3-bromo-4-(2-hydroxyethyl)benzyl]amino}methylidene]carbamate

Refernces

• 1、 Huang, Cheng,Lu, Qingquan,Ma, Wan,Qi, Xiaotian,Xu, Minghao,Zheng, Xuelian. "Epoxide Electroreduction". . p. 1389 - 1395. Retrieved 2022/01/19.
• 2、 Xie, Jin,Yang, Fengzhi,Zhang, Man,Lam, Celine,Qiao, Yixue,Xiao, Jia,Zhang, Dongdong,Ge, Yuxuan,Fu, Lei,Xie, Dongsheng. "Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety". supporting information. p. 131 - 134. Retrieved 2016/12/27.