(3-Methoxyphenyl)acetonitrile

Base Information

• Chemical Name: (3-Methoxyphenyl)acetonitrile
• CAS No.: 19924-43-7
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Hs Code.: 29269095
• European Community (EC) Number: 243-428-5
• NSC Number: 143401
• DSSTox Substance ID: DTXSID60173704
• Nikkaji Number: J62.876J
• Mol file: 19924-43-7.mol

Synonyms:19924-43-7;(3-Methoxyphenyl)acetonitrile;2-(3-methoxyphenyl)acetonitrile;3-Methoxyphenylacetonitrile;3-Methoxybenzyl cyanide;(m-Methoxyphenyl)acetonitrile;Benzeneacetonitrile, 3-methoxy-;MFCD00001910;3-methoxybenzeneacetonitrile;3-methoxyphenyl acetonitrile;M-METHOXYBENZYL CYANIDE;EINECS 243-428-5;NSC143401;m-methoxybenzylcyanide;m-Methoxy benzyl cyanide;m-methoxyphenylacetonitrile;3-methoxyphenyl-acetonitrile;(3 methoxyphenyl)acetonitrile;3-methoxy-phenyl-acetonitrile;SCHEMBL101334;(3-methoxyphenyl)-acetonitrile;DTXSID60173704;[3-(methyloxy)phenyl]acetonitrile;3-Methoxyphenylacetonitrile, 99%;CHEBI:194899;STR03186;STL168046;AKOS000158848;AM82829;CS-W007963;NSC 143401;NSC-143401;PB48453;PS-4176;AC-23559;SY013554;FT-0616011;M2331;EN300-41178;W-107659;Z285184582

Chemical Property of (3-Methoxyphenyl)acetonitrile

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.00264mmHg at 25°C
• Melting Point: 8oC
• Refractive Index: n20/D 1.5402(lit.)
• Boiling Point: 286.4 °C at 760 mmHg
• Flash Point: 98.9 °C
• PSA: 33.02000
• Density: 1.053 g/cm³
• LogP: 1.76128
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol
• Water Solubility.: INSOLUBLE
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

99.9% ^*data from raw suppliers

3-Methoxyphenylacetonitrile ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=CC(=C1)CC#N
• Uses: 3-Methoxyphenylacetonitrile is used in the synthesis of isoflavones which inhibit epithelial cell proliferation and induce apoptosis in vitro. 3-Methoxyphenylacetonitrile was used in the synthesis of:new immunogen for homovanillic acidβ,β′-cyclobisalkylated melatoninergic phenylalkylamidesα-sec-butyl-3-methoxy phenylacetonitrile, antispasmodic agent

Technology Process of (3-Methoxyphenyl)acetonitrile

There total 32 articles about (3-Methoxyphenyl)acetonitrile 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: 98.0%

3-methoxyphenylboronic acid (10365-98-7,1107579-37-2) + 2-aminoacetonitrile hydrochloride (6011-14-9) → 3-methoxyphenylacetonitrile (19924-43-7)

Guidance literature:

With sodium nitrite; In water; toluene; at 50 ℃; for 24h; Schlenk technique;

DOI:10.1002/anie.201406765

Reference yield: 97.0%

1-chloro-3-methoxy-benzene (2845-89-8) + sodium cyanoacetate (1071-36-9) → 3-methoxyphenylacetonitrile (19924-43-7)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(η3-allyl-μ-chloropalladium(II)); In 1,3,5-trimethyl-benzene; at 20 - 140 ℃; for 5.16667h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201006763

Reference yield: 92.5%

potassium cyanide + m-methoxybenzyl chloride (824-98-6) → 3-methoxyphenylacetonitrile (19924-43-7)

Guidance literature:

In water; at 70 - 85 ℃; for 4h; Temperature;

upstream raw materials:

acetic anhydride

potassium cyanide

m-methoxybenzyl chloride

1-bromomethyl-3-methoxybenzene

Downstream raw materials:

(3-methoxy-phenyl)-thiazol-2-yl-acetonitrile

3-cyano-1-(dimethylamino)-3-(m-methoxyphenyl)propane

2-(3'-Methoxyphenyl)-2-methylpropionitrile

1-(3-Methoxyphenyl)cyclopentanecarbonitrile

Refernces

• 1、 -. "Preparation method of m-methoxyphenethylamine". Paragraph 0017; 0049-0052; 0055-0058; 0061-0064. . Retrieved 2021/11/14.
• 2、 Huang, Yubing,Yu, Yue,Zhu, Zhongzhi,Zhu, Chuanle,Cen, Jinghe,Li, Xianwei,Wu, Wanqing,Jiang, Huanfeng. "Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source". . p. 7621 - 7627. Retrieved 2017/07/26.