4-HYDROXYBENZYLIDENEMALONONITRILE

Base Information

• Chemical Name: 4-HYDROXYBENZYLIDENEMALONONITRILE
• CAS No.: 3785-90-8
• Molecular Formula: C10H6N2O
• Molecular Weight: 170.17
• Hs Code.: 2926909090
• European Community (EC) Number: 223-253-0
• NSC Number: 1345
• UNII: UKI2IW0CAY
• DSSTox Substance ID: DTXSID80191283
• Nikkaji Number: J147.636J
• Wikidata: Q27185965
• Pharos Ligand ID: LYL7L4MW1AP3
• ChEMBL ID: CHEMBL305695
• Mol file: 3785-90-8.mol

Synonyms:Malononitrile,(p-hydroxybenzylidene)- (7CI,8CI);Propanedinitrile,[(4-hydroxyphenyl)methylene]- (9CI);2-(4-Hydroxybenzylidene)malononitrile;2-[(4-Hydroxyphenyl)methylene]malononitrile;4-Hydroxybenzylidenemalononitrile;NSC 1345;Tyrphostin 8;Tyrphostin A 8;Tyrphostin AG 10;[(4-Hydroxyphenyl)methylene]propanedinitrile;p-Hydroxybenzylidenemalononitrile;

Chemical Property of 4-HYDROXYBENZYLIDENEMALONONITRILE

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 1.66E-05mmHg at 25°C
• Melting Point: 186-189 °C
• Refractive Index: 1.653
• Boiling Point: 354.3 °C at 760 mmHg
• PKA: 7.37±0.13(Predicted)
• Flash Point: 168.1 °C
• PSA: 67.81000
• Density: 1.29 g/cm³
• LogP: 1.82276
• Storage Temp.: 2-8°C
• Solubility.: ethanol: 20 mg/mL, clear
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 170.048012819
• Heavy Atom Count: 13
• Complexity: 275

Purity/Quality:

99% ^*data from raw suppliers

2-Hydroxybenzalmalononitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=C(C#N)C#N)O
• Uses: Inhibitor of transducin GTPase activity

Technology Process of 4-HYDROXYBENZYLIDENEMALONONITRILE

There total 11 articles about 4-HYDROXYBENZYLIDENEMALONONITRILE 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: 100.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + malononitrile (109-77-3) → 2-(4-hydroxyphenylmethylene)malononitrile (3785-90-8)

Guidance literature:

at 150 ℃; for 1h;

DOI:10.1016/S0040-4020(03)00554-4

Reference yield: 86.0%

4-(dimethoxymethyl)phenol (59276-27-6) + malononitrile (109-77-3) → 2-(4-hydroxyphenylmethylene)malononitrile (3785-90-8)

Guidance literature:

With water; In toluene; at 90 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c8nj01934g

Reference yield: 78.0%

(4-hydroxyphenyl)methanol (623-05-2) + malononitrile (109-77-3) → 2-(4-hydroxyphenylmethylene)malononitrile (3785-90-8)

Guidance literature:

With tert.-butylhydroperoxide; In acetonitrile; at 50 ℃; for 13h;

DOI:10.1039/d1ra06509b

upstream raw materials:

4-hydroxy-benzaldehyde

malononitrile

phenoxymethylene-malononitrile

α-naphthol

Downstream raw materials:

3-Amino-1-(4-hydroxy-phenyl)-1H-4-oxa-5-aza-phenanthrene-2-carbonitrile

2-amino-4-(4-hydroxyphenyl)-4H-benzo[f]chromene-3-carbonitrile

2-amino-7-hydroxy-4-(4-hydroxyphenyl)-4H-chromene-3-carbonitrile

2-amino-4-(4-hydroxyphenyl)-5-oxo-4H,5H-dihydropyrano[3,2-c]chromene-3-carbonitrile

Refernces

• 1、 Jlassi, Raja,Ribeiro, Ana P.C.,Tiago, Gon?alo A.O.,Wang, Jiawei,Krawczyk, Marta S.,Martins,Na?li, Houcine,Pombeiro, Armando J.L.,Rekik, Walid. "Elementary and efficient catalyst process for the Knoevenagel condensation of araldehydes with arylmethylidene malononitrile". . p. 76 - 81. Retrieved 2018.
• 2、 Hassanzadeh, Fariba,Shirini, Farhad,Mamaghani, Manouchehr,Daneshvar, Nader. "Introduction of succinimide as a green and sustainable organo-catalyst for the synthesis of arylidene malononitrile and tetrahydrobenzo[b] pyran derivatives". . p. 155 - 163. Retrieved 2021/03/23.
• 3、 Gupta, Padmini,Kumar, Lalita S.,Kumar, Yogesh,Shabir, Javaid. "Design and Development of Amine Functionalized Mesoporous Cubic Silica Particles: A Recyclable Catalyst for Knoevenagel Condensation". . . Retrieved 2021/07/28.