3753-18-2

Basic information

• Product Name: 4,4'-Bis(methoxymethyl)-1,1'-biphenyl
• Synonyms: 4,4’-Dis(methoxy-methyl)-1,1’-biphenyl;4,4'-BIS(METHOXYMETHYL)-1,1'-BIPHENYL;4,4'-BIS(METHOXYMETHYL)BIPHENYL;4,4-BIS-(METHOXY-MEHTYL) BIPHENYL;,4'-Bis(methoxymethyl)-1,1-biphenyl;4,4'-Bis(methoxymethyl)-1,1'-biphenyl;4,4'-Di(methoxymethyl)diphenyl;4,4'-Bis(methoxymethyl)-1,1'-biphenyl)biphenyl
• CAS NO: 3753-18-2
• Molecular Formula: C₁₆H₁₈O₂
• Molecular Weight: 242.31
• Product Categories: Biphenyl derivatives;Biphenyl & Diphenyl ether
• Mol File: 3753-18-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 49-50°C
• Boiling Point: 350°C
• Flash Point: 125.4 °C
• Appearance: /
• Density: 1.039 g/cm³
• Vapor Pressure: 0Pa at 25℃
• Solubility: soluble in Toluene
• CAS DataBase Reference: 4,4'-Bis(methoxymethyl)-1,1'-biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Bis(methoxymethyl)-1,1'-biphenyl(3753-18-2)
• EPA Substance Registry System: 4,4'-Bis(methoxymethyl)-1,1'-biphenyl(3753-18-2)

Safety Data

• Hazardous Substances Data: 3753-18-2(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline

Synthetic route

biphenyl (92-52-4) + Dimethoxymethane (109-87-5) → 4-(methoxymethyl)-1,1'-biphenyl (86130-05-4) + 4,4′-bis(methoxymethyl)biphenyl (3753-18-2)

Conditions	Yield
mordenite SiO2/Al2O3 90 In cyclohexane at 120℃; for 4h; Product distribution / selectivity;

4-chlorobenzyl methyl ether (1195-44-4) → 4,4′-bis(methoxymethyl)biphenyl (3753-18-2)

Conditions	Yield
With zinc; 5-trimethylsilyl-2,2'-bipyridine; nickel dibromide In 1-methyl-pyrrolidin-2-one at 20 - 70℃; Inert atmosphere;
With zinc; nickel dibromide; 5,5’-bis(trimethylsilyl)-2,2’-bipyridine In 1-methyl-pyrrolidin-2-one at 20 - 70℃; Inert atmosphere;

diethyl 2-(cycloheptene-1-yl)-cyclobuten-1-yl phosphate + 4-(methoxymethyl)phenylzinc chloride lithium chloride → 4,4′-bis(methoxymethyl)biphenyl (3753-18-2) + 1-cycloheptenyl-2-[4-(methoxymethyl)phenyl]cyclobutene

Conditions	Yield
With aluminum (III) chloride; C36H28Cl2OP2Pd In tetrahydrofuran at 50℃; for 17h; Negishi Coupling; Overall yield = 73 %; Overall yield = 0.451 g;

4,4′-bis(methoxymethyl)biphenyl (3753-18-2) → 4,4'-diformylbiphenyl (66-98-8)

Conditions	Yield
With sodium bromate; acetic acid at 90℃; for 1.5h; Product distribution / selectivity;	93.3 %Chromat.

Upstream product

• 92-52-4 biphenyl 
• 109-87-5 Dimethoxymethane 
• 1195-44-4 4-chlorobenzyl methyl ether 

Relevant articles and documents

Novel Selective Approach to Terminally Substituted [n]Dendralenes

Dendralenes are simple alkenes with cross-conjugated double bonds that are frequently synthesized due to being potentially valuable building blocks for the synthesis of more complex structures. The synthetic approaches to dendralenes are based on the cross-coupling reactions of electrophilic and nucleophilic synthons derived from geminally substituted ethylene. Our novel methodology for the synthesis of only terminally substituted [3]- and [4]dendralenes, as well as 2,3-disubstituted buta-1,3-dienes, involves the preparation of 1,2-disubstituted cyclobutenes from readily available 2-bromocyclobutanone and the subsequent thermal ring-opening reactions.

TRANSITION METAL COMPLEX AND PROCESS FOR PRODUCING CONJUGATED AROMATIC COMPOUND WITH THE TRANSITION METAL COMPLEX

A transition metal complex obtained by contacting a bipyridine compound represented by the formula (1): wherein R1, R2 and R3 represent a C1-C10 alkyl group which may be substituted, etc., and R4 and R5 represent a hydrogen atom etc., with a compound of a transition metal belonging to Group 9, 10 or 11, and a process for producing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of said transition metal complex.

PROCESS

A process for the alkoxyalkylation of an unsubstituted aromatic substrate or a substituted aromatic substrate, said substitution being via a carbon-carbon bond, said process comprising reacting the aromatic substrate with a dialkoxyalkane in the presence of a catalyst.