4-Chlorotoluene

Base Information

• Chemical Name: 4-Chlorotoluene
• CAS No.: 106-43-4
• Molecular Formula: C7H7Cl
• Molecular Weight: 126.586
• Hs Code.: 29337900
• European Community (EC) Number: 203-397-0
• ICSC Number: 1386
• NSC Number: 404114
• UN Number: 2238
• UNII: Q8R236H42N
• DSSTox Substance ID: DTXSID8024814
• Nikkaji Number: J3.610B
• Wikidata: Q22328364
• ChEMBL ID: CHEMBL1797268
• Mol file: 106-43-4.mol

Synonyms:4-chlorotoluene;4-chlorotoluene, 38Cl-labeled;4-chlorotoluene, ion(1+);p-chlorotoluene;para-chlorotoluene

Chemical Property of 4-Chlorotoluene

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 3.77mmHg at 25°C
• Melting Point: 6-8 °C(lit.)
• Refractive Index: 1.519 - 1.521
• Boiling Point: 158.5 °C at 760 mmHg
• Flash Point: 46.2 °C
• PSA: 0.00000
• Density: 1.075 g/cm³
• LogP: 2.64840
• Storage Temp.: 0-6°C
• Solubility.: 0.040g/l
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 126.0236279
• Heavy Atom Count: 8
• Complexity: 62.8

Purity/Quality:

≥99% ^*data from raw suppliers

PCT ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,T,F
• Hazard Codes: Xn:Harmful;;
• Statements: R20:; R51/53:
• Safety Statements: S24/25:; S61:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Chlorinated Aromatics
• Canonical SMILES: CC1=CC=C(C=C1)Cl
• Effects of Short Term Exposure: If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking.
• Uses: 4-Chlorotoluene is used in a variety of organic synthesis, such as acting as coupling precursors for palladium-catalyzed acylation of acetanilides. Solvent; dyestuff intermediate; in organic syntheses. 4-chlorotoluene is an intermediate in the manufacture of fenvalerate, paclobutrazol , uniconazole, trifluralin, thiobencarb, and dymron, etc. it is also used in the manufacture of 4-chlorobenzyl chloride, 4-chlorobenzaldehyde, 4-chlorobenzoic acid, etc.

Technology Process of 4-Chlorotoluene

There total 245 articles about 4-Chlorotoluene 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: 47.0%

carbon monoxide (201230-82-2) + tributyl(p-tolyl)stannane (31614-66-1) → bis(p-methylphenyl)-methanone (611-97-2) + (4,4'-dimethyl-1,1'-biphenyl) (613-33-2) + para-chlorotoluene (106-43-4) + p-Toluic acid (99-94-5)

Guidance literature:

With copper dichloride; palladium dichloride; In acetic acid; at 25 ℃; for 20h;

DOI:10.1246/bcsj.74.1343

Reference yield: 41.0%

p-toluenesulfonyl chloride (98-59-9) → (4,4'-dimethyl-1,1'-biphenyl) (613-33-2) + para-chlorotoluene (106-43-4)

Guidance literature:

With palladium diacetate; lithium carbonate; copper(l) chloride; In 1,4-dioxane; at 120 ℃; for 21h; Reagent/catalyst; Inert atmosphere;

DOI:10.1039/d0sc05192f

Reference yield: 14.0%

toluene (108-88-3,15644-74-3,16713-13-6) → para-chlorotoluene (106-43-4) + 2-methylchlorobenzene (95-49-8) + benzyl chloride (100-44-7)

Guidance literature:

With iron(III)porphyrinate; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1002/hlca.19980810554

upstream raw materials:

phosgene

diethyl ether

1-chloro-4-{[(phenylmethyl)oxy]methyl}benzene

isopropylmagnesium bromide

Downstream raw materials:

N-<(4-Methylphenyl)sulfonyl>-4-methylbenzenecarboxamide

2,2,2-trichloro-1-(2-chloro-5-methyl-phenyl)-ethanol

1,1,1-trichloro-2,2-bis-(5-chloro-2-methyl-phenyl)-ethane

methyl 2-(4-methylbenzamido)benzoate

Refernces

• 1、 Bost,Baker. "-". . p. 1112. Retrieved 1933.
• 2、 Chang, Chen-Chang,Burger, Mathew J.,Faitar, Gheorghita M.,Lund, Carl R. F.. "Zeolite-catalyzed chlorination of toluene by sulfuryl chloride: Activity, selectivity, and deactivation of ZSM-5". . p. 59 - 67. Retrieved 2001.
• 3、 Okazaki, Susumu,Jouhouji, Hirofumi. "Vapor-Phase Isomerization of o-Chlorotoluene over H-Mordenite Treated with CF3Cl". . p. 1931 - 1936. Retrieved 1986.
• 4、 Verma, Sanny,Saran, Sandeep,Jain, Suman L.. "Glycinatocopper(II) complex as an efficient heterogeneous catalyst for aromatic Finkelstein reaction of aryl and heteroaryl bromides to chlorides". . p. 178 - 183. Retrieved 2014.
• 5、 Hubbard, Abigail,Okazaki, Takao,Laali, Kenneth K.. "Chlorination of aromatics with trichloroisocyanuric acid (TCICA) in bronsted-acidic imidazolium ionic liquid [BMIM(SO3H)][OTf]: An economical, green protocol for the synthesis of chloroarenes". . p. 923 - 927. Retrieved 2007.
• 6、 Wright, Luka A.,Hope, Eric G.,Solan, Gregory A.,Cross, Warren B.,Singh, Kuldip. "O,N,N-Pincer ligand effects on oxidatively induced carbon-chlorine coupling reactions at palladium". . p. 6040 - 6051. Retrieved 2015.
• 7、 Ben-Daniel, Revital,De Visser, Samuel P.,Shaik, Sason,Neumann, Ronny. "Electrophilic aromatic chlorination and haloperoxidation of chloride catalyzed by polyfluorinated alcohols: A new manifestation of template catalysis". . p. 12116 - 12117. Retrieved 2003.
• 8、 Juenge et al.. "-". . p. 719. Retrieved 1970.
• 9、 Nwaukwa, Stephen O.,Keehn, Philip M.. "THE OXIDATION OF ALDEHYDES TO ACIDS WITH CALCIUM HYPOCHLORITE ". . p. 3131 - 3134. Retrieved 1982.
• 10、 Mendon?a, Gabriela F.,Bastos, Alexander R.,Boltz, Marilyne,Louis, Beno?t,Pale, Patrick,Esteves, Pierre M.,De Mattos, Marcio C.S.. "Electrophilic chlorination of arenes with trichloroisocyanuric acid over acid zeolites". . p. 46 - 51. Retrieved 2013.