4,4'-di-tert-Butylbiphenyl

Base Information

• Chemical Name: 4,4'-di-tert-Butylbiphenyl
• CAS No.: 1625-91-8
• Molecular Formula: C20H26
• Molecular Weight: 266.426
• Hs Code.: 29029090
• European Community (EC) Number: 216-615-4
• DSSTox Substance ID: DTXSID4048193
• Nikkaji Number: J80.265D
• Wikidata: Q72469990
• ChEMBL ID: CHEMBL3187007
• Mol file: 1625-91-8.mol

Synonyms:4,4'-di-tert-butylbiphenyl;DBB biphenyl cpd;DTBB cpd

Chemical Property of 4,4'-di-tert-Butylbiphenyl

Chemical Property:

• Appearance/Colour: WHITE POWDER, CRYSTALS, CRYSTALLINE POWDER AND/OR CHUNKS
• Melting Point: 126-130 °C(lit.)
• Refractive Index: 1.5928 (estimate)
• Boiling Point: 337.8 °C at 760 mmHg
• Flash Point: 173.9 °C
• PSA: 0.00000
• Density: 0.924 g/cm³
• LogP: 5.94860
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: dioxane: 0.1 g/mL, clear
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 266.203450829
• Heavy Atom Count: 20
• Complexity: 253

Purity/Quality:

98% ^*data from raw suppliers

4,4''-Di-tert-butylbiphenyl ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)C2=CC=C(C=C2)C(C)(C)C
• Uses: It is used in the generation of 1,2-di(lithiomethyl)benzene. It is found to accept electrons from Li metal to give a radical anion which is highly effective in the conversion of alkyl halides to alkyllithiums. 4,4?-Di-tert-butylbiphenyl is used in production of homoallylic amine derivatives. It is also used in the preparation of lithium di-tert-butylbiphenylide, a radical anion, superior to sodium or lithium naphthalenides for metalation reactions. Along with lithium, 4,4?-Di-tert-butylbiphenyl catalyzes; reaction of chloromethyl ethyl ether and different carbonyl compounds to yield corresponding hydroxyethers and reductive opening of N-phenylazetidine.

Technology Process of 4,4'-di-tert-Butylbiphenyl

There total 92 articles about 4,4'-di-tert-Butylbiphenyl 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%

biphenyl (92-52-4,1594-86-1) + tertiary butyl chloride (507-20-0) → 4,4'-di-tert-butylbiphenyl (1625-91-8)

Guidance literature:

iron(III) chloride; In dichloromethane; at 20 ℃;

Reference yield: 99.0%

1-bromo-4-tert-butylbenzene (3972-65-4) → 4,4'-di-tert-butylbiphenyl (1625-91-8)

Guidance literature:

With tetraethylammonium tosylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; Ambient temperature; electrolysis;

DOI:10.1016/S0040-4039(00)98576-9

Reference yield: 99.0%

4-(tert-butyl)chlorobenzene (3972-56-3) → 4,4'-di-tert-butylbiphenyl (1625-91-8)

Guidance literature:

With 4-(3'-butyl-1'-imidazolio)-1-butanesulfonic acid hydrogen sulfate; aluminium; In carbon dioxide; at 45 ℃; for 8h; under 116262 Torr; Supercritical conditions;

DOI:10.1002/adsc.201000475

upstream raw materials:

biphenyl

2-methyl-propan-1-ol

1-tert-butyl-4-iodobenzene

tert-butylbenzene

Downstream raw materials:

2,7-di-tert-butylfluorenone

2,7-dibromo-(2',7'-di-tert-butyl)-9,9'-spirobifluorene

3,7-di-tert-butyl-5-phenylbenzo[b]phosphindole 5-oxide

4,4′-di-tert-butyl-N,N′-bis(3,5-di-tert-butyl-2-hydroxyphenyl)-2,2′-diaminobiphenyl

Refernces

• 1、 Levitskiy, Oleg A.,Sentyurin, Vyacheslav V.,Bogdanov, Alexey V.,Magdesieva, Tatiana V.. "Synthesis of unsymmetrical N-(2-tert-butylphenyl)-N-(4-tert-butylphenyl)nitroxyl radical, the first stable diarylnitroxyl with vacant para-position". . p. 535 - 537. Retrieved 2016.
• 2、 Shibata, Mari,Ito, Hideto,Itami, Kenichiro. "Oxidative homocoupling reaction of aryltrimethylsilanes by Pd/o-chloranil catalysis". . p. 1701 - 1704. Retrieved 2017.
• 3、 Rocchigiani, Luca,Klooster, Wim T.,Coles, Simon J.,Hughes, David L.,Hrobárik, Peter,Bochmann, Manfred. "Hydride Transfer to Gold: Yes or No? Exploring the Unexpected Versatility of Au???H?M Bonding in Heterobimetallic Dihydrides". . p. 8267 - 8280. Retrieved 2020.
• 4、 Cao, Ya-Nan,Tian, Xin-Chuan,Chen, Xing-Xiu,Yao, Yun-Xin,Gao, Feng,Zhou, Xian-Li. "Rapid Ligand-Free Base-Accelerated Copper-Catalyzed Homocoupling Reaction of Arylboronic Acids". . p. 601 - 606. Retrieved 2017.
• 5、 He, Tao,Huang, Zhehao,Yuan, Shuai,Lv, Xiu-Liang,Kong, Xiang-Jing,Zou, Xiaodong,Zhou, Hong-Cai,Li, Jian-Rong. "Kinetically Controlled Reticular Assembly of a Chemically Stable Mesoporous Ni(II)-Pyrazolate Metal-Organic Framework". . p. 13491 - 13499. Retrieved 2020.
• 6、 de la Mare,P.B.D.,Johnson,E.A.. "-". . p. 4076 - 4084. Retrieved 1963.
• 7、 Finnegan,Matson. "". . p. 4780. Retrieved 1972.
• 8、 Rathore, Rajendra,Burns, Carrie L.. "A practical one-pot synthesis of soluble hexa-peri-hexabenzocoronene and isolation of its cation-radical salt". . p. 4071 - 4074. Retrieved 2003.
• 9、 Moon, Jeongju,Nam, Hyungoog,Ju, Jinhun,Jeong, Miso,Lee, Sunwoo. "Homocoupling of aryl halides using catalytic system of palladium and phosphite". . p. 1432 - 1433. Retrieved 2007.
• 10、 Hollas, Aaron M.,Ziller, Joseph W.,Heyduk, Alan F.. "Three oxidation states of the bis(3,5-di-tert-butyl-2-phenolato)azanido pincer ligand on chromium(III)". . p. 111 - 117. Retrieved 2018.