19692-45-6

Basic information

• Product Name: 4-tert-Butylbenzyl chloride
• Synonyms: Benzene,1-(chloromethyl)-4-(1,1-dimethylethyl)-;Benzene,1-(chloromethyl)-4-dimethylethyl)-;p-tert-Butyl-alpha-chlorotoluene;1-chloromethyl-4-tert-butylbenzene;4-tert-Butylbenzyl chloride 97%;4-Chloromethyl-t-butylbenzene;1-Chloromethyl-4-tert-butylbenzene, 4-(tert-Butyl)-α-chlorotoluene;4-(tert-Butyl)benzylchloride,97%
• CAS NO: 19692-45-6
• Molecular Formula: C₁₁H₁₅Cl
• Molecular Weight: 182.69
• EINECS: 243-228-8
• Mol File: 19692-45-6.mol
• Article Data: 34

Chemical Properties

• Melting Point: -18 °C
• Boiling Point: 101-105 °C7 mm Hg(lit.)
• Flash Point: 202 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.945 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0594mmHg at 25°C
• Refractive Index: n20/D 1.521(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Slightly soluble in water.
• BRN: 471673
• CAS DataBase Reference: 4-tert-Butylbenzyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-tert-Butylbenzyl chloride(19692-45-6)
• EPA Substance Registry System: 4-tert-Butylbenzyl chloride(19692-45-6)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 19692-45-6(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

4-tert-Butylbenzyl chloride has been used to control molecular weight and prevent microgel formation during polymerization reaction.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 1933, 1983 DOI: 10.1016/S0040-4039(00)81809-2

InChI:InChI=1/C11H15Cl/c1-11(2,3)10-6-4-9(8-12)5-7-10/h4-7H,8H2,1-3H3

Upstream product

• 50-00-0 formaldehyd 
• 253185-03-4 tert-butylbenzene 
• 107-30-2 chloromethyl methyl ether 
• 26537-19-9 methyl 4-tert-butylbenzoate 
• 38870-89-2 Methoxyacetyl chloride 
• 877-65-6 p-tert-butylbenzyl alcohol 
• 64321-35-3 4-(1,1-Dimethylethyl)phenylmethyl ketone 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 7791-25-5 sulfuryl dichloride 
• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 98-51-1 4-tert-butyltoluene 
• 71-43-2 benzene 
• 939-97-9 4-tert-Butylbenzaldehyde 
• 98-88-4 benzoyl chloride 

Downstream Products

• 94434-95-4 2-{4-[2-(4-tert-butyl-benzyloxy)-ethyl]-piperazin-1-yl}-ethanol 
• 3288-99-1 4-tert-butylbenzyl cyanide 
• 98-51-1 4-tert-butyltoluene 
• 34252-92-1 4-tert-butyl-2-nitrobenzyl chloride 
• 32857-63-9 4-t-butylphenylacetic acid 
• 103797-19-9 4-(tert-butyl)-2-nitrobenzoic acid 
• 81066-61-7 3-(4-tert-butyl-benzyloxy)-pyridin-2-ylamine 
• 60449-44-7 7-(p-tert.butylbenzyl)-8-quinolinol 
• 116762-17-5 1-(4-tert-butyl-phenyl)-3,3-dimethyl-butan-2-one 
• 116762-18-6 2-(4-tert-Butyl-benzyl)-1-(4-tert-butyl-phenyl)-3,3-dimethyl-butan-2-ol 
• 116762-15-3 1-(4-tertiobutyl)phenyl-2,3,3-trimethyl-2-butanol 
• 116762-14-2 1-(4-tertiobutylphenyl)-2-octanol 
• 72138-48-8 3,3-Dimethyl-4-(4-tert-butylphenyl)-1-butyne 
• 72138-34-2 2-(p-tert-Butylphenyl)-3,3-dimethylmethylenecyclopropane 

Relevant articles and documents

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Discovery of Novel Azetidine Amides as Potent Small-Molecule STAT3 Inhibitors

We optimized our previously reported proline-based STAT3 inhibitors into an exciting new series of (R)-azetidine-2-carboxamide analogues that have sub-micromolar potencies. 5a, 5o, and 8i have STAT3-inhibitory potencies (IC50) of 0.55, 0.38, and 0.34 μM, respectively, compared to potencies greater than 18 μM against STAT1 or STAT5 activity. Further modifications derived analogues, including 7e, 7f, 7g, and 9k, that addressed cell membrane permeability and other physicochemical issues. Isothermal titration calorimetry analysis confirmed high-affinity binding to STAT3, with KD of 880 nM (7g) and 960 nM (9k). 7g and 9k inhibited constitutive STAT3 phosphorylation and DNA-binding activity in human breast cancer, MDA-MB-231 or MDA-MB-468 cells. Furthermore, treatment of breast cancer cells with 7e, 7f, 7g, or 9k inhibited viable cells, with an EC50 of 0.9-1.9 μM, cell growth, and colony survival, and induced apoptosis while having relatively weaker effects on normal breast epithelial, MCF-10A or breast cancer, MCF-7 cells that do not harbor constitutively active STAT3.

Lewis Base Catalysis Enables the Activation of Alcohols by means of Chloroformates as Phosgene Substitutes

Nucleophilic substitutions (SN) are typically promoted by acid chlorides as sacrificial reagents to improve the thermodynamic driving force and lower kinetic barriers. However, the cheapest acid chloride phosgene (COCl2) is a highly toxic gas. Against this background, phenyl chloroformate (PCF) was discovered as inherently safer phosgene substitute for the SN-type formation of C?Cl and C?Br bonds using alcohols. Thereby, application of the Lewis bases 1-formylpyrroldine (FPyr) and diethylcyclopropenone (DEC) as catalysts turned out to be pivotal to shift the chemoselectivity in favor of halo alkane generation. Primary, secondary and tertiary, benzylic, allylic and aliphatic alcohols are appropriate starting materials. A variety of functional groups are tolerated, which includes even acid labile moieties such as tert-butyl esters and acetals. Since the by-product phenol can be isolated, a recycling to PCF with inexpensive phosgene would be feasible on a technical scale. Eventually, a thorough competitive study demonstrated that PCF is indeed superior to phosgene and other substitutes.