Home Cart Sign in  
Chemical Structure| 23145-05-3 Chemical Structure| 23145-05-3

Structure of 23145-05-3

Chemical Structure| 23145-05-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 23145-05-3 ]

CAS No. :23145-05-3
Formula : C8H5ClO
M.W : 152.58
SMILES Code : ClC1=CC=C(OC=C2)C2=C1
MDL No. :MFCD10699415
InChI Key :CPJOPFBXUHIQQL-UHFFFAOYSA-N
Pubchem ID :90013

Safety of [ 23145-05-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 23145-05-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 23145-05-3 ]

[ 23145-05-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 23145-05-3 ]
  • [ 76429-69-1 ]
References: [1] Patent: US5262430, 1993, A, .
  • 2
  • [ 23145-05-3 ]
  • [ 223576-64-5 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; Dimethyl ether at -60 - -10℃; for 1.25 h;
Stage #2: With Triisopropyl borate In hexane; Dimethyl ether at -60℃;
Stage #3: With hydrogenchloride In hexane; Dimethyl ether; water for 1 h;
5-Chlorobenzofuran was prepared by heating 4-chlorophenoxyacetaldehyde dimethylacetal in polyphosphoric acid; yield: 73percent. [0323] To a solution of 8.8 g (57.7 mmol) 5-chlorobenzofuran in 250 ml dry ether were added 7.32 g (63.0 mmol) tetramethylethylenediamine (TMEDA). The solution was kept below -60° C. under argon, while 37.5 ml of a 1.6M solution of butyllithium in hexane was added dropwise. It was warmed to -10° C. during 45 min and stirred at this temperature for another 30 min. The mixture was cooled again below -60° C. followed by dropwise addition of 35.7 g (190 mmol) triisopropyl borate. After warming to room temperature the mixture was quenched with 70 ml 2N hydrochloric acid and stirred for 1 h. The organic layer was washed three times with 30 ml 2N hydrochloric acid, twice with water, and extracted with 2N sodium hydroxide solution, successively. The alkaline aqueous layer was brought to pH5 and extracted with tert.-butylmethylether. All organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the pale yellow crystalline boronic acid which was used for the next step without further purification. [0324] yield: 9.4 g (83percent); MS 196 (M+).
References: [1] Patent: US2004/9976, 2004, A1, . Location in patent: Page/Page column 21-22.
[2] Patent: EP1266897, 2002, A2, . Location in patent: Page 35.
  • 3
  • [ 23145-05-3 ]
  • [ 227802-36-0 ]
  • [ 5419-55-6 ]
  • [ 20485-44-3 ]
  • [ 223576-64-5 ]
YieldReaction ConditionsOperation in experiment
73% With hydrogenchloride; n-butyllithium In PPA; hexane Step A:
5-Chlorobenzofuran-2-boronic acid
5-Chlorobenzofuran was prepared by heating 4-chlorophenoxyacetaldehyde dimethylacetal in polyphosphoric acid; yield: 73percent.
To a solution of 8.8 g (57.7 mmol) 5-chlorobenzofuran in 250 ml dry ether were added 7.32 g (63.0 mmol) tetramethylethylenediamine (TMEDA).
The solution was kept below -60° C. under argon, while 37.5 ml of a 1.6M solution of butyllithium in hexane was added dropwise.
It was warmed to -10° C. during 45 min and stirred at this temperature for another 30 min.
The mixture was cooled again below -60° C. followed by dropwise addition of 35.7 g (190 mmol) triisopropyl borate.
After warming to room temperature the mixture was quenched with 70 ml 2N hydrochloric acid and stirred for 1 h.
The organic layer was washed three times with 30 ml 2N hydrochloric acid, twice with water, and extracted with 2N sodium hydroxide solution, successively.
The alkaline aqueous layer was brought to pH5 and extracted with tert.-butylmethylether.
All organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the pale yellow crystalline boronic acid which was used for the next step without further purification.
yield: 9.4 g (83percent); MS 196 (M+).
References: [1] Patent: US6410562, 2002, B1, .
  • 4
  • [ 23145-05-3 ]
  • [ 5419-55-6 ]
  • [ 223576-64-5 ]
References: [1] Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387.
  • 5
  • [ 23145-05-3 ]
  • [ 5419-55-6 ]
  • [ 7732-18-5 ]
  • [ 223576-64-5 ]
References: [1] Patent: WO2012/119046, 2012, A2, . Location in patent: Page/Page column 69.
 

Historical Records

Technical Information

Categories