ChemicalBook > CAS DataBase List > 3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER

3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER

Product Name
3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER
CAS No.
480449-99-8
Chemical Name
3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER
Synonyms
benzyl 3-hydroxycyclobutane-1-carboxylate;benzyl 3-hydroxycyclobutanecarboxylate;Benzyl 3-hydroxycyclobutanecarboxylate - B10561;3-Hydroxy-cyclobutanecarboxylic acid benzyl este;3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER;Cyclobutanecarboxylic acid, 3-hydroxy-, phenylMethyl ester
CBNumber
CB72466414
Molecular Formula
C12H14O3
Formula Weight
206.24
MOL File
480449-99-8.mol
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3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER Property

Boiling point:
326.2±35.0 °C(Predicted)
Density 
1.240
storage temp. 
Sealed in dry,Room Temperature
pka
14.72±0.40(Predicted)
form 
solid
Appearance
Colorless to light yellow Liquid
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Safety

HS Code 
2918999090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHB00064
Product name
Benzyl 3-hydroxycyclobutanecarboxylate
Purity
AldrichCPR
Packaging
1 g
Price
$639
Updated
2025/07/31
TRC
Product number
B297043
Product name
Benzyl3-Hydroxycyclobutanecarboxylate
Packaging
1g
Price
$100
Updated
2021/12/16
SynQuest Laboratories
Product number
2623-1-63
Product name
Benzyl 3-hydroxycyclobutanecarboxylate
Packaging
250mg
Price
$38
Updated
2021/12/16
SynQuest Laboratories
Product number
2623-1-63
Product name
Benzyl 3-hydroxycyclobutanecarboxylate
Packaging
1g
Price
$125
Updated
2021/12/16
SynQuest Laboratories
Product number
2623-1-63
Product name
Benzyl 3-hydroxycyclobutanecarboxylate
Packaging
5G
Price
$450
Updated
2021/12/16
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3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER Chemical Properties,Usage,Production

Synthesis

198995-91-4

480449-99-8

Example 261: General procedure for the synthesis of benzyl 3-hydroxycyclobutanecarboxylate from benzyl 3-oxocyclobutanecarboxylate: 1. triethylamine (2 mL, 14.04 mmol) and benzyl bromide (1.2 mL, 10.0 mmol) were added to a solution of 3-oxocyclobutane-1-carboxylic acid (1.0 g, 8.77 mmol) in THF (10 mL), and stirred for 2 hours at room temperature. EtOAc (10 mL) was added and the mixture was washed sequentially with water, 1 M hydrochloric acid and brine. The organic layer was dried with sodium sulfate and concentrated in vacuum. The residue was purified by fast column chromatography (FCC) using a gradient elution with a hexane solution of 0-15% EtOAc to give benzyl 3-oxocyclobutane-1-carboxylate (0.938 g, 53%). 2. Benzyl 3-oxocyclobutane-1-carboxylate (0.800 g, 3.92 mmol) was dissolved in a mixture of THF (2.5 mL) and water (2.5 mL), and cooled to 0°C. Sodium borohydride (0.051 g, 1.96 mmol) was added and stirred at room temperature for 1 hour. After vacuum concentration, EtOAc (10 mL) was added, washed sequentially with water and brine, and the organic layer was dried with sodium sulfate and concentrated. The residue was purified by FCC and eluted using a gradient of 0-10% EtOAc in hexane solution to give benzyl 3-hydroxycyclobutane-1-carboxylate (0.715 g, 88%). 3. Benzyl 3-hydroxycyclobutane-1-carboxylate (0.400 g, 1.94 mmol) was dissolved in THF (10 mL) and phenol (0.547 g, 5.83 mmol) and triphenylphosphine (0.662 g, 2.52 mmol) were added. Diethyl azodicarboxylate (0.4 mL, 2.52 mmol) was added slowly and stirred at room temperature for 24 hours. After evaporation, it was extracted with EtOAc (3 x 10 mL) and the organic layer was washed with brine and concentrated. The residue was purified by FCC and eluted using a gradient of 0-15% EtOAc in hexane solution to give benzyl 3-phenoxycyclobutane-1-carboxylate (0.450 g, 82%). 4. Benzyl 3-phenoxycyclobutane-1-carboxylate (0.400 g, 1.42 mmol) was dissolved in EtOH (10 mL) and 10% palladium carbon (0.010 g) was added. The solution was stirred at room temperature under hydrogen atmosphere for 2 hours. The filtrate was filtered and evaporated and the residue was purified by FCC using a gradient elution with hexane solution of 0-10% EtOAc to give 3-phenoxycyclobutane-1-carboxylic acid (0.245 g, 95%). 5. Finally, 2-N-methyl-6-[5-(3-phenoxycyclobutyl)-1,2,4-oxadiazol-3-yl] was prepared from 3-phenoxycyclobutane-1-carboxylic acid (0.190 g, 0.985 mmol) and 4-amino-N-hydroxy-6-[methyl(phenyl)amino]-1,3,5-triazine-2-carboxamidine (0.150 g, 0.579 mmol) -2-N-phenyl-1,3,5-triazine-2,4-diamine in a manner similar to the preparation of Intermediate 1 (as described in Example 209). The residue was purified by FCC, eluting using a 10% MeOH hexane solution to give a mixture of isomers of benzyl 3-hydroxycyclobutanecarboxylate (0.095 g, 42%).

References

[1] Patent: WO2012/35023, 2012, A1. Location in patent: Page/Page column 91-92
[2] Patent: US2015/133422, 2015, A1. Location in patent: Paragraph 0473; 0474
[3] Patent: WO2013/74387, 2013, A1. Location in patent: Page/Page column 52
[4] Patent: EP1577301, 2005, A1. Location in patent: Page/Page column 145
[5] Patent: EP1405852, 2004, A1. Location in patent: Page 133

3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER manufacturers

Career Henan Chemical Co
Product
3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER 480449-99-8
Price
US $3.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1kg,5kg,50kg
Release date
2020-01-18

480449-99-8, 3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTERRelated Search:


  • 3-HYDROXY-CYCLOBUTANECARBOXYLIC ACID BENZYL ESTER
  • benzyl 3-hydroxycyclobutanecarboxylate
  • 3-Hydroxy-cyclobutanecarboxylic acid benzyl este
  • Cyclobutanecarboxylic acid, 3-hydroxy-, phenylMethyl ester
  • benzyl 3-hydroxycyclobutane-1-carboxylate
  • Benzyl 3-hydroxycyclobutanecarboxylate - B10561
  • 480449-99-8