1-BROMO-CYCLOBUTANECARBOXYLIC ACID ETHYL ESTER Chemical Properties

Boiling point:

85-88 °C12 mm Hg(lit.)

Density 

1.279 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.471(lit.)

Flash point:

175 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear colorless

Stability:

Light Sensitive

InChIKey

UTVNSHXHFRIXMM-UHFFFAOYSA-N

CAS DataBase Reference

35120-18-4

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29162000

MSDS

• Language:English Provider:SigmaAldrich

1-BROMO-CYCLOBUTANECARBOXYLIC ACID ETHYL ESTER Usage And Synthesis

Chemical Properties

Clear colorless liquid

Uses

Ethyl 1-bromocyclobutanecarboxylate was used in the synthesis of 1?aminocyclobutane carboxylic acid.

Synthesis

To a solution of ethyl cyclobutanecarboxylate (10 g) in carbon tetrachloride (100 mL) was sequentially added N-bromosuccinimide (NBS, 20.83 g) and azobisisobutyronitrile (AIBN, 1.281 g). The reaction mixture was stirred at 80 °C for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (50 mL) and the mixture was extracted with ethyl acetate (3 x 50 mL). The organic phases were combined and washed sequentially with saturated sodium bicarbonate solution (50 mL), water (50 mL) and saturated saline (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=100:1) to afford the target product ethyl 1-bromocyclobutanecarboxylate (10 g) as a yellow oil.1H NMR (400MHz, CDCl3) δ: 4.26 (q, J=14.4,7.2Hz, 2H), 2.95-2.88 (m, 2H), 2.67- 2.59 (m, 2H), 2.26-2.21 (m, 1H), 1.91-1.86 (m, 1H), 1.32 (t, J=7.2Hz, 3H).

References

[1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 11002 - 11005
[2] Chemical Communications, 2015, vol. 51, # 42, p. 8773 - 8776
[3] Organic Letters, 2016, vol. 18, # 9, p. 2040 - 2043
[4] Patent: WO2018/15411, 2018, A1. Location in patent: Paragraph 0165; 0166; 0167; 0168; 0169; 0170
[5] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 11, p. 988 - 993

1-BROMO-CYCLOBUTANECARBOXYLIC ACID ETHYL ESTER(35120-18-4)Related Product Information

• ETHYL 4-AMINO-5-IMIDAZOLECARBOXYLATE
• Ethyl5-bromo-1,3,4-thiadiazole-2-carboxylate
• TRANS,TRANS-3,4,5-TRIFLUOROPHENYL 4''-ETHYLBICYCLOHEXYL-4-CARBOXYLATE
• 4-cyanophenyl 4-trans-(4-ethylcyclohexyl)benzoate
• ethyl 2-(2-aminopyrimidin-4-yl)acetate
• ETHYL 4-CHLOROBUTYRATE
• 5-BROMO-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
• 4-ETHYLBENZOIC ACID-4'-CYANOPHENYL ESTER
• Ethyl 4-(benzyloxy)-3-oxobutanoate
• ETHYL 4-METHYLOCTANOATE
• ethyl 5-oxo-DL-prolinate
• ETHYL 4-METHYLBENZOYLFORMATE
• Ethyl 5-AMinoopyrazolo[1,5-a]pyridine-3-carboxylate
• ETHYL 4-(2-CHLOROACETAMIDO)BENZOATE
• ethyl 2‐(2‐chloropyriMidin‐5‐yl)acetate
• Ethyl4-Methyl-2-(thiophen-2-yl)thiazole-5-carboxylate
• ETHYL (2-METHOXYBENZOYL)ACETATE
• ethyl 3-hydroxycyclohexanecarboxylate