1-Azetidinecarboxylic acid, 3-methylene-, 1,1-dimethylethyl ester
Uses- Product Name
- 1-Azetidinecarboxylic acid, 3-methylene-, 1,1-dimethylethyl ester
- CAS No.
- 934664-41-2
- Chemical Name
- 1-Azetidinecarboxylic acid, 3-methylene-, 1,1-dimethylethyl ester
- Synonyms
- tert-butyl 3-Methyleneazetidine-1-carboxylate;104893;eneazetidine-1-CarboxyL;1-Boc-3-Methylene-azetidine;1-Boc-3-methylideneazetid...;1-Boc-3-Methylideneazetidine;3-Methylideneazetidine,N-BOCprotected;1-(tert-Butoxycarbonyl)-3-Methyleneazetidine;tert-butyl 3-methylideneazetidine-1-carboxylate;tert-butyl 3-Methyleneazetidine-1-carboxylate - [A0197]
- CBNumber
- CB42525569
- Molecular Formula
- C9H15NO2
- Formula Weight
- 169.22
- MOL File
- 934664-41-2.mol
1-Azetidinecarboxylic acid, 3-methylene-, 1,1-dimethylethyl ester Property
- Boiling point:
- 214.8±29.0 °C(Predicted)
- Density
- 1.02±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C
- form
- clear liquid
- pka
- -1.56±0.20(Predicted)
- color
- Colorless to Almost colorless
- InChI
- InChI=1S/C9H15NO2/c1-7-5-10(6-7)8(11)12-9(2,3)4/h1,5-6H2,2-4H3
- InChIKey
- MECAHFSQQZQZOI-UHFFFAOYSA-N
- SMILES
- N1(C(OC(C)(C)C)=O)CC(=C)C1
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H227Combustible liquid
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
P370+P378In case of fire: Use … for extinction.
P403+P235Store in a well-ventilated place. Keep cool.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- B6011
- Product name
- tert-Butyl 3-Methyleneazetidine-1-carboxylate
- Packaging
- 1G
- Price
- $56
- Updated
- 2025/07/31
- Product number
- B6011
- Product name
- tert-Butyl 3-Methyleneazetidine-1-carboxylate
- Packaging
- 5G
- Price
- $222
- Updated
- 2025/07/31
- Product number
- B423288
- Product name
- tert-Butyl 3-Methyleneazetidine-1-carboxylate
- Packaging
- 1g
- Price
- $330
- Updated
- 2021/12/16
- Product number
- 42565
- Product name
- tert-Butyl3-methyleneazetidine-1-carboxylate,≥95%(GC)
- Purity
- ≥95%(GC)
- Packaging
- 1G
- Price
- $38.14
- Updated
- 2021/12/16
- Product number
- A0197
- Product name
- tert-Butyl 3-Methyleneazetidine-1-carboxylate
- Purity
- 97.0%
- Packaging
- 5g
- Price
- $40
- Updated
- 2021/12/16
1-Azetidinecarboxylic acid, 3-methylene-, 1,1-dimethylethyl ester Chemical Properties,Usage,Production
Uses
tert-Butyl 3-Methyleneazetidine-1-carboxylate is a useful reagent used in the preparation of functionalized difluorocyclopropanes as building blocks for drug discoveries.
Uses
tert-Butyl 3-Methyleneazetidine-1-carboxylate is a useful reagent used in the preparation of functionalized difluorocyclopropanes as building blocks for drug discoveries.
Synthesis
398489-26-4
1779-49-3
934664-41-2
The general procedure for the synthesis of 1-Boc-3-methylene azetidine from 1-Boc-3-azetidinone and methyltriphenylphosphonium bromide was as follows: first, a mixture of potassium ethanol/tert-butanol (15.5 g, 137 mmol) and methyltriphenylphosphonium bromide (49 g, 137 mmol) in ethyl ether (300 mL) was stirred for 1 hour at room temperature. Subsequently, 1-Boc-3-azetidinone (10 g, 58 mmol, dissolved in 100 mL of ether) was added to the reaction system. The reaction mixture was continued to be stirred at 35°C for 2 hours, after which it was cooled to room temperature. The reaction mixture was filtered through a diatomaceous earth pad and the filter cake was washed with ether. The combined filtrates were extracted by partitioning with water, washed twice each sequentially with water and brine, and the organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuum to give an orange-colored oil. The crude product was purified by column chromatography using a hexane solution of 10% ethyl acetate as eluent. The target fraction was collected and concentrated in vacuum to give 1-Boc-3-methylene azetidine (9.80 g, 58 mmol, 100% yield) as a colorless oil. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO) and GC-MS: 1H NMR (400 MHz, DMSO): δ 5.05-4.85 (m, 2H), 4.95-4.63 (m, 4H), 1.45 (s, 9H); GC-MS (C9H15NO2): m/z 169.
References
[1] Patent: WO2007/44515, 2007, A1. Location in patent: Page/Page column 175
[2] Patent: WO2008/76415, 2008, A1. Location in patent: Page/Page column 339-340
[3] Patent: WO2008/124085, 2008, A2. Location in patent: Page/Page column 190
[4] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 5, p. 416 - 421
[5] Patent: WO2012/4400, 2012, A1. Location in patent: Page/Page column 47-48
1-Azetidinecarboxylic acid, 3-methylene-, 1,1-dimethylethyl ester Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 1-Azetidinecarboxylic acid, 3-methylene-, 1,1-dimethylethyl ester manufacturers
- Product
- 1-Boc-3-Methylene-azetidine 934664-41-2
- Price
- US $4500.00/Kg/Drum
- Min. Order
- 1g/Bag
- Purity
- 98%
- Supply Ability
- 50kg/month
- Release date
- 2020-09-09
- Product
- 1-Boc-3-methylideneazetid... 934664-41-2
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20kg
- Release date
- 2018-08-07