|
|
| | tert-Butyl 3-bromopropylcarbamate Basic information |
| Product Name: | tert-Butyl 3-bromopropylcarbamate | | Synonyms: | N-(TERT-BUTOXYCARBONYL)-3-BROMOPROPYLAMINE;N-(3-BROMOPROPYL)CARBAMIC ACID TERT-BUTYL ESTER;TERT-BUTYL N-(3-BROMOPROPYL)CARBAMATE;(3-BROMO-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER;3-(BOC-AMINO)PROPYL BROMIDE;TERT-BUTYL 3-BROMOPROPYLCARBAMATE;CarbaMic acid, N-(3-broMopropyl)-, 1,1-diMethylethyl ester;N-(3-Bromopropyl)carbamic Acid tert-Butyl Ester
tert-Butyl N-(3-Bromopropyl)carbamate
3-(Boc-amino)propyl Bromide | | CAS: | 83948-53-2 | | MF: | C8H16BrNO2 | | MW: | 238.12 | | EINECS: | | | Product Categories: | | | Mol File: | 83948-53-2.mol |  |
| | tert-Butyl 3-bromopropylcarbamate Chemical Properties |
| Melting point | 37-39 °C | | Boiling point | 285.3±23.0 °C(Predicted) | | density | 1.279±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Ethyl Acetate (Sparingly), Methanol (Slightly) | | pka | 12.48±0.46(Predicted) | | form | Low Melting Solid | | color | White | | BRN | 4176344 | | InChI | InChI=1S/C8H16BrNO2/c1-8(2,3)12-7(11)10-6-4-5-9/h4-6H2,1-3H3,(H,10,11) | | InChIKey | IOKGWQZQCNXXLD-UHFFFAOYSA-N | | SMILES | C(OC(C)(C)C)(=O)NCCCBr | | CAS DataBase Reference | 83948-53-2 |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 26-24/25 | | WGK Germany | 3 | | F | 10-21 | | HS Code | 29241990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | tert-Butyl 3-bromopropylcarbamate Usage And Synthesis |
| Chemical Properties | White low melting solid | | Uses | 3-(Boc-amino)propyl bromide can be used as an alkylating reagent for the synthesis of:
- Benzydamine analogs to be used as activators for soluble guanylate cyclase.
- N-substituted chromenotriazolopyrimidine, human murine double minute 2 (MDM2) inhibitor.
- Protected amines from piperidine derivatives to be further used for synthesis of sulfonamide series.
It can also be used for the post-polymerization quaternization of polymers to synthesize functional cationic polymers and antimicrobial agents. | | reaction suitability | reagent type: cross-linking reagent | | Synthesis | The general procedure for the synthesis of N-Boc-3-aminopropyl bromide from di-tert-butyl dicarbonate and 3-bromopropylamine hydrobromide is as follows: refer to Example 4, Synthesis of Boc-Aminopropyl Bromide: 1.222 g (5.58 mmol) of 3-bromopropylamine hydrobromide was dissolved in 20 mL of dichloromethane to which was added under cooling in an ice bath 0.778 mL (5.58 mmol) of triethylamine and 50 mL of dichloromethane. A solution of 1.214 g (5.56 mmol) of di-tert-butyl dicarbonate (Boc2O) was added slowly and dropwise over a period of 10 min, followed by stirring of the reaction mixture. After continued stirring at room temperature for 50 min, ethyl acetate was added to the reaction system and the organic phase was washed sequentially with 5% aqueous citric acid, water and saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent to give 1.304 g of N-Boc-3-aminopropyl bromide in 98% yield. The structure of the product was confirmed by 1H-NMR. 1H-NMR (500 MHz, CDCl3) δ (ppm) = 1.44 (9H, s, Boc group), 2.05 (2H, quintet, -NHCH2CH2CH2Br), 3.28 (2H, quartet, -NHCH2CH2CH2Br), 3.44 ( 2H, triplet, -NHCH2CH2CH2Br), 4.64 (1H, s, NH). | | References | [1] Patent: EP1710257, 2006, A1
[2] Chemical Communications, 2013, vol. 49, # 51, p. 5784 - 5786
[3] Patent: EP3363463, 2018, A2. Location in patent: Paragraph 0170
[4] Patent: WO2003/99858, 2003, A1. Location in patent: Page 37
[5] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10058 - 10066 |
| | tert-Butyl 3-bromopropylcarbamate Preparation Products And Raw materials |
|