tert-Butyl 3-bromopropylcarbamate

Bezeichnung:tert-Butyl 3-bromopropylcarbamate

CAS-Nr83948-53-2

Englisch Name:tert-Butyl 3-bromopropylcarbamate

CBNumberCB2139373

SummenformelC8H16BrNO2

Molgewicht238.12

MOL-Datei83948-53-2.mol

tert-Butyl 3-bromopropylcarbamate physikalisch-chemischer Eigenschaften

Schmelzpunkt	37-39 °C
Siedepunkt	285.3±23.0 °C(Predicted)
Dichte	1.279±0.06 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	Chloroform (Slightly), Ethyl Acetate (Sparingly), Methanol (Slightly)
Aggregatzustand	Low Melting Solid
pka	12.48±0.46(Predicted)
Farbe	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 Datenbank	83948-53-2

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	26-24/25
WGK Germany	3
F	10-21
HS Code	29241990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

tert-Butyl 3-bromopropylcarbamate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
White low melting solid
Verwenden
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
Synthese

24424-99-5

5003-71-4

83948-53-2

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).
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

tert-Butyl 3-bromopropylcarbamate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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