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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-24/25

WGK Germany 

3

F 

10-21

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

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

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