tert-Butyl N-(4-aminobutyl)carbamate Chemical Properties

Boiling point:

292.9±23.0 °C(Predicted)

Density 

0.984 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.460

Flash point:

109 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, DMSO, Methanol

pka

12.86±0.46(Predicted)

form 

Liquid

color 

Clear colorless to light yellow

BRN 

1937878

InChI

InChI=1S/C9H20N2O2/c1-9(2,3)13-8(12)11-7-5-4-6-10/h4-7,10H2,1-3H3,(H,11,12)

InChIKey

ZFQWJXFJJZUVPI-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCCCN

CAS DataBase Reference

68076-36-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34-24

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2735 8/PG 3

WGK Germany 

3

F 

10-34

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

tert-Butyl N-(4-aminobutyl)carbamate Usage And Synthesis

Chemical Properties

Clear colourless viscous liquid

Uses

N-Boc-1,4-diaminobutane is used in preparation of pharmacologically active compounds, preparation of spermidine analogues and in introduction of a C4-spacer. It serve as intermediates of medicine.

Uses

suzuki reaction

reaction suitability

reagent type: cross-linking reagent

Synthesis

Synthesis of compound 19: 1,4-Butanediamine (1 g, 11.36 mmol, 5 eq.) was dissolved in dichloromethane (15 ml). To this solution was slowly added di-tert-butyl dicarbonate (Boc2O, 0.619 g, 2.83 mmol, 1 eq.) dissolved in dichloromethane (15 ml). The reaction mixture was stirred at room temperature for 16 hours. The reaction progression was monitored by thin layer chromatography (TLC, unfolding agent ratio CH2Cl2:MeOH:33% NH4OH aqueous solution = 8:2:0.2). Upon completion of the reaction, the reaction mixture was filtered to remove insoluble impurities and the filtrate was concentrated by rotary evaporator. The resulting oily residue was dissolved with ethyl acetate (15 ml) and washed with saturated sodium chloride solution (3 x 10 ml) to remove unreacted 1,4-butanediamine. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.520 g of yellow oily product in 97.65% yield. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 1.38 (s, 9H), 1.52-1.59 (m, 4H), 2.34 (brs, 2H, D2O exchange), 2.72-2.79 (m, 2H), 3.19-3.24 (m, 2H), 5.95 (brs, 1H, D2O exchange).

IC 50

Alkyl/ether

References

[1] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 411 - 416
[2] Organic Letters, 2001, vol. 3, # 8, p. 1205 - 1208
[3] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 20, p. 7145 - 7155
[4] Journal of Materials Chemistry, 2011, vol. 21, # 13, p. 4850 - 4860
[5] Organic Letters, 2015, vol. 17, # 22, p. 5626 - 5629

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