Carbamic acid, 4-pentynyl-, 1,1-dimethylethyl ester (9CI) Chemical Properties

Boiling point:

267.2±23.0 °C(Predicted)

Density 

0.965±0.06 g/cm3(Predicted)

storage temp. 

Storage temp. 2-8°C

pka

12.61±0.46(Predicted)

form 

Solid

color 

White to off-white

BRN 

6918435

InChI

InChI=1S/C10H17NO2/c1-5-6-7-8-11-9(12)13-10(2,3)4/h1H,6-8H2,2-4H3,(H,11,12)

InChIKey

JTPJJKZSKWNWKK-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCCC#C

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2735PSN1 8 / PGII

WGK Germany 

3

HazardClass 

8

Carbamic acid, 4-pentynyl-, 1,1-dimethylethyl ester (9CI) Usage And Synthesis

Uses

N-Boc-4-pentyne-1-amine is a PROTAC linker, which refers to the alkyl chain composition. N-Boc-4-pentyne-1-amine can be used in the synthesis of the PROTAC MG-277 (HY-130122)[1]. N-Boc-4-pentyne-1-amine is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

reaction suitability

reaction type: click chemistry

Synthesis

Pent-4-yn-1-amine (4.91 g, 59.06 mmol, 1.00 eq.) was dissolved in dichloromethane (40 mL) at 0 °C, followed by triethylamine (8.95 g, 88.45 mmol, 1.50 eq.). A solution of di-tert-butyl dicarbonate (12.88 g, 59.02 mmol, 1.00 eq.) in dichloromethane (20 mL) was added dropwise with stirring. The reaction mixture was gradually warmed to room temperature and stirred at that temperature overnight. Upon completion of the reaction, the mixture was concentrated under reduced pressure and subsequently purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether from 1:50 to 1:40) to afford N-BOC-4-pentyn-1-amine (4.59 g, 43% yield) as a light yellow oil.

IC 50

Alkyl/ether

References

[1] Yang J, et al. Simple Structural Modifications Converting a Bona fide MDM2 PROTAC Degrader into a Molecular Glue Molecule: A Cautionary Tale in the Design of PROTAC Degraders. J Med Chem. 2019 Oct 21. DOI:10.1021/acs.jmedchem.9b00846

Carbamic acid, 4-pentynyl-, 1,1-dimethylethyl ester (9CI)(151978-50-6)Related Product Information

• pfpat
• GLUTARYL DICHLORIDE
• Glutacondianil hydrochloride
• 4-Pentynoic acid, methyl ester
• 4-Pentenylboronic acid
• ETHYL 4-PENTENOATE
• pent-4-yne-1-sulfonyl chloride
• PENT-4-YNAL (IN DCM 30% W/W)
• ethyl pent-4-ynoate
• Pent-4-yn-1-amine,hydrochloride