N-Boc-cadaverine Chemical Properties

Boiling point:

309.2±25.0 °C(Predicted)

Density 

0.972 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,2-8°C

pka

12.91±0.46(Predicted)

form 

Oil

color 

Yellow

BRN 

3603658

InChI

InChI=1S/C10H22N2O2/c1-10(2,3)14-9(13)12-8-6-4-5-7-11/h4-8,11H2,1-3H3,(H,12,13)

InChIKey

DPLOGSUBQDREOU-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCCCCN

CAS DataBase Reference

51644-96-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

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 

2924190090

MSDS

• Language:English Provider:SigmaAldrich

N-Boc-cadaverine Usage And Synthesis

Description

tert-Butyl (5-aminopentyl)carbamate can be used as a PROTAC linker in the synthesis of PROTACs. tert-Butyl (5-aminopentyl)carbamate is an alkane chain with terminal amine and Boc-protected amino groups. Amine group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The Boc group can be deprotected under mild acidic conditions to form the free amine.

Uses

Some of the reported applications of N-Boc-cadaverine include:

• Synthesis of of a supermacrocycle that self-assemble to form organic nanotubes.
• Preparation of water-soluble unsymmetrical sulforhodamine fluorophores from monobrominated sulfoxanthene dye.
• Synthesis of functionalized porphyrins as biocompatible carrier system for photodynamic therapy (PDT).

Uses

N-Boc-cadaverine is an intermediate in the synthesis of derivative of the folic acid antagonist Methotrexate (M260675) used in the study of membrane-associated folate transporters from L1210 cells.

reaction suitability

reagent type: cross-linking reagent

Synthesis

GENERAL PROCEDURE: A solution of di-tert-butyl dicarbonate (22 g, 100 mmol) was prepared by dissolving it in methanol (20 mL) under ice bath cooling conditions. This solution was slowly added dropwise over 30 minutes to a stirred methanol solution (160 mL) of 1,5-diaminopentane (1.8 g, 20 mmol). After the dropwise addition was completed, the ice bath was removed and the reaction mixture was allowed to continue stirring at room temperature for 4 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography with the eluent ratio of chloroform:methanol:ammonia = 10:1:0.1 to give tert-butyl N-(5-aminopentyl)carbamate in 83% yield.

IC 50

Alkyl-Chain

References

[1] European Journal of Organic Chemistry, 1998, # 5, p. 853 - 859
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 6, p. 614 - 617
[3] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 20, p. 7145 - 7155
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 20, p. 4933 - 4940
[5] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 5, p. 326 - 333

N-Boc-cadaverine(51644-96-3)Related Product Information

• 4-(tert-ButoxycarbonylaMino)-1-butanol
• N,N,N',N'-Tetramethylchloroformamidinium hexafluorophosphate
• N,N'-Disuccinimidyl carbonate
• 1,3-DI-BOC-2-METHYLISOTHIOUREA
• Carbamic acid, (4-amino-2-butynyl)-, 1,1-dimethylethyl ester (9CI)
• Carbamic acid, (tetrahydro-4-oxo-2H-pyran-3-yl)-, 1,1-dimethylethyl ester (9CI)
• tert-butyl N-(4,4-dimethyl-3-oxopentyl)-N-methylcarbamate
• tert-butyl N-(4-hydroxy-3-methylcyclohexyl)carbamate
• tert-butyl N-(5-aminonaphthalen-1-yl)carbamate
• tert-butyl N-(5-{[(tert-butoxy)carbonyl]amino}-3-oxopentyl)c arbamate
• N,N'-Di-Boc-L-lysine hydroxysuccinimide ester
• Boc-Lys-OH
• Ne-Boc-L-lysine tert-butyl ester hydrochloride
• H-Lys(Boc)-OH
• BOC-HOARG-OH
• BOC-LYS(TFA)-OH
• N-Boc-N'-(2-chlorobenzyloxycarbonyl)-L-lysine
• BOC-LYS(BOC)-OH DCHA