| Identification | More | [Name]
N-Boc-cadaverine | [CAS]
51644-96-3 | [Synonyms]
1-BOC-AMINO-1,5-PENTANEDIAMINE
BOC-1,5-DIAMINOPENTANE
BOC-1,5-DIAMINOPENTANE HCL
BOC-1,5-DIAMINOPENTANE HYDROCHLORIDE
BOC-DAPE HCL
BOC-DAPE-OH
BOC-DIAMINOPENTANE HCL
BOC-NH(CH2)5NH2 HCL
N-1-BOC-1,5-DIAMINOPENTANE HCL
N-1-T-BUTOXYCARBONYL-1,5-DIAMINOPENTANE HYDROCHLORIDE
N-(5-AMINOAMYL)CARBAMIC ACID TERT-BUTYL ESTER
N-(5-AMINOPENTYL)CARBAMIC ACID TERT-BUTYL ESTER
N-BOC-1,5-DIAMINOPENTANE
N-BOC-1,5-PENTANEDIAMINE
N-Boc-cadaverine
N-T-BUTYLOXYCARBONYL-1,5-DIAMINOPENTANE HYDROCHLORIDE
N-(TERT-BUTOXYCARBONYL)-1,5-DIAMINOPENTANE
N-(TERT-BUTOXYCARBONYL)-1,5-PENTANEDIAMINE
N-TERT-BUTYLOXYCARBONYL-1,5-DIAMINOPENTANE HYDROCHLORIDE
TERT-BUTYL N-(5-AMINOAMYL)CARBAMATE | [Molecular Formula]
C10H22N2O2 | [MDL Number]
MFCD00210020 | [Molecular Weight]
202.29 | [MOL File]
51644-96-3.mol |
| Chemical Properties | Back Directory | [Boiling point ]
309.2±25.0 °C(Predicted) | [density ]
0.972 g/mL at 20 °C(lit.)
| [refractive index ]
n20/D 1.460
| [Fp ]
109 °C | [storage temp. ]
2-8°C
| [form ]
Oil | [pka]
12.91±0.46(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2735 8/PG 3
| [WGK Germany ]
3
| [F ]
10-34 | [HazardClass ]
8 | [PackingGroup ]
Ⅲ | [HS Code ]
2924190090 |
| Hazard Information | Back Directory | [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).
| [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 |
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