Boc-5-aminopentanoic acid Chemical Properties

Melting point:

48-52 °C(lit.)

Boiling point:

160-168 °C0.8 mm Hg(lit.)

Density 

1.1518 (rough estimate)

refractive index 

1.4500 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Powder

pka

4.72±0.10(Predicted)

color 

Off-white

BRN 

2048862

CAS DataBase Reference

27219-07-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-21

HazardClass 

IRRITANT

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

Boc-5-aminopentanoic acid Usage And Synthesis

Description

Boc-5-aminopentanoic acid can be used as a PROTAC linker in the synthesis of PROTACs. Boc-5-aminopentanoic acid is an alkane chain with terminal carboxlic acid and Boc-protected amino groups. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The Boc group can be deprotected under mild acidic conditions to form the free amine.

Chemical Properties

solid

Uses

Boc-5-aminovaleric acid can be used to synthesize inhibitors of bacterial quorum seining and biofilm formation. It can also be used to synthesize diblock and triblock copolymers.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 2424, 1983 DOI: 10.1021/jo00162a028

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Example 4: To a mixed solution of 100 mL of 2% aqueous sodium hydroxide and 100 mL of dioxane containing 5-aminopentanoic acid (5.85 g, 0.05 mol), a solution of dioxane containing di-tert-butyl dicarbonate (10.9 g, 0.05 mol) was slowly added dropwise. The reaction mixture was stirred at room temperature for 18 h and then acidified with 1 N hydrochloric acid to pH 3. The acidified reaction mixture was extracted three times with dichloromethane. The organic layers were combined, washed sequentially with water and dried over sodium sulfate, and concentrated under reduced pressure to give 10.1 g (93.5% yield) of 5-(tert-butoxycarbonylamino)pentanoic acid as a white crystalline solid.

References

[1] Journal of the American Chemical Society, 2018, vol. 140, # 44, p. 14599 - 14603
[2] ChemMedChem, 2016, p. 1172 - 1187
[3] ChemMedChem, 2016, vol. 11, # 11, p. 1172 - 1187
[4] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 4, p. 402 - 407
[5] Patent: US4476228, 1984, A

Boc-5-aminopentanoic acid(27219-07-4)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• Glycine
• ALTRENOGEST
• 5-AMINOVALERIC ACID
• MAGNESIUM DIPROPYLACETATE HYDRATE
• Estradiol valerate
• 2-Propylpentanoic acid
• Pivalic acid
• N-Carbobenzyloxyglycine
• 1-(Boc-amino)cyclopropanecarboxylic acid
• BOC-HYP(BZL)-OH
• BOC-L-2-AMINOADIPIC ACID
• Boc-Hyp-OH
• (3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid
• BOC-L-Proline
• N-Boc-trans-4-Hydroxy-L-proline methyl ester
• Fmoc-Orn(Boc)-OH