Boc-Aib-OH Chemical Properties

Melting point:

118-122 °C

Boiling point:

341.54°C (rough estimate)

Density 

1.1886 (rough estimate)

refractive index 

1.4315 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Crystalline Powder

pka

4.11±0.10(Predicted)

color 

White

BRN 

1953772

InChI

InChI=1S/C9H17NO4/c1-8(2,3)14-7(13)10-9(4,5)6(11)12/h1-5H3,(H,10,13)(H,11,12)

InChIKey

VLHQXRIIQSTJCQ-LURJTMIESA-N

SMILES

C(O)(=O)[C@](C)(C)NC(OC(C)(C)C)=O

CAS DataBase Reference

30992-29-1(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29241990

MSDS

• Language:English Provider:alpha-(Boc-amino)isobutyric acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Boc-Aib-OH Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

Boc-α-Methylalanine is used as a catalyst in the preparation of 2-benzopyranone derivatives (isocoumarin) as well as arylbenzeneacetic acids.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

The general procedure for the synthesis of 2-((tert-butoxycarbonyl)amino)-2-methylpropionic acid from di-tert-butyl dicarbonate and 2-aminoisobutyric acid is as follows: Preparation of Example 26: 2-(tert-butoxycarbonylamino)-2-methylpropionic acid 200 mg (1.94 mmol) of 2-amino-2-methylpropionic acid was dissolved in a solvent mixture of 8.0 mL of 1.0 N NaOH solution and 8.0 mL of 1,4-dioxane, followed by the addition of 846 mg (3.88 mmol) of di-tert-butyl dicarbonate (Boc2O). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, 1,4-dioxane was removed by distillation under reduced pressure. The residue was adjusted to pH 3 with 1N HCl solution and then extracted with 320 mL of ethyl acetate. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 315 mg of the white solid product 2-(tert-butoxycarbonylamino)-2-methylpropanoic acid in 80% yield. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 5.07 (brs, 1H), 1.54 (s, 6H), 1.45 (s, 9H).

References

[1] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 4, p. 1391 - 1397
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 20, p. 5679 - 5683
[3] Angew. Chem., 2018, vol. 130, p. 5781 - 5785,5
[4] Patent: US2015/210635, 2015, A1. Location in patent: Paragraph 0502-0504
[5] Patent: EP2865664, 2015, A1. Location in patent: Paragraph 0118; 0119

Boc-Aib-OH(30992-29-1)Related Product Information

• PENICILLIN V
• 3-Aminophenol
• Methyl acrylate
• ALTRENOGEST
• Isobutyric acid
• 2-(4-Chlorophenoxy)-2-methylpropionic acid
• EC 2.6.1.2
• Dimethyl 2,2'-azobis(2-methylpropionate)
• Bensulfuron methyl
• Phenprobamate
• D-Alanine
• CARBONYL SULFIDE
• Glycine
• Kresoxim-methyl
• Diethylstilbestrol
• 6-Aminocaproic acid
• Tris(hydroxymethyl)aminomethane
• α-Lipoic Acid