(2S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid

Basic Information

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CAS Number

16832-24-9

Molecular Formula

C13H15N3O2

Molecular Weight

245.28 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

248-249 ºC

SMILES

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C1=CC=C(C=C1)CN2C=C(N=C2)CC(C(=O)O)N

InChI

InChI=1S/C13H15N3O2/c14-12(13(17)18)6-11-8-16(9-15-11)7-10-4-2-1-3-5-10/h1-5,8-9,12H,6-7,14H2,(H,17,18)/t12-/m0/s1

InChIKey

NMXSWQMJOZUQKY-LBPRGKRZSA-N

Complexity

279

Synonyms & References

English

L-Histidine, 1-(phenylmethyl)-
31534-22-2
(2S)-2-amino-3-(1-benzylimidazol-4-yl)propanoic acid
Nim-Benzyl-L-histidine
1-benzyl-l-histidine
D96883
(S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid
26086-41-9
CS-0269958
BDBM50463190
H-HIS(BZL)-OH
16832-24-9
J-010447
1-Benzylhistidin
SCHEMBL41832
AKOS016010221
EN300-6747953
MFCD00038630
H-His-(Bzl)-OH
N-Im-benzyl-L-histidine
AS-60409
(2S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid
CHEMBL4240267
L-His(Bzl)-OH
NMXSWQMJOZUQKY-LBPRGKRZSA-N
n<Font face='symbol'>t</font>-benzyl-l-histidine
(S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoicacid
DTXSID30185435
(S)-2-Amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid
2-amino-3-(1-benzylimidazol-4-yl)propanoic acid
L-Histidine,1-(phenylmethyl)-

MDL Number

MFCD00038630

FAQ

What are the physical and chemical properties of (2S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid (CAS: 16832-24-9)?

The (2S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid (CAS: 16832-24-9) is a crystalline solid with a molecular weight of approximately 292.33 g/mol. It has a pKₐ value of around 9.5 and is moderately soluble in water. This compound reacts readily with bases due to its amino group and displays moderate reactivity in the presence of acids. It is stable under normal storage conditions but should be protected from moisture and air exposure.

How is (2S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid (CAS: 16832-24-9) typically synthesized?

The synthesis of (2S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid (CAS: 16832-24-9) is typically achieved via a multistep process. Starting from 1-benzyl-1H-imidazole and glycine, the reaction proceeds through condensation followed by amidation. This process involves the use of coupling agents like HATU or EDC and a suitable base like DIPEA. The yield is usually around 70-80%, and the product can be purified by column chromatography or recrystallization.

What industries use (2S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid (CAS: 16832-24-9)?

The (2S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid (CAS: 16832-24-9) is used in the pharmaceutical industry as an intermediate for the synthesis of various drug candidates. It is also utilized in the sensor industry for its ability to interact with metal ions and in semiconductors for its electronic properties. Its unique chemical structure makes it valuable in polymer synthesis for developing functional materials and in biochemistry for studying protein interactions.

What precautions should be taken when handling (2S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid (CAS: 16832-24-9)?

When handling (2S)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid (CAS: 16832-24-9), it is important to use proper personal protective equipment (PPE) including gloves and eye protection. Store the compound in a cool, dry place away from moisture and air. In case of a spill, contain it using absorbent materials and dispose of it according to local regulations. Always consult the Material Safety Data Sheet (MSDS) for detailed safety information and emergency procedures.