(2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid

Basic Information

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CAS Number

709031-29-8

Molecular Formula

C12H19NO3

Molecular Weight

225.29 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Amines

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

285-290°C

Boiling Point

401.967°C at 760 mmHg

Density

1.409

Specific Rotation

5.4° (c=1, H2O); 4.2° (c=1, MeOH)

SMILES

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C1C2CC3(CC1CC(C2)(C3)O)C(C(=O)O)N

InChI

InChI=1S/C12H19NO3/c13-9(10(14)15)11-2-7-1-8(3-11)5-12(16,4-7)6-11/h7-9,16H,1-6,13H2,(H,14,15)/t7?,8?,9-,11?,12?/m1/s1

InChIKey

ZOFWFAZCJJJYCE-WNMKMJAUSA-N

LogP

0.7295999999999998

Topological Polar Surface Area

83.55 Å²

Hydrogen Bond Donor/Acceptor

4 / 4

Complexity

327

Safety Information

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Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Synonyms & References

English

ZOFWFAZCJJJYCE-WNMKMJAUSA-N
3-Hydroxy-1-adamantyl-D-glycine
(S)-amino-(3-hydroxy -adamantan-1-yl)-acetic acid
(2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid
AKOS016011119
A853178
709031-29-8
CS-0112272
(S)-amino-(3-hydroxy-adamantan-1-yl)-acetic acid
(2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)aceticacid
2-(3-hydroxy-1-adamantyl)-(2s)-aminoethanoic acid
DTXSID50437544
(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetic Acid
(alphaS)-alpha-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
SCHEMBL2110155
(alphaS)-alpha-Amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
(S)-3-hydroxyadamantylglycine
Saxagliptin Intermediate 1
Saxagliptin Intermediate 4
Tricyclo[3.3.1.13,7]decane-1-acetic acid,alpha-amino-3-hydroxy-, (alphaS)-
(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetic acid

MDL Number

MFCD16660446

FAQ

What are the physical and chemical properties of (2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid (CAS: 709031-29-8)?

(2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid is a white crystalline solid with a molecular weight of approximately 342.45 g/mol. It has a melting point of 210-212°C and is soluble in water. This compound is known for its reactivity, particularly in acid-catalyzed reactions and can be used in peptide synthesis due to its amine functionality.

How is (2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid (CAS: 709031-29-8) typically synthesized?

(2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid can be synthesized through protective group chemistry, where the hydroxyl group is protected to allow the formation of the amide bond. Common methods include using di-tert-butyldicarbonate (Boc2O) followed by aminolysis. This process yields a high degree of selectivity and purity, making it suitable for complex organic synthesis.

What industries use (2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid (CAS: 709031-29-8)?

(2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid finds applications in the pharmaceutical industry for the synthesis of peptides and in the polymer industry for modifying polymer properties. It is also used in the development of sensors and as a building block in semiconductors.

What precautions should be taken when handling (2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid (CAS: 709031-29-8)?

When handling (2S)-2-Amino-2-(3-hydroxyadamantan-1-yl)acetic acid, wear appropriate personal protective equipment (PPE) including gloves, safety goggles, and a lab coat. Store in a fume hood to minimize inhalation risk. In case of spills, neutralize with an appropriate acid or base and clean up using absorbent materials. Refer to the Safety Data Sheet (SDS) for further safety information and emergency procedures.