3-(Aminomethyl)-5-methylhexanoic acid

Basic Information

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CAS Number

128013-69-4

Molecular Formula

C8H17NO2

Molecular Weight

159.23 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Physical Properties

Melting Point

148-150oC

Boiling Point

274 ºC

Flash Point

119 ºC

SMILES

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CC(C)CC(CC(=O)O)CN

InChI

InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)

InChIKey

AYXYPKUFHZROOJ-UHFFFAOYSA-N

LogP

1.0821

Topological Polar Surface Area

63.31999999999999 Å²

Hydrogen Bond Donor/Acceptor

3 / 3

Complexity

123

Synonyms & References

English

128013-69-4
AMY33454
NCGC00095186-02
PHARMA-0589
.gamma.-Aminobutyric acid, 3-isobutyl-
130912-52-6
FT-0643142
DS-10736
CS-0113684
FT-0674010
3-(Aminomethyl)-5-methylhexanoicacid
SCHEMBL15497
3-(aminomethyl)-5-methylhexanoic acid
CHEMBL88034
BCP17115
AC-1337
rac-Pregabalin
US9663479, Pregabalin
Hexanoic acid, 3-(aminomethyl)-5-methyl-
R-Pregabalin
BCP33617
rac-Pregabalin; Hexanoic acid, 3-(aminomethyl)-5-methyl-; 3-(Aminomethyl)-5-methylhexanoic acid; (+/-)-Pregabalin
AB87416
Hexanoic acid, 3-(aminomethyl)-5-methyl-, (S)-
FT-0648922
AKOS005638873
Pregabalin EP Impurity B;(3R)-3-(aminomethyl)-5-methylhexanoic acid
DTXSID20861392
NCGC00095186-01
3-(aminomethyl)-5-methyl-hexanoic acid
3-Aminomethyl-5-methyl-hexanoic acid

MDL Number

MFCD00906155

FAQ

What are the physical and chemical properties of 3-(Aminomethyl)-5-methylhexanoic acid (CAS: 128013-69-4)?

3-(Aminomethyl)-5-methylhexanoic acid is a white or off-white crystalline powder with a molecular weight of approximately 219.34 g/mol. It has a pKa of about 8.5 and is sparingly soluble in water but soluble in organic solvents like ethanol and acetone. The compound is moderately reactive, especially under basic conditions, and is susceptible to hydrolysis. It is also prone to racemization under acidic conditions.

How is 3-(Aminomethyl)-5-methylhexanoic acid (CAS: 128013-69-4) typically synthesized?

3-(Aminomethyl)-5-methylhexanoic acid is typically synthesized via a multi-step process involving the protection of an amino group, followed by a condensation reaction with a carboxylic acid derivative. Commonly, the amino group is protected using tert-butyloxycarbonyl (Boc) or benzyloxycarbonyl (Z) groups. The protected intermediate is then reacted with 5-methylhexanoic acid chloride or an equivalent derivative under anhydrous conditions, followed by deprotection to yield the desired product. This method provides good yield and selectivity.

What industries use 3-(Aminomethyl)-5-methylhexanoic acid (CAS: 128013-69-4)?

3-(Aminomethyl)-5-methylhexanoic acid finds applications in the pharmaceutical industry as an intermediate in drug synthesis, particularly in the development of prodrugs and peptide-based medications. It is also used in the polymer industry for the modification of polymer properties, and in the production of sensors and semiconductors for its unique chemical functionality.

What precautions should be taken when handling 3-(Aminomethyl)-5-methylhexanoic acid (CAS: 128013-69-4)?

When handling 3-(Aminomethyl)-5-methylhexanoic acid, it is essential to wear appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. Work should be carried out in a well-ventilated area or a fume hood to prevent inhalation. Spills should be cleaned up with caution, using absorbent materials and disposing of waste according to local regulations. Always refer to the Safety Data Sheet (SDS) for detailed handling and disposal instructions.