DL-2-AMINO-3-METHYL-1-BUTANOL Chemical Properties

Melting point:

31-32℃

Boiling point:

75-77 °C8 mm Hg(lit.)

Density 

0.936 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4543(lit.)

Flash point:

194 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Soluble in water

form 

Liquid

pka

12.82±0.10(Predicted)

color 

Clear yellow

optical activity

0.3825°(C=1g/100ml ETOH)

InChI

InChI=1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3

InChIKey

NWYYWIJOWOLJNR-UHFFFAOYSA-N

SMILES

C(O)C(N)C(C)C

CAS DataBase Reference

16369-05-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37

RIDADR 

2735

WGK Germany 

3

HS Code 

29221990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

DL-2-AMINO-3-METHYL-1-BUTANOL Usage And Synthesis

Chemical Properties

CLEAR YELLOW LIQUID

Uses

2-Amino-3-methyl-1-butanol was used in the synthesis of 1-allyl-2-pyrroleimines. It was also used as chiral nucleophile in the total synthesis of benanomicin-pradimicin antibiotics. It was used as homochiral guest compound during synthesis of crown ethers containing two chiral subunits.

Definition

ChEBI: 2-Amino-3-methyl-1-butanol is an amino alcohol.

Synthesis

Example 2: To a dry 12 liter glass reaction vessel (with equipment as described in Example 1) was added 900 grams (7.7 moles) of DL-valine and 2.5 liters of tetrahydrofuran. 1.05 liters (8.5 moles) of boron trifluoride diethyl ether compound and 0.85 liters (8.5 moles) of borane-dimethyl sulfide complex were added sequentially according to the method of Example 1, followed by refluxing. The addition process lasted for 8 hours and heating was continued for 3 hours after the addition was completed. The reaction mixture was quenched with 0.75 liters of tetrahydrofuran/water mixture and subsequently hydrolyzed with 24.6 moles of aqueous sodium hydroxide. The product was separated according to the method described in Example 1, resulting in 494 g (62% yield) of 2-amino-3-methyl-1-butanol having a boiling point of 78°-79°C (8 mm), refractive index n20D 1.4543, and a purity of 97% by gas chromatography (glc) analysis.

References

[1] Patent: US3935280, 1976, A

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