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184837

Sigma-Aldrich

2-Amino-3-methyl-1-butanol

97%

Synonym(s):

DL-Valinol

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About This Item

Linear Formula:
(CH3)2CHCH(NH2)CH2OH
CAS Number:
16369-05-4
Molecular Weight:
103.16
EC Number:
240-425-0
MDL number:
MFCD00004730
UNSPSC Code:
12352100
PubChem Substance ID:
24850658

Assay

97%

form

liquid

refractive index

n20/D 1.4543 (lit.)

bp

75-77 °C/8 mmHg (lit.)

density

0.936 g/mL at 25 °C (lit.)

SMILES string

CC(C)C(N)CO

InChI

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

InChI key

NWYYWIJOWOLJNR-UHFFFAOYSA-N

Application

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

194.0 °F - closed cup

Flash Point(C)

90 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Preparation of homochiral phenolic crown ethers containing para-substituted phenol moiety and chiral subunits derived from (S)-1-phenylethane-1, 2-diol: their chiral recognition behaviour in complexation with neutral amines.
Naemura K, et al.
Tetrahedron Asymmetry, 8(6), 873-882 (1997)
Vincenzo Giulio Albano et al.
The Journal of organic chemistry, 73(21), 8376-8381 (2008-10-02)
1-Allyl-2-pyrroleimines obtained from (S)-valinol and (S)-phenylglycinol underwent highly diastereoselective addition of allylmagnesium chloride, used in excess amounts, to give the corresponding secondary amines with concomitant allyl to (Z)-1-propenyl isomerization of the 1-pyrrole substituent. Transformation of the 2-amino alcohol moiety to
Andrei V Malkov et al.
Chemical communications (Cambridge, England), (15)(15), 1948-1949 (2003-08-23)
New N,P-ligands 4-6, derived from valinol and prolinol, respectively, have been developed for the asymmetric, copper(I)-catalysed conjugate addition of diethylzinc to unsaturated ketones; the tertiary amide group has been shown to effectively relay the chiral information from the ligand backbone
E Spitzer et al.
Biochemistry international, 14(4), 581-588 (1987-04-01)
A procedure for purification of plasma membranes from bovine mammary gland has been developed. The binding capacity of EGF to the plasma membranes from mammary tissue of pregnant cows was equal to 335 fmol per mg of protein thus being
Minoru Tamiya et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 13(35), 9791-9823 (2007-10-02)
A general approach to the regio- and stereoselective total synthesis of the benanomicin-pradimicin antibiotics (BpAs) is described. Construction of the aglycon has been achieved by 1) the diastereoselective ring-opening of a biaryl lactone by using (R)-valinol as a chiral nucleophile
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