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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:
Molecular Weight:
103.16
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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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.)

functional group

amine
hydroxyl

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

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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
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
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)
Birger Dittrich et al.
Acta crystallographica. Section C, Crystal structure communications, 62(Pt 11), o633-o635 (2006-11-08)
The structure of L-valinol [(S)-(+)-2-amino-3-methylbutan-1-ol or hydroxylated L-valine], C5H13NO, has been determined at 100 K by single-crystal X-ray diffraction. The independent atom model geometry, Flack parameter and figures of merit are compared with results from an invariom structure refinement. The
Peter Møller et al.
Mutation research, 527(1-2), 91-97 (2003-06-06)
Earlier studies have indicated that sucrose increases 2-amino-3-methylimidazo[4,5-f]quinoline (IQ)-induced aberrant crypt foci in the colon. In this study, we investigated the role of sucrose in IQ-induced genotoxicity of the colon mucosa and liver. Big Blue rats were fed with IQ

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