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534579

Sigma-Aldrich

(R)-(−)-2-Amino-1-pentanol

97%

Synonym(s):

D-Norvalinol

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About This Item

Linear Formula:
CH3(CH2)2CH(NH2)CH2OH
CAS Number:
80696-30-6
Molecular Weight:
103.16
MDL number:
MFCD02683228
UNSPSC Code:
12352116
PubChem Substance ID:
24878046
NACRES:
NA.22

Assay

97%

optical activity

[α]20/D −17°, c = 1 in chloroform

mp

44-48 °C (lit.)

functional group

amine
hydroxyl

SMILES string

CCC[C@@H](N)CO

InChI

1S/C5H13NO/c1-2-3-5(6)4-7/h5,7H,2-4,6H2,1H3/t5-/m1/s1

InChI key

ULAXUFGARZZKTK-RXMQYKEDSA-N

Application

(R)-(-)-2-Amino-1-pentanol can be used as a chiral building block to prepare:
  • A key intermediate, (R)-N-(p-toluenesulfonyl)-2-propylaziridine, which is utilized in the total synthesis of (R)-1-(benzofuran-2-yl)-2-propylaminopentane.
  • (R)-N-benzyloxycarbonyl-aminoaldehydes as potential substrates for dihydroxyacetone phosphate (DHAP)-dependent aldolases.
  • (R)-2-((2-Aminoquinazolin-4-yl)amino)pentan-1-ol as a potent dual toll-like receptor and modulator.

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

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

204.8 °F - closed cup

Flash Point(C)

96 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK7582
17098MJ
04715CH
11309TD
07024MI

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Dihydroxyacetone phosphate aldolase catalyzed synthesis of structurally diverse polyhydroxylated pyrrolidine derivatives and evaluation of their glycosidase inhibitory properties
Calveras J, et al.
Chemistry?A European Journal , 15(30), 7310-7328 (2009)
2, 4-diaminoquinazolines as dual toll-like receptor (TLR) 7/8 modulators for the treatment of hepatitis B virus
Embrechts W, et al.
Journal of Medicinal Chemistry, 61(14), 6236-6246 (2018)
Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane,((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer
Oka T, et al.
Bioorganic & Medicinal Chemistry, 9(5), 1213-1219 (2001)

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