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Merck
CN

281573

(S)-(−)-1-Amino-2-(methoxymethyl)pyrrolidine

95%

Synonym(s):

SAMP

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About This Item

Empirical Formula (Hill Notation):
C6H14N2O
CAS Number:
59983-39-0
Molecular Weight:
130.19
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24856982
MDL number:
MFCD00064485
Beilstein/REAXYS Number:
1523794

Key Documents

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Product Name

(S)-(−)-1-Amino-2-(methoxymethyl)pyrrolidine, 95%

InChI

1S/C6H14N2O/c1-9-5-6-3-2-4-8(6)7/h6H,2-5,7H2,1H3/t6-/m0/s1

SMILES string

COC[C@@H]1CCCN1N

InChI key

BWSIKGOGLDNQBZ-LURJTMIESA-N

assay

95%

form

liquid

optical activity

[α]20/D −79°, neat

optical purity

ee: 97% (GLC)

refractive index

n20/D 1.465 (lit.)

bp

42 °C/1.8 mmHg (lit.)

density

0.97 g/mL at 25 °C (lit.)

functional group

ether

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Application

(S)-(-)-1-Amino-2-(methoxymethyl)pyrrolidine may be used as a chiral auxiliary in the asymmetric synthesis of (S)-2-ethylhexanoic acid and (S)-2-n-propyl-4-pentenoic acid. It can undergo 1,4-addition to (E)-alkenyl-cyclohexyl sulfonates in the presence of zinc bromide to form β-hydrazino-cyclohexyl sulfonates.
Undergoes condensation reactions with carbonyl compounds to produce hydrazones which are useful synthons in highly enantioselective syntheses.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

161.6 °F - closed cup

flash_point_c

72 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG8108
BCBZ5445
BCBV1051
BCBN8045V
BCBK4230V

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Yuanxia Qin et al.
Journal of agricultural and food chemistry, 67(11), 3168-3178 (2019-02-26)
In this study we report a secretory protein that was purified from Serratia marcescens strain S3 isolated from soil from the tobacco rhizosphere. Subsequent mass spectrometry and annotation characterized the protein as secretory alkaline metalloprotease (SAMP). SAMP plays a crucial
Synlett, 897-897 (1992)
Loris R Lopetuso et al.
Inflammatory bowel diseases, 23(3), 392-403 (2017-02-02)
A large body of evidence supports a central role of TLR5 and its natural ligand, flagellin, in Crohn's disease (CD), with the precise mechanism(s) still unresolved. We investigated the role of flagellin/TLR5 in SAMP1/YitFc (SAMP) mice, a spontaneous model of
Luca Di Martino et al.
Cellular and molecular gastroenterology and hepatology, 8(3), 427-446 (2019-06-11)
Crohn's disease (CD) is a debilitating inflammatory disorder that affects more than 1.6 million people in North America alone. Members of the tumor necrosis factor superfamily are key regulators of intestinal inflammation; specifically, tumor necrosis factor-like weak inducer of apoptosis
Asymmetric synthesis and enantioselective teratogenicity of 2-n-propyl-4-pentenoic acid (4-en-VPA), an active metabolite of the anticonvulsant drug, valproic acid.
Hauck R-S and Nau H.
Toxicology Letters, 49(1), 41-48 (1989)
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