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296643

Sigma-Aldrich

(R)-(−)-sec-Butylamine

99%

Synonym(s):

(R)-(−)-2-Aminobutane

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About This Item

Linear Formula:
C2H5CH(NH2)CH3
CAS Number:
13250-12-9
Molecular Weight:
73.14
Beilstein:
1718761
EC Number:
236-232-6
MDL number:
MFCD00064416
UNSPSC Code:
12352116
PubChem Substance ID:
24857863
NACRES:
NA.22
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Quality Level

200

Assay

99%

optical activity

[α]19/D −7.5°, neat

refractive index

n20/D 1.393 (lit.)

bp

63 °C (lit.)

density

0.72 g/mL at 25 °C (lit.)

functional group

amine

SMILES string

CC[C@@H](C)N

InChI

1S/C4H11N/c1-3-4(2)5/h4H,3,5H2,1-2H3/t4-/m1/s1

InChI key

BHRZNVHARXXAHW-SCSAIBSYSA-N

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Application

(R)-(−)-sec-Butylamine can be used:
  • To prepare (R)-(−)-sec-butylbis(2-hydroxyethyl)amine, an intermediate for the synthesis of aminodiphosphine ligands.[1]
  • As a substrate to demonstrate the stereochemistry of Mitsunobu reaction in the synthesis of secondary amines.[2]
  • As a model compound in the study of singlet-triplet transitions in circular dichroism.[3]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1A

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-2.2 °F - closed cup

Flash Point(C)

-19 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2620
BCCK9587
BCCH7421
BCCG7143
BCCF3319

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Butylamine 99.5%

Sigma-Aldrich

471305

Butylamine

Stereospecific synthesis of secondary amines by the Mitsunobu reaction
Edwards ML, et al.
Tetrahedron Letters, 31(24), 3417-3420 (1990)
Detection of singlet-triplet transitions in circular dichroism. A study of 2-aminobutane
Basil A and Gedanken A
Journal of the American Chemical Society, 111(26), 9237-9238 (1989)
Synthesis of the New Chiral (R)-and (S)-Aminodiphosphine Ligands sec-Butylbis (2-(diphenylphosphino) ethyl) amine, sec-Butylbis (2-(dicyclohexylphosphino) ethyl) amine, and (alpha-Methylbenzyl) bis (2-(dicyclohexylphosphino) ethyl) amine and Their Organom
Bianchini C, et al.
Organometallics, 16(20), 4403-4414 (1997)

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