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H10401

Sigma-Aldrich

Hexamethyleneimine

99%

Synonym(s):

1-Azacycloheptane, Azepane, HMI, Perhydroazepine, Hexahydro-1H-azepine, Homopiperidine

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$35.40
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$35.56
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$57.40

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25 ML
$35.40
100 ML
$35.56
500 ML
$57.40

About This Item

Empirical Formula (Hill Notation):
C6H13N
CAS Number:
111-49-9
Molecular Weight:
99.17
Beilstein/REAXYS Number:
1084
EC Number:
203-875-9
MDL number:
MFCD00006934
UNSPSC Code:
12352100
PubChem Substance ID:
24895424
NACRES:
NA.22
form:
liquid
assay:
99%

$35.40

In StockDetails

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vapor pressure

7.4 mmHg ( 21.1 °C)

Quality Level

100

assay

99%

form

liquid

refractive index

n20/D 1.466 (lit.)

bp

138 °C/749 mmHg (lit.)

density

0.88 g/mL at 25 °C (lit.)

SMILES string

C1CCCNCC1

InChI

1S/C6H13N/c1-2-4-6-7-5-3-1/h7H,1-6H2

InChI key

ZSIQJIWKELUFRJ-UHFFFAOYSA-N

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Application

Hexamethyleneimine (HMI) can be used in the preparation of:
  • zeolitic catalysts such as MCM-22 and MCM-49[1][2][3]
  • SAPO-35, a molecular sieve[4][5]
  • various microporous aluminosilicates and titanosilicates[6][7][8]
  • organic-inorganic hybrid pervoskite[9]


It can also been used in the total synthesis of various natural products and bioactive molecules such as (−)-balanol, indole estrogens, derivatives of daunorubicin and (+)-cetiedil.[10][11][12][13]

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Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Inhalation - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1C - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

64.4 °F - closed cup

flash_point_c

18 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV3437
MKCT3570
MKCR7411
MKCS3887
MKCN9751

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Zeolite MCM-49: a three-dimensional MCM-22 analogue synthesized by in situ crystallization.
Lawton SL, et al.
The Journal of Physical Chemistry, 100(9), 3788-3798 (1996)
Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens.
Miller CP, et al.
Journal of Medicinal Chemistry, 44(11), 1654-1657 (2001)
Synthesis of zeolite MCM-22 under rotating and static conditions. Microporous and mesoporous materials.
Guray I, et al.
Microporous and Mesoporous Materials : The Official Journal of the International Zeolite Association, 31(3), 241-251 (1999)
Synthesis of SAPO-35 in non-aqueous gels.
Venkatathri N, et al.
J. Chem. Soc., Faraday Trans., 93(18), 3411-3415 (1997)
Longle Ma et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 22(50), 18179-18189 (2016-10-07)
Cyclic amines such as pyrrolidine and piperidine are known to undergo condensations with aldehydes to furnish pyrrole and pyridine derivatives, respectively. A combined experimental and computational study provides detailed insights into the mechanism of pyrrole formation. A number of reactive
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