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MilliporeSigma

270016

(±)-trans-1,2-Diaminocyclohexane

99%

Synonym(s):

(±)-trans-1,2-Cyclohexanediamine

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10 ML

$39.80

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$131.00

250 ML

$633.00

$39.80


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About This Item

Linear Formula:
C6H10(NH2)2
CAS Number:
Molecular Weight:
114.19
Beilstein/REAXYS Number:
3193807
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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vapor pressure

0.4 mmHg ( 20 °C)

assay

99%

form

liquid

refractive index

n20/D 1.489 (lit.)

bp

79-81 °C/15 mmHg (lit.)

mp

14-15 °C (lit.)

density

0.951 g/mL at 25 °C (lit.)

SMILES string

N[C@@H]1CCCC[C@H]1N

InChI

1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2/t5-,6-/m1/s1

InChI key

SSJXIUAHEKJCMH-PHDIDXHHSA-N

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1 of 4

This Item
32851141712D62209
assay

99%

assay

≥98.0% (GC)

assay

98%

assay

98%

Quality Level

200

Quality Level

-

Quality Level

100

Quality Level

100

bp

79-81 °C/15 mmHg (lit.)

bp

197 °C (lit.)

bp

-

bp

48 °C (lit.)

form

liquid

form

-

form

solid

form

liquid

refractive index

n20/D 1.489 (lit.)

refractive index

-

refractive index

-

refractive index

n20/D 1.446 (lit.)

mp

14-15 °C (lit.)

mp

68-72 °C (lit.)

mp

101-104 °C (lit.)

mp

−50 °C (lit.)

General description

(±)-trans-1,2-Diaminocyclohexane is widely used as a ligand in coordination chemistry and organocatalysis. It also serves as an achiral ligand in asymmetric catalysis.[1][2] (±)-trans-1,2-Diaminocyclohexane was condensed with aliphatic dialdehydes to form [3+3] or [2+2] macrocyclization products[3].

Application

(±)-trans-1,2-Diaminocyclohexane was used in the synthesis of macrocyclic [3+3] hexa Schiff base[4]. It was also employed in the synthesis of multidentate ligands[5], chiral auxiliaries[6] and chiral stationary phases[7].

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

156.2 °F - closed cup

flash_point_c

69 °C - closed cup

ppe

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


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Chirality, 4, 447-447 (1992)
trans-1, 2-Diaminocyclohexane derivatives as chiral reagents, scaffolds, and ligands for catalysis: applications in asymmetric synthesis and molecular recognition
YL Bennani, et al.
Chemical Reviews, 97, 3161-3196 null
Tetrahedron, 49, 4419-4419 (1993)
Enantiopure Monoprotected cis-1, 2-Diaminocyclohexane: One-Step Preparation and Application in Asymmetric Organocatalysis
A Berkessel, et al
ChemCatChem, 2, 1215-1218 (2010)
Jana Hodacová et al.
Organic letters, 9(26), 5641-5643 (2007-11-22)
2,2'-Bipyridine-5,5'-dicarbaldehyde has been prepared in two steps by enamination of 5,5'-dimethyl-2,2'-bipyridine with Bredereck's reagent, and subsequent oxidative cleavage of the enamine groups with sodium periodate. On condensation of this dialdehyde with enantiomerically pure trans-1,2-diaminocyclohexane, the macrocyclic [3+3] hexa Schiff base

Questions

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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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