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20439-47-8

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20439-47-8 Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 20439-47-8 differently. You can refer to the following data:
1. (1R,2R)-(-)-1,2-Diaminocyclohexane can be used as a building block for chiral ligands.
2. suzuki reaction
3. (1R,2R)-(-)-1,2-Diaminocyclohexane is a versatile ligand for the formation of metal complexes. Used in the synthesis of chiral tropocoronands which have potential utility in asymmetric catalysis.

Purification Methods

Distil or recrystallise the diamine from pet ether under N2 or Ar. Store it as above. The 1R,2R-base L-tartrate salt has M 264.3, m 2 7 3o and [ ] D +12.5o (c 4, H2O), and can be used to purfy and/or optically enrich the free base. [Beilstein 13 III 6, and references below.]

Check Digit Verification of cas no

The CAS Registry Mumber 20439-47-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,4,3 and 9 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 20439-47:
(7*2)+(6*0)+(5*4)+(4*3)+(3*9)+(2*4)+(1*7)=88
88 % 10 = 8
So 20439-47-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H14N2/c7-6(8)4-2-1-3-5-6/h1-5,7-8H2

20439-47-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C1447)  (1R,2R)-(-)-1,2-Cyclohexanediamine  >98.0%(GC)(T)

  • 20439-47-8

  • 5g

  • 480.00CNY

  • Detail
  • TCI America

  • (C1447)  (1R,2R)-(-)-1,2-Cyclohexanediamine  >98.0%(GC)(T)

  • 20439-47-8

  • 25g

  • 1,050.00CNY

  • Detail
  • Alfa Aesar

  • (L14059)  (1R,2R)-(-)-1,2-Diaminocyclohexane, 98%   

  • 20439-47-8

  • 250mg

  • 275.0CNY

  • Detail
  • Alfa Aesar

  • (L14059)  (1R,2R)-(-)-1,2-Diaminocyclohexane, 98%   

  • 20439-47-8

  • 1g

  • 728.0CNY

  • Detail
  • Alfa Aesar

  • (L14059)  (1R,2R)-(-)-1,2-Diaminocyclohexane, 98%   

  • 20439-47-8

  • 5g

  • 2431.0CNY

  • Detail
  • Aldrich

  • (346721)  (1R,2R)-(−)-1,2-Diaminocyclohexane  98%

  • 20439-47-8

  • 346721-1G

  • 801.45CNY

  • Detail
  • Aldrich

  • (346721)  (1R,2R)-(−)-1,2-Diaminocyclohexane  98%

  • 20439-47-8

  • 346721-5G

  • 2,610.27CNY

  • Detail

20439-47-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (1R,2R)-(-)-1,2-Diaminocyclohexane

1.2 Other means of identification

Product number -
Other names (1R)-(-)-trans-1,2-Diaminocyclohexane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:20439-47-8 SDS

20439-47-8Synthetic route

(1R,2R)-1,2-diaminocyclohexane tartrate

(1R,2R)-1,2-diaminocyclohexane tartrate

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With sodium hydroxide In water98%
With sodium hydroxide In dichloromethane; water at 20℃; for 0.5h; Inert atmosphere;96%
With potassium hydroxide In water92%
trans-2-azido-N,N-dibenzylcyclohexan-1-amine

trans-2-azido-N,N-dibenzylcyclohexan-1-amine

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 1034.32 Torr; for 60h;97%
((1R,2R)-2-Azido-cyclohexyl)-((R)-1-phenyl-ethyl)-amine
329321-24-6

((1R,2R)-2-Azido-cyclohexyl)-((R)-1-phenyl-ethyl)-amine

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In methanol at 20℃; under 2068.59 Torr; for 48h;95%
D-tartaric acid
147-71-7

D-tartaric acid

A

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

B

(1S,2S)-cyclohexane-1,2-diammonium 2,3-dihydroxysuccinate

(1S,2S)-cyclohexane-1,2-diammonium 2,3-dihydroxysuccinate

Conditions
ConditionsYield
In water at 70℃; Resolution of racemate; optical yield given as %ee;A n/a
B 95%
(1R,2R)-cyclohexane-1,2-diamine (2R,4R)-xylaric acid salt

(1R,2R)-cyclohexane-1,2-diamine (2R,4R)-xylaric acid salt

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With sodium hydroxide In water pH=9;92.9%
C11H13NO6S*C6H14N2

C11H13NO6S*C6H14N2

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With sodium hydroxide In water at -10 - -5℃; for 1h;92%
malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

A

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

B

(S,S)-1,2-diaminocyclohexane
21436-03-3

(S,S)-1,2-diaminocyclohexane

C

N-[(1R,2R)-2-(2-Methoxycarbonyl-acetylamino)-cyclohexyl]-malonamic acid methyl ester
186144-56-9

N-[(1R,2R)-2-(2-Methoxycarbonyl-acetylamino)-cyclohexyl]-malonamic acid methyl ester

D

N-((1R,2R)-2-Amino-cyclohexyl)-malonamic acid methyl ester

N-((1R,2R)-2-Amino-cyclohexyl)-malonamic acid methyl ester

Conditions
ConditionsYield
With Candida antarctica lipase on acrylic resin In 1,4-dioxane at 20℃;A n/a
B n/a
C 48%
D n/a
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With L-Tartaric acid
1,2-diaminocyclohexane
694-83-7

1,2-diaminocyclohexane

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

A

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

B

(S,S)-1,2-diaminocyclohexane
21436-03-3

(S,S)-1,2-diaminocyclohexane

C

N-[(1R,2R)-2-(2-Methoxycarbonyl-acetylamino)-cyclohexyl]-malonamic acid methyl ester
186144-56-9

N-[(1R,2R)-2-(2-Methoxycarbonyl-acetylamino)-cyclohexyl]-malonamic acid methyl ester

Conditions
ConditionsYield
With immobilised Candida antarctica lipase (NOVOZYM 435) In 1,4-dioxane for 7h;
(R,R)-1,2-Diaminocyclohexane (S,S)-cyclohexane-1,2-diol adduct

(R,R)-1,2-Diaminocyclohexane (S,S)-cyclohexane-1,2-diol adduct

A

(1S,2S)-trans-1,2-Cyclohexanediol
57794-08-8

(1S,2S)-trans-1,2-Cyclohexanediol

B

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
In benzene at 24.85℃; Equilibrium constant; Further Variations:; Solvents; dissociation;
(R,R)-1,2-Diaminocyclohexane (R,R)-cyclopentan-1,2-diol adduct

(R,R)-1,2-Diaminocyclohexane (R,R)-cyclopentan-1,2-diol adduct

A

(1R,2R)-cyclopentane-1,2-diol
930-46-1

(1R,2R)-cyclopentane-1,2-diol

B

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
In benzene at 24.85℃; Equilibrium constant; Further Variations:; Solvents; dissociation;
(1R,2R)-Cyclohexane-1,2-diamine; compound with (1S,2S)-cyclopentane-1,2-diol

(1R,2R)-Cyclohexane-1,2-diamine; compound with (1S,2S)-cyclopentane-1,2-diol

A

(S,S)-cyclopentane-1,2-diol
63261-45-0

(S,S)-cyclopentane-1,2-diol

B

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
In benzene at 24.85℃; Equilibrium constant; Further Variations:; Solvents; dissociation;
(R,R)-1,2-Diaminocyclohexane (R,R)-cyclohexane-1,2-diol adduct

(R,R)-1,2-Diaminocyclohexane (R,R)-cyclohexane-1,2-diol adduct

B

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
In benzene at 24.85℃; Equilibrium constant; Further Variations:; Solvents; dissociation;
(1R,2R)-(-)-1,2-diammoniumcyclohexane mono-L-(+)-tartrate
116407-32-0

(1R,2R)-(-)-1,2-diammoniumcyclohexane mono-L-(+)-tartrate

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With potassium carbonate In ethanol at 70 - 80℃; for 2h;
With potassium carbonate In ethanol; water for 2h; Reflux;

A

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

B

(S,S)-1,2-diaminocyclohexane
21436-03-3

(S,S)-1,2-diaminocyclohexane

Conditions
ConditionsYield
Stage #1: trans-1,2-Diaminocyclohexane With L-Tartaric acid; acetic acid In methanol; water for 24h; Heating;
Stage #2: With hydrogenchloride In acetone for 25h; Heating;
Stage #3: With sodium hydroxide
Resolution of racemate;
Stage #1: trans-1,2-Diaminocyclohexane With L-Tartaric acid In water at 70℃; for 2.5h; Resolution of racemate;
Stage #2: With acetic acid In water for 2h;
With C36H36N2O10 In methanol; diethyl ether at 10℃; for 0.5h; pH=4.5; Concentration; Solvent; Temperature; Time; pH-value; Resolution of racemate; enantioselective reaction;
1,2-diaminocyclohexane
694-83-7

1,2-diaminocyclohexane

A

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

B

(S,S)-1,2-diaminocyclohexane
21436-03-3

(S,S)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With (1S,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid In methanol
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

(1S)-2-amino-cyclohexanol-(1)

(1S)-2-amino-cyclohexanol-(1)

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / LiClO4 / acetonitrile / 48 h / 20 °C
2: 75 percent / diisopropyl azodicarboxylate; Ph3P / CH2Cl2 / 7 h / 0 - 20 °C
3: TMSN3 / acetonitrile / 7 h / 20 °C
4: 95 percent / H2 / Pd(OH)2/C / methanol / 48 h / 20 °C / 2068.59 Torr
View Scheme
7-((R)-1-Phenyl-ethyl)-7-aza-bicyclo[4.1.0]heptane
329321-23-5

7-((R)-1-Phenyl-ethyl)-7-aza-bicyclo[4.1.0]heptane

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TMSN3 / acetonitrile / 7 h / 20 °C
2: 95 percent / H2 / Pd(OH)2/C / methanol / 48 h / 20 °C / 2068.59 Torr
View Scheme
2-((R)-1-Phenyl-ethylamino)-cyclohexanol
329321-22-4

2-((R)-1-Phenyl-ethylamino)-cyclohexanol

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 75 percent / diisopropyl azodicarboxylate; Ph3P / CH2Cl2 / 7 h / 0 - 20 °C
2: TMSN3 / acetonitrile / 7 h / 20 °C
3: 95 percent / H2 / Pd(OH)2/C / methanol / 48 h / 20 °C / 2068.59 Torr
View Scheme
1,2-cyclohexanedionedioxime
492-99-9

1,2-cyclohexanedionedioxime

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol; sodium
2: Lg-tartaric acid
View Scheme
trans-1,2-diazidocyclohexane

trans-1,2-diazidocyclohexane

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Pd-C
View Scheme
cyclohexene
110-83-8

cyclohexene

/PBNAI150--221/

/PBNAI150--221/

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) Fe2(SO4)3, NaN3, MeOH, (ii) H2O2, MeOH
2: H2 / Pd-C
View Scheme
1,2-diaminocyclohexane
694-83-7

1,2-diaminocyclohexane

A

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

B

cis-cyclohexane-1,2-diamine
1436-59-5

cis-cyclohexane-1,2-diamine

C

(S,S)-1,2-diaminocyclohexane
21436-03-3

(S,S)-1,2-diaminocyclohexane

Conditions
ConditionsYield
separation by salt formation with (+)-L-tartaric acid;A 2.0 g
B n/a
C 0.9 g
trans-1,2-cyclohexanediamine

trans-1,2-cyclohexanediamine

A

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

B

(S,S)-1,2-diaminocyclohexane
21436-03-3

(S,S)-1,2-diaminocyclohexane

Conditions
ConditionsYield
Stage #1: With titanium(IV) isopropylate; (R,R)-TADDOL In diphenylether at 90℃; for 1h;
Stage #2: trans-1,2-cyclohexanediamine In diphenylether at 90℃; for 0.166667h; Product distribution / selectivity;
A n/a
B n/a
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With sodium hydroxide
trans-1,2-(R,R)-diammoniumcyclohexane tartrate

trans-1,2-(R,R)-diammoniumcyclohexane tartrate

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With triethylamine; sodium hydroxide In dichloromethane at 0℃; for 0.166667h;
(R,R)-1,2-diaminocyclohexane tartrate

(R,R)-1,2-diaminocyclohexane tartrate

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With potassium hydroxide In dichloromethane at 20℃;
C6H14N2*C6H10O4

C6H14N2*C6H10O4

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
With potassium carbonate In water at 20℃;
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

benzaldehyde
100-52-7

benzaldehyde

(1R,2R)-N,N'-dibenzylidene-1,2-diaminocyclohexane
199180-98-8

(1R,2R)-N,N'-dibenzylidene-1,2-diaminocyclohexane

Conditions
ConditionsYield
100%
With 3 A molecular sieve In dichloromethane for 12h;91%
90%
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

acetic anhydride
108-24-7

acetic anhydride

trans-Diacetamido-(1R,2R)-(-)-1,2-cyclohexane
156257-14-6

trans-Diacetamido-(1R,2R)-(-)-1,2-cyclohexane

Conditions
ConditionsYield
In chloroform for 1h;100%
With In(OSO2CF3)3 In acetonitrile at 20℃; Acetylation;91%
In methanol for 4h; Ambient temperature;73%
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

N-methylmitomycin A
18209-14-8

N-methylmitomycin A

C22H29N5O4
364753-62-8

C22H29N5O4

Conditions
ConditionsYield
In methanol at 20℃; for 24h;100%
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

benzaldehyde
100-52-7

benzaldehyde

(1R,2R)-N,N'-dibenzylcyclohexane-1,2-diamine
65838-10-0, 135613-88-6, 143443-23-6

(1R,2R)-N,N'-dibenzylcyclohexane-1,2-diamine

Conditions
ConditionsYield
Stage #1: (1R,2R)-1,2-diaminocyclohexane; benzaldehyde In methanol for 0.5h; Heating;
Stage #2: With sodium tetrahydroborate In methanol for 0.25h; Heating;
100%
Stage #1: (1R,2R)-1,2-diaminocyclohexane; benzaldehyde
Stage #2: With sodium tetrahydroborate In methanol
98%
Stage #1: (1R,2R)-1,2-diaminocyclohexane; benzaldehyde In methanol at 70℃; for 6h;
Stage #2: With sodium tetrahydroborate In methanol at 20 - 70℃; for 4h;
Stage #3: With hydrogenchloride; sodium hydroxide; water more than 3 stages;
93%
3,5-di-tert-butyl-2-hydroxybenzaldehyde
37942-07-7

3,5-di-tert-butyl-2-hydroxybenzaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine
135616-40-9

(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

Conditions
ConditionsYield
In ethanol for 1h; Heating;100%
With formic acid In methanol at 20℃;88%
2,6-Pyridinedicarboxaldehyde
5431-44-7

2,6-Pyridinedicarboxaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(CH2C5H3NCH2HNC6H10NH)3*6HCl

(CH2C5H3NCH2HNC6H10NH)3*6HCl

Conditions
ConditionsYield
Stage #1: 2,6-Pyridinedicarboxaldehyde; (1R,2R)-1,2-diaminocyclohexane With barium(II) chloride In methanol for 25h;
Stage #2: With sodium tetrahydroborate In methanol for 7h;
Stage #3: With hydrogenchloride In methanol at 0℃; Further stages.;
100%
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

p-phenylenedioxydiacetic acid di-(3-tert-butyl-5-formyl-4-hydroxy-phenyl)ester
616873-78-0

p-phenylenedioxydiacetic acid di-(3-tert-butyl-5-formyl-4-hydroxy-phenyl)ester

1,3,5-benzenetrioxytriacetic acid tri-(3-tert-butyl-5-formyl-4-hydroxy-phenyl)ester
616873-79-1

1,3,5-benzenetrioxytriacetic acid tri-(3-tert-butyl-5-formyl-4-hydroxy-phenyl)ester

polymer, triester/diester w/w feed ratio 0.5/100; monomer(s): 1,3,5-benzenetrioxytriacetic acid tri-(3-tert-butyl-5-formyl-4-hydroxyphenyl)ester; p-phenylenedioxydiacetic acid di-(3-tert-butyl-5-formyl-4-hydroxyphenyl)ester; (R,R)-1,2-diaminocyclohexane

polymer, triester/diester w/w feed ratio 0.5/100; monomer(s): 1,3,5-benzenetrioxytriacetic acid tri-(3-tert-butyl-5-formyl-4-hydroxyphenyl)ester; p-phenylenedioxydiacetic acid di-(3-tert-butyl-5-formyl-4-hydroxyphenyl)ester; (R,R)-1,2-diaminocyclohexane

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Heating;100%
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(4-methoxy-phenoxy)-acetic acid 3-tert-butyl-5-formyl-4-hydroxy-phenyl ester
805314-84-5

(4-methoxy-phenoxy)-acetic acid 3-tert-butyl-5-formyl-4-hydroxy-phenyl ester

(4-Methoxy-phenoxy)-acetic acid 3-tert-butyl-5-[((E)-(1R,2R)-2-{[1-{3-tert-butyl-2-hydroxy-5-[2-(4-methoxy-phenoxy)-acetoxy]-phenyl}-meth-(E)-ylidene]-amino}-cyclohexylimino)-methyl]-4-hydroxy-phenyl ester

(4-Methoxy-phenoxy)-acetic acid 3-tert-butyl-5-[((E)-(1R,2R)-2-{[1-{3-tert-butyl-2-hydroxy-5-[2-(4-methoxy-phenoxy)-acetoxy]-phenyl}-meth-(E)-ylidene]-amino}-cyclohexylimino)-methyl]-4-hydroxy-phenyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Heating;100%
5-tert-butyl-3-[(N,N-dimethylamino)methyl]-2-hydroxybenzaldehyde
478282-20-1

5-tert-butyl-3-[(N,N-dimethylamino)methyl]-2-hydroxybenzaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

C34H52N4O2

C34H52N4O2

Conditions
ConditionsYield
In ethanol at 20℃; for 24h;100%
In ethanol at 20℃; for 24h;
5-tert-butyl-2-hydroxy-3-(pyrrolidin-1-ylmethyl)benzaldehyde

5-tert-butyl-2-hydroxy-3-(pyrrolidin-1-ylmethyl)benzaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

C38H56N4O2

C38H56N4O2

Conditions
ConditionsYield
In ethanol at 20℃; for 24h;100%
In ethanol at 20℃; for 24h;
5-tert-butyl-2-hydroxy-3-quinolin-8-yl-benzaldehyde

5-tert-butyl-2-hydroxy-3-quinolin-8-yl-benzaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(-)-(R,R)-cyclohexanediamine-(p-tert-butyl)-(quinolin-8-yl)-salen

(-)-(R,R)-cyclohexanediamine-(p-tert-butyl)-(quinolin-8-yl)-salen

Conditions
ConditionsYield
In ethanol at 20℃; for 6h;100%
In ethanol at 20℃; for 24h;100%
(R)-5-tert-butyl-2-hydroxy-3-{[methyl-(1-phenyl-ethyl)-amino]-methyl}-benzaldehyde
478555-34-9

(R)-5-tert-butyl-2-hydroxy-3-{[methyl-(1-phenyl-ethyl)-amino]-methyl}-benzaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

C48H64N4O2

C48H64N4O2

Conditions
ConditionsYield
In ethanol at 20℃; for 24h;100%
In ethanol at 20℃; for 24h;
(S)-5-tert-butyl-2-hydroxy-3-(2-methoxymethyl-pyrrolidin-1-ylmethyl)-benzaldehyde
478555-35-0

(S)-5-tert-butyl-2-hydroxy-3-(2-methoxymethyl-pyrrolidin-1-ylmethyl)-benzaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

C42H64N4O4

C42H64N4O4

Conditions
ConditionsYield
In ethanol at 20℃; for 24h;100%
In ethanol at 20℃; for 24h;
2,6-dichloro-heptanedioic acid bis-(3-tert-butyl-5-formyl-4-hydroxy-phenyl) ester
336195-59-6

2,6-dichloro-heptanedioic acid bis-(3-tert-butyl-5-formyl-4-hydroxy-phenyl) ester

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

C70H88Cl4N4O12

C70H88Cl4N4O12

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2h;100%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(1R,2R)-N,N'-bis(thiophen-2-ylmethylene)cyclohexane-1,2-diamine
630402-57-2

(1R,2R)-N,N'-bis(thiophen-2-ylmethylene)cyclohexane-1,2-diamine

Conditions
ConditionsYield
100%
With magnesium sulfate In chlorobenzene at 100℃; for 0.333333h; microwave irradiation;91%
4-[2,7-di-tert-butyl-5-(3-tert-butyl-5-formyl-4-hydroxyphenyl)-9,9-dimethyl-9H-xanthen-4-yl]benzoic acid methyl ester
945629-73-2

4-[2,7-di-tert-butyl-5-(3-tert-butyl-5-formyl-4-hydroxyphenyl)-9,9-dimethyl-9H-xanthen-4-yl]benzoic acid methyl ester

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

H2[HphSX*t-Bu-COOMe]

H2[HphSX*t-Bu-COOMe]

Conditions
ConditionsYield
In ethanol for 12h; Heating;100%
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

methyltrioxorhenium(VII)
70197-13-6

methyltrioxorhenium(VII)

methyltrioxorhenium(VII)/(1R,2R)-1,2-diaminocyclohexane adduct

methyltrioxorhenium(VII)/(1R,2R)-1,2-diaminocyclohexane adduct

Conditions
ConditionsYield
In toluene equimolar organic ligand added to Re-compound in toluene at room temp.; filtrated; washed with n-hexane; elem. anal.;100%
benzene-1,3,5-trialdehyde
3163-76-6

benzene-1,3,5-trialdehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

CC3-R

CC3-R

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h;100%
With trifluoroacetic acid In dichloromethane at 20℃; for 120h;83%
With trifluoroacetic acid In dichloromethane at 20℃;83%
With trifluoroacetic acid In dichloromethane at 20℃;83%
In dichloromethane at 20℃;70%
3-tert-butyl-2-hydroxy-5-((6-oxo-1,6-dihydropyridin-2-yl)ethynyl)benzaldehyde
1092119-19-1

3-tert-butyl-2-hydroxy-5-((6-oxo-1,6-dihydropyridin-2-yl)ethynyl)benzaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

6,6'-(5,5'-(1E,1'E)-(1R,2R)-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)bis(3-tert-butyl-4-hydroxy-5,1-phenylene)bis(ethyne-2,1-diyl))dipyridin-2(1H)-one

6,6'-(5,5'-(1E,1'E)-(1R,2R)-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)bis(3-tert-butyl-4-hydroxy-5,1-phenylene)bis(ethyne-2,1-diyl))dipyridin-2(1H)-one

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;100%
2-Hydroxy-4-methoxybenzaldehyde
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

N,N'-bis(4-methoxysalicylidene)-(R,R')-1,2-cyclohexanediamine

N,N'-bis(4-methoxysalicylidene)-(R,R')-1,2-cyclohexanediamine

Conditions
ConditionsYield
In methanol100%
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

3,5-bistrifluoromethylphenylisothiocyanate
23165-29-9

3,5-bistrifluoromethylphenylisothiocyanate

(1R,2R)-1,2-bis[N-(3,5-bis(trifluoromethyl)phenyl)thiourea]cyclohexane

(1R,2R)-1,2-bis[N-(3,5-bis(trifluoromethyl)phenyl)thiourea]cyclohexane

Conditions
ConditionsYield
In methanol for 0.333333h;100%
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

p-nitrophenyl isothiocyanate
2131-61-5

p-nitrophenyl isothiocyanate

(1R,2R)-1,2-bis[N-(4-nitrophenyl)thiourea]cyclohexane
1402216-64-1

(1R,2R)-1,2-bis[N-(4-nitrophenyl)thiourea]cyclohexane

Conditions
ConditionsYield
for 0.5h; neat (no solvent);100%
1-(5-tert-butyl-3-formyl-2-hydroxybenzyl)pyridinium bromide
1057558-12-9

1-(5-tert-butyl-3-formyl-2-hydroxybenzyl)pyridinium bromide

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(R,R)-(-)-N,N'-bis(3-tert-butyl-5-(pyridinium-1-ylmethyl)salicylidene)-1,2-cyclohexanediamine dibromide

(R,R)-(-)-N,N'-bis(3-tert-butyl-5-(pyridinium-1-ylmethyl)salicylidene)-1,2-cyclohexanediamine dibromide

Conditions
ConditionsYield
In ethanol at 20℃; for 15h; Molecular sieve;100%
3-(5-tert-butyl-3-formyl-2-hydroxybenzyl)-1-mesityl-1H-imidazol-3-ium chloride
1416171-26-0

3-(5-tert-butyl-3-formyl-2-hydroxybenzyl)-1-mesityl-1H-imidazol-3-ium chloride

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(R,R)-(-)-N,N′-bis(5-tert-butyl-3-((1-mesityl-1H-imidazol-3-ium)-3-ylmethyl)salicylidene)-1,2-cyclohexanediamine dichloride

(R,R)-(-)-N,N′-bis(5-tert-butyl-3-((1-mesityl-1H-imidazol-3-ium)-3-ylmethyl)salicylidene)-1,2-cyclohexanediamine dichloride

Conditions
ConditionsYield
In ethanol at 20℃; for 20h; Inert atmosphere; Molecular sieve;100%
3-(5-tert-butyl-3-formyl-2-hydroxybenzyl)-1-methyl-1H-benzo[d]imidazol-3-ium chloride
1416171-27-1

3-(5-tert-butyl-3-formyl-2-hydroxybenzyl)-1-methyl-1H-benzo[d]imidazol-3-ium chloride

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(R,R)-(-)-N,N′-bis(5-tert-butyl-3-((1-methyl-1H-benzo[d]imidazol-3-ium)-3-ylmethyl)salicylidene)-1,2-cyclohexanediamine dichloride

(R,R)-(-)-N,N′-bis(5-tert-butyl-3-((1-methyl-1H-benzo[d]imidazol-3-ium)-3-ylmethyl)salicylidene)-1,2-cyclohexanediamine dichloride

Conditions
ConditionsYield
In ethanol at 20℃; for 20h; Inert atmosphere; Molecular sieve;100%
3-(5-(tert-butyl)-3-formyl-2-hydroxybenzyl)-1-methyl-1H-imidazol-3-ium chloride
1416171-24-8

3-(5-(tert-butyl)-3-formyl-2-hydroxybenzyl)-1-methyl-1H-imidazol-3-ium chloride

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(R,R)-(-)-N,N′-bis(5-tert-butyl-3-((1-methyl-1H-imidazol-3-ium)-3-ylmethyl)salicylidene)-1,2-cyclohexanediamine dichloride

(R,R)-(-)-N,N′-bis(5-tert-butyl-3-((1-methyl-1H-imidazol-3-ium)-3-ylmethyl)salicylidene)-1,2-cyclohexanediamine dichloride

Conditions
ConditionsYield
In ethanol at 20℃; for 20h; Inert atmosphere; Molecular sieve;100%
3-(5-tert-butyl-3-formyl-2-hydroxybenzyl)-1-phenyl-1H-imidazol-3-ium chloride
1416171-25-9

3-(5-tert-butyl-3-formyl-2-hydroxybenzyl)-1-phenyl-1H-imidazol-3-ium chloride

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(R,R)-(-)-N,N′-bis(5-tert-butyl-3-((1-phenyl-1H-imidazol-3-ium)-3-ylmethyl)salicylidene)-1,2-cyclohexanediamine dichloride

(R,R)-(-)-N,N′-bis(5-tert-butyl-3-((1-phenyl-1H-imidazol-3-ium)-3-ylmethyl)salicylidene)-1,2-cyclohexanediamine dichloride

Conditions
ConditionsYield
In ethanol at 20℃; for 20h; Inert atmosphere; Molecular sieve;100%
(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

2-(cyclohexylsulfanyl)benzaldehyde
503065-08-5

2-(cyclohexylsulfanyl)benzaldehyde

(1R,2R)-N,N'-bis(2-(cyclohexylthio)benzylidene)-1,2-cyclohexanediamine
1383611-02-6

(1R,2R)-N,N'-bis(2-(cyclohexylthio)benzylidene)-1,2-cyclohexanediamine

Conditions
ConditionsYield
In ethanol at 80℃;100%
2-(isopropylsulfanyl)benzenecarbaldehyde
53606-32-9

2-(isopropylsulfanyl)benzenecarbaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(1R,2R)-N,N'-bis(2-(isopropylthio)benzylidene)-1,2-cyclohexanediamine
1383610-96-5

(1R,2R)-N,N'-bis(2-(isopropylthio)benzylidene)-1,2-cyclohexanediamine

Conditions
ConditionsYield
In ethanol at 80℃;100%
4-(tert-butyl)-2-(tert-butylthio)benzaldehyde
1383612-01-8

4-(tert-butyl)-2-(tert-butylthio)benzaldehyde

(1R,2R)-1,2-diaminocyclohexane
20439-47-8

(1R,2R)-1,2-diaminocyclohexane

(1R,2R)-N,N-bis[4-(tert-butyl)-2-(tert-butylthio)benzylidene]-1,2-cyclohexanediamine
1383611-42-4

(1R,2R)-N,N-bis[4-(tert-butyl)-2-(tert-butylthio)benzylidene]-1,2-cyclohexanediamine

Conditions
ConditionsYield
In ethanol at 80℃;100%

20439-47-8Relevant articles and documents

Chiral redox-Active isosceles triangles

Nalluri, Siva Krishna Mohan,Liu, Zhichang,Wu, Yilei,Hermann, Keith R.,Samanta, Avik,Kim, Dong Jun,Krzyaniak, Matthew D.,Wasielewski, Michael R.,Stoddart, J. Fraser

, p. 5968 - 5977 (2016)

Designing small-molecule organic redox-active materials, with potential applications in energy storage, has received considerable interest of late. Herein, we report on the synthesis, characterization, and application of two rigid chiral triangles, each of which consist of non-identical pyromellitic diimide (PMDI) and naphthalene diimide (NDI)-based redox-active units. 1H and 13C NMR spectroscopic investigations in solution confirm the lower symmetry (C2 point group) associated with these two isosceles triangles. Single-crystal X-ray diffraction analyses reveal their rigid triangular prism-like geometries. Unlike previously investigated equilateral triangle containing three identical NDI subunits, both isosceles triangles do not choose to form one-dimensional supramolecular nanotubes by dint of [C-H···O] interaction-driven columnar stacking. The rigid isosceles triangle, composed of one NDI and two PMDI subunits, forms in the presence of N,N-dimethylformamidetwo different types of intermolecular NDI-NDI and NDI-PMDI stacked dimers with opposite helicities in the solid state. Cyclic voltammetry reveals that both isosceles triangles can accept reversibly up to six electrons. Continuous-wave electron paramagnetic resonance and electron-nuclear double-resonance spectroscopic investigations, supported by density functional theory calculations, on the single-electron reduced radical anions of the isosceles triangles confirm the selective sharing of unpaired electrons among adjacent redox-active NDI subunit(s) within both molecules. The isosceles triangles have been employed as electrode-active materials in organic rechargeable lithium-ion batteries. The evaluation of the structure-performance relationships of this series of diimide-based triangles reveals that the increase in the number of NDI subunits, replacing PMDI ones, within the molecules improves the electrochemical cell performance of the batteries.

Pd-Catalyzed asymmetric allylation involving bis(diamidophosphite) based on the salen-type chiral diamine

Gavrilov,Chuchelkin,Gavrilov,Zheglov,Firsin,Trunina,Maximychev,Perepukhov

, p. 336 - 339 (2021)

New bis(diamidophosphite) ligand with stereogenic phosphorus atoms in the 1,3,2-diaza-phospholidine rings was synthesized based on (1R,2R)-[N, N′-bis(3-hydroxybenzylidene)]-1,2-diaminocyclohexane. This ligand provided up to 73% ee in Pd-catalyzed asymmetric allylic alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate and up to 80% ee in its amination with pyrrolidine, with the starting substrate conversion being quantitative.

Spectroscopic exploration of binding of new imidazolium-based palladium(II) saldach complexes with CT-DNA as anticancer agents against HER2/neu overexpression

Alfaifi, Mohammad Y.,Elbehairi, Serag Eldin I.,Hafez, Hani S.,Elshaarawy, Reda F.M.

, p. 118 - 128 (2019)

The HER2/neu has shown a potential role in the choice of active chemotherapy for breast tumors because of its prognostic relevance and putative role in predicting drug resistance. Moreover, suppressing DNA replication has become an attractive strategy for treating cancer patients. In this attempt, the present study aimed to prepare new series of bis-imidazolium-based saldach {H2(Et)2saldach (nBu-Im+-X–)2} and their cis-Pd(II) complexes (saldach = N,N′-bis-(salicylidene)-R,R-1,2-diaminocyclohexane; X = Cl, PF6, BF4) as anticancer agents. The in vitro cytotoxicity activity of new cis-Pd(II) complexes against human breast adenocarcinoma cell lines (MCF-7) revealed higher growth-inhibitory effect than the native ligands. They induced a significant decrease for the protein HER2/neu expression with p 50 = 8.5 ± 0.2 μM) in inhibition of cell proliferation. Additionally, in vitro studies of Pd(II) complex (5a) using UV–Vis spectroscopy and binding affinity toward the calf thymus (CT) DNA) showed a combination of covalent, intercalation, hydrogen bonding interactions through formation of (CT-DNA).

Design and synthesis of cage-like NADH model molecule intermediate with multi-chiral centers

Zhang, Tong,Bai, Cui-Bing,Wu, Yue-Hua,Wang, Nai-Xing,Xu, Bao-Cai,Yan, Zhan,Xing, Yalan

, p. 410 - 416 (2019/02/05)

Studying NADH molecules is one of the most active areas in biomimetic research. It is important to design novel and efficient chiral NADH model molecules. Herein, a cage-like NADH model with multi-chiral centers was designed, and key intermediates have been synthesized. In this study, we found that pentafluorophenoxy group is an excellent leaving group for our synthetic route.

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