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N-[1-(AMINOMETHYL)CYCLOHEXYL]-N,N-DIMETHYLAMINE, a chemical compound with the molecular formula C10H21N2, is often utilized in the field of chemistry for a variety of reactions and processes. This liquid at room temperature is characterized by its amine group (NH2) and cyclohexyl group, which contribute to its stability and reactivity. Its role as a catalyst in organic synthesis is particularly noteworthy, as it helps in facilitating quicker and more efficient reactions. Due to its potential corrosive nature, special care should be taken when handling this substance.

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  • 41806-09-1 Structure
  • Basic information

    1. Product Name: N-[1-(AMINOMETHYL)CYCLOHEXYL]-N,N-DIMETHYLAMINE
    2. Synonyms: [1-(aminomethyl)cyclohexyl]dimethylamine dihydrochloride;1-(aminomethyl)-N,N-dimethylcyclohexanamine;1-(aminomethyl)-N,N-dimethylcyclohexanamine(SALTDATA: 2HCl);1-(Dimethylamino)cyclohexanemethylamine
    3. CAS NO:41806-09-1
    4. Molecular Formula: C9H20N2
    5. Molecular Weight: 156.27
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 41806-09-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 189℃
    3. Flash Point: 69℃
    4. Appearance: /
    5. Density: 0.92
    6. Vapor Pressure: 0.572mmHg at 25°C
    7. Refractive Index: 1.491
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: N-[1-(AMINOMETHYL)CYCLOHEXYL]-N,N-DIMETHYLAMINE(CAS DataBase Reference)
    11. NIST Chemistry Reference: N-[1-(AMINOMETHYL)CYCLOHEXYL]-N,N-DIMETHYLAMINE(41806-09-1)
    12. EPA Substance Registry System: N-[1-(AMINOMETHYL)CYCLOHEXYL]-N,N-DIMETHYLAMINE(41806-09-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 41806-09-1(Hazardous Substances Data)

41806-09-1 Usage

Uses

Used in Chemical Synthesis:
N-[1-(AMINOMETHYL)CYCLOHEXYL]-N,N-DIMETHYLAMINE is used as a catalyst in chemical synthesis for its ability to accelerate and enhance the efficiency of various reactions.
Used in Research and Development:
In the field of research and development, N-[1-(AMINOMETHYL)CYCLOHEXYL]-N,N-DIMETHYLAMINE is used as a reagent to aid in the production and study of other chemical compounds, thanks to its stability and reactivity.
Used in Industrial Production:
N-[1-(AMINOMETHYL)CYCLOHEXYL]-N,N-DIMETHYLAMINE is employed in industrial production as a catalyst to improve the speed and efficiency of chemical processes, contributing to the manufacturing of a wide range of products.

Check Digit Verification of cas no

The CAS Registry Mumber 41806-09-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,8,0 and 6 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 41806-09:
(7*4)+(6*1)+(5*8)+(4*0)+(3*6)+(2*0)+(1*9)=101
101 % 10 = 1
So 41806-09-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H20N2/c1-11(2)9(8-10)6-4-3-5-7-9/h3-8,10H2,1-2H3

41806-09-1Synthetic route

1-(dimethylamino)cyclohexanecarbonitrile
16499-30-2

1-(dimethylamino)cyclohexanecarbonitrile

1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether; water at 20℃;92.5%
With lithium aluminium tetrahydride; sulfuric acid In tetrahydrofuran at 40 - 50℃; for 1h;66%
With lithium aluminium tetrahydride; sulfuric acid In tetrahydrofuran at 0 - 20℃; for 18h;
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 16h;
cyclohexanone
108-94-1

cyclohexanone

C29H51AlZr

C29H51AlZr

1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O / 18 h
2: LiAlH4; H2SO4 / tetrahydrofuran / 18 h / 0 - 20 °C
View Scheme
cyclohexanone
108-94-1

cyclohexanone

1.1'-dinitro-dicyclohexyl

1.1'-dinitro-dicyclohexyl

1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / H2O / Ambient temperature
2: 66 percent / LiAlH4, H2SO4 / tetrahydrofuran / 1 h / 40 - 50 °C
View Scheme
cyclohexanone
108-94-1

cyclohexanone

1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 16 h / 20 °C
2: lithium aluminium tetrahydride / diethyl ether / 16 h / 20 °C
View Scheme
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

4-(benzyloxy)-3,5-dimethoxybenzoic acid
14588-60-4

4-(benzyloxy)-3,5-dimethoxybenzoic acid

C25H34N2O4*ClH

C25H34N2O4*ClH

Conditions
ConditionsYield
Stage #1: 1-aminomethyl‐1‐cyclohexanedimethylamine; 4-(benzyloxy)-3,5-dimethoxybenzoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 24h;
Stage #2: With hydrogenchloride In methanol
55.5%
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

C11H12ClNO5
150007-96-8

C11H12ClNO5

4-Amino-5-chloro-N-(1-dimethylamino-cyclohexylmethyl)-2-methoxy-benzamide

4-Amino-5-chloro-N-(1-dimethylamino-cyclohexylmethyl)-2-methoxy-benzamide

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature;
4-butoxy-3,5-dimethoxybenzoic acid chloride
363626-73-7

4-butoxy-3,5-dimethoxybenzoic acid chloride

1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

4-butyloxy-3,5-dimethoxy-N-[(1-dimethylaminocyclohexyl)methyl]benzamide

4-butyloxy-3,5-dimethoxy-N-[(1-dimethylaminocyclohexyl)methyl]benzamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

4-Chlorobenzamidomethyl-cyclohexyl dimethylamine

4-Chlorobenzamidomethyl-cyclohexyl dimethylamine

Conditions
ConditionsYield
In chloroform; water; benzene
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

benzoyl chloride
98-88-4

benzoyl chloride

1-benzamidomethylcyclohexyldimethylamine hydrochloride
41804-98-2

1-benzamidomethylcyclohexyldimethylamine hydrochloride

Conditions
ConditionsYield
With pyridine
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

3,4-dimethoxybenzoic acid chloride
3535-37-3

3,4-dimethoxybenzoic acid chloride

3,4-dimethoxy benzamidomethyl cyclohexyl dimethylamine hydrochloride

3,4-dimethoxy benzamidomethyl cyclohexyl dimethylamine hydrochloride

Conditions
ConditionsYield
In water; benzene
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

o-chlorobenzoyl chloride
609-65-4

o-chlorobenzoyl chloride

A

2-Chlorobenzamidomethyl cyclohexyl dimethylamine hydrochloride

2-Chlorobenzamidomethyl cyclohexyl dimethylamine hydrochloride

B

2-chlorobenzamido-methyl-cyclohexyl-dimethylamine hydrochloride
41805-04-3

2-chlorobenzamido-methyl-cyclohexyl-dimethylamine hydrochloride

Conditions
ConditionsYield
In benzene
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

3,4-dichlorobenzoyl chloride
3024-72-4

3,4-dichlorobenzoyl chloride

1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine hydrochloride

1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine hydrochloride

Conditions
ConditionsYield
With pyridine
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

A

4-methylbenzamido methyl cyclohexyl dimethylamine hydrochloride

4-methylbenzamido methyl cyclohexyl dimethylamine hydrochloride

B

4-Methylbenzamidomethyl-cyclohexyl dimethylamine hydrochloride

4-Methylbenzamidomethyl-cyclohexyl dimethylamine hydrochloride

Conditions
ConditionsYield
With triethylamine In water; benzene
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

acetamidomethylcyclohexyl-dimethylamine
41805-05-4

acetamidomethylcyclohexyl-dimethylamine

Conditions
ConditionsYield
With sodium hydroxide; acetic anhydride; sodium carbonate
4-{[2-(isopropylsulfonyl)phenyl]amino}-2-(methylsulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carboxamide
1254057-11-8

4-{[2-(isopropylsulfonyl)phenyl]amino}-2-(methylsulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carboxamide

1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

2-({[1-(dimethylamino)cyclohexyl]methyl}amino)-4-{[2-(isopropylsulfonyl)phenyl]amino}-6-oxo-1,6-dihydropyrimidine-5-carboxamide
1254046-68-8

2-({[1-(dimethylamino)cyclohexyl]methyl}amino)-4-{[2-(isopropylsulfonyl)phenyl]amino}-6-oxo-1,6-dihydropyrimidine-5-carboxamide

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 180℃; for 0.166667h; Microwave irradiation;
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

1-(3,4-dichlorobenzamidomethyl)-cyclohexylmethylamine

1-(3,4-dichlorobenzamidomethyl)-cyclohexylmethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / tetrahydrofuran / 1 h / 20 °C
1.2: 1 h / 20 °C
2.1: diethylazodicarboxylate / toluene / 18 h / 55 °C
View Scheme
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

3,4-dichlorobenzoyl chloride
3024-72-4

3,4-dichlorobenzoyl chloride

AH 7921
55154-30-8

AH 7921

Conditions
ConditionsYield
Stage #1: 1-aminomethyl‐1‐cyclohexanedimethylamine With triethylamine In tetrahydrofuran at 20℃; for 1h;
Stage #2: 3,4-dichlorobenzoyl chloride In tetrahydrofuran at 20℃; for 1h;
30.65 g
With triethylamine In diethyl ether at 20℃; for 16h;
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

C6(11)CH3Cl3O

C6(11)CH3Cl3O

3,4-dichlorobenzene[11C]carboxylic acid (dimethylamino)cyclohexylmethyl amide

3,4-dichlorobenzene[11C]carboxylic acid (dimethylamino)cyclohexylmethyl amide

Conditions
ConditionsYield
In tetrahydrofuran Reflux;
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

4-Chlorbenzamidomethylcyclohexyldimethylamin
41805-00-9

4-Chlorbenzamidomethylcyclohexyldimethylamin

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 16h;
1-aminomethyl‐1‐cyclohexanedimethylamine
41806-09-1

1-aminomethyl‐1‐cyclohexanedimethylamine

4-trifluoromethyl-phenyl acetyl chloride
329-15-7

4-trifluoromethyl-phenyl acetyl chloride

4-(trifluoromethyl)-N-{[1-(dimethylamino)cyclohexyl]methyl}benzamide

4-(trifluoromethyl)-N-{[1-(dimethylamino)cyclohexyl]methyl}benzamide

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 16h;

41806-09-1Relevant articles and documents

Synthesis and pharmacological characterization of ethylenediamine synthetic opioids in human μ-opiate receptor 1 (OPRM1) expressing cells

Hsu, Tom,Mallareddy, Jayapal R.,Yoshida, Kayla,Bustamante, Vincent,Lee, Tim,Krstenansky, John L.,Zambon, Alexander C.

, (2019/10/19)

Opioids are powerful analgesics acting via the human μ-opiate receptor (hMOR). Opioid use is associated with adverse effects such as tolerance, addiction, respiratory depression, and constipation. Two synthetic opioids, AH-7921 and U-47700 that were developed in the 1970s but never marketed, have recently appeared on the illegal drug market and in forensic toxicology reports. These agents were initially characterized for their analgesic activity in rodents; however, their pharmacology at hMOR has not been delineated. Thus, we synthesized over 50 chemical analogs based on core AH-7921 and U-47700 structures to assess for their ability to couple to Gαi signaling and induce hMOR internalization. For both the AH-7921 and U-47700 analogs, the 3,4-dichlorobenzoyl substituents were the most potent with comparable EC50 values for inhibition of cAMP accumulation; 26.49?±?11.2?nmol L?1 and 8.8?±?4.9?nmol L?1, respectively. Despite similar potencies for Gαi coupling, these two compounds had strikingly different hMOR internalization efficacies: U-47700 (10?μmol L?1) induced ~25% hMOR internalization similar to DAMGO while AH-7921 (10?μmol L?1) induced ~5% hMOR internalization similar to morphine. In addition, the R, R enantiomer of U-47700 is significantly more potent than the S, S enantiomer at hMOR. In conclusion, these data suggest that U-47700 and AH-7921 analogs have high analgesic potential in humans, but with divergent receptor internalization profiles, suggesting that they may exhibit differences in clinical utility or abuse potential.

AH-7921 DETECTION

-

Paragraph 0070; 0071, (2016/09/26)

Antibodies, immunoassay methods and kits for the detection and determination of 3,4,-dichloro-N-[(1-(dimethylamino)cyclohexyl)methyl]benzamide and 3,4,-dichloro-N-[(1-(methylamino)cyclohexyl)methyl]benzamide, as well as the precursory immunogens, are described.

Serotoninergic properties of new conformationally restricted benzamides

Yang,Bremont,Shen,Kefi,Langlois

, p. 231 - 239 (2007/10/03)

A new series of benzamides derived from metoclopramide have been synthesized, in which the vicinal carbon of the basic nitrogen atom of the ethyl chain is situated on the C3, C4, C5 and C6 rings. The diamino derivatives were prepared through Strecker's reaction from the corresponding ketones except for the cyclopropyl derivatives where 1-ethoxy-1-trimethylsiloxy cyclopropane was used as the starting material. The benzamides were prepared using the mixed anhydride method. They were tested in binding assays for D2, 5-HT3 and 5-HT4 receptors. The results show a marked increase in the selectivity and potency of these derivatives for 5-HT3 receptors with regard to metoclopramide (compound 1d: 5-HT3 K(i) = 9.03 nM; 5-HT4 K(i) > 5000; D2 K(i) > 5000). The influences of steric hindrance and hydrophobic properties on the affinity of benzamide derivatives for 5-HT3 receptors were also emphasized by these data. The X-ray crystal structure of compound 1d was compared with that of the minimal energy conformer of BRL 24682, a reference 5-HT3 receptor antagonist benzamide, determined using the Random Search program. Superimposition of the two structures showed a suitable fit between the pharmacophore groups previously determined to be important for 5-HT3 receptor antagonists. On the other hand, the hydrophobic parts of the basic moieties had different spatial occupancies.

1-(3,4-DICHLOROBENZAMIDOMETHYL)-CYCLOHEXYLDIMETHYLAMINE

-

, (2008/06/13)

Compounds of the general formula I: EQU1 in which R1 - R4 which may be the same or different represent hydrogen atoms, or C1-6 straight or branched chain alkyl, alkenyl or alkynyl group or an alkyl group substituted by a cycloalkyl group, or represents a cycloalkyl, alkoxycarbonyl, aryl, arakyl, acyl (which includes anylsulphonyl) groups in which the alkyl group or the alkyl portion of the aralkyl group may be substituted with one or more hydroxy or esterified hydroxy groups and in which the aryl groups or the aryl portion of the acyl or aralkyl group may be substituted by one or more halogen atoms, alkyl groups, hydroxy groups, alkoxy groups, trifluoromethyl, nitro, amino or dialkylamino groups, and in which R5 - R8 which may be the same or different represent hydrogen atoms or alkyl groups except that not all groups may be hydrogen, or R5 and R6 or R7 and R8 together represent a carbonyl (=O) oxygen and in any of the pairs of groups R1 /R2, R3 /R4, R5 /R6 and R7 /R8 may represent a carbocyclic or heterocyclic ring system optionally substituted by lower alkyl or aryl groups, said ring being saturated or unsaturated. These compounds have utility as oral analgesics.

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