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61894-99-3

61894-99-3

Identification

  • Product Name:1H-Carbazol-3-amine,2,3,4,9-tetrahydro-

  • CAS Number: 61894-99-3

  • EINECS:200-528-9

  • Molecular Weight:186.257

  • Molecular Formula: C12H14N2

  • HS Code:2933990090

  • Mol File:61894-99-3.mol

Synonyms:Carbazole,3-amino-1,2,3,4-tetrahydro- (6CI,7CI);3-Amino-1,2,3,4-tetrahydrocarbazole;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:3-Amino-1,2,3,4-tetrahydrocarbazol
  • Packaging:1g
  • Price:$ 225
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:2,3,4,9-Tetrahydro-1H-carbazol-3-amine 97%
  • Packaging:10g
  • Price:$ 620
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  • Manufacture/Brand:Crysdot
  • Product Description:2,3,4,9-Tetrahydro-1H-carbazol-3-amine 97%
  • Packaging:5g
  • Price:$ 367
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  • Manufacture/Brand:AstaTech
  • Product Description:2,3,4,9-TETRAHYDRO-1H-CARBAZOL-3-AMINE 98%
  • Packaging:10 / G
  • Price:$ 869
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  • Manufacture/Brand:AstaTech
  • Product Description:2,3,4,9-TETRAHYDRO-1H-CARBAZOL-3-AMINE 98%
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  • Price:$ 193
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  • Manufacture/Brand:AstaTech
  • Product Description:2,3,4,9-TETRAHYDRO-1H-CARBAZOL-3-AMINE 98%
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  • Price:$ 579
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3-AMINO-1,2,3,4-TETRAHYDROCARBAZOL 95.00%
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  • Manufacture/Brand:Alichem
  • Product Description:2,3,4,9-Tetrahydro-1H-carbazol-3-amine
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  • Manufacture/Brand:Alichem
  • Product Description:2,3,4,9-Tetrahydro-1H-carbazol-3-amine
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  • Manufacture/Brand:AK Scientific
  • Product Description:3-Amino-1,2,3,4-tetrahydrocarbazol
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Relevant articles and documentsAll total 8 Articles be found

INDOLE AHR INHIBITORS AND USES THEREOF

-

, (2018/11/22)

The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

Asymmetric chemoenzymatic synthesis of ramatroban using lipases and oxidoreductases

Busto, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente

, p. 4842 - 4848 (2012/07/31)

A chemoenzymatic asymmetric route for the preparation of enantiopure (R)-ramatroban has been developed for the first time. The action of lipases and oxidoreductases has been independently studied, and both were found as excellent biocatalysts for the production of adequate chiral intermediates under very mild reaction conditions. CAL-B efficiently catalyzed the resolution of (±)-2,3,4,9-tetrahydro-1H-carbazol-3-ol that was acylated with high stereocontrol. On the other hand, ADH-A mediated bioreduction of 4,9-dihydro-1H-carbazol-3(2H)-one provided an alternative access to the same enantiopure alcohol previously obtained through lipase-catalyzed resolution, a useful synthetic building block in the synthesis of ramatroban. Inversion of the absolute configuration of (S)-2,3,4,9-tetrahydro-1H-carbazol-3-ol has been identified as a key point in the synthetic route, optimizing this process to avoid racemization of the azide intermediate, finally yielding (R)-ramatroban in enantiopure form by the formation of the corresponding amine and the convenient functionalization of both exocyclic and indole nitrogen atoms.

N,N-Dimethyl-[9-(arylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]amines as novel, potent and selective 5-HT6 receptor antagonists

Nirogi, Ramakrishna V. S.,Konda, Jagadishu Babu,Kambhampati, Ramasastry,Shinde, Anil,Bandyala, Thrinath Reddy,Gudla, Parandhama,Kandukuri, Kiran Kumar,Jayarajan, Pradeep,Kandikere, Vishwottam,Dubey, P. K.

, p. 6980 - 6985,6 (2020/09/02)

The design, synthesis and SAR of novel tetrahydrocarbazole derivatives having 5-HT6 receptor antagonist activity is presented. The racemic compound 15e was found to possess desirable pharmacokinetic properties, adequate brain penetration and activity in animal models of cognition.

SYNTHESIS OF (2-AMINO)-TETRAHYDROCARBAZOLE-PROPANOIC ACID

-

Page/Page column 13, (2010/08/04)

The present invention provides a new approach to the synthesis of 2-amino-tetrahydrocarbazole-propanoic acid, a key intermediate for the synthesis of Ramatroban. More specifically, a synthesis of 2-amino-tetrahydrocarbazole- propanoic acid which includes oxidizing an aminocyclohexanol to form an aminocyclohexanone, condensing the aminocyclohexanone to form a tetrahydrocarbazole, deprotecting the tetrahydrocarbazole to yield a racemic mixture of a tetrahydrocarbazole, resolving the racemic mixture to obtain a yield mixture with an enantiomeric excess of one enantiomer over another, alkylating the excess enantiomer to yield an alkyl ester, and hydrolyzing the alkyl ester to yield 2-amino-tetrahydrocarbazole-propanoic acid.

Fluorescence Studies with Tryptophan Analogues: Excited State Interactions Involving the Side Chain Amino Group

Eftink, Maurice R.,Jia, Yiwei,Hu, Dana,Ghiron, Camillo, A.

, p. 5713 - 5723 (2007/10/02)

The fluorescence of a large set of tryptophan analogues, including several that are conformationally constrained, was studied.The constrained analogues include tetrahydrocarboline-3-carboxylic acid and 3-amino-3-carboxytetrahydrocarbazole.Steady state and time-resolved fluorescence measurements were made as a function of pH.The fluorescence quantum yields of the constrained analogues are higher than those for the unconstrained counterparts.The emission intensity of the constrained analogues, as well as 4-methyltryptophan, decreases with deprotonation of the side chain α-ammonium groups; this is in contrast to the increase in fluorescence of tryptophan with deprotonation of this group.These results are consistent with the existence of excited state proton transfer to carbon 4 of the indole ring as a quenching mechanism, which is sterically prohibited in the constrained analogues and 4-methyltryptophan.From quantum yield and lifetime data (most decays are nonexponential), the effective rate constant for nonradiative depopulation of the excited state was calculated.For tryptophan analogues having two side chain functional groups, there is a synergistic effect; the presence of two side chain groups causes more quenching than expected from the sum of the individual contributions.For analogues having an α-ammonium group, this synergism appears to be correlated with an induced change in the pKa of this group.Deprotonation of this α-ammonium group also caused a red shift in the emission of these compounds; this appears to be due to electrostatic repulsion between the α-NH3+ group and the excited indole dipole.

Process route upstream and downstream products

Process route

1,4-dioxaspiro[4.5]decan-8-amine
97096-16-7

1,4-dioxaspiro[4.5]decan-8-amine

phenylhydrazine
100-63-0

phenylhydrazine

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3,116650-33-0,116650-34-1,134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

Conditions
Conditions Yield
With sulfuric acid; In water; at 95 - 100 ℃;
50%
tert-butyl N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)carbamate
1392271-79-2

tert-butyl N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)carbamate

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3,116650-33-0,116650-34-1,134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

Conditions
Conditions Yield
With trifluoroacetic acid; In dichloromethane; at 28 ℃; for 2h;
3-azido-2,3,4,9-tetrahydro-1H-carbazole

3-azido-2,3,4,9-tetrahydro-1H-carbazole

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3,116650-33-0,116650-34-1,134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

Conditions
Conditions Yield
With hydrogen; palladium on activated charcoal; In methanol; for 24h; under 3102.9 Torr; Ambient temperature;
52%
With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 2h;
3-(phthalimido)-1,2,3,4-tetrahydrocarbazole
1234493-21-0

3-(phthalimido)-1,2,3,4-tetrahydrocarbazole

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3,116650-33-0,116650-34-1,134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

Conditions
Conditions Yield
With hydrazine; In methanol;
1,2,3,4-tetrahydrocarbazol-3-one
51145-61-0

1,2,3,4-tetrahydrocarbazol-3-one

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3,116650-33-0,116650-34-1,134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

Conditions
Conditions Yield
With ammonium acetate; cyano-borane; compound with lithium hydride; In ethanol;
With ammonium acetate; cyano-borane; compound with lithium hydride; In methanol; for 50h; Yield given; Ambient temperature; activated molecular sieves 4A;
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
2: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
3: sodium azide / 24 h
4: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
With dmap; sodium tetrahydroborate; sodium azide; palladium on activated charcoal; hydrogen; triethylamine; In methanol; dichloromethane;
(+)-mandelic acid salt of (+)-3-amino-1,2,3,4-tetrahydrocarbazole

(+)-mandelic acid salt of (+)-3-amino-1,2,3,4-tetrahydrocarbazole

racemic 3-amino-1,2,3,4-tetrahydrocarbazole

racemic 3-amino-1,2,3,4-tetrahydrocarbazole

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3,116650-33-0,116650-34-1,134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

Conditions
Conditions Yield
In tetrahydrofuran;
(+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol
128432-38-2,14384-34-0

(+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3,116650-33-0,116650-34-1,134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 88 percent / pyridine / Ambient temperature
2: sodium azide / dimethylsulfoxide / 24 h / 100 °C
3: 52 percent / H2 / 10percent Pd/C / methanol / 24 h / 3102.9 Torr / Ambient temperature
With sodium azide; hydrogen; palladium on activated charcoal; In pyridine; methanol; dimethyl sulfoxide;
Multi-step reaction with 3 steps
1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium azide / 24 h
3: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
With dmap; sodium azide; palladium on activated charcoal; hydrogen; triethylamine; In methanol; dichloromethane;
3-hydroxy-1,2,3,4-tetrahydrocarbazole p-toluenesulphonate ester
34154-31-9

3-hydroxy-1,2,3,4-tetrahydrocarbazole p-toluenesulphonate ester

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3,116650-33-0,116650-34-1,134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium azide / dimethylsulfoxide / 24 h / 100 °C
2: 52 percent / H2 / 10percent Pd/C / methanol / 24 h / 3102.9 Torr / Ambient temperature
With sodium azide; hydrogen; palladium on activated charcoal; In methanol; dimethyl sulfoxide;
cyclohexanedione monoethylene ketal
4746-97-8

cyclohexanedione monoethylene ketal

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3,116650-33-0,116650-34-1,134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
5.1: sodium azide / 24 h
6.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
With dmap; sodium tetrahydroborate; sodium azide; palladium on activated charcoal; hydrogen; magnesium sulfate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; acetone;
Multi-step reaction with 3 steps
1: pyridine; hydroxylamine hydrochloride / ethanol / 5 h / 25 °C / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Reflux
3: sulfuric acid / water / 95 - 100 °C
With pyridine; lithium aluminium tetrahydride; sulfuric acid; hydroxylamine hydrochloride; In tetrahydrofuran; ethanol; water;
phenylhydrazine
100-63-0

phenylhydrazine

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3,116650-33-0,116650-34-1,134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
5.1: sodium azide / 24 h
6.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
With dmap; sodium tetrahydroborate; sodium azide; palladium on activated charcoal; hydrogen; magnesium sulfate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; acetone;
Multi-step reaction with 2 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 28 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 28 °C
With magnesium sulfate; trifluoroacetic acid; In dichloromethane;

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