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Cas Database

53292-90-3

53292-90-3

Identification

  • Product Name:Cyclohexanecarboxylic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, cis-

  • CAS Number: 53292-90-3

  • EINECS:

  • Molecular Weight:243.303

  • Molecular Formula: C12H21NO4

  • HS Code:29242990

  • Mol File:53292-90-3.mol

Synonyms:cis-4-(tert-Butoxycarbonylamino)cyclohexanecarboxylic acid;cis-4-[[[(1,1-Dimethylethyl)oxy]carbonyl]amino]cyclohexanecarboxylic acid;cis-4-[(tert-Butyloxycarbonyl)amino]cyclohexanecarboxylic acid;cis-4-tert-Butoxycarbonylamino-1-cyclohexanecarboxylic acid;

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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:Usbiological
  • Product Description:Boc-cis-4-aminocyclohexane carboxylic acid
  • Packaging:2g
  • Price:$ 333
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:cis-4-(Boc-amino)cyclohexanecarboxylic acid
  • Packaging:250mg
  • Price:$ 55
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  • Manufacture/Brand:TCI Chemical
  • Product Description:cis-4-(tert-Butoxycarbonylamino)cyclohexanecarboxylic Acid >98.0%(GC)(T)
  • Packaging:5g
  • Price:$ 57
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  • Manufacture/Brand:TCI Chemical
  • Product Description:cis-4-(tert-Butoxycarbonylamino)cyclohexanecarboxylic Acid >98.0%(GC)(T)
  • Packaging:25g
  • Price:$ 170
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:cis-4-(Boc-amino)cyclohexanecarboxylic acid ≥98.0% (TLC)
  • Packaging:500mg-f
  • Price:$ 150
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Boc-cis-4-aminocyclohexane-1-carboxylic acid
  • Packaging:1g
  • Price:$ 60
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Boc-cis-4-aminocyclohexane-1-carboxylic acid
  • Packaging:5g
  • Price:$ 180
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  • Manufacture/Brand:Iris Biotech GmbH
  • Product Description:6-(Boc-NH)-cis-cyclohex-3-ene-COOH
  • Packaging:25 g
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  • Manufacture/Brand:Crysdot
  • Product Description:cis-4-(tert-Butoxycarbonylamino)cyclohexanecarboxylic Acid 97%
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  • Manufacture/Brand:Crysdot
  • Product Description:cis-4-(tert-Butoxycarbonylamino)cyclohexanecarboxylic Acid 97%
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Relevant articles and documentsAll total 27 Articles be found

PYRIMIDINYL GROUP-CONTAINING TRICYCLIC COMPOUND SERVING AS C-MET INHIBITOR

-

Paragraph 0582-0584, (2021/12/18)

Disclosed are a pyrimidinyl group-containing tricyclic compound and applications thereof in preparing a cancer-treating medicament. Specifically disclosed are a compound as represented by formula (I), a pharmaceutically acceptable salt of same, or an isomer thereof.

Preparation method of trans 4 - (tert-butyloxycarbonylamino) cyclohexanecarboxylic acid and intermediate thereof

-

, (2021/09/21)

The invention provides a preparation method of trans 4 - (tert-butyloxycarbonylamino) cyclohexanecarboxylic acid and an intermediate thereof. The preparation method is characterized by comprising the following steps of 4 - oxocyclohexane carboxylic ester and chiral ligand reagent tert-butyl sulfinamide as a raw material, reducing amination to obtain trans -4 -tert-butyl sulfinyl sulfenamide cyclohexane carboxylic acid ester by virtue of chiral ligand reagent tert-butyl sulfinamide and 4 - 95% -oxocyclohexane carboxylic ester, and is stable in basic conditions and easy to leave under an acidic condition. Reaction conditions are mild, operation is simple and convenient, yield is high, and industrial production is easy.

Compound serving as protein kinase inhibitor and application of compound

-

Paragraph 0330-0333, (2021/04/07)

The invention discloses a compound used as a protein kinase inhibitor and application of the compound, the compound has an obvious inhibition effect on protein kinase activity, can be used as a BTK inhibitor for preparing medicines for treating BTK-mediated diseases such as malignant tumors, autoimmune diseases and the like, and has wide application prospect.

BIFUNCTIONAL DEGRADERS OF INTERLEUKIN-1 RECEPTOR-ASSOCIATED KINASES AND THERAPEUTIC USE THEREOF

-

, (2021/08/27)

The present disclosure provides bifunctional compounds as IRAK4 degraders via ubiquitin proteasome pathway, and method for treating diseases modulated by IRAK4.

Discovery of Hydroxyamidine Derivatives as Highly Potent, Selective Indoleamine-2,3-dioxygenase 1 Inhibitors

Jin, Fangfang,Hu, Qiyue,Fei, Hongbo,Lv, Hejun,Wang, Shenglan,Gui, Bin,Zhang, Junzhen,Tu, Wangyang,Zhang, Yun,Zhang, Lei,Wan, Hong,Zhang, Limin,Hu, Bin,Yang, Fanglong,Bai, Chang,He, Feng,Zhang, Lianshan,Tao, Weikang

supporting information, p. 195 - 201 (2021/02/06)

In this study, a series of novel hydroxyamidine derivatives were identified as potent and selective IDO1 inhibitors by structure-based drug design. Among them, compounds 13-15 and 18 exhibited favorable enzymatic and cellular activities. Compound 18 showed improved bioavailability in mouse, rat, and dog (F% = 44%, 58.8%, 102.1%, respectively). With reasonable in vivo pharmacokinetic properties, compound 18 was further evaluated in a transgenic MC38 xenograft mouse model. The combination of compound 18 with PD-1 monoclonal antibody showed a synergistic antitumor effect. These data indicated that compound 18 as a potential cancer immunotherapy agent should warrant further investigation.

Process route upstream and downstream products

Process route

di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

trans-4-aminocyclohexanecarboxylic acid
1776-53-0,3685-23-2,3685-25-4,57043-03-5,66762-20-7

trans-4-aminocyclohexanecarboxylic acid

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid
53292-90-3,130309-46-5,53292-89-0

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid

Conditions
Conditions Yield
With triethylamine;
95%
With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; for 2h;
95%
With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
95%
di-tert-butyl dicarbonate; trans-4-aminocyclohexanecarboxylic acid; With sodium hydroxide; In water; tert-butyl alcohol; at 0 - 20 ℃;
With hydrogenchloride; In hexane; water; pH=~ 6;
82.8%
With sodium hydroxide; In tert-butyl alcohol;
66%
trans-4-aminocyclohexanecarboxylic acid; With sodium hydroxide; In 1,4-dioxane;
di-tert-butyl dicarbonate; In 1,4-dioxane; at 0 - 20 ℃; for 5h;
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

cis-4-aminocyclohexane-1-carboxylic acid
3685-23-2

cis-4-aminocyclohexane-1-carboxylic acid

cis-4-tert-butoxycarbonylaminocyclohexane-1-ylcarboxylic acid
53292-90-3

cis-4-tert-butoxycarbonylaminocyclohexane-1-ylcarboxylic acid

Conditions
Conditions Yield
With TEA;
100%
With triethylamine; In acetonitrile-water;
97%
With sodium hydroxide; In water; tert-butyl alcohol; for 1h; Ambient temperature;
78%
With sodium hydroxide; In tert-butyl alcohol;
76%
With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃;
73%
di-tert-butyl dicarbonate; cis-4-aminocyclohexane-1-carboxylic acid; With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃;
With potassium hydrogensulfate; In water;
47%
With sodium hydroxide; In 1,4-dioxane; water; at 0 - 25 ℃; for 4h;
methyl (1r,4r)‐4‐{[(tert‐butoxy)carbonyl](methyl)amino}cyclohexane‐1‐carboxylate
400899-07-2

methyl (1r,4r)‐4‐{[(tert‐butoxy)carbonyl](methyl)amino}cyclohexane‐1‐carboxylate

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid
53292-90-3,130309-46-5,53292-89-0

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid

Conditions
Conditions Yield
With lithium hydroxide; In tetrahydrofuran; at 20 ℃;
96%
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

triphenylmethyl trans-4-[(triphenylmethyl)amino]cyclohexane-1-carboxylate

triphenylmethyl trans-4-[(triphenylmethyl)amino]cyclohexane-1-carboxylate

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid
53292-90-3,130309-46-5,53292-89-0

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid

Conditions
Conditions Yield
triphenylmethyl trans-4-[(triphenylmethyl)amino]cyclohexane-1-carboxylate; With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 1h; Reflux; Large scale;
di-tert-butyl dicarbonate; With pyridine; In water; at 35 - 45 ℃; for 6h; Reagent/catalyst; Solvent; Large scale;
94.2%
tert-butyl ((3R,6S)-6-formyltetrahydro-2H-pyran-3-yl)carbamate
881657-40-5

tert-butyl ((3R,6S)-6-formyltetrahydro-2H-pyran-3-yl)carbamate

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid
53292-90-3,130309-46-5,53292-89-0

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid

Conditions
Conditions Yield
With sodium chlorite; sodium dihydrogenphosphate; In tert-butyl alcohol; at 20 ℃; for 1.5h;
78%
methyl (1R,4R)-4-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate
146307-51-9

methyl (1R,4R)-4-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid
53292-90-3,130309-46-5,53292-89-0

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid

Conditions
Conditions Yield
With methanol; sodium hydroxide; at 23 ℃; for 4h;
88%
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
1.2: 18 h / 20 °C
2.1: lithium hydroxide / tetrahydrofuran / 20 °C
With sodium hydride; lithium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;
4-aminocyclohexanecarboxylic acid
1776-53-0

4-aminocyclohexanecarboxylic acid

di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(cis)-4-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid
53292-90-3

(cis)-4-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid

Conditions
Conditions Yield
4-aminocyclohexanecarboxylic acid; di-tert-butyl dicarbonate; With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃;
With potassium hydrogensulfate; water;
47%
tert-butyl 4-(tert-butoxycarbonylamino)cyclohexanecarboxylate

tert-butyl 4-(tert-butoxycarbonylamino)cyclohexanecarboxylate

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid
53292-90-3,130309-46-5,53292-89-0

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid

Conditions
Conditions Yield
With methanol; water; lithium hydroxide; at 0 ℃; for 4h;
28.5%
4-amino-benzoic acid
150-13-0,159246-81-8,8014-65-1

4-amino-benzoic acid

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid
53292-90-3,130309-46-5,53292-89-0

trans-4-(tert-butoxycarbonylamino)cyclohexanoic acid

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 16 percent / H2 / PtO2 / ethanol; H2O / 20 °C / 2689.17 Torr
2: 66 percent / aq. NaOH / 2-methyl-propan-2-ol
With sodium hydroxide; hydrogen; platinum(IV) oxide; In ethanol; water; tert-butyl alcohol;
4-amino-benzoic acid
150-13-0,159246-81-8,8014-65-1

4-amino-benzoic acid

cis-4-tert-butoxycarbonylaminocyclohexane-1-ylcarboxylic acid
53292-90-3

cis-4-tert-butoxycarbonylaminocyclohexane-1-ylcarboxylic acid

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 49 percent / H2 / PtO2 / ethanol; H2O / 20 °C / 2689.17 Torr
2: 76 percent / aq. NaOH / 2-methyl-propan-2-ol
With sodium hydroxide; hydrogen; platinum(IV) oxide; In ethanol; water; tert-butyl alcohol;

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