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216584-22-4

216584-22-4

Identification

Synonyms:N,Nμ,Nμμ-Tri-Boc-guanidine;1,2,3-Tris(tert-butoxycarbonyl)guanidine (This product is only available in Japan.)

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Safety information and MSDS view more

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • 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 view more

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:N,N′,N′′-Tri-Boc-guanidine 97%
  • Packaging:5g
  • Price:$ 129
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:Chem-Impex
  • Product Description:N,N,N-Tri-Boc-guanidine,98%(Assaybytitration) 98%(Assaybytitration)
  • Packaging:5G
  • Price:$ 106.4
  • Delivery:In stock
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  • Manufacture/Brand:Chem-Impex
  • Product Description:N,N,N-Tri-Boc-guanidine,≥98%(Assaybytitration) ≥98%(Assaybytitration)
  • Packaging:1G
  • Price:$ 52.42
  • Delivery:In stock
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  • Manufacture/Brand:Chem-Impex
  • Product Description:N,N,N-Tri-Boc-guanidine,98%(Assaybytitration) 98%(Assaybytitration)
  • Packaging:250MG
  • Price:$ 28
  • Delivery:In stock
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  • Manufacture/Brand:Chem-Impex
  • Product Description:N,N,N-Tri-Boc-guanidine,98%(Assaybytitration) 98%(Assaybytitration)
  • Packaging:25G
  • Price:$ 498.4
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:N,N',N''-TRI-BOC-GUANIDINE 97.00%
  • Packaging:5G
  • Price:$ 898.29
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:N,N',N''-TRI-BOC-GUANIDINE 97.00%
  • Packaging:1G
  • Price:$ 283.5
  • Delivery:In stock
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  • Manufacture/Brand:AK Scientific
  • Product Description:N,N′,N′′-Tri-Boc-guanidine
  • Packaging:5g
  • Price:$ 190
  • Delivery:In stock
  • Buy Now

Relevant articles and documentsAll total 3 Articles be found

Process for the preparation of substituted pyrimidine derivatives

-

Page/Page column 22, (2010/02/16)

The present invention is directed to processes for the preparation of substituted pyrimidine derivatives, useful as intermediates in the synthesis of histamine H4 receptor modulators, and to intermediates in H4 modulator synthesis.

Triurethane-protected guanidines and triflyldiurethane-protected guanidines: New reagents for guanidinylation reactions

Feichtinger, Konrad,Sings, Heather L.,Baker, Tracy J.,Matthews, Kenneth,Goodman, Murray

, p. 8432 - 8439 (2007/10/03)

New guanidinylation reagents are reported. These reagents consist of N,N',N''-tri-Boc-guanidine (1) and N,N',N''-tri-Cbz-guanidine (2), which allow for the facile conversion of alcohols to substituted guanidines. A series of arginine analogues were synthesized via condensation of a primary or secondary alcohol with the guanidinylation reagents 1 or 2, under Mitsunobu conditions, to produce protected alkylated guanidines. In addition, an extended study of the previously reported reagents N,N'-di-Boc-N''- triflylguanidine (3) and N,N'-di-Cbz-N''-triflylguanidine (4) is presented. The triflyldiurethane-protected guanidine 3 was utilized to guanidinylate primary and secondary amines under mild conditions with high yield in both solution and on solid phase.

Process route upstream and downstream products

Process route

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

di-tert-butyl dicarbonate

guanidine hydrochloride
50-01-1

guanidine hydrochloride

1,3-bis(t-butoxycarbonyl)guanidine
332882-82-3,154476-57-0

1,3-bis(t-butoxycarbonyl)guanidine

N<sup>1</sup>,N<sup>2</sup>,N<sup>3</sup>-tris(tert-butoxycarbonyl)guanidine
216584-22-4

N1,N2,N3-tris(tert-butoxycarbonyl)guanidine

Conditions
Conditions Yield
With sodium hydroxide; In 1,4-dioxane; at 0 - 20 ℃; for 26h;
60%
35%
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

guanidine hydrochloride
50-01-1

guanidine hydrochloride

1,3-bis(t-butoxycarbonyl)guanidine
332882-82-3,154476-57-0

1,3-bis(t-butoxycarbonyl)guanidine

tert-butyl carbamimidoylcarbamate
219511-71-4

tert-butyl carbamimidoylcarbamate

N<sup>1</sup>,N<sup>2</sup>,N<sup>3</sup>-tris(tert-butoxycarbonyl)guanidine
216584-22-4

N1,N2,N3-tris(tert-butoxycarbonyl)guanidine

Conditions
Conditions Yield
With sodium hydroxide; Yield given; Multistep reaction; 1.) dioxane, water, 2.) dioxane, water, room temperature;
With sodium hydroxide; Multistep reaction; 1.) dioxane, water, 2.) dioxane, water, room temperature;
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

guanidine hydrochloride
50-01-1

guanidine hydrochloride

N<sup>1</sup>,N<sup>2</sup>,N<sup>3</sup>-tris(tert-butoxycarbonyl)guanidine
216584-22-4

N1,N2,N3-tris(tert-butoxycarbonyl)guanidine

Conditions
Conditions Yield
With potassium hydroxide; sodium carbonate; Yield given; Multistep reaction; 1.) DMSO, 5 min; other reagent: sodium hydroxide, 2.) DMSO, 40 deg C, 60 h;
guanidine hydrochloride; With sodium carbonate; potassium hydroxide; In dimethyl sulfoxide; at 20 ℃;
di-tert-butyl dicarbonate; In dimethyl sulfoxide; at 40 ℃; for 65h;
(±)-(N<sup>1</sup>-(4-chloro-3-fluorophenyl)-N<sup>2</sup>-[2-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl])oxalamide

(±)-(N1-(4-chloro-3-fluorophenyl)-N2-[2-(2-hydroxyethyl)-2,3-dihydro-1H-inden-1-yl])oxalamide

N<sup>1</sup>,N<sup>2</sup>,N<sup>3</sup>-tris(tert-butoxycarbonyl)guanidine
216584-22-4

N1,N2,N3-tris(tert-butoxycarbonyl)guanidine

C<sub>35</sub>H<sub>45</sub>ClFN<sub>5</sub>O<sub>8</sub>

C35H45ClFN5O8

Conditions
Conditions Yield
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 60 ℃; for 3h; Inert atmosphere;
69%
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 60 ℃; for 3h;
69%
tert-butyl (((2S,3R)-3-(2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetamido)-2-(hydroxylmethyl)-2,3-dihydro-1H-inden-5-yl)methyl)(N-methyl)carbamate

tert-butyl (((2S,3R)-3-(2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetamido)-2-(hydroxylmethyl)-2,3-dihydro-1H-inden-5-yl)methyl)(N-methyl)carbamate

N<sup>1</sup>,N<sup>2</sup>,N<sup>3</sup>-tris(tert-butoxycarbonyl)guanidine
216584-22-4

N1,N2,N3-tris(tert-butoxycarbonyl)guanidine

C<sub>41</sub>H<sub>56</sub>ClFN<sub>6</sub>O<sub>10</sub>

C41H56ClFN6O10

Conditions
Conditions Yield
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 80 ℃; for 1.5h; Inert atmosphere; Sealed tube; Microwave irradiation;
71%
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 80 ℃; for 1.5h; Inert atmosphere; Microwave irradiation; Sealed tube;
71%
tert-butyl (((1R,2S)-1-(2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetamido)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-5-yl)methyl)(N-methyl)carbamate

tert-butyl (((1R,2S)-1-(2-((4-chloro-3-fluorophenyl)amino)-2-oxoacetamido)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-5-yl)methyl)(N-methyl)carbamate

N<sup>1</sup>,N<sup>2</sup>,N<sup>3</sup>-tris(tert-butoxycarbonyl)guanidine
216584-22-4

N1,N2,N3-tris(tert-butoxycarbonyl)guanidine

C<sub>41</sub>H<sub>56</sub>ClFN<sub>6</sub>O<sub>10</sub>

C41H56ClFN6O10

Conditions
Conditions Yield
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 80 ℃; for 1.5h; Inert atmosphere; Sealed tube; Microwave irradiation;
66%
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 80 ℃; for 1.5h; Inert atmosphere; Sealed tube; Microwave irradiation;
66%
tert-butyl N-[4-(5-bromopent-1-ynyl)benzenecarboximidoyl]carbamate

tert-butyl N-[4-(5-bromopent-1-ynyl)benzenecarboximidoyl]carbamate

N<sup>1</sup>,N<sup>2</sup>,N<sup>3</sup>-tris(tert-butoxycarbonyl)guanidine
216584-22-4

N1,N2,N3-tris(tert-butoxycarbonyl)guanidine

tert-butyl N-[N,N'-bis(tert-butoxycarbonyl)-N-[5-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenyl]pent-4-ynyl]carbamimidoyl]-N-[5-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenyl]pent-4-ynyl]carbamate

tert-butyl N-[N,N'-bis(tert-butoxycarbonyl)-N-[5-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenyl]pent-4-ynyl]carbamimidoyl]-N-[5-[4-(N-tert-butoxycarbonyl carbamimidoyl)phenyl]pent-4-ynyl]carbamate

Conditions
Conditions Yield
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; at 20 ℃; Cooling with ice;
53.4%
3-(4-(6-(butylthio)imidazo[1,2-a]pyridin-2-yl)phenoxy)propan-1-ol

3-(4-(6-(butylthio)imidazo[1,2-a]pyridin-2-yl)phenoxy)propan-1-ol

N<sup>1</sup>,N<sup>2</sup>,N<sup>3</sup>-tris(tert-butoxycarbonyl)guanidine
216584-22-4

N1,N2,N3-tris(tert-butoxycarbonyl)guanidine

3-(4-(6-(butylthio)imidazo[1,2-a]pyridin-2-yl)phenoxy)propan amine tri-boc guanadine

3-(4-(6-(butylthio)imidazo[1,2-a]pyridin-2-yl)phenoxy)propan amine tri-boc guanadine

Conditions
Conditions Yield
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 5 - 50 ℃; for 18h; Inert atmosphere;
0.04 g
tert-butyl N-[4-(4-bromobutoxy)benzenecarboximidoyl]carbamate

tert-butyl N-[4-(4-bromobutoxy)benzenecarboximidoyl]carbamate

N<sup>1</sup>,N<sup>2</sup>,N<sup>3</sup>-tris(tert-butoxycarbonyl)guanidine
216584-22-4

N1,N2,N3-tris(tert-butoxycarbonyl)guanidine

tert-butyl N-[N,N'-bis(tert-butoxycarbonyl)carbamimidoyl]-N-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]carbamate

tert-butyl N-[N,N'-bis(tert-butoxycarbonyl)carbamimidoyl]-N-[4-[4-(N-tert-butoxycarbonylcarbamimidoyl)phenoxy]butyl]carbamate

Conditions
Conditions Yield
With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃;
methyl 1-phenylprop-2-enyl carbonate
160879-62-9

methyl 1-phenylprop-2-enyl carbonate

N<sup>1</sup>,N<sup>2</sup>,N<sup>3</sup>-tris(tert-butoxycarbonyl)guanidine
216584-22-4

N1,N2,N3-tris(tert-butoxycarbonyl)guanidine

C<sub>34</sub>H<sub>45</sub>N<sub>3</sub>O<sub>6</sub>

C34H45N3O6

Conditions
Conditions Yield
With tetrakis(triphenylphosphine) palladium(0); In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
94%

Global suppliers and manufacturers

Global( 7) Suppliers
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  • LEAP CHEM Co., Ltd.
  • Business Type:Trading Company
  • Contact Tel:0571-87317139
  • Emails:market15@leapchem.com
  • Main Products:89
  • Country:China (Mainland)
  • FDC-Chemical
  • Business Type:Trading Company
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  • Emails:sales@fdc-chemical.com
  • Main Products:1
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