tert-Butyl 1H-imidazole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 1H-imidazole-1-carboxylate
• CAS No.: 49761-82-2
• Molecular Formula: C8H12N2O2
• Molecular Weight: 168.195
• Hs Code.: 2933290090
• European Community (EC) Number: 256-475-1
• DSSTox Substance ID: DTXSID00198032
• Nikkaji Number: J150.900D
• Mol file: 49761-82-2.mol

Synonyms:49761-82-2;N-Boc-imidazole;tert-Butyl 1H-imidazole-1-carboxylate;N-tert-Butoxycarbonylimidazole;tert-butyl imidazole-1-carboxylate;1-BOC-IMIDAZOLE;1H-Imidazole-1-carboxylic acid, 1,1-dimethylethyl ester;1-(tert-Butoxycarbonyl)imidazole;EINECS 256-475-1;MFCD00014497;SCHEMBL217823;IMIDAZOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;DTXSID00198032;tert-Butyl1H-imidazole-1-carboxylate;1-(tert-Butoxycarbonyl)-1H-imidazole;AKOS015838311;AB01144;CS-W008539;1-(tert-Butoxycarbonyl)imidazole, 97%;AS-17758;SY025186;tert-Butyl 1H-imidazole-1-carboxylate #;1-imidazolecarboxylic acid tert-butyl ester;B0916;FT-0639887;A827842

Chemical Property of tert-Butyl 1H-imidazole-1-carboxylate

Chemical Property:

• Vapor Pressure: 0.0257mmHg at 25°C
• Melting Point: 45-47 °C(lit.)
• Refractive Index: 1.507
• Boiling Point: 247.4°Cat760mmHg
• PKA: 3.49±0.10(Predicted)
• Flash Point: 103.4°C
• PSA: 44.12000
• Density: 1.08g/cm³
• LogP: 1.66630
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in hexane, acetone, and DMF.
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 168.089877630
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-tert-Butoxycarbonylimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CN=C1
• Uses: 1-Boc-imidazole is used in the preparation of water soluble polyrotaxane, via modification of α-cyclodextrin in the presence of KOH and N,N?-carbonyldiimidazole.

Technology Process of tert-Butyl 1H-imidazole-1-carboxylate

There total 7 articles about tert-Butyl 1H-imidazole-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1H-imidazole (288-32-4) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 1H-imidazole-1-carboxylate (49761-82-2)

Guidance literature:

With 1-methylimidazolium tetrafluoroborate; at 30 - 35 ℃; for 0.0833333h;

DOI:10.1016/j.tetlet.2008.02.126

Reference yield: 100.0%

1,1'-carbonyldiimidazole (530-62-1) + tert-butyl alcohol (75-65-0) → tert-butyl 1H-imidazole-1-carboxylate (49761-82-2)

Guidance literature:

potassium hydroxide; In toluene; at 60 ℃;

DOI:10.1016/j.tetasy.2004.11.044

Reference yield: 86.0%

1H-imidazole (288-32-4) + 1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate (98015-52-2) → tert-butyl 1H-imidazole-1-carboxylate (49761-82-2)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 20 ℃;

DOI:10.1055/s-1986-31724

upstream raw materials:

1H-imidazole

tert-butyl (1-chloroethyl) carbonate

1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate

1,1'-carbonyldiimidazole

Downstream raw materials:

1H-imidazole

4-hydroxymethyl-1,3-dioxolan-2-one

1,2-propylene cyclic carbonate

tert-butyl 5-hydroxy-1H-indole-1-carboxylate

Refernces

• 1、 Willcock, Helen,Cooper, Andrew I.,Adams, Dave J.,Rannard, Steve P.. "Synthesis and characterisation of polyamide dendrimers with systematically varying surface functionality". . p. 3095 - 3097. Retrieved 2009.
• 2、 De Borggraeve, Wim M.,Gilles, Philippe,Van Mileghem, Seger,Verschueren, Rik H.. "Solvent-freeN-Boc deprotection byex situgeneration of hydrogen chloride gas". supporting information. p. 5782 - 5787. Retrieved 2021/07/12.
• 3、 Pourhasan-Kisomi, Reyhaneh,Shirini, Farhad,Golshekan, Mostafa. "Organic/inorganic Fe3O4@MCM-41@Zr-piperazine: An impressive magnetite nanocatalyst for N-Tert-Butoxycarbonylation of amines". . p. 3859 - 3870. Retrieved 2019/05/08.