Tert-butyl 3-(bromomethyl)azetidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 3-(bromomethyl)azetidine-1-carboxylate
• CAS No.: 253176-93-1
• Molecular Formula: C9H16BrNO2
• Molecular Weight: 250
• Hs Code.: 2933990090
• European Community (EC) Number: 802-192-9
• DSSTox Substance ID: DTXSID20693599
• Wikidata: Q72510086
• Mol file: 253176-93-1.mol

Synonyms:253176-93-1;tert-butyl 3-(bromomethyl)azetidine-1-carboxylate;1-Boc-3-(bromomethyl)azetidine;1-BOC-3-Bromomethylazetidine;3-BROMOMETHYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;MFCD16556174;C9H16BrNO2;N-(TERT-BUTOXYCARBONYL)-3-BROMOMETHYLAZETIDINE;SCHEMBL1193811;DTXSID20693599;PUKCUGDJEPVLPR-UHFFFAOYSA-N;AKOS015841232;PB13678;AM100575;DS-17290;SY018855;CS-0041440;FT-0683044;EN300-154338;tert-butyl3-(bromomethyl)azetidine-1-carboxylate;A817781;tert-Butyl 3-(bromomethyl)-1-azetidinecarboxylate;J-523181;2-Methyl-2-propanyl 3-(bromomethyl)-1-azetidinecarboxylate

Chemical Property of Tert-butyl 3-(bromomethyl)azetidine-1-carboxylate

Chemical Property:

• Boiling Point: 281.2±13.0 °C(Predicted)
• PKA: -2.33±0.40(Predicted)
• PSA: 29.54000
• Density: 1.363±0.06 g/cm3(Predicted)
• LogP: 2.18610
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Sparingly soluble in water at 25°C, 0.83 g/L.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 249.03644
• Heavy Atom Count: 13
• Complexity: 194

Purity/Quality:

98%, ^*data from raw suppliers

1-Boc-3-Bromomethylazetidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(C1)CBr
• Uses: It is used as an active pharmaceutical intermediate.

Technology Process of Tert-butyl 3-(bromomethyl)azetidine-1-carboxylate

There total 4 articles about Tert-butyl 3-(bromomethyl)azetidine-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:

3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (142253-56-3) → 3-bromomethyl-azetidine-1-carboxylic acid tert-butyl ester (253176-93-1)

Guidance literature:

With bromine; triphenylphosphine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 3-bromomethyl-azetidine-1-carboxylic acid tert-butyl ester (253176-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / tert-butyl alcohol / 20 °C

2: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3: triphenylphosphine; bromine / N,N-dimethyl-formamide / 0 - 20 °C

With borane-THF; bromine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide; tert-butyl alcohol;

Reference yield:

1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid (142253-55-2) → 3-bromomethyl-azetidine-1-carboxylic acid tert-butyl ester (253176-93-1)

Guidance literature:

Multi-step reaction with 2 steps

1: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: triphenylphosphine; bromine / N,N-dimethyl-formamide / 0 - 20 °C

With borane-THF; bromine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid

Downstream raw materials:

(E)-N-Boc-3-((((2-amino-7-(4-fluoro-2-(pyridin-3-yl)phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-ylidene)amino)oxy)methyl)azetidine

tert-butyl 3-((5-(4-bromophenyl)-7-oxo-4,6-diazaspiro[2.4]hept-4-en-6-yl)methyl)azetidine-1-carboxylate