5-Chloromethyl-2-oxazolidinone

Base Information

• Chemical Name: 5-Chloromethyl-2-oxazolidinone
• CAS No.: 22625-57-6
• Molecular Formula: C4H6 Cl N O2
• Molecular Weight: 135.55
• Hs Code.: 29349990
• European Community (EC) Number: 245-137-9
• NSC Number: 111158
• DSSTox Substance ID: DTXSID201302718
• Nikkaji Number: J236.709B
• Mol file: 22625-57-6.mol

Synonyms:5-Chloromethyl-2-oxazolidinone;22625-57-6;5-(chloromethyl)oxazolidin-2-one;5-(Chloromethyl)-1,3-oxazolidin-2-one;2-Oxazolidinone, 5-(chloromethyl)-;5-Chloromethyloxazolidin-2-one;EINECS 245-137-9;C4H6ClNO2;2-Oxazolidinone,5-(chloromethyl)-;NSC111158;NSC 111158;SCHEMBL1098287;FNOZCEQRXKPZEZ-UHFFFAOYSA-;5-(Chloromethyl)-2-oxazolidinone;DTXSID201302718;BBL027510;MFCD00005269;STK943364;5-chloromethyl-1,3-oxazolidin-2-one;5-Chloromethyl-2-oxazolidinone, 97%;AKOS000121508;AKOS016039399;CS-W011062;NSC-111158;AS-40129;5-(Chloromethyl)-1,3-oxazolidin-2-one #;FT-0619699;EN300-16576;W-201945;Z56346848

Chemical Property of 5-Chloromethyl-2-oxazolidinone

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 4.6E-06mmHg at 25°C
• Melting Point: 102-104 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 382.8°Cat760mmHg
• PKA: 12.09±0.40(Predicted)
• Flash Point: 185.3°C
• PSA: 38.33000
• Density: 1.294g/cm³
• LogP: 0.66240
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 135.0087061
• Heavy Atom Count: 8
• Complexity: 106

Purity/Quality:

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

5-Chloromethyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(OC(=O)N1)CCl

Technology Process of 5-Chloromethyl-2-oxazolidinone

There total 12 articles about 5-Chloromethyl-2-oxazolidinone 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: 82.0%

carbamic acid phenyl ester (622-46-8) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 5-(chloromethyl)-1,3-oxazolidin-2-one (22625-57-6)

Guidance literature:

With C₂₅H₂₀AlCl₆NO₄; In acetonitrile; at 50 ℃; for 18h; regioselective reaction;

DOI:10.1002/adsc.201500635

Reference yield: 81.0%

2,3-dichloropropylamine (137688-61-0) + carbon dioxide (124-38-9,18923-20-1) → 5-(chloromethyl)-1,3-oxazolidin-2-one (22625-57-6) + 5-chloro-tetrahydro-2H-1,3-dioxazin-2-one (1644110-78-0)

Guidance literature:

With caesium carbonate; In ethanol; at 65 ℃; for 1h; under 26252.6 Torr; Time; Reagent/catalyst; regioselective reaction; Autoclave; Green chemistry;

DOI:10.1002/chem.201402368

Reference yield: 72.0%

potassium cyanate (590-28-3) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 5-(chloromethyl)-1,3-oxazolidin-2-one (22625-57-6)

Guidance literature:

With magnesium sulfate; In water; at 100 ℃; for 5h;

upstream raw materials:

benzoyl-carbamic acid-(β,β'-dichloro-isopropyl ester)

cyanic acid

epichlorohydrin

potassium cyanate

Downstream raw materials:

N,N-diphenylurea

benzyl 4-((2-oxooxazolidin-5-yl)methyl)piperazine-1-carboxylate

3-(4-bromobenzyl)-5-(chloromethyl)-1,3-oxazolidin-2-one

5-((2-chloro-5-((((R)-1-(3-chlorophenyl)ethyl)amino)methyl)phenoxy)methyl)oxazolidin-2-one

Refernces

• 1、 Niemi, Teemu,Perea-Buceta, Jesus E.,Fernandez, Israel,Alakurtti, Sami,Rantala, Erika,Repo, Timo. "Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide". supporting information. p. 8867 - 8871. Retrieved 2014/07/22.
• 2、 Anand Kumar,Veera Babu,Rao, Rama Koteshwar,Srinivas, Kumbam,Madhusudhan,Mukkanti. "Synthesis of racemic and chiral Carvedilol starting from corresponding 5-(chloromethyl)oxazolidin-2-one". . p. 1430 - 1435. Retrieved 2012/11/06.