Methyl acetimidate

Base Information

• Chemical Name: Methyl acetimidate
• CAS No.: 14777-29-8
• Molecular Formula: C₃H₇NO
• Molecular Weight: 73.0947
• UNII: C1O9DI6F4U
• DSSTox Substance ID: DTXSID701315970
• Nikkaji Number: J26.152A
• Wikidata: Q27275068
• Mol file: 14777-29-8.mol

Synonyms:methyl acetimidate;methyl acetimidate hydrochloride

Chemical Property of Methyl acetimidate

Chemical Property:

• Vapor Pressure: 777.745mmHg at 25°C
• Boiling Point: 24.4°Cat760mmHg
• PKA: 8.10±0.70(Predicted)
• Flash Point: 5.7°C
• PSA: 33.08000
• Density: g/cm³
• LogP: 0.72970
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 73.052763847
• Heavy Atom Count: 5
• Complexity: 42.2

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=N)OC

Technology Process of Methyl acetimidate

There total 5 articles about Methyl acetimidate 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%

[Cp*Ir(η3-CH2CHCHPh)(NH=C(OMe)Me)]OTf (260783-86-6,261158-77-4) + triphenylphosphine (603-35-0) → methyl acetimidate (14777-29-8,85273-25-2) + [Cp*Ir(η3-CH2CHCHPh)(PPh3)]OTf (260783-60-6)

Guidance literature:

In tetrahydrofuran-d8; PPh3 was added to THF-d8 soln. (Cp*Ir(η3-CH2CHCHPh)(NH=C(OMe)Me))OTf and react. mixt. was refluxed for 12 h; react. mixt. was cooled to room temp., volatiles were removed, residue was washed with Et2O; elem. anal.;

DOI:10.1021/om9908480

Reference yield:

methanol (67-56-1) + acetonitrile (75-05-8,26809-02-9) → methyl acetimidate (14777-29-8,85273-25-2)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja01501a071 DOI:10.1021/ja00877a016

Reference yield:

cis-(CO)5Cr{HNC(OCH3)CH3} (15391-98-7,15391-97-6) → methyl acetimidate (14777-29-8,85273-25-2)

Guidance literature:

thermal decompn. in high vacuum;

upstream raw materials:

methanol

acetonitrile

cis-(CO)5Cr{HNC(OCH₃)CH₃}

trans-(CO)5Cr{HNC(OCH₃)CH₃}

Downstream raw materials:

5-chloro-1-(3-diethylamino-propyl)-2-methyl-1H-benzimidazole

5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one

N-(toluene-4-sulfonyl)-acetimidic acid methyl ester

3-(4-chlorophenyl)-5-methyl-1,2,4-oxadiazole

Refernces

• 1、 Chin, Chong Shik,Chong, Daesung,Lee, Byeongno,Jeong, Hyunmok,Won, Gyongshik,Do, Youngkyu,Park, Young Ja. "Activation of acetonitrile in [Cp*Ir(η3-CH2CHCHPh)(NCMe)]+: Crystal structures of iridium-amidine, imino-ether, amido, and amide complexes". . p. 638 - 648. Retrieved 2008/10/08.