14777-29-8

Basic information

• Product Name: METHYL ACETIMIDATE HCL
• Synonyms: acetimidicacid,methylester;ethanimidicacid,methylester;methyl acetimidate;1-Methoxy-1-ethanimine;1-Methoxyethanimine;Acetimidic acid methyl
• CAS NO: 14777-29-8
• Molecular Formula: C₃H₇NO
• Molecular Weight: 73.09378
• Mol File: 14777-29-8.mol

Chemical Properties

• Boiling Point: 24.4°Cat760mmHg
• Flash Point: 5.7°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 777.745mmHg at 25°C
• Refractive Index: 1.389
• PKA: 8.10±0.70(Predicted)
• CAS DataBase Reference: METHYL ACETIMIDATE HCL(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL ACETIMIDATE HCL(14777-29-8)
• EPA Substance Registry System: METHYL ACETIMIDATE HCL(14777-29-8)

Safety Data

• Hazardous Substances Data: 14777-29-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C3H7NO/c1-3(4)5-2/h4H,1-2H3

Upstream product

• 67-56-1 methanol 
• 75-05-8 acetonitrile 
• 260783-86-6 [Cp*Ir(η3-CH2CHCHPh)(NH=C(OMe)Me)]OTf 
• 603-35-0 triphenylphosphine 
• 15391-97-6 trans-(CO)5Cr{HNC(OCH₃)CH₃} 
• 15391-98-7 cis-(CO)5Cr{HNC(OCH₃)CH₃} 

Downstream Products

• 68123-36-4 5-chloro-1-(3-diethylamino-propyl)-2-methyl-1H-benzimidazole 
• 1018808-64-4 N-{3-[(S)-5-(2,5-difluoro-phenyl)-3-((S)-2-methoxy-propionyl)-2-phenyl-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-propyl}-acetamidine 
• 670749-85-6 N-(6-Chloro-5-phenyl-1H-indazol-3-yl)acetamidine 
• 69981-57-3 N-(1-iminoethyl)benzylamine 
• 53732-41-5 (4S,5S)-4-Hydroxymethyl-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazole 
• 21614-47-1 3-(4-chlorophenyl)-5-methyl-1,2,4-oxadiazole 
• 40412-03-1 N-(toluene-4-sulfonyl)-acetimidic acid methyl ester 
• 5423-97-2 5-ethoxymethyl-2-methyl-3H-pyrimidin-4-one 

Relevant articles and documents

Activation of acetonitrile in [Cp*Ir(η3-CH2CHCHPh)(NCMe)]+: Crystal structures of iridium-amidine, imino-ether, amido, and amide complexes

Reactions of [Cp*Ir(η3-CH2CHCHPh)(NCMe)]OTf (1) with protic amines, alcohols, and water produce amidine complexes [Cp*Ir(η3-CH2CHCHPh)(NH=C(NR2)Me)]OTf (2) (R2 = (Me)2 (a), (Me)(H) (b), (i-Pr)(H) (c), (-CH2(CH2)3CH2-) (d)), imino-ether complexes [Cp*Ir-(η3-CH2CHCHPh)(NH=C(OR′)Me)]OTf (4) (R′ = Me (a), Et (b), i-Pr (c)), and amido complex Cp*Ir(η3-CH2CHCHPh)(NHC(=O)Me) (5-K), respectively. The keto form amido complex 5-K undergoes tautomerization to give the enol form complex Cp*Ir(η3-CH2CHCHPh)(N= C(OH)Me) (5-E) in polar solvents. Tertiary amines (NMe3, NEt3) react with 1 in chlorinated solvents (XCl) to give the chloro complex Cp*IrCl(η3-CH2CHCHPh) (3) and quaternary ammonium salts [R3NX]OTf(R = Me, Et and X = CH2Cl, CH3, CHCl2, CCl3, PhCH2). Crystal structures of 2a, 4a, 5-K, and [Cp*Ir(NH=C(OH)Me)(OH2)(PPh3)]OTf2 (6) have been determined by single-crystal X-ray diffraction analysis, which lead us to suggest hybrid structures, Ir--NH-C(=N+Me2)Me (2a′) for 2a and Ir--NH-C(=O+Me)Me (4a′) for 4a to some extent. Complexes 2 and 4 react with PPh3 to give an iridium(III) complex [Cp*Ir(η3-CH2CHCHPh)(PPh3)]OTf (7) and the free amidines NH=C(NR2)Me (8) and imino-ethers NH=C(OR′)Me (9), respectively. Nitrile complexes 1 and [Cp*Ir(η3-CH2CHCHPh)(NCCH= CHMe)]OTf(10) catalyze the hydration of the nitriles in the presence of Na2CO3 to produce amides, and the benzonitrile complex [Cp*Ir(η3-CH2CHCHPh)(NCPh)]OTf(11) catalyzes the methanolysis of benzonitrile in the presence of Na2CO3 to produce NH=C(OMe)Ph. Plausible mechanisms for these catalytic reactions are suggested with the amido and imino-ether complexes such as 4 and 5 being involved.