75355-65-6

Basic information

• Product Name: 3-hydroxy-1-methylpropyl acetate
• Synonyms: 3-hydroxy-1-methylpropyl acetate;1,3-Butanediol 3-acetate;Acetic acid 1-methyl-3-hydroxypropyl ester;Acetic acid 3-hydroxy-1-methylpropyl ester
• CAS NO: 75355-65-6
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.15768
• EINECS: 278-191-7
• Mol File: 75355-65-6.mol

Chemical Properties

• Boiling Point: 142.6 °C at 760 mmHg
• Flash Point: 41.7 °C
• Appearance: /
• Density: 1.024 g/cm³
• Vapor Pressure: 2.25mmHg at 25°C
• Refractive Index: 1.427
• PKA: 14.84±0.10(Predicted)
• CAS DataBase Reference: 3-hydroxy-1-methylpropyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-1-methylpropyl acetate(75355-65-6)
• EPA Substance Registry System: 3-hydroxy-1-methylpropyl acetate(75355-65-6)

Safety Data

• Hazardous Substances Data: 75355-65-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H12O3/c1-5(3-4-7)9-6(2)8/h5,7H,3-4H2,1-2H3

Upstream product

• 766-20-1 2,4-dimethyl-[1,3]dioxane 
• 18826-95-4 1.3-butanediol 
• 108-24-7 acetic anhydride 
• 75-07-0 acetaldehyde 
• 75-36-5 acetyl chloride 
• 1445-45-0 Trimethyl orthoacetate 
• 64-19-7 acetic acid 
• 1117-31-3 1,3-diacetoxybutane 

Relevant articles and documents

Sulfonic acid-functionalized periodic mesoporous organosilicas in esterification and selective acylation reactions

The application of sulfonic acid-functionalized periodic mesoporous organosilicas (PMOs) having either phenyl (1a) or ethyl (1b) bridging groups was investigated in the esterification of a variety of alcohols and fatty acids. It was found that 1b consistently exhibited higher catalytic performance than 1a in the described reaction. In particular, it was proposed that the superior catalytic activity of 1b in esterification of fatty acids with methanol is a result of adequate hydrophobic-hydrophilic surface balance in the ethyl PMO catalyst. In addition, the study of chemoselective acylation of 1,3-butanediol with dodecanoic acid with varied mesoporous silica-supported solid sulfonic acids including both 1a and 1b implies that there is a compromise between the reaction selectivity and the surface physicochemical properties of the employed catalyst. Our results clearly show that the catalyst having high surface hydrophilic nature gives high selectivity toward the formation of mono-acylated products whereas those with relatively high hydrophobic characteristics showed enhanced selectivity toward the formation of di-acylated products.

Gold(I)/copper(II)-cocatalyzed tandem cyclization/semipinacol reaction: Construction of 6-Aza/Oxa-Spiro[4.5]decane skeletons and formal synthesis of (±)-halichlorine

A simple and efficient strategy for the construction of 6-aza/oxa-spiro[4.5]decane skeletons under the cocatalysis of gold(I)/copper(II) was developed, and its potential utility was demonstrated by a formal synthesis of the biologically active marine alkaloid (±)-halichlorine.

Simple and practical method for selective acylation of primary hydroxy group catalyzed by N-methyl-2-phenylimidazole (Ph-NMI) or 2-phenylimidazo[2,1-b]benzothiazoles (Ph-IBT)

N-Methyl-2-phenylimidazole (Ph-NMI) and 2-phenylimidazo[2,1-b]benzothiazoles (Ph-IBT) catalyzed selective acylation of primary alcohols using acid anhydrides. The Ph-NMI- or Ph-IBT-catalyzed reaction using (PhCO)2O as an acylating agent could particularly acylate the primary hydroxy group of 1,n-diols (n ≥ 3) with a high, synthetically useful selectivity.

A highly selective, high-speed, and hydrolysis-free O-acylation in subcritical water in the absence of a catalyst

(Chemical Equation Presented) Fast and furious: A wide range of alcohols are acylated by acetic anhydride, in the absence of catalyst, in subcritical water in a flow-type microreaction system. The esters are selectively produced in high yields at temperatures of 200 to 250°C. Varying the amount of acetic anhydride added with respect to the alcohols allows the regioselective acylation of one or both hydroxy groups of various dihydroxy compounds (see picture).

Selective acylation of a sterically hindered hydroxyl group of unsymmetrical diols containing a primary hydroxyl group such as 1,5-hexanediol in the presence of silica gel with acetyl chloride

The selective acetylation of sterically hindered hydroxyl groups of 1,5-hexanediol preadsorbed on silica gel was reported. The relation between the adsorption of the diol on SiO2 and its reactivity for selective acetylation was studied. Results demonstrated that unsymmetrical diols get adsorbed on the surface of SiO2 preferentially via a primary OH group, leaving the non-adsorbed OH group available for reaction.

Trimerization of aliphatic aldehydes to 1,3-diol monoesters catalyzed by Cp*2Sm(thf)2

Aliphatic aldehydes underwent trimerization in the presence of a catalytic amount of Cp*2Sm(thf)2 under ambient conditions to form 1,3- diol monoestcrs in good yields. For example, the reaction of acetoaldehyde catalyzed by Cp*2Sm(thf)2 gave 4-acetoxy-2-butanol (2a) and 3-acetoxy-1- butanol (3a) in 86% yield.

Unique Template Effects of Distannoxane Catalysts in Transesterification of Diol esters

1,n-Diol diacetates (n = 2,3,4) are selectively converted into the corresponding monoacetates by distannoxane-catalyzed transesterification.Such unique selectivity is not encountered with 1,n-diol diacetates where n>/=5.A great difference in reactivity is also seen in the transesterification between methyl butyrate and 1,n-diol monoacetates: the ethylene glycol derivative sluggishly undergoes transesterification whereas higher homologs react smoothly.The unique template effects of the catalysts are discussed in terms of cooperation of two different tin atoms which are located in the proximity.

A New Acylation Catalyst

Cobalt(II) chloride catalyses the acylation of alcohols and amines with anhydrides in excellent yields.