3-Hydroxy-2,2-dimethylpropanal

Base Information

• Chemical Name: 3-Hydroxy-2,2-dimethylpropanal
• CAS No.: 597-31-9
• Molecular Formula: C5H10 O2
• Molecular Weight: 102.133
• Hs Code.: 2912491000
• European Community (EC) Number: 209-895-4
• NSC Number: 91821
• UNII: 6DK0IR9LLR
• DSSTox Substance ID: DTXSID9027231
• Nikkaji Number: J24.168G
• Wikipedia: Hydroxypivaldehyde
• Wikidata: Q27264584
• Mol file: 597-31-9.mol

Synonyms:3-Hydroxy-2,2-dimethylpropanal;597-31-9;Hydroxypivaldehyde;Pentaldol;Hydroxypivalaldehyde;Propanal, 3-hydroxy-2,2-dimethyl-;Pentaaldol;2,2-Dimethyl-3-hydroxypropionaldehyde;3-Hydroxypivalaldehyde;2,2-Dimethyl-3-hydroxypropanal;Hydracrylaldehyde, 2,2-dimethyl-;2,2-Dimethyl-3-hydroxypropioaldehyde;HSDB 5711;2-(Hyroxymethyl)-2-methylpropanal;3-HYDROXY-2,2-DIMETHYLPROPIONALDEHYDE;EINECS 209-895-4;UNII-6DK0IR9LLR;6DK0IR9LLR;2,2-Dimethyl-beta-hydroxypropionaldehyde;Propionaldehyde, 3-hydroxy-2,2-dimethyl-;alpha,alpha-Dimethyl-beta-hydroxypropionaldehyde;Propanal, 2,2-dimethyl-3-hydroxy-;MFCD00006963;2-(Hydroxymethyl)isobutyraldehyde;NCIOpen2_005680;SCHEMBL36074;DTXSID9027231;2,2-dimethyl-3-oxidanyl-propanal;3-Hydroxy-2,2-dimethylpropanal #;NSC91821;NSC-91821;3-hydroxy-2,2-dimethylpropanaldehyde;AKOS006240724;SB85060;2,2-dimethyl-3-hydroxy-propionaldehyde;3-hydroxy-2,2-dimethyl-propionaldehyde;3-hydroxy-2,2-dimethyl- propionaldehyde;AS-34997;SY107563;2-(HYDROXYMETHYL)-2-METHYLPROPANAL;LS-118977;FT-0648885;EN300-108646;A832441;Hydracrylaldehyde, 2,2-dimethyl- (6CI,7CI,8CI);Q-200160;2,2-DIMETHYL-3-HYDROXYPROPIONALDEHYDE, TECH.;3-HYDROXY-2,2-DIMETHYLPROPIONALDEHYDE [HSDB];Q27264584;.ALPHA.,.ALPHA.-DIMETHYL-.BETA.-HYDROXYPROPIONALDEHYDE;31091-91-5

Chemical Property of 3-Hydroxy-2,2-dimethylpropanal

Chemical Property:

• Vapor Pressure: 0.0632mmHg at 25°C
• Melting Point: 30-33 °C
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 204.4°Cat760mmHg
• PKA: 14.25±0.10(Predicted)
• Flash Point: 60.3°C
• PSA: 37.30000
• Density: 0.964g/cm³
• LogP: 0.20380
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly), DMSO, Methanol (Slightly), Water (Slightly)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 102.068079557
• Heavy Atom Count: 7
• Complexity: 66.5

Purity/Quality:

99.9% ^*data from raw suppliers

3-Hydroxy-2,2-dimethylpropanal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aldehydes
• Canonical SMILES: CC(C)(CO)C=O
• Uses: 3-Hydroxy-2,2-dimethylpropanal is used to prepare 4,1-benzoxazepines as squalene synthase inhibitors and their inhibition of cholesterol synthesis. It is also used to prepare chiral cyanohydrins.

Technology Process of 3-Hydroxy-2,2-dimethylpropanal

There total 30 articles about 3-Hydroxy-2,2-dimethylpropanal 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: 92.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + isobutyraldehyde (78-84-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Guidance literature:

With water; potassium carbonate; at 25 ℃; Cooling with ice;

DOI:10.1002/chem.201204235

Reference yield: 90.3%

2-methyl-1,2-epoxypropane (558-30-5) + carbon monoxide (201230-82-2) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Guidance literature:

2-methyl-1,2-epoxypropane; With rhodium (II) octanoate dimer; boron trifluoride; at 50 ℃; for 0.5h; Inert atmosphere;

carbon monoxide; With hydrogen; at 90 ℃; under 75007.5 Torr; Reagent/catalyst; Temperature; Pressure;

Reference yield: 85.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + trimethylsilyl propenyl ether (19879-97-1) → 2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 50 ℃;

upstream raw materials:

formaldehyd

isobutyraldehyde

trimethylsilyl propenyl ether

potassium cyanide

Downstream raw materials:

2,2-dimethyl-1,3-butanediol

2,2-Dimethyl-1,3-propanediol

pantolactone

(+-)-2,4-dihydroxy-3,3-dimethyl-butyric acid

Refernces

• 1、 Rama Rao,Mahender Rao,Sharma. "Asymmetric synthesis of (R)-3,3-dimethyl-2-hydroxy-γ-butyrolactone en route to the formal synthesis of calcium D-pantothenate". . p. 5735 - 5738. Retrieved 1994.
• 2、 Synoradzki, Ludwik,Rowicki, Tomasz,Wlostowski, Marek. "Calcium pantothenate. Part 2. Optimisation of oxynitrilase-catalysed asymmetric hydrocyanation of 3-hydroxy-2,2-dimethylaldehyde: Synthesis of (R)-pantolactone". . p. 103 - 108. Retrieved 2006.
• 3、 -. "Preparation method of DL-pantoic acid lactone". Paragraph 0042-0045; 0048-0051; 0054-0057. . Retrieved 2021/02/06.
• 4、 -. "Method for improving selectivity of aldol condensation reaction". Paragraph 0028-0030; 0037-0040. . Retrieved 2020/09/16.