13820-09-2

Basic information

• Product Name: 1,1,1-Trimethoxypentane
• Synonyms: 1,1,1-TRIMETHOXY-N-PENTANE;1,1,1-TRIMETHOXYPENTANE;PENTANE, 1,1,1-TRIMETHOXY-;ORTHO-N-VALERIC ACID TRIMETHYL ESTER;TRIMETHYL ORTHO-N-VALERATE;TRIMETHYL ORTHOVALERATE;TRIMETHYL-2-VALERATE;1,1,1-trimethoxy-pentan
• CAS NO: 13820-09-2
• Molecular Formula: C₈H₁₈O₃
• Molecular Weight: 162.23
• EINECS: 237-496-5
• Product Categories: Miscellaneous;Orthoesters;Acetals/Ketals/Ortho Esters;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 13820-09-2.mol

Chemical Properties

• Boiling Point: 165 °C
• Flash Point: 41 °C
• Appearance: Colorless liquid
• Density: 0.941 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.51mmHg at 25°C
• Refractive Index: 1.408-1.41
• Storage Temp.: Flammables area
• Sensitive: Moisture Sensitive
• Merck: 14,9717
• BRN: 1739200
• CAS DataBase Reference: 1,1,1-Trimethoxypentane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1-Trimethoxypentane(13820-09-2)
• EPA Substance Registry System: 1,1,1-Trimethoxypentane(13820-09-2)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38-10-36/38
• Safety Statements: 37/39-26-16-36
• RIDADR: 1993
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 13820-09-2(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Synthesis:
1,1,1-Trimethoxypentane is used as a synthetic intermediate for the preparation of 1,2,4-triazolo[1,5-c]pyrimidine derivatives, which are human adenosine A3 receptor ligands. These ligands have potential applications in the development of drugs targeting various diseases and conditions.
2. Used in Organic Chemistry:
1,1,1-Trimethoxypentane is used as a precursor to prepare N-sulfonyl and N-sulfinyl imines and imidates, which are important building blocks in organic chemistry and can be utilized in the synthesis of a wide range of compounds.
3. Used in the Preparation of 9-O-Acyl Derivatives:
1,1,1-Trimethoxypentane is employed in the preparation of various 9-O-acyl derivatives of N-acetyland N-glycoloyl-neuraminic acid. These derivatives have potential applications in the development of new drugs and pharmaceuticals.
4. Used in the Synthesis of Benzimidazolyl-Quinazolinones:
1,1,1-Trimethoxypentane is also used in the synthesis of 2-methyl, 2-ethyl, 2-propyl, and 2-butyl-3-benzimidazolyl-4(3H)-quinazolinones. These compounds have potential applications in various fields, including pharmaceuticals and materials science.
5. Used in Research and Development:
The kinetics of unimolecular gas-phase elimination of 1,1,1-Trimethoxypentane has been investigated, providing valuable insights into its chemical properties and potential applications in various industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1922, 1946 DOI: 10.1021/ja01214a015

InChI:InChI=1/C8H18O3/c1-5-6-7-8(9-2,10-3)11-4/h5-7H2,1-4H3

Upstream product

• 67-56-1 methanol 
• 39739-46-3 methyl pentanimidate hydrochloride 
• 110-59-8 pentanonitrile 

Downstream Products

• 106-35-4 heptan-3-one 
• 820-29-1 decan-5-one 
• 101498-71-9 1-phenyl-hept-1-yn-3-one-dimethylacetal 
• 103305-38-0 (2S,3R)-4-Methyl-3-phenyl-2-propyl-pent-4-enoic acid methyl ester 
• 103305-38-0 (2R,3R)-4-Methyl-3-phenyl-2-propyl-pent-4-enoic acid methyl ester 
• 134402-54-3 5-n-butyl-2,4-dihydro-4-(4-nitrobenzyl)-3H-1,2,4-triazole-3-thione 
• 2152-44-5 betamethasone-valerate 
• 123241-24-7 C₂₇H₂₈N₂O₂ 
• 102342-62-1 2,4-dihydroxy-6-n-butylbenzoic acid, methyl ester 
• 134425-18-6 5-n-butyl-4-<(2'-cyanobiphenyl-4-yl)methyl>-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 138401-20-4 tert-butyl-4'-<(2-n-butyl-4-oxo-1,3-diazaspiro<4.4>non-1-en-3-yl)methyl>biphenyl-2-carboxylate 
• 67-56-1 methanol 
• 624-24-8 methyl valerate 
• 84133-05-1 1-benzyl-5-cyano-4-((1-methoxypentylene)amino)imidazole 

Relevant articles and documents

A flexible Pinner preparation of orthoesters: The model case of trimethylorthobenzoate

In the absence of additional solvents, a novel procedure was implemented for the synthesis of trimethylorthoesters through the Pinner reaction. At 5 °C, the reaction of both aliphatic and aromatic nitriles (RCN; R = Et, Bu, Ph) with a moderate excess of MeOH and gaseous HCl gave the corresponding imidate hydrochlorides [RC(NH)OR′·HCl] in excellent yields (>90%). At 25-65 °C, the methanolysis of alkyl imidate salts provided trimethylortho-propionate and valerate, while only traces of trimethylorthobenzoate (TMOB) were observed. However, the aromatic hydrochloride could be readily converted into the hydrogenphosphate salt [PhC(NH) OR′·H3PO4] which, in turn, underwent a selective (>80%) reaction with MeOH to produce TMOB in a 62% isolated yield. This allowed for an unprecedented Pinner-type synthesis of TMOB starting from benzonitrile, rather than from the highly toxic trichloromethylbenzene. Overall, remarkable improvements in safety and process intensification were achieved.

Process for preparation of adjacently disubstituted ketones

A novel 7-hydroxyprostaglandin E1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: STR1 wherein R8 represents H, CH3 or C2 H5, R9 represents H or CH3, R10 and R11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an α,β-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.