13820-09-2 Usage
Chemical Properties
CLEAR COLORLESS LIQUID
Uses
Different sources of media describe the Uses of 13820-09-2 differently. You can refer to the following data:
1. Trimethyl orthovalerate is used in the synthesis of 1,2,4-triazolo[1,5-c]pyrimidine derivatives as human adenosine A3 receptor ligands. It can also be used as a precursor to prepare N-sulfonyl and N-sulfinyl imines and imidates.
2. Trimethyl orthovalerate has been used in the preparation of:various 9-O-acyl derivatives of N-acetyl- and N-glycoloyl-neuraminic acid2-methyl, 2-ethyl, 2-propyl and 2-butyl-3-benzimidazolyl-4(3H)-quinazolinones
Synthesis Reference(s)
Journal of the American Chemical Society, 68, p. 1922, 1946 DOI: 10.1021/ja01214a015
General Description
Kinetics of unimolecular gas-phase elimination of trimethyl orthovalerate has been investigated.
Check Digit Verification of cas no
The CAS Registry Mumber 13820-09-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,8,2 and 0 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 13820-09:
(7*1)+(6*3)+(5*8)+(4*2)+(3*0)+(2*0)+(1*9)=82
82 % 10 = 2
So 13820-09-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H18O3/c1-5-6-7-8(9-2,10-3)11-4/h5-7H2,1-4H3
13820-09-2Relevant articles and documents
A flexible Pinner preparation of orthoesters: The model case of trimethylorthobenzoate
Noe, Marco,Perosa, Alvise,Selva, Maurizio
, p. 2252 - 2260 (2013)
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.
