Introduction
4,6-Dimethoxy-2-(phenoxycarbonyl)aminopyrimidine (also written phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate, CAS 89392-03-0) is an off-white to white crystalline powder. It is a protected form of 2-amino-4,6-dimethoxypyrimidine, one of the most important building blocks for modern pyrimidinyl crop-protection chemicals. The phenyl carbamate group makes the amino function easy to carry, isolate and couple, which is why this intermediate is handled as a crystalline solid rather than as the more reactive free amine.
Chemical and Physical Properties
The molecule combines a 4,6-dimethoxypyrimidine core with a phenoxycarbonyl (phenyl carbamate) group on the 2-amino position. The two methoxy groups and the carbamate are both good handles for further chemistry.
| Property | Value |
|---|---|
| CAS number | 89392-03-0 |
| Molecular formula | C13H13N3O4 |
| Molecular weight | 275.26 g/mol |
| Appearance | Off-white or white crystalline powder |
| EC number | 406-600-2 |
| Chemical family | Heterocyclic carbamate (pyrimidine) |
| SMILES | COC1=CC(=NC(=N1)NC(=O)OC2=CC=CC=C2)OC |
As a crystalline solid the material is easier to store and dose than a low-boiling amine, and the carbamate both protects the amino group and activates it toward displacement.
The Role of Protected 2-Aminopyrimidines
2-Amino-4,6-dimethoxypyrimidine is the common parent of several herbicide families, but the free amine is not always convenient to handle directly. Converting it to the phenyl carbamate – the compound described here – gives a stable, isolable intermediate in which the amine nitrogen is protected and the carbonyl becomes a good leaving group for the coupling step that forms the final active. This is the classic strategy used to assemble the sulfonylurea bridge and related linkages.
Production and Synthetic Routes
The intermediate is made by acylating 2-amino-4,6-dimethoxypyrimidine at the 2-amino group:
- Reaction with phenyl chloroformate. The amine is treated with phenyl chloroformate, usually in the presence of a base, to give the phenyl carbamate directly.
- Reaction with diphenyl carbonate. Alternatively, diphenyl carbonate can be used as the phenoxycarbonyl source under suitable conditions.
Whichever route is used, the crude solid is purified by crystallisation to reach the off-white to white crystalline form and the assay and water limits written into the specification.
Major Industrial Applications
Sulfonylurea Herbicides
The most important use of this intermediate is in the manufacture of pyrimidinylsulfonylurea herbicides, where the 4,6-dimethoxypyrimidin-2-yl group is a key part of the active. Sulfonylurea herbicides act at very low application rates, so the purity of the pyrimidine intermediate directly affects the quality of the finished active.
Other Pyrimidinyl Crop-Protection Chemicals
The same 4,6-dimethoxypyrimidin-2-yl building block, delivered through this carbamate, is used in other pyrimidinyl herbicide and crop-health actives that rely on the dimethoxypyrimidine heterocycle.
Pharmaceutical and Fine-Chemical Synthesis
Carbamates of 2-aminopyrimidines are also useful in pharmaceutical and fine-chemical synthesis, where the protected amine allows selective transformations before the carbamate is removed or displaced.
Quality and Specifications
Commercial material is sold against a short specification that focuses on appearance, assay and water content.
| Parameter | Specification |
|---|---|
| Appearance | Off-white or white crystalline powder |
| Assay | 98% min |
| Water | 0.2% max |
| Molecular formula | C13H13N3O4 |
| Molecular weight | 275.26 g/mol |
Because the finished herbicide is used at low dose, buyers generally look for a consistent assay and a low, controlled water content. More detail on grades, packaging and documentation is collected in the buying guide, and the herbicide chemistry is covered in the companion article on dimethoxypyrimidinyl carbamate intermediates in herbicide synthesis.
Handling, Safety and Storage
The material is a solid organic intermediate and should be handled as a fine chemical: use appropriate personal protective equipment, avoid generating dust, and keep it away from heat, moisture, strong oxidants and incompatible materials. Store it cool and dry in a tightly closed container. Always consult the current safety data sheet for detailed guidance, including any regulatory classification.
Frequently Asked Questions about this Pyrimidine Carbamate
What is 4,6-dimethoxy-2-(phenoxycarbonyl)aminopyrimidine used for?
It is used mainly as a protected 4,6-dimethoxypyrimidin-2-yl intermediate for sulfonylurea and other pyrimidinyl crop-protection chemicals, and in fine-chemical synthesis.
What is the difference between this compound and 2-amino-4,6-dimethoxypyrimidine?
2-Amino-4,6-dimethoxypyrimidine is the free parent amine; this compound is its phenyl carbamate, a stable, crystalline, protected form that is easier to isolate and to couple.
How is it supplied?
As an off-white to white crystalline powder at 98% min assay and 0.2% max water, in standard industrial packaging with a batch COA.
Where can I buy 4,6-dimethoxy-2-(phenoxycarbonyl)aminopyrimidine?
PolyBlueChem supplies 4,6-dimethoxy-2-(phenoxycarbonyl)aminopyrimidine (CAS 89392-03-0) with COA and MSDS. Contact our team for specifications, packaging and a quotation.
References
- PubChem Compound Summary for 4,6-dimethoxy-2-(phenoxycarbonyl)aminopyrimidine (CAS 89392-03-0).
- Manufacturer specification sheets for the phenyl carbamate of 2-amino-4,6-dimethoxypyrimidine.
- Technical literature on sulfonylurea herbicide intermediates.
Disclaimer: This article is provided for general informational purposes only and does not constitute technical, regulatory or safety advice. Always refer to the current safety data sheet and applicable regulations before handling this material.
PolyBlueChem, as the chemical supplier of all categories, is the supplier of 4,6-dimethoxy-2-(phenoxycarbonyl)aminopyrimidine (CAS 89392-03-0) as well. Contact our team for specifications, packaging and a quotation.