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16018-87-4

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16018-87-4 Usage

Uses

5-Chloro-6-methyluracil is used in preparation of herbicide.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 1874, 1961 DOI: 10.1021/jo01065a045

Check Digit Verification of cas no

The CAS Registry Mumber 16018-87-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,0,1 and 8 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 16018-87:
(7*1)+(6*6)+(5*0)+(4*1)+(3*8)+(2*8)+(1*7)=94
94 % 10 = 4
So 16018-87-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H5ClN2O2/c1-2-3(6)4(9)8-5(10)7-2/h1H3,(H2,7,8,9,10)

16018-87-4Relevant articles and documents

-

Johnson,Sprague

, p. 1622 (1938)

-

Electrophilic ipso-substitution in uracil derivatives

Chernikova,Khursan,Spirikhin,Yunusov

, p. 2445 - 2453 (2014/11/07)

Treatment of 5-iodo-1,3,6-trimethyluracil with 50% H2SO 4 gives 1,3,6-trimethyluracil; with 5-bromo-1,3,6-trimethyluracil, a mixture of 1,3,6-trimethyluracil and 6-bromomethyl-1,3-dimethyluracil is obtained. 5-Chloro-1,3,6-trimethyluracil remains inert under these conditions. According to the DFT modeling of the reactions of 5-halo-1,3,6-trimethyluracils, a nucleophilic agent can abstract either Hal+ or the methyl proton from the carbocation formed by protonation of the starting halouracil at position 5, which accounts for the formation of two products from the 5-bromo derivative. Under similar conditions, 6-methyluracil dibromohydrin yields N-bromo-5-bromo-6-hydroxymethyluracil. Bromination or chlorination of 5-hydroxymethyl- or 5-formyl-6-methyluracils follows the ipso-substitution scheme leading to 6-methyluracil 5-halo- and 5,5-dihalohydrins.

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