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6-Aminouracil

6-Aminouracil structure

CAS No:
873-83-6
Formula:
C4H5N3O2
Chemical Name:
6-Aminouracil
Synonyms:
2,4(1H,3H)-Pyrimidinedione,6-amino-;Uracil,6-amino-;6-Amino-2,4(1H,3H)-pyrimidinedione;6-Aminouracil;6-Amino-2,4-dihydroxypyrimidine;4-Aminouracil;2,4-Dihydroxy-6-aminopyrimidine;4-Amino-2,6-dihydroxypyrimidine;6-Amino-2,4-dioxo-1,2,3,4-tetrahydropyrimidine;NSC 15919;NSC 7367;6-Aminopyrimidine-2,4(1H,3H)-dione;6-Aminopyrimidine-2,4-diol;56-07-5
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

cream to light brown crystalline powder

6-Aminouracil Basic Attributes

Molecular Weight：

127.1

Exact Mass：

127.10

BRN：

120491

EC Number：

212-854-3

NSC Number：

15919|7367

DSSTox ID：

DTXSID5061241

HScode：

29335995

Characteristics

PSA：

84.2

XLogP3：

-1.6

Appearance：

Cream to light brown Crystalline Powder

Density：

1.7±0.1 g/cm3

Melting Point：

310-312 °C

Boiling Point：

580.4ºC at 760 mmHg

Flash Point：

304.8±30.9 °C

Refractive Index：

1.746

Water Solubility：

slightly soluble

Storage Conditions：

Refrigerator

Toxicity：

Parenteral-mouse LDL0: 2400 mg/kg

Flammability characteristics：

Flammable; high temperature produces toxic nitrogen oxide fumes

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

22-24/25

RTECS Number：

YQ8750000

Storage features：

Warehouse ventilated, low temperature and dry

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 49 companies from 3 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity class：

moderately toxic

Drug Information

MeSH Entry Terms：

6-aminouracil

6-Aminouracil Use and Manufacturing

Methods of Manufacturing

General procedure: Compounds 1a, 1b and 1e were prepared according to the reportedmethods26–34 by the addition of urea, methylurea and/or methylthiourea (0.1 mol) to ethyl cyanoacetate (0.1 mol) in absolute ethanol(290 mL) containing sodium (0.2 mol). The mixture was refluxed for10–12 h, allowed to cool to r.t. and acidified with acetic acid (pH 6).The resulting precipitate was washed with distilled water and dried in adesiccator overnight.1a: Yield 69percent; m.p. > 360 °C (lit. ≥ 360 °C).We have found that the microwave assisted of reaction urea (1 mmol) with cyano acetic acid (1 mmol) under solvent-free conditions results in rapid formation of the corresponding Amino uracil (Figure1).The products were easily obtained by addition of water to the reaction mixture and recrystalization of crude products from ethanol.

Uses

Used as intermediates for pharmaceutical caffeine, theophylline, SDM, etc.

Manufacturing Info：

2,4(1H,3H)-Pyrimidinedione, 6-amino-: ACTIVE

Computed Properties

Molecular Weight:127.10
XLogP3:-1.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Exact Mass:127.038176411
Monoisotopic Mass:127.038176411
Topological Polar Surface Area:84.2
Heavy Atom Count:9
Complexity:196
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Ethyl cyanoacetate

Urea

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