2-Mercaptopyrimidine Chemical Properties

Melting point:

230 °C (dec.)(lit.)

Boiling point:

191.3±23.0 °C(Predicted)

Density 

1.273 (estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

Powder

pka

7.11±0.10(Predicted)

color 

Yellow

Odor

at 0.10 % in propylene glycol. penetrating sharp green onions

Odor Type

onion

BRN 

107105

InChIKey

HBCQSNAFLVXVAY-UHFFFAOYSA-N

LogP

0.981 (est)

CAS DataBase Reference

1450-85-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Mercaptopyrimidine(1450-85-7)

EPA Substance Registry System

2(1H)-Pyrimidinethione (1450-85-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-63-20/21/22

Safety Statements 

22-24/25-36/37

RIDADR 

UN 3335

WGK Germany 

3

F 

13

TSCA 

Yes

HS Code 

29335995

MSDS

• Language:English Provider:2-Mercaptopyrimidine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Mercaptopyrimidine Usage And Synthesis

Chemical Properties

YELLOW POWDER

Uses

2-Pyrimidinethiol has been used to study the highly selective palladium catalyzed kinetic resolutions of the racemic cyclic allylic carbonates and racemic acyclic allylic carbonates. It has also been used to study the photodegradation of 2-pyrimidinethiol in aerated aqueous solution using zinc oxide.

Definition

ChEBI: Pyrimidine substituted at C-2 by a sulfanyl group.

Synthesis

The general procedure for the synthesis of 2-mercaptopiperidine from 1,1,3,3-tetramethoxypropane and N-methylthiourea is as follows: Example 4 Synthesis of 2(1H)-pyrimidinethione, 1-methyl: A mixture of 1-methyl-2-thiourea (76.6 g, 0.85 mol) and malondialdehyde bis(dimethyl acetal) (126.8 g, 0.77 mol) in ethanol (1.5 L) was stirred, and 10 M hydrochloric acid (76.6 mL, 0.77 mol) was added in one go. The reaction mixture was stirred at 25 °C for 18 h and subsequently concentrated under vacuum by rotary evaporator. The residue was dissolved in water (1.25 L), the solution was alkalized by batchwise addition of potassium carbonate and extracted with dichloromethane (4 x 500 mL). The organic phases were combined, dried with magnesium sulfate and subsequently concentrated to a solid under vacuum by rotary evaporator. The crude product was recrystallized with ethanol (600 mL) and then dried under vacuum at room temperature to constant weight to give 22.9 g (23% yield) of the target product with a melting point of 186-188 °C (uncorrected). The reaction process was repeated to obtain a total of 40.7 g of product.

References

[1] Patent: US2002/12639, 2002, A1
[2] Patent: US6495125, 2002, B2

2-Mercaptopyrimidine(1450-85-7)Related Product Information

• 4-Amino-2-mercaptopyrimidine, 4-Amino-2-thiopyrimidine,4-AMINO-2-MERCAPTOPYRIMIDINE 97%
• 4,6-DIAMINO-2-MERCAPTOPYRIMIDINE
• 6,8-DIHYDROXY-2-METHYLMERCAPTOPURINE
• 6-Aminothiouracil
• 4-Chloro-6-methyl-2-(methylthio)pyrimidine
• Ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate
• 2-Thioisoorotic acid ethyl ester, 5-Carbethoxy-4-hydroxy-2-mercaptopyrimidine, Ethyl 2-thiouracil-5-carboxylate
• S-Boc-2-mercapto-4,6-dimethylpyrimidine
• Benzyl-4,6-dimethyl-pyrimidine-2-thio formate
• 4-AMINO-6-MERCAPTOPYRAZOLO[3,4-D]PYRIMIDINE
• 2-MERCAPTO-4-METHYLPYRIMIDINE HYDROCHLORIDE
• (2-PYRIMIDYLTHIO)ACETIC ACID
• 4,6-DICHLORO-2-METHYLTHIO-5-PHENYLPYRIMIDINE
• 2-Mercaptopyrimidine
• 4-Amino-6-chloro-2-(methylthio)pyrimidine
• 4-Chloro-2-methylthiopyrimidine
• 2-Methylthio-4,6-pyrimidinedione
• 4,6-Dimethyl-2-mercaptopyrimidine