363340
N-Acetylcysteamine
95%
Synonym(s):
N-(2-Mercaptoethyl)acetamide
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Assay
95%
form
liquid
refractive index
n20/D 1.511 (lit.)
bp
138-140 °C/7 mmHg (lit.)
mp
6-7 °C (lit.)
density
1.121 g/mL at 25 °C (lit.)
functional group
amide
thiol
SMILES string
CC(=O)NCCS
InChI
1S/C4H9NOS/c1-4(6)5-2-3-7/h7H,2-3H2,1H3,(H,5,6)
InChI key
AXFZADXWLMXITO-UHFFFAOYSA-N
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General description
N-Acetylcysteamine, also known as N-(2-Mercaptoethyl) acetamide, is a derivative of cysteamine, that is commonly used as a building block for the synthesis of alkylated thiol and thioesters via esterification.
Application
N-Acetylcysteamine can be used as a building block to synthesize:
- N
- -acetylcysteamine (SNAC) thioesters by reacting with various acid derivatives in the presence of 1,1′-carbonyldiimidazole (CDI).
- Thieno[2,3-c]pyrrole derivatives via three-component reaction of 2-acetyl-3-thiophenecarboxaldehyde and various amines.
- Carbapenems, a class of beta-lactam antibiotic agents.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
235.4 °F - closed cup
Flash Point(C)
113 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Organic letters, 11(16), 3606-3609 (2009-07-21)
Efficient syntheses of N-acetyl thienamycin and epithienamycin A in their readily deprotected form are reported where three contiguous stereocenters are established in a single catalytic asymmetric azetidinone-forming reaction. These examples are a template for synthesizing C-5/C-6 cis or trans carbapenems
Isolation, properties, and regulation of a mitochondrial acyl coenzyme A thioesterase from pig heart.
The Journal of biological chemistry, 254(11), 4516-4523 (1979-06-10)
Biochemical and biophysical research communications, 131(2), 786-792 (1985-09-16)
The acetyl transacylase activity of the fatty acid synthase from yeast has been investigated using p-nitrophenylthiol acetate. The chromophoric nature of the nitrophenylthiol moiety affords a convenient spectrophotometric assay for the transacylase function as well as a means to investigate
The Journal of organic chemistry, 63(20), 6947-6951 (2001-10-24)
4H-[1,2,5]Oxadiazolo[3,4-d]pyrimidine-5,7-dione 1-oxides (2) are conveniently prepared in high yields by the oxidative intramolecular cyclization of 6-amino-5-nitro-1H-pyrimidine-2,4-diones (1) employing iodosylbenzene diacetate as an oxidant in the presence of lithium hydride. The generation of nitric oxide (NO) and NO-related species from 2
Journal of the Chemical Society. Perkin Transactions 1, 2345-2345 (1988)
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