363340
N-Acetylcysteamine
95%
Synonym(s):
N-(2-Mercaptoethyl)acetamide
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About This Item
Linear Formula:
CH3CONHCH2CH2SH
CAS Number:
Molecular Weight:
119.19
UNSPSC Code:
12352100
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22
MDL number:
Assay:
95%
Form:
liquid
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
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
Quality Level
Related Categories
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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Journal of the Chemical Society. Perkin Transactions 1, 2345-2345 (1988)
Ewa Maria Musiol-Kroll et al.
Antibiotics (Basel, Switzerland), 7(3) (2018-07-20)
Polyketides belong to the most valuable natural products, including diverse bioactive compounds, such as antibiotics, anticancer drugs, antifungal agents, immunosuppressants and others. Their structures are assembled by polyketide synthases (PKSs). Modular PKSs are composed of modules, which involve sets of
Tetrahedron Letters, 29, 4305-4305 (1988)
Isolation, properties, and regulation of a mitochondrial acyl coenzyme A thioesterase from pig heart.
K Y Lee et al.
The Journal of biological chemistry, 254(11), 4516-4523 (1979-06-10)
Micah J Bodner et al.
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
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