(TRIMETHYLSILYL)ACETONITRILE

CAS No.：18293-53-3

Important Notice

This product is a chemical product/pharmaceutical intermediate. It is not a drug, an active pharmaceutical ingredient (API), or a pharmaceutical-grade material. It has not been granted a drug approval number or a Chemical Drug Substance Approval Notice, has not passed drug-related review and approval, and is not manufactured, tested, or released in accordance with pharmaceutical GMP.
This product is intended solely for non-clinical research, process development, quality studies, further chemical processing, or chemical synthesis. It must not be used in drug-product manufacturing, clinical trials, clinical diagnosis, or administration to humans or animals, or be sold, used as an input, submitted for regulatory filing, or released as an API or pharmaceutical material.
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(TRIMETHYLSILYL)ACETONITRILE Basic information

Product Name:	(TRIMETHYLSILYL)ACETONITRILE
Synonyms:	TMSAN;(TRIMETHYLSILYL)ACETONITRILE;trimethylsilanyl-acetonitrile;(Trimethylsilyl)acetonitrile,(Cyanomethyl)trimethylsilane, TMSAN;2-(Trimethylsilyl)acetonitrile;2-Trimethylsilylacetonitrile;Einecs 242-169-5;Acetonitrile, 2-(triMethylsilyl)-
CAS:	18293-53-3
MF:	C5H11NSi
MW:	113.23
EINECS:	242-169-5
Product Categories:
Mol File:	18293-53-3.mol

(TRIMETHYLSILYL)ACETONITRILE Chemical Properties

Boiling point	65-70 °C20 mm Hg(lit.)
density	0.827 g/mL at 25 °C(lit.)
refractive index	n20/D 1.420(lit.)
Fp	122 °F
storage temp.	Sealed in dry,Room Temperature
solubility	Sol most common organic solvents.
form	Liquid
color	Clear colorless to straw
Specific Gravity	0.829
Hydrolytic Sensitivity	4: no reaction with water under neutral conditions
BRN	1738845
InChIKey	WJKMUGYQMMXILX-UHFFFAOYSA-N

Safety Information

Hazard Codes	T
Risk Statements	10-23/24/25-36/37/38
Safety Statements	26-36/37/39-45
RIDADR	UN 1993 3/PG 3
WGK Germany	3
F	21
TSCA	No
HazardClass	3.2
PackingGroup	III
HS Code	29310099

MSDS Information

Provider	Language
SigmaAldrich	English

(TRIMETHYLSILYL)ACETONITRILE Usage And Synthesis

Physical properties	bp 84–85 °C/54 mmHg, 66 °C/35 mmHg, 65–70 °C/20 mmHg;3 d 0.827 g cm?3.
Uses	α-carbanion is a useful alternative to LiCH2CN for nucleophilic cyanomethylation; (Z)-selective Peterson alkenation). Trimethylsilylacetonitrile participates in the following synthesis reactions: Metalation, Peterson Alkenation (Cyanomethylenation), Michael Addition, Reactions with Other Electrophiles, Cyanomethylation, Metal-Catalyzed Reactions etc.
Uses	(Trimethylsilyl)acetonitrile has been used in catalytic cyanomethylation of various carbonyl compounds in the presence of Lewis bases.
Preparation	From chlorotrimethylsilane, zinc, and XCH2CN, (X = Cl, 61% yield; X = Br, 81% yield).
Purification Methods	Check if NMR and IR spectra show impurities; if present dissolve it in *C6H6 (10volumes), wash it with buffer (AcOH/AcONa pH ca 7) several times, dry (CaCl2) it, evaporate and distil it. IR: (CCl4) 2215 (CN) cm-1, NMR (CCl4): 0.23 (s, 9H, SiMe3), and 1.53 (s, 2H, CH2CN). [Matsuda et al. J Chem Soc, Perkin Trans 1 26 1979, Beilstein 4 IV 3974.]

(TRIMETHYLSILYL)ACETONITRILE Preparation Products And Raw materials

Preparation Products

4-CHLOROBENZOYLACETONITRILE-->3-Methoxybenzoylacetonitrile-->4-CYANOPHENYLACETONITRILE 97-->2-Methylbenzyl cyanide

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