(Trimethylsilyl)acetonitrile

HCID 87557
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Basic information

CAS
18293-53-3
Standard SMILES
C[Si](C)(C)CC#N
InChIKey
WJKMUGYQMMXILX-UHFFFAOYSA-N
Molecular formula
C5H11NSi
Average molar mass
113.23 g/mol
Monoisotopic mass
113.06607588

Names & identifiers

Preferred name
(Trimethylsilyl)acetonitrile
IUPAC
2-trimethylsilylacetonitrile
English name
(TRIMETHYLSILYL)ACETONITRILE
Molecular formula
C5H11NSi
Molecular weight
113.23

Names & synonyms

(Trimethylsilyl)acetonitrile18293-53-32-(trimethylsilyl)acetonitrile2-TRIMETHYLSILYLACETONITRILEAcetonitrile, 2-(trimethylsilyl)-5XB7XHD8BUEINECS 242-169-5DTXSID60171361RefChem:70547DTXCID9093852242-169-5TRIMETHYLSILYLACETONITRILE
Show more names
2-(TrimethyTRIMETHYLSILYACETONITRILE(CYANOMETHYL)TRIMETHYLSILANE
C5H11NSiMFCD00001882trimethylsilanyl-acetonitrileAcetonitrile, (trimethylsilyl)-TMSANAcetonitrile,2-(trimethylsilyl)-TMSCH2CNUNII-5XB7XHD8BU

Database identifiers

CAS
18293-53-3
PubChem CID
87557
DTXSID
DTXSID60171361
UNII
5XB7XHD8BU
EC Number
242-169-5
Nikkaji
J266.101B

Properties

Computed structural properties

Topological polar surface area
23.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
7

Experimental & physicochemical properties

SpringerMaterials PropertiesBoiling point

Physicochemical properties

Boiling point
65 · 65-70 °C20 mm Hg(lit.)
Density
0.827 g/mL · 0.827 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.420(lit.)
Flash point
122 °F · 122 °F
storage temp.
Sealed in dry,Room Temperature
solubility
Sol most common organic solvents.

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationAcetonitrile, (trimethylsilyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Safety data

F
21
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
No
ridadr
UN 1993 3/PG 3
hs_code
29310099

Chemistry & industry

Applications · 2 items

Usesα-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 methods

PreparationFrom chlorotrimethylsilane, zinc, and XCH2CN, (X = Cl, 61% yield; X = Br, 81% yield).

Upstream & downstream products

Suppliers77 total

上海凌富药物研究有限公司+86(21)5895 0110 19945755304 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
毕佳索（上海毕得医药科技股份有限公司）400-6005915 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

Related reactions

14 records
New reaction record

Compound notes

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