CAS 18156-74-6 (Trimethylsilyl)imidazole (HCID 28925)

Overview

N-trimethylsilylimidazole is a member of the class of imidazoles in which the hydrogen at position 1 is replaced by a trimethylsilyl group. N-trimethylsilylimidazole is a derivatisation agent used in gas chromatography/mass spectrometry applications. It has a role as a chromatographic reagent. It is a member of imidazoles and a N-silyl compound.

Names & identifiers

Preferred name: (Trimethylsilyl)imidazole
IUPAC: imidazol-1-yl(trimethyl)silane
English name: N-(Trimethylsilyl)imidazole
Molecular formula: C6H12N2Si
Molecular weight: 140.26

Names & synonyms

18156-74-6N-(Trimethylsilyl)imidazole1-(Trimethylsilyl)-1H-imidazole1-(Trimethylsilyl)imidazole1H-Imidazole, 1-(trimethylsilyl)-TSIM(Trimethylsilyl)imidazoleImidazole, 1-(trimethylsilyl)-1-trimethylsilylimidazoleIMIDAZOLE, N-(TRIMETHYLSILYL)-PX8K4R8KWXAI3-52901

Show more names

TMSITRIMETHYLSILYLIMIDAZOLETMS-IMIDAZOLESIM1-(TRIMETHYLSILYL)IMIDAZOLE, 97%1-(TRIMETHYLSILYL)IMIDAZOLE, 97%1-(TRIMETHYLSILYL)IMIDAZOLE, 97%

N-trimethylsilylimidizoleNSC-139860DTXSID5066326tmsimRefChem:428844DTXCID3035765242-040-3N-Trimethylsilylimidazole

Database identifiers

CAS: 18156-74-6
PubChem CID: 28925
DTXSID: DTXSID5066326
ChEMBL: CHEMBL1565732
ChEBI: CHEBI:85063
UNII: PX8K4R8KWX
EC Number: 242-040-3
Nikkaji: J53.639C

Properties

Computed structural properties

Topological polar surface area: 17.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 1
Heavy atoms: 9
Formal charge: 0
Complexity: 97.7

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Imidazoles

SpringerMaterials Properties29Si nuclear magnetic resonance spectrum

Solubility14.6 [ug/mL] (The mean of the results at pH 7.4)

Physical DescriptionColorless or light yellow liquid; [Alfa Aesar MSDS]

Physicochemical properties

Melting point: -42 °C · -42 °C
Boiling point: 93 · 93-94 °C14 mm Hg(lit.)
Density: 0.957 g/mL · 0.957 g/mL at 20 °C
refractive index: 20 · n20/D 1.475(lit.)
Flash point: 42 °F · 42 °F
storage temp.: 30 °C · Store below +30°C.
solubility: Chloroform
form: Liquid
pka: 7.96 · 7.96±0.10(Predicted)
Specific Gravity: 0.956 · 0.956
color: Clear colorless to yellow
Water Solubility: decomposes
Sensitive: Moisture Sensitive
Hydrolytic Sensitivity: 7 · 7: reacts slowly with moisture/water
BRN: 606148 · 606148
Stability: Air and Moisture Sensitive
InChI: 1S/C6H12N2Si/c1-9(2,3)8-5-4-7-6-8/h4-6H,1-3H3
InChIKey: YKFRUJSEPGHZFJ-UHFFFAOYSA-N
SMILES: C[Si](C)(C)n1ccnc1
CAS DataBase Reference: 18156 · 18156-74-6(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 8 K4R8KWX · PX8K4R8KWX
NIST Chemistry Reference: 1 h-Imidazole, · 1h-Imidazole, 1-(trimethylsilyl)-(18156-74-6)
EPA Substance Registry System: 1 H-Imidazole, · 1H-Imidazole, 1-(trimethylsilyl)- (18156-74-6)
UNSPSC Code: 12352103 · 12352103
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Danger
Hazard statements: 225 · H225-H315-H319-H335
Precautionary statements: 210 · P210-P233-P240-P241-P303+P361+P353-P305+P351+P338
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: F,Xi,C
Risk Statements: 11 · 11-36/37/38-14-40-34-37-35-20/21/22
Safety Statements: 16 · 16-26-33-37/39-45-36/37/39
RIDADR: 1993 · UN 1993 3/PG 2
WGK Germany: 3 · 3
RTECS: 8700000 · NI8700000
F: 10 · 10-21
Autoignition Temperature: 540 °C · 540 °C DIN 51794
TSCA: TSCA listed
HazardClass: 3 · 3
PackingGroup: II
HS Code: 29332990 · 29332990
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Flam. Liq. 2Skin Irrit. 2
REACH Registrations: Active
Limited Quantities: 1 L · 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (56.7%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 90 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: 1H-Imidazole, 1-(trimethylsilyl)-

Status: Active Update: 14-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33681

1H-Imidazole, 1-(trimethylsilyl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses decreased immune response in intraperitoneal lethal-dose studies of mice; [RTECS] Decomposed by water; An irritant; [Alfa Aesar MSDS]

Hazard Classes and CategoriesFlam. Liq. 2 (56.7%)

Safety data

F: 10-21
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
rtecs: NI8700000
ridadr: UN 1993 3/PG 2
hs_code: 29332990
risk_code: 11-36/37/38-14-40-34-37-35-20/21/22
Signal word: Danger
Symbol(GHS): GHS02,GHS07
hazard_code: F,Xi,C
safety_code: 16-26-33-37/39-45-36/37/39
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: II
Hazard statements: H225-H315-H319-H335
Limited Quantities: 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Flam. Liq. 2Skin Irrit. 2
Autoignition Temperature: 540 °C DIN 51794
Precautionary statements: P210-P233-P240-P241-P303+P361+P353-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing Information1H-Imidazole, 1-(trimethylsilyl)-: ACTIVE

Applications · 5 items

UsesA general silylating agent, particularly for alcohols. An intermediate for the synthesis of imidazole derivatives.

UsesSilylating reagent for the protection of hydroxyl groups in the presence of amine functionalities.1

UsesN-(trimethylsilyl) imidazole (TMSim) is quite reactive with hydroxyl groups in a variety of analytes including a variety of lipids.As with other derivatization reactions,microwave heating can greatly improve process efficiency.

UsesN-(Trimethylsilyl)imidazole is a silylating agent for alcohols and 1,3-dicarbonyl compounds; reaction with esters to give imidazolides; preparation of O-trimethylsilyl monothioacetals; aromatization of the A-ring of steroids. It participates in the reactions of Hydroxyl Silylation Reactions, Silyl Aminal Formation Reactions, Nitrogen Silylation Reactions, Acyl Imidazole Formation, Michael Addition Reactions, Substitution Reactions, Phosphoroimidazolidate Formation, and other uses.

General Description1-(Trimethylsilyl)imidazole (TMSIM) has high silyl donor ability. It does not react with amino groups and also does not help in formation of enol-ether on unprotected ketone groups. It is useful as a silylating agent for ecdysones, norepinephrine, dopamine, steroids, sugars, sugar phosphates and ketose isomers.

Upstream & downstream products

Downstream products

Medetomidine 4-Trimethylsiloxy-3-penten-2-one Chlorotrimethylsilane 1,1'-Sulfonyldiimidazole N,N'-Bis(imidazole)dimethylsilane,tech-95 2-O,3-O,4-O,5-O-Tetrakis(trimethylsilyl)-D-ribose 1,1'-Thiocarbonyldiimidazole

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of imidazoles in which the hydrogen at position 1 is replaced by a trimethylsilyl group. N-trimethylsilylimidazole is a derivatisation agent used in gas chromatography/mass spectrometry applications.